| Litchfield 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 472 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Mon., 8/30 | V Boys Golf | Wamogo, Gilbert | Away - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | 182 | |
| Wed., 9/1 | V Girls Soccer | Canton (Scrim.) | Away - Canton HS-Canton H.S. Turf [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 9/2 | V Football | Woodland (Scrim.) | Home - Nonnewaug HS-football field [Directions] | 6:00 p.m. | ||
| Fri., 9/3 | V Boys Soccer | TBA, Jonathan Law, Masuk, Montville, Northwestern, Old Saybrook, Wilton | Away - Not Listed-Kelley Martin Tighe Memorial Field | 4:00 p.m. | ||
| Sat., 9/4 | V Boys Soccer | Lewis Mills (Scrim.) | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 10:00 a.m. | ||
| Tue., 9/7 | V Boys Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Tue., 9/7 | V Girls Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Tue., 9/7 | V Girls Soccer | New Fairfield (Scrim.) | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:15 p.m. | ||
| Tue., 9/7 | JV Girls Soccer | New Fairfield (Scrim.) | Away - New Fairfield HS-Marty Morgan Field [Directions] | Canceled | Cancelled | |
| Wed., 9/8 | V Boys Golf | Nonnewaug | Home - Litchfield Country Club [Directions] | 3:00 p.m. | 190 | |
| Thu., 9/9 | V Boys Golf | Housatonic Regional | Away - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Thu., 9/9 | V Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | L 0-8 | |
| Thu., 9/9 | JV Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Fri., 9/10 | V Football | Platt Tech | Away - Foran Turf Field [Directions] | 7:00 p.m. | W 26-14 | |
| Mon., 9/13 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 11-0 | |
| Mon., 9/13 | V Girls Soccer | Gilbert | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 6-2 | |
| Tue., 9/14 | V Boys Cross Country | Gilbert, Thomaston | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Soccer | Shepaug Valley | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 2-1 ot | |
| Tue., 9/14 | JV Boys Soccer | Shepaug Valley | Home - Plumb Hill Field Complex-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Gilbert, Thomaston | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-2 | |
| Wed., 9/15 | V Boys Golf | Housatonic Regional | Home - Litchfield Country Club [Directions] | 3:00 p.m. | 179 | |
| Thu., 9/16 | V Boys Golf | Nonnewaug | Away - Western Hills Golf Course (Wtby) [Directions] | 3:00 p.m. | 180 | |
| Thu., 9/16 | V Field Hockey | Shepaug Valley | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 3:45 p.m. | L 0-5 | |
| Thu., 9/16 | JV Field Hockey | Shepaug Valley | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 5:15 p.m. | ||
| Fri., 9/17 | V Football | Cheney Tech | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | L 0-28 | |
| Fri., 9/17 | V Boys Soccer | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 9/17 | V Field Hockey | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 1-9 | |
| Fri., 9/17 | V Girls Soccer | Thomaston | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | T 2-2 | |
| Sat., 9/18 | JV Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Postponed | ||
| Wed., 9/22 | V Boys Cross Country | Terryville, Housatonic Regional | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | V Boys Golf | Northwestern, Terryville | Home - Litchfield Country Club [Directions] | 3:00 p.m. | 175 | |
| Wed., 9/22 | V Boys Soccer | Housatonic Regional | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 9/22 | V Girls Cross Country | Terryville, Housatonic Regional | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | W 3-0 | |
| Thu., 9/23 | V Boys Golf | Northwestern, Housatonic Regional | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:30 p.m. | 184 | |
| Thu., 9/23 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 4-1 | |
| Sat., 9/25 | V Boys Cross Country | Winding Trails Invitational | Away - Winding Trails Center | 9:00 a.m. | ||
| Sat., 9/25 | V Girls Cross Country | Winding Trails Invitational | Away - Winding Trails-Cross Country Course | 9:00 a.m. | ||
| Mon., 9/27 | V Boys Golf | Northwestern | Home - Litchfield Country Club [Directions] | 3:00 p.m. | 173 | |
| Mon., 9/27 | V Boys Soccer | Terryville | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Mon., 9/27 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 9/28 | V Boys Cross Country | Nonnewaug, Wamogo | Away - Nonnewaug HS-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Girls Cross Country | Nonnewaug, Wamogo | Away - Nonnewaug HS-XC Course [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Boys Golf | Gilbert, Shepaug Valley | Home - Litchfield Country Club [Directions] | 3:00 p.m. | 187 | |
| Wed., 9/29 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | L 9-0 | |
| Wed., 9/29 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | L 0-2 | |
| Wed., 9/29 | V Girls Soccer | Nonnewaug | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-1 | |
| Thu., 9/30 | V Boys Golf | Terryville | Away - Pequabuck Golf Club-Golf Course, Front 9 [Directions] | 3:00 p.m. | ||
| Thu., 9/30 | V Boys Golf | Shepaug Valley, Wamogo | Away - Lake Waramaug Country Club [Directions] | 3:00 p.m. | 181 | |
| Thu., 9/30 | V Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 7:30 p.m. | W 5-0 | |
| Thu., 9/30 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 5:30 p.m. | W 9-2 | |
| Fri., 10/1 | V Boys Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | 4:00 p.m. | ||
| Fri., 10/1 | JV Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | Canceled | Cancelled | |
| Fri., 10/1 | V Girls Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 10/1 | V Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 10/1 | JV Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | Canceled | Cancelled | |
| Fri., 10/1 | JV Girls Soccer | Wamogo | Home - Plumb Hill Field Complex-JV Soccer Field [Directions] | Canceled | Cancelled | |
| Sat., 10/2 | V Football | Norwich Tech | Away - Norwich Technical HS-NTHS Outdoor Athletic Complex [Directions] | 3:00 p.m. | L 20-22 | |
| Mon., 10/4 | V Boys Golf | Lewis Mills | Away - Lewis Mills HS-Fairview Farm Golf Course [Directions] | Canceled | Cancelled | |
| Tue., 10/5 | V Boys Golf | Terryville, Housatonic Regional | Away - Pequabuck Golf Club-Golf Course, Front 9 [Directions] | 3:00 p.m. | Cancelled | |
| Tue., 10/5 | V Boys Golf | Housatonic Regional | Home - Litchfield Country Club [Directions] | 3:00 p.m. | 181 | |
| Tue., 10/5 | V Boys Soccer | Gilbert | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 8-1 | |
| Tue., 10/5 | V Field Hockey | Watertown | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 5:00 p.m. | L 0-6 | |
| Tue., 10/5 | JV Field Hockey | Watertown | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | Postponed | ||
| Tue., 10/5 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 3:30 p.m. | W 8-1 | |
| Thu., 10/7 | V Boys Golf | Shepaug Valley, Gilbert, Terryville | Away - Lake Waramaug Country Club [Directions] | 3:00 p.m. | 174 | |
| Thu., 10/7 | V Girls Soccer | Shepaug Valley | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 6-4 | |
| Fri., 10/8 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-0 | |
| Fri., 10/8 | V Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 10/8 | JV Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Sat., 10/9 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/9 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | 9:00 a.m. | ||
| Tue., 10/12 | V Boys Cross Country | Shepaug Valley, Northwestern | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Boys Soccer | Thomaston | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Tue., 10/12 | V Girls Cross Country | Shepaug Valley, Northwestern | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Field Hockey | Thomaston | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 3:45 p.m. | L 1-9 | |
| Tue., 10/12 | JV Field Hockey | Thomaston | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | Canceled | Cancelled | |
| Tue., 10/12 | V Girls Soccer | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/13 | V Boys Golf | Housatonic Regional | Away - Canaan Country Club [Directions] | 3:00 p.m. | 171 | |
| Wed., 10/13 | V Field Hockey | Northwestern | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 3:45 p.m. | L 0-2 | |
| Thu., 10/14 | V Football | O'Brien Tech | Home - Nonnewaug HS-Turf Field [Directions] | 7:00 p.m. | W 44-8 | |
| Fri., 10/15 | V Field Hockey | Brookfield | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 4:00 p.m. | L 1-4 | |
| Sat., 10/16 | JV Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division II Boys Golf Championship | Away - Silo Point GC | 8:30 a.m. | ||
| Mon., 10/18 | V Boys Soccer | Northwestern | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | T 2-2 | |
| Tue., 10/19 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | W 8-1 | |
| Tue., 10/19 | V Girls Soccer | Housatonic Regional | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 4-1 | |
| Thu., 10/21 | V Boys Cross Country | Berkshire League Championship | Away - Black Rock State Park | 4:15 p.m. | ||
| Thu., 10/21 | V Girls Cross Country | Berkshire League Championship | Away - Black Rock State Park | 3:30 p.m. | ||
| Thu., 10/21 | V Girls Soccer | Wamogo | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 7:00 p.m. | W 8-0 | |
| Fri., 10/22 | V Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 50-6 | |
| Fri., 10/22 | V Boys Soccer | Wamogo | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 7:00 p.m. | W 3-0 | |
| Sat., 10/23 | JV Boys Soccer | Nonnewaug, Wamogo, Watertown | Away - Nonnewaug HS-JV Field [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | V Field Hockey | Wamogo | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 7:00 p.m. | L 0-3 | |
| Mon., 10/25 | JV Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 10/28 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Thu., 10/28 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:15 p.m. | L 0-4 | |
| Fri., 10/29 | V Football | Quinebaug Valley | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 38-14 | |
| Fri., 10/29 | V Boys Soccer | Nonnewaug | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | T 1-1 OT | |
| Fri., 10/29 | V Field Hockey | Nonnewaug | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 10/29 | JV Field Hockey | Nonnewaug | Home - Plumb Hill Field Complex-Field Hockey Field [Directions] | 5:15 p.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class S Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class S Championship | Away - Wickham Park | 2:35 p.m. | ||
| Mon., 11/1 | V Girls Soccer | Terryville | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 11/2 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 3-1 OT | |
| Tue., 11/2 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 11/2 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 11/2 | V Girls Soccer | Northwestern | Home - Plumb Hill Field Complex-JV Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | VGW Techs | Away - Pat Kidney Field-Pat Kidney 1 [Directions] | 6:00 p.m. | W 45-0 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Woodland | Home - Nonnewaug HS-football field [Directions] | 10:00 a.m. | ||
| Mon., 11/8 | V Girls Soccer | Comp Sci | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 2:00 p.m. | ||
| Tue., 11/9 | V Boys Soccer | East Catholic | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 2:00 p.m. | L 5-2 | |
| Wed., 11/10 | V Girls Soccer | Thomaston | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 2:00 p.m. | ||
| Sat., 11/13 | V Football | Bullard/Kolbe | Away - Kennedy Stadium (Bridgeport) [Directions] | 12:00 p.m. | L 22-24 | |
| Mon., 11/15 | JV Football | Bullard/Kolbe | Home - Nonnewaug HS-Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 11/19 | V Football | Prince Tech-Innovation | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 38-0 | |
| Thu., 11/25 | V Football | ATI | Away - Immaculate HS-Mustang Valley [Directions] | 10:00 a.m. | W 36-20 | |
| Mon., 11/29 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Tue., 11/30 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Wed., 12/1 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Thu., 12/2 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 12/3 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | ||
| Sat., 12/4 | V Girls Ice Hockey | Hamden Coop (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:30 p.m. | Scrimmage | |
| Mon., 12/6 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8-9:30 p.m. | ||
| Tue., 12/7 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Wed., 12/8 | V Boys Basketball | Watertown (Scrim.) | Away - Watertown HS [Directions] | 6:30 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Housatonic Coop (Scrim.) | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:30 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Abbott Tech (Scrim.) | Home - Litchfield HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 4-3 OT | |
| Thu., 12/9 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 12/10 | V Boys Basketball | Wolcott (Scrim.) | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/10 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:45-8:15 p.m. | ||
| Fri., 12/10 | V Girls Basketball | Wolcott Tech (Scrim.) | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/10 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 4-3 | |
| Mon., 12/13 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Mon., 12/13 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 31-66 | |
| Mon., 12/13 | JV Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/14 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Wed., 12/15 | V Boys Ice Hockey | Masuk | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:00 p.m. | L 2-8 | |
| Wed., 12/15 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | L 3-0 | |
| Thu., 12/16 | V Boys Basketball | Terryville | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | L 38-41 | |
| Thu., 12/16 | JV Boys Basketball | Terryville | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 6:45 p.m. | W 36-31 | |
| Thu., 12/16 | JV Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/17 | V Boys Ice Hockey | Byram Hills (NY) | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:00 p.m. | W 4-1 | |
| Fri., 12/17 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Sat., 12/18 | V Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | L 4-1 | |
| Sun., 12/19 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | ||
| Mon., 12/20 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Tue., 12/21 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 7:00 p.m. | W 48-37 | |
| Tue., 12/21 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/21 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Tue., 12/21 | V Girls Basketball | Gilbert | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | L 48-34 | |
| Tue., 12/21 | JV Girls Basketball | Gilbert | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/22 | V Boys Ice Hockey | Mt. Everett (MA) | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:00 p.m. | W 5-0 | |
| Thu., 12/23 | V Boys Basketball | Canton | Away - Canton HS-Gym [Directions] | 6:45 p.m. | W 58-48 | |
| Thu., 12/23 | JV Boys Basketball | Canton | Away - Canton HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/23 | FR Boys Basketball | Canton | Away - Canton HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 12/23 | V Boys Ice Hockey | Scrimmage vs Watertown Midgets | Away - Taft School Mays, Watertown, CT | 7:15 p.m. | No Bus Scheduled | |
| Thu., 12/23 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | ||
| Mon., 12/27 | V Boys Basketball | Thomaston | Home - Litchfield HS-Gym [Directions] | 6:30 p.m. | W 62-27 | |
| Tue., 12/28 | V Boys Basketball | Woodland | Home - Litchfield HS-Gym [Directions] | 6:25 p.m. | L 46-49 | |
| Tue., 12/28 | JV Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/29 | FR Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Small Gym [Directions] | 1:45 p.m. | ||
| Wed., 12/29 | V Boys Ice Hockey | TBA | Home - The Frederick Gunn School-Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 12/29 | JV Girls Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 11:30 a.m. | ||
| Mon., 1/3 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | ||
| Tue., 1/4 | V Boys Basketball | Nonnewaug | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 49-35 | |
| Tue., 1/4 | JV Boys Basketball | Nonnewaug | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/4 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 1/4 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 6:00 p.m. | ||
| Tue., 1/4 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | L 15-63 | |
| Tue., 1/4 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/5 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | Voluntary Practice | |
| Wed., 1/5 | V Boys Indoor Track | Wintergreen Meet SCSU | Away - Southern Connecticut State University | Canceled | Cancelled | |
| Wed., 1/5 | V Girls Indoor Track | Wintergreen Meet SCSU | Away - Southern Connecticut State University | Canceled | Cancelled | |
| Thu., 1/6 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 1/7 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Sat., 1/8 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 5:30-7 p.m. | ||
| Sat., 1/8 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:15 p.m. | W 4-3 | |
| Sun., 1/9 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Blue Rink [Directions] | 6:30 p.m. | L 5-1 | |
| Mon., 1/10 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Mon., 1/10 | V Boys Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Mon., 1/10 | V Girls Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Tue., 1/11 | V Boys Basketball | Shepaug Valley | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 59-48 | |
| Tue., 1/11 | JV Boys Basketball | Shepaug Valley | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/11 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:30 p.m. | L 0-9 | |
| Tue., 1/11 | V Boys Swimming and Diving | Nonnewaug | Away - John F. Kennedy HS-JFK Pool [Directions] | 7:00 p.m. | ||
| Tue., 1/11 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 6:00 p.m. | L 10-29 | |
| Tue., 1/11 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Postponed | ||
| Tue., 1/11 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:15 p.m. | L 2-1 | |
| Wed., 1/12 | V Boys Ice Hockey | JBWA | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:00 p.m. | L 2-7 | |
| Wed., 1/12 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:45 p.m. | ||
| Thu., 1/13 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | Canceled | Cancelled | |
| Fri., 1/14 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 7:00 p.m. | W 75-37 | |
| Fri., 1/14 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Fri., 1/14 | JV Girls Basketball | Housatonic Regional | Home - Litchfield HS-Gym [Directions] | Postponed | ||
| Fri., 1/14 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-Red [Directions] | 4:00 p.m. | W 5-1 | |
| Sun., 1/16 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:30 p.m. | L 3-8 | No Bus |
| Sun., 1/16 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:30 p.m. | W 5-1 | |
| Mon., 1/17 | V Boys Ice Hockey | Milford Coop | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | T 1-1 | |
| Mon., 1/17 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 1:00 p.m. | L 8-0 | |
| Tue., 1/18 | V Boys Basketball | Northwestern | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 52-51 | |
| Tue., 1/18 | JV Boys Basketball | Northwestern | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/18 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:30 p.m. | W 2-1(OT) | |
| Tue., 1/18 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | L 30-37 | |
| Tue., 1/18 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | Postponed | ||
| Wed., 1/19 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Thu., 1/20 | FR Boys Basketball | Wolcott Tech | Home - Litchfield HS-Gym [Directions] | Postponed | ||
| Thu., 1/20 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | Canceled | Cancelled | |
| Fri., 1/21 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School-NHL | 7:00 p.m. | T 2-2 | |
| Fri., 1/21 | V Boys Swimming and Diving | Lewis Mills | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Thomaston | Home - Litchfield HS-Gym [Directions] | 6:00 p.m. | L 51-19 | |
| Fri., 1/21 | JV Girls Basketball | Thomaston | Home - Litchfield HS-Gym [Directions] | Postponed | ||
| Fri., 1/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 2-0 | |
| Sat., 1/22 | V Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 45-46 | |
| Sat., 1/22 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Small Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/22 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | W 43-36 | |
| Sat., 1/22 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:30 p.m. | L 3-1 | |
| Sun., 1/23 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 6:25 p.m. | ||
| Mon., 1/24 | V Boys Ice Hockey | Brookfield | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | L 0-3 | |
| Mon., 1/24 | V Girls Basketball | Branford | Away - Branford HS-Gym [Directions] | 6:00 p.m. | L 28-50 | |
| Tue., 1/25 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | L 53-69 | |
| Tue., 1/25 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/25 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 1/25 | V Boys Swimming and Diving | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Terryville | Home - Litchfield HS-Gym [Directions] | 6:00 p.m. | L 39-31 | |
| Tue., 1/25 | JV Girls Basketball | Terryville | Home - Litchfield HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/25 | JV Girls Basketball | Terryville | Home - Litchfield HS-Gym [Directions] | Postponed | ||
| Wed., 1/26 | V Boys Ice Hockey | Housatonic Coop | Away - South Kent School-Ice Rink [Directions] | 6:00 p.m. | L 2-6 | |
| Wed., 1/26 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 5:30 p.m. | ||
| Wed., 1/26 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | L 3-1 | |
| Thu., 1/27 | V Boys Basketball | Wolcott Tech | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 71-48 | |
| Thu., 1/27 | JV Boys Basketball | Wolcott Tech | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/27 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Fri., 1/28 | V Boys Basketball | Gilbert | Home - Litchfield HS-Gym [Directions] | 5:15 p.m. | W 67-36 | |
| Fri., 1/28 | JV Boys Basketball | Gilbert | Home - Litchfield HS-Gym [Directions] | Postponed | ||
| Fri., 1/28 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8-9:30 p.m. | ||
| Fri., 1/28 | V Boys Indoor Track | Shoreline Coaches Invite | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Fri., 1/28 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:00 p.m. | L 38-47 | |
| Fri., 1/28 | JV Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/28 | V Girls Ice Hockey | Guilford Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 6-1 | |
| Fri., 1/28 | V Girls Indoor Track | Shoreline Coaches Invite | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Sat., 1/29 | V Boys Indoor Track | Frostbite Invitational | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | Canceled | Cancelled | |
| Sat., 1/29 | V Girls Indoor Track | Frostbite Invitational | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | Canceled | Cancelled | |
| Sun., 1/30 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 6:15 p.m. | No Bus | |
| Mon., 1/31 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6-7:30 p.m. | ||
| Mon., 1/31 | V Girls Basketball | Housatonic Regional | Home - Litchfield HS-Gym [Directions] | 4:00 p.m. | L 51-30 | |
| Tue., 2/1 | FR Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/1 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 2/1 | V Boys Indoor Track | Bethel Last Chance Meet | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Tue., 2/1 | V Boys Swimming and Diving | Housatonic Regional | Home - Connecticut Junior Republic-Pool [Directions] | 5:00 p.m. | ||
| Tue., 2/1 | JV Girls Basketball | Masters School (Scrim.) | Home - Litchfield HS-Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/1 | V Girls Indoor Track | Bethel Last Chance Meet | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | New Milford | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | L 1-7 | |
| Wed., 2/2 | JV Girls Basketball | Wolcott Tech | Home - Litchfield HS-Gym [Directions] | 6:30 p.m. | ||
| Wed., 2/2 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 3-2 | No Bus |
| Thu., 2/3 | V Boys Basketball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 6:45 p.m. | L 39-54 | |
| Thu., 2/3 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Thu., 2/3 | V Girls Basketball | Nonnewaug | Home - Litchfield HS-Gym [Directions] | 6:00 p.m. | L 68-29 | |
| Thu., 2/3 | JV Girls Basketball | Nonnewaug | Home - Litchfield HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 2/5 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:00 p.m. | L 45-57 | |
| Sat., 2/5 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 3:30 p.m. | ||
| Sun., 2/6 | JV Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:45 p.m. | ||
| Mon., 2/7 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | Canceled | Cancelled | |
| Tue., 2/8 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 59-51 OT | |
| Tue., 2/8 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 6:15-7:45 p.m. | ||
| Tue., 2/8 | V Boys Swimming and Diving | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Shepaug Valley | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | L 45-22 | |
| Tue., 2/8 | JV Girls Basketball | Shepaug Valley | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/9 | V Boys Ice Hockey | Housatonic Coop | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:30 p.m. | L 4-5 | |
| Thu., 2/10 | V Boys Basketball | Wamogo | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | L 43-65 | |
| Thu., 2/10 | JV Boys Basketball | Wamogo | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/10 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Thu., 2/10 | V Girls Ice Hockey | Guilford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:10 p.m. | L 9-2 | |
| Fri., 2/11 | V Boys Ice Hockey | SCW Knights | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:30 p.m. | W 4-1 | |
| Fri., 2/11 | V Girls Basketball | Wamogo | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | L 36-38 | |
| Fri., 2/11 | JV Girls Basketball | Wamogo | Home - Litchfield HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/11 | V Girls Ice Hockey | Conard | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 3-1 | |
| Sat., 2/12 | V Boys Ice Hockey | Byram Hills (NY) | Away - Brewster Ice Rink-Ice Rink | 3:45 p.m. | W 8-4 | Pink the Rink |
| Sat., 2/12 | V Boys Swimming and Diving | Northwestern | Away - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Sun., 2/13 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Ice Hockey | Pawling (NY) | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | L 2-3 OT | |
| Tue., 2/15 | V Boys Basketball | Housatonic Regional | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 81-51 | |
| Tue., 2/15 | JV Boys Basketball | Housatonic Regional | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Tue., 2/15 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 7:00 p.m. | L 30-57 | |
| Tue., 2/15 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | Newtown/New Fairfield | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:30 p.m. | L 1-2 | |
| Wed., 2/16 | V Boys Swimming and Diving | Granby Memorial | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Thu., 2/17 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 47-70 | |
| Thu., 2/17 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Thu., 2/17 | V Girls Basketball | Northwestern | Home - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 35-32 | |
| Thu., 2/17 | JV Girls Basketball | Northwestern | Home - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 3-2(OT) | |
| Fri., 2/18 | FR Boys Basketball | Shepaug Valley | Home - Litchfield HS-Gym [Directions] | 6:30 p.m. | ||
| Fri., 2/18 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Fri., 2/18 | V Boys Swimming and Diving | Shepaug Valley | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 2/18 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-1 | |
| Sat., 2/19 | V Girls Basketball | Nonnewaug | Away - Thomaston HS-Gym [Directions] | 1:15 p.m. | ||
| Mon., 2/21 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30-10 p.m. | ||
| Mon., 2/21 | V Girls Basketball | Branford | Home - Litchfield HS-Gym [Directions] | 3:30 p.m. | L 59-40 | |
| Mon., 2/21 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 2:00 p.m. | ||
| Tue., 2/22 | V Boys Ice Hockey | Brookfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:30 p.m. | L 0-5 | |
| Tue., 2/22 | V Boys Swimming and Diving | Wamogo | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Wed., 2/23 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 51-41 | |
| Wed., 2/23 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | New Milford | Away - Canterbury School-O'Neill Arena [Directions] | 7:15 p.m. | L 2-8 | |
| Wed., 2/23 | V Boys Swimming and Diving | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Thu., 2/24 | FR Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 2/25 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7:30-9 p.m. | ||
| Sat., 2/26 | V Boys Basketball | Nonnewaug | Home - Nonnewaug HS-Gym [Directions] | 4:45 p.m. | ||
| Sat., 2/26 | V Boys Swimming and Diving | TBA, Housatonic Regional, TBA, Nonnewaug, Northwestern, Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 11:00 a.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | ||
| Tue., 3/1 | V Boys Basketball | Terryville | Away - Nonnewaug HS-Gym [Directions] | 7:00 p.m. | ||
| Tue., 3/1 | V Boys Basketball | Terryville | Away - Nonnewaug HS-Nonnewaug [Directions] | 7:00 p.m. | ||
| Tue., 3/1 | V Boys Ice Hockey | Practice | Home - Shepaug Valley HS-Shepaug Exercise Room [Directions] | 3:30-4:30 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | ||
| Fri., 3/4 | V Boys Ice Hockey | Practice | Home - The Frederick Gunn School-Ice Rink [Directions] | 7-8:30 p.m. | ||
| Fri., 3/4 | V Boys Swimming and Diving | Berkshire League Dive Championship | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 5:30 p.m. | ||
| Sat., 3/5 | V Boys Swimming and Diving | Housatonic Regional, Nonnewaug, Northwestern, Shepaug Valley, Wamogo | Home - John F. Kennedy HS-JFK Pool [Directions] | 4:30 p.m. | ||
| Mon., 3/7 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | ||
| Tue., 3/8 | V Boys Basketball | O'Brien Tech | Home - Litchfield HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | V Boys Basketball | Weaver | Away - Weaver HS-Doc Hurley Fieldhouse [Directions] | 6:30 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Fri., 3/25 | V Baseball | St. Paul Catholic (Scrim.) | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Baseball | Derby (Scrim.) | Away - Payden Park [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Girls Tennis | Suffield (Scrim.) | Away - Suffield HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/1 | V Girls Tennis | Taft (NY) (Scrim.) | Away - Taft School | 3:45 p.m. | ||
| Mon., 4/4 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | L 2-8 | |
| Mon., 4/4 | V Boys Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Mon., 4/4 | V Softball | Terryville | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 19-3 | |
| Tue., 4/5 | V Baseball | Torrington | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 1-19 | |
| Fri., 4/8 | V Girls Tennis | Nonnewaug | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Sat., 4/9 | JV Baseball | Nonnewaug, Shepaug Valley | Away - Nonnewaug HS-Varsity Field [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 4/11 | V Boys Outdoor Track | Terryville Invitational | Away - Terryville HS-Default Facility | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Northwestern | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Mon., 4/11 | V Girls Outdoor Track | Terryville Invitational | Away - Terryville HS-Track | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/12 | V Baseball | Wolcott Tech | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 6-16 | |
| Tue., 4/12 | V Softball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | L 4-10 | |
| Tue., 4/12 | V Girls Tennis | Gilbert | Away - Walker Field-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/13 | V Baseball | Northwestern | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 1-14 | |
| Wed., 4/13 | V Softball | Nonnewaug | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 5-23 | |
| Wed., 4/13 | V Girls Tennis | Housatonic Regional | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/16 | V Baseball | Terryville | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 11:00 a.m. | L 1-8 | |
| Wed., 4/20 | V Baseball | Nonnewaug | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 0-14 | |
| Thu., 4/21 | V Baseball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 10:30 a.m. | W 14-9 | |
| Sat., 4/23 | JV Baseball | Nonnewaug | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 10:30 a.m. | ||
| Mon., 4/25 | V Baseball | Housatonic Regional | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 6-9 | |
| Mon., 4/25 | V Boys Tennis | Shepaug Valley | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 3-2 [Detailed Results] | |
| Mon., 4/25 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 11-26 | |
| Mon., 4/25 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Tue., 4/26 | V Boys Outdoor Track | Thomaston, Gilbert | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Outdoor Track | Thomaston, Gilbert | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | L 0-16 | |
| Tue., 4/26 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/27 | V Baseball | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 15-0 | |
| Wed., 4/27 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Wed., 4/27 | V Softball | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 0-20 | |
| Wed., 4/27 | V Girls Tennis | Wamogo | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/29 | V Baseball | Thomaston | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | W 17-6 | |
| Fri., 4/29 | V Boys Tennis | Housatonic Regional | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Fri., 4/29 | V Girls Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/30 | JV Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 10:30 a.m. | ||
| Sat., 4/30 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 9:30 a.m. | ||
| Sat., 4/30 | JV Girls Tennis | JV Girls Tennis Tournament | Away - Nonnewaug HS-Tennis Courts | 9:00 a.m. | ||
| Mon., 5/2 | V Boys Outdoor Track | Terryville, Housatonic Regional | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Girls Outdoor Track | Terryville, Housatonic Regional | Away - Terryville HS-Track [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Softball | Wolcott Tech | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 17-4 | |
| Mon., 5/2 | V Girls Tennis | Gilbert | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 5/3 | V Baseball | Shepaug Valley | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | W 5-4 | |
| Tue., 5/3 | JV Baseball | Shepaug Valley | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | Postponed | ||
| Tue., 5/3 | V Boys Tennis | Nonnewaug | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Tue., 5/3 | V Softball | Terryville | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 25-0 | |
| Tue., 5/3 | JV Softball | Kaynor Tech | Home - Wamogo Regional HS-Plumb Hill Field [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Girls Tennis | Pomperaug | Away - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 4:00 p.m. | L 2-5 | |
| Thu., 5/5 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-3 [Detailed Results] | |
| Thu., 5/5 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | 5:00 p.m. | L 7-8 | |
| Thu., 5/5 | JV Softball | Housatonic Regional | Away - Housatonic Valley Regional High-Softball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:30 p.m. | L 3-4 [Detailed Results] | |
| Fri., 5/6 | JV Softball | Northwestern | Home - Wamogo Regional HS-Plumb Hill Field [Directions] | Postponed | ||
| Sat., 5/7 | JV Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | Postponed | ||
| Mon., 5/9 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 6:30 p.m. | L 11-0 | |
| Mon., 5/9 | V Boys Tennis | Thomaston | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 5/9 | V Softball | Canton | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 4:00 p.m. | L 3-9 | |
| Mon., 5/9 | V Girls Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/10 | V Boys Outdoor Track | Northwestern, Shepaug Valley | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Tue., 5/10 | V Girls Outdoor Track | Northwestern, Shepaug Valley | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Tue., 5/10 | V Girls Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 5/11 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 5:00 p.m. | L 8-18 | |
| Wed., 5/11 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 5/11 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:00 p.m. | L 0-15 | |
| Wed., 5/11 | V Girls Tennis | Shepaug Valley | Home - Litchfield HS-LHS Tennis Courts [Directions] | 4:30 p.m. | W 5-2 [Detailed Results] | |
| Thu., 5/12 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 5:00 p.m. | L 4-14 | |
| Thu., 5/12 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Thu., 5/12 | V Softball | Kaynor Tech | Home - Plumb Hill Field Complex-Softball Field [Directions] | 3:45 p.m. | L 0-12 | |
| Fri., 5/13 | V Baseball | Wamogo | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 1-7 | |
| Fri., 5/13 | V Boys Outdoor Track | Torrington | Away - Torrington HS [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Boys Tennis | Wamogo | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 3-2 [Detailed Results] | |
| Fri., 5/13 | V Girls Outdoor Track | Torrington | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Time to 4:30 p.m., Facility to Torrington HS | ||||||
| Fri., 5/13 | V Softball | Northwestern | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 0-15 | |
| Fri., 5/13 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Sat., 5/14 | JV Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Boys Outdoor Track | Nonnewaug, Wamogo | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:00 p.m. | W 5-0 | |
| Tue., 5/17 | V Girls Outdoor Track | Nonnewaug, Wamogo | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 4:00 p.m. | L 12-14 | |
| Tue., 5/17 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 5:30 p.m. | W 13-0 | |
| Tue., 5/17 | V Girls Tennis | Northwestern | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 5/18 | V Baseball | Wamogo | Away - Wamogo Regional HS-Dunkin Donuts Park [Directions] | 6:30 p.m. | L 4-5 | |
| Wed., 5/18 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - Nonnewaug HS-Nonnewaug | 8:00 a.m. | ||
| Thu., 5/19 | V Boys Tennis | Berkshire League Boys Tennis Tournament | Away - TBA | 8:00 a.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/20, Facility to Nonnewaug HS-Nonnewaug | ||||||
| Thu., 5/19 | V Girls Tennis | Thomaston | Home - Litchfield HS-LHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/20 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 5:00 p.m. | L 1-11 | |
| Fri., 5/20 | V Softball | Thomaston | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 0-10 | |
| Sat., 5/21 | V Boys Outdoor Track | Berkshire League Track Championships | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 5/21 | V Girls Outdoor Track | Berkshire League Track Championships | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Mon., 5/23 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Varsity Baseball Diamond [Directions] | 5:15 p.m. | L 4-5 | |
| Mon., 5/23 | V Boys Tennis | Berkshire League Boys Tennis Tournament Semi & Finals | Away - TBA | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Mon., 5/23 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 3:45 p.m. | L 0-10 | |
| Mon., 5/23 | V Girls Tennis | Berkshire League Girls Tennis Tournament Semi & Finals | Away - Nonnewaug HS-Nonnewaug | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Tue., 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. | ||
| Tue., 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., 5/24 | V Softball | Canton | Away - Canton HS-Softball Diamond [Directions] | 5:00 p.m. | L 2-7 | |
| Tue., 5/24 | V Girls Tennis | Lewis Mills | Home - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/25 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | W 6-5 | |
| Wed., 5/25 | 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 - Thomaston Nystrom Park-Nystroms Park Track | 3:30 p.m. | ||
| Wed., 5/25 | V Boys Tennis | Farmington | Away - Farmington HS [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/25 | 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 - Thomaston Nystrom Park-Nystroms Park Track | 3:30 p.m. | ||
| Wed., 5/25 | V Softball | Housatonic Regional | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 5/25 | V Girls Tennis | Farmington | Away - Farmington HS [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 5/26 | V Baseball | Gilbert | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 4:00 p.m. | W 10-0 | |
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Boys Tennis | Wamogo | Home - Litchfield HS-LHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Tennis | Notre Dame-Fairfield | Home - Litchfield HS-LHS Tennis Courts [Directions] | 2:00 p.m. | ||
| Wed., 6/1 | JV Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | Rainout | ||
| Wed., 6/1 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 1:00 p.m. | ||
| Wed., 6/1 | V Girls Tennis | East Catholic | Home - Litchfield HS-LHS Tennis Courts [Directions] | 11:00 a.m. | ||
| Thu., 6/2 | JV Baseball | Wamogo | Home - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 6/2 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 12:00 p.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||