| Date | Time | Type | Home School | Away School | Site |
| TUE 9/3 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 9/3 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| TUE 9/3 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 9/4 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| WED 9/4 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| WED 9/4 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| THU 9/5 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| THU 9/5 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| THU 9/5 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| FRI 9/6 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| FRI 9/6 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| MON 9/9 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| MON 9/9 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| MON 9/9 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| TUE 9/10 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 9/10 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| TUE 9/10 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| TUE 9/10 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 9/11 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| WED 9/11 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| WED 9/11 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 9/11 | 3:45 PM | League | Capt. Nathan Hale School | Stafford MS | Captain Nathan Hale School - Soccer field |
| WED 9/11 | 3:45 PM | League | Mansfield MS | Hall Memorial School, Horace Porter School | Mansfield Middle School - MMS CC Course |
| WED 9/11 | 3:45 PM | League | Windham MS | Stem Academy, Barrow STEM Magnet | Windham MS - Default Facility |
| WED 9/11 | Canceled | League | Bolton Center School | Lebanon MS | Bolton Center Middle School - BCS Cross Country Course |
| THU 9/12 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| THU 9/12 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| THU 9/12 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| THU 9/12 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| FRI 9/13 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| MON 9/16 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| MON 9/16 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| MON 9/16 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| MON 9/16 | 3:30 PM | League | Northwestern MS | Gilbert MS | Northwestern Regional M.S. - Track |
| TUE 9/17 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 9/17 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| TUE 9/17 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| WED 9/18 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| WED 9/18 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 9/18 | 3:45 PM | League | Hall Memorial School | Capt. Nathan Hale School | Hall Memorial School - Default Facility |
| WED 9/18 | 3:45 PM | League | Eli Terry Junior Middle School | Dag Hammarskjold School, Gilbert MS | Harry S. Fisher Elementary School - Lower Fisher |
| WED 9/18 | 3:45 PM | League | Lyme-Old Lyme MS | Nathan Hale Ray MS | Lyme-Old Lyme Middle School - MS Cross Country Course |
| WED 9/18 | 3:45 PM | League | Mansfield MS | Stem Academy, Barrow STEM Magnet | Mansfield Middle School - MMS CC Course |
| WED 9/18 | 3:45 PM | League | Shepaug Valley MS | Thomaston MS | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| WED 9/18 | 4:00 PM | League | North Branford Intermediate | John Winthrop Middle School, Eliot MS | North Branford Intermediate School - Totoket Park |
| WED 9/18 | 4:00 PM | League | Old Saybrook MS | Strong MS | Old Saybrook Middle School - Old Saybrook MS Campus |
| WED 9/18 | 4:00 PM | League | Portland MS | Haddam-Killingworth MS | Portland MS - PHS Track |
| THU 9/19 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| THU 9/19 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| THU 9/19 | 3:30 PM | League | Comp Sci MS | Aerospace/Engineering - Windsor, East Windsor MS, Innovation MS, International MS | Academy of Computer Science and Engineering Middle - Cross Country Course |
| THU 9/19 | 3:30 PM | League | Putnam MS | Plainfield Central School | St. Marie Greenhalgh Sports Complex - Nature Trail |
| THU 9/19 | 3:45 PM | League | Brooklyn MS | Preston Plains School, Woodstock MS | Brooklyn Middle School - Prince Hill |
| THU 9/19 | 3:45 PM | League | Killingly Intermediate | Griswold MS | Killingly Intermediate School - KIS East Field (Side of School) |
| FRI 9/20 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| FRI 9/20 | 3:45 PM | League | Plumb Hill MS | Woodbury MS, Shepaug Valley MS | White Memorial Conservation Center - White Memorial Conservation Center |
| FRI 9/20 | 4:00 PM | League | Derby MS | Seymour MS | Derby MS - Derby MS |
| MON 9/23 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| MON 9/23 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| MON 9/23 | 3:30 PM | League | Woodbury MS | Thomaston MS | Woodbury Middle School - WMS XC Course |
| MON 9/23 | 3:45 PM | League | Eli Terry Junior Middle School | Northwestern MS | Harry S. Fisher Elementary School - Lower Fisher |
| MON 9/23 | 3:45 PM | League | Shepaug Valley MS | Region One Regional MS | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| TUE 9/24 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 9/24 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| TUE 9/24 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| TUE 9/24 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 9/25 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| WED 9/25 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 9/25 | 3:45 PM | League | Capt. Nathan Hale School | Avery MS, Bolton Center School | Captain Nathan Hale School - Soccer field |
| WED 9/25 | 3:45 PM | League | Eli Terry Junior Middle School | Woodbury MS | Eli Terry Jr. Middle School - Upper Track (Fisher Elementary) |
| WED 9/25 | 3:45 PM | League | Strong MS | Portland MS, North Branford Intermediate | Frank Ward Strong Middle School - Alyn Brook Park (Pickett Lane) |
| WED 9/25 | 3:45 PM | League | Haddam-Killingworth MS | Lyme-Old Lyme MS | Haddam Killingworth Middle School - Cross Country Course |
| WED 9/25 | 3:45 PM | League | Eliot MS | Old Saybrook MS | Indian River Complex - XC Course |
| WED 9/25 | 3:45 PM | League | John Winthrop Middle School | Nathan Hale Ray MS | John Winthrop Middle School - John Winthrop Middle School |
| WED 9/25 | 3:45 PM | League | Shepaug Valley MS | Schaghticoke MS | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| WED 9/25 | 3:45 PM | League | Stafford MS | Hall Memorial School | Stafford MS - Near front field |
| WED 9/25 | 4:00 PM | League | Rochambeau MS | Memorial MS-Middlebury | Rochambeau Middle School - Rochambeau Cross Country Course |
| WED 9/25 | 4:00 PM | League | Vernon Center MS | Edwards MS, Illing MS | Vernon Center Middle School - VCMS Fields |
| THU 9/26 | 3:30 PM | League | Ashford MS | Baldwin MS Canterbury | Ashford Middle School - Ashford Memorial Park |
| THU 9/26 | 3:30 PM | League | Comp Sci MS | East Windsor MS, Aerospace/Engineering - Windsor, Innovation MS, International MS | Elizabeth Park - Cross Country Course |
| THU 9/26 | 3:30 PM | League | Plainfield Central School | Griswold MS | Plainfield Central Middle School - Plainfield Central Middle School |
| THU 9/26 | 3:30 PM | League | Pomfret Community School | Wheeler High /MS | Pomfret Community School - Gym 1 |
| THU 9/26 | 3:45 PM | League | Brooklyn MS | Killingly Intermediate | Brooklyn Middle School - Prince Hill |
| THU 9/26 | 3:45 PM | League | Parish Hill MS | Thompson MS, Rectory School | Parish Hill Middle School - cross country course |
| THU 9/26 | 4:00 PM | League | Whisconier MS | Newtown MS, Schaghticoke MS | Whisconier Middle School - WMS Front Field |
| FRI 9/27 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| FRI 9/27 | 3:45 PM | League | Mansfield MS | Windham MS | Mansfield Middle School - MMS CC Course |
| FRI 9/27 | 4:00 PM | League | Woodstock MS | Putnam MS | Woodstock Middle School - Baseball Field |
| MON 9/30 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| MON 9/30 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| MON 9/30 | 3:45 PM | League | Gilbert MS | Region One Regional MS | Gilbert School - Football Field |
| MON 9/30 | 4:00 PM | Non-League | Wheeler High /MS | St. Bernard MS, St. Bernard MS | TBA - TBA |
| TUE 10/1 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 10/1 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| TUE 10/1 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| TUE 10/1 | 3:45 PM | League | Schaghticoke MS | Bethel MS | Schaghticoke MS - Schaghticoke MS |
| TUE 10/1 | 4:00 PM | League | Schaghticoke MS | Whisconier MS | Schaghticoke MS |
| WED 10/2 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| WED 10/2 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| WED 10/2 | 3:15 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 10/2 | 3:30 PM | League | Northwestern MS | Canton MS | Northwestern Regional M.S. - Track |
| WED 10/2 | 3:45 PM | League | Bolton Center School | Stafford MS | Bolton Center Middle School - BCS Cross Country Course |
| WED 10/2 | 3:45 PM | League | Hall Memorial School | Mansfield MS | Hall Memorial School - Default Facility |
| WED 10/2 | 3:45 PM | League | Lyme-Old Lyme MS | Strong MS | Lyme-Old Lyme Middle School - MS Cross Country Course |
| WED 10/2 | 3:45 PM | League | Barrow STEM Magnet | Stem Academy, Horace Porter School | Stem Academy - Softball Field |
| WED 10/2 | 3:45 PM | League | Stem Academy | Horace Porter School, Barrow STEM Magnet | Stem Academy - Softball Field |
| WED 10/2 | 3:45 PM | League | Plumb Hill MS | Eli Terry Junior Middle School | White Memorial Conservation Center - White Memorial Conservation Center |
| WED 10/2 | 3:45 PM | League | Windham MS | Lebanon MS, Capt. Nathan Hale School | Windham MS - Default Facility |
| WED 10/2 | 4:00 PM | League | Portland MS | Nathan Hale Ray MS, Old Saybrook MS | Portland MS - PHS Track |
| THU 10/3 | 12:01 AM | League | Ashford MS | Parish Hill MS | ASHFORD SCHOOL - Ashford Memorial Park |
| THU 10/3 | 3:30 PM | League | Thompson MS | Eastford Elementary | Thompson Middle School - TMS Soccer Field |
| THU 10/3 | 3:30 PM | Non-League | East Windsor MS | Aerospace/Engineering - Windsor, Comp Sci MS, International MS, Innovation MS | East Windsor Resevoir - East Windsor Resevoir |
| THU 10/3 | 3:45 PM | League | Thomaston MS | Shepaug Valley MS | Black Rock State Park - Black Rock State Park |
| THU 10/3 | 3:45 PM | League | Griswold MS | Brooklyn MS | Griswold Middle School - Default Facility |
| THU 10/3 | 3:45 PM | League | Killingly Intermediate | Putnam MS | Killingly Intermediate School - KIS East Field (Side of School) |
| THU 10/3 | 3:45 PM | League | Wheeler High /MS | Baldwin MS Canterbury | Wheeler Middle High School - MHS XC Course |
| THU 10/3 | 4:00 PM | League | Vernon Center MS | Tolland MS | Vernon Center Middle School - VCMS Fields |
| THU 10/3 | 4:00 PM | League | Woodstock MS | Plainfield Central School | Woodstock Middle School - Baseball Field |
| FRI 10/4 | 3:45 PM | League | Haddam-Killingworth MS | Nathan Hale Ray MS, John Winthrop Middle School | Haddam Killingworth Middle School - Cross Country Course |
| FRI 10/4 | 3:45 PM | League | Memorial MS-Middlebury | Woodbury MS | Memorial Middle School - Memorial Cross Country Course |
| MON 10/7 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| MON 10/7 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| MON 10/7 | 3:30 PM | League | Northwestern MS | Eli Terry Junior Middle School | Northwestern Regional M.S. - Track |
| MON 10/7 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| MON 10/7 | 3:45 PM | League | Gilbert MS | Thomaston MS | Gilbert School - Football Field |
| MON 10/7 | 4:30 PM | League | Region One Regional MS | Mount Everett Regional High School MA | Housatonic Valley Regional High - Secondary Cross Country Start |
| TUE 10/8 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 10/8 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| TUE 10/8 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| TUE 10/8 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| TUE 10/8 | 3:45 PM | League | Strong MS | John Winthrop Middle School | Frank Ward Strong Middle School - Alyn Brook Park (Pickett Lane) |
| TUE 10/8 | 3:45 PM | Non-League | Memorial MS-Middlebury | Long River MS | Memorial Middle School - Memorial Cross Country Course |
| WED 10/9 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| WED 10/9 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| WED 10/9 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 10/9 | 3:45 PM | League | Bolton Center School | Capt. Nathan Hale School, Mansfield MS | Bolton Center Middle School - BCS Cross Country Course |
| WED 10/9 | 3:45 PM | League | Hall Memorial School | Lebanon MS | Hall Memorial School - Default Facility |
| WED 10/9 | 3:45 PM | League | Eliot MS | Portland MS | Indian River Complex - XC Course |
| WED 10/9 | 3:45 PM | League | Old Saybrook MS | Lyme-Old Lyme MS, Haddam-Killingworth MS | Old Saybrook Middle School - Old Saybrook High School |
| WED 10/9 | 3:45 PM | League | Plumb Hill MS | Schaghticoke MS | Plumb Hill Field Complex - Plumb Hill Track |
| WED 10/9 | 3:45 PM | League | Stafford MS | Horace Porter School, Granby Memorial MS | Stafford MS - Near front field |
| WED 10/9 | 3:45 PM | League | Washington Montessori | Region One Regional MS | Washington Montessori |
| WED 10/9 | 3:45 PM | League | Woodbury MS | Eli Terry Junior Middle School | Woodbury Middle School - WMS XC Course |
| WED 10/9 | 4:00 PM | League | New Fairfield MS | Whisconier MS | New Fairfield Middle School - Track |
| WED 10/9 | 4:00 PM | League | Woodstock MS | Griswold MS | Woodstock Middle School - Baseball Field |
| WED 10/9 | Postponed | League | Gilbert MS | Northwestern MS | Gilbert School - Football Field |
| THU 10/10 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| THU 10/10 | 3:30 PM | League | Comp Sci MS | Aerospace/Engineering - Windsor, East Windsor MS, Innovation MS, International MS | East Windsor Resevoir - East Windsor Resevoir |
| THU 10/10 | 3:30 PM | League | Parish Hill MS | Wheeler High /MS, Eastford Elementary | Parish Hill Middle School - cross county course |
| THU 10/10 | 3:30 PM | League | Plainfield Central School | Killingly Intermediate | Plainfield Central Middle School - Plainfield Central Middle School |
| THU 10/10 | 3:45 PM | League | Thomaston MS | Har-Bur MS | Black Rock State Park - Black Rock State Park |
| THU 10/10 | 3:45 PM | League | Putnam MS | Brooklyn MS | St. Marie Greenhalgh Sports Complex - Nature Trail |
| FRI 10/11 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| FRI 10/11 | 3:45 PM | League | Shepaug Valley MS | Woodbury MS | Shepaug Valley High School - Shepaug Valley Middle & High School Cross Country Course |
| FRI 10/11 | 4:00 PM | League | Avery MS | Tolland MS | Avery MS - MBA XC Course |
| MON 10/14 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 10/15 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| TUE 10/15 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| TUE 10/15 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| TUE 10/15 | 4:00 PM | League | Memorial MS-Middlebury | Rochambeau MS | Memorial Middle School - Memorial Cross Country Course |
| TUE 10/15 | 4:00 PM | League | Nathan Hale Ray MS | Strong MS, Eliot MS | Nathan Hale Ray MS - Nathan Hale Ray MS |
| TUE 10/15 | 4:00 PM | Non-League | Vernon Center MS | St. James - Manchester | Vernon Center Middle School - VCMS Fields |
| TUE 10/15 | 4:30 PM | League | Region One Regional MS | Shepaug Valley MS | Housatonic Valley Regional High - Secondary Cross Country Start |
| WED 10/16 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| WED 10/16 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| WED 10/16 | 3:45 PM | League | Thomaston MS | Woodbury MS, Eli Terry Junior Middle School | Black Rock State Park - Black Rock State Park |
| WED 10/16 | 3:45 PM | League | Capt. Nathan Hale School | Barrow STEM Magnet, Stem Academy | Captain Nathan Hale School - Soccer field |
| WED 10/16 | 3:45 PM | League | Griswold MS | Putnam MS | Griswold Middle School - GMS XC Course |
| WED 10/16 | 3:45 PM | League | Haddam-Killingworth MS | North Branford Intermediate | Haddam Killingworth Middle School - Cross Country Course |
| WED 10/16 | 3:45 PM | League | John Winthrop Middle School | Old Saybrook MS | John Winthrop Middle School - John Winthrop Middle School |
| WED 10/16 | 3:45 PM | League | Lebanon MS | Bolton Center School, Hall Memorial School | Lebanon MS - LMS/Lyman XC Course |
| WED 10/16 | 3:45 PM | League | Lyme-Old Lyme MS | Portland MS | Lyme-Old Lyme Middle School - MS Cross Country Course |
| WED 10/16 | 3:45 PM | League | Stafford MS | Mansfield MS, Avery MS | Stafford MS - Near front field |
| WED 10/16 | 4:00 PM | League | Northwestern MS | Plumb Hill MS | Northwestern Regional M.S. - Track |
| THU 10/17 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| THU 10/17 | 3:30 PM | League | Comp Sci MS | Aerospace/Engineering - Windsor, Innovation MS | Elizabeth Park - Cross Country Course |
| THU 10/17 | 3:30 PM | League | Parish Hill MS | St. James - Danielson, Baldwin MS Canterbury | Parish Hill Middle School - cross country course |
| THU 10/17 | 3:30 PM | League | Thompson MS | Ashford MS | Thompson Middle School - TMS Soccer Field |
| THU 10/17 | 3:45 PM | League | Brooklyn MS | Plainfield Central School | Brooklyn Middle School - Prince Hill |
| THU 10/17 | 3:45 PM | League | Killingly Intermediate | Woodstock MS | Killingly Intermediate School - KIS East Field (Side of School) |
| THU 10/17 | 4:00 PM | League | Whisconier MS | New Fairfield MS, Schaghticoke MS, Bethel MS | Whisconier Middle School - WMS Front Field |
| FRI 10/18 | 3:30 PM | League | Northwestern MS | Thomaston MS | Northwestern Regional M.S. - Track |
| FRI 10/18 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| FRI 10/18 | 4:00 PM | League | Indian Mountain School | Region One Regional MS | Indian Mountain School |
| MON 10/21 | 2:30 PM | Practice | Griswold MS | | Griswold Middle School - GMS XC Course |
| MON 10/21 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| MON 10/21 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| MON 10/21 | 3:45 PM | League | Thomaston MS | Gilbert MS | Black Rock State Park - Black Rock State Park |
| MON 10/21 | 3:45 PM | League | Plumb Hill MS | Northwestern MS | White Memorial Conservation Center - White Memorial Conservation Center |
| TUE 10/22 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| TUE 10/22 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| TUE 10/22 | 3:30 PM | Practice | Wheeler High /MS | | Wheeler Middle High School - MHS XC Course |
| TUE 10/22 | 3:45 PM | League | Avery MS | Stafford MS | Avery MS - MBA XC Course |
| WED 10/23 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| WED 10/23 | 3:00 PM | League | Plainfield Central School | Brooklyn MS, Ashford MS, Baldwin MS Canterbury, Griswold MS, Eastford Elementary, Killingly Intermediate, Pomfret Community School, Putnam MS, Parish Hill MS, Rectory School, Woodstock MS, Thompson MS, St. James - Danielson, Wheeler High /MS | Plainfield High School - QVJC Championships XC |
| WED 10/23 | 3:45 PM | League | Thomaston MS | Northwestern MS | Black Rock State Park - Black Rock State Park |
| WED 10/23 | 4:00 PM | League | Newtown MS | Whisconier MS | Newtown MS - Reed intermediate School |
| WED 10/23 | 4:00 PM | League | Old Saybrook MS | John Winthrop Middle School, Strong MS, North Branford Intermediate, Melillo MS, Nathan Hale Ray MS, Portland MS, Lyme-Old Lyme MS, Haddam-Killingworth MS, Eliot MS | Old Saybrook High School - Old Saybrook Campus |
| THU 10/24 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| THU 10/24 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| THU 10/24 | 3:30 PM | Non-League | East Windsor MS | Aerospace/Engineering - Windsor, International MS, Innovation MS, Comp Sci MS | Academy of Computer Science and Engineering Middle - Cross Country Course |
| THU 10/24 | 4:00 PM | League | Lebanon MS | Windham MS, Barrow STEM Magnet, Stafford MS, Stem Academy, Capt. Nathan Hale School, Bolton Center School, Hall Memorial School, Horace Porter School, Mansfield MS | Lebanon MS |
| FRI 10/25 | 3:45 PM | League | Memorial MS-Middlebury | Dodd MS | Memorial Middle School - Memorial Cross Country Course |
| FRI 10/25 | 4:30 PM | League | Region One Regional MS | Gilbert MS | Housatonic Valley Regional High - Secondary Cross Country Start |
| MON 10/28 | 3:30 PM | League | Woodbury MS | Shepaug Valley MS | Woodbury Middle School - WMS XC Course |
| MON 10/28 | 4:00 PM | League | Har-Bur MS | Plumb Hill MS | Har-Bur Middle School - Har-Bur Cross Country |
| TUE 10/29 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |
| TUE 10/29 | 3:30 PM | League | Comp Sci MS | Aerospace/Engineering - Windsor, Innovation MS, International MS | Academy of Computer Science and Engineering Middle - Cross Country Course |
| TUE 10/29 | 3:45 PM | League | Avery MS | Suffield MS | Avery MS - MBA XC Course |
| TUE 10/29 | Canceled | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| WED 10/30 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| WED 10/30 | 3:45 PM | League | Woodbury MS | Thomaston MS, Memorial MS-Middlebury | Woodbury Middle School - WMS XC Course |
| THU 10/31 | 2:30 PM | Practice | Shepaug Valley MS | | Shepaug Valley High School - MS Cross Country Course |
| THU 10/31 | 3:00 PM | Practice | Whisconier MS | | Whisconier Middle School - C.C. & Track - Boys |