| Northwestern 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 547 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Mon., 8/28 | V Boys Soccer | Lewis Mills (Scrim.) | Away - Lewis Mills HS-Soccer JV Field [Directions] | 5:00 p.m. | ||
| Mon., 8/28 | JV Boys Soccer | Lewis Mills (Scrim.) | Away - Lewis Mills HS-JV Soccer/Lacrosse Field [Directions] | 5:00 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Granby Memorial (Scrim.) | Away - Granby Memorial HS-Stadium Field [Directions] | 6:30 p.m. | ||
| Thu., 8/31 | V Boys Golf | Nonnewaug | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 3:00 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Torrington (Scrim.) | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | ||
| Fri., 9/1 | V Football | Granby/Canton (Scrim.) | Away - Granby Memorial HS-Stadium Field [Directions] | 7:00 a.m. | ||
| Fri., 9/1 | V Boys Soccer | Foran Jamboree | Away - Foran HS -Kelley Martin Tighe Memorial Field | 4:00 p.m. | ||
| Fri., 9/1 | V Field Hockey | Nonnewaug (Scrim.) | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | ||
| Fri., 9/1 | V Girls Soccer | Canton (Scrim.) | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 4:00 p.m. | ||
| Sat., 9/2 | V Girls Volleyball | Glastonbury Volleyball Jamboree- AM wave | Away - Glastonbury HS-Gym | 8:30 a.m. | ||
| Sun., 9/3 | V Girls Soccer | Granby Memorial, Enfield, Housatonic Regional, Notre Dame-Fairfield, Simsbury, Suffield, Valley Regional | Away - Granby Memorial HS-Stadium Field | 8:00 a.m. | ||
| Tue., 9/5 | V Boys Golf | Shepaug Valley | Away - Washington Club Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/5 | V Boys Soccer | Watertown (Scrim.) | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | JV Boys Soccer | Watertown (Scrim.) | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | V Girls Volleyball | Woodland (Scrim.) | Away - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/6 | V Boys Cross Country | BL Cross Country Scrimmage | Away - Thomaston HS-Black Rock State Park | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Thu., 9/7 | V Football | Ansonia | Away - Nolan Field-Ansonia-Football Field [Directions] | 6:00 p.m. | L 13-45 | |
| Thu., 9/7 | V Boys Golf | Gilbert | Home - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | ||
| Thu., 9/7 | JV Boys Soccer | Torrington | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | 4:30 p.m. | L 2-3 | |
| Fri., 9/8 | JV Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 7:00 p.m. | ||
| Fri., 9/8 | V Field Hockey | Wamogo | Away - Wamogo HS-Field Hockey Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 9/8 | V Girls Volleyball | New Milford | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:15 p.m. | W 3-2 | |
| Fri., 9/8 | JV Girls Volleyball | New Milford | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:00 p.m. | L 0-2 | |
| Sat., 9/9 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 12:00 p.m. | W 7-1 | |
| Sat., 9/9 | V Girls Soccer | Terryville | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 10:00 a.m. | W 1-0 | |
| Tue., 9/12 | V Boys Cross Country | Housatonic Regional, Wamogo | Away - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Golf | Housatonic Regional | Home - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 4:30 p.m. | L 1-2 | |
| Tue., 9/12 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 4:30 p.m. | L 0-2 | |
| Tue., 9/12 | V Girls Cross Country | Housatonic Regional, Wamogo | Away - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:15 p.m. | OT-L 0-1 | |
| Tue., 9/12 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 4:30 p.m. | L 0-1 | |
| Tue., 9/12 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:15 p.m. | L 0-1 | |
| Tue., 9/12 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 3:15 p.m. | L 0-3 | |
| Tue., 9/12 | V Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 9/12 | JV Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 9/13 | V Boys Soccer | Wamogo | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 9/14 | V Boys Golf | Litchfield | Home - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | ||
| Thu., 9/14 | V Field Hockey | Canton | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 9/14 | JV Field Hockey | Canton | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Thu., 9/14 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 6-0 | |
| Thu., 9/14 | JV Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 9/15 | V Football | Kennedy | Home - Gilbert School-Football Field [Directions] | 7:00 p.m. | W 21-7 | |
| Fri., 9/15 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/15 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/16 | JV Football | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 10:00 a.m. | ||
| Sat., 9/16 | JV Boys Soccer | Litchfield, Nonnewaug, Shepaug Valley | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 9:00 a.m. | [Detailed Results] | |
| Sat., 9/16 | JV Field Hockey | BL JV Jamboree- 2 Fields/4 officials/ 2.5 hours | Away - Nonnewaug HS-Turf Field | 9:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 9/16 | JV Girls Soccer | Litchfield, Nonnewaug, Shepaug Valley | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 11:00 a.m. | ||
| Tue., 9/19 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 9/19 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 5:15 p.m. | ||
| Tue., 9/19 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Tue., 9/19 | V Girls Volleyball | Nonnewaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Tue., 9/19 | JV Girls Volleyball | Nonnewaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | L 1-2 | |
| Wed., 9/20 | V Boys Golf | Wamogo | Away - Wamogo HS-Stonybrook Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | V Boys Golf | Nonnewaug | Home - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | ||
| Fri., 9/22 | V Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:00 p.m. | W 20-14 | |
| Fri., 9/22 | V Boys Soccer | Shepaug Valley | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 4-3 [Detailed Results] | |
| Fri., 9/22 | JV Boys Soccer | Shepaug Valley | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | T 3-3 | |
| Fri., 9/22 | V Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 9/22 | JV Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Fri., 9/22 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | W 8-0 | |
| Fri., 9/22 | V Girls Volleyball | Canton | Away - Canton HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/22 | JV Girls Volleyball | Canton | Away - Canton HS-Gym [Directions] | 5:00 p.m. | L 1-2 | |
| Fri., 9/22 | FR Girls Volleyball | Canton | Away - Canton HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/23 | JV Football | Torrington | Home - Gilbert School-Football Field [Directions] | 9:00 a.m. | ||
| Mon., 9/25 | V Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 9/25 | JV Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/26 | V Boys Cross Country | Nonnewaug, Shepaug Valley | Away - Nonnewaug HS-XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Nonnewaug, Shepaug Valley | Away - Nonnewaug HS-XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | MS Girls Volleyball | North End MS | Away - North End MS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 9/27 | V Boys Soccer | Litchfield | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Wed., 9/27 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Practice Field [Directions] | 3:45 p.m. | L 0-4 | |
| Wed., 9/27 | V Field Hockey | Watertown | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | L 1-3 | |
| Wed., 9/27 | JV Field Hockey | Watertown | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | Canceled | Cancelled | |
| Wed., 9/27 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:45 p.m. | L 2-4 | |
| Wed., 9/27 | JV Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Practice Field [Directions] | 3:45 p.m. | W 5-4 | |
| Thu., 9/28 | V Boys Soccer | Gilbert | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | Forfeit | W Forfeit | |
| Fri., 9/29 | V Girls Volleyball | Granby Memorial | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/29 | JV Girls Volleyball | Granby Memorial | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/30 | V Football | Woodland | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 2:00 p.m. | L 0-34 | |
| Mon., 10/2 | JV Football | Woodland | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Boys Golf | Wamogo | Home - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | ||
| Mon., 10/2 | V Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | W 3-0 | |
| Mon., 10/2 | V Girls Soccer | Thomaston | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 6:00 p.m. | L 2-4 | |
| Tue., 10/3 | V Boys Cross Country | Litchfield, Thomaston | Home - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Golf | Gilbert | Away - Green woods Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/3 | V Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 4-0 | |
| Tue., 10/3 | V Girls Cross Country | Litchfield, Thomaston | Home - Northwestern Regional H.S.-Track [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Field Hockey | Wamogo | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/3 | JV Field Hockey | Wamogo | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Wamogo | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 10/3 | JV Girls Soccer | Wamogo | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/3 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/3 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | L 1-2 | |
| Wed., 10/4 | V Boys Golf | Shepaug Valley | Home - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | ||
| Thu., 10/5 | V Boys Golf | Housatonic Regional | Away - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Thu., 10/5 | V Boys Soccer | Terryville | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 10/5 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 0-5 | |
| Thu., 10/5 | V Girls Volleyball | Lewis Mills | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/5 | JV Girls Volleyball | Lewis Mills | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Sat., 10/7 | JV Boys Soccer | Thomaston | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | Postponed | ||
| Mon., 10/9 | V Football | Naugatuck | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:30 p.m. | L 21-41 | |
| Mon., 10/9 | JV Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 10:00 a.m. | ||
| Mon., 10/9 | V Girls Volleyball | Suffield | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 10/9 | JV Girls Volleyball | Suffield | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:30 p.m. | L 0-2 | |
| Tue., 10/10 | V Boys Cross Country | Gilbert, Terryville | Home - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | FM Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | ||
| Tue., 10/10 | V Boys Golf | Litchfield | Away - Litchfield Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | Gilbert, Terryville | Home - Northwestern Regional H.S.-Track [Directions] | 3:30 p.m. | ||
| Tue., 10/10 | V Field Hockey | Nonnewaug | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/10 | JV Field Hockey | Nonnewaug | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/10 | V Girls Soccer | Nonnewaug | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 10/10 | JV Girls Soccer | Nonnewaug | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 10/10 | V Girls Volleyball | Terryville | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/10 | JV Girls Volleyball | Terryville | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 10/11 | V Boys Soccer | Nonnewaug | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 10/12 | V Boys Golf | Shepaug Valley | Away - Lake Waramaug Country Club [Directions] | Canceled | Cancelled | |
| Thu., 10/12 | V Boys Soccer | Housatonic Regional | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 2-0 | |
| Thu., 10/12 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 10/12 | V Girls Volleyball | SMSA | Away - Sport and Medical Sciences Academy (SMSA)-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/12 | JV Girls Volleyball | SMSA | Away - Sport and Medical Sciences Academy (SMSA)-Gym [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 10/12 | FR Girls Volleyball | SMSA | Away - Sport and Medical Sciences Academy (SMSA)-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 10/13 | V Field Hockey | Lewis Mills | Away - Lewis Mills HS-Field Hockey Field [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/13 | JV Field Hockey | Lewis Mills | Away - Lewis Mills HS-Field Hockey Field [Directions] | 5:15 p.m. | ||
| Fri., 10/13 | JV Girls Soccer | Lewis Mills | Away - Lewis Mills HS-Soccer JV Field [Directions] | 3:45 p.m. | ||
| Sat., 10/14 | JV Boys Soccer | Litchfield, Housatonic Regional | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/14 | JV Girls Soccer | Litchfield, Housatonic Regional, Thomaston | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/14 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 12:30 p.m. | W 3-0 | |
| Sat., 10/14 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 11:00 a.m. | W 2-1 | |
| Mon., 10/16 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Practice Field [Directions] | 3:45 p.m. | L 1-2 | |
| Mon., 10/16 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Practice Field [Directions] | Postponed | ||
| Mon., 10/16 | V Girls Soccer | Housatonic Regional | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-2 | |
| Mon., 10/16 | JV Girls Soccer | Housatonic Regional | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 10/17 | V Boys Golf | Berkshire League Golf All-Star Tournament | Away - Fairfiew Farm Golf Course | 8:00 a.m. | ||
| Tue., 10/17 | JV Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 10/17 | V Girls Volleyball | Gilbert | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/17 | JV Girls Volleyball | Gilbert | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 10/18 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-3 | |
| Wed., 10/18 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/18 | V Field Hockey | Shepaug Valley | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | L 0-4 | |
| Wed., 10/18 | JV Field Hockey | Shepaug Valley | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Wed., 10/18 | V Girls Soccer | Shepaug Valley | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 10/18 | JV Girls Soccer | Shepaug Valley | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 10/19 | V Boys Cross Country | Thomaston, Gilbert, Housatonic Regional, Litchfield, Nonnewaug, Shepaug Valley, Terryville, Wamogo | Away - Thomaston HS-Black Rock State Park | 2:45 p.m. | ||
| Thu., 10/19 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W Forfeit | |
| Thu., 10/19 | V Girls Cross Country | Thomaston, Gilbert, Housatonic Regional, Litchfield, Nonnewaug, Shepaug Valley, Terryville, Wamogo | Away - Thomaston HS-Black Rock State Park | 2:45 p.m. | ||
| Thu., 10/19 | V Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | T 0-0 | |
| Fri., 10/20 | V Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 7-12 | |
| Fri., 10/20 | V Girls Volleyball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 5:30 p.m. | L 1-3 | |
| Fri., 10/20 | JV Girls Volleyball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 4:00 p.m. | L 1-2 | |
| Sat., 10/21 | JV Football | Watertown | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 10:00 a.m. | ||
| Sat., 10/21 | JV Field Hockey | BL JV Jamboree- 2 Fields/4 officials/ 2.5 hours | Away - Nonnewaug HS-Turf Field | Canceled | Cancelled | |
| Sat., 10/21 | JV Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 10:00 a.m. | Cancelled | |
| Mon., 10/23 | V Boys Golf | CIAC Division II Fall Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/23 | MS Boys Soccer | Har-Bur MS | Away - Har-Bur MS-Har-Bur Soccer Field [Directions] | 3:30 p.m. | ||
| Mon., 10/23 | V Field Hockey | Lewis Mills | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | L 0-1 | |
| Mon., 10/23 | JV Field Hockey | Lewis Mills | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/24 | V Boys Soccer | Thomaston | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/24 | JV Boys Soccer | Thomaston | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/24 | V Field Hockey | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 10/24 | JV Field Hockey | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 5:00 p.m. | ||
| Tue., 10/24 | V Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 1-3 | |
| Tue., 10/24 | V Girls Volleyball | Wamogo | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/24 | JV Girls Volleyball | Wamogo | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 10/25 | V Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:45 p.m. | W 3-2 | |
| Wed., 10/25 | JV Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 4:30 p.m. | L 1-2 | |
| Thu., 10/26 | JV Football | Seymour | Away - Seymour HS-turf field [Directions] | 5:30 p.m. | ||
| Thu., 10/26 | V Field Hockey | Litchfield | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 3-0 | |
| Thu., 10/26 | JV Field Hockey | Litchfield | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Thu., 10/26 | JV Girls Soccer | Torrington | Home - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 10/26 | V Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:15 p.m. | W 3-0 | |
| Thu., 10/26 | JV Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:45 p.m. | L 0-2 | |
| Fri., 10/27 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 10/27 | V Girls Soccer | Litchfield | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 10/27 | V Girls Volleyball | Housatonic Regional | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 10/27 | JV Girls Volleyball | Housatonic Regional | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class SS Championship | Away | 10:45 a.m. | ||
| Sat., 10/28 | V Football | Seymour | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 20-7 | |
| Sat., 10/28 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park | 10:10 a.m. | ||
| Sat., 10/28 | V Field Hockey | Thomaston | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 11:00 a.m. | W 1-0 ot | |
| Sat., 10/28 | JV Field Hockey | Thomaston | Home - Northwestern Regional H.S.-Field Hockey Field [Directions] | 12:45 p.m. | ||
| Sat., 10/28 | JV Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 10:00 a.m. | ||
| Mon., 10/30 | V Field Hockey | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 3:45 p.m. | L 0-4 | |
| Mon., 10/30 | JV Field Hockey | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 5:15 p.m. | ||
| Mon., 10/30 | V Girls Volleyball | Canton | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/30 | JV Girls Volleyball | Canton | Home - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | L 1-2 | |
| Tue., 10/31 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:15 p.m. | W 3-2 pks | |
| Tue., 10/31 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 3:15 p.m. | W 6-1 | |
| Wed., 11/1 | MS Girls Volleyball | Chase Middle School | Away - Aces at Chase-Goss Field House [Directions] | 3:45 p.m. | ||
| Thu., 11/2 | V Girls Soccer | Litchfield (Scrim.) | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 11/3 | V Boys Soccer | Shepaug Valley | Away - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | L 1-4 | |
| Sat., 11/4 | V Football | Wolcott | Home - Gilbert School-Football Field [Directions] | 2:00 p.m. | W 49-14 | |
| Sat., 11/4 | V Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 2:00 p.m. | ||
| Tue., 11/7 | FM Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 11/7 | V Boys Soccer | WCA | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 2:00 p.m. | W 1-0 Double OT | |
| Wed., 11/8 | V Girls Soccer | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 4:00 p.m. | ||
| Wed., 11/8 | V Girls Volleyball | Sacred Heart Academy | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Thu., 11/9 | V Boys Soccer | Weaver | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 2:00 p.m. | W 5-0 | |
| Fri., 11/10 | V Girls Volleyball | Foran | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Sat., 11/11 | V Football | Holy Cross | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 14-7 | |
| Sat., 11/11 | V Boys Soccer | Stonington | Home - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 1:00 p.m. | L 0-3 | |
| Mon., 11/13 | JV Football | Holy Cross | Home - Walker Field [Directions] | 5:00 p.m. | ||
| Tue., 11/14 | V Girls Volleyball | RHAM | Home - Plainville HS-Kegel Gymansium [Directions] | 6:00 p.m. | ||
| Tue., 11/21 | V Football | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:00 p.m. | W 35-0 | |
| Tue., 11/28 | V Football | Tolland | Away - Tolland HS-Stadium [Directions] | 6:30 p.m. | W 22-16 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Sun., 12/3 | V Football | Watertown | Home - Torrington HS [Directions] | 12:30 p.m. | L 0-21 | |
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Wed., 12/6 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Simsbury - ISCC-NHL [Directions] | 7:00 p.m. | L 2-1 | |
| Thu., 12/7 | V Girls Basketball | Canton (Scrim.) | Away - Canton HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/8 | V Boys Basketball | Lewis Mills (Scrim.) | Away - Lewis Mills HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Girls Ice Hockey | Hamden Coop | Home - Enfield Twin Rinks-Rink 1 [Directions] | 4:10 p.m. | W 9-2 | |
| Sun., 12/10 | V Girls Ice Hockey | Longmeadow (MA) (Scrim.) | Home - Simsbury - ISCC-Olympic [Directions] | 4:10 p.m. | L 5-0 | |
| Mon., 12/11 | V Boys Basketball | Watertown (Scrim.) | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:45 p.m. | ||
| Mon., 12/11 | V Girls Basketball | Kaynor Tech (Scrim.) | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 3:00 p.m. | Cancelled | |
| Wed., 12/13 | V Boys Basketball | Wolcott Tech (Scrim.) | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/13 | JV Boys Basketball | Wolcott Tech (Scrim.) | Away - Wolcott Tech. HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/13 | V Boys Ice Hockey | JBWA | Home - South Kent School-Ice Rink [Directions] | 8:40 p.m. | L 1-5 | |
| Wed., 12/13 | V Wrestling | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/13 | V Girls Basketball | Wolcott Tech | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | W 61-23 | |
| Wed., 12/13 | JV Girls Basketball | Wolcott Tech | Home - Northwestern Regional H.S.-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/13 | V Girls Ice Hockey | Southington Coop | Away - Newington-Red Rink [Directions] | 8:30 p.m. | L 3-1 | |
| Fri., 12/15 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 74-62 | |
| Fri., 12/15 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/15 | V Girls Basketball | Shepaug Valley | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | W 56-22 | |
| Fri., 12/15 | JV Girls Basketball | Shepaug Valley | Home - Northwestern Regional H.S.-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 12/15 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Enfield Twin Rinks-Rink 1 [Directions] | 7:50 p.m. | W 8-0 | |
| Sat., 12/16 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | 5:15 p.m. | L 3-12 | |
| Sat., 12/16 | V Wrestling | Darien Invitational | Away - Darien HS-DHS Main Gym | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Ice Hockey | Guilford Coop | Home - Enfield Twin Rinks-Rink 1 [Directions] | 4:10 p.m. | W 1-0 | |
| Tue., 12/19 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 73-51 | |
| Tue., 12/19 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/19 | V Girls Basketball | Thomaston | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | L 37-47 | |
| Tue., 12/19 | JV Girls Basketball | Thomaston | Home - Northwestern Regional H.S.-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/20 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:45 p.m. | L 2-5 | |
| Wed., 12/20 | V Girls Ice Hockey | Simsbury | Home - Simsbury - ISCC-NHL [Directions] | 7:20 p.m. | W 3-2 | |
| Thu., 12/21 | V Boys Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 4:30 p.m. | ||
| Fri., 12/22 | V Boys Basketball | Terryville | Home - Northwestern Regional H.S.-Main Gym [Directions] | 3:30 p.m. | W 78-54 | |
| Fri., 12/22 | JV Boys Basketball | Terryville | Home - Northwestern Regional H.S.-Main Gym [Directions] | 2:00 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 3:30 p.m. | W 51-29 | |
| Fri., 12/22 | JV Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 12/22 | JV Girls Ice Hockey | East Catholic Coop | Home - Enfield Twin Rinks-Rink 1 [Directions] | 7:50 p.m. | W 3-0 | |
| Sat., 12/23 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 3:45 p.m. | L 2-7 | |
| Wed., 12/27 | V Girls Basketball | Windsor Locks | Home - Northwestern Regional H.S.-Main Gym [Directions] | 1:00 p.m. | W 50-29 | |
| Wed., 12/27 | JV Girls Basketball | Windsor Locks | Home - Northwestern Regional H.S.-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 12/28 | V Boys Basketball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 4:00 p.m. | W 75-50 | |
| Thu., 12/28 | JV Boys Basketball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 2:30 p.m. | ||
| Fri., 12/29 | V Wrestling | Putnam, East Greenwich (RI), Griswold/Wheeler, Stafford | Away - Putnam HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/30 | V Boys Basketball | Newtown | Home - Northwestern Regional H.S.-Main Gym [Directions] | 3:00 p.m. | W 54-51 | |
| Sat., 12/30 | JV Boys Basketball | Newtown | Home - Northwestern Regional H.S.-Main Gym [Directions] | 1:30 p.m. | ||
| Sat., 12/30 | V Boys Indoor Track | Hill House invite | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 12/30 | V Girls Indoor Track | Hillhouse Invite | Away - Floyd Little Athletic Center | TBA | ||
| Tue., 1/2 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | W 77-63 | |
| Tue., 1/2 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/2 | V Girls Basketball | Nonnewaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | W 52-41 | |
| Tue., 1/2 | JV Girls Basketball | Nonnewaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/3 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - South Kent School-Ice Rink [Directions] | 6:00 p.m. | L 4-5 | |
| Wed., 1/3 | V Girls Ice Hockey | Hall/Conard | Home - Enfield Twin Rinks-Rink 1 [Directions] | 3:50 p.m. | L 3-2 | |
| Thu., 1/4 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:30 p.m. | L 45-48 | |
| Thu., 1/4 | JV Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/5 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:30 p.m. | W 77-26 | |
| Fri., 1/5 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Housatonic Regional | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:00 p.m. | ||
| Fri., 1/5 | JV Girls Ice Hockey | Southington Coop | Home - Enfield Twin Rinks-Rink 1 [Directions] | 9:20 p.m. | W 4-0 | |
| Sat., 1/6 | FR Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Boys Indoor Track | Hillhouse invite | Away - Floyd Little Athletic Center | Canceled | Cancelled | |
| Sat., 1/6 | V Wrestling | Warrior Invitational | Away - Canton HS-Gym | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 1/6 | V Girls Ice Hockey | Masuk Coop | Home - Enfield Twin Rinks-Rink 1 [Directions] | 4:10 p.m. | W 2-0 | |
| Sat., 1/6 | V Girls Indoor Track | Hillhouse invite | Away - Floyd Little Athletic Center | Canceled | Cancelled | |
| Mon., 1/8 | V Boys Basketball | Wamogo | Away - Wamogo HS-Large gym [Directions] | 7:00 p.m. | W 50-39 | |
| Mon., 1/8 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Large gym [Directions] | 5:30 p.m. | ||
| Mon., 1/8 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - South Kent School-Ice Rink [Directions] | 3:50 p.m. | L 1-9 | |
| Mon., 1/8 | V Girls Basketball | Wamogo | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:30 p.m. | W 72-34 | |
| Mon., 1/8 | JV Girls Basketball | Wamogo | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/9 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | Postponed | ||
| Wed., 1/10 | V Boys Basketball | Housatonic Regional | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | W 73-34 | |
| Wed., 1/10 | JV Boys Basketball | Housatonic Regional | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/10 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 8:45 p.m. | L 0-2 | |
| Wed., 1/10 | V Wrestling | Derby/Oxford/Holy Cross | Home - Northwestern Regional H.S.-Small Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/10 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | W 52-26 | |
| Wed., 1/10 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/10 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | 3:30 p.m. | L 4-1 | |
| Thu., 1/11 | V Boys Indoor Track | Wesleyan Invite | Away - Wesleyan University | TBA | ||
| Thu., 1/11 | V Girls Indoor Track | Wesleyan invite | Away - Wesleyan University | TBA | ||
| Fri., 1/12 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 65-61 | |
| Fri., 1/12 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Litchfield | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | W 52-18 | |
| Fri., 1/12 | JV Girls Basketball | Litchfield | Home - Northwestern Regional H.S.-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/12 | JV Girls Ice Hockey | Southington Coop | Away - Newington-Red Rink [Directions] | 4:30 p.m. | W 4-1 | |
| Sat., 1/13 | V Boys Swimming and Diving | Litchfield | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:00 p.m. | ||
| Sat., 1/13 | V Wrestling | Staples, Fairfield Prep, Guilford, Foran, Maloney, Simsbury, Stratford, Westhill | Away - Staples HS-Staples Gym | 8:45 a.m. | ||
| Sat., 1/13 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 6:00 p.m. | W 2-1 | |
| Sun., 1/14 | JV Girls Ice Hockey | Pope Francis (MA) | Home - Simsbury - ISCC-Olympic [Directions] | 5:10 p.m. | W 9-1 | |
| Mon., 1/15 | V Boys Indoor Track | BL Invite | Away - Bethel HS Track & Field Training Center | TBA | ||
| Mon., 1/15 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Lower Rink [Directions] | 12:35 p.m. | L 2-1 | |
| Mon., 1/15 | V Girls Indoor Track | BL Invite | Away - Bethel HS Track & Field Training Center | TBA | ||
| Wed., 1/17 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Simsbury - ISCC-Olympic [Directions] | 7:00 p.m. | ||
| Wed., 1/17 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | ||
| Wed., 1/17 | V Wrestling | Terryville-Thomaston | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Suffield | Away - Suffield HS [Directions] | 5:45 p.m. | L 35-50 | |
| Thu., 1/18 | JV Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Lower Rink [Directions] | 5:30 p.m. | T 0-0 | |
| Fri., 1/19 | V Boys Basketball | Shepaug Valley | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 67-60 | |
| Fri., 1/19 | JV Boys Basketball | Shepaug Valley | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 6:00 p.m. | W 62-23 | |
| Fri., 1/19 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 1/19 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Simsbury - ISCC-Olympic [Directions] | 7:00 p.m. | W 3-0 | |
| Sat., 1/20 | FR Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | Postponed | ||
| Sat., 1/20 | V Boys Ice Hockey | Eastern CT Eagles | Home - South Kent School-Ice Rink [Directions] | 5:30 p.m. | ||
| Sat., 1/20 | V Boys Indoor Track | Bethal | Away - Bethel HS Track & Field Training Center | TBA | ||
| Sat., 1/20 | V Boys Swimming and Diving | Nonnewaug | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:00 p.m. | ||
| Sat., 1/20 | V Wrestling | Arrigoni Classic | Away - Portland HS-Portland HS | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 1/20 | JV Girls Ice Hockey | Pope Francis (MA) | Home - Enfield Twin Rinks-Rink 1 [Directions] | 8:20 p.m. | W 3-0 | |
| Sat., 1/20 | V Girls Indoor Track | Bethel Invite | Away - Bethel HS Track & Field Training Center | TBA | ||
| Sun., 1/21 | JV Girls Ice Hockey | Longmeadow (MA) | Home - Simsbury - ISCC-Olympic [Directions] | 5:20 p.m. | W 4-0 | |
| Mon., 1/22 | V Boys Ice Hockey | McCann Tech (MA) | Home - South Kent School-Ice Rink [Directions] | 3:45 p.m. | W 7-4 | |
| Wed., 1/24 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | ||
| Wed., 1/24 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss School-Pool [Directions] | 5:30 p.m. | ||
| Wed., 1/24 | V Wrestling | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 1/24 | V Girls Ice Hockey | Southington Coop | Home - Simsbury - ISCC-Olympic [Directions] | 7:00 p.m. | W 1-0 | |
| Thu., 1/25 | V Boys Basketball | Thomaston | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 73-66 | |
| Thu., 1/25 | JV Boys Basketball | Thomaston | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/25 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 6:00 p.m. | L 42-46 | |
| Fri., 1/26 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | W 58-53 | |
| Fri., 1/26 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Terryville | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | W 52-22 | |
| Fri., 1/26 | JV Girls Ice Hockey | Longmeadow (MA) | Away - Smead Arena-Rink 1 | 5:00 p.m. | L 2-1 | |
| Sat., 1/27 | FR Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | Postponed | ||
| Sat., 1/27 | V Boys Swimming and Diving | Shepaug Valley | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:00 p.m. | ||
| Sat., 1/27 | V Wrestling | Rodney Smith Invitational | Away - Suffield HS | 7:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 1/27 | JV Girls Basketball | Housatonic Regional (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 2:30 p.m. | ||
| Sat., 1/27 | JV Girls Basketball | Indian Mountain School (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/27 | JV Girls Basketball | Dover (NY) (Scrim.) | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym | 5:30 p.m. | ||
| Mon., 1/29 | V Boys Ice Hockey | Newtown/New Fairfield | Home - South Kent School-Ice Rink [Directions] | 3:50 p.m. | ||
| Tue., 1/30 | V Boys Basketball | Nonnewaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 66-68 | |
| Tue., 1/30 | JV Boys Basketball | Nonnewaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:30 p.m. | W 58-53 | |
| Tue., 1/30 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/31 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | ||
| Wed., 1/31 | V Wrestling | Gilbert/Torrington | Home - Northwestern Regional H.S.-Small Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/31 | V Girls Ice Hockey | Simsbury | Away - Simsbury - ISCC-NHL [Directions] | 7:30 p.m. | W 6-5 | |
| Thu., 2/1 | JV Boys Basketball | Gilbert | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/1 | V Boys Swimming and Diving | Nonnewaug | Away - John F. Kennedy HS-JFK Pool [Directions] | 7:00 p.m. | ||
| Thu., 2/1 | JV Girls Basketball | Gilbert | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Basketball | Gilbert | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | W 61-27 | |
| Fri., 2/2 | V Girls Basketball | Gilbert | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:00 p.m. | W 66-40 | |
| Fri., 2/2 | JV Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 8:40 p.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | Tri-Town | Home - South Kent School-Ice Rink [Directions] | 7:40 p.m. | Remembrance Game | |
| Sat., 2/3 | JV Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Enfield Twin Rinks-Rink 1 [Directions] | 4:10 p.m. | W 7-0 | |
| Tue., 2/6 | V Boys Basketball | Wamogo | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | W 65-56 | |
| Tue., 2/6 | JV Boys Basketball | Wamogo | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Wamogo | Away - Wamogo HS-Large gym [Directions] | 6:00 p.m. | W 61-35 | |
| Tue., 2/6 | JV Girls Basketball | Wamogo | Away - Wamogo HS-Large gym [Directions] | Canceled | Cancelled | |
| Wed., 2/7 | V Boys Ice Hockey | New Milford | Away - Canterbury School-O'Neill Arena [Directions] | 7:45 p.m. | ||
| Wed., 2/7 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | W 3-1 | |
| Fri., 2/9 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | W 69-29 | |
| Fri., 2/9 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | V Boys Indoor Track | CIAC S Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Housatonic Regional | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:45 p.m. | W 55-32 | |
| Fri., 2/9 | JV Girls Basketball | Housatonic Regional | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | JV Girls Ice Hockey | Pope Francis (MA) | Away - Smead Arena-Rink | 7:00 p.m. | W 3-1 | |
| Fri., 2/9 | V Girls Indoor Track | CIAC S Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 2/10 | V Boys Basketball | Pomperaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | 2:30 p.m. | L 52-50 | |
| Sat., 2/10 | JV Boys Basketball | Pomperaug | Home - Northwestern Regional H.S.-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 2/10 | V Boys Swimming and Diving | Wamogo | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:00 p.m. | ||
| Sat., 2/10 | V Girls Ice Hockey | Woodstock Academy Coop | Away - Pomfret School-Jahn Rink [Directions] | 6:30 p.m. | W 7-3 | |
| Mon., 2/12 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - South Kent School-Ice Rink [Directions] | 3:50 p.m. | ||
| Mon., 2/12 | V Girls Basketball | SMSA | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:30 p.m. | W 70-50 | |
| Mon., 2/12 | JV Girls Basketball | SMSA | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/13 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/14 | V Boys Basketball | SMSA | Away - Sport and Medical Sciences Academy (SMSA)-Gym [Directions] | 6:45 p.m. | L 29-56 | |
| Wed., 2/14 | JV Boys Basketball | SMSA | Away - Sport and Medical Sciences Academy (SMSA)-Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | SMSA | Away - Sport and Medical Sciences Academy (SMSA)-Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | McCann Tech (MA) | Away - Mccann Techinical HS-Veterens Rink | 7:00 p.m. | ||
| Wed., 2/14 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/14 | V Girls Ice Hockey | East Catholic Coop | Home - Simsbury - ISCC-Olympic [Directions] | 7:00 p.m. | L 4-2 | |
| Thu., 2/15 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 4:00 p.m. | W 56-28 | |
| Fri., 2/16 | V Wrestling | CIAC S Divisional Championship | Away - Killingly | TBA | ||
| Fri., 2/16 | V Girls Basketball | Terryville | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | W 47-19 | |
| Fri., 2/16 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:15 p.m. | L 5-0 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Enfield Twin Rinks-Rink 1 [Directions] | 6:20 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Tue., 2/20 | V Boys Basketball | Litchfield | Home - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | W 80-74 | |
| Tue., 2/20 | JV Boys Basketball | Litchfield | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/20 | V Girls Basketball | Gilbert | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:15 p.m. | W 61-44 | |
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Fri., 2/23 | V Girls Basketball | Thomaston | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 41-36 | |
| Sat., 2/24 | V Boys Ice Hockey | Wilton | Home - South Kent School-Ice Rink [Directions] | 7:00 p.m. | ||
| Mon., 2/26 | V Boys Basketball | Terryville | Home - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/26 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - South Kent School-Ice Rink [Directions] | 3:50 p.m. | ||
| Mon., 2/26 | V Girls Ice Hockey | Hall/Conard | Home - Enfield Twin Rinks-Rink 1 [Directions] | 7:50 p.m. | W 2-1 | |
| Wed., 2/28 | V Boys Basketball | Shepaug Valley | Home - Thomaston HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/28 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks-Rink 2 [Directions] | 3:50 p.m. | ||
| Thu., 2/29 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Simsbury - ISCC-NHL [Directions] | 3:00 p.m. | ||
| Thu., 2/29 | V Girls Basketball | Platt Tech | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:30 p.m. | W 63-34 | |
| Thu., 2/29 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Fri., 3/1 | V Boys Basketball | Lewis Mills (Scrim.) | Away - Lewis Mills HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | Housatonic Regional, Litchfield, Nonnewaug, Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 5:30 p.m. | ||
| Sat., 3/2 | V Boys Swimming and Diving | Housatonic Regional, TBA, Nonnewaug, Shepaug Valley, Wamogo | Away - Hotchkiss School-Pool | 1:00 p.m. | ||
| Mon., 3/4 | V Boys Basketball | Sheehan | Home - Northwestern Regional H.S.-Main Gym [Directions] | 6:30 p.m. | L 52-58 | |
| Mon., 3/4 | V Boys Ice Hockey | CIAC Div III First Round | Away - Higher Seed | TBA | ||
| Mon., 3/4 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | L 28-54 | |
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 3/7 | V Boys Ice Hockey | CIAC Div III Quarterfinal | Away - Site TBA | TBA | ||
| Mon., 3/11 | V Boys Ice Hockey | CIAC Div III Semifinal | Away - Site TBA | TBA | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Ice Hockey | CIAC Div III Final | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Sat., 3/23 | V Baseball | Canton, Avon (Scrim.) | Away - Bowdoin Field-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Wed., 3/27 | V Baseball | Farmington (Scrim.) | Away - Tunxis Mead Park-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Sat., 3/30 | V Baseball | Avon (Scrim.) | Away - Buckingham Fields-90 ft. Baseball Diamond [Directions] | 10:30 a.m. | ||
| Sat., 3/30 | V Softball | Canton | Away - Canton HS-Softball Diamond [Directions] | 11:00 a.m. | L 21-24 | |
| Mon., 4/1 | V Boys Tennis | Housatonic Regional | Away - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 4/1 | V Girls Tennis | Housatonic Regional | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Fri., 4/5 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/5 | V Girls Tennis | Nonnewaug | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Sat., 4/6 | JV Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:30 p.m. | W 12-1 | |
| Sat., 4/6 | JV Softball | Housatonic Regional | Home - Housatonic Valley Regional High-softball field [Directions] | Canceled | Cancelled | |
| Sat., 4/6 | JV Softball | Housatonic Regional | Away - Housatonic Valley Regional High-Softball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 4/8 | V Baseball | Gilbert | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | W 15-0 | |
| Mon., 4/8 | JV Baseball | Canton | Away - Bowdoin Field-Baseball Diamond [Directions] | 4:30 p.m. | W 15-11 | |
| Mon., 4/8 | V Boys Tennis | Shepaug Valley | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 4/8 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 3:45 p.m. | W 10-3 | |
| Mon., 4/8 | JV Softball | Gilbert | Away - Rowley Field-Gilbert (Rowley Street) Field #1 [Directions] | 3:45 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/9 | V Baseball | Housatonic Regional | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 4/9 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | L 17-18 | |
| Wed., 4/10 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | W 12-0 | |
| Wed., 4/10 | V Softball | Terryville | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | W 19-4 | |
| Wed., 4/10 | V Girls Tennis | Gilbert | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/12 | JV Baseball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 4-5 8th | |
| Mon., 4/15 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | W 11-9 | |
| Mon., 4/15 | JV Baseball | Gilbert | Away - Walker Field-Walker Field (Baseball Field) [Directions] | 3:45 p.m. | W 18-3 | |
| Mon., 4/15 | V Softball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | W 19-4 | |
| Wed., 4/17 | V Baseball | Shepaug Valley | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | L 0-8 | |
| Wed., 4/17 | JV Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | W 9-2 | |
| Wed., 4/17 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 3:45 p.m. | L 8-11 | |
| Wed., 4/17 | JV Softball | Shepaug Valley | Away - Washington Primary School-Washington Primary School Softball Field [Directions] | Postponed | ||
| Thu., 4/18 | V Boys Outdoor Track | Terryville, Gilbert, Housatonic Regional, Litchfield, TBA, Thomaston, Wamogo | Away - Terryville HS-Track | Rainout | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Thu., 4/18 | V Girls Outdoor Track | Terryville, Gilbert, Housatonic Regional, Litchfield, TBA, Thomaston, Wamogo | Away - Terryville HS-Track | Rainout | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 4/19 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:30 p.m. | W 14-3 | |
| Fri., 4/19 | V Softball | Thomaston | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 4:00 p.m. | L 3-22 | |
| Mon., 4/22 | V Boys Tennis | Litchfield | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Mon., 4/22 | V Softball | Somers | Away - Somers HS-Somers High School Softball Field [Directions] | 4:00 p.m. | L 7-9 | |
| Mon., 4/22 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/23 | V Baseball | Wamogo | Away - Wamogo Regional HS-Fussenich Park [Directions] | 6:00 p.m. | W 5-0 | |
| Tue., 4/23 | V Boys Outdoor Track | Thomaston, Litchfield | Away - Thomaston HS-Nystrom Park [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Lewis Mills | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Tue., 4/23 | V Girls Outdoor Track | Thomaston, Litchfield | Away - Thomaston HS-Nystrom Park [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Softball | Wamogo/Litchfield | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | W 20-5 | |
| Tue., 4/23 | JV Softball | Wamogo/Litchfield | Home - Northwestern Regional H.S.-JV Softball Field [Directions] | Postponed | ||
| Wed., 4/24 | V Baseball | Canton | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 4/24 | JV Baseball | Canton | Away - Bowdoin Field-Baseball Diamond [Directions] | 3:45 p.m. | L 2-8 | |
| Wed., 4/24 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Wed., 4/24 | V Softball | Canton | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 4:00 p.m. | W 10-5 | |
| Wed., 4/24 | V Girls Tennis | Wamogo | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Thu., 4/25 | JV Softball | Canton | Home - Northwestern Regional H.S.-JV Softball Field [Directions] | Postponed | ||
| Fri., 4/26 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | W 7-2 | |
| Fri., 4/26 | JV Baseball | Shepaug Valley | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | W 13-8 | |
| Fri., 4/26 | V Boys Tennis | Housatonic Regional | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 2-3 [Detailed Results] | |
| Fri., 4/26 | V Softball | Housatonic Regional | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | W 15-14 | |
| Fri., 4/26 | V Girls Tennis | Housatonic Regional | Away - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 4/27 | V Baseball | Nonnewaug | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 11:00 a.m. | L 3-12 | |
| Sat., 4/27 | JV Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-JV Baseball Diamond [Directions] | 10:00 a.m. | W 12-3 | |
| Sat., 4/27 | V Boys Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 4/27 | V Girls Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 9:00 a.m. | ||
| Sat., 4/27 | JV Softball | Gilbert, Housatonic Regional, Nonnewaug | Home - Northwestern Regional H.S.-JV Softball Field [Directions] | 9:00 a.m. | ||
| Mon., 4/29 | V Baseball | Wamogo | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | W 14-11 | |
| Mon., 4/29 | V Boys Tennis | Nonnewaug | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 4/29 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 4:00 p.m. | W 14-13 | |
| Mon., 4/29 | JV Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Litchfield HS Softball Fields [Directions] | 3:45 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Gilbert, Nonnewaug | Home - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Thomaston | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 4-0 [Detailed Results] | |
| Tue., 4/30 | V Girls Outdoor Track | Gilbert, Nonnewaug | Home - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Softball | Gilbert | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | W 17-0 | |
| Tue., 4/30 | JV Softball | Gilbert | Home - Northwestern Regional H.S.-JV Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Baseball | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Shepaug Valley | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | V Baseball | Wolcott Tech | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | JV Baseball | Gilbert | Away - Walker Field-Walker Field (Baseball Field) [Directions] | 3:45 p.m. | W 11-1 | |
| Fri., 5/3 | V Boys Tennis | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | ||
| Fri., 5/3 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | ||
| Fri., 5/3 | V Girls Tennis | Thomaston | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 5/4 | JV Baseball | Housatonic Regional | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 10:00 a.m. | W 14-2 | |
| Sat., 5/4 | JV Softball | Housatonic Regional | Away - Housatonic Valley Regional High-Softball Diamond [Directions] | 9:00 a.m. | ||
| Mon., 5/6 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | Postponed | ||
| Mon., 5/6 | V Girls Tennis | Gilbert | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Baseball | Terryville | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Terryville, Wamogo | Home - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Terryville, Wamogo | Home - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Softball | Nonnewaug | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | JV Baseball | Nonnewaug | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | Postponed | ||
| Wed., 5/8 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Litchfield | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/9 | JV Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Boys Tennis | Wamogo | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 5/11 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 5/11 | JV Baseball | Wolcott | Away - Wolcott HS-Baseball Diamond [Directions] | 9:00 a.m. | ||
| Sat., 5/11 | V Boys Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Sat., 5/11 | JV Softball | Gilbert, Lewis Mills, Wamogo/Litchfield | Home - Northwestern Regional H.S.-JV Softball Field [Directions] | 9:00 a.m. | ||
| Sun., 5/12 | V Baseball | Wamogo | Away - Doubleday Field [Directions] | 10:00 a.m. | ||
| Mon., 5/13 | V Baseball | Lewis Mills | Away - Lewis Mills HS-Baseball Field - Varsity [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | JV Baseball | Lewis Mills | Away - Lewis Mills HS-Baseball Field - JV [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | Housatonic Regional, Shepaug Valley | Away - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | Housatonic Regional, Shepaug Valley | Away - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Softball | Wolcott Tech | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Canton | Home - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/14 | V Boys Tennis | Berkshire League Boys Tennis Championship | Away - Nonnewaug HS-Tennis Courts | 2:00 p.m. | ||
| Fri., 5/17 | V Baseball | Thomaston | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/17 | V Boys Tennis | Lewis Mills | Away - Lewis Mills HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/17 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 2:30 p.m. | ||
| Sat., 5/18 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 1:00 p.m. | ||
| Sat., 5/18 | JV Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-JV Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 5/18 | V Boys Outdoor Track | Berkshire League Track & Field Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 8:00 a.m. | ||
| Sat., 5/18 | V Girls Outdoor Track | Berkshire League Track & Field Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 8:00 a.m. | ||
| Sat., 5/18 | JV Softball | Wamogo/Litchfield | Home - Northwestern Regional H.S.-JV Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/20 | JV Baseball | Nonnewaug | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/20 | V Boys Tennis | Berkshire League Boys Tennis Championship Semi/Finals | Away - TBA | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Mon., 5/20 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - Nonnewaug HS-Tennis Courts | 8:15 a.m. | ||
| Tue., 5/21 | V Baseball | Avon | Away - Dunkin' Park (Hartford, CT)-Yard Goats [Directions] | 3:30 p.m. | ||
| Tue., 5/21 | 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) | Away - Plumb Hill Field Complex-Plumb Hill Track | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Time to 3:30 p.m., Facility to Thomaston Nystrom Park-Nystroms Park Track | ||||||
| Tue., 5/21 | 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) | Away - Thomaston Nystrom Park-Nystroms Park Track | 3:30 p.m. | ||
| Tue., 5/21 | V Softball | Somers | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/22 | JV Baseball | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/22 | 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-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | 3:30 p.m. | ||
| Wed., 5/22 | 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-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | 3:30 p.m. | ||
| Wed., 5/22 | V Softball | Shepaug Valley | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/22 | JV Softball | Shepaug Valley | Home - Northwestern Regional H.S.-JV Softball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/22 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - Nonnewaug HS-Tennis Courts | 1:00 p.m. | ||
| Fri., 5/24 | V Baseball | Litchfield | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 1:30 p.m. | ||
| Fri., 5/24 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 2:00 p.m. | ||
| Tue., 5/28 | V Baseball | ValleyReg/Westbrook | Home - Northwestern Regional H.S.-Fussnich park [Directions] | 3:30 p.m. | ||
| Tue., 5/28 | V Softball | Griswold | Away - Griswold HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/29 | V Baseball | St. Joseph | Home - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:30 p.m. | ||