| Gilbert 2016-17 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 459 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Baseball | Avon (Scrim.) | Home - Walker Field [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Shepaug Valley | Home - Gilbert [Directions] | Cancelled | Cancelled | |
| TBA | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | Cancelled | Cancelled | |
| TBA | JV Baseball | Nonnewaug | Home - Gilbert [Directions] | Cancelled | Cancelled | |
| TBA | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 11:00 a.m. | ||
| TBA | FR Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | TBA | ||
| TBA | FR Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | TBA | ||
| TBA | FR Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | TBA | ||
| Wed., 8/24 | V Football | Simsbury (Scrim.) | Away - Simsbury HS [Directions] | 4:00 p.m. | ||
| Tue., 8/30 | V Football | Granby/Canton (Scrim.) | Away [Directions] | 4:30 p.m. | ||
| Tue., 8/30 | V Girls Volleyball | Torrington Christian Academy (Scrim.) | Home - Gilbert Gym [Directions] | 3:30 p.m. | ||
| Wed., 8/31 | V Girls Volleyball | Torrington Christian Academy (Scrim.) | Away | 3:30 p.m. | ||
| Fri., 9/2 | V Boys Soccer | Wolcott Tech (Scrim.) | Home - Walker Field [Directions] | 3:30 p.m. | ||
| Fri., 9/2 | V Girls Volleyball | Torrington (Scrim.) | Home - Gilbert Gym [Directions] | 3:30 p.m. | ||
| Sat., 9/3 | V Football | Bullard/Kolbe (Scrim.) | Away - Bullard Havens [Directions] | 12:00 p.m. | ||
| Tue., 9/6 | V Boys Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Tue., 9/6 | V Girls Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Tue., 9/6 | V Girls Soccer | Torrington (Scrim.) | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Fri., 9/9 | V Boys Soccer | Housatonic Regional | Away - HS Field [Directions] | 3:45 p.m. | L 2-8 | |
| Fri., 9/9 | JV Boys Soccer | Housatonic Regional | Away - HS Field [Directions] | 3:45 p.m. | ||
| Fri., 9/9 | V Girls Soccer | Housatonic Regional | Home - Walker Field [Directions] | 7:30 p.m. | L 0-6 | |
| Fri., 9/9 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Fri., 9/9 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/10 | V Football | Lewis Mills | Away - Muzzy Field - Bristol [Directions] | 1:00 p.m. | W 41-12 | |
| Mon., 9/12 | JV Football | Lewis Mills | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Boys Cross Country | Terryville, Wamogo, Nonnewaug | Away - New Terryville HS [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 9/13 | JV Boys Soccer | Wamogo | Away - Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/13 | V Girls Cross Country | Terryville, Wamogo, Nonnewaug | Away - New Terryville HS [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Soccer | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 9/13 | V Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 9/13 | JV Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Wed., 9/14 | JV Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Football | Canton | Home - Gilbert [Directions] | 7:00 p.m. | W 51-6 | |
| Fri., 9/16 | V Boys Soccer | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 9/16 | JV Boys Soccer | Litchfield | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 9/16 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | L 0-3 | |
| Sat., 9/17 | V Boys Cross Country | Stratton Brook Invitational | Away | TBA | ||
| Sat., 9/17 | JV Football | Canton | Away [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Stratton Brook Invitational | Away | TBA | ||
| Tue., 9/20 | V Boys Cross Country | Shepaug Valley, Litchfield | Away - Shepaug Valley HS [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 9/20 | JV Boys Soccer | Thomaston | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Shepaug Valley, Litchfield | Away - Shepaug Valley HS [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Thomaston | Away - Highwood Farms Field [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 9/21 | V Girls Volleyball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Wed., 9/21 | JV Girls Volleyball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 9/23 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 9/23 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/23 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | 7:00 p.m. | T 3-3 | |
| Fri., 9/23 | V Girls Volleyball | Cheney Tech | Home - Gilbert Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/23 | JV Girls Volleyball | Cheney Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | V Boys Cross Country | Winding Trails Invitational | Away | TBA | ||
| Sat., 9/24 | V Football | Nonnewaug | Away - Nonnewaug HS Football Field [Directions] | 1:00 p.m. | W 42-7 | |
| Sat., 9/24 | V Girls Cross Country | Winding Trails Invitational | Away | TBA | ||
| Sat., 9/24 | V Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | 11:15 a.m. | W 3-0 | |
| Sat., 9/24 | JV Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | 10:00 a.m. | ||
| Mon., 9/26 | JV Football | Nonnewaug | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Cross Country | Northwestern | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Soccer | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 9/27 | JV Boys Soccer | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | ||
| Tue., 9/27 | V Girls Cross Country | Northwestern | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 9/27 | JV Girls Soccer | Terryville | Home - Rowley Field [Directions] | Cancelled | Cancelled | |
| Tue., 9/27 | V Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 9/27 | JV Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Girls Soccer | Nonnewaug | Away - NHS - Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 9/30 | V Boys Soccer | Nonnewaug | Home - Walker Field [Directions] | 7:30 p.m. | L 0-7 | |
| Fri., 9/30 | JV Boys Soccer | Nonnewaug | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 9/30 | V Girls Volleyball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/30 | JV Girls Volleyball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | Windsor Locks/Suffield/East Granby | Home - Gilbert [Directions] | 2:30 p.m. | W 43-6 | |
| Mon., 10/3 | JV Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks HS [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Girls Volleyball | Terryville | Away - New Terryville HS [Directions] | 5:15 p.m. | L 3-2 | |
| Mon., 10/3 | JV Girls Volleyball | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Cross Country | Nonnewaug, Thomaston, Lewis Mills | Away - Nonnewaug HS [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | 3:45 p.m. | L 2-7 | |
| Tue., 10/4 | JV Boys Soccer | Lewis Mills | Away - Lewis Mills JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/4 | V Girls Cross Country | Nonnewaug, Thomaston, Lewis Mills | Away - Nonnewaug HS [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Lewis Mills | Home - Walker Field [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 10/4 | V Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/4 | JV Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/6 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Boys Soccer | Northwestern | Away - NWR Varsity Field [Directions] | 3:45 p.m. | L 1-5 | |
| Fri., 10/7 | JV Boys Soccer | Northwestern | Away - Northwestern JV field [Directions] | 3:45 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | 7:30 p.m. | L 0-5 | |
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational | Away - Wickham State Park East Hartford | TBA | ||
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational | Away - Wickham State Park East Hartford | TBA | ||
| Tue., 10/11 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 2-6 | |
| Tue., 10/11 | JV Boys Soccer | Housatonic Regional | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Housatonic Regional | Away - HS Field [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 10/11 | V Girls Volleyball | O'Brien Tech | Home - Gilbert Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Tue., 10/11 | JV Girls Volleyball | O'Brien Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Boys Cross Country | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Girls Cross Country | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 10/13 | JV Boys Soccer | Wamogo | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Thu., 10/13 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-1 | |
| Thu., 10/13 | V Girls Volleyball | Bolton | Away - Bolton HS [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/13 | JV Girls Volleyball | Bolton | Away - Bolton HS [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Football | Stafford/East Windsor/Somers | Away - Stafford High, Lighted field behind school [Directions] | 6:30 p.m. | L 7-40 | |
| Sat., 10/15 | JV Football | Stafford/East Windsor/Somers | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Tue., 10/18 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 10/18 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 3-5 | |
| Tue., 10/18 | V Girls Volleyball | Northwestern | Away - Northwestern HS [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/18 | JV Girls Volleyball | Northwestern | Away - Northwestern HS [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 10/19 | JV Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | V Boys Cross Country | BL Championships | Away - Black Rock State Park | 4:00 p.m. | ||
| Thu., 10/20 | V Girls Cross Country | BL Championships | Away - Black Rock State Park | 4:00 p.m. | ||
| Fri., 10/21 | V Boys Soccer | Thomaston | Away - Highwood Farms Field [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 10/21 | JV Boys Soccer | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Thomaston | Home - Walker Field [Directions] | 7:30 p.m. | L 1-2 | |
| Fri., 10/21 | V Girls Volleyball | Terryville | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Fri., 10/21 | JV Girls Volleyball | Terryville | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/22 | V Football | Coginchaug/Hale Ray/East Hampton | Away - CRHS Stadium Field & Track [Directions] | 1:00 p.m. | W 35-8 | |
| Mon., 10/24 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Jonathan Law | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Mon., 10/24 | JV Girls Volleyball | Jonathan Law | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 0-1 | |
| Tue., 10/25 | JV Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Wed., 10/26 | V Girls Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 10/28 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | 3:30 p.m. | L 1-8 | |
| Fri., 10/28 | JV Boys Soccer | Terryville | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 10/28 | V Girls Soccer | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | L 0-6 | |
| Fri., 10/28 | JV Girls Soccer | Terryville | Away - New Terryville HS [Directions] | Cancelled | Cancelled | |
| Fri., 10/28 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Fri., 10/28 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class S States | Away - Wickham Park East Hartford | TBA | ||
| Sat., 10/29 | V Football | SMSA Coop | Home - Gilbert [Directions] | 1:00 p.m. | W 38-14 | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class S States | Away - Wickham Park East Hartford | TBA | ||
| Mon., 10/31 | JV Football | SMSA Coop | Home - Gilbert [Directions] | 3:00 p.m. | ||
| Tue., 11/1 | V Boys Soccer | Northwestern | Home - Walker Field [Directions] | 7:30 p.m. | L 0-3 | |
| Tue., 11/1 | JV Boys Soccer | Northwestern | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 11/1 | V Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 11/1 | V Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 11/1 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC Open Championships | Away | TBA | ||
| Fri., 11/4 | V Girls Cross Country | CIAC Open Championships | Away | TBA | ||
| Sat., 11/5 | V Football | Haddam-Killingworth | Home - Gilbert [Directions] | 1:00 p.m. | W 33-0 | Homecoming |
| Mon., 11/7 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:15 p.m. | ||
| Sat., 11/12 | V Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 1:00 p.m. | L 7-35 | |
| Mon., 11/14 | JV Football | Old Saybrook | Home - Walker Field [Directions] | 4:30 p.m. | ||
| Thu., 11/24 | V Football | WCA | Home - Gilbert [Directions] | 10:00 a.m. | W 29-6 | |
| Tue., 12/6 | V Girls Basketball | Mt. Everett (MA) (Scrim.) | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 12/6 | JV Girls Basketball | Mt. Everett (MA) (Scrim.) | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/7 | V Girls Basketball | Torrington (Scrim.) | Home - Gilbert Gym [Directions] | 3:00 p.m. | ||
| Fri., 12/9 | V Girls Basketball | St. Paul Catholic (Scrim.) | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | ||
| Sat., 12/10 | V Boys Basketball | O'Brien Tech (Scrim.) | Home - Gilbert Gym [Directions] | 12:30 p.m. | ||
| Sat., 12/10 | V Girls Basketball | Avon (Scrim.) | Away - Avon HS [Directions] | 10:00 a.m. | ||
| Sat., 12/10 | JV Girls Basketball | Avon (Scrim.) | Away - Avon HS [Directions] | 10:00 a.m. | ||
| Tue., 12/13 | V Boys Basketball | Torrington (Scrim.) | Away - Torrington HS [Directions] | 5:00 p.m. | ||
| Tue., 12/13 | V Girls Basketball | Terryville | Away - New Terryville HS [Directions] | 7:00 p.m. | W 55-16 | |
| Tue., 12/13 | JV Girls Basketball | Terryville | Away - New Terryville HS [Directions] | 5:30 p.m. | ||
| Wed., 12/14 | V Wrestling | Thomaston | Home - Gilbert Gym [Directions] | 6:30 p.m. | 5:30 weigh in | |
| Thu., 12/15 | V Boys Basketball | Oxford (Scrim.) | Away - OHS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/15 | JV Boys Basketball | Oxford (Scrim.) | Away - OHS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 7:00 p.m. | W 51-38 | |
| Fri., 12/16 | JV Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Sat., 12/17 | V Boys Basketball | Ansonia (Scrim.) | Home [Directions] | 12:00 p.m. | ||
| Sat., 12/17 | V Wrestling | Derby Invitational | Away | 10:00 a.m. | ||
| Mon., 12/19 | V Girls Basketball | Wolcott | Home - Gilbert Gym [Directions] | 6:00 p.m. | L 46-35 | |
| Mon., 12/19 | JV Girls Basketball | Wolcott | Home - Gilbert Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/20 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | L 95-35 | |
| Tue., 12/20 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | FR Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/20 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 8:15 p.m. | 7:45 warm up | |
| Tue., 12/20 | V Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 33-30 | |
| Tue., 12/20 | JV Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/21 | V Wrestling | Terryville-Thomaston | Home - Gilbert Gym [Directions] | 6:30 p.m. | 5:30 Weigh in | |
| Thu., 12/22 | V Boys Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 4:30 p.m. | ||
| Fri., 12/23 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | L 30-88 | |
| Fri., 12/23 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Fri., 12/23 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 3:45 p.m. | ||
| Fri., 12/23 | V Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | W 51-30 | |
| Fri., 12/23 | JV Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/27 | V Boys Swimming and Diving | Simsbury | Away - Westminster School [Directions] | 7:30 p.m. | 7:00 warm up | |
| Tue., 12/27 | V Wrestling | J.Law Duals | Away | 9:00 a.m. | ||
| Wed., 12/28 | V Boys Basketball | Terryville | Away - New Terryville HS [Directions] | 7:00 p.m. | L 30-63 | |
| Wed., 12/28 | JV Boys Basketball | Terryville | Away - New Terryville HS [Directions] | 5:30 p.m. | ||
| Wed., 12/28 | V Wrestling | Northwestern | Away - Northwestern Gym [Directions] | 6:30 p.m. | No Bus | |
| Fri., 12/30 | V Boys Swimming and Diving | Northwestern | Home - Winsted YMCA [Directions] | 7:30 p.m. | 7:00 warm up | |
| Fri., 12/30 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Tue., 1/3 | V Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 62-78 | |
| Tue., 1/3 | JV Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/3 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 8:15 p.m. | 7:45 warm up | |
| Tue., 1/3 | V Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 29-33 | |
| Tue., 1/3 | JV Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Swimming and Diving | Lewis Mills | Away - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Wed., 1/4 | V Wrestling | Notre Dame-West Haven | Home - Gilbert Gym [Directions] | 6:30 p.m. | 5:30 weigh in | |
| Wed., 1/4 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | W 45-42 | |
| Wed., 1/4 | JV Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 51-90 | |
| Fri., 1/6 | JV Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | 7:00 warm up | |
| Fri., 1/6 | V Girls Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 54-22 | |
| Fri., 1/6 | JV Girls Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/7 | V Wrestling | Super Quad | Away - Gloucester HS, MA | 9:00 a.m. | 5:30 bus | |
| Sat., 1/7 | FR Girls Basketball | Housatonic Regional | Away [Directions] | 12:30 p.m. | ||
| Mon., 1/9 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gymnasium [Directions] | 7:00 p.m. | L 54-70 | |
| Mon., 1/9 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 1/9 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Mon., 1/9 | V Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 6:00 p.m. | W 55-33 | |
| Mon., 1/9 | JV Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/11 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | L 40-70 | |
| Wed., 1/11 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 1/11 | V Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 66-38 | |
| Wed., 1/11 | JV Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | JV Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/12 | V Wrestling | Nonnewaug | Away - Nonnewaug HS Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 1/12 | JV Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/13 | V Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 42-78 | |
| Fri., 1/13 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | 4:00 warm up | |
| Fri., 1/13 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 5:30 p.m. | W 35-25 | |
| Sat., 1/14 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 4:30 p.m. | 4:00 warm up | |
| Sat., 1/14 | V Wrestling | Gilbert Duals | Home - Gilbert Gym [Directions] | 9:00 a.m. | 8:00 weigh in | |
| Mon., 1/16 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 1:45 p.m. | 1:15 warm up | |
| Wed., 1/18 | V Wrestling | Derby/Oxford/Holy Cross | Home - Gilbert Gym [Directions] | 5:00 p.m. | 5:30 weigh in | |
| Thu., 1/19 | V Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | 5:30 p.m. | W 59-44 | |
| Thu., 1/19 | JV Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 7:00 p.m. | W 40-37 | |
| Fri., 1/20 | JV Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 4:30 p.m. | 4:00 warm up | |
| Fri., 1/20 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/20 | V Wrestling | Avon, Farmington, Terryville-Thomaston | Away - Avon HS--Gym Two [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 50-38 | |
| Fri., 1/20 | JV Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/21 | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | FR Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | Cancelled | Cancelled | |
| Wed., 1/25 | V Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 48-89 | |
| Wed., 1/25 | JV Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/25 | FR Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/25 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Wed., 1/25 | V Wrestling | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | ||
| Wed., 1/25 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | L 48-27 | |
| Wed., 1/25 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 35-63 | |
| Fri., 1/27 | JV Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | 7:00 warm up | |
| Fri., 1/27 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | W 54-40 | |
| Fri., 1/27 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Sat., 1/28 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/28 | V Boys Swimming and Diving | Granby Memorial | Home - Winsted YMCA [Directions] | 7:00 p.m. | 6:30 warm up | |
| Sat., 1/28 | V Wrestling | Portland Invitational | Away | 9:00 a.m. | ||
| Sat., 1/28 | FR Girls Basketball | Housatonic Regional | Home [Directions] | 11:00 a.m. | ||
| Mon., 1/30 | V Boys Basketball | Canton | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 29-86 | |
| Mon., 1/30 | JV Boys Basketball | Canton | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/30 | FR Boys Basketball | Canton | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Wrestling | Oxford | Home - Gilbert Gym [Directions] | 6:30 p.m. | 5:30 weigh in | |
| Thu., 2/2 | V Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 39-38 | |
| Thu., 2/2 | JV Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 42-63 | |
| Fri., 2/3 | JV Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 57-34 | |
| Fri., 2/3 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/4 | V Boys Swimming and Diving | Lewis Mills | Away - Giamatti Center - Bristol [Directions] | 7:00 p.m. | 6:15 warm up | |
| Sat., 2/4 | V Wrestling | Woodstock Invitationals | Away | 10:00 a.m. | ||
| Wed., 2/8 | V Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 51-66 | |
| Wed., 2/8 | JV Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/8 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 5:00 p.m. | ||
| Wed., 2/8 | V Wrestling | TBD | Away | Cancelled | Cancelled | |
| Sat., 2/11 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:30 p.m. | L 23-66 | No Bus |
| Sat., 2/11 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 4:30 p.m. | No Bus | |
| Sat., 2/11 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/11 | V Wrestling | Berkshire Valley Postseason Tournament | Away - Derby HS | 10:00 a.m. | 8:00 weigh in | |
| Sat., 2/11 | V Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | 6:00 p.m. | W 49-41 | No Bus |
| Sat., 2/11 | JV Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | 3:00 p.m. | No Bus | |
| Sat., 2/11 | FR Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | Cancelled | Cancelled | |
| Sat., 2/11 | FR Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | Cancelled | Cancelled | |
| Mon., 2/13 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | L 50-45 | |
| Mon., 2/13 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 60-70 | |
| Tue., 2/14 | JV Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | FR Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 6:00 p.m. | W 48-28 | |
| Tue., 2/14 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/15 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/15 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 5:00 p.m. | 5:00 warm up | |
| Thu., 2/16 | V Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 49-47 | |
| Fri., 2/17 | V Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 57-66 | |
| Fri., 2/17 | JV Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/17 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 7:30 p.m. | 7:00 warm up | |
| Fri., 2/17 | V Wrestling | CIAC Class S Championships | Away - Windham HS | TBA | ||
| Sat., 2/18 | V Boys Basketball | Coventry | Away - Matthew J. Hurlock Gymnasium [Directions] | 4:00 p.m. | L 45-51 | |
| Sat., 2/18 | JV Boys Basketball | Coventry | Away - Matthew J. Hurlock Gymnasium [Directions] | 2:30 p.m. | ||
| Sat., 2/18 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 4:30 p.m. | 4:00 warm up | |
| Sat., 2/18 | V Boys Swimming and Diving | Gilbert | Home - Winsted YMCA [Directions] | 4:30 p.m. | Senior Night | |
| Sat., 2/18 | V Wrestling | CIAC Class S Championships | Away - Windham HS | TBA | ||
| Tue., 2/21 | V Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 52-32 | |
| Tue., 2/21 | JV Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/21 | FR Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/21 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Wed., 2/22 | V Boys Swimming and Diving | Torrington | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Thu., 2/23 | V Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 65-39 | |
| Thu., 2/23 | JV Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/23 | FR Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | ||
| Fri., 2/24 | V Boys Swimming and Diving | Granby Memorial | Away - FVYMCA [Directions] | 7:30 p.m. | 7:00 warm up | |
| Fri., 2/24 | V Wrestling | CIAC Open Championships | Away - Floyd Little Field House New Haven | TBA | ||
| Sat., 2/25 | V Boys Swimming and Diving | Splash | Away - Plainville HS | TBA | ||
| Sat., 2/25 | V Boys Swimming and Diving | SPLASH | Away - Plainville HS | TBA | ||
| Sat., 2/25 | V Wrestling | CIAC Open Championships | Away - Floyd Little Field House New Haven | TBA | ||
| Tue., 2/28 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | 7:45 warm up | |
| Fri., 3/3 | V Boys Swimming and Diving | BL Diving | Away - Shepaug | TBA | ||
| Fri., 3/3 | V Wrestling | New England Championships | Away | TBA | ||
| Sat., 3/4 | V Boys Swimming and Diving | BL Championships | Away - Plainville HS | 1:00 p.m. | ||
| Sat., 3/4 | V Boys Swimming and Diving | BL Championships | Away - Plainville HS | 1:00 p.m. | ||
| Sat., 3/4 | V Wrestling | New England Championships | Away | TBA | ||
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class S Diving Trials | Away - Plainville HS | TBA | ||
| Sat., 3/11 | V Boys Swimming and Diving | State Qualifing | Away - TBA | TBA | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class S Swim Trials | Away - Plainville HS | TBA | ||
| Wed., 3/15 | V Boys Swimming and Diving | CIAC Class S Swim Finals | Away - Wesleyan U. | TBA | ||
| Thu., 3/16 | V Boys Swimming and Diving | State Finals | Away | TBA | Finals Bus 11:00am | |
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Open Dive Finals | Away - Bulkeley HS | TBA | ||
| Sat., 3/18 | V Boys Swimming and Diving | State Opens | Away | TBA | ||
| Mon., 4/3 | V Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | 4:00 p.m. | W 6-2 | Tennis Courts |
| Mon., 4/3 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 4/3 | V Softball | Shepaug Valley | Home - Rowley Field [Directions] | 3:45 p.m. | L 1-15 | |
| Mon., 4/3 | V Girls Tennis | Shepaug Valley | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/5 | V Boys Outdoor Track | Shepaug Valley | Away - Shepaug Valley HS Track [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Boys Tennis | Thomaston | Home - Gilbert [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Wed., 4/5 | V Girls Outdoor Track | Shepaug Valley | Away - Shepaug Valley HS Track [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Girls Tennis | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | W 4-3 | |
| Fri., 4/7 | V Softball | Lewis Mills | Home - Rowley Field [Directions] | 3:45 p.m. | L 5-13 | |
| Mon., 4/10 | V Baseball | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | W 10-2 | |
| Mon., 4/10 | JV Baseball | Wamogo | Home - Walker Field [Directions] | Cancelled | Cancelled | |
| Mon., 4/10 | V Boys Tennis | Litchfield | Home - Gilbert [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 4/10 | V Girls Tennis | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/11 | V Boys Tennis | Nonnewaug | Home - Gilbert [Directions] | 10:00 a.m. | L 0-5 [Detailed Results] | |
| Tue., 4/11 | V Girls Tennis | Nonnewaug | Away - Edgewood Tennis Club [Directions] | 10:00 a.m. | L 0-7 | |
| Thu., 4/13 | V Baseball | Thomaston | Away - Thomaston HS Field [Directions] | 2:00 p.m. | L 1-11 | |
| Thu., 4/13 | JV Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | Cancelled | Cancelled | |
| Thu., 4/13 | JV Baseball | Thomaston | Away - THS [Directions] | Cancelled | Cancelled | |
| Thu., 4/13 | V Softball | Thomaston | Home - Rowley Field [Directions] | 3:45 p.m. | L 7-21 | |
| Mon., 4/17 | V Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 3-1 | Drop off only |
| Mon., 4/17 | V Boys Golf | Wolcott Tech | Away - Torrington Country Club [Directions] | 2:00 p.m. | Gilbert 175 OWTS 194 | |
| Mon., 4/17 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 4/17 | V Softball | Northwestern | Home - Rowley Field [Directions] | 3:45 p.m. | L 4-21 | |
| Mon., 4/17 | V Girls Tennis | Wamogo | Home - Gilbert [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/18 | V Boys Golf | Shepaug Valley, Lewis Mills | Home [Directions] | 3:00 p.m. | Gilbert 184 Lewis Mills 186 Shepaug 223 | |
| Tue., 4/18 | V Boys Outdoor Track | Litchfield, Lewis Mills | Home - Northwestern [Directions] | 4:00 p.m. | Drop off only | |
| Tue., 4/18 | V Girls Outdoor Track | Litchfield, Lewis Mills | Home - Northwestern [Directions] | 4:00 p.m. | Drop off only | |
| Wed., 4/19 | V Baseball | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | W 9-0 | |
| Wed., 4/19 | V Boys Golf | Wolcott Tech | Home - Greenwood Country Club [Directions] | 4:00 p.m. | Gilbert 171 OWTS 195 | |
| Wed., 4/19 | V Softball | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | L 17-18 | |
| Thu., 4/20 | V Boys Outdoor Track | Housatonic Regional, Wamogo | Home - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 4/20 | V Girls Outdoor Track | Housatonic Regional, Wamogo | Home - Plumb Hill [Directions] | 3:45 p.m. | ||
| Thu., 4/20 | V Girls Tennis | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/21 | JV Baseball | Terryville | Home - Gilbert [Directions] | Cancelled | Cancelled | |
| Mon., 4/24 | V Baseball | Nonnewaug | Away - Nonnewaug HS Field [Directions] | 4:00 p.m. | L 2-5 | Tennis Courts |
| Mon., 4/24 | V Boys Golf | Wamogo, Nonnewaug | Away - Stony Brook GC [Directions] | 3:00 p.m. | Gilbert 173 Wamogo 193 Nonnewaug 182 | |
| Mon., 4/24 | V Boys Tennis | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 4/24 | V Softball | Nonnewaug | Home - Rowley Field [Directions] | 3:45 p.m. | L 8-25 | |
| Mon., 4/24 | V Girls Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 4/27 | V Baseball | Terryville | Home - Walker Field [Directions] | 4:15 p.m. | L 0-1 | |
| Thu., 4/27 | V Boys Golf | Housatonic Regional, Northwestern | Away - Canaan [Directions] | 3:30 p.m. | Gilbert 163 Housatonic 206 NW #7 196 | |
| Thu., 4/27 | V Boys Outdoor Track | Northwestern | Away - Northwestern Varsity Field [Directions] | 4:00 p.m. | Drop off only | |
| Thu., 4/27 | V Boys Tennis | Shepaug Valley | Home - Gilbert [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Thu., 4/27 | V Girls Outdoor Track | Northwestern | Away - Northwestern Varsity Field [Directions] | 4:00 p.m. | Drop off only | |
| Thu., 4/27 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/28 | V Baseball | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | L 0-4 | |
| Fri., 4/28 | JV Baseball | Terryville | Away - Lower Fisher Field [Directions] | Cancelled | Cancelled | |
| Fri., 4/28 | V Boys Tennis | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | L 1-4 | |
| Fri., 4/28 | V Softball | Terryville | Home - Rowley Field [Directions] | 3:45 p.m. | L 14-16 | |
| Fri., 4/28 | V Girls Tennis | Thomaston | Home - Gilbert [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 5/1 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | 4:00 p.m. | L 0-5 | |
| Mon., 5/1 | V Boys Golf | Wamogo | Away - Stonybrook GC [Directions] | 3:30 p.m. | Gilbert 191 Wamogo 189 Obrien tech 196 | |
| Mon., 5/1 | V Boys Tennis | Housatonic Regional | Home - Gilbert [Directions] | 3:45 p.m. | L 2-3 [Detailed Results] | |
| Mon., 5/1 | V Softball | Shepaug Valley | Away - Dick Ayer Field [Directions] | 4:15 p.m. | L 5-20 | |
| Mon., 5/1 | V Girls Tennis | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/2 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | 4:00 p.m. | L 4-19 | |
| Tue., 5/2 | V Boys Golf | Wamogo | Home [Directions] | 3:00 p.m. | Gilbert 188 Wamogo 186 | |
| Tue., 5/2 | V Boys Outdoor Track | Terryville, Shepaug Valley | Away [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Terryville, Shepaug Valley | Away [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Softball | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | L 3-8 | |
| Wed., 5/3 | V Baseball | Canton | Away - Bowdoin Field [Directions] | 3:45 p.m. | W 13-2 | |
| Wed., 5/3 | JV Baseball | Canton | Away [Directions] | Cancelled | Cancelled | |
| Wed., 5/3 | V Boys Golf | Litchfield, Housatonic Regional | Away - Litchfield CC [Directions] | 3:00 p.m. | Gilbert 184 Housatonic 202 Litchfield 207 | |
| Wed., 5/3 | V Boys Tennis | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 5/3 | V Softball | Canton | Away - Canton H.S. [Directions] | 3:45 p.m. | W 23-10 | |
| Wed., 5/3 | V Girls Tennis | Litchfield | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/4 | V Baseball | Lewis Mills | Home - Walker Field [Directions] | 3:45 p.m. | L 4-8 | |
| Thu., 5/4 | V Softball | Terryville | Away - Lower Fisher Field [Directions] | 3:45 p.m. | W 16-9 | |
| Fri., 5/5 | JV Baseball | Lewis Mills | Home - Gilbert [Directions] | Cancelled | Cancelled | |
| Mon., 5/8 | V Baseball | Wamogo | Home - Wamogo Baseball Field [Directions] | 4:00 p.m. | W 10-2 | |
| Mon., 5/8 | JV Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | Cancelled | Cancelled | |
| Mon., 5/8 | V Boys Tennis | Wamogo | Home - Gilbert [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Mon., 5/8 | V Softball | Wamogo/Litchfield | Home - Rowley Field [Directions] | 3:30 p.m. | L 0-16 | |
| Mon., 5/8 | V Softball | Wamogo/Litchfield | Home - Rowley Field [Directions] | 5:00 p.m. | L 0-15 | |
| Mon., 5/8 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 5/9 | V Boys Golf | Shepaug Valley, Northwestern | Away - Lake Waramaug Country Club [Directions] | 3:00 p.m. | Gilbert 176 Sheapug 217 Nw #7 217 | |
| Tue., 5/9 | V Boys Outdoor Track | Litchfield, Nonnewaug | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | Litchfield, Nonnewaug | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Golf | Stiberg Tournament | Away - Farmingbury Hills GC | TBA | Bailey /Liu 74 | |
| Wed., 5/10 | V Boys Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Wed., 5/10 | V Boys Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | Drop off only |
| Wed., 5/10 | V Girls Tennis | Northwestern | Home - Gilbert HS [Directions] | 3:45 p.m. | L 0-7 | Drop off only |
| Wed., 5/10 | V Girls Tennis | Northwestern | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/11 | JV Baseball | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Housatonic Regional | Away - Housatonic [Directions] | 4:15 p.m. | L 0-5 | |
| Thu., 5/11 | V Girls Tennis | Housatonic Regional | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 5/12 | V Baseball | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 1-11 | |
| Fri., 5/12 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | 3:45 p.m. | L 0-12 | |
| Sat., 5/13 | V Boys Outdoor Track | Torrington Varsity Club Invt. | Away - Torrington HS | 10:30 a.m. | ||
| Sat., 5/13 | V Girls Outdoor Track | Torrington Varsity Club Invt. | Away - Torrington HS | 10:30 a.m. | ||
| Mon., 5/15 | V Baseball | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | L 0-4 | |
| Mon., 5/15 | V Boys Outdoor Track | Thomaston | Home - Northwestern [Directions] | 4:00 p.m. | Drop off only | |
| Mon., 5/15 | V Boys Tennis | Nonnewaug | Away - Edgewood Tennis Club [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 5/15 | V Girls Outdoor Track | Thomaston | Home - Northwestern [Directions] | 4:00 p.m. | Drop off only | |
| Mon., 5/15 | V Softball | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 4-19 | Drop off only |
| Mon., 5/15 | V Girls Tennis | Nonnewaug | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/16 | JV Baseball | Housatonic Regional | Home - Gilbert [Directions] | Cancelled | Cancelled | |
| Wed., 5/17 | V Baseball | Litchfield | Away - Litchfield HS Baseball Field [Directions] | 4:00 p.m. | W 8-2 | |
| Wed., 5/17 | V Boys Golf | Terryville, Litchfield | Home - Greenwood Country Club [Directions] | 3:00 p.m. | Gilbert 168 Litchfield 201 Terryville 206 | |
| Wed., 5/17 | V Softball | Litchfield | Home - Rowley Field [Directions] | 3:45 p.m. | L 11-17 | |
| Thu., 5/18 | V Baseball | Housatonic Regional | Home - Walker Field [Directions] | 3:30 p.m. | L 14-1 | |
| Thu., 5/18 | V Boys Golf | Northwestern | Away - Norfolk CC [Directions] | 3:00 p.m. | Gilbert 175 NW #7 206 | |
| Thu., 5/18 | V Softball | Housatonic Regional | Home - Rowley Field [Directions] | 3:30 p.m. | W 24-19 | |
| Thu., 5/18 | V Girls Tennis | BL Championships | Away - Hotchkiss School - Lakeville | TBA | ||
| Fri., 5/19 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 5/19 | V Boys Tennis | BL Championships | Away - Hotchkiss School - Lakeville | TBA | ||
| Fri., 5/19 | V Softball | Nonnewaug | Away - Nonnewaug HS Field [Directions] | 3:45 p.m. | L 13-20 | |
| Sat., 5/20 | V Boys Outdoor Track | BL Championships | Away - Plumb Hill Field Complex, Litchfield | TBA | ||
| Sat., 5/20 | V Girls Outdoor Track | BL Championships | Away - Plumb Hill Field Complex, Litchfield | TBA | Rain Date 5/21 | |
| Mon., 5/22 | V Baseball | Housatonic Regional | Away - Housatonic Field [Directions] | 4:00 p.m. | L 20-0 | |
| Mon., 5/22 | JV Baseball | Housatonic Regional | Away - HS JV Field [Directions] | Cancelled | Cancelled | |
| Mon., 5/22 | V Boys Golf | Housatonic Regional, Terryville | Away - Sharon CC [Directions] | 3:15 p.m. | Gilbert 171 Terryville 199 Housy 204 | |
| Tue., 5/23 | JV Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | Drop off only | |
| Tue., 5/23 | V Boys Golf | Housatonic Regional | Away - Sharon [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | V Boys Outdoor Track | BL Festival | Away - HVRHS | TBA | Day 1 | |
| Tue., 5/23 | V Girls Outdoor Track | BL Festival | Away - HVRHS | TBA | ||
| Tue., 5/23 | V Softball | Windsor Locks | Away - Veteran's Memorial Park [Directions] | 7:00 p.m. | L 6-11 | |
| Wed., 5/24 | V Boys Golf | Nonnewaug, Lewis Mills | Away - Heritage Country Club [Directions] | 3:00 p.m. | Gilbert 166 Lewis Mills 175 Nonnewaug 188 | |
| Wed., 5/24 | V Boys Outdoor Track | BL Festival | Away | TBA | Day 2 | |
| Wed., 5/24 | V Girls Outdoor Track | BL Festival | Away - HVRHS | TBA | ||
| Wed., 5/24 | V Softball | Lewis Mills | Away - Shepaug - Ted Alex softball field [Directions] | 5:00 p.m. | L 13-18 | |
| Thu., 5/25 | V Baseball | Bulkeley | Away - Dunkin Donuts Park [Directions] | Cancelled | Cancelled | |
| Thu., 5/25 | V Boys Golf | Chappa Tournament | Away | TBA | ||
| Sat., 5/27 | V Boys Tennis | CIAC Class S State Tournament | Away | TBA | ||
| Sat., 5/27 | V Girls Tennis | CIAC Class S State Tournament | Away | TBA | ||
| Tue., 5/30 | V Boys Golf | BL All Star Tournament | Away - Fairview Farm CC | TBA | ||
| Thu., 6/1 | V Boys Outdoor Track | CIAC Class S Championships | Away - Willow Brook Park, New Britain | 3:00 p.m. | ||
| Thu., 6/1 | V Girls Outdoor Track | CIAC Class S State Tournament | Away - Willow Brook Park, New Britain | 3:00 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC Open Championships | Away - Willow Brook Park, New Britain | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC Open Championships | Away - Willow Brook Park, New Britain | 1:30 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathalon, Hammer Throw and Steeplechase, and Heptathalon | Away - Willow Brook Park, New Britain | TBA | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Decathalon, Hammer Throw and Steeplechase, and Heptathalon | Away - Willow Brook Park, New Britain | TBA | ||