| Housatonic Regional 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 416 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Mon., 8/28 | V Boys Golf | Gilbert | Home - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Wed., 8/30 | V Boys Soccer | Mt. Everett (MA) (Scrim.) | Away - Mt Everett HS-Mt. Everett V Soccer Field | W 5-0 | TBA | |
| Thu., 8/31 | V Boys Golf | Wamogo | Home - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Fri., 9/1 | V Football | Granby/Canton (Scrim.) | Away - Granby Memorial HS-Stadium Field [Directions] | 7:00 a.m. | ||
| Sun., 9/3 | V Girls Soccer | Granby Memorial, Enfield, Northwestern, Notre Dame-Fairfield, Simsbury, Suffield, Valley Regional | Away - Granby Memorial HS-Stadium Field | 8:00 a.m. | 7:00 AM | |
| 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] | L 13-45 | ||
| Fri., 9/8 | JV Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 7:00 p.m. | ||
| Fri., 9/8 | V Girls Volleyball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 3-1 [Detailed Results] | ||
| Fri., 9/8 | JV Girls Volleyball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/9 | V Boys Soccer | Shepaug Valley | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | L 3-6 | ||
| Sat., 9/9 | JV Boys Soccer | Shepaug Valley | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | Postponed | ||
| Sat., 9/9 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 7-0 | 8:30 AM | |
| Mon., 9/11 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | W Forfeit | 2:30 PM | |
| Mon., 9/11 | V Girls Soccer | Gilbert | Home - Housatonic Valley Regional High-Girls Practice Field [Directions] | W 8-2 | ||
| Mon., 9/11 | JV Girls Soccer | Gilbert | Home - Housatonic Valley Regional High-Girls Practice Field [Directions] | Cancelled | ||
| Tue., 9/12 | V Boys Cross Country | Northwestern, Wamogo | Home - Housatonic Valley Regional High-Football Field/Game Soccer/Track/Cross Country Start & Finish [Directions] | H-Nw 32-24 H-W 18-45 | ||
| Tue., 9/12 | V Boys Golf | Northwestern | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | 2:05 PM, Dismiss 1:50 PM | |
| Tue., 9/12 | V Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | L 0-3 | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 9/12 | V Girls Cross Country | Northwestern, Wamogo | Home - Housatonic Valley Regional High-Football Field/Game Soccer/Track/Cross Country Start & Finish [Directions] | H-NW 15-50 H-W 15-50 | ||
| Tue., 9/12 | V Girls Soccer | Thomaston | Home - Housatonic Valley Regional High-Girls Practice Field [Directions] | T 2-2 | ||
| Tue., 9/12 | JV Girls Soccer | Thomaston | Home - Housatonic Valley Regional High-JV Girls Soccer Field (formerly Varsity Field) [Directions] | Postponed | ||
| Tue., 9/12 | V Girls Volleyball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 3-0 | ||
| Tue., 9/12 | JV Girls Volleyball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | V Football | Kennedy | Home - Gilbert School-Football Field [Directions] | W 21-7 | ||
| Fri., 9/15 | V Boys Golf | Nonnewaug | Home - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Fri., 9/15 | V Boys Soccer | Litchfield | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | T 1-1 | ||
| Fri., 9/15 | V Girls Volleyball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 3-1 | ||
| Fri., 9/15 | JV Girls Volleyball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/16 | JV Football | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 10:00 a.m. | ||
| Sat., 9/16 | JV Girls Soccer | Wamogo (Scrim.) | Home - Housatonic Valley Regional High-Girls Practice Field [Directions] | 9:30 a.m. | ||
| Sat., 9/16 | JV Girls Soccer | Thomaston (Scrim.) | Home - Housatonic Valley Regional High-JV Girls Soccer Field (formerly Varsity Field) [Directions] | Cancelled | ||
| Sat., 9/16 | JV Girls Soccer | Thomaston | Home - Housatonic Valley Regional High-JV Girls Soccer Field (formerly Varsity Field) [Directions] | Cancelled | ||
| Mon., 9/18 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | W 5-2 | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 9/18 | V Girls Volleyball | Dover (NY) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | Postponed | ||
| Mon., 9/18 | JV Girls Volleyball | Dover (NY) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | Postponed | ||
| Tue., 9/19 | V Boys Golf | Shepaug Valley | Away - Lake Waramaug Country Club [Directions] | 3:00 p.m. | 1:55 PM, Dismiss 1:40 PM | |
| Tue., 9/19 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | L 1-2 | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 9/19 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | Cancelled | 12:00 PM | |
| Tue., 9/19 | V Girls Soccer | Nonnewaug | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | L 7-2 | ||
| Tue., 9/19 | JV Girls Soccer | Nonnewaug | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | W 3-2 | 3:50 PM | |
| Tue., 9/19 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | Cancelled | 3:30 PM | |
| Wed., 9/20 | V Boys Cross Country | 35th Annual - Going to the Sun Cross Country Invitational | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Wed., 9/20 | V Boys Golf | Litchfield | Away - Litchfield Country Club [Directions] | 3:00 p.m. | 2:00 PM | |
| Wed., 9/20 | V Girls Cross Country | 35th Annual - Going to the Sun Cross Country Invitational | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Thu., 9/21 | V Boys Golf | Wamogo | Away - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Thu., 9/21 | V Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | L 2-3 | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 9/21 | JV Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 9/22 | V Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | W 20-14 | ||
| Fri., 9/22 | V Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | W 6-0 | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 9/22 | V Girls Soccer | Wamogo | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W 8-0 | ||
| Fri., 9/22 | JV Girls Soccer | Wamogo | Home - Housatonic Valley Regional High-Girls Practice Field [Directions] | Postponed | ||
| Sat., 9/23 | JV Football | Torrington | Home - Gilbert School-Football Field [Directions] | 9:00 a.m. | ||
| Mon., 9/25 | JV Boys Soccer | Terryville | Home - Housatonic Valley Regional High-JV Boys Soccer (formerly Varsity Field) [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Housatonic Valley Regional High-Boys Practice Field | ||||||
| Tue., 9/26 | V Boys Cross Country | Litchfield, Terryville | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | H-L 33-22 H-T 15-46 | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 9/26 | V Boys Golf | Litchfield | Home - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Litchfield, Terryville | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | H-L 28-27 H-T 15-50 | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 9/26 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | L 0-3 | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 9/26 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Wed., 9/27 | JV Boys Soccer | Northwestern | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | 3:45 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Northwestern | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W 4-2 | ||
| Wed., 9/27 | JV Girls Soccer | Northwestern | Home - Housatonic Valley Regional High-Girls Practice Field [Directions] | 3:45 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | L 1-3 | 3:15 PM | |
| Wed., 9/27 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 4:15 p.m. | 2:45 PM | |
| Sat., 9/30 | V Football | Woodland | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | L 0-34 | ||
| Sat., 9/30 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | 8:45 AM | |
| Mon., 10/2 | JV Football | Woodland | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Boys Golf | Shepaug Valley | Home - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Mon., 10/2 | V Boys Soccer | Terryville | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W 2-1 | ||
| Mon., 10/2 | V Girls Volleyball | Dover (NY) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 2-3 | 2:45 PM | |
| Mon., 10/2 | JV Girls Volleyball | Dover (NY) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 10/3 | V Boys Cross Country | Gilbert, Nonnewaug | Away - Gilbert School-Cross Country [Directions] | H-G 15-50 H-N 36-25 | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/3 | V Boys Soccer | Gilbert | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W Forfeit | ||
| Tue., 10/3 | V Girls Cross Country | Gilbert, Nonnewaug | Away - Gilbert School-Cross Country [Directions] | H-G 15-50 H-N 33-22 | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/3 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | W 8-1 | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/3 | V Girls Volleyball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 0-3 | ||
| Tue., 10/3 | JV Girls Volleyball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Boys Golf | Gilbert | Away - Green woods Country Club [Directions] | 3:00 p.m. | 1:50 PM, Dismiss 1:40 PM | |
| Wed., 10/4 | JV Girls Soccer | Indian Mountain School | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:15 p.m. | ||
| Thu., 10/5 | V Boys Golf | Northwestern | Home - Canaan Country Club [Directions] | 3:00 p.m. | Senior Night | |
| Thu., 10/5 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 2-7 | 2:15 PM, Dismiss 2:00 PM | |
| Thu., 10/5 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | Postponed | 2:15 PM, Dismiss 2:00 PM | |
| Thu., 10/5 | V Girls Soccer | Shepaug Valley | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W 7-2 | ||
| Mon., 10/9 | V Football | Naugatuck | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | L 21-41 | ||
| Tue., 10/10 | V Boys Cross Country | Shepaug Valley, Thomaston | Home - Housatonic Valley Regional High-Football Field/Game Soccer/Track/Cross Country Start & Finish [Directions] | H-S 28-28 H-T 38-23 | Senior Night | |
| Tue., 10/10 | FM Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | 12:00 PM | |
| Tue., 10/10 | V Boys Golf | Nonnewaug | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM | |
| Tue., 10/10 | V Boys Soccer | Thomaston | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | L 1-2 | ||
| Tue., 10/10 | JV Boys Soccer | Thomaston | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | Postponed | ||
| Tue., 10/10 | V Girls Cross Country | Shepaug Valley, Thomaston | Home - Housatonic Valley Regional High-Football Field/Game Soccer/Track/Cross Country Start & Finish [Directions] | H-T 15-50 H-S 28-27 | Senior Night | |
| Tue., 10/10 | V Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | L 5-1 | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 10/10 | JV Girls Soccer | Thomaston | Away - Thomaston HS [Directions] | Cancelled | 2:15 PM | |
| Tue., 10/10 | V Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | W 3-0 | 2:45 PM | |
| Tue., 10/10 | JV Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | 4:30 p.m. | 2:45 PM | |
| Thu., 10/12 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | L 0-2 | 4:00 PM | |
| Fri., 10/13 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | L 0-4 | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 10/13 | V Girls Soccer | Litchfield | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W 6-1 | ||
| Fri., 10/13 | V Girls Volleyball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 3-1 | ||
| Fri., 10/13 | JV Girls Volleyball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/14 | JV Boys Soccer | Litchfield, Northwestern | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 11:00 a.m. | 9:45 AM | |
| Sat., 10/14 | JV Girls Soccer | Litchfield, Northwestern, Thomaston | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 9:00 a.m. | 7:45 AM | |
| Mon., 10/16 | V Boys Soccer | Northwestern | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | W 2-1 | ||
| Mon., 10/16 | JV Boys Soccer | Northwestern | Home - Housatonic Valley Regional High-Girls Practice Field [Directions] | Postponed | ||
| Mon., 10/16 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | W 2-0 | 2:30 PM | |
| Mon., 10/16 | JV Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 10/17 | V Boys Golf | Berkshire League Golf All-Star Tournament | Away - Fairfiew Farm Golf Course | 8:00 a.m. | 6:30 AM | |
| Tue., 10/17 | V Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large gym [Directions] | W 3-1 | 2:45 PM | |
| Tue., 10/17 | JV Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Wed., 10/18 | V Boys Soccer | Wamogo | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W 3-0 | ||
| Wed., 10/18 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | W 3-0 | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 10/18 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 10/19 | V Boys Cross Country | Thomaston, Gilbert, Litchfield, Nonnewaug, Northwestern, Shepaug Valley, Terryville, Wamogo | Away - Thomaston HS-Black Rock State Park | 2:45 p.m. | TBA | |
| Thu., 10/19 | V Girls Cross Country | Thomaston, Gilbert, Litchfield, Nonnewaug, Northwestern, Shepaug Valley, Terryville, Wamogo | Away - Thomaston HS-Black Rock State Park | 2:45 p.m. | TBA | |
| Fri., 10/20 | V Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | L 7-12 | ||
| Fri., 10/20 | V Girls Volleyball | Mt. Everett (MA) | Away - Mount Everett Regional-Gym | W 3-2 | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 10/20 | JV Girls Volleyball | Mt. Everett (MA) | Away - Mount Everett Regional-Gym | 3:30 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| 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. | ||
| Mon., 10/23 | V Girls Soccer | Terryville | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | T 2-2 | 2:15 PM | |
| Tue., 10/24 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | W 4-3 | 5:00 PM | |
| Tue., 10/24 | V Girls Volleyball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 0-3 | Senior Night | |
| Tue., 10/24 | JV Girls Volleyball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | W 2-1 | 2:15 PM, Dismiss 2:00 PM | |
| Wed., 10/25 | JV Boys Soccer | Indian Mountain School | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | Postponed | ||
| Wed., 10/25 | JV Girls Soccer | Indian Mountain School | Away - Indian Mountain School-Indian Mtn School | 3:45 p.m. | 2:25 PM, Dismiss 2:00 PM | Team will take route bus to game |
| Thu., 10/26 | JV Football | Seymour | Away - Seymour HS-turf field [Directions] | 5:30 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | L 1-2 | 2:15 PM, Dismiss 2:00 PM | |
| Thu., 10/26 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Fri., 10/27 | V Boys Soccer | Nonnewaug | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | L 0-1 | Senior Night | |
| Fri., 10/27 | JV Boys Soccer | Nonnewaug | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | 3:45 p.m. | ||
| Fri., 10/27 | V Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | L 0-3 | 2:45 PM | |
| Fri., 10/27 | JV Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park | 9:35 a.m. | 6:15 AM | |
| Sat., 10/28 | V Football | Seymour | Home - Gilbert School-Football Field [Directions] | W 20-7 | ||
| Sat., 10/28 | JV Boys Soccer | Litchfield | Home - Housatonic Valley Regional High-Boys Practice Field [Directions] | 9:00 a.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park | 9:00 a.m. | 6:15 AM | |
| Tue., 10/31 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:15 p.m. | 1:30 PM | |
| Wed., 11/1 | V Girls Volleyball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 1-3 | ||
| Wed., 11/1 | JV Girls Volleyball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 3:30 p.m. | ||
| Sat., 11/4 | V Football | Wolcott | Home - Gilbert School-Football Field [Directions] | W 49-14 | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | 12:00 PM, Dismiss 11:45 AM | |
| Mon., 11/6 | V Girls Soccer | Litchfield | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | W 3-1 | ||
| Mon., 11/6 | V Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:00 p.m. | 3:00 PM | |
| Tue., 11/7 | FM Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 11/7 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:30 p.m. | 3:45 PM | |
| Wed., 11/8 | V Girls Soccer | Terryville | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | L 4-3 | ||
| Sat., 11/11 | V Football | Holy Cross | Home - Gilbert School-Football Field [Directions] | W 14-7 | ||
| Mon., 11/13 | JV Football | Holy Cross | Home - Walker Field [Directions] | 5:00 p.m. | ||
| Tue., 11/21 | V Football | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | W 35-0 | ||
| Tue., 11/28 | V Football | Tolland | Away - Tolland HS-Stadium [Directions] | 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] | L 0-21 | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Mon., 12/4 | V Boys Basketball | Derby (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/6 | V Girls Basketball | East Granby (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/7 | V Boys Basketball | Pine Plains (NY) (Scrim.) | Away - Pine Plains High/MS-Gym | 6:00 p.m. | 3:00 PM | |
| Thu., 12/7 | JV Boys Basketball | Pine Plains (NY) (Scrim.) | Away - Pine Plains High/MS-Gym | 4:15 p.m. | 3:00 PM | |
| Thu., 12/7 | V Girls Basketball | Torrington (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:00 p.m. | ||
| Sat., 12/9 | V Boys Basketball | TBA | Away - Warren Harding HS | 10:55 a.m. | 8:15 AM | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Tue., 12/12 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | L 55-24 | 4:00 PM | |
| Tue., 12/12 | JV Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Wed., 12/13 | V Boys Basketball | Canton (Scrim.) | Away - Canton HS-Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Wed., 12/13 | V Boys Ice Hockey | JBWA | Home - South Kent School-Ice Rink [Directions] | L 1-5 | ||
| Thu., 12/14 | V Boys Basketball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 53-74 | ||
| Thu., 12/14 | JV Boys Basketball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/14 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | W 45-26 | 3:45 PM | |
| Thu., 12/14 | JV Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | 3:45 PM | |
| Sat., 12/16 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | L 3-12 | 1:45 PM (Charter Bus) | |
| Tue., 12/19 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | L 47 - 97 | 3:00 PM | |
| Tue., 12/19 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | Postponed | 3:00 PM | |
| Wed., 12/20 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | L 2-5 | 3:15 PM | |
| Thu., 12/21 | V Boys Basketball | East Windsor | Away - East Windsor Senior HS-Gym [Directions] | L 43 - 51 | 3:15 PM | |
| Thu., 12/21 | JV Boys Basketball | East Windsor | Away - East Windsor Senior HS-Gym [Directions] | 5:30 p.m. | 3:15 PM | |
| Thu., 12/21 | V Girls Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 41-24 | ||
| Thu., 12/21 | JV Girls Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/22 | JV Boys Basketball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 3:45 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | L 34-41 | 4:45 PM | |
| Fri., 12/22 | JV Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | Cancelled | 4:15 PM | |
| Sat., 12/23 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | L 2-7 | 1:15 PM | |
| Wed., 12/27 | V Boys Basketball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 70 - 51 | ||
| Fri., 12/29 | V Boys Basketball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 50 - 70 | ||
| Tue., 1/2 | V Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | L 37-58 | 4:15 PM | |
| Tue., 1/2 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | 4:15 PM | |
| Tue., 1/2 | V Girls Basketball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 66-25 | ||
| Tue., 1/2 | JV Girls Basketball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | Postponed | ||
| Wed., 1/3 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - South Kent School-Ice Rink [Directions] | L 4-5 | ||
| Thu., 1/4 | V Boys Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | L 66 - 68 | 3:30 PM | |
| Thu., 1/4 | JV Boys Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | 5:30 p.m. | 3:30 PM | |
| Thu., 1/4 | FR Boys Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | Cancelled | 2:00 PM (Not sure if having Freshmen team. If not bus will be at 3:30) | |
| Thu., 1/4 | V Girls Basketball | Lewis Mills | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 25-38 | ||
| Thu., 1/4 | JV Girls Basketball | Lewis Mills | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Northwestern | Away - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:00 p.m. | 5:30 PM | Warm up 6:30 |
| Fri., 1/5 | V Girls Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | W 68-20 | 4:15 PM | |
| Mon., 1/8 | V Boys Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 57 - 79 | ||
| Mon., 1/8 | JV Boys Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/8 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - South Kent School-Ice Rink [Directions] | L 1-9 | 2:10 PM | |
| Mon., 1/8 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | W 50-35 | 4:30 PM | |
| Mon., 1/8 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:45 p.m. | 4:30 PM | |
| Wed., 1/10 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | L 34 - 73 | 4:15 PM | |
| Wed., 1/10 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | 4:15 PM | |
| Wed., 1/10 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | L 0-2 | 6:45 PM (May not need - parent transport) | |
| Wed., 1/10 | V Boys Swimming and Diving | Nonnewaug | Home - Hotchkiss School-Pool [Directions] | 5:30 p.m. | warm up 5:00 | |
| Wed., 1/10 | V Girls Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 52-26 | ||
| Wed., 1/10 | JV Girls Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | Cancelled | ||
| Fri., 1/12 | V Boys Basketball | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 49 - 83 | ||
| Fri., 1/12 | JV Boys Basketball | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 46-21 | 4:15 PM | |
| Fri., 1/12 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Cancelled | 4:00 PM | |
| Sat., 1/13 | JV Boys Basketball | Nonnewaug (Scrim.) | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 2:30 p.m. | ||
| Sat., 1/13 | JV Boys Basketball | Shepaug Valley (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:45 p.m. | ||
| Sat., 1/13 | JV Boys Basketball | Indian Mountain School (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:15 p.m. | ||
| Mon., 1/15 | V Girls Basketball | SMSA | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 51-49 | ||
| Mon., 1/15 | JV Girls Basketball | SMSA | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 3:00 p.m. | ||
| Wed., 1/17 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Simsbury - ISCC-Olympic [Directions] | 7:00 p.m. | 4:30 PM | |
| Wed., 1/17 | V Boys Swimming and Diving | Shepaug Valley | Home - Hotchkiss School-Pool [Directions] | 5:30 p.m. | warm up 5:00 | |
| Thu., 1/18 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | L 64 - 97 | 4:00 PM | |
| Thu., 1/18 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | 4:05 PM | |
| Thu., 1/18 | V Girls Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 28-53 | ||
| Thu., 1/18 | JV Girls Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | L 48 - 71 | 3:45 PM | |
| Fri., 1/19 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | 3:45 PM | |
| Fri., 1/19 | V Girls Basketball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 53-47 | ||
| Fri., 1/19 | JV Girls Basketball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/20 | FR Boys Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 2:30 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | Eastern CT Eagles | Home - South Kent School-Ice Rink [Directions] | 5:30 p.m. | ||
| Mon., 1/22 | V Boys Ice Hockey | McCann Tech (MA) | Home - South Kent School-Ice Rink [Directions] | 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 | Northwestern | Home - Hotchkiss School-Pool [Directions] | 5:30 p.m. | warm up 5:00 | |
| Thu., 1/25 | V Boys Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 70 - 48 | ||
| Thu., 1/25 | JV Boys Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/25 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | L 54-36 | 3:00 PM | |
| Thu., 1/25 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | 3:00 PM | |
| Fri., 1/26 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | W 69 - 51 | 4:15 PM | |
| Fri., 1/26 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:30 p.m. | 4:15 PM | |
| Fri., 1/26 | V Girls Basketball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 57-44 | ||
| Fri., 1/26 | JV Girls Basketball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/27 | JV Girls Basketball | Northwestern (Scrim.) | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 2:30 p.m. | ||
| Sat., 1/27 | JV Girls Basketball | Dover (NY) (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:45 p.m. | ||
| Sat., 1/27 | JV Girls Basketball | Indian Mountain School (Scrim.) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:15 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 | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 51-62 | ||
| Tue., 1/30 | JV Boys Basketball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | W 45-30 | 4:30 PM | |
| Tue., 1/30 | JV Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | Cancelled | 4:15 PM | |
| Wed., 1/31 | JV Boys Basketball | Mt. Everett (MA) | Away - Mount Everett Regional-Gym | 5:30 p.m. | 2:45 PM | |
| Wed., 1/31 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | 5:45 PM | |
| Wed., 1/31 | V Boys Swimming and Diving | Litchfield | Home - Hotchkiss School-Pool [Directions] | 5:30 p.m. | warm up 5:00 | |
| Wed., 1/31 | JV Girls Basketball | Mt. Everett (MA) | Away - Mount Everett Regional-Gym | 4:00 p.m. | 2:45 PM | |
| Fri., 2/2 | V Boys Basketball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 47 - 34 | ||
| Fri., 2/2 | V Girls Basketball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 34-8 | ||
| Sat., 2/3 | V Boys Ice Hockey | Tri-Town | Home - South Kent School-Ice Rink [Directions] | 7:40 p.m. | Remembrance Game | |
| Mon., 2/5 | JV Girls Basketball | Dover (NY) (Scrim.) | Away - Dover HS-Gym | 4:15 p.m. | 2:45 PM | |
| Tue., 2/6 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | L 44-72 | 4:15 PM | |
| Tue., 2/6 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | 4:15 PM | |
| Tue., 2/6 | FR Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | Cancelled | 2:30 PM (may not have team.) | |
| Tue., 2/6 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | 2:45 PM | Warm up 4:00 |
| Tue., 2/6 | V Girls Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 50-21 | ||
| Tue., 2/6 | JV Girls Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | Cancelled | ||
| Wed., 2/7 | FR Boys Basketball | Indian Mountain School | Away - Indian Mountain School-#4 | 3:30 p.m. | ||
| Wed., 2/7 | V Boys Ice Hockey | New Milford | Away - Canterbury School-O'Neill Arena [Directions] | 7:45 p.m. | 5:45 PM | |
| Wed., 2/7 | V Boys Swimming and Diving | Wamogo | Home - Hotchkiss School-Pool [Directions] | 4:30 p.m. | warm up 4:00 | |
| Fri., 2/9 | V Boys Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 29-69 | ||
| Fri., 2/9 | JV Boys Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Nonnewaug | Away - John F. Kennedy HS-JFK Pool [Directions] | 7:00 p.m. | 5:00 PM | Warm up 6:30 |
| Fri., 2/9 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | L 55-32 | 4:15 PM | |
| Fri., 2/9 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | 4:15 PM | |
| 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 | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 41-32 | ||
| Tue., 2/13 | JV Girls Basketball | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | Cancelled | ||
| Wed., 2/14 | V Boys Ice Hockey | McCann Tech (MA) | Away - Mccann Techinical HS-Veterens Rink | 7:00 p.m. | 3:45 PM | |
| Fri., 2/16 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 42-80 | 4:00 PM | |
| Fri., 2/16 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 2/16 | V Girls Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 34-31 | ||
| Tue., 2/20 | V Girls Basketball | Thomaston | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | 4:00 PM | |
| Wed., 2/21 | V Boys Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | L 60-62 | ||
| Wed., 2/21 | JV Boys Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | V Co-ed Alpine Skiing | TBA | Home - Mohawk Mountain Ski area [Directions] | TBA | BHSL Championship | |
| Wed., 2/21 | JV Girls Basketball | Indian Mountain School | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 3:15 p.m. | ||
| Thu., 2/22 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 5:30 p.m. | 4:15 PM | |
| 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 | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | 4:00 PM | |
| 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 Boys Swimming and Diving | Wamogo | Away - Wamogo Regional HS-Shepaug High School [Directions] | 7:00 p.m. | 5:15 PM | |
| Mon., 2/26 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | L 45-46 | 3:45 PM | |
| Wed., 2/28 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks-Rink 2 [Directions] | 3:50 p.m. | 12:30 PM, Dismiss 12:15 PM | |
| Thu., 2/29 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Simsbury - ISCC-NHL [Directions] | 3:00 p.m. | 12:30 PM, Dismiss 12:15 PM | |
| Fri., 3/1 | V Boys Swimming and Diving | Litchfield, Nonnewaug, Northwestern, Shepaug Valley, Wamogo | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 5:30 p.m. | Warm up 5:00 | |
| Sat., 3/2 | V Boys Swimming and Diving | TBA, Nonnewaug, Northwestern, Shepaug Valley, Wamogo | Home - Hotchkiss School-Pool [Directions] | 1:00 p.m. | ||
| Mon., 3/4 | V Boys Ice Hockey | CIAC Div III First Round | Away - Higher Seed | TBA | ||
| 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 | ||
| Thu., 3/14 | V Boys Ice Hockey | CIAC Div III Final | Away - Site TBA | TBA | ||
| Tue., 3/26 | V Baseball | Gilbert (Scrim.) | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | V Softball | Wolcott Tech (Scrim.) | Home - Housatonic Valley Regional High-softball field [Directions] | W 12-0 | ||
| Thu., 3/28 | V Baseball | Canton (Scrim.) | Away - Bowdoin Field-Baseball Diamond [Directions] | Cancelled | 2:15 PM, Dismiss 2:00 PM | |
| Sat., 3/30 | V Softball | Wilcox Tech | Home - Housatonic Valley Regional High-softball field [Directions] | L 15-2 | ||
| Mon., 4/1 | V Boys Tennis | Northwestern | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 4/1 | V Girls Lacrosse | Haddam-Killingworth | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | L 0-7 | 2:20 PM, Dismiss 2:05 PM | |
| Sat., 4/6 | JV Baseball | Derby | Away - Payden Park [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | JV Softball | Northwestern | Away - Housatonic Valley Regional High-softball field [Directions] | Cancelled | ||
| Sat., 4/6 | JV Softball | Northwestern | Home - Housatonic Valley Regional High-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/8 | V Baseball | Wamogo | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | L 6-0 | ||
| Mon., 4/8 | V Boys Tennis | Litchfield | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 4/8 | V Girls Lacrosse | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 4/8 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | W 25-4 | 3:30 PM | |
| Mon., 4/8 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | 2:20 PM, Dismiss 2:05 PM | |
| Tue., 4/9 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 4/9 | V Boys Tennis | Shepaug Valley | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | 2:25 PM | |
| Tue., 4/9 | V Softball | Northwestern | Home - Housatonic Valley Regional High-softball field [Directions] | W 18-17 | ||
| Tue., 4/9 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Wed., 4/10 | V Baseball | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 4/10 | V Boys Tennis | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | 2:10 PM | |
| Wed., 4/10 | V Girls Lacrosse | Berkshire (MA) (Scrim.) | Away - Berkshire School | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 4/10 | V Softball | Gilbert | Home - Housatonic Valley Regional High-softball field [Directions] | W 20-5 | ||
| Mon., 4/15 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | 2:15 PM | |
| Mon., 4/15 | V Softball | Nonnewaug | Home - Housatonic Valley Regional High-softball field [Directions] | L 15-1 | ||
| Tue., 4/16 | V Baseball | Terryville | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | ||
| Tue., 4/16 | V Softball | Away - Terryville HS-Softball Field | W 34-8 | 2:45 PM | ||
| Wed., 4/17 | V Baseball | Litchfield | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | ||
| Thu., 4/18 | V Boys Outdoor Track | Terryville, Gilbert, Litchfield, TBA, Northwestern, Thomaston, Wamogo | Away - Terryville HS-Track | Rainout | 2:15 PM | |
| 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, Litchfield, TBA, Northwestern, Thomaston, Wamogo | Away - Terryville HS-Track | Rainout | 2:15 PM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 4/19 | V Baseball | Shepaug Valley | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | ||
| Fri., 4/19 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | L 9-1 | 2:45 PM | |
| Mon., 4/22 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:30 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Mon., 4/22 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | 2:20 PM, Dismiss 2:10 PM | |
| Mon., 4/22 | V Girls Lacrosse | St. Paul Catholic | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 4:45 p.m. | ||
| Mon., 4/22 | V Softball | Thomaston | Home - Housatonic Valley Regional High-softball field [Directions] | L 8-6 | ||
| Mon., 4/22 | V Girls Tennis | Wamogo | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Baseball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Baseball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-JV Baseball Diamond [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Tue., 4/23 | V Boys Outdoor Track | Wamogo, Nonnewaug | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 4/23 | V Girls Lacrosse | Litchfield Coop | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 5:15 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Wamogo, Nonnewaug | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 4/24 | V Softball | East Granby | Home - Housatonic Valley Regional High-softball field [Directions] | W 8-5 | ||
| Wed., 4/24 | V Girls Tennis | Gilbert | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/26 | V Baseball | Northwestern | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | ||
| Fri., 4/26 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | 2:20 PM, Dismiss 2:10 PM | |
| Fri., 4/26 | V Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | 3:30 PM | |
| Fri., 4/26 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | L 15-14 | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 4/26 | V Girls Tennis | Northwestern | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 4/27 | JV Baseball | Northwestern | Home - Housatonic Valley Regional High-JV Baseball Diamond [Directions] | 10:00 a.m. | 8:45 AM | |
| Sat., 4/27 | JV Softball | Northwestern, Gilbert, Nonnewaug | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | 9:00 a.m. | 7:45 AM | |
| Sat., 4/27 | JV Softball | Nonnewaug | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 9:00 a.m. | 7:45 AM | |
| Mon., 4/29 | JV Baseball | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | 2:10 PM, Dismiss 2:00 PM | |
| Mon., 4/29 | V Softball | Windsor Locks | Home - Housatonic Valley Regional High-softball field [Directions] | W 10-3 | Strike out for Cancer Game | |
| Mon., 4/29 | V Girls Tennis | Shepaug Valley | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Litchfield, Terryville | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 4/30 | V Girls Lacrosse | Wolcott | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Litchfield, Terryville | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 5/1 | V Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 5/1 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | 2:20 PM, Dismiss 2:10 PM | |
| Wed., 5/1 | V Softball | Wamogo/Litchfield | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Litchfield | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 4:30 p.m. | 2:50 PM | |
| Thu., 5/2 | V Softball | Webutuck (NY) | Home - Housatonic Valley Regional High-softball field [Directions] | W 16-3 | ||
| Fri., 5/3 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | 2:10 PM, Dismiss 2:00 PM | |
| Fri., 5/3 | V Girls Lacrosse | Litchfield Coop | Away - Nonnewaug HS-Nonnewaug Track [Directions] | 5:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 5/3 | V Girls Tennis | Nonnewaug | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | Senior Day | |
| Sat., 5/4 | JV Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 10:00 a.m. | 8:45 AM | |
| Sat., 5/4 | JV Softball | Northwestern | Home - Housatonic Valley Regional High-Softball Diamond [Directions] | 9:00 a.m. | ||
| Mon., 5/6 | V Baseball | Gilbert | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Thomaston | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:00 p.m. | 3:15 PM | |
| Mon., 5/6 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 4:15 p.m. | 3:00 PM | |
| Mon., 5/6 | V Girls Tennis | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 5/7 | V Boys Outdoor Track | Gilbert, Mt. Everett (MA), Thomaston | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Nonnewaug | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | 2:25 PM | |
| Tue., 5/7 | V Girls Outdoor Track | Gilbert, Mt. Everett (MA), Thomaston | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | 2:15 PM | |
| Wed., 5/8 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Wed., 5/8 | V Boys Tennis | Wamogo | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Girls Lacrosse | Granby Memorial | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Terryville | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | 2:20 PM, Dismiss 2:05 PM | |
| Thu., 5/9 | V Baseball | Nonnewaug | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Lewis Mills | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | Senior Day | |
| Thu., 5/9 | V Girls Lacrosse | Watertown | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 4:00 p.m. | Senior Day | |
| Thu., 5/9 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:15 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 5/9 | V Girls Tennis | Gilbert | Away - Walker Field-Tennis Courts [Directions] | 3:45 p.m. | 2:20 PM, Dismiss 2:05 PM | |
| Sat., 5/11 | V Boys Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Sat., 5/11 | V Boys Outdoor Track | TBA | Away - Torrington HS | TBA | 8:30 AM, Dismiss TBA | Torrington Invitational |
| Sat., 5/11 | V Girls Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Mon., 5/13 | V Baseball | Mt. Everett (MA) | Away - Mt Everett HS-Mt Everett Baseball | 4:00 p.m. | 3:00 PM | |
| Mon., 5/13 | JV Baseball | Mt. Everett (MA) | Away - Mt Everett HS-Mt Everett JV Baseball | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | Northwestern, Shepaug Valley | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:45 p.m. | Senior Day | |
| Mon., 5/13 | V Girls Outdoor Track | Northwestern, Shepaug Valley | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:45 p.m. | Senior Day | |
| Mon., 5/13 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 4:15 p.m. | 2:45 PM | |
| Tue., 5/14 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 5/14 | V Boys Tennis | Berkshire League Boys Tennis Championship | Home - TBA [Directions] | 8:00 a.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Time to 2:00 p.m., Facility to Nonnewaug HS-Tennis Courts | ||||||
| Tue., 5/14 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 4:15 p.m. | 3:00 PM | |
| Thu., 5/16 | V Girls Tennis | Thomaston | Home - Town Field-Town Tennis Courts [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 5/17 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Fri., 5/17 | JV Baseball | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | Cancelled | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 5/17 | V Softball | Shepaug Valley | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | Senior Day | |
| Fri., 5/17 | V Girls Tennis | Berkshire League Girls Tennis Championship Semi/Finals | Home - Nonnewaug HS-Paul Burns Memorial Track [Directions] | 2:00 p.m. | ||
| Sat., 5/18 | JV Baseball | Northwestern | Home - 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. | TBA | |
| 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 | Northwestern, Gilbert, Wamogo/Litchfield | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | 9:00 a.m. | ||
| Sat., 5/18 | JV Softball | Wamogo/Litchfield | Home - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 9:00 a.m. | ||
| Mon., 5/20 | V Baseball | Thomaston | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | Senior Day | |
| Mon., 5/20 | V Boys Tennis | Berkshire League Boys Tennis Championship Semi/Finals | Home - TBA [Directions] | 1:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to TBA | ||||||
| Mon., 5/20 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Home - Nonnewaug HS-Tennis Courts [Directions] | 8:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:15 a.m. | ||||||
| Tue., 5/21 | V Baseball | Webutuck (NY) | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 4:30 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) | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| 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) | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 3:30 p.m. | ||
| Tue., 5/21 | V Softball | Granby Memorial | Away - Granby Memorial HS-Softball Diamond [Directions] | 4:30 p.m. | 2:45 PM | |
| 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) | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 3:30 p.m. | ||
| Wed., 5/22 | V Boys Tennis | Berkshire League BoysTennis Tournament | Home - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 1:00 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) | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | ||||||
| Wed., 5/22 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Home - Nonnewaug HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Sat., 6/1 | V Softball | Alumni Game | Home - Housatonic Valley Regional High-softball field [Directions] | 11:00 a.m. | Alumni Game | |
| Sun., 6/9 | V Girls Lacrosse | Alumni Game | Home - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 11:00 a.m. | Alumni Game | |