| Gilbert 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 400 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Housatonic Regional | Home - Gilbert [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Terryville | Away - Lower Fisher Elementary [Directions] | TBA | ||
| TBA | JV Baseball | Thomaston | Home - Gilbert [Directions] | TBA | ||
| TBA | FR Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 3:45 p.m. | 2:40 p.m. | |
| TBA | JV Football | Canton | Home - Gilbert [Directions] | TBA | ||
| TBA | JV Boys Soccer | Thomaston | Away - Nystroms Park [Directions] | TBA | ||
| Fri., 9/8 | V Football | Old Saybrook | Home - Gilbert [Directions] | L 14-49 | ||
| Fri., 9/8 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | T 3-3 | ||
| Fri., 9/8 | JV Boys Soccer | Wamogo | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 9/8 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | W 3-1 | 2:40 p.m. | |
| Fri., 9/8 | V Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | L 0-3 | ||
| Fri., 9/8 | JV Girls Volleyball | Northwestern | Away - Northwestern HS [Directions] | 4:00 p.m. | ||
| Sat., 9/9 | V Boys Cross Country | Windham Invitational | Away - Windham HS | 9:30 a.m. | 7:00 a.m. | |
| Sat., 9/9 | JV Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 1:00 p.m. | 10:30 a.m. | |
| Sat., 9/9 | V Girls Cross Country | Windham Invitational | Away - Windham HS | 9:30 a.m. | 7:00 a.m. | |
| Mon., 9/11 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | L 0-7 | ||
| Tue., 9/12 | V Boys Cross Country | Wamogo | Away - White Memorial (HS XC Course) [Directions] | 4:15 p.m. | 2:40 p.m. | |
| Tue., 9/12 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | L 2-6 | 2:40 p.m. | |
| Tue., 9/12 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | 2:40 p.m. | |
| Tue., 9/12 | V Girls Cross Country | Wamogo | Away - White Memorial (HS XC Course) [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Tue., 9/12 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 0-3 | 2:40 p.m. | |
| Tue., 9/12 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Thu., 9/14 | V Girls Volleyball | Kaynor Tech | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Thu., 9/14 | JV Girls Volleyball | Kaynor Tech | Home - Gilbert Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/15 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | W 1-0 | ||
| Fri., 9/15 | JV Boys Soccer | Terryville | Home - Walker Field [Directions] | 5:00 p.m. | ||
| Fri., 9/15 | V Girls Soccer | Terryville | Away - New Terryville HS [Directions] | L 2-3 | 2:40 p.m. | |
| Fri., 9/15 | V Girls Volleyball | Terryville | Away - New Terryville HS [Directions] | L 0-3 | 2:40 p.m. | |
| Fri., 9/15 | JV Girls Volleyball | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Sat., 9/16 | V Boys Cross Country | Stratton Brook Invitational | Away | 10:00 a.m. | 8:00 a.m. | |
| Sat., 9/16 | V Football | Rockville | Home - Gilbert [Directions] | W 28-16 | ||
| Sat., 9/16 | V Girls Cross Country | Stratton Brook Invitational | Away | 10:00 a.m. | 8:00 a.m. | |
| Mon., 9/18 | JV Football | Rockville | Away - RHS football field [Directions] | 4:15 p.m. | 2:30 p.m. | |
| Mon., 9/18 | V Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | L 0-3 | 2:15 p.m. | |
| Mon., 9/18 | JV Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | 4:45 p.m. | 2:15 p.m. | |
| Tue., 9/19 | V Boys Cross Country | Litchfield, Northwestern | Away [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Tue., 9/19 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | T 0-0 | 2:30 p.m. | |
| Tue., 9/19 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Tue., 9/19 | V Girls Cross Country | Litchfield, Northwestern | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Tue., 9/19 | V Girls Soccer | Shepaug Valley | Home - Walker Field [Directions] | L 0-8 | ||
| Wed., 9/20 | V Girls Volleyball | Newington | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Wed., 9/20 | JV Girls Volleyball | Newington | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/22 | V Boys Soccer | Thomaston | Away - Highwood Farm [Directions] | W 2-0 | 2:40 p.m. | |
| Fri., 9/22 | V Girls Soccer | Thomaston | Home - Walker Field [Directions] | L 2-5 | ||
| Sat., 9/23 | V Boys Cross Country | Winding Trails Invitational | Away | 9:00 a.m. | 7:00 a.m. | |
| Sat., 9/23 | V Football | Stafford/East Windsor/Somers | Home - Gilbert [Directions] | L 6-27 | ||
| Sat., 9/23 | V Girls Cross Country | Winding Trails Invitational | Away | 9:00 a.m. | 7:00 a.m. | |
| Mon., 9/25 | JV Football | Stafford/East Windsor/Somers | Away - Stafford HS [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 9/25 | V Girls Volleyball | Goodwin Tech | Away - GOODWIN GYMNASIUM [Directions] | L 0-3 | 2:30 p.m. | |
| Mon., 9/25 | JV Girls Volleyball | Goodwin Tech | Away - GOODWIN GYMNASIUM [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 9/26 | V Boys Cross Country | Lewis Mills, Wamogo | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | T 0-0 | ||
| Tue., 9/26 | JV Boys Soccer | Housatonic Regional | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Lewis Mills, Wamogo | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Girls Soccer | Housatonic Regional | Away - Housatonic [Directions] | L 1-8 | 2:40 p.m. | |
| Tue., 9/26 | V Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Tue., 9/26 | JV Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Nonnewaug | Away - NHS Varsity Soccer Field [Directions] | L 2-5 | 2:30 p.m. | |
| Thu., 9/28 | JV Boys Soccer | Nonnewaug | Away - NHS - JV Soccer Field [Directions] | 3:45 p.m. | 2:40 p.m. | |
| Fri., 9/29 | V Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | L 1-9 | ||
| Fri., 9/29 | V Girls Volleyball | Housatonic Regional | Away - Housatonic [Directions] | W 3-1 | 2:40 p.m. | |
| Fri., 9/29 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Sat., 9/30 | V Football | Canton | Away - Canton H.S. Turf [Directions] | W 38-8 | 11:00 a.m. | |
| Tue., 10/3 | V Boys Cross Country | Nonnewaug, Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Tue., 10/3 | V Boys Soccer | Lewis Mills | Home - Walker Field [Directions] | L 0-8 | ||
| Tue., 10/3 | JV Boys Soccer | Lewis Mills | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Nonnewaug, Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Tue., 10/3 | V Girls Soccer | Lewis Mills | Away - Lewis Mills Varsity Soccer Field [Directions] | L 1-8 | 2:40 p.m. | |
| Tue., 10/3 | V Girls Volleyball | Northwestern | Home - Gilbert HS [Directions] | L 0-3 | 3:15 p.m. | Drop only |
| Tue., 10/3 | JV Girls Volleyball | Northwestern | Home - Gilbert HS [Directions] | 4:00 p.m. | 3:15 p.m. | Drop only |
| Thu., 10/5 | V Boys Soccer | Northwestern | Home - Walker Field [Directions] | L 1-3 | ||
| Thu., 10/5 | JV Boys Soccer | Northwestern | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | L 0-2 | 3:00 p.m. | Drop only |
| Sat., 10/7 | V Boys Cross Country | Wickham Invitational | Away | 10:00 a.m. | 8:30 a.m. | |
| Sat., 10/7 | V Football | Windsor Locks/Suffield/East Granby | Away - Suffield HS [Directions] | W 34-20 | 4:00 p.m. | |
| Sat., 10/7 | V Girls Cross Country | Wickham Invitational | Away | 10:00 a.m. | 8:30 a.m. | |
| Tue., 10/10 | V Boys Cross Country | Thomaston, Shepaug Valley | Away - Black Rock State Park [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Tue., 10/10 | JV Football | Windsor Locks/Suffield/East Granby | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Terryville | Away - New Terryville HS [Directions] | L 2-5 | 2:40 p.m. | |
| Tue., 10/10 | JV Boys Soccer | Terryville | Away - Upper Fisher Field [Directions] | 3:45 p.m. | 2:40 p.m | |
| Tue., 10/10 | V Girls Cross Country | Thomaston, Shepaug Valley | Away - Black Rock State Park [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Tue., 10/10 | V Girls Soccer | Terryville | Home - Walker Field [Directions] | L 1-4 | ||
| Tue., 10/10 | V Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | W 3-1 | ||
| Tue., 10/10 | JV Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | W 7-1 | 2:40 p.m. | |
| Thu., 10/12 | JV Boys Soccer | Wamogo | Away - Wamogo JV Soccer Field [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Thu., 10/12 | V Girls Soccer | Wamogo | Home - Walker Field [Directions] | W 3-0 | ||
| Fri., 10/13 | V Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Fri., 10/13 | JV Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | 3:30 p.m. | ||
| Sat., 10/14 | V Girls Volleyball | Plainfield | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Sat., 10/14 | JV Girls Volleyball | Plainfield | Home - Gilbert Gym [Directions] | 1:30 p.m. | ||
| Mon., 10/16 | V Boys Cross Country | Housatonic Regional | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Cross Country | Housatonic Regional | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | L 2-8 | 2:40 p.m. | |
| Mon., 10/16 | V Girls Volleyball | Cheney Tech | Home - Gilbert Gym [Directions] | L 2-3 | ||
| Mon., 10/16 | JV Girls Volleyball | Cheney Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Litchfield | Home - Walker Field [Directions] | L 1-3 | ||
| Tue., 10/17 | JV Boys Soccer | Litchfield | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 10/17 | V Girls Volleyball | Terryville | Home - Gilbert Gym [Directions] | L 0-2 | ||
| Tue., 10/17 | JV Girls Volleyball | Terryville | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Girls Volleyball | Jonathan Law | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Thu., 10/19 | JV Girls Volleyball | Jonathan Law | Home - Gilbert Gym [Directions] | 5:15 p.m. | ||
| Fri., 10/20 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | L 1-2 | ||
| Fri., 10/20 | JV Boys Soccer | Shepaug Valley | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Fri., 10/20 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | L 0-7 | 2:30 p.m. | |
| Sat., 10/21 | V Football | Coventry/Windham Tech/Bolton/Lyman | Home - Gilbert [Directions] | L 20-42 | Homecoming | |
| Mon., 10/23 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Away - Larry A. Pietrantonio Athletic Field Complex [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 10/24 | V Girls Volleyball | Sheehan | Away - Sheehan HS Gymnasium [Directions] | L 0-3 | 2:30 p.m. | |
| Tue., 10/24 | JV Girls Volleyball | Sheehan | Away - Sheehan HS Gymnasium [Directions] | 5:00 p.m. | 2:30 p.m. | |
| Wed., 10/25 | V Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | W 3-0 | 2:40 p.m. | |
| Wed., 10/25 | JV Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 4:00 p.m. | 2:40 p.m. | |
| Thu., 10/26 | V Boys Soccer | Thomaston | Home - Walker Field [Directions] | L 0-3 | ||
| Thu., 10/26 | JV Boys Soccer | Thomaston | Home - Walker Field [Directions] | 5:00 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Thomaston | Away - Highwood Farms Field [Directions] | T 1-1 | 2:40 p.m. | |
| Fri., 10/27 | V Football | Ellington | Away - Ellington HS [Directions] | L 0-26 | 3:30 p.m. | |
| Fri., 10/27 | V Boys Soccer | Housatonic Regional | Away - Housatonic [Directions] | L 0-6 | 2:40 | |
| Fri., 10/27 | JV Boys Soccer | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | 2:40 p.m. | |
| Fri., 10/27 | V Girls Soccer | Housatonic Regional | Home - Walker Field [Directions] | L 1-7 | ||
| Fri., 10/27 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L 0-3 | 2:30 p.m. | |
| Fri., 10/27 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Sat., 10/28 | JV Football | Ellington | Home - Gilbert [Directions] | Cancelled | ||
| Wed., 11/1 | V Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | W 3-1 | ||
| Wed., 11/1 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 11/2 | V Boys Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | L 1-5 | 3:00 p.m. | Drop only |
| Thu., 11/2 | JV Boys Soccer | Northwestern | Away - Northwestern JV field [Directions] | 3:30 p.m. | 3:00 p.m. | Drop only |
| Thu., 11/2 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | L 0-5 | ||
| Fri., 11/3 | V Football | Granby/Canton | Home - Gilbert [Directions] | W 33-13 | Senior Night | |
| Sat., 11/4 | JV Football | Granby/Canton | Away - Granby Memorial HS [Directions] | 10:00 a.m. | 8:30 a.m. | Senior Day |
| Thu., 11/9 | V Football | SMSA Coop | Away - Dillon Stadium [Directions] | L 19-24 | 4:00 p.m. | |
| Sat., 11/11 | JV Football | SMSA Coop | Home - Gilbert [Directions] | 11:00 a.m. | ||
| Tue., 11/21 | V Football | WCA | Away - Municipal Stadium [Directions] | W 29-22 | 4:00 p.m. | |
| Wed., 12/13 | V Wrestling | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | 6:00 weigh in | |
| Wed., 12/13 | V Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | W 57-31 | ||
| Wed., 12/13 | JV Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/16 | V Wrestling | Derby Invitational | Away - Derby HS | 10:00 a.m. | ||
| Mon., 12/18 | V Girls Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | W 57-36 | 3:00 p.m. | |
| Mon., 12/18 | JV Girls Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 4:30 p.m. | 3:00 p.m. | |
| Tue., 12/19 | V Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | W 74-65 | ||
| Tue., 12/19 | JV Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/19 | FR Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/19 | V Girls Basketball | Thomaston | Away [Directions] | L 37-52 | 4:15 p.m. | |
| Tue., 12/19 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Wed., 12/20 | V Wrestling | Terryville-Thomaston | Home - Gilbert Gym [Directions] | 6:30 p.m. | ||
| Thu., 12/21 | V Boys Swimming and Diving | Woodland | Away - Woodland Pool [Directions] | 4:30 p.m. | ||
| Sat., 12/23 | V Wrestling | RHAM Duals | Away | TBA | ||
| Tue., 12/26 | V Wrestling | Northwestern | Home - Gilbert Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/27 | V Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | W 49-42 | ||
| Wed., 12/27 | JV Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Thu., 12/28 | V Wrestling | KSA Disney Duals | Away - Orlando, FL | TBA | ||
| Fri., 12/29 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 12/29 | V Wrestling | KSA Disney Duals | Away - Orlando, FL | TBA | ||
| Fri., 12/29 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L 46-39 | 11:30 a.m. | |
| Fri., 12/29 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 1:00 p.m. | 11:30 a.m. | |
| Sat., 12/30 | V Boys Swimming and Diving | Northwestern | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 12/30 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Wed., 1/3 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | L 57-77 | 4:15 p.m. | |
| Wed., 1/3 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Wed., 1/3 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 3:45 p.m. | 2:40 | |
| Wed., 1/3 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Wed., 1/3 | V Wrestling | TBA | Home - Gilbert Gym [Directions] | Cancelled | ||
| Wed., 1/3 | V Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | W 41-39 | ||
| Wed., 1/3 | JV Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/6 | V Wrestling | Glouchester MA | Away | Cancelled | ||
| Tue., 1/9 | V Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | W 69-44 | ||
| Tue., 1/9 | JV Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Terryville | Away - New Terryville HS [Directions] | W 54-33 | 4:15 p.m. | |
| Tue., 1/9 | JV Girls Basketball | Terryville | Away - New Terryville HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Wed., 1/10 | V Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | L 29-71 | ||
| Wed., 1/10 | JV Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/10 | FR Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/10 | V Boys Swimming and Diving | Litchfield | Away - CJR Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/10 | V Wrestling | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/11 | JV Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/11 | JV Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | L 44-60 | ||
| Fri., 1/12 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 3:45 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | L 46-33 | Varsity Doubleheader | |
| Sat., 1/13 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/13 | V Wrestling | Gilbert Duals | Home - Gilbert Gym [Directions] | Cancelled | ||
| Mon., 1/15 | V Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | W 45-42 | ||
| Mon., 1/15 | JV Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Mon., 1/15 | V Boys Swimming and Diving | Litchfield, Granby Memorial | Home - Winsted YMCA [Directions] | 1:45 p.m. | ||
| Thu., 1/18 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | L 61-77 | 4:00 p.m. | |
| Thu., 1/18 | JV Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Thu., 1/18 | FR Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 3:45 p.m. | 2:30 | |
| Thu., 1/18 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | ||
| Thu., 1/18 | V Girls Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | W 60-49 | ||
| Thu., 1/18 | JV Girls Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | W 54-44 | ||
| Fri., 1/19 | JV Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/19 | V Wrestling | Avon, Farmington, Terryville-Thomaston | Away - Avon HS--Gym Two [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | L 36-43(OT) | 4:15 p.m. | |
| Fri., 1/19 | JV Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Sat., 1/20 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/20 | V Boys Swimming and Diving | Wamogo, Lewis Mills | Away - Giamatti Center - Bristol [Directions] | 7:00 p.m. | 6:15 Warm up | |
| Sat., 1/20 | V Girls Basketball | Woodstock Academy | Home - Gilbert Gym [Directions] | L 37-64 | ||
| Tue., 1/23 | V Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | W 78-45 | ||
| Tue., 1/23 | JV Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Housatonic Regional | Away - Housatonic [Directions] | L 26-52 | 4:00 p.m. | |
| Tue., 1/23 | JV Girls Basketball | Housatonic Regional | Away - Housatonic [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Wed., 1/24 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss [Directions] | 5:30 p.m. | ||
| Wed., 1/24 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Wed., 1/24 | V Wrestling | St. Paul Catholic | Home - Gilbert Gym [Directions] | 6:30 p.m. | ||
| Thu., 1/25 | V Boys Basketball | O'Brien Tech | Home - Gilbert Gym [Directions] | W 69-50 | ||
| Thu., 1/25 | JV Boys Basketball | O'Brien Tech | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | W 68-52 | 4:15 p.m. | |
| Fri., 1/26 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Fri., 1/26 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 3:45 p.m. | 2:40 p.m. | |
| Fri., 1/26 | V Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | W 49-44 | ||
| Fri., 1/26 | JV Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/27 | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 12:00 p.m. | ||
| Sat., 1/27 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/27 | V Wrestling | Portland Tourney | Away | TBA | ||
| Sat., 1/27 | FR Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 10:00 a.m. | ||
| Mon., 1/29 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | L 34-86 | 4:15 p.m. | |
| Mon., 1/29 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | W 40-24 | 4:15 p.m. | |
| Mon., 1/29 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Tue., 1/30 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L Forfeit | 4:00 p.m. | |
| Tue., 1/30 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | Cancelled | 4:00 p.m. | |
| Tue., 1/30 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | W 50-42 | ||
| Tue., 1/30 | JV Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/31 | JV Boys Basketball | Ansonia | Home - Gilbert Gym [Directions] | 7:00 p.m. | 2:45 p.m. | |
| Wed., 1/31 | FR Boys Basketball | Ansonia | Home - Gilbert Gym [Directions] | 5:30 p.m. | 2:00 p.m. | |
| Wed., 1/31 | V Wrestling | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Sat., 2/3 | V Boys Swimming and Diving | Wamogo | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/3 | V Wrestling | Woodstock Invitational | Away | TBA | ||
| Mon., 2/5 | V Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | L 45-91 | ||
| Mon., 2/5 | JV Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Mon., 2/5 | FR Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/5 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | W 42-37 | 4:15 p.m. | |
| Mon., 2/5 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Tue., 2/6 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 28-71 | 4:15 p.m. | |
| Tue., 2/6 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Tue., 2/6 | V Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | L 54-33 | ||
| Tue., 2/6 | JV Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/7 | V Wrestling | TBA | Away | Cancelled | ||
| Thu., 2/8 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:00 p.m. | No Bus | |
| Thu., 2/8 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Thu., 2/8 | JV Girls Basketball | Northwestern | Away - Northwestern HS [Directions] | 5:30 p.m. | No Bus | |
| Fri., 2/9 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | L 36-57 | No Bus | |
| Fri., 2/9 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Northwestern | Away - Northwestern HS [Directions] | L 39-51 | No Bus | |
| Sat., 2/10 | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Boys Swimming and Diving | Lewis Mills | Away - Giamatti Center - Bristol [Directions] | 7:00 p.m. | ||
| Sat., 2/10 | FR Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 12:00 p.m. | ||
| Mon., 2/12 | V Boys Basketball | Terryville | Away - New Terryville HS [Directions] | L 47-62 | 4:15 p.m. | |
| Mon., 2/12 | JV Boys Basketball | Terryville | Away - New Terryville HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Mon., 2/12 | V Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | W 53-38 | ||
| Mon., 2/12 | JV Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Thu., 2/15 | V Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | L 55-76 | ||
| Thu., 2/15 | JV Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/15 | FR Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Thu., 2/15 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | W 44-41 | 4:00 p.m. | |
| Thu., 2/15 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Sat., 2/17 | V Boys Swimming and Diving | Gilbert | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/17 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Mon., 2/19 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Tue., 2/20 | V Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | L 48-56 | 4:15 p.m. | |
| Tue., 2/20 | JV Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Tue., 2/20 | FR Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | 2:40 p.m. | |
| Tue., 2/20 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Wed., 2/21 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss [Directions] | 5:30 p.m. | ||
| Fri., 2/23 | V Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | W 71-69 | 4:00 p.m. | |
| Fri., 2/23 | JV Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Fri., 2/23 | FR Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | 2:30 | |
| Fri., 2/23 | V Boys Swimming and Diving | Wamogo | Away - CJR Pool [Directions] | 4:30 p.m. | ||
| Sat., 2/24 | V Boys Swimming and Diving | Splash | Away | TBA | ||
| Sat., 3/31 | V Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | L 3-5 | 11:30 a.m. | |
| Sat., 3/31 | JV Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | 3:30 p.m. | ||
| Sat., 3/31 | V Softball | Thomaston | Home - Rowley Field [Directions] | L 18-3 | ||
| Thu., 4/5 | V Boys Tennis | Shepaug Valley | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Thu., 4/5 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | L 0-7 | ||
| Mon., 4/9 | V Baseball | Terryville | Away - New Terryville HS [Directions] | L 5-2 | 2:30 | |
| Mon., 4/9 | V Boys Tennis | Thomaston | Away - Nystroms Park [Directions] | L 2-3 | ||
| Mon., 4/9 | V Softball | Terryville | Home - Rowley Field [Directions] | W 6-5 | ||
| Mon., 4/9 | V Girls Tennis | Thomaston | Home - Gilbert [Directions] | W 7-0 | ||
| Wed., 4/11 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | L 12-2 | ||
| Wed., 4/11 | JV Baseball | Nonnewaug | Away - Nonnewaug Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/11 | V Boys Golf | Lewis Mills | Away - Fairview Farms Golf Course - Harwinton [Directions] | Gilbert 177 Mills 184 | ||
| Wed., 4/11 | V Boys Outdoor Track | Wamogo | Away - Plumb Hill Litchfield [Directions] | 4:00 p.m. | ||
| Wed., 4/11 | V Boys Tennis | Housatonic Regional | Home - Gilbert [Directions] | L 0-5 | ||
| Wed., 4/11 | V Girls Outdoor Track | Wamogo | Away - Plumb Hill Litchfield [Directions] | 4:00 p.m. | ||
| Wed., 4/11 | V Softball | Nonnewaug | Away - Nonnewaug HS Varsity Field [Directions] | L 3-10 | ||
| Wed., 4/11 | V Girls Tennis | Housatonic Regional | Away - Housatonic [Directions] | W 4-3 | ||
| Thu., 4/12 | V Boys Golf | Northwestern | Home - Greenwood Country Club [Directions] | Gilbert171 Nw #7 203 | ||
| Thu., 4/12 | V Softball | Lewis Mills | Home - Rowley Field [Directions] | L 9-6 | ||
| Fri., 4/13 | V Baseball | Wamogo | Home - Walker Field [Directions] | W 8-1 | ||
| Fri., 4/13 | V Boys Tennis | Litchfield | Away - Litchfield HS [Directions] | L 0-5 | ||
| Fri., 4/13 | V Softball | Wamogo/Litchfield | Home - Rowley Field [Directions] | L 16-0 | ||
| Fri., 4/13 | V Girls Tennis | Litchfield | Home - Gilbert [Directions] | L 0-7 | ||
| Sat., 4/14 | JV Softball | NW Jamboree | Away - NWR7 | 10:00 a.m. | ||
| Sat., 4/14 | JV Softball | NW Jamboree | Away - NWR7 | 11:30 a.m. | ||
| Tue., 4/17 | V Boys Outdoor Track | Shepaug Valley | Home - NW Reg 7 Track [Directions] | 2:00 p.m. | ||
| Tue., 4/17 | V Girls Outdoor Track | Shepaug Valley | Home - NW Reg 7 Track [Directions] | 2:00 p.m. | ||
| Wed., 4/18 | V Baseball | Litchfield | Home - Walker Field [Directions] | L 5-12 | ||
| Wed., 4/18 | V Softball | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | W 20-3 | ||
| Wed., 4/18 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | W 4-3 | ||
| Fri., 4/20 | V Baseball | Northwestern | Home - Walker Field [Directions] | L 10-0 | Yes | |
| Fri., 4/20 | JV Baseball | Northwestern | Home - Walker Field [Directions] | 1:00 p.m. | ||
| Fri., 4/20 | V Softball | Northwestern | Home - Rowley Field [Directions] | L 20-3 | ||
| Mon., 4/23 | V Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | L 9-0 | 2:30 | |
| Mon., 4/23 | JV Baseball | Shepaug Valley | Away - Shepaug Valley HS JV Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/23 | V Boys Outdoor Track | Housatonic Regional | Away - Housatonic Track [Directions] | 4:00 p.m. | ||
| Mon., 4/23 | V Boys Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | L 0-5 | ||
| Mon., 4/23 | V Girls Outdoor Track | Housatonic Regional | Away - Housatonic Track [Directions] | 4:00 p.m. | ||
| Mon., 4/23 | V Softball | Shepaug Valley | Home - Rowley Field [Directions] | L 12-1 | ||
| Mon., 4/23 | V Girls Tennis | Northwestern | Home - Gilbert [Directions] | W 5-2 | ||
| Tue., 4/24 | V Baseball | Wolcott Tech | Away - Fuessenich Park [Directions] | W 6-0 | 4:00 | |
| Tue., 4/24 | V Boys Golf | Terryville, Wamogo | Away - Pequabuck Golf Course [Directions] | Gilbert 173 Terryville/Thomaston 212 Wamogo 270 | ||
| Tue., 4/24 | V Boys Tennis | Lewis Mills | Home - Gilbert [Directions] | L 0-5 | ||
| Tue., 4/24 | V Softball | Wolcott Tech | Home - Rowley Field [Directions] | W 14-9 | ||
| Tue., 4/24 | V Girls Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | L 3-4 | ||
| Thu., 4/26 | V Boys Golf | Litchfield, Northwestern | Away - Litchfield CC [Directions] | Gilbert 176 Litchfield 244 NW 7 209 | ||
| Sat., 4/28 | V Baseball | Housatonic Regional | Home - Walker Field [Directions] | W 2-1 | ||
| Sat., 4/28 | JV Softball | NW Jamboree | Away - NWR7 | 10:00 a.m. | Postponed | |
| Sat., 4/28 | JV Softball | NW Jamboree | Away - NWR7 | 11:30 a.m. | Postponed | |
| Mon., 4/30 | V Baseball | Lewis Mills | Home - Walker Field [Directions] | L 10-4 | ||
| Mon., 4/30 | V Boys Golf | Lewis Mills, Terryville | Home - Greenwood Country Club [Directions] | Gilbert 171 Lewis Mills 175 Terryville/ Thomaston 239 | ||
| Mon., 4/30 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | L 1-4 | ||
| Mon., 4/30 | V Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | L 1-8 | ||
| Mon., 4/30 | V Girls Tennis | Shepaug Valley | Home - Gilbert [Directions] | L 1-6 | ||
| Tue., 5/1 | V Baseball | Thomaston | Home - Walker Field [Directions] | W 4-1 | ||
| Tue., 5/1 | V Boys Golf | Wolcott Tech | Home - Greenwood Country Club [Directions] | Gilbert 167 OWTS 205 | ||
| Tue., 5/1 | V Boys Outdoor Track | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Girls Outdoor Track | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | ||
| Wed., 5/2 | V Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | W 17-0 | 2:30 | |
| Wed., 5/2 | V Boys Tennis | Thomaston | Home - Gilbert [Directions] | L 1-4 [Detailed Results] | ||
| Wed., 5/2 | V Softball | Wamogo/Litchfield | Away - Wamogo Varsity Softball Field [Directions] | L 5-3 | ||
| Wed., 5/2 | V Girls Tennis | Thomaston | Away - Nystroms Park [Directions] | W 7-0 | ||
| Thu., 5/3 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | L 7-3 | 2:30 | |
| Thu., 5/3 | JV Baseball | Lewis Mills | Away - Lewis Mills JV Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/3 | V Boys Golf | Woodland Tournament | Away | Gilbert 367 | ||
| Thu., 5/3 | V Boys Outdoor Track | Lewis Mills | Away - Lewis Mills Track [Directions] | 4:00 p.m. | ||
| Thu., 5/3 | V Boys Outdoor Track | Nonnewaug | Home - Lewis Mills Track [Directions] | 4:00 p.m. | ||
| Thu., 5/3 | V Girls Outdoor Track | Lewis Mills | Away - Lewis Mills Track [Directions] | 4:00 p.m. | ||
| Thu., 5/3 | V Girls Outdoor Track | Nonnewaug | Home - Lewis Mills Track [Directions] | 4:00 p.m. | ||
| Thu., 5/3 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | L 12-0 | ||
| Fri., 5/4 | V Boys Tennis | Housatonic Regional | Away - Housatonic [Directions] | L 0-5 | ||
| Fri., 5/4 | V Girls Tennis | Housatonic Regional | Home - Gilbert [Directions] | W 5-2 | ||
| Sat., 5/5 | JV Baseball | Wamogo | Home - Walker Field [Directions] | Cancelled | ||
| Mon., 5/7 | V Baseball | Terryville | Home - Walker Field [Directions] | W 10-0 | ||
| Mon., 5/7 | JV Baseball | Terryville | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Mon., 5/7 | V Boys Golf | Litchfield | Home - Greenwood Country Club [Directions] | Gilbert 161 Litchfield 254 | ||
| Mon., 5/7 | V Boys Outdoor Track | Thomaston | Away - Nystroms Park [Directions] | 4:00 p.m. | ||
| Mon., 5/7 | V Boys Tennis | Litchfield | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Mon., 5/7 | V Girls Outdoor Track | Thomaston | Away - Nystroms Park [Directions] | 4:00 p.m. | ||
| Mon., 5/7 | V Softball | Terryville | Away - New Terryville HS [Directions] | L 2-13 | ||
| Tue., 5/8 | V Boys Tennis | Wamogo | Home - Gilbert [Directions] | L 2-3 [Detailed Results] | ||
| Wed., 5/9 | V Baseball | Nonnewaug | Away - Municipal Stadium - Waterbury [Directions] | L 3-0 | 5:00 | |
| Wed., 5/9 | JV Baseball | Nonnewaug | Away - Nonnewaug HS [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 5/9 | V Boys Golf | Jack Stigberg Memorial Golf Tournament | Away | 74 | ||
| Wed., 5/9 | V Boys Tennis | Nonnewaug | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Wed., 5/9 | V Boys Tennis | Nonnewaug | Home - Gilbert [Directions] | L 2-3 [Detailed Results] | ||
| Wed., 5/9 | V Softball | Nonnewaug | Home - Rowley Field [Directions] | L 22-5 | ||
| Wed., 5/9 | V Girls Tennis | Nonnewaug | Away - Edgewood Tennis and Bath [Directions] | L 1-6 | ||
| Wed., 5/9 | V Girls Tennis | Nonnewaug | Away - Edgewood Tennis and Bath [Directions] | L 1-6 | ||
| Thu., 5/10 | V Baseball | Housatonic Regional | Away - Housatonic Field [Directions] | W 1-0 | 2:30 | |
| Thu., 5/10 | JV Baseball | Housatonic Regional | Away - HS JV Field [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Boys Golf | Lewis Mills, Wamogo | Away - Fairview Farms Golf Course - Harwinton [Directions] | Gilbert 170 Lewis Mills 174 Wamogo 273 | ||
| Thu., 5/10 | V Boys Outdoor Track | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Girls Outdoor Track | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | ||
| Fri., 5/11 | V Boys Outdoor Track | Torrington Varsity Alumni Club Track Invitational | Away - Torrington HS | 4:00 p.m. | 10am Field/10:30 Track Events | |
| Fri., 5/11 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | L 0-5 | ||
| Fri., 5/11 | V Girls Outdoor Track | Torrington Varsity Alumni Club Track Invitational | Away - Torrington HS | 4:00 p.m. | 10am Field / 10:30 Track Events | |
| Fri., 5/11 | V Softball | Housatonic Regional | Away - HRVHS [Directions] | L 15-21 | ||
| Fri., 5/11 | V Softball | Housatonic Regional | Home - HRVHS [Directions] | W 12-5 | ||
| Fri., 5/11 | V Girls Tennis | Wamogo | Home - Gilbert [Directions] | L 3-4 | ||
| Sat., 5/12 | JV Softball | NW Jamboree | Away - NWR7 | Cancelled | ||
| Sat., 5/12 | JV Softball | NW Jamboree | Away - NWR7 | Cancelled | ||
| Mon., 5/14 | V Boys Golf | Housatonic Regional, Nonnewaug | Away - Sharon Country Club [Directions] | Gilbert 169 Housatonic 204 Nonnewaug 220 | ||
| Mon., 5/14 | V Boys Outdoor Track | Northwestern, Wolcott Tech | Away - Northwestern HS [Directions] | 4:00 p.m. | ||
| Mon., 5/14 | V Boys Tennis | Northwestern | Home - Gilbert [Directions] | L 2-3 [Detailed Results] | ||
| Mon., 5/14 | V Girls Outdoor Track | Northwestern, Wolcott Tech | Away - Northwestern HS [Directions] | 4:00 p.m. | ||
| Mon., 5/14 | V Girls Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | L 1-6 | ||
| Wed., 5/16 | V Baseball | Litchfield | Away - Litchfield HS Baseball Field [Directions] | W 7-2 | 2:30 | |
| Wed., 5/16 | V Softball | Litchfield | Home - Rowley Field [Directions] | W Forfeit | ||
| Thu., 5/17 | V Boys Golf | Housatonic Regional, Shepaug Valley | Home - Greenwood Country Club [Directions] | Gilbert 165 Housatonic 198 Shepaug 227 | ||
| Thu., 5/17 | V Boys Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | L 0-5 [Detailed Results] | ||
| Thu., 5/17 | V Softball | Canton | Home - Rowley Field [Directions] | L 10-6 | ||
| Thu., 5/17 | V Girls Tennis | Lewis Mills | Home - Gilbert [Directions] | L 2-5 | ||
| Fri., 5/18 | V Baseball | Canton | Home - Walker Field [Directions] | L 18-1 | ||
| Fri., 5/18 | JV Baseball | Canton | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Fri., 5/18 | V Softball | Northwestern | Away - Northwestern Varsity Field [Directions] | L 2-17 | ||
| Mon., 5/21 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | L 3-14 | ||
| Mon., 5/21 | V Boys Golf | Wolcott Tech, Housatonic Regional | Away - Fairview Farms [Directions] | Gilbert 174 OWTS 202 | ||
| Mon., 5/21 | V Softball | Shepaug Valley | Away - Dick Ayer Field [Directions] | L 0-6 | ||
| Tue., 5/22 | V Boys Golf | Northwestern | Home - Greenwood Country Club [Directions] | Gilbert 168 NW 7 194 | ||
| Wed., 5/23 | V Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | L 15-5 | ||
| Thu., 5/24 | JV Baseball | Northwestern | Away - NWR [Directions] | 3:45 p.m. | ||
| Thu., 5/24 | V Boys Golf | Chappa Tournament | Away | TBA | ||
| Thu., 5/24 | V Girls Tennis | Litchfield | Away - Litchfield HS [Directions] | L 0-7 | ||
| Wed., 5/30 | V Boys Golf | Nonnewaug, Shepaug Valley | Away - Heritage Village CC [Directions] | Gilbert 167 Shepaug 217 Nonnewaug 205 | ||