| Watertown 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 479 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 9/8 | V Field Hockey | Wamogo | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 9/8 | JV Field Hockey | Wamogo | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Fri., 9/9 | V Football | Crosby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 34-50 | |
| Fri., 9/9 | V Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | L 2-5 | |
| Sat., 9/10 | V Boys Soccer | Woodland | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | T 1-1 | |
| Sat., 9/10 | V Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 9/10 | JV Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | Canceled | Cancelled | |
| Mon., 9/12 | V Girls Volleyball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | L 2-3 | |
| Mon., 9/12 | JV Girls Volleyball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:30 p.m. | L 0-2 | |
| Tue., 9/13 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | W 4-0 | |
| Tue., 9/13 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 9/13 | V Girls Volleyball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/13 | JV Girls Volleyball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | L 0-2 | |
| Wed., 9/14 | V Boys Cross Country | Torrington, WCA, Wilby | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | L 2-0 | |
| Wed., 9/14 | V Girls Cross Country | Torrington, WCA, Wilby | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Seymour | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 3-1 | |
| Thu., 9/15 | V Football | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | L 12-54 | |
| Thu., 9/15 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 5:00 p.m. | ||
| Fri., 9/16 | V Boys Soccer | WCA | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:45 p.m. | W 1-6 | |
| Fri., 9/16 | V Girls Soccer | Naugatuck | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | W 6-1 | |
| Fri., 9/16 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/16 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 9/17 | V Boys Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 9:00 a.m. | ||
| Sat., 9/17 | FM Football | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/17 | V Girls Soccer | Weston | Away - Weston HS-WHS Stadium Field [Directions] | 12:30 p.m. | L 0-1 | |
| Sat., 9/17 | JV Girls Soccer | Weston | Away - Weston HS-WHS Stadium Field [Directions] | 10:30 a.m. | ||
| Mon., 9/19 | V Field Hockey | Thomaston | Away - Thomaston HS-Gym [Directions] | 3:45 p.m. | T 1-1 | |
| Mon., 9/19 | JV Field Hockey | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Derby, Naugatuck | Away - Witek Park [Directions] | 3:45 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Crosby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 4-0 | |
| Tue., 9/20 | V Girls Cross Country | Derby, Naugatuck | Away - Witek Park [Directions] | 3:45 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | W 5-1 | |
| Tue., 9/20 | V Girls Swimming and Diving | Kennedy | Home - Watertown HS-Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/20 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/21 | JV Girls Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/22 | V Boys Soccer | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 1-0 | |
| Fri., 9/23 | V Football | Woodland | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-47 | |
| Fri., 9/23 | V Field Hockey | Litchfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | W 8-0 | |
| Fri., 9/23 | JV Field Hockey | Litchfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Fri., 9/23 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 9/23 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | ||
| Fri., 9/23 | V Girls Volleyball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:45 p.m. | L 0-3 | |
| Fri., 9/23 | JV Girls Volleyball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | FM Football | Woodland | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Sat., 9/24 | V Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 3:00 p.m. | L 4-0 | |
| Sat., 9/24 | V Field Hockey | North Branford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:30 a.m. | L 1-5 | |
| Sat., 9/24 | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -Upper Soccer Field [Directions] | Canceled | Cancelled | |
| Mon., 9/26 | JV Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 5:00 p.m. | ||
| Mon., 9/26 | JV Girls Soccer | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Tue., 9/27 | V Boys Cross Country | Kennedy, Oxford, Wolcott | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/27 | V Boys Soccer | Wilby | Away - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | W 2-5 | |
| Tue., 9/27 | V Girls Cross Country | Kennedy, Oxford, Wolcott | Home - Watertown HS-Veteran's Park [Directions] | 3:30 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 9/27 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | W 3 to 2 | |
| Tue., 9/27 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 9/28 | V Girls Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | ||
| Thu., 9/29 | V Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 2-1 | |
| Thu., 9/29 | V Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 9/29 | V Girls Volleyball | Newington | Away - Newington HS-Gym [Directions] | 5:45 p.m. | L 0-3 | |
| Thu., 9/29 | JV Girls Volleyball | Newington | Away - Newington HS-Gym [Directions] | 4:45 p.m. | ||
| Thu., 9/29 | FR Girls Volleyball | Newington | Away - Newington HS-Gym [Directions] | 3:45 p.m. | ||
| Fri., 9/30 | V Football | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 6:30 p.m. | W 28-0 | |
| Fri., 9/30 | V Girls Soccer | Oxford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 6-0 | |
| Fri., 9/30 | V Girls Volleyball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/30 | JV Girls Volleyball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Sat., 10/1 | FM Football | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 10/1 | JV Girls Soccer | Torrington | Home - Watertown HS [Directions] | Postponed | ||
| Mon., 10/3 | V Boys Soccer | Kennedy | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:45 p.m. | W 3-6 | |
| Mon., 10/3 | V Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/3 | JV Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | JV Boys Soccer | Kennedy | Away - West Side MS-Waterbury-Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/4 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 4-0 | |
| Tue., 10/4 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Wed., 10/5 | V Girls Soccer | Woodland | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-1 | |
| Thu., 10/6 | V Boys Cross Country | Woodland, Crosby, Seymour | Away - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Cross Country | Woodland, Crosby, Seymour | Away - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 10/6 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/7 | V Football | Seymour | Away - Seymour HS-turf field [Directions] | 7:00 p.m. | L 0-42 | |
| Fri., 10/7 | V Girls Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 6:00 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/7 | JV Girls Volleyball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Sat., 10/8 | FM Football | Seymour | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | FR Girls Volleyball | Oxford, Torrington | Away - Oxford HS-Main Gym [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Mon., 10/10 | V Boys Soccer | Pomperaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:00 p.m. | L 0-5 | |
| Mon., 10/10 | V Field Hockey | Pomperaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | L 0-1 | |
| Mon., 10/10 | V Girls Soccer | Pomperaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 1:00 p.m. | T 0-0 | |
| Tue., 10/11 | V Boys Cross Country | Holy Cross, St. Paul Catholic | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Boys Soccer | Naugatuck | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | T 1-1 | |
| Tue., 10/11 | V Girls Cross Country | Holy Cross, St. Paul Catholic | Home - Watertown HS-Veteran's Park [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 10/11 | V Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 10/11 | JV Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/13 | V Girls Soccer | Ansonia | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/13 | V Girls Volleyball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/13 | JV Girls Volleyball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Fri., 10/14 | V Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 2-1 | |
| Fri., 10/14 | JV Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby HS-Gil Cyr Natatorium [Directions] | 5:00 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 10/14 | JV Girls Volleyball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Mon., 10/17 | V Boys Soccer | Torrington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 1-0 | |
| Mon., 10/17 | V Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 10/18 | V Field Hockey | Thomaston | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/18 | JV Field Hockey | Thomaston | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-1 | |
| Tue., 10/18 | JV Girls Soccer | Woodland | Home - Veterans Memorial Park-Veterans Park Field #2 [Directions] | Postponed | ||
| Tue., 10/18 | V Girls Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 5:00 p.m. | ||
| Tue., 10/18 | V Girls Volleyball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 10/18 | JV Girls Volleyball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Wed., 10/19 | V Boys Cross Country | NVL XC Championships | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 2:00 p.m. | ||
| Wed., 10/19 | V Boys Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | T 0-0 | |
| Wed., 10/19 | V Girls Cross Country | NVL XC Championships | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 2:00 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:30 p.m. | W 0-2 | |
| Thu., 10/20 | JV Boys Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | Postponed | ||
| Thu., 10/20 | V Field Hockey | Nonnewaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 2-1 | |
| Thu., 10/20 | JV Field Hockey | Nonnewaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | ||
| Thu., 10/20 | JV Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:30 p.m. | ||
| Thu., 10/20 | V Girls Swimming and Diving | Oxford | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Thu., 10/20 | V Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 10/20 | JV Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 10/21 | V Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 7:00 p.m. | L 0-43 | |
| Sat., 10/22 | FM Football | Naugatuck | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:00 p.m. | ||
| Sat., 10/22 | JV Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Soccer | Derby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 7-0 | |
| Mon., 10/24 | V Girls Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 6:00 p.m. | W 8-0 | |
| Mon., 10/24 | V Girls Volleyball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Mon., 10/24 | JV Girls Volleyball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Tue., 10/25 | JV Boys Soccer | Torrington | Home - Watertown HS [Directions] | Postponed | ||
| Tue., 10/25 | V Field Hockey | Litchfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 6-0 | |
| Tue., 10/25 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | Postponed | ||
| Tue., 10/25 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/25 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 10/25 | FR Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 3:15 p.m. | ||
| Wed., 10/26 | V Boys Soccer | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 1-0 | |
| Wed., 10/26 | V Girls Soccer | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:30 p.m. | W 2-1 | |
| Thu., 10/27 | JV Boys Soccer | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Fri., 10/28 | V Football | Wilby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 42-8 | |
| Fri., 10/28 | V Field Hockey | Northwestern | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 10/28 | JV Field Hockey | Northwestern | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Sat., 10/29 | FM Football | Wilby | Away - Wilby HS-Football Field [Directions] | 10:30 a.m. | ||
| Mon., 10/31 | V Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 1-0 | |
| Mon., 10/31 | JV Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | ||
| Wed., 11/2 | FM Football | Ansonia | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | ||
| Fri., 11/4 | V Football | Ansonia | Away - Nolan Field-Ansonia-Football Field [Directions] | 6:00 p.m. | L 0-48 | |
| Thu., 11/10 | V Football | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 20-7 | |
| Mon., 11/14 | FM Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | ||
| Sat., 11/19 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 9:00 a.m. | ||
| Thu., 11/24 | V Football | Torrington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | W 33-6 | |
| Tue., 12/13 | V Girls Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 31-34 | |
| Tue., 12/13 | JV Girls Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Trumbull | Home - Taft School-Mays [Directions] | 8:00 p.m. | L 3-4 | |
| Wed., 12/14 | V Wrestling | Weston | Away - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 48 Pomperaug 21 | |
| Fri., 12/16 | V Boys Basketball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 36-82 | |
| Fri., 12/16 | JV Boys Basketball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/16 | V Boys Swimming and Diving | Nonnewaug | Home - Watertown HS-Pool [Directions] | 4:30 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | W 53-32 | |
| Fri., 12/16 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Postponed | ||
| Sat., 12/17 | V Boys Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 1-3 | |
| Sat., 12/17 | V Wrestling | Bacon Academy, New Canaan, Nonnewaug, Portland, Wethersfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 9:00 a.m. | ||
| Mon., 12/19 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | L 17-84 | |
| Mon., 12/19 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/19 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 12/20 | V Girls Basketball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 59-47 | |
| Tue., 12/20 | JV Girls Basketball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/20 | Unified Sports Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 2:30 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall-Ice Rink [Directions] | 6:00 p.m. | W 1-0 | |
| Wed., 12/21 | V Wrestling | Masuk | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Masuk 46 Pomperaug 27 | |
| Thu., 12/22 | V Boys Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 44-60 | |
| Thu., 12/22 | JV Boys Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/22 | FR Boys Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | L 52-54 | |
| Fri., 12/23 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | Postponed | ||
| Tue., 12/27 | V Boys Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 38-63 | |
| Tue., 12/27 | JV Boys Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/27 | FR Boys Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/27 | V Girls Basketball | Glastonbury | Home - Wolcott HS-Main Gym [Directions] | 5:00 p.m. | L 29-52 | |
| Wed., 12/28 | V Boys Ice Hockey | Cheshire | Home - Taft School-Mays [Directions] | 1:00 p.m. | W 5-3 | |
| Wed., 12/28 | V Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | L 49-64 | |
| Thu., 12/29 | V Girls Gymnastics | Farmington, Ellington/Tolland | Away - Farmington Valley Gymnastics & More-Farmington Valley Gymnastics-Plainville [Directions] | 5:45 p.m. | 111.75 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 6:00 p.m. | ||||||
| Fri., 12/30 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 38-86 | |
| Fri., 12/30 | JV Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/30 | FR Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 12/30 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Taft School-Mays [Directions] | 3:30 p.m. | W 5-3 | |
| Fri., 12/30 | V Wrestling | Trumbull, Amity, Berlin, Greenwich, Foran, Manchester, Masuk, Minnechaug (MA), TBA, Stratford | Away - Trumbull HS-Aux Gym | 8:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Fri., 12/30 | V Girls Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 53-64 | |
| Fri., 12/30 | JV Girls Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/30 | FR Girls Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/3 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 35-69 | |
| Tue., 1/3 | JV Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/3 | V Boys Swimming and Diving | Shepaug Valley | Home - Watertown HS-Pool [Directions] | 3:45 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 58-49(OT) | |
| Tue., 1/3 | JV Girls Basketball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | North Haven | Away - Northford-Red [Directions] | 8:30 p.m. | L 2-3 | |
| Wed., 1/4 | V Wrestling | Brookfield/Shepaug | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Brookfield 28 Pomperaug 24 | |
| Fri., 1/6 | V Boys Basketball | Derby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 64-61 | |
| Fri., 1/6 | JV Boys Basketball | Derby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Kennedy | Home - Watertown HS-Pool [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | W 45-15 | |
| Sat., 1/7 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 8:10 p.m. | L 3-4 | |
| Sat., 1/7 | JV Wrestling | Bristol Eastern, Avon, Berlin, Branford, Bristol Central, East Hartford, Enfield, Farmington, Guilford, Ledyard, Middletown, TBA, New Fairfield, New Milford, Wethersfield, Hall | Away - Bristol Eastern HS-Gym | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 1/7 | V Girls Gymnastics | Farmington | Away - Farmington Valley Gymnastics & More-Farmington Valley Gymnastics-Plainville [Directions] | 4:45 p.m. | 117.60 | |
| Tue., 1/10 | V Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | L 56-87 | |
| Tue., 1/10 | JV Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 48-29 | |
| Tue., 1/10 | JV Girls Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Branford | Home - Taft School-Mays [Directions] | 8:00 p.m. | W 4-2 | |
| Wed., 1/11 | V Wrestling | Stratford | Away - Stratford HS-Gym [Directions] | 6:00 p.m. | Stratford 54 Pomperaug 18 | |
| Wed., 1/11 | V Girls Gymnastics | Fairfield Ludlowe, New Canaan | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 121.85 | |
| Fri., 1/13 | V Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 44-57 | |
| Fri., 1/13 | JV Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS-CHS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | Cancelled | |
| Fri., 1/13 | JV Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | FR Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | Lyman Hall | Away - Northford-Red [Directions] | 5:00 p.m. | W 5-2 | |
| Sat., 1/14 | V Wrestling | Art Powers Duals | Away - Berlin HS-Jim Day Gymnasium | 9:00 a.m. | ||
| Mon., 1/16 | V Girls Gymnastics | Newtown | Home - Newtown Gymnastics [Directions] | 12:00 p.m. | 129.55 | |
| Tue., 1/17 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 48-79 | |
| Tue., 1/17 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 40-57 | |
| Tue., 1/17 | JV Girls Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | FR Girls Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/18 | V Wrestling | Bunnell | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Bunnell 45 Pomperaug 19 | |
| Fri., 1/20 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | L 49-87 | |
| Fri., 1/20 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:15 p.m. | ||
| Fri., 1/20 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | 8:00 p.m. | L 0-2 | |
| Fri., 1/20 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Fri., 1/20 | V Girls Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 47-52 | |
| Fri., 1/20 | JV Girls Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/21 | FR Boys Basketball | Wamogo | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 12:30 p.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-1 | |
| Sat., 1/21 | V Wrestling | Colter Abely Wrestling Tournament | Away - Mercy HS-Gym | 8:00 a.m. | ||
| Sat., 1/21 | V Girls Gymnastics | Newtown | Home - Newtown Gymnastics [Directions] | 5:30 p.m. | 122.90 | |
| Tue., 1/24 | V Boys Basketball | Bristol Eastern | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:45 p.m. | L 44-70 | |
| Tue., 1/24 | JV Boys Basketball | Bristol Eastern | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Bristol Eastern | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/26 | V Wrestling | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/26 | V Girls Gymnastics | New Milford, Brookfield, Ellington/Tolland | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 48-58 | |
| Fri., 1/27 | JV Boys Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Woodland | Home - Watertown HS-Pool [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | L 46-65 | |
| Fri., 1/27 | JV Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 1/27 | Unified Sports Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:30 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Farmington Valley Generals | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 2-3 | |
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Away - Brookfield HS-BHS Small Gym | 9:30 a.m. | ||
| Mon., 1/30 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | ||
| Tue., 1/31 | V Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | L 51-55 | |
| Tue., 1/31 | JV Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/31 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 63-56 | |
| Tue., 1/31 | JV Girls Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/1 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 2/1 | V Wrestling | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:00 p.m. | ||
| Thu., 2/2 | V Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 66-24 | |
| Thu., 2/2 | JV Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 38-65 | |
| Fri., 2/3 | JV Boys Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 6:00 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 30-47 | |
| Fri., 2/3 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | FR Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | FR Boys Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 10:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:30 p.m. | ||||||
| Sat., 2/4 | V Boys Ice Hockey | North Branford | Away - Northford-Red [Directions] | 2:30 p.m. | T 3-3 | |
| Mon., 2/6 | V Wrestling | Notre Dame-Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/7 | V Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 54-57 | |
| Tue., 2/7 | JV Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | Litchfield | Home - Watertown HS-Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/7 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 54-61 | |
| Tue., 2/7 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Masuk | Home - Taft School-Mays [Directions] | 8:00 p.m. | T 1-1 | |
| Fri., 2/10 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 49-79 | |
| Fri., 2/10 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/10 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:30 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 48-49 | |
| Fri., 2/10 | JV Girls Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/11 | FR Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Guilford | Away - East Haven HS-Veterans Rink [Directions] | 1:00 p.m. | L 2-4 | |
| Sat., 2/11 | FR Girls Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Mon., 2/13 | V Boys Ice Hockey | St. Joseph | Home - Taft School-Mays [Directions] | 8:15 p.m. | W 1-0 | |
| Tue., 2/14 | V Boys Basketball | Kaynor Tech | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 56-54 | |
| Tue., 2/14 | JV Boys Basketball | Kaynor Tech | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/14 | FR Boys Basketball | Kaynor Tech | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | East Haven Coop | Away - East Haven HS-Veterans Rink [Directions] | 7:30 p.m. | T 2-2(OT) | |
| Thu., 2/16 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 51-86 | |
| Thu., 2/16 | JV Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/16 | FR Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/17 | V Boys Basketball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 58-102 | |
| Fri., 2/17 | JV Boys Basketball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/17 | FR Boys Basketball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/17 | V Boys Swimming and Diving | Holy Cross | Home - Watertown HS-Pool [Directions] | 5:30 p.m. | ||
| Sat., 2/18 | V Boys Ice Hockey | Amity | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-0 | |
| Mon., 2/20 | V Girls Gymnastics | Joel Barlow, Newtown, Oxford, Pomperaug | Away - Gymnastics Revolution [Directions] | 5:00 p.m. | 123.70 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Tue., 2/21 | FR Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Wed., 2/22 | V Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:00 p.m. | L 63-83 | |
| Wed., 2/22 | JV Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 4:15 p.m. | ||
| Wed., 2/22 | V Boys Ice Hockey | Daniel Hand | Away - Northford-Red [Directions] | 5:00 p.m. | W 6-4 | |
| Fri., 2/24 | V Boys Swimming and Diving | Torrington | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Sat., 2/25 | FR Boys Basketball | Nonnewaug, Wamogo | Away - Nonnewaug HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 4/1 | FR Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/3 | V Baseball | Seymour | Home - Deland Field-Deland field [Directions] | 2:45 p.m. | L 14-6 | |
| Mon., 4/3 | V Girls Lacrosse | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 5:15 p.m. | L 18-2 | |
| Mon., 4/3 | JV Girls Lacrosse | Southington | Away - Southington HS-8 SubVLacrosse/Soccer [Directions] | 4:15 p.m. | ||
| Mon., 4/3 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 3:45 p.m. | L 6-16 | |
| Mon., 4/3 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/4 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:00 p.m. | L 13-3 | |
| Tue., 4/4 | V Boys Outdoor Track | Seymour | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 4/4 | V Girls Outdoor Track | Seymour | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 4/4 | V Girls Tennis | St. Paul Catholic | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Wed., 4/5 | V Baseball | WCA | Away - Bucks Hill (MONTOE) Park-Baseball Field [Directions] | 3:45 p.m. | W 17-2 | |
| Wed., 4/5 | V Boys Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 15-3 | |
| Wed., 4/5 | JV Boys Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Softball Field [Directions] | 5:15 p.m. | ||
| Wed., 4/5 | V Girls Lacrosse | Litchfield Coop | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 12-8 | |
| Wed., 4/5 | JV Girls Lacrosse | Litchfield Coop | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:30 p.m. | ||
| Wed., 4/5 | V Softball | WCA | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 16-4 | |
| Wed., 4/5 | V Girls Tennis | Woodland | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 4/6 | FR Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | 3:45 p.m. | L 16-2 | |
| Thu., 4/6 | V Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | 3:00 p.m. | L 2-3 | |
| Thu., 4/6 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 4/8 | V Baseball | Woodland | Home - Deland Field-Deland field [Directions] | 11:00 a.m. | L 11-1 | |
| Sat., 4/8 | V Boys Lacrosse | Newington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | W 20-10 | |
| Mon., 4/10 | V Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 11:00 a.m. | W 16-1 | |
| Mon., 4/10 | V Softball | Crosby | Home - Watertown High-Softball Field [Directions] | 11:00 a.m. | W 21-3 | |
| Mon., 4/10 | V Girls Tennis | Crosby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 11:00 p.m. | W 7-0 | |
| Tue., 4/11 | V Boys Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 1:00 p.m. | W 19-9 | |
| Tue., 4/11 | V Boys Outdoor Track | St. Paul Catholic, Wilby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | V Girls Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 1:00 p.m. | W 17-10 | |
| Tue., 4/11 | V Girls Outdoor Track | St. Paul Catholic, Wilby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | V Softball | Thomaston | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 8-4 | |
| Wed., 4/12 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 11:00 a.m. | L 9-5 | |
| Wed., 4/12 | V Boys Golf | Wolcott | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 12:00 p.m. | Wat 201 - Wol 255 Medalist - Colin Leach 49 | |
| Wed., 4/12 | V Softball | Ansonia | Home - Watertown High-Softball Field [Directions] | 11:00 a.m. | W 12-0 | |
| Wed., 4/12 | V Girls Tennis | Ansonia | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/13 | V Boys Golf | Naugatuck | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 1:00 p.m. | Wat 188 - Naugatuck 238 Medalist - Nathan LaMadeleine 45 | |
| Thu., 4/13 | V Boys Tennis | Southington | Away - Southington HS-Tennis Courts [Directions] | 10:30 a.m. | L 0-5 | |
| Fri., 4/14 | V Baseball | Naugatuck | Home - Deland Field-Deland field [Directions] | 11:00 a.m. | W 11-10 | |
| Fri., 4/14 | V Boys Tennis | Naugatuck | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 11:00 a.m. | L 2-3 | |
| Fri., 4/14 | V Boys Tennis | Crosby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 12:00 p.m. | W 5-0 | |
| Fri., 4/14 | V Girls Lacrosse | Newington | Away - Newington HS-Clem Lemire Turf Field (150 New Britain Ave) [Directions] | 3:45 p.m. | L 16-13 | |
| Fri., 4/14 | JV Girls Lacrosse | Newington | Away - Newington HS-Clem Lemire Turf Field (150 New Britain Ave) [Directions] | 5:30 p.m. | ||
| Fri., 4/14 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 1:00 p.m. | W 1-0 | |
| Fri., 4/14 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Sat., 4/15 | JV Boys Lacrosse | Pomperaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Sat., 4/15 | V Girls Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | L 18-4 | |
| Sat., 4/15 | JV Girls Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Tue., 4/18 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Tue., 4/18 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | L 0-5 | |
| Tue., 4/18 | JV Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | V Baseball | Torrington | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 7-0 | |
| Wed., 4/19 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:00 p.m. | ||
| Wed., 4/19 | V Boys Lacrosse | Lewis Mills | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:15 p.m. | L 5-11 | |
| Wed., 4/19 | V Boys Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 4/19 | V Boys Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 5:30 p.m. | L 2-3 | |
| Wed., 4/19 | V Girls Lacrosse | New Milford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | L 14-10 | |
| Wed., 4/19 | V Softball | Torrington | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 4/20 | V Boys Golf | Oxford, Seymour | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | Wat 195 - OX/Sey 224 Medalist Tyler Yacawych 43 | |
| Thu., 4/20 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 4/21 | V Baseball | Derby | Away - Payden Park [Directions] | 5:30 p.m. | L 12-5 | |
| Fri., 4/21 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:30 p.m. | W 12-11 | |
| Fri., 4/21 | V Girls Lacrosse | Shelton | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 12-11 | |
| Fri., 4/21 | V Softball | Derby | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 20-3 | |
| Sat., 4/22 | JV Baseball | Wolcott | Away - Wolcott HS-Baseball Diamond [Directions] | 10:00 a.m. | L 13-0 | |
| Sat., 4/22 | V Boys Lacrosse | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 10:00 a.m. | L 13-2 | |
| Sat., 4/22 | JV Boys Lacrosse | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 11:30 a.m. | ||
| Mon., 4/24 | V Baseball | Wilby | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | W 12-0 | |
| Mon., 4/24 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | Wat 178 - Torr 219 Medalist - Nathan LaMadeleine | |
| Mon., 4/24 | V Boys Lacrosse | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 15-11 | |
| Mon., 4/24 | V Boys Tennis | Wilby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 4/24 | V Girls Lacrosse | Housatonic Regional | Away - Housatonic Valley Regional High-football field [Directions] | 3:45 p.m. | W 18-9 | |
| Mon., 4/24 | V Softball | Wilby | Away - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | W 21-1 | |
| Mon., 4/24 | V Girls Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/25 | FR Baseball | Torrington | Home - Veterans Memorial Park-Veterans Park [Directions] | 3:45 p.m. | L 7-2 | |
| Tue., 4/25 | V Boys Outdoor Track | Derby, Crosby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 17-8 | |
| Tue., 4/25 | V Girls Outdoor Track | Derby, Crosby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | ||
| Tue., 4/25 | V Softball | St. Paul Catholic | Home - Watertown High-Softball Field [Directions] | 3:00 p.m. | W 2-0 | |
| Tue., 4/25 | JV Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | 3:30 p.m. | ||
| Wed., 4/26 | V Baseball | Kennedy | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | W 5-4 | |
| Wed., 4/26 | V Boys Golf | St. Paul Catholic | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | Wat 190 - St. P 213 Medalist: Matt Downes 40 | |
| Wed., 4/26 | V Boys Lacrosse | Capital Prep | Away - Capital Preparatory Magnet School-Quirk MS [Directions] | 4:30 p.m. | W 15-2 | |
| Wed., 4/26 | V Boys Tennis | Kennedy | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Wed., 4/26 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Fri., 4/28 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 4:30 p.m. | L 9-2 | |
| Fri., 4/28 | V Softball | Torrington | Away - Torrington HS-THS Varsity Softball Field [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 4/28 | V Softball | Torrington | Away - Torrington HS-THS Varsity Softball Field [Directions] | Canceled | Cancelled | |
| Fri., 4/28 | V Girls Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 4/28 | V Girls Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 5:30 p.m. | W 7-0 | |
| Sat., 4/29 | V Boys Lacrosse | Pomperaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 9:00 a.m. | L 8-11 | |
| Sat., 4/29 | V Boys Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Sat., 4/29 | V Girls Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Mon., 5/1 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | Postponed | ||
| Mon., 5/1 | V Boys Golf | Holy Cross | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Mon., 5/1 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 4:30 p.m. | W 15-7 | |
| Mon., 5/1 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | L 2-3 | |
| Mon., 5/1 | V Girls Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:30 p.m. | W 18-10 | |
| Mon., 5/1 | JV Girls Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | ||
| Mon., 5/1 | V Softball | Naugatuck | Home - Watertown High-Softball Field [Directions] | 5:00 p.m. | W 4-1 | |
| Mon., 5/1 | V Girls Tennis | Naugatuck | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/2 | JV Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:30 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | Oxford, WCA | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Oxford, WCA | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Wed., 5/3 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 5/3 | V Softball | Wolcott | Away - Wolcott HS-Softball Field [Directions] | 5:00 p.m. | L 4-2 | |
| Thu., 5/4 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 4:00 p.m. | L 11-3 | |
| Thu., 5/4 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | ||
| Thu., 5/4 | V Boys Lacrosse | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 21-9 | |
| Thu., 5/4 | V Boys Tennis | Wolcott | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 5/4 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 6:45 p.m. | L 17-13 | |
| Thu., 5/4 | V Softball | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 3:30 p.m. | W 20-1 | |
| Thu., 5/4 | V Girls Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | L 3-4 | |
| Fri., 5/5 | V Baseball | Holy Cross | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 14-2 | |
| Fri., 5/5 | V Boys Tennis | Holy Cross | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 2:30 p.m. | W 5-0 | |
| Fri., 5/5 | V Softball | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 3:00 p.m. | W 7-1 | |
| Sat., 5/6 | JV Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | L 6-0 | |
| Sat., 5/6 | V Boys Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 10:00 a.m. | W 10-9 | |
| Sat., 5/6 | JV Boys Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 11:30 a.m. | ||
| Sat., 5/6 | V Boys Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Mon., 5/8 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 4:00 p.m. | L 13-6 | |
| Mon., 5/8 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 5/8 | V Boys Lacrosse | Capital Prep | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 16-1 | |
| Mon., 5/8 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 | |
| Mon., 5/8 | V Girls Lacrosse | Cromwell | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:30 p.m. | W 18-12 | |
| Mon., 5/8 | JV Girls Lacrosse | Cromwell | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:45 p.m. | ||
| Mon., 5/8 | V Softball | Oxford | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 2-1 | |
| Mon., 5/8 | V Girls Tennis | Holy Cross | Away - Wilby HS [Directions] | 4:30 p.m. | L 3-4 | |
| Tue., 5/9 | V Boys Golf | Woodland | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Tue., 5/9 | V Boys Lacrosse | Vinal-Goodwin | Away - Vinal Tech-Lacrosse Field 1 [Directions] | 3:45 p.m. | W 12-3 | |
| Tue., 5/9 | V Boys Outdoor Track | Kennedy, Torrington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Holy Cross | Home - Holy Cross-Tennis Courts [Directions] | 2:45 p.m. | L 2-3 | |
| Tue., 5/9 | V Girls Outdoor Track | Kennedy, Torrington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Wed., 5/10 | V Boys Tennis | Crosby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Wed., 5/10 | V Girls Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:15 p.m. | L 3-17 | |
| Wed., 5/10 | JV Girls Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 3:30 p.m. | ||
| Thu., 5/11 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 3:30 p.m. | L 19-0 | |
| Thu., 5/11 | FR Baseball | Wolcott | Away - BAW B Field Salerno-BAW - B Field [Directions] | Canceled | Cancelled | |
| Thu., 5/11 | V Boys Lacrosse | Litchfield Coop | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:30 p.m. | W 18-4 | |
| Thu., 5/11 | V Boys Outdoor Track | Woodland, Holy Cross | Away - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | L 2-3 | |
| Thu., 5/11 | V Girls Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 5:00 p.m. | W 15-4 | |
| Thu., 5/11 | JV Girls Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Softball Field [Directions] | Postponed | ||
| Thu., 5/11 | V Girls Outdoor Track | Woodland, Holy Cross | Away - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Thu., 5/11 | V Softball | Wolcott | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 6-0 | |
| Thu., 5/11 | V Girls Tennis | Wolcott | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 5/12 | JV Baseball | Wolcott | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 16-3 | |
| Sat., 5/13 | JV Baseball | Wamogo | Home - Deland Field-Deland field [Directions] | 10:00 a.m. | Cancelled | |
| Mon., 5/15 | V Baseball | St. Paul Catholic | Home - Deland Field-Deland field [Directions] | 4:45 p.m. | L 18-6 | |
| Mon., 5/15 | V Boys Golf | Torrington | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Mon., 5/15 | V Boys Outdoor Track | Naugatuck, Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 1-3 | |
| Mon., 5/15 | V Girls Outdoor Track | Naugatuck, Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | 3:45 p.m. | W 12-11 | |
| Mon., 5/15 | V Girls Tennis | St. Paul Catholic | Away - Page Park -Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Tue., 5/16 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 6:00 p.m. | L 11-1 | |
| Tue., 5/16 | JV Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 3:00 p.m. | ||
| Tue., 5/16 | V Boys Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 5/16 | V Girls Lacrosse | Housatonic Regional | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 16-15 | |
| Tue., 5/16 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | W 14-0 | |
| Wed., 5/17 | V Boys Golf | Holy Cross, St. Paul Catholic | Away - Western Hills Golf Course (Wtby) [Directions] | 2:15 p.m. | ||
| Wed., 5/17 | V Boys Lacrosse | Holy Cross | Away - Holy Cross-Municipal Stadium [Directions] | 6:00 p.m. | W 16-4 | |
| Wed., 5/17 | V Girls Lacrosse | Housatonic Regional | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 5/18 | JV Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 6:00 p.m. | ||
| Wed., 5/24 | V Boys Golf | Waterbury Coop | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Tue., 5/30 | V Boys Golf | Seymour, Oxford | Away - Seymour HS-Oxford Greens [Directions] | 2:00 p.m. | ||