| Gilbert 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 196 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 10/1 | V Boys Soccer | Thomaston | Away - Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | W 4-1 | |
| Thu., 10/1 | V Girls Soccer | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 0-6 | |
| Thu., 10/1 | V Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 10/1 | JV Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | Canceled | Cancelled | |
| Fri., 10/2 | V Boys Cross Country | Northwestern | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Fri., 10/2 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | L 4-1 | |
| Fri., 10/2 | V Girls Cross Country | Northwestern | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Fri., 10/2 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-1 | |
| Mon., 10/5 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 3:45 p.m. | L 0-3 | |
| Mon., 10/5 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 10/6 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 10/6 | V Girls Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 0-4 | |
| Thu., 10/8 | V Boys Cross Country | Litchfield | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Girls Cross Country | Litchfield | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Girls Soccer | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 10/8 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Thu., 10/8 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | Canceled | Cancelled | |
| Fri., 10/9 | V Boys Cross Country | Wamogo | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Fri., 10/9 | V Boys Soccer | Wolcott Tech | Home - Walker Field [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 10/9 | V Girls Cross Country | Wamogo | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Volleyball | Wolcott Tech | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 10/13 | JV Girls Volleyball | Wolcott Tech | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | ||
| Wed., 10/14 | V Boys Cross Country | Housatonic Regional | Away - Housatonic Valley Regional High-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | W 1-0 | |
| Wed., 10/14 | V Girls Cross Country | Housatonic Regional | Away - Housatonic Valley Regional High-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 0-6 | |
| Thu., 10/15 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 8-0 | |
| Thu., 10/15 | V Girls Volleyball | Terryville | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Thu., 10/15 | JV Girls Volleyball | Terryville | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | V Boys Cross Country | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | V Girls Cross Country | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | V Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Mon., 10/19 | JV Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 5-3 | |
| Tue., 10/20 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 10/22 | V Boys Cross Country | Nonnewaug | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | V Girls Cross Country | Nonnewaug | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/23 | V Boys Cross Country | Wolcott Tech | Away - John Minetto State Park [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 10/23 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 9-1 | |
| Fri., 10/23 | V Girls Cross Country | Wolcott Tech | Away - John Minetto State Park [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 10/23 | V Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 0-6 | |
| Mon., 10/26 | V Girls Volleyball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Mon., 10/26 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Boys Cross Country | Thomaston | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 3-1 | |
| Tue., 10/27 | V Girls Cross Country | Thomaston | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 10/28 | V Girls Volleyball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 10/28 | JV Girls Volleyball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | Canceled | Cancelled | |
| Wed., 11/4 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | T 2-2 | |
| Wed., 11/4 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:15 p.m. | L 0-3 | |
| Thu., 11/5 | V Boys Cross Country | Terryville | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Thu., 11/5 | V Girls Cross Country | Terryville | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Thu., 11/5 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 11/5 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/6 | V Boys Soccer | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 11/6 | V Girls Soccer | Wolcott Tech | Home - Walker Field [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Mon., 2/8 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | W 82-51 | |
| Mon., 2/8 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/8 | V Girls Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | L 54-30 | |
| Thu., 2/11 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | L 42-72 | |
| Thu., 2/11 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/11 | V Girls Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | W 37-29 | |
| Fri., 2/12 | V Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 54-77 | |
| Fri., 2/12 | JV Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:00 p.m. | L 46-16 | |
| Sat., 2/13 | V Boys Swimming and Diving | Wamogo | Home - Wamogo Regional HS-Winsted YMCA [Directions] | 3:30 p.m. | ||
| Wed., 2/17 | V Boys Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 79-53 | |
| Wed., 2/17 | JV Boys Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Wed., 2/17 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 3:00 p.m. | L 61-32 | |
| Sat., 2/20 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 2:00 p.m. | L 55-66 | |
| Sat., 2/20 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 12:30 p.m. | ||
| Sat., 2/20 | V Boys Swimming and Diving | Housatonic Regional | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Sat., 2/20 | V Girls Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | L 62-8 | |
| Tue., 2/23 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/27 | V Boys Swimming and Diving | Litchfield | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Mon., 3/1 | V Boys Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 6:15 p.m. | L 68-56 | |
| Mon., 3/1 | JV Boys Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 4:15 p.m. | ||
| Mon., 3/1 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | L 47-20 | |
| Tue., 3/2 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | L 65-54 | |
| Tue., 3/2 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 3/5 | V Boys Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 65-58 | |
| Fri., 3/5 | JV Boys Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Fri., 3/5 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | L 42-31 | |
| Sat., 3/6 | V Boys Swimming and Diving | Wamogo | Away - Wamogo Regional HS-Winsted YMCA [Directions] | 6:30 p.m. | ||
| Mon., 3/8 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 59-77 | |
| Mon., 3/8 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 3/8 | V Girls Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | L 54-27 | |
| Wed., 3/10 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 3:00 p.m. | L 49-69 | |
| Wed., 3/10 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Nonnewaug's Gym [Directions] | 4:30 p.m. | ||
| Wed., 3/10 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 3/10 | V Boys Swimming and Diving | Shepaug Valley | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:45 p.m. | ||
| Wed., 3/10 | V Girls Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | L 48-27 | |
| Thu., 3/11 | V Girls Basketball | Terryville | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | L 34-28 | |
| Fri., 3/12 | V Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | ||
| Fri., 3/12 | JV Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Fri., 3/12 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | L 51-30 | |
| Sat., 3/13 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 12:00 p.m. | W 40-27 | |
| Mon., 3/15 | V Boys Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 48-59 | |
| Mon., 3/15 | JV Boys Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Tue., 3/16 | V Girls Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 32-13 | |
| Wed., 3/17 | V Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | ||
| Wed., 3/17 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 3/18 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 3/19 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 43-77 | |
| Fri., 3/19 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 3/22 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 6:00 p.m. | L 22-37 | |
| Wed., 3/24 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:00 p.m. | ||
| Sat., 4/10 | V Baseball | Thomaston | Home - Walker Field [Directions] | 11:00 a.m. | L 16-0 | |
| Sat., 4/10 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 11:00 a.m. | L 0-14 | |
| Sat., 4/10 | V Girls Tennis | Housatonic Regional | Home - Gilbert School-Tennis Courts [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 4/13 | V Boys Outdoor Track | Housatonic Regional | Away - Housatonic Valley Regional High-Track [Directions] | 3:00 p.m. | ||
| Tue., 4/13 | V Girls Outdoor Track | Housatonic Regional | Away - Housatonic Valley Regional High-Track [Directions] | 3:00 p.m. | ||
| Wed., 4/14 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | L 18-1 | |
| Wed., 4/14 | V Softball | Northwestern | Home - Walker Field-Rowley Field [Directions] | 3:45 p.m. | L 2-20 | |
| Thu., 4/15 | JV Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | Postponed | ||
| Thu., 4/15 | V Boys Outdoor Track | Terryville | Away - Terryville HS-Track [Directions] | Postponed | ||
| Thu., 4/15 | V Girls Outdoor Track | Terryville | Away - Terryville HS-Track [Directions] | Postponed | ||
| Mon., 4/19 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Varsity Baseball Diamond [Directions] | 3:45 p.m. | L 12-2 | |
| Mon., 4/19 | JV Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-JV Baseball Diamond [Directions] | Postponed | ||
| Mon., 4/19 | V Boys Golf | Terryville | Home - Green woods Country Club [Directions] | 3:00 p.m. | Gilbert-264 Terryville/Thomaston-238 (Gilbert 0-1 League Record) | |
| Tue., 4/20 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 17-0 | |
| Tue., 4/20 | V Boys Outdoor Track | Litchfield | Home - Northwestern Regional H.S.-Track [Directions] | 3:15 p.m. | ||
| Tue., 4/20 | V Girls Outdoor Track | Litchfield | Home - Northwestern Regional H.S.-Track [Directions] | 3:30 p.m. | ||
| Tue., 4/20 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Softball [Directions] | 4:00 p.m. | L 0-17 | |
| Wed., 4/21 | V Boys Golf | Litchfield | Away - Litchfield Country Club [Directions] | 3:00 p.m. | Cancelled | |
| Thu., 4/22 | V Boys Golf | Wolcott Tech | Away - Torrington Country Club [Directions] | 3:00 p.m. | Gilbert-280 Wolcott Tech-221 Nonnewaug-239 (Non-League Match) | |
| Thu., 4/22 | V Softball | Housatonic Regional | Home - Walker Field-Rowley Field [Directions] | 3:45 p.m. | W 21-6 | |
| Fri., 4/23 | V Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 15-5 | |
| Fri., 4/23 | V Boys Outdoor Track | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Fri., 4/23 | V Girls Outdoor Track | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Fri., 4/23 | V Softball | Wamogo/Litchfield | Home - Walker Field-Rowley Field [Directions] | 3:45 p.m. | L 9-11 | |
| Fri., 4/23 | V Girls Tennis | Northwestern | Home - Gilbert School-Tennis Courts [Directions] | 3:00 a.m. | L 5-2 | |
| Sat., 4/24 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 9:30 a.m. | L 0-4 | |
| Mon., 4/26 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | L 10-3 | |
| Mon., 4/26 | V Boys Golf | Housatonic Regional, Wamogo | Away - Canaan Country Club [Directions] | 3:00 p.m. | Gilbert- 240 Housatonic- 199 Wamogo- 272 (Gilbert 1-2 League Record) | |
| Mon., 4/26 | V Softball | Terryville | Home - Walker Field-Rowley Field [Directions] | 3:45 p.m. | L 9-10 | |
| Mon., 4/26 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 4/27 | V Boys Outdoor Track | Nonnewaug | Home - Northwestern Regional H.S.-Track [Directions] | 3:30 p.m. | ||
| Tue., 4/27 | V Girls Outdoor Track | Nonnewaug | Home - Northwestern Regional H.S.-Track [Directions] | 3:30 p.m. | ||
| Wed., 4/28 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 13-9 | |
| Wed., 4/28 | V Boys Golf | Litchfield, Northwestern | Away - Litchfield Country Club [Directions] | 3:00 p.m. | Gilbert- 256 Northwestern- 217 Litchfield- 177 (Gilbert 1-3 League Record) *Match only against Litchfield* | |
| Wed., 4/28 | V Girls Tennis | Litchfield | Home - Gilbert School-Tennis Courts [Directions] | 3:30 p.m. | L 0-4 | |
| Thu., 4/29 | V Boys Golf | Housatonic Regional, Shepaug Valley | Home - Green woods Country Club [Directions] | 3:00 p.m. | ||
| Thu., 4/29 | JV Softball | Housatonic Regional | Away - Housatonic Valley Regional High-Softball Diamond [Directions] | 3:45 p.m. | ||
| Fri., 4/30 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 16-0 | |
| Fri., 4/30 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 4:00 p.m. | L 0-21 | |
| Fri., 4/30 | V Girls Tennis | Thomaston | Away - Nystrom Park-Nystroms Park courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 5/3 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 14-4 | |
| Mon., 5/3 | V Softball | Thomaston | Home - Walker Field-Rowley Field [Directions] | 4:00 p.m. | L 3-21 | |
| Tue., 5/4 | V Boys Golf | Shepaug Valley, Terryville | Away - Lake Waramaug Country Club [Directions] | 3:00 p.m. | Gilbert- 238 Shepaug- 251 Terryville/ Thomaston- 220 (Gilbert 2-4 League Record) | |
| Tue., 5/4 | V Boys Outdoor Track | Northwestern | Home - Northwestern Regional H.S.-Football Field [Directions] | 3:30 p.m. | ||
| Tue., 5/4 | V Girls Outdoor Track | Northwestern | Home - Northwestern Regional H.S.-Track [Directions] | 3:30 p.m. | ||
| Thu., 5/6 | V Baseball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | L 9-2 | |
| Thu., 5/6 | V Boys Golf | Northwestern, Wamogo | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:00 p.m. | Gilbert- 217 Northwestern- 221 Wamogo- 280 (Gilbert 4-4 League Record) | |
| Fri., 5/7 | V Baseball | Wolcott Tech | Home - Walker Field [Directions] | 3:45 p.m. | L 11-7 | |
| Fri., 5/7 | V Softball | Wolcott Tech | Home - Winsted Rowley Field [Directions] | 3:15 p.m. | L 6-13 | |
| Fri., 5/7 | V Girls Tennis | Shepaug Valley | Home - Gilbert School-Tennis Courts [Directions] | 3:30 p.m. | L 0-4 | |
| Mon., 5/10 | V Baseball | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | L 0-14 | |
| Mon., 5/10 | V Boys Golf | Litchfield | Home - Green woods Country Club [Directions] | 3:00 p.m. | Gilbert- 237 Litchfield- 190 (Gilbert 4-5 League Record) | |
| Mon., 5/10 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/11 | V Boys Golf | Nonnewaug | Away - Stonybrook Golf Course [Directions] | 3:00 p.m. | Gilbert- 249 Nonnewaug-207 (Gilbert 4-6 League Record) | |
| Tue., 5/11 | V Boys Outdoor Track | Wamogo | Away - Wamogo Regional HS-Plumb Hill Field [Directions] | 3:45 p.m. | ||
| Tue., 5/11 | V Girls Outdoor Track | Wamogo | Away - Wamogo Regional HS-Plumb Hill Field [Directions] | 3:45 p.m. | ||
| Tue., 5/11 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | L 0-16 | |
| Tue., 5/11 | V Girls Tennis | Housatonic Regional | Home - Gilbert School-Tennis Courts [Directions] | 3:30 p.m. | L 0-4 | |
| Wed., 5/12 | V Baseball | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 11-1 | |
| Wed., 5/12 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | 4:00 p.m. | L 2-7 | |
| Wed., 5/12 | V Girls Tennis | Nonnewaug | Home - Gilbert School-Tennis Courts [Directions] | 3:30 p.m. | L 0-4 | |
| Thu., 5/13 | V Boys Outdoor Track | Terryville | Away - Terryville HS-Track [Directions] | 3:45 p.m. | ||
| Thu., 5/13 | V Girls Outdoor Track | Terryville | Away - Terryville HS-Track [Directions] | 3:45 p.m. | ||
| Thu., 5/13 | JV Softball | Housatonic Regional | Home - Winsted Rowley Field [Directions] | 3:30 p.m. | ||
| Fri., 5/14 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | L 11-1 | Early release at 2:00 pm. |
| Fri., 5/14 | V Softball | Nonnewaug | Home - Walker Field-Rowley Field [Directions] | 3:45 p.m. | L 1-19 | |
| Fri., 5/14 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 5/15 | JV Softball | Nonnewaug | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | 9:30 a.m. | ||
| Mon., 5/17 | V Baseball | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | W 11-1 | |
| Mon., 5/17 | V Boys Golf | Housatonic Regional, Shepaug Valley | Away - Canaan Country Club [Directions] | 3:00 p.m. | Gilbert- 200 Housatonic- 185 Shepaug- 231 (Gilbert 5-7 League Record) | |
| Mon., 5/17 | V Girls Tennis | Thomaston | Home - Gilbert School-Tennis Courts [Directions] | 4:45 p.m. | L 0-7 | |
| Tue., 5/18 | V Boys Outdoor Track | Thomaston, Wamogo | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Girls Outdoor Track | Thomaston, Wamogo | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Varsity Softball Field [Directions] | 3:45 p.m. | L 3-20 | |
| Wed., 5/19 | V Baseball | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | L 13-3 | |
| Wed., 5/19 | V Boys Golf | Nonnewaug, Northwestern | Home - Green woods Country Club [Directions] | 3:00 p.m. | Gilbert- 216 Northwestern- 226 Nonnewaug- 200 (Gilbert 6-8 FINAL League Record) | |
| Wed., 5/19 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | 4:00 p.m. | L 1-23 | |
| Fri., 5/21 | V Baseball | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 18-0 (5) | |
| Sat., 5/22 | V Boys Outdoor Track | Boys BL Track Championships @ Nystrom Park | Away - Thomaston Nystrom Park-Nystroms Park Track | 2:00 p.m. | ||
| Sat., 5/22 | V Girls Outdoor Track | Girls BL Track Championships @ Nystrom Park | Away - Thomaston Nystrom Park-Nystroms Park Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:30 a.m. | ||||||
| Mon., 5/24 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 4:15 p.m. | L 14-3 (5) | |
| Mon., 5/24 | V Boys Golf | Terryville | Away - Pequabuck Golf Club-Golf Course, Front 9 [Directions] | 3:00 p.m. | Terryville/Thomaston- 212 Gilbert-236 | |
| Mon., 5/24 | V Softball | Shepaug Valley | Home - Walker Field-Rowley Field [Directions] | 3:45 p.m. | L 8-18 | |
| Tue., 5/25 | V Softball | Lewis Mills | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | L 3-18 | |
| Wed., 5/26 | V Baseball | Canton | Away - Bowdoin Field-Baseball Diamond [Directions] | 3:45 p.m. | L 11-1 (5) | |
| Tue., 6/1 | V Boys Golf | BL Golf All Star Tournament | Away - Fairfiew Farm Golf Course | 8:00 a.m. | ||