| Date | Time | Type | Home School | Away School | Site |
| MON 9/11 | Canceled | League | | | Amity Middle School - Bethany - Field |
| THU 9/14 | 4:00 PM | League | | | Canton MS - Canton Middle School |
| THU 9/14 | Canceled | League | | | Amity Regional Junior High School-Orange - Soccer/Field Hockey Field |
| THU 9/14 | Postponed | League | | | Amity Middle School - Bethany - Field |
| MON 9/18 | 4:00 PM | League | Newtown | | Treadwell Park - Newtown Treadwell Park |
| MON 9/18 | Canceled | League | | | Litchfield High School - Softball Field |
| MON 9/18 | Postponed | League | | | Suffield Middle School - MS Field |
| TUE 9/19 | 3:45 PM | League | | | Branford High School - Walsh MS |
| TUE 9/19 | 3:45 PM | League | | | Eliot MS - Field Hockey Field |
| TUE 9/19 | 3:45 PM | League | | | Rochambeau Middle School - RMS Field Hockey Field |
| TUE 9/19 | 4:15 PM | League | | | Har-Bur Middle School - Field Hockey |
| TUE 9/19 | Canceled | League | | | Amity Regional Junior High School-Orange - Soccer/Field Hockey Field |
| WED 9/20 | 3:30 PM | League | | | Thomaston High School - Field Hockey Field |
| WED 9/20 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field Hockey Field |
| WED 9/20 | 4:00 PM | League | Bethel | | Bethel High School - Hunt Field at Bethel HS |
| WED 9/20 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| WED 9/20 | 4:00 PM | League | Newtown | | Treadwell Park - Newtown Treadwell Park |
| THU 9/21 | 3:45 PM | League | | | Polson MS - Polson Front Field |
| THU 9/21 | 3:45 PM | League | | | Walsh Intermediate School - WIS Back Field |
| THU 9/21 | 3:45 PM | League | | | Woodbury Middle School - Field Hockey Field |
| THU 9/21 | 4:00 PM | League | | | Canton MS - Canton Middle School |
| THU 9/21 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| THU 9/21 | Canceled | League | | | Thomaston High School - Field Hockey Field |
| FRI 9/22 | 3:45 PM | League | | | Dodd Middle School - Lower Field |
| FRI 9/22 | 3:45 PM | League | | | Woodbury Middle School - Field Hockey Field |
| FRI 9/22 | 4:00 PM | League | | JOHN F KENNEDY MIDDLE SCHOOL | Avery MS - MBA Field Hockey Grass Field |
| FRI 9/22 | 4:00 PM | League | | | Whisconier Middle School - WMS Field Hockey |
| FRI 9/22 | Postponed | League | | | Westbrook Middle School - Westbrook HS Field #2 - Soccer / Track |
| TUE 9/26 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| TUE 9/26 | 3:45 PM | League | | | Avery MS - MBA Field Hockey Grass Field |
| TUE 9/26 | 3:45 PM | League | | | Eliot MS - Field Hockey Field |
| TUE 9/26 | 4:00 PM | League | | | Granby Memorial High School - Pit Field |
| TUE 9/26 | 4:00 PM | League | | | Whisconier Middle School - WMS Field Hockey |
| TUE 9/26 | Canceled | League | | | Wamogo MS - Middle school Field Hockey Field |
| TUE 9/26 | Postponed | League | | | Adams Middle School - Baseball Field |
| WED 9/27 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| THU 9/28 | 3:45 PM | League | | | Branford High School - Walsh MS |
| THU 9/28 | 3:45 PM | League | | | Canton MS - Turf Field |
| THU 9/28 | 3:45 PM | League | | | Eliot MS - Field Hockey Field |
| THU 9/28 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field Hockey Field |
| THU 9/28 | 3:45 PM | League | | | North Branford Intermediate School - Jerome Elementary School |
| THU 9/28 | 3:45 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| THU 9/28 | 3:45 PM | League | | | Woodbury Middle School - Field Hockey Field |
| THU 9/28 | 4:00 PM | League | | | Granby Memorial High School - Pit Field |
| THU 9/28 | 4:00 PM | League | | | Irving Robbins Middle School - |
| THU 9/28 | 4:00 PM | League | | | Whisconier Middle School - WMS Field Hockey |
| FRI 9/29 | Postponed | League | | | Bethel Middle School - Hunt Field |
| FRI 9/29 | Postponed | League | | | Har-Bur Middle School - Field Hockey |
| MON 10/2 | 3:30 PM | League | | | Swift Middle School - Swift MS |
| MON 10/2 | 3:45 PM | League | | | Adams Middle School - Baseball Field |
| MON 10/2 | 3:45 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| MON 10/2 | 4:00 PM | League | | | Avery MS - MBA Field Hockey Grass Field |
| MON 10/2 | 4:00 PM | League | | | Granby Memorial High School - Pit Field |
| MON 10/2 | 4:00 PM | League | Newtown | | Treadwell Park - Newtown Treadwell Park |
| MON 10/2 | Canceled | League | | | Irving Robbins Middle School - 20 Wolf Pit Rd., Farmington CT 06032 |
| TUE 10/3 | 3:45 PM | League | | | Adams Middle School - Baseball Field |
| TUE 10/3 | 3:45 PM | League | | | Polson MS - Polson Front Field |
| TUE 10/3 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| TUE 10/3 | 4:00 PM | League | | | Rochambeau Middle School - RMS Field Hockey Field |
| TUE 10/3 | Canceled | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| WED 10/4 | 3:45 PM | League | | | Henry James Memorial School |
| WED 10/4 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Field Hockey Field |
| WED 10/4 | 3:45 PM | League | | | Shepaug Valley High School - Shepaug Valley Middle School Field Hockey Field |
| WED 10/4 | 4:00 PM | League | | | Bethel Middle School - Hunt Field |
| WED 10/4 | Canceled | Non-League | | | Walsh Intermediate School - WIS Back Field |
| THU 10/5 | 3:45 PM | League | | | Branford High School - Walsh MS |
| THU 10/5 | 3:45 PM | League | | | Canton MS - Canton Middle School |
| THU 10/5 | 3:45 PM | League | | | Dodd Middle School - Lower Field |
| THU 10/5 | 3:45 PM | League | | | Irving Robbins Middle School - 20 Wolf Pit Rd., Farmington CT 06032 |
| THU 10/5 | 3:45 PM | League | | | North Branford Intermediate School - Jerome Elementary School |
| THU 10/5 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| THU 10/5 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| THU 10/5 | 3:45 PM | League | | | Woodbury Middle School - Field Hockey Field |
| THU 10/5 | 4:00 PM | League | | | Memorial Middle School - MMS Field Hockey Field |
| THU 10/5 | 4:00 PM | League | | | Rochambeau Middle School - RMS Field Hockey Field |
| FRI 10/6 | 3:30 PM | League | | | Thomaston High School - Field Hockey Field |
| FRI 10/6 | 4:00 PM | League | | | Granby Memorial High School - Pit Field |
| FRI 10/6 | Canceled | League | | | Amity Regional Junior High School-Orange - Soccer/Field Hockey Field |
| TUE 10/10 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| TUE 10/10 | 3:45 PM | League | | | Adams Middle School - Baseball Field |
| TUE 10/10 | 3:45 PM | League | | | Branford High School - Walsh MS |
| TUE 10/10 | 3:45 PM | League | | | Memorial Middle School - MMS Field Hockey Field |
| TUE 10/10 | 4:00 PM | League | | | Bethel Middle School - Hunt Field |
| TUE 10/10 | Canceled | League | | | Eliot MS - Field Hockey Field |
| TUE 10/10 | Canceled | League | | | Wamogo MS - Middle school Field Hockey Field |
| WED 10/11 | 3:45 PM | League | | | Har-Bur Middle School - Field Hockey |
| WED 10/11 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Field Hockey Field |
| WED 10/11 | 3:45 PM | League | | | Shepaug Valley High School - Shepaug Valley Middle School Field Hockey Field |
| WED 10/11 | 4:00 PM | League | | | Amity Middle School - Bethany - Field |
| WED 10/11 | 4:00 PM | League | | | Bethel Middle School - Hunt Field |
| WED 10/11 | 4:00 PM | League | | | Rochambeau Middle School - RMS Field Hockey Field |
| WED 10/11 | 4:00 PM | League | | | Stafford Middle School - Front field |
| THU 10/12 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| THU 10/12 | 3:45 PM | League | | | Eliot MS - Field Hockey Field |
| THU 10/12 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field Hockey Field |
| THU 10/12 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| THU 10/12 | 3:45 PM | Non-League | | | Branford High School - Walsh MS |
| THU 10/12 | 4:00 PM | League | | | Shepaug Valley High School - Shepaug Valley Middle School Field Hockey Field |
| THU 10/12 | 4:20 PM | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| THU 10/12 | Canceled | League | | | Amity Regional Junior High School-Orange - Soccer/Field Hockey Field |
| THU 10/12 | Canceled | League | | | Wamogo MS - Middle school Field Hockey Field |
| FRI 10/13 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| FRI 10/13 | 3:30 PM | League | | | Thomaston High School - Field Hockey Field |
| FRI 10/13 | 3:45 PM | League | | | Canton MS - Canton Middle School |
| FRI 10/13 | 3:45 PM | League | | | Memorial Middle School - MMS Field Hockey Field |
| FRI 10/13 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| MON 10/16 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| MON 10/16 | 3:45 PM | League | | | Swift Middle School - Swift MS |
| MON 10/16 | 4:00 PM | League | | | Amity Middle School - Bethany - Field |
| MON 10/16 | 4:00 PM | League | | | Granby Memorial High School - Pit Field |
| MON 10/16 | 4:00 PM | League | | | Henry James Memorial School |
| MON 10/16 | 4:00 PM | League | Newtown | | Treadwell Park - Newtown Treadwell Park |
| MON 10/16 | 4:00 PM | League | | | Whisconier Middle School - WMS Field Hockey |
| TUE 10/17 | 3:45 PM | League | | | Adams Middle School - Baseball Field |
| TUE 10/17 | 3:45 PM | League | | | Eliot MS - Field Hockey Field |
| TUE 10/17 | 3:45 PM | League | | | Henry James Memorial School |
| TUE 10/17 | 3:45 PM | League | | | North Branford Intermediate School - Jerome Elementary School |
| TUE 10/17 | 4:00 PM | League | | | Whisconier Middle School - WMS Field Hockey |
| WED 10/18 | 3:30 PM | League | | | Irving Robbins Middle School - 20 Wolf Pit Rd., Farmington CT 06032 |
| WED 10/18 | 3:30 PM | League | | | Swift Middle School - Swift MS |
| WED 10/18 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Field Hockey Field |
| WED 10/18 | 3:45 PM | League | | | Kingswood-Oxford School |
| WED 10/18 | Canceled | League | | | Woodbury Middle School - Field Hockey Field |
| THU 10/19 | 3:30 PM | League | | | Har-Bur Middle School - Field Hockey |
| THU 10/19 | 3:45 PM | League | | | Branford High School - Walsh MS |
| THU 10/19 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field Hockey Field |
| THU 10/19 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Field Hockey Field |
| THU 10/19 | 3:45 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| THU 10/19 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| THU 10/19 | 4:00 PM | League | | | Memorial Middle School - MMS Field Hockey Field |
| THU 10/19 | Canceled | League | | | Amity Regional High School - Field Hockey Field |
| THU 10/19 | Canceled | League | | | Har-Bur Middle School - Field Hockey |
| FRI 10/20 | 3:30 PM | League | | | Thomaston High School - Field Hockey Field |
| FRI 10/20 | Canceled | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| MON 10/23 | 3:45 PM | League | | | Rochambeau Middle School - RMS Field Hockey Field |
| MON 10/23 | 3:45 PM | League | | | Shepaug Valley High School - Shepaug Valley Middle School Field Hockey Field |
| MON 10/23 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| MON 10/23 | 4:00 PM | League | | | Bethel Middle School - Hunt Field |
| MON 10/23 | 4:00 PM | League | | | Granby Memorial High School - Pit Field |
| MON 10/23 | 4:00 PM | League | | | Irving Robbins Middle School - 20 Wolf Pit Rd., Farmington CT 06032 |
| TUE 10/24 | 3:45 PM | League | | | Polson MS - Polson Front Field |
| TUE 10/24 | 3:45 PM | League | | | Swift Middle School - Swift MS |
| TUE 10/24 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| TUE 10/24 | 4:00 PM | League | | | Whisconier Middle School - WMS Field Hockey |
| TUE 10/24 | Canceled | League | | | Branford High School - Walsh MS |
| WED 10/25 | 3:30 PM | League | | | LITCHFIELD MIDDLE SCHOOL - Soccer Field |
| WED 10/25 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #6 - Baseball / Field Hockey |
| WED 10/25 | 4:00 PM | League | | | Avery MS - MBA Field Hockey Grass Field |
| WED 10/25 | 4:00 PM | League | | | Stafford Middle School - Front field |
| WED 10/25 | Canceled | League | | | Northwestern Regional M.S. - Field Hockey Field |
| THU 10/26 | 3:45 PM | League | | | Har-Bur Middle School - Field Hockey |
| THU 10/26 | 3:45 PM | League | | | Polson MS - Polson Front Field |
| THU 10/26 | 4:00 PM | League | | | Dodd Middle School - Lower Field |
| THU 10/26 | 4:00 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| THU 10/26 | Canceled | League | | | Litchfield High School - Softball Field |
| FRI 10/27 | 3:30 PM | Non-League | Newtown | | Treadwell Park - Newtown Treadwell Park |
| FRI 10/27 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field Hockey Field |
| FRI 10/27 | 4:00 PM | League | | | Bethel Middle School - Hunt Field |
| FRI 10/27 | 4:00 PM | League | | | Rochambeau Middle School - RMS Field Hockey Field |
| FRI 10/27 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| FRI 10/27 | 4:00 PM | League | | | Thomaston High School - Field Hockey Field |
| FRI 10/27 | Canceled | League | | | Thomaston High School - Field Hockey Field |
| MON 10/30 | 3:45 PM | League | | | Dodd Middle School - Lower Field |
| MON 10/30 | Canceled | League | | , | Irving Robbins Middle School - 20 Wolf Pit Rd., Farmington CT 06032 |
| MON 10/30 | Canceled | League | | | Northwestern Regional M.S. - Field Hockey Field |
| MON 10/30 | Postponed | League | | | Memorial Middle School - MMS Field Hockey Field |
| MON 10/30 | Postponed | League | | | Shepaug Valley High School - Shepaug Valley Middle School Field Hockey Field |
| WED 11/1 | 3:45 PM | League | | | North Branford Intermediate School - Jerome Elementary School |
| WED 11/1 | 3:45 PM | League | | | Rochambeau Middle School - RMS Field Hockey Field |
| WED 11/1 | 4:00 PM | League | | | Amity Middle School - Bethany - Field |
| WED 11/1 | Canceled | League | | | Irving Robbins Middle School - 20 Wolf Pit Rd., Farmington CT 06032 |
| THU 11/2 | 3:45 PM | League | | | Woodbury Middle School - Field Hockey Field |
| THU 11/2 | 4:00 PM | League | | | Dodd Middle School - Lower Field |
| FRI 11/3 | 3:30 PM | League | | | Shepaug Valley High School - Shepaug Valley Middle School Field Hockey Field |
| FRI 11/3 | 4:00 PM | League | | | Memorial Middle School - MMS Field Hockey Field |