| Date | Time | Type | Home School | Away School | Site |
| MON 8/12 | 1:45 PM | Practice | Joel Barlow | | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| MON 8/12 | 2:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| MON 8/12 | 3:00 PM | Practice | Bunnell | | Bunnell HS - Short Beach |
| MON 8/12 | 3:00 PM | Practice | Ridgefield | | Ridgefield Golf Course - Ridgefield Golf Course |
| MON 8/12 | 3:00 PM | Practice | Brookfield | | Sunset Hill Golf Course - Golf Quest |
| MON 8/12 | 7:00 PM | Practice | Shepaug Valley | | Virtual Meeting - Virtual Meeting |
| TUE 8/13 | 1:45 PM | Practice | Joel Barlow | | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| TUE 8/13 | 11:00 AM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| TUE 8/13 | 11:00 AM | Practice | Ridgefield | | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 8/13 | 2:00 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| TUE 8/13 | 2:00 PM | Practice | Shepaug Valley | | Shepaug Valley High School - Shepaug Valley School |
| WED 8/14 | 1:45 PM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| WED 8/14 | 11:30 AM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| WED 8/14 | 2:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| WED 8/14 | 3:00 PM | Practice | Ridgefield | | Silver Spring Golf Course - Silver Spring Golf Course |
| WED 8/14 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| THU 8/15 | 1:45 PM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| THU 8/15 | 10:00 AM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| THU 8/15 | 2:00 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| THU 8/15 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| THU 8/15 | 9:00 AM | Practice | Ridgefield | | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| MON 8/19 | 3:00 PM | Practice | Ridgefield | | Ridgefield Golf Course - Ridgefield Golf Course |
| MON 8/19 | Canceled | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| MON 8/19 | Canceled | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| MON 8/19 | Postponed | Scrimmage | New Fairfield | Danbury | Club River Oaks - Club River Oaks |
| MON 8/19 | Postponed | Scrimmage | Conard | Glastonbury, Newington, Avon, Berlin, Pomperaug, Simsbury, Wethersfield, Hall | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 8/20 | 11:00 AM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| TUE 8/20 | 2:30 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| TUE 8/20 | 3:00 PM | Non-League | Stratford | Bethel | Mill River Country Club - Mill River Country Club |
| TUE 8/20 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| TUE 8/20 | 3:15 PM | League | Trumbull | Ridgefield | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 8/20 | 8:45 AM | Practice | Joel Barlow | | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 8/21 | 1:00 PM | Non-League | Newtown | Brookfield | Rock Ridge Country Club - Rock Ridge Country Club |
| WED 8/21 | 11:00 AM | League | Pomperaug | Joel Barlow | Pomperaug High School - Highfield Country Club |
| WED 8/21 | 12:00 PM | Non-League | Lakeview | Northwestern | Lakeview High School - Litchfield Country Club (LCC) |
| WED 8/21 | 2:00 PM | League | Weston | Stratford | Weston High School - Aspetuck Country Club |
| WED 8/21 | 3:00 PM | Non-League | Bethel | Bunnell | Bethel High School - Connecticut Country Club |
| WED 8/21 | 3:00 PM | Non-League | Wethersfield | Fairfield Prep, Northwest Catholic | Wethersfield Country Club - Wethersfield Country Club |
| WED 8/21 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| WED 8/21 | 3:00 PM | Practice | Ridgefield | | Ridgefield Golf Course - Ridgefield Golf Course |
| WED 8/21 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Range |
| WED 8/21 | 3:10 PM | League | St. Joseph | Trumbull | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| THU 8/22 | 10:00 AM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| THU 8/22 | 3:00 PM | League | Avon | Simsbury | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| THU 8/22 | 3:00 PM | League | Danbury | Greenwich | Richter Park Golf Course - Richter Park Golf Course |
| THU 8/22 | 3:00 PM | League | Immaculate | New Milford | Richter Park Golf Course - Richter Park Golf Course |
| THU 8/22 | 3:00 PM | League | Hall | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 8/22 | 3:00 PM | League | Ridgefield | Brien McMahon | Silver Spring Golf Course - Silver Spring Golf Course |
| THU 8/22 | 3:00 PM | League | Berlin | Windsor | Timberlin Golf Course - Timberlin Golf Course |
| THU 8/22 | 3:00 PM | Non-League | Fairfield Prep | Darien | Brooklawn Country Club - Brooklawn Country Club |
| THU 8/22 | 3:00 PM | Non-League | Bunnell | New Fairfield | Bunnell HS - Blackhawk Country Club (Old OCC) |
| THU 8/22 | 3:00 PM | Non-League | Masuk | Joel Barlow | Whitney Farms Golf Course - Whitney Farms Golf Course |
| MON 8/26 | 10:00 AM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| MON 8/26 | 2:00 PM | League | Joel Barlow | Newtown | Redding Country Club - Redding Country Club |
| MON 8/26 | 2:30 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| MON 8/26 | 3:00 PM | League | Bethel | Stratford | Bethel High School - Connecticut Country Club |
| MON 8/26 | 3:00 PM | League | New Fairfield | Bunnell | Club River Oaks - Club River Oaks |
| MON 8/26 | 3:00 PM | League | Stamford | Greenwich | Stamford High - Sterling Farms Golf Course |
| MON 8/26 | 3:00 PM | League | Masuk | Pomperaug | Whitney Farms Golf Course - Whitney Farms Golf Course |
| MON 8/26 | 3:00 PM | Practice | Ridgefield | | TBA - TBA |
| MON 8/26 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| MON 8/26 | 3:15 PM | League | Wilton | Fairfield Ludlowe | Rolling Hills Country Club - Rolling Hills Country Club |
| MON 8/26 | Postponed | League | Gilbert | Housatonic Regional | Green woods Country Club - Green woods Country Club |
| TUE 8/27 | 3:00 PM | League | Bethel | New Fairfield | Bethel High School - Connecticut Country Club |
| TUE 8/27 | 3:00 PM | League | Avon | Hall | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| TUE 8/27 | 3:00 PM | League | New Milford | Brookfield | Candlewood Valley Country Club - Candlewood Valley Country Club |
| TUE 8/27 | 3:00 PM | League | Westhill | Trumbull | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| TUE 8/27 | 3:00 PM | League | Lewis Mills | Northwest Catholic | Lewis Mills High School - Fairview Farm Golf Course |
| TUE 8/27 | 3:00 PM | League | Immaculate | Joel Barlow | Richter Park Golf Course - Richter Park Golf Course |
| TUE 8/27 | 3:00 PM | League | Newtown | Weston | Rock Ridge Country Club - Rock Ridge Country Club |
| TUE 8/27 | 3:00 PM | League | Conard | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 8/27 | 3:00 PM | League | Ridgefield | Fairfield Ludlowe | Silver Spring Golf Course - Silver Spring Golf Course |
| TUE 8/27 | 3:00 PM | League | Southington | Farmington | Southington High School - Southington Country Club |
| TUE 8/27 | 3:00 PM | League | Wethersfield | Berlin | Wethersfield Country Club - Wethersfield Country Club |
| TUE 8/27 | 3:00 PM | League | Rocky Hill | | Wethersfield High School |
| TUE 8/27 | 3:00 PM | Non-League | Fairfield Prep | Staples | CC of Fairfield - CC of Fairfield |
| TUE 8/27 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Range |
| TUE 8/27 | 3:30 PM | League | Norwalk | Darien | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 8/27 | 3:30 PM | League | Wilton | Danbury | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 8/28 | 2:50 PM | League | Fairfield Ludlowe | Trumbull | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 8/28 | 3:00 PM | League | New Canaan | Ridgefield | CCNC - CCNC |
| WED 8/28 | 3:00 PM | League | Westhill | Wilton | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 8/28 | 3:00 PM | League | Notre Dame Prep | New Fairfield | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 8/28 | 3:00 PM | League | Newington | Glastonbury | Indian Hill Country Club - Indian Hill Country Club |
| WED 8/28 | 3:00 PM | League | Pomperaug | Immaculate | Pomperaug High School - Highfield Country Club |
| WED 8/28 | 3:00 PM | Non-League | New Milford | Shepaug Valley | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 8/28 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| WED 8/28 | 3:10 PM | League | St. Joseph | Fairfield Warde | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 8/28 | 3:30 PM | Non-League | Lakeview | Housatonic Regional | Lakeview High School - Litchfield Country Club (LCC) |
| THU 8/29 | 2:30 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| THU 8/29 | 3:00 PM | League | Avon | Northwest Catholic | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| THU 8/29 | 3:00 PM | League | Bunnell | Bethel | Bunnell HS - Blackhawk Country Club (Old OCC) |
| THU 8/29 | 3:00 PM | League | Newington | Berlin | Indian Hill Country Club - Indian Hill Country Club |
| THU 8/29 | 3:00 PM | League | Stratford | New Milford | Mill River Country Club - Mill River Country Club |
| THU 8/29 | 3:00 PM | League | Hall | Simsbury | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 8/29 | 3:00 PM | League | Ridgefield | Stamford | Silver Spring Golf Course - Silver Spring Golf Course |
| THU 8/29 | 3:00 PM | League | Southington | Lewis Mills | Southington High School - Southington Country Club |
| THU 8/29 | 3:00 PM | League | New Britain | Glastonbury | Stanley Golf Course - Stanley Golf Course |
| THU 8/29 | 3:00 PM | League | Brookfield | Masuk | Sunset Hill Golf Course - Sunset Hill Golf Course |
| THU 8/29 | 3:00 PM | League | Farmington | Conard | Tunxis Country Club - Tunxis Country Club |
| THU 8/29 | 3:00 PM | Non-League | Housatonic Regional | Mount Everett Regional High School MA | Canaan Country Club - Canaan Country Club |
| THU 8/29 | 3:00 PM | Non-League | New Fairfield | Notre Dame Prep | Club River Oaks - Club River Oaks |
| THU 8/29 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| THU 8/29 | 3:15 PM | League | Staples | Norwalk | Longshore Golf Course - Longshore Golf Course |
| THU 8/29 | 3:15 PM | League | Weston | Joel Barlow | Weston High School - Aspetuck Country Club |
| THU 8/29 | 3:15 PM | League | Darien | Westhill | Woodway Country Club - Woodway Country Club |
| THU 8/29 | 3:30 PM | League | Greenwich | Fairfield Warde | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| TUE 9/3 | 2:30 PM | League | Stamford | Fairfield Warde | Stamford High - Sterling Farms Golf Course |
| TUE 9/3 | 2:30 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/3 | 2:45 PM | League | Windsor | Glastonbury | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 9/3 | 3:00 PM | League | New Milford | Notre Dame Prep | Candlewood Valley Country Club - Candlewood Valley Country Club |
| TUE 9/3 | 3:00 PM | League | New Canaan | Fairfield Ludlowe | CCNC - CCNC |
| TUE 9/3 | 3:00 PM | League | Nonnewaug | Shepaug Valley | Crestbrook Park - Crestbrook Park Golf |
| TUE 9/3 | 3:00 PM | League | Gilbert | Housatonic Regional | Green woods Country Club - Green woods Country Club |
| TUE 9/3 | 3:00 PM | League | Lakeview | Northwestern | Lakeview High School - Litchfield Country Club (LCC) |
| TUE 9/3 | 3:00 PM | League | Stratford | Masuk | Mill River Country Club - Mill River Country Club |
| TUE 9/3 | 3:00 PM | League | Pomperaug | Bunnell | Pomperaug High School - Highfield Country Club |
| TUE 9/3 | 3:00 PM | League | Joel Barlow | New Fairfield | Redding Country Club - Redding Country Club |
| TUE 9/3 | 3:00 PM | League | Conard | Northwest Catholic | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/3 | 3:00 PM | League | Ridgefield | Westhill | Silver Spring Golf Course - Silver Spring Golf Course |
| TUE 9/3 | 3:00 PM | League | Simsbury | Lewis Mills | Simsbury High School - Simsbury Farms CC |
| TUE 9/3 | 3:00 PM | League | Southington | Hall | Southington High School - Southington Country Club |
| TUE 9/3 | 3:00 PM | League | Farmington | Avon | Tunxis Country Club - Tunxis Country Club |
| TUE 9/3 | 3:00 PM | League | Wethersfield | New Britain | Wethersfield Country Club - Wethersfield Country Club |
| TUE 9/3 | 3:15 PM | League | Brien McMahon | Staples | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/3 | 3:15 PM | League | Trumbull | Darien | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 9/3 | 3:30 PM | League | Greenwich | Wilton | Round Hill Country Club - Round Hill Country Club |
| WED 9/4 | 3:00 PM | League | Bethel | Weston | Bethel High School - Connecticut Country Club |
| WED 9/4 | 3:00 PM | League | New Milford | Bunnell | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/4 | 3:00 PM | League | Fairfield Warde | New Canaan | Patterson Club - Patterson Club |
| WED 9/4 | 3:00 PM | League | Newtown | Immaculate | Rock Ridge Country Club - Rock Ridge Country Club |
| WED 9/4 | 3:00 PM | Non-League | Newington | Fairfield Prep | Indian Hill Country Club - Indian Hill Country Club |
| WED 9/4 | 3:00 PM | Non-League | Pomperaug | Masuk | Pomperaug High School - Highfield Country Club |
| WED 9/4 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| WED 9/4 | 3:10 PM | League | St. Joseph | Westhill | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 9/4 | 3:30 PM | League | Norwalk | Wilton, Ridgefield | Oak Hills Golf Course - Oak Hills Golf Course |
| THU 9/5 | 2:15 PM | League | Immaculate | New Fairfield | Richter Park Golf Course - Richter Park Golf Course |
| THU 9/5 | 2:50 PM | League | Fairfield Ludlowe | Stamford | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/5 | 3:00 PM | League | Bethel | Joel Barlow | Bethel High School - Connecticut Country Club |
| THU 9/5 | 3:00 PM | League | Avon | Southington | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| THU 9/5 | 3:00 PM | League | Bunnell | Weston | Bunnell HS - Blackhawk Country Club (Old OCC) |
| THU 9/5 | 3:00 PM | League | New Canaan | Brien McMahon | CCNC - CCNC |
| THU 9/5 | 3:00 PM | League | Nonnewaug | Gilbert | Crestbrook Park - Crestbrook Park Golf |
| THU 9/5 | 3:00 PM | League | Notre Dame Prep | Pomperaug | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 9/5 | 3:00 PM | League | Lewis Mills | Conard | Lewis Mills High School - Fairview Farm Golf Course |
| THU 9/5 | 3:00 PM | League | Stratford | Brookfield | Mill River Country Club - Mill River Country Club |
| THU 9/5 | 3:00 PM | League | Danbury | Fairfield Warde | Richter Park Golf Course - Richter Park Golf Course |
| THU 9/5 | 3:00 PM | League | Ridgefield | St. Joseph | Ridgefield Golf Course - Ridgefield Golf Course |
| THU 9/5 | 3:00 PM | League | Hall | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/5 | 3:00 PM | League | Berlin | New Britain | Timberlin Golf Course - Timberlin Golf Course |
| THU 9/5 | 3:00 PM | League | Northwest Catholic | Simsbury, Wethersfield | Wampanoag Country Club - Wampanoag Country Club |
| THU 9/5 | 3:00 PM | League | Shepaug Valley | Northwestern | Washington Club Golf Course - Washington Club Golf Course |
| THU 9/5 | 3:00 PM | League | Masuk | Newtown | Whitney Farms Golf Course - Whitney Farms Golf Course |
| THU 9/5 | 3:15 PM | League | Staples | Trumbull | Longshore Golf Course - Longshore Golf Course |
| THU 9/5 | 3:30 PM | League | Greenwich | Norwalk | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| THU 9/5 | 3:30 PM | League | Lakeview | Housatonic Regional | Lakeview High School - Litchfield Country Club (LCC) |
| FRI 9/6 | 3:30 PM | Practice | Brookfield | | TBA - TBA |
| MON 9/9 | 3:00 PM | League | New Fairfield | Masuk | Club River Oaks - Club River Oaks |
| MON 9/9 | 3:00 PM | League | Gilbert | Shepaug Valley | Green woods Country Club - Green woods Country Club |
| MON 9/9 | 3:00 PM | League | Greenwich | New Canaan | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| MON 9/9 | 3:00 PM | League | Newington | Wethersfield, Windsor | Indian Hill Country Club - Indian Hill Country Club |
| MON 9/9 | 3:00 PM | League | Lakeview | Nonnewaug | Lakeview High School - Litchfield Country Club (LCC) |
| MON 9/9 | 3:00 PM | League | Northwestern | Housatonic Regional | Northwestern Regional H.S. - Norfolk CC |
| MON 9/9 | 3:00 PM | League | Joel Barlow | Notre Dame Prep | Redding Country Club - Redding Country Club |
| MON 9/9 | 3:00 PM | League | Immaculate | Stratford | Richter Park Golf Course - Richter Park Golf Course |
| MON 9/9 | 3:00 PM | League | Stamford | Trumbull | Stamford High - Sterling Farms Golf Course |
| MON 9/9 | 3:00 PM | Non-League | New Milford | Newtown | Candlewood Valley Country Club - Candlewood Valley Country Club |
| MON 9/9 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| MON 9/9 | 3:15 PM | League | Darien | Ridgefield | Wee Burn CC - Wee Burn CC |
| MON 9/9 | 3:15 PM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| MON 9/9 | 9:00 AM | Non-League | Berlin | Conard, Avon, Farmington, Glastonbury, Fairfield Prep, Pomperaug, St. Joseph | Timberlin Golf Course - Timberlin Golf Course |
| TUE 9/10 | 3:00 PM | League | Westhill | Greenwich | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| TUE 9/10 | 3:00 PM | League | Shepaug Valley | New Milford | Lake Waramaug Country Club - Lake Waramaug Country Club |
| TUE 9/10 | 3:00 PM | League | Lewis Mills | Hall | Lewis Mills High School - Fairview Farm Golf Course |
| TUE 9/10 | 3:00 PM | League | Pomperaug | Stratford | Pomperaug High School - Highfield Country Club |
| TUE 9/10 | 3:00 PM | League | Danbury | Staples, Stamford | Richter Park Golf Course - Richter Park Golf Course |
| TUE 9/10 | 3:00 PM | League | Newtown | Bethel | Rock Ridge Country Club - Rock Ridge Country Club |
| TUE 9/10 | 3:00 PM | League | Fairfield Warde | Brien McMahon | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/10 | 3:00 PM | League | Southington | Simsbury | Southington High School - Southington Country Club |
| TUE 9/10 | 3:00 PM | League | New Britain | Rocky Hill, Windsor | Stanley Golf Course - Stanley Golf Course |
| TUE 9/10 | 3:00 PM | League | Brookfield | Notre Dame Prep | Sunset Hill Golf Course - Sunset Hill Golf Course |
| TUE 9/10 | 3:00 PM | League | Berlin | Glastonbury | Timberlin Golf Course - Timberlin Golf Course |
| TUE 9/10 | 3:00 PM | League | Northwest Catholic | Farmington | Wampanoag Country Club - Wampanoag Country Club |
| TUE 9/10 | 3:00 PM | Practice | Ridgefield | | TBA - TBA |
| TUE 9/10 | 3:15 PM | League | Fairfield Ludlowe | St. Joseph | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/10 | 3:15 PM | League | Trumbull | Norwalk | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 9/10 | 3:30 PM | League | Wilton | Darien | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 9/11 | 2:30 PM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| WED 9/11 | 3:00 PM | League | Bunnell | Stratford | Bunnell HS - Blackhawk Country Club (Old OCC) |
| WED 9/11 | 3:00 PM | League | Housatonic Regional | Nonnewaug | Canaan Country Club - Canaan Country Club |
| WED 9/11 | 3:00 PM | League | New Milford | Immaculate | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/11 | 3:00 PM | League | Westhill | Staples | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 9/11 | 3:00 PM | League | Notre Dame Prep | Weston | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 9/11 | 3:00 PM | League | Newington | New Britain | Indian Hill Country Club - Indian Hill Country Club |
| WED 9/11 | 3:00 PM | League | Fairfield Warde | Ridgefield | Patterson Club - Patterson Club |
| WED 9/11 | 3:00 PM | League | Conard | Wethersfield, Avon | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| WED 9/11 | 3:00 PM | League | Berlin | Rocky Hill | Timberlin Golf Course - Timberlin Golf Course |
| WED 9/11 | 3:00 PM | Non-League | Bethel | Shepaug Valley | Bethel High School - Connecticut Country Club |
| WED 9/11 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| WED 9/11 | 3:10 PM | League | Darien | Fairfield Ludlowe | Wee Burn CC - Wee Burn CC |
| WED 9/11 | 3:15 PM | League | Stamford | Wilton | Stamford High - Sterling Farms Golf Course |
| WED 9/11 | 3:15 PM | League | Trumbull | New Canaan | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 9/11 | 3:15 PM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| WED 9/11 | 3:40 PM | League | Brien McMahon | St. Joseph | Oak Hills Golf Course - Oak Hills Golf Course |
| THU 9/12 | 3:00 PM | League | Avon | Lewis Mills | Blue Fox Run Golf Course - Blue Fox Run Golf Course |
| THU 9/12 | 3:00 PM | League | New Canaan | Westhill | CCNC - CCNC |
| THU 9/12 | 3:00 PM | League | Glastonbury | Wethersfield | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| THU 9/12 | 3:00 PM | League | Lakeview | Shepaug Valley | Lakeview High School - Litchfield Country Club (LCC) |
| THU 9/12 | 3:00 PM | League | Litchfield | Nonnewaug | Litchfield Country Club - Litchfield Country Club |
| THU 9/12 | 3:00 PM | League | Northwestern | Gilbert | Northwestern Regional H.S. - Norfolk CC |
| THU 9/12 | 3:00 PM | League | Immaculate | Notre Dame Prep | Richter Park Golf Course - Richter Park Golf Course |
| THU 9/12 | 3:00 PM | League | Hall | Conard | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/12 | 3:00 PM | League | Rocky Hill | Newington | Rocky Hill High School - Stanley Golf Course |
| THU 9/12 | 3:00 PM | League | Simsbury | Farmington | Simsbury High School - Simsbury Farms CC |
| THU 9/12 | 3:00 PM | League | Southington | Northwest Catholic | Southington High School - Southington Country Club |
| THU 9/12 | 3:00 PM | League | New Britain | | Stanley Golf Course - Stanley Golf Course |
| THU 9/12 | 3:00 PM | League | Brookfield | Pomperaug | Sunset Hill Golf Course - Sunset Hill Golf Course |
| THU 9/12 | 3:00 PM | Non-League | Fairfield Warde | Fairfield Prep | CC of Fairfield - CC of Fairfield |
| THU 9/12 | 3:15 PM | League | Brien McMahon | Danbury | Oak Hills Golf Course - Oak Hills Golf Course |
| THU 9/12 | 3:30 PM | League | Norwalk | Danbury | Oak Hills Golf Course - Oak Hills Golf Course |
| THU 9/12 | Canceled | Practice | Joel Barlow | | Golf Ranch Hitting Range - Golf Quest Hitting Range |
| MON 9/16 | 3:00 PM | League | Bethel | Brookfield | Bethel High School - Connecticut Country Club |
| MON 9/16 | 3:00 PM | League | New Fairfield | New Milford | Club River Oaks - Club River Oaks |
| MON 9/16 | 3:00 PM | League | Nonnewaug | Northwestern | Crestbrook Park - Crestbrook Park Golf |
| MON 9/16 | 3:00 PM | League | Wethersfield | Glastonbury | Goodwin Park Golf Course - Goodwin Park Golf Course |
| MON 9/16 | 3:00 PM | League | Stratford | Newtown | Mill River Country Club - Mill River Country Club |
| MON 9/16 | 3:00 PM | League | Simsbury | Rocky Hill | Simsbury High School - Simsbury Farms CC |
| MON 9/16 | 3:00 PM | League | Shepaug Valley | Housatonic Regional | Washington Club Golf Course - Washington Club Golf Course |
| MON 9/16 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| MON 9/16 | 3:00 PM | Practice | Ridgefield | | TBA - TBA |
| MON 9/16 | 3:15 PM | League | Darien | St. Joseph | Wee Burn CC - Wee Burn CC |
| MON 9/16 | 3:15 PM | League | Weston | Pomperaug | Weston High School - Aspetuck Country Club |
| MON 9/16 | 4:00 PM | League | Gilbert | Lakeview | Green woods Country Club - Green woods Country Club |
| MON 9/16 | Postponed | League | New Canaan | Staples | CCNC - CCNC |
| TUE 9/17 | 2:45 PM | League | Windsor | New Britain | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 9/17 | 2:50 PM | League | Fairfield Ludlowe | Danbury | Smith Richardson Golf Course - Smith Richardson Golf Course |
| TUE 9/17 | 3:00 PM | League | Glastonbury | Berlin | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| TUE 9/17 | 3:00 PM | League | Lewis Mills | Farmington | Lewis Mills High School - Fairview Farm Golf Course |
| TUE 9/17 | 3:00 PM | League | Conard | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/17 | 3:00 PM | League | Simsbury | Avon | Simsbury High School - Simsbury Farms CC |
| TUE 9/17 | 3:00 PM | League | Brookfield | Joel Barlow | Sunset Hill Golf Course - Sunset Hill Golf Course |
| TUE 9/17 | 3:00 PM | League | Northwest Catholic | Hall | Wampanoag Country Club - Wampanoag Country Club |
| TUE 9/17 | 3:00 PM | League | Masuk | Immaculate | Whitney Farms Golf Course - Whitney Farms Golf Course |
| TUE 9/17 | 3:00 PM | Non-League | Bethel | Newtown | Bethel High School - Connecticut Country Club |
| TUE 9/17 | 3:00 PM | Non-League | Shepaug Valley | New Fairfield | Lake Waramaug Country Club - Lake Waramaug Country Club |
| TUE 9/17 | 3:15 PM | League | Trumbull | Fairfield Warde | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 9/17 | 3:30 PM | League | Greenwich | Ridgefield | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| TUE 9/17 | 3:30 PM | League | Norwalk | New Canaan | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/17 | 3:30 PM | League | Wilton | Brien McMahon | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 9/18 | 2:30 PM | League | Newtown | Bunnell | Rock Ridge Country Club - Rock Ridge Country Club |
| WED 9/18 | 2:30 PM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| WED 9/18 | 3:00 PM | League | New Milford | Bethel | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/18 | 3:00 PM | League | Farmington | Lewis Mills | Tunxis Country Club - Tunxis Country Club |
| WED 9/18 | 3:00 PM | League | Wethersfield | Rocky Hill, Hall | Wethersfield Country Club - Wethersfield Country Club |
| WED 9/18 | 3:00 PM | League | Masuk | Weston | Whitney Farms Golf Course - Whitney Farms Golf Course |
| WED 9/18 | 3:00 PM | Non-League | Fairfield Prep | Ridgefield | Patterson Club - Patterson Club |
| WED 9/18 | 3:00 PM | Non-League | Conard | Newington, Glastonbury, Berlin | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| WED 9/18 | 3:00 PM | Practice | Danbury | | Gainfield Farms Golf Course - Gainfield Farms Golf Course |
| WED 9/18 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Range |
| WED 9/18 | 3:10 PM | League | St. Joseph | Greenwich, Trumbull | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 9/18 | 3:15 PM | League | Staples | Stamford | Longshore Golf Course - Longshore Golf Course |
| WED 9/18 | 3:15 PM | League | Brien McMahon | Fairfield Ludlowe | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 9/18 | 3:15 PM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| THU 9/19 | 2:45 PM | League | Windsor | Rocky Hill | Goodwin Park Golf Course - Goodwin Park Golf Course |
| THU 9/19 | 3:00 PM | League | Bunnell | Immaculate | Bunnell HS - Blackhawk Country Club (Old OCC) |
| THU 9/19 | 3:00 PM | League | Housatonic Regional | Gilbert | Canaan Country Club - Canaan Country Club |
| THU 9/19 | 3:00 PM | League | Notre Dame Prep | Stratford | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| THU 9/19 | 3:00 PM | League | Simsbury | Conard | Simsbury High School - Simsbury Farms CC |
| THU 9/19 | 3:00 PM | League | New Britain | Newington | Stanley Golf Course - Stanley Golf Course |
| THU 9/19 | 3:00 PM | League | Brookfield | Weston | Sunset Hill Golf Course - Sunset Hill Golf Course |
| THU 9/19 | 3:00 PM | League | Berlin | Wethersfield | Timberlin Golf Course - Timberlin Golf Course |
| THU 9/19 | 3:00 PM | League | Farmington | Southington | Tunxis Country Club - Tunxis Country Club |
| THU 9/19 | 3:00 PM | League | Northwest Catholic | Lewis Mills | Wampanoag Country Club - Wampanoag Country Club |
| THU 9/19 | 3:00 PM | League | Shepaug Valley | Nonnewaug | Washington Club Golf Course - Washington Club Golf Course |
| THU 9/19 | 3:00 PM | Non-League | Joel Barlow | Pomperaug | Redding Country Club - Redding Country Club |
| THU 9/19 | 3:15 PM | League | Staples | Wilton | Longshore Golf Course - Longshore Golf Course |
| THU 9/19 | 3:15 PM | League | Darien | Danbury | Wee Burn CC - Wee Burn CC |
| THU 9/19 | 3:30 PM | League | Greenwich | Brien McMahon | Griffith E Harris Golf Course - Griffith E Harris Golf Course |
| FRI 9/20 | 3:00 PM | League | Hall | Avon | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| MON 9/23 | 3:00 PM | League | Gilbert | Nonnewaug | Green woods Country Club - Green woods Country Club |
| MON 9/23 | 3:00 PM | League | Northwestern | Shepaug Valley | Northwestern Regional H.S. - Norfolk CC |
| MON 9/23 | 3:00 PM | League | Joel Barlow | New Milford | Redding Country Club - Redding Country Club |
| MON 9/23 | 3:00 PM | League | Immaculate | Brookfield | Ridgewood CC - Ridgewood CC |
| MON 9/23 | 3:00 PM | League | Stamford | Darien | Stamford High - Sterling Farms Golf Course |
| MON 9/23 | 3:15 PM | League | Staples | Fairfield Warde | Longshore Golf Course - Longshore Golf Course |
| MON 9/23 | 3:15 PM | League | Greenwich | Fairfield Prep | Round Hill Country Club - Round Hill Country Club |
| MON 9/23 | 3:30 PM | League | Danbury | Westhill | Richter Park Golf Course - Richter Park Golf Course |
| MON 9/23 | 4:00 PM | League | Housatonic Regional | Lakeview | Canaan Country Club - Canaan Country Club |
| MON 9/23 | Postponed | League | New Canaan | St. Joseph | CCNC - CCNC |
| TUE 9/24 | 2:30 PM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| TUE 9/24 | 3:00 PM | League | Bunnell | Masuk | Bunnell HS - Blackhawk Country Club (Old OCC) |
| TUE 9/24 | 3:00 PM | League | Fairfield Warde | Darien | CC of Fairfield - CC of Fairfield |
| TUE 9/24 | 3:00 PM | League | New Fairfield | Stratford | Club River Oaks - Club River Oaks |
| TUE 9/24 | 3:00 PM | League | Wethersfield | Windsor | Goodwin Park Golf Course - Goodwin Park Golf Course |
| TUE 9/24 | 3:00 PM | League | Lewis Mills | Southington | Lewis Mills High School - Fairview Farm Golf Course |
| TUE 9/24 | 3:00 PM | League | Pomperaug | New Milford | Pomperaug High School - Highfield Country Club |
| TUE 9/24 | 3:00 PM | League | Conard | Farmington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 9/24 | 3:00 PM | League | Ridgefield | Danbury | Silver Spring Golf Course - Silver Spring Golf Course |
| TUE 9/24 | 3:00 PM | League | Simsbury | Hall | Simsbury High School - Simsbury Farms CC |
| TUE 9/24 | 3:00 PM | League | New Britain | Rocky Hill, Glastonbury | Stanley Golf Course - Stanley Golf Course |
| TUE 9/24 | 3:00 PM | League | Brookfield | Newtown | Sunset Hill Golf Course - Sunset Hill Golf Course |
| TUE 9/24 | 3:00 PM | League | Berlin | Newington | Timberlin Golf Course - Timberlin Golf Course |
| TUE 9/24 | 3:00 PM | League | Northwest Catholic | Avon | Wampanoag Country Club - Wampanoag Country Club |
| TUE 9/24 | 3:00 PM | Practice | Shepaug Valley | | Lake Waramaug Country Club - Lake Waramaug Country Club |
| TUE 9/24 | 3:15 PM | Non-League | Weston | Staples | Weston High School - Aspetuck Country Club |
| TUE 9/24 | 3:30 PM | League | Norwalk | Fairfield Ludlowe | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 9/24 | 3:30 PM | League | Wilton | New Canaan | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 9/25 | 2:30 PM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| WED 9/25 | 3:00 PM | League | Bethel | Pomperaug | Bethel High School - Connecticut Country Club |
| WED 9/25 | 3:00 PM | League | Housatonic Regional | Northwestern | Canaan Country Club - Canaan Country Club |
| WED 9/25 | 3:00 PM | League | New Milford | Masuk | Candlewood Valley Country Club - Candlewood Valley Country Club |
| WED 9/25 | 3:00 PM | League | New Fairfield | Newtown | Club River Oaks - Club River Oaks |
| WED 9/25 | 3:00 PM | League | Westhill | Norwalk | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| WED 9/25 | 3:00 PM | League | Notre Dame Prep | Bunnell | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 9/25 | 3:00 PM | League | Newington | Conard | Indian Hill Country Club - Indian Hill Country Club |
| WED 9/25 | 3:00 PM | League | Rocky Hill | Berlin | Rocky Hill High School - Stanley Golf Course |
| WED 9/25 | 3:00 PM | League | Fairfield Warde | Wilton | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 9/25 | 3:00 PM | League | Stamford | New Canaan | Stamford High - Sterling Farms Golf Course |
| WED 9/25 | 3:00 PM | League | New Britain | Wethersfield | Stanley Golf Course - Stanley Golf Course |
| WED 9/25 | 3:00 PM | League | Shepaug Valley | Gilbert | Washington Club Golf Course - Washington Club Golf Course |
| WED 9/25 | 3:00 PM | Non-League | Glastonbury | Fairfield Prep | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| WED 9/25 | 3:15 PM | League | Staples | Darien | Longshore Golf Course - Longshore Golf Course |
| WED 9/25 | 3:15 PM | League | Brien McMahon | Trumbull | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 9/25 | 3:15 PM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| WED 9/25 | 3:30 PM | League | Nonnewaug | Lakeview | Crestbrook Park - Crestbrook Park Golf |
| THU 9/26 | 1:00 PM | League | Westhill | Stamford | Woodway Country Club - Woodway Country Club |
| THU 9/26 | 2:50 PM | League | Fairfield Ludlowe | Greenwich | Smith Richardson Golf Course - Smith Richardson Golf Course |
| THU 9/26 | 3:00 PM | League | Lewis Mills | Simsbury | Lewis Mills High School - Fairview Farm Golf Course |
| THU 9/26 | 3:00 PM | League | Hall | Southington | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 9/26 | 3:00 PM | League | Northwest Catholic | Conard | Wampanoag Country Club - Wampanoag Country Club |
| THU 9/26 | 3:00 PM | Non-League | CIAC | Brookfield, Danbury, Fairfield Prep, Lakeview, Immaculate, Joel Barlow, New Fairfield, Shepaug Valley, Rocky Hill, Pomperaug, Trumbull, Weston | [CIAC] Orange Hill GC - [CIAC] Orange Hill GC |
| THU 9/26 | 3:15 PM | League | Darien | Brien McMahon | Woodway Country Club - Woodway Country Club |
| FRI 9/27 | 3:15 PM | League | New Canaan | Staples | CCNC - CCNC |
| MON 9/30 | 3:00 PM | League | New Fairfield | Brookfield | Club River Oaks - Club River Oaks |
| MON 9/30 | 3:00 PM | League | Nonnewaug | Housatonic Regional | Crestbrook Park - Crestbrook Park Golf |
| MON 9/30 | 3:00 PM | League | Notre Dame Prep | Bethel | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| MON 9/30 | 3:00 PM | League | Wethersfield | Windsor | Goodwin Park Golf Course - Goodwin Park Golf Course |
| MON 9/30 | 3:00 PM | League | Gilbert | Northwestern | Green woods Country Club - Green woods Country Club |
| MON 9/30 | 3:00 PM | League | Ridgefield | Staples | Ridgefield Golf Course - Ridgefield Golf Course |
| MON 9/30 | 3:00 PM | Non-League | Newtown | Fairfield Prep | Rock Ridge Country Club - Rock Ridge Country Club |
| MON 9/30 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| MON 9/30 | 3:10 PM | League | St. Joseph | New Canaan, Norwalk | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| MON 9/30 | 3:15 PM | League | Weston | New Milford | Weston High School - Aspetuck Country Club |
| MON 9/30 | 3:30 PM | League | Greenwich | Darien | Round Hill Country Club - Round Hill Country Club |
| MON 9/30 | 3:30 PM | League | Shepaug Valley | Lakeview | Washington Club Golf Course - Washington Club Golf Course |
| MON 9/30 | 3:45 PM | League | Trumbull | Wilton | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| MON 9/30 | Postponed | League | Joel Barlow | Masuk | Redding Country Club - Redding Country Club |
| TUE 10/1 | 2:45 PM | League | Rocky Hill | Wethersfield | Rocky Hill High School - Stanley Golf Course |
| TUE 10/1 | 3:00 PM | League | Bunnell | Brookfield | Bunnell HS - Blackhawk Country Club (Old OCC) |
| TUE 10/1 | 3:00 PM | League | Housatonic Regional | Shepaug Valley | Canaan Country Club - Canaan Country Club |
| TUE 10/1 | 3:00 PM | League | Stratford | Joel Barlow | Mill River Country Club - Mill River Country Club |
| TUE 10/1 | 3:00 PM | League | Danbury | Trumbull | Richter Park Golf Course - Richter Park Golf Course |
| TUE 10/1 | 3:00 PM | League | Newtown | Pomperaug | Rock Ridge Country Club - Rock Ridge Country Club |
| TUE 10/1 | 3:00 PM | League | Conard | Lewis Mills | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| TUE 10/1 | 3:00 PM | League | Simsbury | Northwest Catholic | Simsbury High School - Simsbury Farms CC |
| TUE 10/1 | 3:00 PM | League | Southington | Avon | Southington High School - Southington Country Club |
| TUE 10/1 | 3:00 PM | League | New Britain | Berlin | Stanley Golf Course - Stanley Golf Course |
| TUE 10/1 | 3:00 PM | League | Farmington | Hall | Tunxis Country Club - Tunxis Country Club |
| TUE 10/1 | 3:00 PM | Non-League | Fairfield Warde | Fairfield Prep, Fairfield Ludlowe | CC of Fairfield - CC of Fairfield |
| TUE 10/1 | 3:10 PM | League | St. Joseph | Staples | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| TUE 10/1 | 3:15 PM | League | Brien McMahon | Stamford | Oak Hills Golf Course - Oak Hills Golf Course |
| TUE 10/1 | 3:15 PM | League | Weston | Immaculate | Weston High School - Aspetuck Country Club |
| TUE 10/1 | 3:15 PM | Non-League | Darien | Newington | Country Club of Darien - Country Club of Darien |
| TUE 10/1 | 3:30 PM | League | Northwestern | Lakeview | Northwestern Regional H.S. - Norfolk CC |
| WED 10/2 | 2:30 PM | League | Masuk | Joel Barlow, Notre Dame Prep | Whitney Farms Golf Course - Whitney Farms Golf Course |
| WED 10/2 | 2:45 PM | League | Avon | Farmington | Avon Country Club - Golf Club of Avon |
| WED 10/2 | 3:00 PM | League | New Canaan | Danbury | CCNC - CCNC |
| WED 10/2 | 3:00 PM | League | Brien McMahon | Westhill | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 10/2 | 3:00 PM | League | Newtown | New Milford | Rock Ridge Country Club - Rock Ridge Country Club |
| WED 10/2 | 3:00 PM | League | Hall | Rocky Hill | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| WED 10/2 | 3:00 PM | League | Southington | Conard | Southington High School - Southington Country Club |
| WED 10/2 | 3:00 PM | League | Wethersfield | Newington | Wethersfield Country Club - Wethersfield Country Club |
| WED 10/2 | 3:00 PM | Non-League | Fairfield Prep | Berlin | CC of Fairfield - CC of Fairfield |
| WED 10/2 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| WED 10/2 | 3:10 PM | League | St. Joseph | Stamford | Tashua Knolls Golf Course - Tashua Knolls Golf Course |
| WED 10/2 | 3:15 PM | League | Staples | Greenwich | Longshore Golf Course - Longshore Golf Course |
| WED 10/2 | 3:15 PM | League | Weston | New Fairfield | Weston High School - Aspetuck Country Club |
| WED 10/2 | 3:15 PM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| WED 10/2 | 3:30 PM | Non-League | Lewis Mills | Lakeview | Lewis Mills High School - Fairview Farm Golf Course |
| THU 10/3 | 11:00 AM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| THU 10/3 | 3:00 PM | League | Stratford | Weston | Mill River Country Club - Mill River Country Club |
| THU 10/3 | 3:00 PM | League | Northwestern | Nonnewaug | Northwestern Regional H.S. - Norfolk CC |
| THU 10/3 | 3:00 PM | Practice | Shepaug Valley | | Lake Waramaug Country Club - Lake Waramaug Country Club |
| THU 10/3 | 4:00 PM | League | Lakeview | Gilbert | Lakeview High School - Litchfield Country Club (LCC) |
| MON 10/7 | 3:00 PM | League | Housatonic Regional | Northwestern | Canaan Country Club - Canaan Country Club |
| MON 10/7 | 3:00 PM | League | Newington | Rocky Hill | Indian Hill Country Club - Indian Hill Country Club |
| MON 10/7 | 3:00 PM | League | Danbury | St. Joseph | Richter Park Golf Course - Richter Park Golf Course |
| MON 10/7 | 3:00 PM | League | Hall | Lewis Mills | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| MON 10/7 | 3:00 PM | League | Stamford | Norwalk | Stamford High - Sterling Farms Golf Course |
| MON 10/7 | 3:00 PM | League | Masuk | Bethel | Whitney Farms Golf Course - Whitney Farms Golf Course |
| MON 10/7 | 3:00 PM | Non-League | Shepaug Valley | Brookfield | Lake Waramaug Country Club - Lake Waramaug Country Club |
| MON 10/7 | 3:15 PM | League | Darien | New Canaan | Wee Burn CC - Wee Burn CC |
| MON 10/7 | Canceled | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| TUE 10/8 | 10:30 AM | Non-League | Avon | Brookfield, Conard, Berlin, Newington, Joel Barlow, Masuk, Lewis Mills, Glastonbury, Farmington, Pomperaug, New Milford, Southington, Simsbury, Wethersfield, Hall | Hop Meadow Country Club - Hop Meadow Country Club |
| TUE 10/8 | 2:30 PM | Non-League | Stamford | Brien McMahon | Stamford High - Sterling Farms Golf Course |
| TUE 10/8 | 3:00 PM | League | Westhill | Fairfield Warde | EG Brennan Golf Course - E Gaynor Brennan Golf Course |
| TUE 10/8 | 3:00 PM | League | Rocky Hill | New Britain | Rocky Hill High School - Stanley Golf Course |
| TUE 10/8 | 3:00 PM | Non-League | Fairfield Prep | Trumbull | Patterson Club - Patterson Club |
| TUE 10/8 | 3:00 PM | Practice | Shepaug Valley | | Lake Waramaug Country Club - Lake Waramaug Country Club |
| TUE 10/8 | 3:15 PM | League | Staples | Fairfield Ludlowe | Longshore Golf Course - Longshore Golf Course |
| TUE 10/8 | 3:15 PM | League | Weston | Notre Dame Prep | Weston High School - Aspetuck Country Club |
| TUE 10/8 | 3:30 PM | League | Wilton | Ridgefield | Rolling Hills Country Club - Rolling Hills Country Club |
| WED 10/9 | 2:50 PM | League | Fairfield Ludlowe | Westhill | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 10/9 | 3:00 PM | League | Notre Dame Prep | Newtown | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| WED 10/9 | 3:00 PM | League | Glastonbury | Newington | Glastonbury Hills Country Club - Glastonbury Hills Country Club |
| WED 10/9 | 3:00 PM | League | Pomperaug | New Fairfield | Pomperaug High School - Highfield Country Club |
| WED 10/9 | 3:00 PM | League | Joel Barlow | Bunnell | Redding Country Club - Redding Country Club |
| WED 10/9 | 3:00 PM | League | Simsbury | Southington | Simsbury High School - Simsbury Farms CC |
| WED 10/9 | 3:00 PM | League | Farmington | Northwest Catholic | Tunxis Country Club - Tunxis Country Club |
| WED 10/9 | 3:00 PM | League | Wethersfield | Conard, Avon | Wethersfield Country Club - Wethersfield Country Club |
| WED 10/9 | 3:00 PM | Non-League | Housatonic Regional | Mount Everett Regional High School MA | Canaan Country Club - Canaan Country Club |
| WED 10/9 | 3:00 PM | Non-League | Fairfield Prep | New Canaan | CC of Fairfield - CC of Fairfield |
| WED 10/9 | 3:00 PM | Non-League | Ridgefield | Immaculate | Silver Spring Golf Course - Silver Spring Golf Course |
| WED 10/9 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Range |
| WED 10/9 | 3:15 PM | Practice | Brookfield | | Sunset Hill Golf Course - Sunset Hill Golf Course |
| WED 10/9 | 3:30 PM | League | Norwalk | Brien McMahon | Oak Hills Golf Course - Oak Hills Golf Course |
| WED 10/9 | 3:30 PM | League | Wilton | St. Joseph | Rolling Hills Country Club - Rolling Hills Country Club |
| THU 10/10 | 12:01 AM | League | Staples | | Longshore Golf Course - Longshore Golf Course |
| THU 10/10 | 12:01 AM | League | St. Joseph | | TBA - TBA |
| THU 10/10 | 2:45 PM | League | Windsor | Berlin, Newington | Goodwin Park Golf Course - Goodwin Park Golf Course |
| THU 10/10 | 3:00 PM | League | Lewis Mills | Avon | Lewis Mills High School - Fairview Farm Golf Course |
| THU 10/10 | 3:00 PM | League | Conard | Hall | Rockledge Golf Club West Hartford - Rockledge Golf Club West Hartford |
| THU 10/10 | 3:00 PM | League | Northwest Catholic | Southington | Wampanoag Country Club - Wampanoag Country Club |
| THU 10/10 | 3:00 PM | Non-League | Stratford | Bunnell | Mill River Country Club - Mill River Country Club |
| FRI 10/11 | 3:00 PM | League | Farmington | Simsbury | Tunxis Country Club - Tunxis Country Club |
| MON 10/14 | 3:00 PM | League | Fairfield Warde | Norwalk | Brooklawn Country Club - Brooklawn Country Club |
| MON 10/14 | 3:00 PM | Scrimmage | Newtown | Joel Barlow | Rock Ridge Country Club - Rock Ridge Country Club |
| TUE 10/15 | 2:30 PM | Practice | Joel Barlow | | Redding Country Club - Redding Country Club |
| TUE 10/15 | 2:45 PM | League | Notre Dame Prep | Stratford | Fairchild Wheeler Golf Course - Fairchild Wheeler Golf Course |
| TUE 10/15 | 3:00 PM | League | Farmington | Avon, Newington | Farmington Country Club - Farmington Country Club |
| TUE 10/15 | 3:00 PM | League | Glastonbury | Rocky Hill, Windsor | Minnechaug Golf Course - Minnechaug Golf Course |
| TUE 10/15 | 3:00 PM | League | Immaculate | Bethel | Richter Park Golf Course - Richter Park Golf Course |
| TUE 10/15 | 3:15 PM | Postseason | Darien | | Country Club of Darien - Country Club of Darien |
| WED 10/16 | 2:50 PM | Non-League | Fairfield Ludlowe | Fairfield Prep | Smith Richardson Golf Course - Smith Richardson Golf Course |
| WED 10/16 | 3:00 PM | Practice | Danbury | | Richter Park Golf Course - Richter Park Golf Course |
| WED 10/16 | 3:00 PM | Practice | Shepaug Valley | | Washington Club Golf Course - Washington Club Golf Course |
| THU 10/17 | 9:00 AM | Postseason | Central Connecticut Conference (CCC) | Avon, Berlin, Conard, Farmington, Glastonbury, Newington, New Britain, Lewis Mills, Windsor, Hall, Wethersfield, Rocky Hill, Simsbury, Southington, Northwest Catholic | Stanley Golf Course - Stanley Golf Course |