| Thomaston 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 468 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Mon., 8/29 | V Boys Soccer | Seymour (Scrim.) | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 8/30 | V Girls Soccer | Holy Cross (Scrim.) | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | V Field Hockey | Lewis Mills (Scrim.) | Home - Thomaston HS-Field Hockey Field [Directions] | 3:30 p.m. | ||
| Fri., 9/2 | V Girls Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Sat., 9/3 | V Boys Soccer | TBA | Away - Wolcott HS-Monroe Field | 10:00 a.m. | ||
| Tue., 9/6 | V Boys Cross Country | BL Cross Country Scrimmage | Home - Black Rock State Park [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 9/7 | ||||||
| Tue., 9/6 | V Girls Cross Country | BL Cross Country Scrimmage | Home - Black Rock State Park [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 9/7 | ||||||
| Tue., 9/6 | V Girls Soccer | Wolcott (Scrim.) | Away - Wolcott HS-Monroe Field [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 9/8 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 9/8 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | Postponed | ||
| Thu., 9/8 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 9/8 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 9/8 | V Girls Soccer | Nonnewaug | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 2-1 | |
| Thu., 9/8 | JV Girls Soccer | Nonnewaug | Home - Highwood Farms Field-Highwoods field [Directions] | 3:45 p.m. | ||
| Sat., 9/10 | V Boys Soccer | Northwestern | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 9:30 a.m. | W 4-3 | |
| Sat., 9/10 | V Girls Soccer | Northwestern | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 11:15 a.m. | W 3-0 | |
| Tue., 9/13 | V Boys Cross Country | Housatonic Regional, Shepaug Valley | Home - Black Rock State Park [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 9/13 | JV Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Tue., 9/13 | V Girls Cross Country | Housatonic Regional, Shepaug Valley | Home - Black Rock State Park [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | L 2-4 | |
| Tue., 9/13 | JV Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 9/13 | JV Girls Soccer | Wamogo | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Postponed | ||
| Wed., 9/14 | V Field Hockey | Northwestern | Home - Thomaston HS-Field Hockey Field [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 9/14 | JV Field Hockey | Northwestern | Home - Thomaston HS-Field Hockey Field [Directions] | 5:00 p.m. | W 1-0 | |
| Thu., 9/15 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 9/15 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 9/16 | V Field Hockey | Litchfield | Home - Thomaston HS-Gym [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/16 | JV Field Hockey | Litchfield | Home - Thomaston HS-Gym [Directions] | 5:00 p.m. | L 0-1 | |
| Fri., 9/16 | V Girls Soccer | Litchfield | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | W 10-2 | |
| Sat., 9/17 | V Boys Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 9:00 a.m. | ||
| Sat., 9/17 | JV Boys Soccer | Litchfield | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/17 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | Postponed | ||
| Mon., 9/19 | V Boys Soccer | Housatonic Regional | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | W 6-1 | |
| Mon., 9/19 | JV Boys Soccer | Housatonic Regional | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Mon., 9/19 | V Field Hockey | Watertown | Home - Thomaston HS-Gym [Directions] | 3:45 p.m. | T 1-1 | |
| Mon., 9/19 | JV Field Hockey | Watertown | Home - Thomaston HS-Gym [Directions] | 5:00 p.m. | L 0-1 | |
| Mon., 9/19 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 9/19 | JV Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | Postponed | ||
| Wed., 9/21 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Wed., 9/21 | V Girls Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Fri., 9/23 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 9/23 | V Field Hockey | Shepaug Valley | Home - Thomaston HS-Gym [Directions] | 3:45 p.m. | OT-L 1-2 | |
| Fri., 9/23 | JV Field Hockey | Shepaug Valley | Home - Thomaston HS-Gym [Directions] | 5:00 p.m. | T 0-0 | |
| Fri., 9/23 | V Girls Soccer | Shepaug Valley | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | W 6-0 | |
| Sat., 9/24 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/24 | JV Girls Soccer | Shepaug Valley | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 9:00 a.m. | ||
| Tue., 9/27 | V Boys Cross Country | Terryville, Nonnewaug | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Soccer | Litchfield | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 1-8 | |
| Tue., 9/27 | V Girls Cross Country | Terryville, Nonnewaug | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 9/27 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 5:00 p.m. | W 1-0 | |
| Tue., 9/27 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 9/29 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 8-0 | |
| Thu., 9/29 | V Girls Soccer | Gilbert | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | W 11-1 | |
| Fri., 9/30 | JV Girls Soccer | Gilbert | Home - Highwood Farms Field-Nystrom Park Field [Directions] | 3:45 p.m. | ||
| Sat., 10/1 | JV Boys Soccer | Wamogo | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Postponed | ||
| Sat., 10/1 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Tue., 10/4 | V Boys Cross Country | Gilbert, Wamogo | Home - Black Rock State Park [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Soccer | Nonnewaug | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 1-2 | |
| Tue., 10/4 | V Girls Cross Country | Gilbert, Wamogo | Home - Thomaston HS-Black Rock State Park [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Field Hockey | Nonnewaug | Home - Thomaston HS-Field Hockey Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/4 | JV Field Hockey | Nonnewaug | Home - Thomaston HS-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:00 p.m. | L 4-0 | |
| Thu., 10/6 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:15 p.m. | W 2-0 | |
| Fri., 10/7 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/7 | JV Boys Soccer | Terryville | Away - Terryville HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 10/8 | JV Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | JV Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | 10:00 a.m. | ||
| Tue., 10/11 | V Boys Cross Country | Litchfield, Northwestern | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Boys Soccer | Wamogo | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | W 8-1 | |
| Tue., 10/11 | JV Boys Soccer | Wamogo | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Tue., 10/11 | V Girls Cross Country | Litchfield, Northwestern | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Field Hockey | Wamogo | Home - Thomaston HS-Field Hockey Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 10/11 | JV Field Hockey | Wamogo | Home - Thomaston HS-Field Hockey Field [Directions] | 5:00 p.m. | L 1-2 | |
| Tue., 10/11 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 10/11 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Sat., 10/15 | JV Boys Soccer | Nonnewaug, Lewis Mills, Watertown | Away - Nonnewaug HS-Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | Postponed | ||
| Mon., 10/17 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 5:30 p.m. | W 3-2 | |
| Mon., 10/17 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/18 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | W 4-2 | |
| Tue., 10/18 | V Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | L 0-1 | |
| Tue., 10/18 | JV Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | T 0-0 | |
| Tue., 10/18 | V Girls Soccer | Housatonic Regional | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | T 3-3 | |
| Wed., 10/19 | V Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | L 0-5 | |
| Wed., 10/19 | JV Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | L 0-4 | |
| Thu., 10/20 | V Boys Cross Country | BL Championship | Home - Black Rock State Park [Directions] | 3:30 p.m. | ||
| Thu., 10/20 | V Girls Cross Country | BL XC Championship | Home - Black Rock State Park [Directions] | 4:15 p.m. | ||
| Sat., 10/22 | JV Field Hockey | Nonnewaug, Shepaug Valley, Watertown | Away - Nonnewaug HS-Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Golf | CIAC Division II Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Tue., 10/25 | V Boys Soccer | Shepaug Valley | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 1-7 | |
| Tue., 10/25 | JV Boys Soccer | Shepaug Valley | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Wed., 10/26 | V Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 3:45 p.m. | L 1-3 | |
| Wed., 10/26 | JV Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | T 0-0 | |
| Wed., 10/26 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | W 9-0 | |
| Fri., 10/28 | JV Boys Soccer | Terryville | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Fri., 10/28 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Fri., 10/28 | JV Girls Soccer | Housatonic Regional | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park | 11:55 a.m. | ||
| Sat., 10/29 | V Boys Soccer | Terryville | Home - Thomaston Nystrom Park [Directions] | 7:30 p.m. | L 0-1 | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park | 11:20 a.m. | ||
| Sat., 10/29 | V Girls Soccer | Terryville | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 6:00 p.m. | W 2-0 | |
| Mon., 10/31 | V Boys Soccer | Gilbert | Home - Thomaston Nystrom Park [Directions] | 3:45 p.m. | W 8-1 | |
| Mon., 10/31 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 6-0 | |
| Wed., 11/2 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 3-1 | |
| Wed., 11/2 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | L 0-1 | |
| Wed., 11/2 | V Girls Soccer | Northwestern | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:00 p.m. | W 1-0 | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | JV Boys Soccer | Wamogo (Scrim.) | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/4 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | L 3-1 | |
| Mon., 11/7 | V Boys Soccer | Montville | Away - Montville HS-Montville Turf Field [Directions] | 5:00 p.m. | W 2-0 | |
| Mon., 11/7 | V Field Hockey | Northwest Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:00 p.m. | ||
| Wed., 11/9 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 2:00 p.m. | L 0-5 | |
| Thu., 11/10 | V Girls Soccer | Canton | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 11/12 | V Girls Soccer | St. Paul Catholic | Home - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 2:00 p.m. | W 2-1 | |
| Wed., 11/16 | V Girls Soccer | East Catholic | Away - Falcon Field (Meriden, CT)-Football Field [Directions] | 5:00 p.m. | ||
| Mon., 11/28 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8-9:30 p.m. | ||
| Tue., 11/29 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Wed., 11/30 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | ||
| Thu., 12/1 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 12/2 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Fri., 12/2 | V Girls Basketball | Bristol Central (Scrim.) | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 6:30 p.m. | ||
| Mon., 12/5 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8-9:30 p.m. | ||
| Tue., 12/6 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Tue., 12/6 | V Girls Basketball | Bristol Central, Woodland (Scrim.) | Home - Thomaston HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/7 | V Boys Ice Hockey | Newtown/New Fairfield (Scrim.) | Away - Danbury Ice Arena-Patriot Rink [Directions] | 4:30 p.m. | ||
| Thu., 12/8 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 12/9 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8-9:30 p.m. | ||
| Sat., 12/10 | V Boys Basketball | Watertown (Scrim.) | Home - Thomaston HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/10 | V Wrestling | Bristol Eastern, Avon, Berlin, Farmington, TBA, New Britain, Simsbury, St. Paul Catholic, Wethersfield | Away - Bristol Eastern HS-Gym | 9:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 12/12 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8-9:30 p.m. | ||
| Tue., 12/13 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8-9:30 p.m. | ||
| Tue., 12/13 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 35-36 | |
| Tue., 12/13 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 1-5 | |
| Wed., 12/14 | V Wrestling | St. Paul Catholic | Home - Terryville HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/15 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 12/16 | V Boys Ice Hockey | Byram Hills (NY) | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:00 p.m. | L 6-7(OT) | |
| Sat., 12/17 | V Wrestling | Blue Devil Duals | Away - Plainville HS-Wood Gymnasium | 10:00 a.m. | ||
| Mon., 12/19 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Tue., 12/20 | V Boys Basketball | Wamogo | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 43-57 | |
| Tue., 12/20 | JV Boys Basketball | Wamogo | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School-NHL | 7:15 p.m. | W 4-0 | |
| Tue., 12/20 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 43-14 | |
| Tue., 12/20 | JV Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/21 | V Boys Basketball | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:30 p.m. | L 36-41 | |
| Wed., 12/21 | JV Boys Basketball | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Thu., 12/22 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 12/23 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | Canceled | Cancelled | |
| Mon., 12/26 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Tue., 12/27 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 6:30 p.m. | L 29-38 | |
| Tue., 12/27 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:30-8 p.m. | ||
| Tue., 12/27 | V Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:00 p.m. | L 29-43 | |
| Wed., 12/28 | V Boys Basketball | East Hampton | Away - Litchfield HS [Directions] | 5:00 p.m. | L 58-72 | |
| Wed., 12/28 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 4:10 p.m. | L 3-9 | |
| Wed., 12/28 | V Wrestling | Nonnewaug | Home - Terryville HS-Gym [Directions] | 1:00 p.m. | ||
| Wed., 12/28 | V Girls Basketball | Barrington (RI) | Home - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:00 p.m. | L 45-50 | |
| Thu., 12/29 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:30-8 p.m. | ||
| Fri., 12/30 | V Boys Ice Hockey | Milford Coop | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:30 p.m. | W 7-0 | |
| Fri., 12/30 | V Girls Basketball | Litchfield | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | W 49-13 | |
| Fri., 12/30 | JV Girls Basketball | Litchfield | Home - Thomaston HS-Gym [Directions] | Canceled | Cancelled | |
| Mon., 1/2 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Tue., 1/3 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Brookfield | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 49-43 | |
| Tue., 1/3 | JV Girls Basketball | Brookfield | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Basketball | Gilbert | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 50-45 | |
| Wed., 1/4 | JV Boys Basketball | Gilbert | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | JV Boys Basketball | Gilbert | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Housatonic Coop | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | W 6-0 | |
| Wed., 1/4 | V Wrestling | Derby/Oxford/Holy Cross | Home - Terryville HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 1/5 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Thu., 1/5 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 4:15 p.m. | ||
| Thu., 1/5 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | W 45-11 | |
| Thu., 1/5 | JV Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | W 53-42 | |
| Fri., 1/6 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Ice Hockey | Masuk | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | L 2-7 | |
| Sat., 1/7 | JV Boys Ice Hockey | JBWA | Home - The Frederick Gunn School-Ice Rink [Directions] | 10:00 a.m. | ||
| Sat., 1/7 | V Wrestling | Warrior Invitational | Away - Canton HS-Gym | 9:30 a.m. | ||
| Mon., 1/9 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:30-9 p.m. | ||
| Tue., 1/10 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | L 39-62 | |
| Tue., 1/10 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/10 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Nonnewaug | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 38-35 | |
| Tue., 1/10 | JV Girls Basketball | Nonnewaug | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Pawling (NY) | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:30 p.m. | L 2-6 | |
| Wed., 1/11 | V Girls Basketball | Windsor Locks | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 45-30 | |
| Wed., 1/11 | JV Girls Basketball | Windsor Locks | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | V Boys Basketball | Windsor Locks | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 46-69 | |
| Thu., 1/12 | JV Boys Basketball | Windsor Locks | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | Canceled | Cancelled | |
| Fri., 1/13 | V Boys Basketball | Shepaug Valley | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 78-47 | |
| Fri., 1/13 | JV Boys Basketball | Shepaug Valley | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | V Boys Ice Hockey | Mt. Everett (MA) | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | W 6-0 | |
| Fri., 1/13 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 57-17 | |
| Fri., 1/13 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:30-9 p.m. | ||
| Tue., 1/17 | V Boys Basketball | Housatonic Regional | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 62-25 | |
| Tue., 1/17 | JV Boys Basketball | Housatonic Regional | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | W 67-26 | |
| Tue., 1/17 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/18 | V Boys Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 6:45 p.m. | W 77-50 | |
| Wed., 1/18 | JV Boys Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 6:30 p.m. | W 2-1 OT | |
| Wed., 1/18 | V Wrestling | Northwestern | Away - Northwestern Regional H.S.-Small Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/19 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 57-64 | |
| Fri., 1/20 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Boys Ice Hockey | JBWA | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | L 1-4 | |
| Fri., 1/20 | V Girls Basketball | Northwestern | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 59-41 | |
| Fri., 1/20 | JV Girls Basketball | Northwestern | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 11:45 a.m.-12:45 p.m. | ||
| Sat., 1/21 | V Wrestling | New Milford Wrestling Tournament | Away - New Milford HS-Small Gym - NMHS | 8:00 a.m. | ||
| Tue., 1/24 | V Boys Basketball | Litchfield | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 46-51 | |
| Tue., 1/24 | JV Boys Basketball | Litchfield | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:15-9:45 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 64-17 | |
| Tue., 1/24 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/25 | V Wrestling | Gilbert/Torrington | Away - Gilbert School-Gym [Directions] | Postponed | ||
| Thu., 1/26 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Thu., 1/26 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:30 p.m. | W 56-47 | |
| Thu., 1/26 | JV Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 41-55 | |
| Fri., 1/27 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Wamogo | Home - Thomaston HS-Gym [Directions] | 7:30 p.m. | W 63-18 | |
| Fri., 1/27 | JV Girls Basketball | Wamogo | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/28 | FR Boys Basketball | Northwestern | Home - Thomaston HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/28 | V Wrestling | Portland, Avon, Bristol Eastern, Coventry, Daniel Hand, Griswold/Wheeler, Haddam-Killingworth, Old Lyme, Manchester, Morgan, TBA, New Britain, Nonnewaug, Plainville | Away - . | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Portland HS-PHS Gym | ||||||
| Sat., 1/28 | V Wrestling | Suffield/Windsor Locks, Hampden Charter (MA), Hampden Charter (MA), Ludlow (MA), TBA, TBA, Northwestern, Rockville, Sabis (MA), South Windsor, Stafford | Away - Suffield HS | 9:30 a.m. | ||
| Mon., 1/30 | V Boys Ice Hockey | Pawling (NY) | Away - Trinity-Pawling School-Ice Rink | 7:15 p.m. | L 2-6 | |
| Tue., 1/31 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:30 p.m. | L 43-59 | |
| Tue., 1/31 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/31 | JV Boys Ice Hockey | Forman School | Away - Rumsey Hall School-Ice Rink | 7:15 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Gilbert | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 46-29 | |
| Tue., 1/31 | JV Girls Basketball | Gilbert | Home - Thomaston HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/1 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:30-9 p.m. | ||
| Wed., 2/1 | V Wrestling | Gilbert/Torrington, St. Paul Catholic | Away - Gilbert School-Gym [Directions] | 7:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 6:00 p.m. | ||||||
| Thu., 2/2 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:15-9:45 p.m. | ||
| Thu., 2/2 | JV Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:15 p.m. | ||
| Sat., 2/4 | V Wrestling | 2023 Bacon Academy Matt Bishel Bobcat Classic | Away - Bacon Academy | 9:00 a.m. | ||
| Mon., 2/6 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:30-8 p.m. | ||
| Tue., 2/7 | V Boys Basketball | Nonnewaug | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 56-70 | |
| Tue., 2/7 | JV Boys Basketball | Nonnewaug | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | W 41-35 | |
| Tue., 2/7 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | SCW Knights | Away - Cromwell-Upper Rink [Directions] | 4:20 p.m. | L 3-4 OT | |
| Thu., 2/9 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:15-9:45 p.m. | ||
| Thu., 2/9 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/9 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Terryville | Home - Thomaston HS-Gym [Directions] | 7:30 p.m. | W 68-42 | |
| Fri., 2/10 | JV Boys Basketball | Terryville | Home - Thomaston HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/10 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Terryville | Home - Thomaston HS-Gym [Directions] | 6:00 p.m. | W 54-18 | |
| Fri., 2/10 | JV Girls Basketball | Terryville | Home - Thomaston HS-Gym [Directions] | 3:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:05 p.m. | ||||||
| Sat., 2/11 | FR Boys Basketball | Watertown | Home - Thomaston HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/11 | V Wrestling | BVL Wrestling Championships | Away - Derby HS-DHS Vitello Gym | 9:00 a.m. | ||
| Sun., 2/12 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 12-1 p.m. | ||
| Mon., 2/13 | V Boys Ice Hockey | Housatonic Coop | Away - South Kent School-Ice Rink [Directions] | 3:45 p.m. | W 2-1 | |
| Mon., 2/13 | V Girls Basketball | Shepaug Valley | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 57-14 | |
| Mon., 2/13 | JV Girls Basketball | Shepaug Valley | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 52-53 | |
| Tue., 2/14 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | ||
| Wed., 2/15 | V Girls Basketball | Housatonic Regional | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 60-15 | |
| Wed., 2/15 | JV Girls Basketball | Housatonic Regional | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/16 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | W 76-49 | |
| Thu., 2/16 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/16 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 3:15 p.m. | W 6-5 | |
| Fri., 2/17 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | W 3-2 | |
| Fri., 2/17 | V Wrestling | CIAC S Championship | Away - Killingly | 4:00 p.m. | ||
| Fri., 2/17 | V Girls Basketball | Terryville | Home - Thomaston HS-Gym [Directions] | 5:30 p.m. | W 70-17 | |
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC S Championship | Away - Killingly | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Tue., 2/21 | V Boys Ice Hockey | New Milford | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:15 p.m. | L 1-7 | |
| Tue., 2/21 | JV Boys Ice Hockey | New Milford | Home - The Frederick Gunn School-Ice Rink [Directions] | Canceled | Cancelled | |
| Tue., 2/21 | V Girls Basketball | Gilbert | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | W 50-44 | |
| Wed., 2/22 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | Canceled | Cancelled | |
| Thu., 2/23 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:15-9:45 p.m. | ||
| Thu., 2/23 | JV Boys Ice Hockey | Forman School | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:15 p.m. | ||
| Fri., 2/24 | V Boys Basketball | Northwestern | Home - Thomaston HS-Gym [Directions] | 5:00 p.m. | L 62-66 | |
| Fri., 2/24 | JV Boys Basketball | Northwestern | Home - Thomaston HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/24 | V Boys Ice Hockey | Newtown/New Fairfield | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | W 3-0 | |
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Fri., 2/24 | V Girls Basketball | Northwestern | Home - Terryville HS-Gym [Directions] | 7:00 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:20 p.m. | W 4-2 | |
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/27 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/28 | FR Boys Basketball | Litchfield | Home - Wamogo Regional HS-Small Gym [Directions] | Postponed | ||
| Tue., 2/28 | JV Boys Ice Hockey | JBWA | Home - The Frederick Gunn School-Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 3/1 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | L 1-8 | |
| Wed., 3/1 | V Girls Basketball | Hale Ray | Home - Thomaston HS-Gym [Directions] | 6:30 p.m. | W 49-12 | |
| Thu., 3/2 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 9:00 p.m. | W 4-0 | |
| Fri., 3/3 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 3:30-5 p.m. | ||
| Fri., 3/3 | V Girls Basketball | Westbrook | Home - Thomaston HS-Gym [Directions] | 3:30 p.m. | W 51-17 | |
| Sun., 3/5 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 1-2 p.m. | ||
| Mon., 3/6 | V Boys Ice Hockey | Hall | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:00 p.m. | L 3-6 | |
| Wed., 3/8 | V Girls Basketball | Northwest Catholic | Home - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 67-34 | |
| Fri., 3/24 | V Boys Lacrosse | Lewis Mills (Scrim.) | Home - Nonnewaug HS-football field [Directions] | 5:30 p.m. | ||
| Fri., 3/24 | V Softball | Lewis Mills (Scrim.) | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 3/28 | V Baseball | Wilby (Scrim.) | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | ||
| Thu., 3/30 | V Boys Lacrosse | Wilbur Cross (Scrim.) | Away - Bowen Field-Football Field [Directions] | 6:00 p.m. | ||
| Sat., 4/1 | JV Baseball | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Sat., 4/1 | V Boys Lacrosse | Bristol Coop | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 12:00 p.m. | L 4-8 | |
| Sat., 4/1 | V Girls Lacrosse | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 11:00 a.m. | L 3-13 | |
| Sat., 4/1 | JV Girls Lacrosse | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 12:30 p.m. | ||
| Mon., 4/3 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | L 12-2 | |
| Mon., 4/3 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 4/3 | V Softball | Shepaug Valley | Home - Thomaston HS-Softball Field [Directions] | 3:45 p.m. | L 8-0 | |
| Mon., 4/3 | V Girls Tennis | Shepaug Valley | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Tue., 4/4 | V Baseball | Wamogo | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 5-2 | |
| Tue., 4/4 | V Boys Outdoor Track | Kangaroo Invitational | Away - Terryville HS-Track | 3:45 p.m. | ||
| Tue., 4/4 | V Girls Outdoor Track | Kangaroo Invitational | Away - Terryville HS-Track | 3:45 p.m. | ||
| Tue., 4/4 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 8-6 | |
| Wed., 4/5 | V Boys Lacrosse | Watertown | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 3-15 | |
| Wed., 4/5 | JV Boys Lacrosse | Watertown | Home - Plumb Hill Field Complex-Softball Field [Directions] | 5:15 p.m. | ||
| Wed., 4/5 | V Boys Tennis | Litchfield | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 4/5 | V Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 8-12 | |
| Wed., 4/5 | JV Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:30 p.m. | ||
| Wed., 4/5 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Thu., 4/6 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 8-5 | |
| Sat., 4/8 | V Boys Lacrosse | Ellington | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 11:00 a.m. | L 2-10 | |
| Sat., 4/8 | JV Boys Lacrosse | Ellington | Home - Plumb Hill Field Complex-Softball Field [Directions] | 12:15 p.m. | ||
| Sat., 4/8 | V Softball | Brookfield | Home - Thomaston HS-Baseball/Softball Field [Directions] | 11:00 a.m. | L 12-1 | |
| Tue., 4/11 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:00 p.m. | L 7-17 | |
| Tue., 4/11 | JV Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:30 p.m. | ||
| Tue., 4/11 | JV Girls Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 4/11 | V Softball | Watertown | Away - Watertown High-Softball Field [Directions] | 3:45 p.m. | L 8-4 | |
| Wed., 4/12 | V Baseball | Terryville | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 12-1 | |
| Thu., 4/13 | V Boys Lacrosse | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 2:00 p.m. | L 4-9 | |
| Thu., 4/13 | JV Boys Lacrosse | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 3:45 p.m. | ||
| Fri., 4/14 | V Baseball | East Granby | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | L 18-8 | |
| Sat., 4/15 | V Baseball | Lewis Mills | Away - Lewis Mills HS-Baseball Field - Varsity [Directions] | 12:00 p.m. | L 10-0 | |
| Mon., 4/17 | V Boys Lacrosse | Capital Prep | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | W 15-1 | |
| Mon., 4/17 | JV Boys Lacrosse | Capital Prep | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 4/17 | V Softball | Northwestern | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | W 9-8 | |
| Tue., 4/18 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | L 15-1 | |
| Tue., 4/18 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Tue., 4/18 | V Girls Tennis | Northwestern | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Wed., 4/19 | V Baseball | Housatonic Regional | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | W 10 - 0 | |
| Wed., 4/19 | V Boys Lacrosse | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 3-18 | |
| Wed., 4/19 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Wed., 4/19 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | W 10-2 | |
| Wed., 4/19 | V Girls Tennis | Nonnewaug | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Fri., 4/21 | V Boys Tennis | Wamogo | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Fri., 4/21 | V Girls Lacrosse | Housatonic Regional | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 9-6 | |
| Fri., 4/21 | JV Girls Lacrosse | Housatonic Regional | Home - Plumb Hill Field Complex-Softball Field [Directions] | Postponed | ||
| Fri., 4/21 | V Softball | Lewis Mills | Away - Lewis Mills HS-Softball Varsity Field [Directions] | 3:45 p.m. | L 7-6 | |
| Fri., 4/21 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Sat., 4/22 | V Girls Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 4:30 p.m. | L 6-7 (OT) | |
| Mon., 4/24 | V Baseball | Gilbert | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 13 - 8 | |
| Mon., 4/24 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 5:30 p.m. | W 17-10 | |
| Mon., 4/24 | V Boys Tennis | Housatonic Regional | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Mon., 4/24 | V Girls Lacrosse | Wolcott | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | L 7-9 | |
| Mon., 4/24 | JV Girls Lacrosse | Wolcott | Home - Nonnewaug HS-Turf Field [Directions] | 6:30 p.m. | ||
| Mon., 4/24 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 3:45 p.m. | W 22-1 | |
| Tue., 4/25 | V Boys Outdoor Track | Housatonic Regional, Wamogo | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Outdoor Track | Housatonic Regional | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Wed., 4/26 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | L 11 - 1 | |
| Wed., 4/26 | V Softball | Nonnewaug | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | W 5-4 | |
| Wed., 4/26 | V Girls Tennis | Gilbert | Away - Gilbert School-PineWoods Racquet Club [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/28 | V Baseball | Shepaug Valley | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 15 - 1 | |
| Fri., 4/28 | V Boys Tennis | Shepaug Valley | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/28 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 3:45 p.m. | L 4-3 | |
| Fri., 4/28 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Sat., 4/29 | V Boys Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Sat., 4/29 | V Girls Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Mon., 5/1 | V Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 13 - 3 | |
| Mon., 5/1 | V Boys Lacrosse | Tolland | Home - Nonnewaug HS-Turf Field [Directions] | 5:30 p.m. | L 6-7 | |
| Mon., 5/1 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 5/1 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:45 p.m. | L 4-13 | |
| Mon., 5/1 | V Softball | Wamogo/Litchfield | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:20 p.m. | W 4-2 | |
| Mon., 5/1 | V Girls Tennis | Litchfield | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:15 p.m. | L 0-7 [Detailed Results] | |
| Tue., 5/2 | V Boys Outdoor Track | Nonnewaug, Northwestern | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Nonnewaug, Northwestern | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Girls Lacrosse | Rocky Hill | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | L 3-8 | |
| Wed., 5/3 | JV Girls Lacrosse | Rocky Hill | Home - Nonnewaug HS-Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 5/3 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 5/4 | V Baseball | Litchfield | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 24 - 5 | |
| Fri., 5/5 | V Boys Tennis | Nonnewaug | Home - Thomaston HS [Directions] | 3:45 p.m. | L 0-5 | |
| Sat., 5/6 | V Baseball | Canton | Home - Thomaston HS-Baseball/Softball Field [Directions] | 2:00 p.m. | L 17 - 2 | |
| Sat., 5/6 | V Boys Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 11-12 | |
| Sat., 5/6 | JV Boys Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Softball Field [Directions] | 5:15 p.m. | ||
| Sat., 5/6 | V Boys Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Mon., 5/8 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | W 7 - 5 | |
| Mon., 5/8 | V Boys Lacrosse | Holy Cross | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | L 6-15 | |
| Mon., 5/8 | JV Boys Lacrosse | Holy Cross | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/8 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 5/8 | V Softball | Terryville | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | W 15-0 | |
| Mon., 5/8 | V Girls Tennis | Wamogo | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 5/9 | V Boys Outdoor Track | Terryville, Shepaug Valley | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Lacrosse | Housatonic Regional | Away - Housatonic Valley Regional High-football field [Directions] | 6:15 p.m. | W 9-6 | |
| Tue., 5/9 | V Girls Outdoor Track | Terryville, Shepaug Valley | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 5/10 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | 3:45 p.m. | W 16-1 | |
| Wed., 5/10 | V Girls Tennis | Housatonic Regional | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:30 p.m. | L 3-4 [Detailed Results] | |
| Thu., 5/11 | V Baseball | Northwestern | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 10-0 | |
| Thu., 5/11 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:30 p.m. | L 4-18 | |
| Thu., 5/11 | V Boys Tennis | Gilbert | Home - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 5/11 | V Girls Lacrosse | Watertown | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 5:00 p.m. | L 4-15 | |
| Thu., 5/11 | JV Girls Lacrosse | Watertown | Home - Plumb Hill Field Complex-Softball Field [Directions] | Postponed | ||
| Thu., 5/11 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | L 21-13 | |
| Thu., 5/11 | V Girls Tennis | Gilbert | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/15 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | W 6-3 | |
| Mon., 5/15 | V Boys Outdoor Track | Litchfield, Gilbert | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Girls Outdoor Track | Litchfield, Gilbert | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Softball | Housatonic Regional | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:15 p.m. | W 8-0 | |
| Tue., 5/16 | V Boys Tennis | Northwestern | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 1-4 | |
| Tue., 5/16 | V Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 5:15 p.m. | L 4-19 | |
| Tue., 5/16 | JV Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Softball | Watertown | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 14-0 | |
| Tue., 5/16 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - TBA | 8:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Wed., 5/17 | V Boys Lacrosse | Wolcott | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 5:30 p.m. | W 17-7 | |
| Wed., 5/17 | JV Boys Lacrosse | Wolcott | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/17 | V Boys Tennis | Berkshire League Boys Tennis Tournament | Away - TBA | 8:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Wed., 5/17 | V Girls Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | L 9-10 | |
| Thu., 5/18 | V Baseball | Granby Memorial | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | L 20-4 | |
| Thu., 5/18 | V Girls Tennis | East Granby | Away - East Granby HS-EGHS Tennis Courts [Directions] | 4:30 p.m. | L 3-4 | |
| Fri., 5/19 | V Baseball | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 5/19 | V Softball | Gilbert | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | W 20-5 | |
| Sat., 5/20 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 9:00 a.m. | ||
| Sat., 5/20 | V Boys Outdoor Track | Berkshire League Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 5/20 | V Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 11:00 a.m. | ||
| Sat., 5/20 | V Girls Outdoor Track | Berkshire League Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Mon., 5/22 | V Baseball | Nonnewaug | Home - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 25-1 | |
| Mon., 5/22 | V Boys Lacrosse | Capital Prep (Scrim.) | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 5/22 | V Boys Tennis | Berkshire League Boys Tennis Tournament Semi & Finals | Away - TBA | 1:00 p.m. | ||
| Mon., 5/22 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:15 p.m. | W 2-0 | |
| Mon., 5/22 | V Girls Tennis | Berkshire League Girls Tennis Tournament Semi & Finals | Away - TBA | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Tue., 5/23 | V Boys Outdoor Track | Berkshire League Festival Steeplechase Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Home - Thomaston HS-Nystrom Park [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | V Girls Outdoor Track | Berkshire League Festival Steeplechase Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 5/24 | V Boys Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Housatonic Valley Regional High-Track | 3:30 p.m. | ||
| Wed., 5/24 | V Girls Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Housatonic Valley Regional High-Track | 3:30 p.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class S Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Softball | Somers | Home - Thomaston HS-Baseball/Softball Field [Directions] | 4:00 p.m. | W 6-5 | |
| Wed., 5/31 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 4:00 p.m. | L 2-0 | |
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||