| Housatonic Regional 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 513 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Litchfield | Away - Community Field [Directions] | TBA | ||
| TBA | JV Baseball | Litchfield | Home - High School Field [Directions] | TBA | ||
| TBA | JV Girls Basketball | Litchfield | Home - HVRHS. Gymnasium [Directions] | TBA | ||
| Fri., 8/23 | V Football | Watertown (Scrim.) | Away - John J. Mills Complex @ Watertown High School [Directions] | 5:00 p.m. | ||
| Sat., 8/24 | V Football | Northwest United (Scrim.) | Home - High School Field [Directions] | 10:00 a.m. | ||
| Tue., 8/27 | V Girls Soccer | Torrington (Scrim.) | Away - Torrington High School [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | V Football | Simsbury (Scrim.) | Away - Simsbury HS [Directions] | 4:00 p.m. | ||
| Thu., 8/29 | V Boys Soccer | Mt. Everett (MA) (Scrim.) | Home - High School Field [Directions] | 4:00 p.m. | Varsity Only | |
| Thu., 8/29 | V Girls Soccer | Holy Cross (Scrim.) | Away - HCHS [Directions] | 4:00 p.m. | ||
| Sat., 8/31 | V Football | Monument Mountain (MA) (Scrim.) | Home - High School Field [Directions] | 10:00 a.m. | ||
| Sat., 8/31 | V Football | St. Paul Catholic (Scrim.) | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Thu., 9/5 | V Boys Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:15 p.m. | ||
| Thu., 9/5 | V Boys Soccer | Torrington (Scrim.) | Home - High School Field [Directions] | 3:30 p.m. | ||
| Thu., 9/5 | JV Boys Soccer | Torrington (Scrim.) | Home - High School Field [Directions] | 3:30 p.m. | ||
| Thu., 9/5 | V Girls Cross Country | BL Scrimmage | Away - Black Rock State Park | 3:30 p.m. | ||
| Fri., 9/6 | V Football | Nonnewaug (Scrim.) | Away - Nonnewaug H.S. Football Field [Directions] | 4:00 p.m. | ||
| Fri., 9/6 | V Girls Volleyball | Canton (Scrim.) | Away - Canton H.S. [Directions] | 5:30 p.m. | ||
| Sat., 9/7 | V Football | Bullard/Kolbe (Scrim.) | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Sat., 9/7 | V Boys Soccer | Webutuck High School | Away - Webutuck H.S. | 10:00 a.m. | ||
| Sat., 9/7 | JV Boys Soccer | Webutuck High School | Away - Webutuck H.S. | 10:00 a.m. | ||
| Sat., 9/7 | V Girls Soccer | Kent School (Scrim.) | Home - High School Field [Directions] | 2:00 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Gilbert, Northwestern | Home - High School CC Course [Directions] | 4:15 p.m. | H-G 28-27 | |
| Tue., 9/10 | V Girls Cross Country | Gilbert, Northwestern | Home - High School CC Course [Directions] | 4:15 p.m. | H-G 15-50 | |
| Tue., 9/10 | V Field Hockey | Nonnewaug | Home - High School Field [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 9/10 | JV Field Hockey | Nonnewaug | Home - High School Field [Directions] | 5:00 p.m. | L 0-1 | |
| Wed., 9/11 | V Boys Soccer | Nonnewaug | Away - Nonnewaug High School [Directions] | 3:45 p.m. | L 0-3 | |
| Wed., 9/11 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug High School [Directions] | 3:45 p.m. | ||
| Thu., 9/12 | V Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | 3:30 p.m. | W 34-27 | |
| Thu., 9/12 | V Football | Old Saybrook | Away - Old Saybrook High School [Directions] | 4:45 p.m. | L 7-37 | |
| Thu., 9/12 | V Girls Soccer | Nonnewaug | Home - High School Field [Directions] | 3:45 p.m. | L 0-1 | |
| Thu., 9/12 | JV Girls Soccer | Nonnewaug | Home - High School Field [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-2 | |
| Fri., 9/13 | JV Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 9/13 | JV Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 5:00 p.m. | L 0-1 | |
| Fri., 9/13 | V Girls Volleyball | Terryville | Away - New Terryville High School [Directions] | 5:15 p.m. | L 1-3 | |
| Fri., 9/13 | JV Girls Volleyball | Terryville | Away - New Terryville High School [Directions] | 4:00 p.m. | ||
| Sat., 9/14 | V Girls Soccer | Gilbert | Home - High School Field [Directions] | 10:00 a.m. | W 7-1 | |
| Mon., 9/16 | JV Football | Cromwell/Portland | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Boys Cross Country | Wamogo, Thomaston, Nonnewaug | Away - Nonnewaug HS XC Course [Directions] | 4:00 p.m. | H-N 44-15 H-T 49-15 | |
| Tue., 9/17 | V Boys Soccer | Thomaston | Home - High School Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 9/17 | V Girls Cross Country | Wamogo, Thomaston, Nonnewaug | Away - Nonnewaug HS XC Course [Directions] | 4:00 p.m. | H-N 38-17 H-T 45-16 | |
| Tue., 9/17 | V Field Hockey | Litchfield | Home - High School Field [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 9/17 | JV Field Hockey | Litchfield | Home - High School Field [Directions] | 5:00 p.m. | L 0-2 | |
| Tue., 9/17 | V Girls Volleyball | Northwestern | Home - HVRHS. Gymnasium [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 9/17 | JV Girls Volleyball | Northwestern | Home - HVRHS. Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Lewis Mills | Home - High School Field [Directions] | 3:45 p.m. | L 2-9 | |
| Fri., 9/20 | V Boys Soccer | Shepaug Valley | Home - High School Field [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 9/20 | JV Boys Soccer | Shepaug Valley | Home - High School Field [Directions] | 3:45 p.m. | ||
| Fri., 9/20 | V Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | 3:45 p.m. | L 0-3 | |
| Fri., 9/20 | JV Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | 5:00 p.m. | Cancelled | |
| Fri., 9/20 | V Girls Volleyball | Gilbert | Away - Gilbert Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Fri., 9/20 | JV Girls Volleyball | Gilbert | Away - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | V Football | MSW | Home - High School Field [Directions] | 1:00 p.m. | L 8-48 | |
| Sat., 9/21 | V Football | Granby/Canton | Home - Gilbert [Directions] | 1:00 p.m. | W 48-21 | Homecoming |
| Sat., 9/21 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 6:30 p.m. | L 0-1 | |
| Sat., 9/21 | JV Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | JV Football | Granby/Canton | Away - Ahrens Park Field [Directions] | 3:45 p.m. | ||
| Mon., 9/23 | JV Football | Canton | Home - Gilbert [Directions] | 3:45 p.m. | Cancelled | |
| Mon., 9/23 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 9/23 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Mon., 9/23 | V Girls Volleyball | Mt. Everett (MA) | Home - HVRHS. Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 9/23 | JV Girls Volleyball | Mt. Everett (MA) | Home - HVRHS. Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Thomaston, Litchfield, Shepaug Valley | Away - Black Rock State Park [Directions] | 4:15 p.m. | ||
| Tue., 9/24 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 9/24 | JV Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Thomaston, Litchfield, Shepaug Valley | Away - Black Rock State Park [Directions] | 4:15 p.m. | H-L 39-20 H-S 24-35 | |
| Tue., 9/24 | V Field Hockey | Northwestern | Home - High School Field [Directions] | 3:45 p.m. | L 1-0 | |
| Tue., 9/24 | JV Field Hockey | Northwestern | Home - High School Field [Directions] | 5:00 p.m. | L 0-2 | |
| Thu., 9/26 | V Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 1-0 | |
| Thu., 9/26 | JV Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | ||
| Thu., 9/26 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:45 p.m. | L 0-3 | |
| Thu., 9/26 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/27 | V Boys Cross Country | Wamogo | Away - White Memorial (HS XC Course) [Directions] | 4:15 p.m. | H-W 31-26 | |
| Fri., 9/27 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | 6:30 p.m. | L 25-42 | |
| Fri., 9/27 | V Boys Soccer | Lewis Mills | Home - High School Field [Directions] | 3:45 p.m. | L 1-2 | |
| Fri., 9/27 | JV Boys Soccer | Lewis Mills | Home - High School Field [Directions] | 3:45 p.m. | ||
| Fri., 9/27 | V Girls Cross Country | Wamogo | Away - White Memorial (HS XC Course) [Directions] | 4:15 p.m. | H-W 21-40 | |
| Fri., 9/27 | V Field Hockey | Wamogo | Home - High School Field [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 9/27 | JV Field Hockey | Wamogo | Home - High School Field [Directions] | 5:00 p.m. | T 1-1 | |
| Sat., 9/28 | V Football | Canton | Away - Canton H.S. [Directions] | 1:30 p.m. | L 6-47 | |
| Sat., 9/28 | JV Football | North Branford | Home - Gilbert [Directions] | 11:00 a.m. | ||
| Mon., 9/30 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:45 p.m. | W 3-1 | |
| Mon., 9/30 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:15 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Terryville, Lewis Mills | Home - High School CC Course [Directions] | 4:15 p.m. | H-L 46-15 H-T 36-22 L-T 19-36 | |
| Tue., 10/1 | V Boys Soccer | Terryville | Away - High School Field [Directions] | 3:45 p.m. | L 2-1 | |
| Tue., 10/1 | JV Boys Soccer | Terryville | Away - High School Field [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Terryville, Lewis Mills | Home - High School CC Course [Directions] | 4:15 p.m. | H-L 32-24 H-T 19-40 L-T 17-44 | |
| Tue., 10/1 | V Field Hockey | Shepaug Valley | Away - Joan Gauthey Field [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 10/1 | JV Field Hockey | Shepaug Valley | Away - Joan Gauthey Field [Directions] | 5:00 p.m. | L 0-1 | |
| Tue., 10/1 | V Girls Soccer | Shepaug Valley | Home - High School Field [Directions] | 3:45 p.m. | L 2-7 | |
| Tue., 10/1 | JV Girls Soccer | Shepaug Valley | Home - High School JV Field [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Volleyball | Canton | Home - HVRHS. Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/1 | JV Girls Volleyball | Canton | Home - HVRHS. Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 10/3 | V Field Hockey | Nonnewaug | Away - Nonnewaug High School [Directions] | 3:45 p.m. | L 0-6 | |
| Thu., 10/3 | JV Field Hockey | Nonnewaug | Away - Nonnewaug High School [Directions] | 5:00 p.m. | ||
| Thu., 10/3 | V Girls Soccer | Terryville | Home - High School Field [Directions] | 3:45 p.m. | W 6-2 | |
| Thu., 10/3 | JV Girls Soccer | Terryville | Home - High School JV Field [Directions] | 3:45 p.m. | ||
| Fri., 10/4 | V Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | 7:30 p.m. | T 1-1 | |
| Fri., 10/4 | JV Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | 4:45 p.m. | ||
| Fri., 10/4 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug High School Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 10/4 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug High School Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | V Football | Lewis Mills | Home - Gilbert [Directions] | 2:30 p.m. | W 44-12 | |
| Mon., 10/7 | JV Girls Soccer | Gilbert | Away - High School Field [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Northwestern | Away - Northwestern [Directions] | 4:15 p.m. | H-NW 15-48 | |
| Tue., 10/8 | JV Football | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 10/8 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | Northwestern | Away - Northwestern [Directions] | 4:15 p.m. | H-NW 19-38 | |
| Tue., 10/8 | V Field Hockey | Lewis Mills | Home - High School Field [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 10/8 | JV Field Hockey | Lewis Mills | Home - High School Field [Directions] | 5:00 p.m. | ||
| Tue., 10/8 | V Girls Volleyball | Terryville | Home - HVRHS. Gymnasium [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 10/8 | JV Girls Volleyball | Terryville | Home - HVRHS. Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | V Girls Soccer | Nonnewaug | Away - Nonnewaug High School [Directions] | 3:45 p.m. | L 2-4 | |
| Wed., 10/9 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | 3:45 p.m. | ||
| Thu., 10/10 | V Boys Soccer | Nonnewaug | Home - High School Field [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 10/10 | JV Boys Soccer | Nonnewaug | Home - High School Field [Directions] | 3:45 p.m. | ||
| Thu., 10/10 | V Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Thu., 10/10 | JV Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Boys Cross Country | Nonnewaug Invitational | Away - Nonnewaug High School | 4:15 p.m. | ||
| Fri., 10/11 | V Football | Stafford/East Windsor/Somers | Home - High School Field [Directions] | 6:30 p.m. | L 8-30 | |
| Fri., 10/11 | V Girls Cross Country | Nonnewaug Invitational | Away - Nonnewaug High School | 4:15 p.m. | ||
| Fri., 10/11 | V Girls Volleyball | Amistad | Home - HVRHS. Gymnasium [Directions] | 5:45 p.m. | W 3-1 | |
| Fri., 10/11 | JV Girls Volleyball | Amistad | Home - HVRHS. Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/12 | V Football | Ellington | Away - Ellington High School [Directions] | 1:30 p.m. | W 20-14 (OT) | |
| Mon., 10/14 | JV Football | Ellington | Home - Gilbert [Directions] | 11:00 a.m. | ||
| Tue., 10/15 | V Boys Soccer | Wamogo | Home - High School Field [Directions] | 6:30 p.m. | W 4-2 | |
| Tue., 10/15 | JV Boys Soccer | Wamogo | Home - High School Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | W 3-1 | |
| Tue., 10/15 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | 5:00 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Gilbert | Home - HVRHS. Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/15 | JV Girls Volleyball | Gilbert | Home - HVRHS. Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Volleyball | Monument Mountain (MA) | Away - Monument Mountain H.S. (MA) | 5:30 p.m. | W 3-1 | |
| Wed., 10/16 | JV Girls Volleyball | Monument Mountain (MA) | Away - Monument Mountain H.S. (MA) | 4:00 p.m. | ||
| Thu., 10/17 | V Girls Soccer | Lewis Mills | Away - Lewis Mills Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-6 | |
| Thu., 10/17 | JV Girls Soccer | Lewis Mills | Away - Lewis Mills JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | V Boys Cross Country | BL Championships | Away - Black Rock State Park | 4:15 p.m. | ||
| Fri., 10/18 | V Boys Soccer | Thomaston | Away - Highwood Farms [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/18 | JV Boys Soccer | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | V Girls Cross Country | BL Championships | Away - Black Rock State Park | 4:15 p.m. | ||
| Fri., 10/18 | V Field Hockey | Thomaston | Home - High School Field [Directions] | 3:45 p.m. | L 1-4 | |
| Fri., 10/18 | JV Field Hockey | Thomaston | Home - High School Field [Directions] | 5:00 p.m. | ||
| Fri., 10/18 | V Girls Volleyball | Mt. Everett (MA) | Away - Mt. Everett High School (MA) | 5:15 p.m. | W 3-0 | |
| Fri., 10/18 | JV Girls Volleyball | Mt. Everett (MA) | Away - Mt. Everett H.S. | 3:45 p.m. | ||
| Sat., 10/19 | V Football | Avon | Home - High School Field [Directions] | 2:30 p.m. | L 6-41 | |
| Sat., 10/19 | V Girls Soccer | Wamogo | Home - High School Field [Directions] | 3:45 p.m. | W 3-1 | |
| Sat., 10/19 | JV Girls Soccer | Wamogo | Home - High School JV Field [Directions] | 3:45 p.m. | ||
| Mon., 10/21 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-2 | |
| Mon., 10/21 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 10/22 | V Field Hockey | Northwestern | Away - Northwestern HS [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/22 | JV Field Hockey | Northwestern | Away - Northwestern HS [Directions] | 5:00 p.m. | W 1-0 | |
| Tue., 10/22 | V Girls Soccer | Litchfield | Home - High School Field [Directions] | 6:30 p.m. | L 2-3 | |
| Tue., 10/22 | JV Girls Soccer | Litchfield | Home - High School JV Field [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Girls Volleyball | Lewis Mills | Home - HVRHS. Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/22 | JV Girls Volleyball | Lewis Mills | Home - HVRHS. Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Northwestern | Home - High School Field [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 10/24 | JV Girls Soccer | Northwestern | Home - High School JV Field [Directions] | 3:45 p.m. | ||
| Thu., 10/24 | V Girls Volleyball | Amistad | Away - Elm City Elementary School [Directions] | 6:15 p.m. | W 3-1 | |
| Thu., 10/24 | JV Girls Volleyball | Amistad | Away - Elm City Elementary School [Directions] | 5:15 p.m. | ||
| Fri., 10/25 | V Boys Soccer | Gilbert | Home - High School Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 10/25 | JV Boys Soccer | Gilbert | Home - High School Field [Directions] | 3:45 p.m. | ||
| Fri., 10/25 | V Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 10/25 | JV Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | W 2-1 | |
| Sat., 10/26 | V Boys Cross Country | CIAC State Championship Meet | Away - TBA | TBA | ||
| Sat., 10/26 | V Football | Canton | Away - Canton H.S. [Directions] | 1:00 p.m. | W 28-15 | |
| Sat., 10/26 | V Football | Lewis Mills | Away - Muzzy Field - Bristol [Directions] | 2:00 p.m. | L Forfeit | |
| Sat., 10/26 | V Girls Cross Country | CIAC State Championship Meet | Away - TBA | TBA | ||
| Mon., 10/28 | JV Football | Taft | Away - Taft School - Watertown | 3:45 p.m. | Cancelled | |
| Mon., 10/28 | JV Football | Lewis Mills | Home - High School Field [Directions] | 4:00 p.m. | Cancelled | |
| Mon., 10/28 | V Boys Soccer | Northwestern | Home - High School Field [Directions] | 3:45 p.m. | W 2-0 | |
| Mon., 10/28 | JV Boys Soccer | Northwestern | Home - High School Field [Directions] | 3:45 p.m. | ||
| Mon., 10/28 | V Field Hockey | Shepaug Valley | Home - High School Field [Directions] | 3:45 p.m. | L 0-2 | |
| Mon., 10/28 | JV Field Hockey | Shepaug Valley | Home - High School Field [Directions] | 5:00 p.m. | ||
| Mon., 10/28 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | W 2-0 | |
| Mon., 10/28 | JV Girls Soccer | Shepaug Valley | Away - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/29 | V Girls Volleyball | Nonnewaug | Home - HVRHS. Gymnasium [Directions] | 5:15 p.m. | W 3-2 | |
| Tue., 10/29 | JV Girls Volleyball | Nonnewaug | Home - HVRHS. Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/30 | V Boys Soccer | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | T 0-0 | |
| Wed., 10/30 | JV Boys Soccer | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | ||
| Wed., 10/30 | V Girls Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | W 4-2 | |
| Wed., 10/30 | JV Girls Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | ||
| Thu., 10/31 | JV Girls Soccer | Lewis Mills | Home - High School JV Field [Directions] | 3:45 p.m. | ||
| Sat., 11/2 | V Football | Coginchaug/Hale Ray/East Hampton | Home - High School Field [Directions] | 2:00 p.m. | L Forfeit | |
| Sat., 11/2 | V Football | Avon | Home - Gilbert [Directions] | 2:30 p.m. | W 34-33 | |
| Mon., 11/4 | JV Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional High School [Directions] | 3:00 p.m. | Cancelled | |
| Mon., 11/4 | JV Football | Avon | Away - Avon High School [Directions] | 3:45 p.m. | ||
| Sat., 11/9 | V Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks High School [Directions] | 1:00 p.m. | L Forfeit | |
| Sat., 11/9 | V Football | Enfield | Home - Gilbert [Directions] | 1:00 p.m. | W 34-13 | |
| Sat., 11/9 | JV Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks High School [Directions] | 11:00 a.m. | Cancelled | |
| Mon., 11/11 | JV Football | Enfield | Away - Enfield High Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 11/16 | V Football | Nonnewaug | Away - Nonnewaug High School Football Field [Directions] | 1:00 p.m. | W 27-7 | |
| Sat., 11/16 | V Football | Granby/Canton | Away - Granby Memorial High School [Directions] | 6:00 p.m. | L Forfeit | |
| Mon., 11/18 | JV Football | Nonnewaug | Home - Gilbert [Directions] | 3:00 p.m. | ||
| Fri., 11/22 | V Football | Valley Regional/Old Lyme | Away - Valley Regional High School [Directions] | 6:30 p.m. | L 0-35 | |
| Sat., 11/23 | V Football | Nonnewaug | Home - High School Field [Directions] | 1:00 p.m. | L Forfeit | |
| Sat., 11/23 | JV Football | Valley Regional/Old Lyme | Home - Gilbert [Directions] | 10:30 a.m. | Cancelled | |
| Sat., 11/23 | JV Football | Nonnewaug | Home - Housatonic Field [Directions] | 1:00 p.m. | ||
| Thu., 11/28 | V Football | Gilbert/Northwestern/Housy | Away - Gilbert [Directions] | 10:00 a.m. | L 22-27 | |
| Thu., 11/28 | V Football | Housatonic Regional | Home - Gilbert [Directions] | 10:00 a.m. | W 27-22 | |
| Tue., 12/3 | V Girls Basketball | Pine Plains (NY) (Scrim.) | Away - Pine Plains High School | 5:30 p.m. | ||
| Tue., 12/3 | JV Girls Basketball | Pine Plains (NY) (Scrim.) | Away - Stissing Mtn High School | 4:30 p.m. | ||
| Thu., 12/5 | V Girls Basketball | Torrington (Scrim.) | Home - HVRHS. Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/11 | V Boys Basketball | Tournament Game - Opponent Not Known (Scrim.) | Home - HVRHS. Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 12/11 | V Boys Ice Hockey | Shepaug Jamboree | Away - The Gunnery Hockey Rink | 7:00 p.m. | ||
| Wed., 12/11 | V Girls Basketball | Gilbert | Away - Gilbert Gym [Directions] | 7:00 p.m. | W 67-24 | |
| Wed., 12/11 | JV Girls Basketball | Gilbert | Away - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/13 | V Boys Basketball | Brookfield (Scrim.) | Home - HVRHS. Gymnasium [Directions] | 4:15 p.m. | ||
| Fri., 12/13 | JV Boys Basketball | Brookfield (Scrim.) | Home - HVRHS. Gymnasium [Directions] | 4:15 p.m. | ||
| Mon., 12/16 | V Boys Basketball | Wolcott Tech (Scrim.) | Home - HVRHS. Gymnasium [Directions] | 6:15 p.m. | ||
| Mon., 12/16 | JV Boys Basketball | Wolcott Tech (Scrim.) | Home - HVRHS. Gymnasium [Directions] | 5:00 p.m. | ||
| Mon., 12/16 | V Girls Basketball | Litchfield | Away - Litchfield High School [Directions] | 7:00 p.m. | W 63-32 | |
| Wed., 12/18 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | W 55-39 | |
| Wed., 12/18 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/18 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena [Directions] | 7:40 p.m. | W 4-1 | |
| Wed., 12/18 | V Boys Swimming and Diving | Gilbert | Home - Hotchkiss Pool [Directions] | 4:00 p.m. | Warm up at 3:30pm | |
| Wed., 12/18 | V Wrestling | Northwestern | Away - Northwestern Gym [Directions] | 6:30 p.m. | Housy over northwestern 36-27 | |
| Thu., 12/19 | V Girls Basketball | Thomaston | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 36-46 | |
| Thu., 12/19 | JV Girls Basketball | Thomaston | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | V Boys Basketball | Terryville | Away - New Terryville High School [Directions] | 7:00 p.m. | L 39-83 | |
| Fri., 12/20 | JV Boys Basketball | Terryville | Away - New Terryville High School [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | V Boys Ice Hockey | Lyman Hall | Home - Hotchkiss [Directions] | 8:00 p.m. | W 4-2 | |
| Fri., 12/20 | V Girls Basketball | Terryville | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 70-38 | |
| Fri., 12/20 | JV Girls Basketball | Terryville | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 12/21 | V Wrestling | Derby Invitational | Away - Derby High School | 10:00 a.m. | ||
| Mon., 12/23 | V Boys Basketball | Mt. Everett (MA) | Home - HVRHS. Gymnasium [Directions] | 4:30 p.m. | L 60-70 | |
| Mon., 12/23 | JV Boys Basketball | Mt. Everett (MA) | Home - HVRHS. Gymnasium [Directions] | 3:00 p.m. | ||
| Mon., 12/23 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | 4:00 p.m. | W 4-2 | |
| Fri., 12/27 | JV Girls Basketball | Pine Plains Holiday Tournament | Away - Stissing Mountain High School | 1:00 p.m. | ||
| Sat., 12/28 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | 3:00 p.m. | W 5-2 | |
| Sat., 12/28 | V Wrestling | Mounument Mountain Holiday Tournament | Away - Mounument Mountain | 10:00 a.m. | ||
| Sat., 12/28 | JV Girls Basketball | Pine Plains Holiday Tournament | Away - Stissing Mountain High School | 1:00 p.m. | ||
| Mon., 12/30 | V Boys Basketball | Nonnewaug | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 48-70 | |
| Mon., 12/30 | JV Boys Basketball | Nonnewaug | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/30 | V Boys Ice Hockey | Mt. Everett (MA) | Home - Hotchkiss [Directions] | 7:30 p.m. | W 5-0 | |
| Mon., 12/30 | V Wrestling | Seymour, St. Paul Catholic | Home - Housatonic [Directions] | 11:00 a.m. | St. Paul over housy 36-28 Seymor over housy 66-18 | |
| Mon., 12/30 | V Girls Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 7:00 p.m. | L 35-43 | |
| Mon., 12/30 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/4 | V Boys Ice Hockey | Sheehan | Home - Hotchkiss [Directions] | 2:00 p.m. | L 3-5 | |
| Sat., 1/4 | V Girls Basketball | Gilbert | Home - HVRHS. Gymnasium [Directions] | 5:00 p.m. | W 68-28 | |
| Sat., 1/4 | JV Girls Basketball | Gilbert | Home - HVRHS. Gymnasium [Directions] | 3:00 p.m. | ||
| Tue., 1/7 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:00 p.m. | L 44-69 | |
| Tue., 1/7 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/7 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:00 p.m. | Warm up at 6:30pm | |
| Tue., 1/7 | V Girls Basketball | Northwestern | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 47-34 | |
| Tue., 1/7 | JV Girls Basketball | Northwestern | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/8 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Hotchkiss [Directions] | 7:15 p.m. | W 2-0 | |
| Wed., 1/8 | V Boys Swimming and Diving | Lewis Mills | Home - Hotchkiss Pool [Directions] | 4:30 p.m. | Warm up 4:30pm | |
| Wed., 1/8 | V Co-ed Alpine Skiing | Tournament Game - Opponent Not Known | Away - Catamount | 3:00 p.m. | ||
| Fri., 1/10 | V Boys Basketball | Wamogo | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 63-51 | |
| Fri., 1/10 | JV Boys Basketball | Wamogo | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Wamogo | Home - HVRHS. Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/10 | V Boys Ice Hockey | JBWA | Home - Hotchkiss [Directions] | 8:30 p.m. | W 2-1 | |
| Fri., 1/10 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 7:30 p.m. | Warm up at 7:00pm | |
| Fri., 1/10 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | W 50-30 | |
| Fri., 1/10 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Sat., 1/11 | V Wrestling | Mt. Everett (MA) | Away - Mt Everett | 10:00 a.m. | Mount everett over housy 54-16 | |
| Tue., 1/14 | V Boys Basketball | Shepaug Valley | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 70-51 | |
| Tue., 1/14 | JV Boys Basketball | Shepaug Valley | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/14 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 66-37 | |
| Tue., 1/14 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | 7:00 p.m. | T 2-2 (OT) | |
| Wed., 1/15 | V Wrestling | Terryville-Thomaston | Home - Housatonic [Directions] | 6:30 p.m. | Terryville over housy 60-24 | |
| Wed., 1/15 | V Co-ed Alpine Skiing | Tournament Game - Opponent Not Known | Away - Butternut | 3:00 p.m. | ||
| Fri., 1/17 | V Boys Basketball | Lewis Mills | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 52-56 | |
| Fri., 1/17 | JV Boys Basketball | Lewis Mills | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Lewis Mills | Home - HVRHS. Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/17 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | L 41-49 | |
| Fri., 1/17 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/18 | V Wrestling | New Milford Tournament | Away - New Milford High School | 9:30 a.m. | ||
| Mon., 1/20 | V Boys Ice Hockey | Norwalk | Home - Hotchkiss [Directions] | 12:30 p.m. | W 3-1 | |
| Wed., 1/22 | V Boys Ice Hockey | Rocky Hill Coop | Away - Champions Rink [Directions] | 8:00 p.m. | W 5-3 | |
| Wed., 1/22 | V Co-ed Alpine Skiing | Tournament Game - Opponent Not Known | Away - Butternut | 3:00 p.m. | ||
| Thu., 1/23 | V Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 7:00 p.m. | L 43-63 | |
| Thu., 1/23 | JV Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/23 | FR Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/23 | V Wrestling | Gilbert/Torrington | Home - Housatonic [Directions] | 6:30 p.m. | Housy over gilbert 26-24 | |
| Thu., 1/23 | V Girls Basketball | Ellington | Away - Ellington High School [Directions] | 6:30 p.m. | L 33-53 | |
| Thu., 1/23 | JV Girls Basketball | Ellington | Away - Ellington High School [Directions] | 5:00 p.m. | ||
| Fri., 1/24 | V Boys Ice Hockey | New Fairfield | Home - Hotchkiss [Directions] | 8:30 p.m. | T 1-1 (OT) | |
| Fri., 1/24 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 7:30 p.m. | Warm up at 7:00 | |
| Mon., 1/27 | V Girls Basketball | Mt. Everett (MA) | Away - Mt Everett Gym | 7:00 p.m. | W 47-36 | |
| Mon., 1/27 | JV Girls Basketball | Mt. Everett (MA) | Away - HVRHS. Gymnasium | 5:30 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Pine Plains (NY) | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 59-45 | |
| Tue., 1/28 | JV Boys Basketball | Pine Plains (NY) | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | V Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 7:00 p.m. | L 50-76 | |
| Wed., 1/29 | JV Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | FR Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 3:45 p.m. | ||
| Wed., 1/29 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | L 1-5 | |
| Wed., 1/29 | V Boys Swimming and Diving | Litchfield | Home - Hotchkiss Pool [Directions] | 5:00 p.m. | Warm up at 4:30pm | |
| Wed., 1/29 | V Wrestling | Holy Cross | Away - Holy Cross HS [Directions] | 6:30 p.m. | ||
| Wed., 1/29 | V Co-ed Alpine Skiing | Tournament Game - Opponent Not Known | Away - Mohawk | 3:00 p.m. | ||
| Wed., 1/29 | V Girls Basketball | Litchfield | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 56-34 | |
| Wed., 1/29 | JV Girls Basketball | Litchfield | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/31 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 62-57 | |
| Fri., 1/31 | JV Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Shepaug Valley | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 48-23 | |
| Fri., 1/31 | JV Girls Basketball | Shepaug Valley | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/1 | V Wrestling | Jonathan Law Tournament | Away - Jonathan Law | TBA | ||
| Tue., 2/4 | V Boys Basketball | Northwestern | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 52-94 | |
| Tue., 2/4 | JV Boys Basketball | Northwestern | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/4 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | Warm up at 4:00pm | |
| Tue., 2/4 | V Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:00 p.m. | L 26-41 | |
| Tue., 2/4 | JV Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/5 | V Co-ed Alpine Skiing | Tournament Game - Opponent Not Known | Away - Mohawk Mountain | 3:00 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Terryville | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 44-83 | |
| Fri., 2/7 | JV Boys Basketball | Terryville | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/7 | V Boys Ice Hockey | Rocky Hill Coop | Home - Hotchkiss [Directions] | 8:30 p.m. | W 5-0 | |
| Fri., 2/7 | V Wrestling | Nonnewaug | Away - Nonnewaug High School Mat Room [Directions] | 5:00 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Terryville | Away - New Terryville High School [Directions] | 7:00 p.m. | W 60-36 | |
| Fri., 2/7 | JV Girls Basketball | Terryville | Away - New Terryville High School [Directions] | 5:30 p.m. | ||
| Mon., 2/10 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School | 6:30 p.m. | W 4-2 | |
| Mon., 2/10 | V Boys Swimming and Diving | Northwestern | Home - Hotchkiss Pool [Directions] | 6:30 p.m. | Warm up at 6:00pm | |
| Mon., 2/10 | V Wrestling | Portland/Cromwell | Away - Portland High School [Directions] | 6:00 p.m. | ||
| Tue., 2/11 | V Boys Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 7:00 p.m. | L 61-65 (OT) | |
| Tue., 2/11 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/11 | V Girls Basketball | Nonnewaug | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 27-41 | |
| Tue., 2/11 | JV Girls Basketball | Nonnewaug | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/12 | V Boys Swimming and Diving | Shepaug Valley | Home - Hotchkiss Pool [Directions] | 5:00 p.m. | Warm up at 4:30pm | |
| Wed., 2/12 | V Wrestling | Wolcott Tech | Home - High School Cafeteria [Directions] | 6:30 p.m. | ||
| Mon., 2/17 | V Girls Basketball | Wamogo | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 62-19 | |
| Mon., 2/17 | JV Girls Basketball | Wamogo | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/19 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavillion [Directions] | 6:00 p.m. | L 3-2 | |
| Wed., 2/19 | V Co-ed Alpine Skiing | Championship | Away - TBA | 3:00 p.m. | ||
| Wed., 2/19 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | L 33-71 | |
| Wed., 2/19 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/20 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | L 43-55 | |
| Thu., 2/20 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Thu., 2/20 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 3:45 p.m. | ||
| Thu., 2/20 | V Boys Swimming and Diving | Litchfield | Away - CJR Pool [Directions] | 3:30 p.m. | Warm up at 3:00PM | |
| Thu., 2/20 | V Girls Basketball | Lewis Mills | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 49-38 | |
| Thu., 2/20 | JV Girls Basketball | Lewis Mills | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/21 | V Boys Basketball | Thomaston | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 49-46 | |
| Fri., 2/21 | JV Boys Basketball | Thomaston | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/24 | V Boys Basketball | Gilbert | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 50-65 | |
| Mon., 2/24 | JV Boys Basketball | Gilbert | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/24 | FR Boys Basketball | Gilbert | Home - HVRHS. Gymnasium [Directions] | 3:45 p.m. | Cancelled | |
| Mon., 2/24 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - Gunnery Rink [Directions] | 8:00 p.m. | W 1-0 | |
| Wed., 2/26 | V Boys Basketball | Litchfield | Home - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 39-51 | |
| Wed., 2/26 | JV Boys Basketball | Litchfield | Home - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/26 | FR Boys Basketball | Litchfield | Home - HVRHS. Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 2/26 | V Boys Swimming and Diving | Wamogo | Home - Hotchkiss Pool [Directions] | 5:00 p.m. | Warm up 4:30PM | |
| Thu., 2/27 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | L 37-75 | |
| Thu., 2/27 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/27 | FR Boys Basketball | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | ||
| Thu., 2/27 | V Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | 6:00 p.m. | W 3-2 (OT) | |
| Fri., 2/28 | V Boys Ice Hockey | Masuk | Home - Hotchkiss [Directions] | 8:30 p.m. | L 1-4 | |
| Sun., 3/2 | V Boys Ice Hockey | Hall | Away - Kingswood Oxford [Directions] | 12:30 p.m. | T 3-3 (OT) | |
| Wed., 3/5 | V Boys Ice Hockey | Tri-Town (Scrim.) | Home - Hotchkiss [Directions] | 6:00 p.m. | Cancelled | |
| Wed., 3/5 | V Boys Swimming and Diving | Lewis Mills | Home - Hotchkiss Pool [Directions] | 4:30 p.m. | Warm up at 4:30pm | |
| Sat., 3/8 | V Boys Swimming and Diving | Berkshire League Championship | Home - Hotchkiss Pool [Directions] | 1:00 p.m. | Warm up start 12 noon | |
| Wed., 4/2 | V Baseball | Pine Plains (NY) (Scrim.) | Home - High School Field [Directions] | 3:45 p.m. | ||
| Wed., 4/2 | JV Baseball | Pine Plains (NY) (Scrim.) | Home - High School Field [Directions] | 3:45 p.m. | ||
| Wed., 4/2 | V Softball | Pine Plains (NY) (Scrim.) | Away | 3:45 p.m. | ||
| Fri., 4/4 | V Baseball | Brookfield (Scrim.) | Home - Housatonic [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Baseball | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | L 6-9 | |
| Wed., 4/9 | JV Baseball | Terryville | Away - Lower Fisher Elementary [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Boys Outdoor Track | Northwestern, Nonnewaug | Home - Housatonic Track [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Wed., 4/9 | V Girls Lacrosse | Canton | Away - Canton High School [Directions] | 5:15 p.m. | W 12-8 | |
| Wed., 4/9 | V Girls Outdoor Track | Northwestern, Nonnewaug | Home - Housatonic Track [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Softball | Terryville | Home - HVRHS Field [Directions] | 3:45 p.m. | W 14-4 | |
| Wed., 4/9 | V Girls Tennis | Wamogo | Home [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 4/10 | V Boys Lacrosse | Nonnewaug (Scrim.) | Away [Directions] | 4:30 p.m. | L 8-9 | |
| Sat., 4/12 | V Baseball | Thomaston | Away - Thomaston HS Field [Directions] | 11:00 a.m. | L 2-3 | |
| Sat., 4/12 | JV Baseball | Thomaston | Away - Thomaston HS Field [Directions] | 1:00 p.m. | ||
| Mon., 4/14 | V Baseball | Mt. Everett (MA) | Home - Housatonic [Directions] | 4:00 p.m. | W 14-2 | |
| Mon., 4/14 | JV Baseball | Mt. Everett (MA) | Home - Housatonic [Directions] | 4:00 p.m. | ||
| Mon., 4/14 | V Boys Lacrosse | Litchfield Coop (Scrim.) | Away - Plumb Hill Field [Directions] | 4:30 p.m. | W 14-4 | |
| Mon., 4/14 | V Boys Tennis | Northwestern | Home - High School Courts [Directions] | 11:00 a.m. | W 3-2 | |
| Mon., 4/14 | V Girls Tennis | Northwestern | Away - Northwestern [Directions] | 11:00 a.m. | L 3-4 | |
| Thu., 4/17 | V Boys Golf | Litchfield | Home - Canaan Country Club [Directions] | 12:00 p.m. | L - 201 H - 204 | |
| Thu., 4/17 | V Boys Outdoor Track | Shepaug Valley, Gilbert | Away - Shepaug Valley High School Track [Directions] | 12:00 p.m. | ||
| Thu., 4/17 | V Girls Outdoor Track | Shepaug Valley, Gilbert | Away - Shepaug Valley High School Track [Directions] | 12:00 p.m. | Shepaug 72 - Housatonic 68 | |
| Mon., 4/21 | V Baseball | Nonnewaug | Away - Nonnewaug High School Field [Directions] | 3:45 p.m. | W 5-2 | |
| Mon., 4/21 | JV Baseball | Nonnewaug | Away - Woodbury Middle School [Directions] | 3:45 p.m. | ||
| Mon., 4/21 | V Boys Lacrosse | Holy Cross | Away - Holy Cross HS [Directions] | 4:00 p.m. | L 5-10 | |
| Mon., 4/21 | V Softball | Nonnewaug | Away - High School Field [Directions] | 3:45 p.m. | L 3-11 | |
| Tue., 4/22 | V Baseball | Gilbert | Home - High School Field [Directions] | 4:00 p.m. | W 10-1 | |
| Tue., 4/22 | V Boys Outdoor Track | Terryville, Litchfield, Lewis Mills | Away - New Terryville High School [Directions] | 3:45 p.m. | ||
| Tue., 4/22 | V Girls Lacrosse | Holy Cross | Home - Housatonic Field [Directions] | 4:00 p.m. | W 13-7 | |
| Tue., 4/22 | V Girls Outdoor Track | Terryville, Litchfield, Lewis Mills | Away - New Terryville High School [Directions] | 3:45 p.m. | Housatonic 90 - Litchfield 62 Housatonic 90- Mills 55 Housatonic 87- Terryville 60 | |
| Tue., 4/22 | V Softball | Thomaston | Home - High School Field [Directions] | 3:45 p.m. | L 8-1 | |
| Wed., 4/23 | V Baseball | Lewis Mills | Home - High School Field [Directions] | 3:45 p.m. | L 6-9 | |
| Wed., 4/23 | JV Baseball | Lewis Mills | Home - High School Field [Directions] | 3:45 p.m. | ||
| Wed., 4/23 | V Boys Lacrosse | Watertown | Home - Hotchkiss [Directions] | 4:00 p.m. | L 6-13 | |
| Wed., 4/23 | V Softball | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 3-18 | |
| Wed., 4/23 | V Girls Tennis | Litchfield | Away - Litchfield High School [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/24 | V Boys Golf | Northwestern | Home - Canaan Country Club [Directions] | 3:00 p.m. | NW - 189 H - 197 | |
| Thu., 4/24 | V Boys Tennis | Litchfield | Home - High School Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 4/24 | V Girls Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 6:00 p.m. | W 12-8 | |
| Fri., 4/25 | V Baseball | Northwestern | Home - High School Field [Directions] | 3:45 p.m. | W 4-2 | |
| Fri., 4/25 | JV Baseball | Northwestern | Away - NWR Varsity Field [Directions] | 3:45 p.m. | ||
| Fri., 4/25 | V Boys Tennis | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 1-4 | |
| Fri., 4/25 | V Softball | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | L 7-17 | |
| Fri., 4/25 | V Girls Tennis | Lewis Mills | Home - Housatonic Regional HS [Directions] | 3:45 p.m. | L 1-6 | |
| Sat., 4/26 | V Boys Lacrosse | Lewis Mills | Home - Hotchkiss [Directions] | 1:00 p.m. | L 3-17 | |
| Mon., 4/28 | V Baseball | Litchfield | Away - Community Field [Directions] | 3:45 p.m. | W 4-0 | |
| Mon., 4/28 | V Boys Lacrosse | St. Paul Catholic | Home - Hotchkiss [Directions] | 4:30 p.m. | L 4-7 | |
| Mon., 4/28 | V Boys Tennis | Nonnewaug | Home - High School Courts [Directions] | 3:45 p.m. | L 3-2 | |
| Mon., 4/28 | V Girls Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | 4:00 p.m. | L 10-11 | |
| Mon., 4/28 | V Softball | Litchfield | Home - High School Field [Directions] | 3:45 p.m. | W 21-1 | |
| Mon., 4/28 | V Girls Tennis | Nonnewaug | Away - Edgewood Bath and Tennis [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/29 | V Boys Golf | Shepaug Valley | Home - Canaan Country Club [Directions] | 3:00 p.m. | S - 171 H - 209 | |
| Tue., 4/29 | V Boys Outdoor Track | Shepaug Valley, Thomaston | Away - Shepaug [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Boys Tennis | Thomaston | Away - Thomaston Center School [Directions] | 3:45 p.m. | W 3-1 | |
| Tue., 4/29 | V Girls Outdoor Track | Shepaug Valley, Thomaston | Away - Shepaug [Directions] | 3:45 p.m. | Thomaston 64 - Housatonic 62 | |
| Tue., 4/29 | V Girls Tennis | Thomaston | Home - High School Courts [Directions] | 3:45 p.m. | L 0-4 | |
| Wed., 4/30 | JV Baseball | Shepaug Valley | Home - High School Field [Directions] | 3:45 p.m. | ||
| Thu., 5/1 | V Boys Golf | Woodland Hawk Invitational | Away - Oxford Greens | 8:00 a.m. | Cancelled | |
| Fri., 5/2 | V Baseball | Wamogo | Home - Housatonic [Directions] | 3:45 p.m. | W 7-3 | |
| Fri., 5/2 | JV Baseball | Wamogo | Home - High School Field [Directions] | 3:45 p.m. | ||
| Fri., 5/2 | V Boys Lacrosse | Wamogo | Away - Wamogo [Directions] | 4:00 p.m. | W 16-4 | |
| Fri., 5/2 | V Boys Tennis | Wamogo | Home - High School Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Fri., 5/2 | V Softball | Wamogo/Litchfield | Home - High School Field [Directions] | 3:45 p.m. | L 4-5 | |
| Fri., 5/2 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Mon., 5/5 | V Baseball | Terryville | Home - High School Field [Directions] | 3:45 p.m. | L 2-3 | |
| Mon., 5/5 | JV Baseball | Terryville | Home - High School Field [Directions] | 3:45 p.m. | ||
| Mon., 5/5 | V Boys Golf | Terryville | Home - TBA [Directions] | 3:00 p.m. | Cancelled | |
| Mon., 5/5 | V Boys Tennis | Thomaston | Home - High School Courts [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 5/5 | V Softball | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | W 19-3(5) | |
| Mon., 5/5 | V Girls Tennis | Thomaston | Away - Thomaston Center School [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/6 | V Baseball | Shepaug Valley | Home - High School Field [Directions] | 3:45 p.m. | W 7-3 | |
| Tue., 5/6 | V Boys Outdoor Track | Nonnewaug, Wamogo | Home - Housatonic Track [Directions] | 3:45 p.m. | ||
| Tue., 5/6 | V Boys Tennis | Shepaug Valley | Home - High School Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 5/6 | V Girls Lacrosse | Capital Prep | Away [Directions] | TBA | W 18-0 | |
| Tue., 5/6 | V Girls Outdoor Track | Nonnewaug, Wamogo | Home - Housatonic Track [Directions] | 3:45 p.m. | Housatonic 125 - 21 | |
| Tue., 5/6 | V Softball | Shepaug Valley | Away - Dick Ayer Field [Directions] | 3:45 p.m. | L 1-2 | |
| Tue., 5/6 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley High School Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/7 | V Baseball | Thomaston | Home - High School Field [Directions] | 3:45 p.m. | L 0-6 | |
| Wed., 5/7 | JV Baseball | Thomaston | Home - High School Field [Directions] | 3:45 p.m. | ||
| Wed., 5/7 | V Boys Golf | Gilbert, Lewis Mills | Away - Fairview Farm GC [Directions] | 3:00 p.m. | H -227 LM 188 G -246 | |
| Wed., 5/7 | V Boys Lacrosse | Amistad | Home - Hotchkiss [Directions] | 4:30 p.m. | W 11-0 | |
| Wed., 5/7 | V Boys Tennis | Northwestern | Away - Northwestern [Directions] | 3:45 p.m. | L 4-1 | |
| Wed., 5/7 | V Girls Lacrosse | Amistad | Away - Clinton Avenue School [Directions] | 4:30 p.m. | W 20-6 | |
| Wed., 5/7 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | 3:45 p.m. | L 0-15(6) | |
| Wed., 5/7 | V Girls Tennis | Northwestern | Home [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 5/8 | V Boys Lacrosse | Amistad | Away - Clinton Avenue School [Directions] | 4:30 p.m. | W 14-3 | |
| Fri., 5/9 | V Boys Golf | Litchfield, Terryville | Home - Hotchkiss Golf Course [Directions] | 3:00 p.m. | H -203 L -180 T -215 | |
| Fri., 5/9 | V Boys Tennis | Gilbert | Away - Housatonic [Directions] | 3:45 p.m. | W 4-1 | |
| Fri., 5/9 | V Boys Tennis | Gilbert | Home - High School Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 5/9 | V Girls Lacrosse | Lewis Mills | Home - Housatonic Field [Directions] | 4:00 p.m. | W 11-10 | |
| Fri., 5/9 | V Softball | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | L 17-18 | |
| Sat., 5/10 | V Boys Lacrosse | Holy Cross | Home - Hotchkiss [Directions] | 1:00 p.m. | W 9-8(OT) | |
| Sat., 5/10 | V Boys Outdoor Track | Spartan Invitational | Away - Shepaug Valley High School | 10:00 a.m. | ||
| Sat., 5/10 | V Girls Lacrosse | Holy Cross | Away - Holy Cross HS [Directions] | 10:00 a.m. | W 17-7 | |
| Sat., 5/10 | V Girls Outdoor Track | Spartan Invitational | Away - Shepaug Valley High School | 10:00 a.m. | ||
| Sat., 5/10 | JV Softball | Northwestern Jamboree | Away - Northwestern High School | 10:00 a.m. | ||
| Mon., 5/12 | V Baseball | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 5-1 | |
| Mon., 5/12 | V Boys Golf | Thomaston, Nonnewaug | Away - Stonybrook Golf Course [Directions] | 3:00 p.m. | H - 216 T - 165 N - 176 | |
| Mon., 5/12 | V Boys Lacrosse | Wamogo | Home - Hotchkiss [Directions] | 4:00 p.m. | W 14-6 | |
| Mon., 5/12 | V Boys Outdoor Track | Terryville, Gilbert, Wolcott Tech | Home - Housatonic Track [Directions] | 3:45 p.m. | ||
| Mon., 5/12 | V Girls Outdoor Track | Terryville, Gilbert, Wolcott Tech | Home - Housatonic Track [Directions] | 3:45 p.m. | Housatonic | |
| Mon., 5/12 | V Softball | Gilbert | Home - High School Field [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 5/13 | V Boys Golf | Gilbert, Northwestern | Home - Hotchkiss Golf Course [Directions] | 3:00 p.m. | H -201 N -199 G-NS | |
| Tue., 5/13 | V Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 6:00 p.m. | L 3-7 | |
| Tue., 5/13 | V Girls Lacrosse | Watertown | Home - Housatonic Field [Directions] | 4:00 p.m. | W 13-9 | |
| Tue., 5/13 | JV Softball | Shepaug Valley | Home - Housatonic [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | V Boys Tennis | Litchfield | Away - Litchfield High School [Directions] | 3:45 p.m. | W 4-1 | |
| Wed., 5/14 | V Girls Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | 5:00 p.m. | L 13-15 | |
| Wed., 5/14 | V Girls Tennis | Litchfield | Home [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/15 | V Baseball | Nonnewaug | Home - High School Field [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 5/15 | JV Baseball | Nonnewaug | Home - High School Field [Directions] | 3:45 p.m. | ||
| Thu., 5/15 | V Boys Golf | Litchfield, Thomaston | Away - Litchfield CC [Directions] | 3:45 p.m. | L -169 H -202 | |
| Thu., 5/15 | V Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | 4:00 p.m. | L 2-18 | |
| Thu., 5/15 | V Girls Lacrosse | Amistad | Home - Housatonic Field [Directions] | 4:30 p.m. | W 19-3 | |
| Thu., 5/15 | V Softball | Nonnewaug | Home - Housatonic High school [Directions] | 3:45 p.m. | L 11-13 | |
| Thu., 5/15 | V Girls Tennis | Gilbert | Home - Gilbert [Directions] | 3:45 p.m. | W 6-1 | |
| Sat., 5/17 | V Boys Lacrosse | Bristol Central | Away - BRISTOL EASTERN HIGH [Directions] | 12:00 p.m. | W Forfeit | |
| Sat., 5/17 | V Girls Lacrosse | Valley Regional | Home - Housatonic Field [Directions] | 12:00 p.m. | W 16-9 | |
| Mon., 5/19 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | 3:45 p.m. | W 3-1 | |
| Mon., 5/19 | JV Baseball | Lewis Mills | Away - Lewis Mills JV Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/19 | V Boys Golf | Litchfield, Thomaston | Away [Directions] | 3:00 p.m. | Cancelled | |
| Mon., 5/19 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | W 13-10 | |
| Mon., 5/19 | V Boys Tennis | Nonnewaug | Away - Edgewood Bath and Tennis [Directions] | 3:45 p.m. | L 4-1 | |
| Mon., 5/19 | V Girls Lacrosse | East Catholic | Home - Housatonic Field [Directions] | 4:15 p.m. | W 15-12 | |
| Mon., 5/19 | V Softball | Lewis Mills | Home - High School Field [Directions] | 3:45 p.m. | W 7-6 | |
| Tue., 5/20 | V Baseball | Mt. Everett (MA) | Away | 4:00 p.m. | W 5-2 | |
| Tue., 5/20 | JV Baseball | Mt. Everett (MA) | Away | 4:00 p.m. | ||
| Tue., 5/20 | V Boys Golf | Shepaug Valley, Lewis Mills | Away - Washington Club [Directions] | 3:15 p.m. | S-207 LM-183 H-228 | |
| Tue., 5/20 | V Boys Lacrosse | Canton | Away - Canton High School [Directions] | 4:00 p.m. | L 4-15 | |
| Tue., 5/20 | V Girls Lacrosse | Capital Prep | Home - Housatonic Field [Directions] | 4:00 p.m. | W 18-0 | |
| Tue., 5/20 | V Softball | Canton | Home - High School Field [Directions] | 4:15 p.m. | L 0-4 | |
| Wed., 5/21 | V Baseball | Northwestern | Away - NWR Varsity Field [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 5/21 | JV Baseball | Northwestern | Home - High School JV Field [Directions] | 3:45 p.m. | ||
| Wed., 5/21 | V Boys Golf | Thomaston | Away - Norfolk CC [Directions] | 3:30 p.m. | H-205 T-164 | |
| Wed., 5/21 | V Boys Golf | Northwestern, Terryville | Away - Norfolk CC [Directions] | 3:30 p.m. | N-175 T-220 H-205 | |
| Wed., 5/21 | V Boys Lacrosse | Granby Memorial | Home - Hotchkiss [Directions] | 4:00 p.m. | L 5-15 | |
| Wed., 5/21 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley High School Courts [Directions] | 3:45 p.m. | W 4-1 | |
| Wed., 5/21 | V Softball | Northwestern | Home - High School Field [Directions] | 3:45 p.m. | L 2-13 | |
| Wed., 5/21 | V Girls Tennis | Shepaug Valley | Home [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/22 | V Boys Golf | Nonnewaug | Home - Canaan Country Club [Directions] | 3:00 p.m. | H-190 N-175 | |
| Fri., 5/23 | V Baseball | Litchfield | Home - High School Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 5/23 | V Boys Tennis | Lewis Mills | Home - High School Courts [Directions] | 3:45 p.m. | L 3-2 | |
| Fri., 5/23 | V Girls Tennis | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 2-5 | |
| Sat., 5/24 | V Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | 1:00 p.m. | W 18-3 | |
| Tue., 5/27 | V Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | 4:00 p.m. | L 1-12 | |
| Tue., 5/27 | JV Baseball | Shepaug Valley | Away - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/27 | V Boys Lacrosse | Lewis Mills | Away [Directions] | 5:30 p.m. | ||
| Tue., 5/27 | V Girls Lacrosse | Holy Cross | Home - Hotchkiss [Directions] | 3:30 p.m. | ||
| Tue., 5/27 | V Softball | Shepaug Valley | Home - High School Field [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/28 | V Baseball | Wamogo | Home - Housatonic Regional [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 5/28 | JV Baseball | Wamogo | Home - Housatonic [Directions] | 3:45 p.m. | ||
| Wed., 5/28 | V Girls Lacrosse | East Catholic | Away - East Catholic Lower Field [Directions] | 4:30 p.m. | L 17-12 | |
| Wed., 5/28 | V Softball | Wamogo/Litchfield | Home - Housatonic Regional [Directions] | 3:45 p.m. | L 3-16 | |
| Wed., 5/28 | V Girls Tennis | Gilbert | Away - Gilbert [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/29 | V Girls Lacrosse | Lewis Mills | Home - Watertown High School [Directions] | 7:00 p.m. | ||
| Thu., 5/29 | JV Softball | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | ||
| Thu., 5/29 | V Girls Tennis | Nonnewaug | Home [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 6/2 | V Baseball | Old Lyme | Home [Directions] | 3:30 p.m. | ||
| Tue., 6/3 | V Girls Lacrosse | Lewis Mills | Home [Directions] | 5:00 p.m. | ||
| Wed., 6/4 | V Boys Outdoor Track | Class S Meet | Away | TBA | ||
| Wed., 6/4 | V Girls Outdoor Track | Class S Meet | Away | TBA | ||