| Gilbert 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 454 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Terryville | Home - Gilbert [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | TBA | ||
| TBA | FR Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | TBA | 2:30 | |
| TBA | FR Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | TBA | ||
| TBA | FR Girls Basketball | East Granby | Home - Gilbert Gym [Directions] | TBA | ||
| Thu., 9/3 | V Girls Volleyball | Torrington (Scrim.) | Away - Torrington HS [Directions] | 3:30 p.m. | 2:30 | |
| Fri., 9/4 | V Boys Soccer | East Granby (Scrim.) | Away - East Granby HS [Directions] | 4:00 p.m. | 2:45 | |
| Fri., 9/4 | V Girls Soccer | Derby (Scrim.) | Home - Walker Field [Directions] | 4:00 p.m. | ||
| Sat., 9/5 | V Boys Soccer | Hale Ray Jamboree | Away - Hale Ray HS | 10:00 a.m. | 8:00 | |
| Mon., 9/7 | V Girls Soccer | Granby Memorial (Scrim.) | Away [Directions] | 10:00 a.m. | 8:30 a.m. | |
| Tue., 9/8 | V Boys Cross Country | BL Scrimmage | Away - Black Rock State Park | TBA | 2:30 | |
| Tue., 9/8 | V Boys Soccer | Wolcott Tech (Scrim.) | Home - Walker Field [Directions] | 3:30 p.m. | ||
| Tue., 9/8 | V Girls Cross Country | BL Scrimmage | Away - Black Rock State Park | TBA | 2:30 | |
| Fri., 9/11 | V Boys Soccer | Terryville | Away - New Terryville HS [Directions] | L 0-2 | 2:30 | |
| Fri., 9/11 | JV Boys Soccer | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | 2:30 | |
| Fri., 9/11 | V Girls Soccer | Terryville | Home - Walker Field [Directions] | L 0-7 | ||
| Sat., 9/12 | V Football | Granby/Canton | Home - Gilbert [Directions] | L 0-42 | ||
| Mon., 9/14 | JV Football | Granby/Canton | Away - Ahrens Park Field [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 9/15 | V Boys Cross Country | Lewis Mills, Shepaug Valley | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Tue., 9/15 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | L 0-2 | ||
| Tue., 9/15 | JV Boys Soccer | Housatonic Regional | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 9/15 | V Girls Cross Country | Lewis Mills, Shepaug Valley | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Tue., 9/15 | V Girls Soccer | Housatonic Regional | Away - HS Field [Directions] | L 0-8 | 2:30 | |
| Tue., 9/15 | V Girls Volleyball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | L 2-3 | 2:30 | |
| Tue., 9/15 | JV Girls Volleyball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 9/16 | V Girls Volleyball | Putnam | Home - Gilbert Gym [Directions] | W 3-1 | ||
| Wed., 9/16 | JV Girls Volleyball | Putnam | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/18 | V Boys Soccer | Litchfield | Home - Walker Field [Directions] | L 1-7 | ||
| Fri., 9/18 | JV Boys Soccer | Litchfield | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 9/18 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | L 0-4 | 2:30 | |
| Fri., 9/18 | V Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | L 1-3 | ||
| Fri., 9/18 | JV Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/19 | V Boys Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | TBA | TBD | |
| Sat., 9/19 | V Football | Nonnewaug | Home - Gilbert [Directions] | W 20-14 | ||
| Sat., 9/19 | V Girls Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | TBA | TBD | |
| Mon., 9/21 | JV Football | Nonnewaug | Away - Nonnewaug HS Football Field [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 9/21 | V Boys Soccer | Thomaston | Away - Highwood Farms Field [Directions] | L 0-2 | 2:30 | |
| Mon., 9/21 | JV Boys Soccer | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | 2:30 | |
| Mon., 9/21 | V Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | L 1-3 | 3:15 (Drop Off Only) | |
| Mon., 9/21 | JV Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | 4:00 p.m. | 3:15 (Drop Off Only) | |
| Tue., 9/22 | V Boys Cross Country | Litchfield, Shepaug Valley, Terryville | Away - Plumb Hill Field Complex [Directions] | 4:00 p.m. | 2:40 | |
| Tue., 9/22 | V Girls Cross Country | Litchfield, Shepaug Valley, Terryville | Away - Plumb Hill Field Complex [Directions] | 4:00 p.m. | 2:40 | |
| Tue., 9/22 | V Girls Soccer | Thomaston | Home - Walker Field [Directions] | L 0-1 | ||
| Tue., 9/22 | V Girls Volleyball | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | L 0-3 | 2:30 | |
| Tue., 9/22 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 4:00 p.m. | 2:30 | |
| Thu., 9/24 | V Girls Volleyball | Terryville | Home - Gilbert Gym [Directions] | W 3-2 | ||
| Thu., 9/24 | JV Girls Volleyball | Terryville | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/25 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | L 1-3 | ||
| Fri., 9/25 | JV Boys Soccer | Wamogo | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 9/25 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | W 5-3 | 2:30 | |
| Fri., 9/25 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS [Directions] | Cancelled | ||
| Sat., 9/26 | V Boys Cross Country | Winding Trails Invt. | Away - Farmington | TBA | TBA | |
| Sat., 9/26 | V Football | Lewis Mills | Away - Lewis Mills Track [Directions] | W 34-7 | 11:00 | |
| Sat., 9/26 | V Girls Cross Country | Winding Trails Invt. | Away - Farmington | TBA | TBA | |
| Mon., 9/28 | JV Football | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Mon., 9/28 | V Girls Volleyball | Cheney Tech | Away - Cheney Tech [Directions] | W 3-1 | ||
| Mon., 9/28 | JV Girls Volleyball | Cheney Tech | Away - Cheney Tech [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Boys Cross Country | Terryville, Nonnewaug, Northwestern | Away [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 9/29 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | W 3-2 | ||
| Tue., 9/29 | JV Boys Soccer | Shepaug Valley | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 9/29 | V Girls Cross Country | Terryville, Nonnewaug, Northwestern | Away [Directions] | 2:30 | ||
| Tue., 9/29 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | L 0-7 | 2:30 | |
| Thu., 10/1 | V Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym Volleyball Court [Directions] | L 1-3 | 2:45 | |
| Thu., 10/1 | JV Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym Volleyball Court [Directions] | 3:45 p.m. | 2:45 | |
| Fri., 10/2 | V Boys Cross Country | Wamogo | Away - White Memorial (HS XC Course) [Directions] | 4:15 p.m. | 2:40 | |
| Fri., 10/2 | V Football | Canton | Away - Canton H.S. Turf [Directions] | W 29-7 | 5:00 | |
| Fri., 10/2 | V Boys Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | L 1-4 | No bus | No bus |
| Fri., 10/2 | JV Boys Soccer | Northwestern | Away - Northwestern JV field [Directions] | 5:00 p.m. | No bus | No bus |
| Fri., 10/2 | V Girls Cross Country | Wamogo | Away - White Memorial (HS XC Course) [Directions] | 4:15 p.m. | 2:40 | |
| Fri., 10/2 | V Girls Soccer | Northwestern | Away - Northwestern Field [Directions] | L 1-6 | No Bus | |
| Fri., 10/2 | V Girls Volleyball | Putnam | Away - Putnam HS Gymnasium [Directions] | W 3-1 | ||
| Fri., 10/2 | JV Girls Volleyball | Putnam | Away - Putnam HS Gymnasium [Directions] | Cancelled | ||
| Mon., 10/5 | JV Football | Canton | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Boys Cross Country | Thomaston, Nonnewaug, Litchfield | Away - Black Rock State Park [Directions] | 4:15 p.m. | 2:30 | |
| Tue., 10/6 | V Boys Soccer | Nonnewaug | Away - NHS - Varsity Soccer Field [Directions] | L 0-10 | 2:30 | |
| Tue., 10/6 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 10/6 | V Girls Cross Country | Thomaston, Nonnewaug, Litchfield | Away - Black Rock State Park [Directions] | 4:15 p.m. | 2:30 | |
| Tue., 10/6 | V Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | L 7-1 | ||
| Tue., 10/6 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L 0-3 | 2:30 | |
| Tue., 10/6 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | 2:30 | |
| Thu., 10/8 | V Boys Soccer | Lewis Mills | Away - Lewis Mills Track [Directions] | L 1-6 | 3:15 | |
| Thu., 10/8 | JV Boys Soccer | Lewis Mills | Away - Lewis Mills JV Soccer Field [Directions] | 3:45 p.m. | 3:15 | |
| Thu., 10/8 | V Girls Soccer | Lewis Mills | Home - Walker Field [Directions] | L 8-0 | ||
| Fri., 10/9 | V Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | W 3-0 | ||
| Fri., 10/9 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/10 | V Football | Creed | Home - Gilbert [Directions] | L 10-20 | Homecoming | |
| Mon., 10/12 | JV Football | Creed | Away - Blake Field | Cancelled | ||
| Mon., 10/12 | V Girls Volleyball | Kennedy | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Mon., 10/12 | JV Girls Volleyball | Kennedy | Home - Gilbert Gym [Directions] | 10:00 a.m. | ||
| Tue., 10/13 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | L 0-4 | ||
| Tue., 10/13 | JV Boys Soccer | Terryville | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Terryville | Away [Directions] | L 2-5 | 2:30 | |
| Tue., 10/13 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 1-3 | 2:45 | |
| Tue., 10/13 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 4:00 p.m. | 2:45 | |
| Wed., 10/14 | V Boys Cross Country | Housatonic Regional | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Wed., 10/14 | V Girls Cross Country | Housatonic Regional | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Thu., 10/15 | V Boys Soccer | Housatonic Regional | Away - Housatonic Field [Directions] | L 0-2 | 5:15 | |
| Thu., 10/15 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Field [Directions] | 4:30 p.m. | 3:15 | |
| Thu., 10/15 | V Girls Soccer | Housatonic Regional | Home - Walker Field [Directions] | L 0-4 | ||
| Fri., 10/16 | JV Football | Housatonic Regional | Away - HVRHS Field [Directions] | 7:00 p.m. | 5:00 | |
| Mon., 10/19 | V Girls Volleyball | St. Paul Catholic | Home - Gilbert Gym [Directions] | L 1-3 | ||
| Mon., 10/19 | JV Girls Volleyball | St. Paul Catholic | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | L 0-7 | 2:30 | |
| Tue., 10/20 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 10/20 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | L 3-0 | ||
| Wed., 10/21 | V Girls Volleyball | Watertown | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Wed., 10/21 | JV Girls Volleyball | Watertown | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | V Boys Cross Country | BL Championships | Away - Black Rock State Park | 3:30 p.m. | 2:30 | |
| Thu., 10/22 | V Girls Cross Country | BL Championships | Away - Black Rock State Park | 4:15 p.m. | 2:30 | |
| Fri., 10/23 | V Boys Cross Country | BL Championships Rain Date | Away - Black Rock State Park | 3:30 p.m. | ||
| Fri., 10/23 | V Football | Windsor Locks/Suffield/East Granby | Away - Suffield HS [Directions] | W 7-6 | 4:00 | |
| Fri., 10/23 | V Boys Soccer | Thomaston | Home - Walker Field [Directions] | W 2-0 | ||
| Fri., 10/23 | JV Boys Soccer | Thomaston | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 10/23 | V Girls Cross Country | BL Championships Rain Date | Away - Black Rock State Park | 4:15 p.m. | ||
| Fri., 10/23 | V Girls Soccer | Thomaston | Away - Highwood Farms Field [Directions] | W 2-0 | 2:30 | |
| Fri., 10/23 | V Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | L 1-3 | ||
| Fri., 10/23 | JV Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/24 | JV Football | Windsor Locks/Suffield/East Granby | Home - Gilbert [Directions] | 10:30 a.m. | ||
| Tue., 10/27 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | L 0-2 | 2:30 | |
| Tue., 10/27 | JV Boys Soccer | Wamogo | Away - Wamogo Regional HS [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 10/27 | V Girls Soccer | Wamogo | Home - Walker Field [Directions] | L 4-0 | ||
| Tue., 10/27 | JV Girls Soccer | Wamogo | Home - Rowley Field [Directions] | Cancelled | ||
| Tue., 10/27 | V Girls Volleyball | Terryville | Away - New Terryville HS [Directions] | L 0-3 | 2:45 | |
| Tue., 10/27 | JV Girls Volleyball | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | 2:45 | |
| Thu., 10/29 | V Boys Soccer | Nonnewaug | Home - Walker Field [Directions] | L 0-3 | ||
| Thu., 10/29 | JV Boys Soccer | Nonnewaug | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Thu., 10/29 | V Girls Soccer | Nonnewaug | Away [Directions] | L 1-8 | 2:30 | |
| Thu., 10/29 | V Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | W 3-1 | ||
| Thu., 10/29 | JV Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Sat., 10/31 | V Boys Cross Country | CIAC Class S Championships | Away - TBA | TBA | TBD | |
| Sat., 10/31 | V Football | Cromwell/Portland | Home - Gilbert [Directions] | L 9-13 | ||
| Sat., 10/31 | V Girls Cross Country | CIAC Class S Championships | Away - TBA | TBA | TBD | |
| Mon., 11/2 | JV Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | 3:30 p.m. | 2:00 | |
| Mon., 11/2 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | L 4-0 | ||
| Mon., 11/2 | V Girls Volleyball | Bolton | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Mon., 11/2 | JV Girls Volleyball | Bolton | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 11/3 | V Boys Soccer | Northwestern | Home - Walker Field [Directions] | L 1-6 | ||
| Tue., 11/3 | JV Boys Soccer | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Tue., 11/3 | V Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Tue., 11/3 | JV Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/6 | V Boys Cross Country | State Open Championships | Away - TBA | TBA | TBD | |
| Fri., 11/6 | V Girls Cross Country | CIAC State Open Championships | Away - TBA | TBA | TBA | |
| Fri., 11/13 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | L 6-34 | 4:00 | |
| Sat., 11/14 | JV Football | Northwest United | Home - Gilbert [Directions] | 9:00 a.m. | ||
| Thu., 11/19 | V Football | SMSA Coop | Away - Dillon Stadium [Directions] | W 28-6 | 2:45 | |
| Sat., 11/21 | JV Football | SMSA Coop | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Thu., 11/26 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Gilbert [Directions] | L 21-49 | ||
| Mon., 12/7 | V Girls Basketball | Forman School (Scrim.) | Home - Gilbert Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/8 | V Girls Basketball | Kaynor Tech (Scrim.) | Away - Kaynor Tech Gymnasium [Directions] | 4:45 p.m. | 3:30 | |
| Thu., 12/10 | V Boys Basketball | O'Brien Tech (Scrim.) | Home - Gilbert Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/10 | V Girls Basketball | Wolcott Tech (Scrim.) | Home - Gilbert Gym [Directions] | 3:00 p.m. | ||
| Tue., 12/15 | V Boys Basketball | Oxford (Scrim.) | Away - OHS-Main Gym [Directions] | 5:00 p.m. | 4:15 | |
| Tue., 12/15 | V Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | L 56-25 | ||
| Tue., 12/15 | JV Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | Cancelled | ||
| Wed., 12/16 | V Wrestling | Platt | Away - Platt high school [Directions] | 6:00 p.m. | 4:00 p.m. | 5:00 weigh in |
| Wed., 12/16 | V Wrestling | Housatonic Regional | Home - Gilbert Gym [Directions] | Cancelled | 5:30 weigh in | |
| Fri., 12/18 | V Boys Swimming and Diving | BL Relays | Away - Shepaug | 4:00 p.m. | 2:15 | |
| Fri., 12/18 | V Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | L 42-46 | 5:15 | |
| Sat., 12/19 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | L 27-64 | 1:00 | |
| Sat., 12/19 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 3:30 p.m. | 1:00 | |
| Sat., 12/19 | V Wrestling | Derby Invitational | Away - Derby HS | 10:00 a.m. | 7:00 | |
| Mon., 12/21 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 29-47 | 4:15 | |
| Mon., 12/21 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | 4:15 | |
| Mon., 12/21 | FR Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 3:45 p.m. | 2:30 | |
| Mon., 12/21 | V Boys Swimming and Diving | Simsbury | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Mon., 12/21 | V Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | L 54-46 | ||
| Mon., 12/21 | JV Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | Cancelled | ||
| Tue., 12/22 | V Wrestling | Holy Cross | Away - Holy Cross HS [Directions] | 6:30 p.m. | 4:30 | |
| Wed., 12/23 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | L 54-73 | 4:00 | |
| Wed., 12/23 | JV Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | 4:00 | |
| Wed., 12/23 | FR Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 3:45 p.m. | 2:30 | |
| Wed., 12/23 | V Girls Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | W 58-52 | ||
| Mon., 12/28 | V Wrestling | J. Law Duels | Away - J. Law HS | 9:00 a.m. | 6:30 | |
| Tue., 12/29 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Tue., 12/29 | V Boys Swimming and Diving | Gilbert | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Wed., 12/30 | V Wrestling | Terryville/Thomaston | Away - New Terryville HS [Directions] | 6:30 p.m. | 5:00 | |
| Wed., 12/30 | V Girls Basketball | East Granby | Home - Gilbert Gym [Directions] | W 44-41 | ||
| Wed., 12/30 | JV Girls Basketball | East Granby | Home - Gilbert Gym [Directions] | Cancelled | ||
| Sat., 1/2 | FR Girls Basketball | Wamogo | Away - Wamogo Gym 2 (Small Gym) [Directions] | 10:00 a.m. | ||
| Mon., 1/4 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Tue., 1/5 | V Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | L 39-50 | ||
| Tue., 1/5 | JV Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/5 | FR Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/5 | V Boys Swimming and Diving | Granby Memorial | Away - Farmington Valley YMCA [Directions] | 8:00 p.m. | 6:30 | |
| Tue., 1/5 | V Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | L 26-49 | 4:30 | |
| Tue., 1/5 | JV Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | Cancelled | 4:30 | |
| Wed., 1/6 | V Wrestling | Northwestern | Home - Gilbert Gym [Directions] | 6:30 p.m. | ||
| Thu., 1/7 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Fri., 1/8 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | L 35-64 | 4:15 | |
| Fri., 1/8 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | 4:15 | |
| Fri., 1/8 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 3:45 p.m. | 2:30 | |
| Fri., 1/8 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/8 | V Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | W 38-31 | ||
| Fri., 1/8 | JV Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | Cancelled | ||
| Sat., 1/9 | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/9 | V Boys Swimming and Diving | Granby Memorial | Home - Winsted YMCA [Directions] | 4:30 p.m. | 4:00 p.m. warmup | |
| Sat., 1/9 | V Wrestling | Canton, Weston, Montville | Away - Canton H.S. [Directions] | 10:00 a.m. | 8:30 | |
| Sat., 1/9 | FR Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | 12:00 p.m. | ||
| Tue., 1/12 | JV Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | Cancelled | ||
| Wed., 1/13 | V Boys Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 4:30 p.m. | ||
| Wed., 1/13 | V Wrestling | Seymour | Away - Seymour HS [Directions] | 2:30 p.m. | 12:30 | |
| Thu., 1/14 | JV Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/14 | JV Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/15 | V Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | L 51-82 | ||
| Fri., 1/15 | V Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | L 28-40 | ||
| Sat., 1/16 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/16 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Sat., 1/16 | V Wrestling | Wolcott Tech, Amity | Home - Gilbert Gym [Directions] | 10:00 a.m. | 9:00 a.m. Weigh-in | |
| Sat., 1/16 | V Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | L 50-36 | ||
| Tue., 1/19 | V Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | L 44-61 | ||
| Tue., 1/19 | JV Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/19 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Tue., 1/19 | V Girls Basketball | Terryville | Away - New Terryville HS [Directions] | W 43-26 | 4:30 | |
| Tue., 1/19 | JV Girls Basketball | Terryville | Away - New Terryville HS [Directions] | Cancelled | 4:30 | |
| Wed., 1/20 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L 53-64 | 4:00 | |
| Wed., 1/20 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | 4:00 | |
| Wed., 1/20 | V Wrestling | Nonnewaug | Home - Gilbert Gym [Directions] | 6:30 p.m. | ||
| Wed., 1/20 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | L 25-63 | 4:30 | |
| Wed., 1/20 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | Cancelled | 4:30 | |
| Fri., 1/22 | V Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | L 55-72 | ||
| Fri., 1/22 | JV Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/22 | FR Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/22 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | 2:30 | |
| Fri., 1/22 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 8:00 p.m. | ||
| Fri., 1/22 | V Wrestling | Wrangle on the Plains Invitational | Away - Shenendehowa HS | TBA | 2-day tourny - Clifton Park NY | |
| Mon., 1/25 | V Girls Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | W 51-27 | 2:40 | |
| Mon., 1/25 | JV Girls Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | Cancelled | 2:40 | |
| Tue., 1/26 | V Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | L 55-62 | 4:30 | |
| Tue., 1/26 | JV Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | 4:30 | |
| Tue., 1/26 | FR Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 1/26 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby HS Gymnasium [Directions] | 6:00 p.m. | 4:00 p.m. | |
| Tue., 1/26 | V Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | W 37-34 | ||
| Tue., 1/26 | JV Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | Cancelled | ||
| Wed., 1/27 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | Northwestern 97-74 | ||
| Fri., 1/29 | V Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | L 33-68 | ||
| Fri., 1/29 | JV Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/29 | FR Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/29 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/29 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 32-41 | 4:15 | |
| Fri., 1/29 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | Cancelled | 4:15 | |
| Sat., 1/30 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | Northwestern 88-72 | ||
| Sat., 1/30 | V Boys Swimming and Diving | Lewis Mills | Away - Giamatti Center - Bristol [Directions] | 6:15 p.m. | 4:45 | |
| Sat., 1/30 | V Wrestling | Portland Invitational | Away - Portland HS | 9:00 a.m. | 6:30 | |
| Tue., 2/2 | V Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | W 64-56 | ||
| Tue., 2/2 | JV Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/2 | FR Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/2 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | W 49-43 | 5:30 | |
| Tue., 2/2 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | Cancelled | 4:00 | |
| Wed., 2/3 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:30 p.m. | 5:45 | |
| Wed., 2/3 | V Wrestling | St. Paul Catholic | Home - Gilbert Gym [Directions] | 6:30 p.m. | ||
| Thu., 2/4 | V Boys Basketball | Canton | Away - Canton H.S. [Directions] | L 39-75 | 4:30 | |
| Thu., 2/4 | JV Boys Basketball | Canton | Away - Canton H.S. [Directions] | 5:30 p.m. | 4:30 | |
| Thu., 2/4 | FR Boys Basketball | Canton | Away - Canton H.S. [Directions] | 3:45 p.m. | 2:30 | |
| Fri., 2/5 | JV Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | Cancelled | ||
| Sat., 2/6 | V Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | L 66-72 | 4:15 | |
| Sat., 2/6 | JV Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 12:30 p.m. | 4:15 | |
| Sat., 2/6 | V Wrestling | Woodstock Invitational | Away - Woodstock Academy | 10:00 a.m. | 6:00 | |
| Sat., 2/6 | V Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | L 53-31 | ||
| Tue., 2/9 | V Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | L 48-55 | ||
| Tue., 2/9 | JV Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/9 | FR Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/9 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | L 44-61 | 4:30 | |
| Tue., 2/9 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | Cancelled | 4:30 | |
| Wed., 2/10 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | 5:45 | |
| Wed., 2/10 | V Wrestling | Oxford | Away [Directions] | 6:00 p.m. | 3:45 | |
| Thu., 2/11 | JV Boys Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/11 | JV Girls Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/12 | V Boys Basketball | Northwestern | Away - NWR-7 Gym [Directions] | L 55-63 | ||
| Fri., 2/12 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | Northwestern 86-Torington 82 | ||
| Fri., 2/12 | V Girls Basketball | Northwestern | Away - NWR-7 Gym [Directions] | W 41-40 | ||
| Sat., 2/13 | V Boys Swimming and Diving | Northwestern | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/13 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/13 | V Wrestling | Berkshire Valley Postseason Tournament | Away - TBD | 10:00 a.m. | 7:00 | |
| Sat., 2/13 | FR Girls Basketball | East Granby | Away - East Granby HS [Directions] | 12:00 p.m. | ||
| Tue., 2/16 | V Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | L 48-74 | ||
| Tue., 2/16 | JV Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/16 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L 35-58 | 4:00 | |
| Tue., 2/16 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | Cancelled | 4:00 | |
| Wed., 2/17 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 5:00 p.m. | ||
| Wed., 2/17 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 5:30 p.m. | 4:00 | |
| Thu., 2/18 | V Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | W 55-33 | ||
| Thu., 2/18 | JV Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | Cancelled | ||
| Fri., 2/19 | V Boys Basketball | Terryville | Away - New Terryville HS [Directions] | L 47-60 | 4:30 | |
| Fri., 2/19 | JV Boys Basketball | Terryville | Away - New Terryville HS [Directions] | 5:30 p.m. | 4:30 | |
| Fri., 2/19 | V Boys Swimming and Diving | Litchfield, Suffield | Home - Winsted YMCA [Directions] | 6:00 p.m. | ||
| Fri., 2/19 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | Northwestern 89 Holy Cross 96 | ||
| Fri., 2/19 | V Wrestling | Tournament Game - Opponent Not Known | Away | TBA | ||
| Sat., 2/20 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 10:30 a.m. | 9:30 | |
| Sat., 2/20 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/20 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Sat., 2/20 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away - Plainville HS | Cancelled | ||
| Sat., 2/20 | V Wrestling | Tournament Game - Opponent Not Known | Away | TBA | ||
| Sat., 2/20 | V Girls Basketball | Lewis Mills | Away - Lewis Mills HS [Directions] | 4:00 p.m. | 3:00 p.m. | 1st Rd BL Tournament |
| Wed., 2/24 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | L 41-55 | 4:30 | |
| Wed., 2/24 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | 4:30 | |
| Wed., 2/24 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 5:00 p.m. | ||
| Fri., 2/26 | V Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | L 43-77 | ||
| Fri., 2/26 | JV Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/26 | FR Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/26 | V Wrestling | Tournament Game - Opponent Not Known | Away | TBA | ||
| Sat., 2/27 | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/27 | V Boys Swimming and Diving | SPLASH | Away - Plainville HS | TBA | ||
| Sat., 2/27 | V Boys Swimming and Diving | Splash | Away - Plainville | TBA | ||
| Sat., 2/27 | V Wrestling | Tournament Game - Opponent Not Known | Away | TBA | ||
| Sat., 3/5 | V Boys Swimming and Diving | BL Championships | Away - Hotchkiss | TBA | ||
| Sat., 3/5 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away - Hotchkiss School | TBA | ||
| Wed., 3/9 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away | TBA | ||
| Thu., 3/10 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away | TBA | ||
| Sat., 3/12 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away | TBA | ||
| Tue., 3/15 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away | TBA | ||
| Thu., 3/24 | V Softball | Wolcott Tech (Scrim.) | Home - Rowley Field [Directions] | 3:30 p.m. | ||
| Sat., 3/26 | V Baseball | Wolcott (Scrim.) | Away - Wolcott HS [Directions] | 12:00 p.m. | 10:30 a.m. | |
| Tue., 3/29 | V Baseball | Monument Mountain (MA) (Scrim.) | Away | TBA | ||
| Tue., 3/29 | V Softball | Wilby (Scrim.) | Home - Rowley Field [Directions] | 3:30 p.m. | ||
| Sat., 4/2 | V Baseball | Northwestern | Home - Walker Field [Directions] | L 2-7 | ||
| Sat., 4/2 | JV Baseball | Northwestern | Away - Walker Field [Directions] | 2:30 p.m. | 2:45 | Drop Off Only |
| Wed., 4/6 | V Boys Tennis | Thomaston | Away - Nystroms Park [Directions] | W 4-1 | 2:30 | |
| Wed., 4/6 | V Girls Tennis | Thomaston | Home - Gilbert [Directions] | W 5-2 | ||
| Thu., 4/7 | V Boys Outdoor Track | Housatonic Regional | Away - Housatonic Track [Directions] | Cancelled | 2:30 | |
| Thu., 4/7 | V Girls Outdoor Track | Housatonic Regional | Away - Housatonic Track [Directions] | Cancelled | 2:30 | |
| Fri., 4/8 | V Baseball | Wolcott Tech | Home - Walker Field [Directions] | W 13-0 | 2:30 | |
| Fri., 4/8 | V Boys Tennis | Housatonic Regional | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Fri., 4/8 | V Girls Tennis | Housatonic Regional | Away - HS Courts [Directions] | L 0-7 | 2:30 | |
| Sat., 4/9 | JV Softball | Northwestern | Away - NW [Directions] | 10:00 a.m. | No bus | |
| Sat., 4/9 | JV Softball | TBD | Away - NW | 11:30 a.m. | No Bus | |
| Mon., 4/11 | V Baseball | Terryville | Away - New Terryville HS [Directions] | L 7-8 | 2:30 | |
| Mon., 4/11 | JV Baseball | Terryville | Away - New Terryville HS [Directions] | Cancelled | 2:30 | |
| Mon., 4/11 | V Boys Outdoor Track | Litchfield, Wamogo | Away - Plumb Hill Complex [Directions] | Cancelled | 2:30 | |
| Mon., 4/11 | V Girls Outdoor Track | Litchfield, Wamogo | Away - Plumb Hill Complex [Directions] | Cancelled | 2:30 | |
| Mon., 4/11 | V Softball | Terryville | Home - Rowley Field [Directions] | L 4-7 | ||
| Mon., 4/11 | V Girls Tennis | Litchfield | Home - Gilbert [Directions] | L 0-7 | ||
| Tue., 4/12 | V Boys Golf | Wolcott Tech | Away - Torrington CC [Directions] | OWTS 186 Terryville 216 Gilbert 242 | ||
| Wed., 4/13 | V Baseball | Housatonic Regional | Home - Walker Field [Directions] | W 3-2(9) | ||
| Wed., 4/13 | JV Baseball | Housatonic Regional | Home - Gilbert [Directions] | Cancelled | ||
| Wed., 4/13 | V Boys Golf | Wolcott Tech | Home - Greenwood Country Club [Directions] | OWTS 205 Gilbert 230 | ||
| Wed., 4/13 | V Boys Tennis | Nonnewaug | Away - Edgewood Tennis and Bath [Directions] | L 0-5 | 2:30 | |
| Wed., 4/13 | V Softball | Housatonic Regional | Away - HS Field [Directions] | W 23-4 | 2:30 | |
| Wed., 4/13 | V Girls Tennis | Nonnewaug | Home - Gilbert [Directions] | L 0-7 | ||
| Thu., 4/14 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | L 0-7 | 2:15 | |
| Fri., 4/15 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | W 15-5 | ||
| Fri., 4/15 | JV Baseball | Nonnewaug | Home - Gilbert [Directions] | Cancelled | ||
| Fri., 4/15 | V Boys Tennis | Wamogo | Home - Gilbert [Directions] | L 1-4 [Detailed Results] | ||
| Fri., 4/15 | V Softball | Nonnewaug | Away - Nonnewaug Varsity Softball Field [Directions] | L 1-21 | 2:30 | |
| Fri., 4/15 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | L 0-7 | 2:30 | |
| Mon., 4/18 | V Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | L 1-6 | 2:30 | |
| Mon., 4/18 | V Boys Golf | Housatonic Regional | Home - Greenwood Country Club [Directions] | Gilbert 233 Housatonic 232 | ||
| Mon., 4/18 | V Boys Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | L 1-4 | 3:00 | Drop Off Only (Activity Bus) |
| Mon., 4/18 | V Softball | Thomaston | Home - Rowley Field [Directions] | L 0-16 | ||
| Mon., 4/18 | V Girls Tennis | Northwestern | Home - Gilbert [Directions] | L 1-6 | ||
| Tue., 4/19 | V Boys Outdoor Track | Lewis Mills, Northwestern | Away - Lewis Mills Track [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 4/19 | V Girls Outdoor Track | Lewis Mills, Northwestern | Away - Lewis Mills Track [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 4/19 | V Softball | Northwestern | Away - Northwestern Varsity Field [Directions] | L 12-20 | 2:45 | Drop Off Only |
| Wed., 4/20 | V Baseball | Wamogo | Home - Walker Field [Directions] | W 3-0 | ||
| Wed., 4/20 | V Boys Golf | Northwestern | Home - Greenwood Country Club [Directions] | Gilbert 225 Northwest Regional #7 183 | ||
| Wed., 4/20 | V Boys Tennis | Shepaug Valley | Home - Gilbert [Directions] | L 2-3 [Detailed Results] | ||
| Wed., 4/20 | V Softball | Wamogo/Litchfield | Away - Wamogo Varsity Softball Field [Directions] | L 2-10 | 2:30 | |
| Thu., 4/21 | JV Baseball | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Lewis Mills | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Thu., 4/21 | V Girls Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | L 0-7 | 2:30 | |
| Fri., 4/22 | V Baseball | Litchfield | Away - Litchfield HS [Directions] | W 12-10 | 2:30 | Varsity only |
| Fri., 4/22 | V Softball | Litchfield | Home - Rowley Field [Directions] | W 13-6 | ||
| Sat., 4/23 | JV Baseball | Litchfield | Home - Walker Field [Directions] | 1:00 p.m. | 2:30 | |
| Mon., 4/25 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | L 0-1 | ||
| Mon., 4/25 | JV Baseball | Shepaug Valley | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Mon., 4/25 | V Boys Golf | Lewis Mills, Nonnewaug | Home - Greenwood Country Club [Directions] | Gilbert 197 Nonnewaug 203 Lewis Mills 169 | ||
| Mon., 4/25 | V Softball | Shepaug Valley | Away - Dick Ayer Field [Directions] | L 7-8 | 2:30 | |
| Tue., 4/26 | V Boys Golf | Nonnewaug, Northwestern | Away - Heritage Village CC [Directions] | Gilbert 209 Nonnewaug 189 Northwestern 197 | 2:00 | |
| Tue., 4/26 | V Boys Outdoor Track | Terryville | Home - Northwestern HS [Directions] | 4:00 p.m. | 2:30 | Drop Off Only |
| Tue., 4/26 | V Girls Outdoor Track | Terryville | Home - Northwestern [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | L 8-9 | 2:30 | |
| Wed., 4/27 | JV Baseball | Lewis Mills | Away - Lewis Mills JV Baseball Field [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 4/27 | V Boys Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | L 0-5 | 2:30 | |
| Wed., 4/27 | V Softball | Lewis Mills | Home - Rowley Field [Directions] | L 4-15 | ||
| Wed., 4/27 | V Girls Tennis | Lewis Mills | Home - Gilbert [Directions] | L 0-7 | ||
| Thu., 4/28 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | W 3-2 | 2:30 | |
| Thu., 4/28 | V Girls Tennis | Shepaug Valley | Home - Gilbert [Directions] | L 0-7 | ||
| Fri., 4/29 | V Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | L 0-11 | Yes | |
| Fri., 4/29 | JV Baseball | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Fri., 4/29 | V Softball | Northwestern | Home - Rowley Field [Directions] | L 0-19 | ||
| Fri., 4/29 | JV Softball | Northwestern | Home - Rowley Field [Directions] | Cancelled | ||
| Tue., 5/3 | V Boys Golf | Terryville, Northwestern | Away - Pequabuck Golf Course [Directions] | Gilbert 214 NW #7 191 Terryville 188 | 2:15 | |
| Tue., 5/3 | V Boys Outdoor Track | Litchfield, Shepaug Valley | Away - Plumb Hill Complex [Directions] | 4:15 p.m. | 2:30 | |
| Tue., 5/3 | V Girls Outdoor Track | Litchfield, Shepaug Valley | Away - Plumb Hill Complex [Directions] | 4:15 p.m. | 2:30 | |
| Thu., 5/5 | V Boys Tennis | Litchfield | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Thu., 5/5 | V Softball | Windsor Locks | Away - Windsor Locks HS [Directions] | L 3-14 | 2:30 | |
| Thu., 5/5 | V Girls Tennis | Litchfield | Away - Litchfield HS [Directions] | L 0-7 | 2:30 | |
| Fri., 5/6 | JV Softball | Terryville | Away - New Terryville HS [Directions] | Cancelled | 2:30 | |
| Sat., 5/7 | JV Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | 1:00 p.m. | 2:30 | |
| Mon., 5/9 | V Baseball | Housatonic Regional | Away - HS Field [Directions] | L 1-2 | 2:30 | |
| Mon., 5/9 | JV Baseball | Housatonic Regional | Away - HS JV Field [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 5/9 | V Boys Golf | Terryville, Litchfield | Home - Greenwood Country Club [Directions] | Gilbert 206 Litchfield 169 Terryville 216 | ||
| Mon., 5/9 | V Boys Tennis | Nonnewaug | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Mon., 5/9 | V Softball | Housatonic Regional | Home - Rowley Field [Directions] | W 23-13 | ||
| Mon., 5/9 | V Girls Tennis | Nonnewaug | Away - Edgewood Tennis and Bath [Directions] | L 0-7 | 2:30 | |
| Tue., 5/10 | V Baseball | Canton | Home - Walker Field [Directions] | W 2-1 | ||
| Tue., 5/10 | JV Baseball | Canton | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Boys Golf | Shepaug Valley, Wamogo | Away - Lake Waramaug Country Club [Directions] | Gilbert 224 Shepaug 227 Wamogo 233 | 2:00 | |
| Tue., 5/10 | V Boys Outdoor Track | Housatonic Regional, Nonnewaug | Away - Housatonic Track [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 5/10 | V Boys Tennis | Thomaston | Home - Gilbert [Directions] | L 2-3 [Detailed Results] | ||
| Tue., 5/10 | V Girls Outdoor Track | Housatonic Regional, Nonnewaug | Away - Housatonic Track [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 5/10 | V Softball | Canton | Home - Rowley Field [Directions] | L 5-14 | ||
| Wed., 5/11 | V Baseball | Nonnewaug | Away - Nonnewaug HS Field [Directions] | L 6-7 | 2:30 | |
| Wed., 5/11 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | Cancelled | 2:30 | |
| Wed., 5/11 | V Boys Golf | Litchfield, Wamogo | Away - Litchfield CC [Directions] | Gilbert 215 Wamogo 228 Litchfield 169 | 2:15 | |
| Wed., 5/11 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | L 2-3 | 2:30 | |
| Wed., 5/11 | V Softball | Nonnewaug | Home - Rowley Field [Directions] | L 5-22 | ||
| Wed., 5/11 | JV Softball | Nonnewaug | Home - Rowley Field [Directions] | Cancelled | ||
| Wed., 5/11 | V Girls Tennis | Wamogo | Home - Gilbert [Directions] | L 2-5 | ||
| Thu., 5/12 | V Boys Tennis | Northwestern | Home - Gilbert [Directions] | L 1-4 [Detailed Results] | ||
| Thu., 5/12 | V Girls Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | L 2-5 | 2:45 | Drop Off Only |
| Sat., 5/14 | V Baseball | Wamogo | Away - Fordham University [Directions] | W 3-1 | 2:30 | |
| Sat., 5/14 | V Boys Outdoor Track | Torrington Invitational | Away - THS | 9:30 a.m. | 8:30 a.m. | |
| Sat., 5/14 | V Girls Outdoor Track | Torrington Invitational | Away - THS | 9:30 a.m. | 8:30 a.m. | |
| Mon., 5/16 | JV Baseball | Wamogo | Home - Walker Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Boys Outdoor Track | Wamogo, Thomaston | Away - Plumb Hill Field Complex [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 5/16 | V Girls Outdoor Track | Wamogo, Thomaston | Away - Plumb Hill Field Complex [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 5/16 | V Softball | Wamogo/Litchfield | Home - Rowley Field [Directions] | L 2-17 | ||
| Tue., 5/17 | V Boys Tennis | Litchfield | Away - Litchfield HS [Directions] | L 1-4 | 2:30 | |
| Wed., 5/18 | V Baseball | Litchfield | Home - Walker Field [Directions] | W 5-2 | Varsity only | |
| Wed., 5/18 | V Softball | Litchfield | Away - Plumb Hill Complex [Directions] | L 8-9 | 2:30 | |
| Thu., 5/19 | V Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | W 5-1 | 2:30 | |
| Thu., 5/19 | JV Baseball | Shepaug Valley | Away - Shepaug Valley HS JV Baseball Field [Directions] | 4:00 p.m. | 2:30 | |
| Thu., 5/19 | V Girls Tennis | Berkshire League Championships | Away - Hotchkiss School | 9:00 a.m. | ||
| Fri., 5/20 | V Boys Tennis | Berkshire League Championships | Away - Hotchkiss | 9:00 a.m. | 7:15 a.m. | |
| Fri., 5/20 | V Softball | Shepaug Valley | Home - Rowley Field [Directions] | L 5-16 | ||
| Sat., 5/21 | V Boys Outdoor Track | Berkshire League Championships | Away | 9:00 a.m. | 7:45 a.m. | |
| Sat., 5/21 | V Girls Outdoor Track | Berkshire League Championships | Away | 9:00 a.m. | 7:45 a.m. | |
| Sat., 5/21 | JV Softball | Nonnewaug | Away - NW [Directions] | 10:00 a.m. | No bus | |
| Sat., 5/21 | JV Softball | TBD | Away - NW | 11:30 a.m. | ||
| Sun., 5/22 | V Boys Outdoor Track | BL Championships Rain Date | Away | 9:00 a.m. | Yes | |
| Sun., 5/22 | V Girls Outdoor Track | BL Championships Rain Date | Away | 9:00 a.m. | Yes | |
| Mon., 5/23 | V Baseball | Lewis Mills | Home - Walker Field [Directions] | W 6-5(9) | ||
| Mon., 5/23 | JV Baseball | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Mon., 5/23 | V Boys Golf | Housatonic Regional, Shepaug Valley | Away - Sharon Country Club [Directions] | Gilbert 205 Shepaug 228 Housatonic 255 | 2:00 | |
| Mon., 5/23 | V Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | L 9-17 | 2:30 | |
| Mon., 5/23 | JV Softball | Lewis Mills | Away - Lewis Mills JV Softball Field [Directions] | Cancelled | Yes | |
| Mon., 5/23 | V Girls Tennis | Thomaston | Away - Nystroms Park [Directions] | W 4-3 | 2:30 | |
| Tue., 5/24 | V Boys Outdoor Track | BL Festival | Away - HVRHS | 4:00 p.m. | ||
| Tue., 5/24 | V Boys Tennis | Housatonic Regional | Away - HS Courts [Directions] | L 0-4 | 2:30 | |
| Tue., 5/24 | V Girls Outdoor Track | BL Festival | Away - HVRHS | 4:00 p.m. | ||
| Tue., 5/24 | V Softball | Terryville | Away - New Terryville HS [Directions] | W 18-11 | 2:30 | |
| Tue., 5/24 | V Girls Tennis | Housatonic Regional | Home - Gilbert [Directions] | L 0-7 | ||
| Wed., 5/25 | V Baseball | Terryville | Home - Walker Field [Directions] | L 6-3 | ||
| Wed., 5/25 | V Baseball | Thomaston | Home - Walker Field [Directions] | W 7-6 | ||
| Wed., 5/25 | V Boys Golf | Lewis Mills | Away - Fairview Farms Golf Course - Harwinton [Directions] | Gilbert 205 Lewis Mills 163 | 2:15 | |
| Wed., 5/25 | V Boys Outdoor Track | BL Festival | Away - HVRHS | 4:00 p.m. | ||
| Wed., 5/25 | V Girls Outdoor Track | BL Festival | Away - HVRHS | 4:00 p.m. | ||
| Wed., 5/25 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | L 0-12 | 2:30 | |
| Thu., 5/26 | V Boys Golf | Chappa | Away | TBA | ||
| Tue., 5/31 | V Boys Golf | BL Championships | Away - Fairview Farm CC | TBA | ||
| Thu., 6/2 | V Boys Outdoor Track | Class S Championships | Away - Willow Brook Park, NB | 3:00 p.m. | TBA | |
| Thu., 6/2 | V Girls Outdoor Track | Class S Championships | Away - Willow Brook Park, NB | 3:00 p.m. | TBD | |
| Mon., 6/6 | V Boys Outdoor Track | CIAC Open Championships | Away - Willow Brook Park, NB | TBA | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC Open Championships | Away - Willow Brook Park, NB | TBA | ||