| Watertown 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 579 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/23 | V Football | Plainville, Holy Cross (Scrim.) | Away - Plainville HS-Plainville HS- Tinty Field and Track [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | V Football | Oxford (Scrim.) | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 5:00 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Thomaston (Scrim.) | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Nonnewaug, Immaculate, Suffield (Scrim.) | Away - Nonnewaug HS-Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | V Field Hockey | Farmington Field Hockey Play-Day | Away - Farmington HS-Turf Field | 10:00 a.m. | ||
| Tue., 9/5 | V Boys Soccer | Northwestern (Scrim.) | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | JV Boys Soccer | Northwestern (Scrim.) | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/8 | V Football | Seymour | Home - Nonnewaug HS-Nonnewaug [Directions] | 8:00 p.m. | L 13-26 | |
| Sat., 9/9 | JV Football | Seymour | Away - Seymour HS-turf field [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | V Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 2:00 p.m. | L 0-1 | |
| Sat., 9/9 | V Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 10:00 a.m. | L 0-1 | |
| Sat., 9/9 | JV Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | Canceled | Cancelled | |
| Sat., 9/9 | V Girls Soccer | Naugatuck | Home - Swift MS-Soccer Field [Directions] | 1:00 p.m. | W 9-1 | |
| Mon., 9/11 | JV Boys Soccer | Naugatuck | Away - Rotary Field-Soccer Field [Directions] | Postponed | ||
| Mon., 9/11 | JV Girls Soccer | Naugatuck | Home - Veterans Memorial Park-Veterans Park Field #2 [Directions] | Canceled | Cancelled | |
| Tue., 9/12 | V Boys Cross Country | Holy Cross, St. Paul Catholic, Woodland | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 4:45 p.m. | ||
| Tue., 9/12 | V Boys Soccer | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 0-1 | |
| Tue., 9/12 | V Girls Cross Country | Holy Cross, St. Paul Catholic, Woodland | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 4:45 p.m. | ||
| Tue., 9/12 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | L 2-3 | |
| Tue., 9/12 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | Postponed | ||
| Wed., 9/13 | V Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | L 0-1 | |
| Wed., 9/13 | JV Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Thu., 9/14 | V Boys Soccer | Crosby | Home - Swift MS-Soccer Field [Directions] | 4:45 p.m. | W 7-0 | |
| Thu., 9/14 | V Girls Volleyball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Thu., 9/14 | JV Girls Volleyball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:45 p.m. | ||
| Fri., 9/15 | V Football | Wilby | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | W 41-6 | |
| Fri., 9/15 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/15 | JV Field Hockey | Nonnewaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Fri., 9/15 | V Girls Swimming and Diving | Kennedy | Away - J F Kennedy HS Turf-John Reardon Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/15 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:45 p.m. | ||
| Sat., 9/16 | FM Football | Wilby | Away - Wilby HS-Football Field [Directions] | 11:00 a.m. | ||
| Sat., 9/16 | JV Boys Soccer | Crosby | Home - Swift MS-Soccer Field [Directions] | 1:00 p.m. | ||
| Mon., 9/18 | V Girls Volleyball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Mon., 9/18 | JV Girls Volleyball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:45 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Derby, Naugatuck | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Derby, Naugatuck | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Field Hockey | Thomaston | Away - Thomaston HS-Field Hockey Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 9/19 | JV Field Hockey | Thomaston | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Tue., 9/19 | V Girls Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Volleyball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Tue., 9/19 | JV Girls Volleyball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Wed., 9/20 | V Boys Soccer | Wilby | Home - Swift MS-Soccer Field [Directions] | 4:30 p.m. | W 4-0 | |
| Wed., 9/20 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 9/21 | V Girls Soccer | Seymour | Home - Swift MS-Soccer Field [Directions] | 4:15 p.m. | W 4-0 | |
| Thu., 9/21 | JV Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | Canceled | Cancelled | |
| Thu., 9/21 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | ||
| Fri., 9/22 | V Football | Ansonia | Home - Nonnewaug HS-Nonnewaug [Directions] | 7:00 p.m. | L 7-42 | |
| Fri., 9/22 | V Boys Soccer | Seymour | Away - Seymour HS-turf field [Directions] | 6:00 p.m. | W 0-1 | |
| Fri., 9/22 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 3:30 p.m. | W 8-1 | |
| Fri., 9/22 | JV Girls Soccer | Seymour | Home - Veterans Memorial Park-Veterans Park Field #2 [Directions] | 3:30 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/22 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | ||
| Sat., 9/23 | JV Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:30 p.m. | ||
| Sat., 9/23 | V Girls Soccer | Weston | Home - Swift MS-Swift MS [Directions] | 12:00 p.m. | W 1-0 | |
| Sat., 9/23 | JV Girls Soccer | Weston | Home - Swift MS-Soccer Field [Directions] | 2:00 p.m. | ||
| Tue., 9/26 | V Boys Cross Country | Oxford, Kennedy, Wilby | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 3:15 p.m. | W 0-2 | |
| Tue., 9/26 | V Girls Cross Country | Oxford, Kennedy, Wilby | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Girls Soccer | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | L 1-2 | |
| Tue., 9/26 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby HS-Gil Cyr Natatorium [Directions] | 3:45 p.m. | Win 73-67 | |
| Tue., 9/26 | V Girls Volleyball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/26 | JV Girls Volleyball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Wed., 9/27 | JV Boys Soccer | Kennedy | Home - Veterans Memorial Park-Veterans Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 3-1 | |
| Wed., 9/27 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | Canceled | Cancelled | |
| Thu., 9/28 | V Girls Swimming and Diving | Oxford | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Thu., 9/28 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | L 2-3 | |
| Thu., 9/28 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 9/29 | V Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 7:00 p.m. | L 7-35 | |
| Fri., 9/29 | V Girls Volleyball | Derby | Away - Derby MS-DMS Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Fri., 9/29 | JV Girls Volleyball | Derby | Away - Derby MS-DMS Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | FR Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 10:00 a.m. | ||
| Sat., 9/30 | V Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 12:00 p.m. | L 2-1 | |
| Sat., 9/30 | JV Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 2:00 p.m. | ||
| Sat., 9/30 | V Field Hockey | Brookfield | Home - Watertown High-Swift middle turf field [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 9/30 | JV Girls Soccer | Thomaston | Home - Swift MS-Soccer Field [Directions] | 12:00 p.m. | ||
| Mon., 10/2 | V Girls Soccer | Woodland | Home - Municipal stadium [Directions] | 6:30 p.m. | L 0-4 | |
| Tue., 10/3 | V Boys Cross Country | Crosby, Seymour, Wolcott | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Crosby, Seymour, Wolcott | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | JV Girls Soccer | Woodland | Home - Veterans Memorial Park-Veterans Park Field #2 [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/3 | JV Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 10/4 | V Boys Soccer | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:45 p.m. | W 1-4 | |
| Wed., 10/4 | V Girls Soccer | Ansonia | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 10/5 | V Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 10/5 | V Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 7:00 p.m. | W 7-0 | |
| Thu., 10/5 | V Girls Swimming and Diving | Seymour | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | ||
| Thu., 10/5 | V Girls Volleyball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | L 1-3 | |
| Thu., 10/5 | JV Girls Volleyball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/6 | V Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:00 p.m. | W 1-2 | |
| Fri., 10/6 | V Field Hockey | Nonnewaug | Home - Swift MS-Swift MS [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 10/6 | V Girls Volleyball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Fri., 10/6 | JV Girls Volleyball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Sat., 10/7 | V Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 10:00 a.m. | W 28-0 | |
| Sat., 10/7 | V Boys Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | L 2-0 | |
| Sat., 10/7 | JV Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | V Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 3:00 p.m. | T 1-1 | |
| Sat., 10/7 | JV Girls Soccer | Torrington | Home - Veterans Memorial Park-Vets #1 [Directions] | 10:00 a.m. | ||
| Mon., 10/9 | FM Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:45 p.m. | ||
| Mon., 10/9 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 10/9 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 4:15 p.m. | ||
| Mon., 10/9 | FR Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 2:30 p.m. | ||
| Tue., 10/10 | V Boys Cross Country | Torrington, WCA | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | T 1-1 | |
| Tue., 10/10 | V Girls Cross Country | Torrington, WCA | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Girls Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/10 | V Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/10 | JV Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 4:45 p.m. | ||
| Wed., 10/11 | JV Boys Soccer | Wolcott | Home - Veterans Memorial Park-Veterans Park [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | V Boys Soccer | Derby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 5-1 | |
| Thu., 10/12 | V Girls Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 6:00 p.m. | W 7-1 | |
| Thu., 10/12 | V Girls Volleyball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/12 | JV Girls Volleyball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Fri., 10/13 | V Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/13 | JV Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Fri., 10/13 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 3:00 p.m. | W 5-1 | |
| Fri., 10/13 | V Girls Swimming and Diving | Naugatuck | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | ||
| Sat., 10/14 | FR Girls Volleyball | Woodland, Naugatuck, St. Paul Catholic | Away - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/16 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:00 p.m. | T 3-3 | |
| Mon., 10/16 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:00 p.m. | L 0-5 | |
| Mon., 10/16 | V Girls Soccer | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 6-1 | |
| Tue., 10/17 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:30 p.m. | ||
| Tue., 10/17 | JV Field Hockey | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | Canceled | Cancelled | |
| Tue., 10/17 | JV Girls Soccer | St. Paul Catholic | Home - Veterans Memorial Park-Veterans Park Field #2 [Directions] | Canceled | Cancelled | |
| Tue., 10/17 | V Girls Volleyball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 10/17 | JV Girls Volleyball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Wed., 10/18 | V Boys Soccer | Oxford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-4 | |
| Wed., 10/18 | V Field Hockey | Thomaston | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:45 p.m. | W 3-0 | |
| Wed., 10/18 | JV Field Hockey | Thomaston | Away - Thomaston HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 10/18 | V Girls Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 4-0 | |
| Wed., 10/18 | V Girls Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | ||
| Thu., 10/19 | V Field Hockey | Northwestern | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | T 0-0 | |
| Thu., 10/19 | JV Girls Soccer | Torrington | Home - Veterans Memorial Park-Veterans Park Field #2 [Directions] | 3:45 p.m. | ||
| Thu., 10/19 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Thu., 10/19 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/20 | V Football | Gilbert/Northwestern/Housy | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 12-7 | |
| Fri., 10/20 | JV Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Girls Volleyball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 10/20 | JV Girls Volleyball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:45 p.m. | ||
| Sat., 10/21 | JV Football | Gilbert/Northwestern/Housy | Away - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 10:00 a.m. | ||
| Mon., 10/23 | V Boys Soccer | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 2:45 p.m. | L 2-0 | |
| Mon., 10/23 | V Girls Soccer | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 1-0 | |
| Mon., 10/23 | V Girls Volleyball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/23 | JV Girls Volleyball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Tue., 10/24 | V Field Hockey | Litchfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 6-0 | |
| Tue., 10/24 | JV Field Hockey | Litchfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Tue., 10/24 | JV Girls Soccer | Holy Cross | Home - Watertown High-John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | ||
| Wed., 10/25 | V Boys Soccer | Woodland | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 2-0 | |
| Wed., 10/25 | V Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | L 1-2 | |
| Wed., 10/25 | V Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 5:45 p.m. | L 0-3 | |
| Wed., 10/25 | JV Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 4:45 p.m. | ||
| Wed., 10/25 | FR Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 10/26 | JV Boys Soccer | Woodland | Home - Veterans Memorial Park-Veterans Park [Directions] | 3:30 p.m. | ||
| Thu., 10/26 | JV Girls Soccer | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 10/27 | V Football | Woodland | Away - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | L 27-36 | |
| Fri., 10/27 | FR Boys Soccer | Pomperaug | Away - Pomperaug HS-PHS Soccer Field [Directions] | 3:15 p.m. | ||
| Fri., 10/27 | V Field Hockey | Wamogo | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:30 p.m. | L 1-4 | |
| Fri., 10/27 | JV Field Hockey | Wamogo | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class M Championship | Away - Wickham Park | 11:55 a.m. | ||
| Sat., 10/28 | FM Football | Woodland | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 9:30 a.m. | ||
| Sat., 10/28 | V Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 1:00 p.m. | W 2-3 | |
| Sat., 10/28 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park | 10:10 a.m. | ||
| Sat., 10/28 | V Girls Soccer | Oxford | Home - Watertown HS [Directions] | 12:00 p.m. | W 7-2 | |
| Mon., 10/30 | V Boys Soccer | Wolcott | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | L 0-2 | |
| Mon., 10/30 | V Girls Soccer | Holy Cross | Away - Wolcott HS-Turf Field [Directions] | 7:30 p.m. | W 2-1 | |
| Wed., 11/1 | V Girls Soccer | Woodland | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | St. Paul/Lewis Mills, Kennedy, TBA, Naugatuck, Oxford, Seymour, Woodland | Away - Woodland HS-pool | 6:00 p.m. | ||
| Fri., 11/3 | V Football | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 27-28 | |
| Fri., 11/3 | V Girls Swimming and Diving | St. Paul/Lewis Mills, Kennedy, Naugatuck, Oxford, Seymour, Wilby/Kaynor Tech/WCA, Woodland | Away - John F. Kennedy HS-JFK Pool | 4:30 p.m. | ||
| Sat., 11/4 | FM Football | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Branford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 11/7 | V Boys Soccer | Lewis Mills | Away - Nassahegan Recreation Complex-Nassahegan Field [Directions] | 4:00 p.m. | ||
| Tue., 11/7 | V Field Hockey | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 11/8 | V Girls Soccer | RHAM | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:30 p.m. | ||
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Fri., 11/10 | V Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | W 35-0 | |
| Sat., 11/11 | FM Football | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:15 p.m. | ||
| Wed., 11/15 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/16 | FM Football | Torrington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Thu., 11/23 | V Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:15 a.m. | W 28-8 | |
| Tue., 11/28 | V Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 6:30 p.m. | W 26-12 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Sat., 12/2 | V Boys Ice Hockey | New Milford (Scrim.) | Home - Taft School-Mays [Directions] | 7:30 p.m. | ||
| Sun., 12/3 | V Football | Gilbert/Northwestern/Housy | Away - Torrington HS [Directions] | 12:30 p.m. | W 21-0 | |
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Mon., 12/4 | V Boys Ice Hockey | St. Joseph (Scrim.) | Away - Sports Center of Connecticut-Lower [Directions] | 2:30 p.m. | ||
| Tue., 12/5 | V Boys Basketball | Wamogo (Scrim.) | Away - Wamogo HS-Wamogo Small Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/5 | V Girls Basketball | Berlin (Scrim.) | Away - Berlin HS-Gibney Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 12/6 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats (Scrim.) | Home - Taft School-Mays [Directions] | 7:45 p.m. | ||
| Fri., 12/8 | V Boys Basketball | Thomaston (Scrim.) | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/9 | V Football | Joel Barlow | Away - Rentschler Field [Directions] | 4:30 p.m. | L 20-21 | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Newington-Red Rink [Directions] | 7:00 p.m. | W 6-1 | |
| Mon., 12/11 | V Boys Basketball | Northwestern (Scrim.) | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:45 p.m. | ||
| Tue., 12/12 | V Girls Basketball | Ansonia | Home - Watertown HS [Directions] | 7:00 p.m. | L 41-49 | |
| Tue., 12/12 | JV Girls Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/13 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Taft School-Mays [Directions] | 7:45 p.m. | W 4-0 | |
| Wed., 12/13 | V Wrestling | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:00 p.m. | New Milford 72 Pomperaug Co-op 10 | |
| Wed., 12/13 | V Girls Ice Hockey | Suffield Coop | Home - Newington-Red Rink [Directions] | 8:30 p.m. | W 3-1 | |
| Fri., 12/15 | V Boys Basketball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 45-93 | |
| Fri., 12/15 | JV Boys Basketball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/15 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:30 p.m. | L 52-54 | |
| Fri., 12/15 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 12/16 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 8:15 p.m. | L 2-5 | |
| Sat., 12/16 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 4:15 p.m. | L 0-2 | |
| Tue., 12/19 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 53-86 | |
| Tue., 12/19 | JV Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 12/19 | FR Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 12/19 | V Girls Basketball | Torrington | Home - Watertown HS [Directions] | 6:00 p.m. | W 56-40 | |
| Tue., 12/19 | JV Girls Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Tue., 12/19 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 7:20 p.m. | L 0-5 | |
| Wed., 12/20 | V Boys Ice Hockey | South Windsor | Home - Taft School-Mays [Directions] | 7:45 p.m. | L 2-3 | |
| Wed., 12/20 | V Boys Swimming and Diving | Litchfield | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | ||
| Wed., 12/20 | V Wrestling | New Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 21 New Fairfield 55 | |
| Wed., 12/20 | V Girls Ice Hockey | Hall/Conard | Home - Newington-Red Rink [Directions] | 5:10 p.m. | W 3-0 | |
| Fri., 12/22 | V Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 67-92 | |
| Fri., 12/22 | JV Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/22 | FR Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Holy Cross | Home - Watertown HS [Directions] | 6:00 p.m. | L 36-63 | |
| Fri., 12/22 | JV Girls Basketball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Sat., 12/23 | FR Boys Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 12:30 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | North Branford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-2 | |
| Sat., 12/23 | V Wrestling | Nonnewaug, St. Paul Catholic, Terryville-Thomaston (2 mats) | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | Pomperaug 31 Nonnewaug 47 Pomperaug 55 St. Paul 12 Pomperaug 48 Terryville-Thomaston 30 | |
| Wed., 12/27 | V Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:00 p.m. | W 41-33 | |
| Wed., 12/27 | JV Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:15 p.m. | ||
| Wed., 12/27 | FR Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 1:30 p.m. | ||
| Wed., 12/27 | V Boys Ice Hockey | North Haven | Home - Taft School-Mays [Directions] | 7:45 p.m. | L 3-4 OT | |
| Wed., 12/27 | V Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | W 65-42 | |
| Wed., 12/27 | JV Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | Postponed | ||
| Wed., 12/27 | FR Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 12/28 | V Girls Basketball | Bristol Eastern | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | W 60-50 | |
| Fri., 12/29 | V Boys Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 44-67 | |
| Fri., 12/29 | JV Boys Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/29 | FR Boys Basketball | Thomaston | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/30 | V Boys Ice Hockey | Daniel Hand | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 3-2 | |
| Sat., 12/30 | V Wrestling | Trumbull Duals (6 mats) | Away - Trumbull HS-McDougall Stadium | 9:00 a.m. | Pomperaug 15 Trumbull 66 Pomperaug 6 NFA 75 Pomperaug 18 Manchester 66 Pomperaug 36 Masuk 33 Pomperaug 42 JV All-Stars 39 | |
| Sat., 12/30 | JV Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | 6:10 p.m. | ||
| Tue., 1/2 | FR Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 1/3 | V Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 61-95 | |
| Wed., 1/3 | JV Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms-Jennings Rink [Directions] | 7:30 p.m. | W 4-1 | |
| Wed., 1/3 | V Wrestling | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:00 p.m. | Pomperaug 48 Bethel 27 | |
| Wed., 1/3 | V Girls Basketball | Wilby | Home - Watertown HS [Directions] | 6:00 p.m. | W 54-31 | |
| Wed., 1/3 | JV Girls Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/3 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Lower Rink [Directions] | 8:40 p.m. | L 2-1 | |
| Fri., 1/5 | V Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:30 p.m. | L 52-70 | |
| Fri., 1/5 | JV Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Fri., 1/5 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks-Rink 2 [Directions] | 7:50 p.m. | W 4-1 | |
| Fri., 1/5 | V Boys Swimming and Diving | Crosby/WCA | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Woodland | Home - Watertown HS [Directions] | 6:00 p.m. | W 56-51 | |
| Fri., 1/5 | JV Girls Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/5 | JV Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks-Rink 1 [Directions] | 9:20 p.m. | ||
| Sat., 1/6 | V Boys Ice Hockey | Hamden | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:15 p.m. | W 4-1 | |
| Sat., 1/6 | V Wrestling | Bristol Central Invitational | Away - Bristol Central HS-Charles C. Marsh Gymnasium | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 1/6 | JV Wrestling | Bristol Eastern, Avon, Berlin, Branford, Bristol Central, East Hartford, Enfield, Farmington, Guilford, Ledyard, Middletown, New Fairfield, New Milford, Plainville, Ridgefield, Staples, Terryville-Thomaston, Wethersfield, Hall | Away - Bristol Eastern HS-Gym | 9:00 a.m. | ||
| Tue., 1/9 | JV Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/10 | V Boys Ice Hockey | Eastern CT Eagles | Home - Taft School-Mays [Directions] | 7:45 p.m. | W 5-2 | |
| Wed., 1/10 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:15 p.m. | L 48-74 | |
| Wed., 1/10 | V Girls Ice Hockey | Simsbury | Home - Newington-Red Rink [Directions] | 5:10 p.m. | W 4-3 | |
| Thu., 1/11 | V Boys Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 69-56 | |
| Thu., 1/11 | JV Boys Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/11 | V Wrestling | Joel Barlow | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 42 Joel Barlow 27 | |
| Fri., 1/12 | V Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 62-42 | |
| Fri., 1/12 | JV Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | V Boys Swimming and Diving | Woodland | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 6:00 p.m. | L 39-54 | |
| Fri., 1/12 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 1/12 | V Girls Gymnastics | New Milford, Brookfield, Danbury, Joel Barlow, Newtown | Away - New Milford HS-Small Gym - NMHS | 6:30 p.m. | ||
| Fri., 1/12 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 7:10 p.m. | L 6-3 | |
| Fri., 1/12 | JV Girls Ice Hockey | Suffield Coop | Home - Newington-Red Rink [Directions] | 4:30 p.m. | ||
| Sat., 1/13 | FR Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 12:30 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | Branford | Away - Northford-Red [Directions] | 2:30 p.m. | W 3-2 OT | |
| Sat., 1/13 | V Wrestling | Art Powers Dual (4 mats) | Away - Berlin HS-Jim Day Gymnasium | 9:30 a.m. | Pomperaug 16 RHAM 63 Pomperaug 24 Bristol Central 54 Pomperaug Bradford 51 Pomperaug 19 Pomperaug 33 Montville 42 | |
| Sat., 1/13 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | 7:30 p.m. | L 3-2 | |
| Mon., 1/15 | V Girls Ice Hockey | Darien | Home - Newington-Red Rink [Directions] | 4:00 p.m. | L 5-1 | |
| Tue., 1/16 | JV Girls Basketball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/17 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 58-60 | |
| Wed., 1/17 | JV Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 1/17 | V Wrestling | Notre Dame-Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 72 Notre-Dame Fairfield 12 | |
| Wed., 1/17 | V Girls Basketball | Kennedy | Home - Watertown HS [Directions] | 6:00 p.m. | W 64-63 | |
| Wed., 1/17 | V Girls Ice Hockey | East Catholic Coop | Home - Newington-Red Rink [Directions] | 5:10 p.m. | L 3-1 | |
| Fri., 1/19 | V Boys Basketball | Derby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 41-46 | |
| Fri., 1/19 | JV Boys Basketball | Derby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 6:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:30 p.m. | W 62-41 | |
| Fri., 1/19 | V Girls Ice Hockey | West Haven/SHA | Home - Newington-Red Rink [Directions] | 4:30 p.m. | W 3-1 | |
| Fri., 1/19 | JV Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 8:30 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | Lyman Hall | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 5-1 | |
| Sat., 1/20 | V Wrestling | New Milford, Amity, Bethel, Bunnell, Enfield, Joel Barlow, Maloney, Masuk, Norwalk, RHAM, Stratford, Terryville-Thomaston, Harding/Bassick/Bridgeport Central, Weston | Away - New Milford HS-Main Gym - NMHS | 9:00 a.m. | ||
| Sat., 1/20 | V Girls Gymnastics | Newtown, Oxford, Pomperaug | Away - Newtown Gymnastics [Directions] | 4:00 p.m. | ||
| Sat., 1/20 | V Girls Ice Hockey | Longmeadow (MA) | Home - Newington-Red Rink [Directions] | 5:50 p.m. | ||
| Mon., 1/22 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:00 p.m. | L 58-55 | |
| Mon., 1/22 | JV Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | Postponed | ||
| Tue., 1/23 | JV Girls Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/24 | V Wrestling | Weston | Away - Weston HS-Gym (Old) [Directions] | 6:00 p.m. | Pomperaug 24 Weston 54 | |
| Wed., 1/24 | V Girls Ice Hockey | Suffield Coop | Away - Simsbury - ISCC-Olympic [Directions] | 7:00 p.m. | L 1-0 | |
| Wed., 1/24 | JV Girls Ice Hockey | JV vs Pope Francis at Snead Arena, Springfield | Away - [CIAC] Site TBA | 7:30 p.m. | ||
| Thu., 1/25 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 44-84 | |
| Thu., 1/25 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 1/25 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 1/25 | V Girls Basketball | Naugatuck | Home - Watertown HS [Directions] | 6:00 p.m. | W 53- 41 | |
| Fri., 1/26 | V Boys Basketball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 42-92 | |
| Fri., 1/26 | JV Boys Basketball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/26 | V Boys Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Torrington | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | W 56-26 | |
| Fri., 1/26 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Canceled | Cancelled | |
| Fri., 1/26 | V Girls Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Sat., 1/27 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 2:00 p.m. | ||
| Sat., 1/27 | V Boys Ice Hockey | Conard | Home - Taft School-Mays [Directions] | 7:30 p.m. | T 1-1 | |
| Sat., 1/27 | V Boys Indoor Track | Jack Long Invite | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Sat., 1/27 | V Wrestling | Brookfield Invitational | Away - Brookfield HS-BHS Small & Big Gym | 9:30 a.m. | ||
| Sat., 1/27 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 5:30 p.m. | W 3-2 | |
| Sat., 1/27 | V Girls Indoor Track | Jack Long Invite | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Mon., 1/29 | V Girls Gymnastics | New Milford, Brookfield, Danbury, Newtown | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:30 p.m. | ||
| Tue., 1/30 | V Boys Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | ||
| Tue., 1/30 | JV Boys Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 5:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Seymour | Away - Seymour MS-Gym 1 [Directions] | 6:00 p.m. | W 64-57 | |
| Tue., 1/30 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/31 | V Wrestling | Brookfield/Shepaug | Away - Brookfield HS-BHS Big Gym [Directions] | 6:00 p.m. | Pomperaug 18 Brookfield 54 | |
| Wed., 1/31 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | L 3-2 | |
| Fri., 2/2 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 2/2 | V Girls Ice Hockey | Narragansett (RI) (Scrim.) | Home - Newington-Blue Rink [Directions] | 7:00 p.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | JBWA | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | W 4-2 | |
| Sat., 2/3 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Newington-Blue Rink [Directions] | 5:35 p.m. | W 7-1 | |
| Mon., 2/5 | V Wrestling | Stratford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 18 Stratford 47 | |
| Tue., 2/6 | V Boys Swimming and Diving | Holy Cross | Home - Watertown HS-Pool [Directions] | 6:30 p.m. | ||
| Wed., 2/7 | V Boys Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/7 | JV Boys Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/7 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 2-4 | |
| Wed., 2/7 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:00 p.m. | L 49-45 | |
| Wed., 2/7 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 2/7 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Newington-Red Rink [Directions] | 5:10 p.m. | W 2-1 | |
| Thu., 2/8 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 2/8 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 3:00 p.m. | ||
| Thu., 2/8 | Unified Sports Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 12:15 p.m. | ||
| Fri., 2/9 | V Boys Ice Hockey | Guilford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-2 | |
| Fri., 2/9 | V Boys Swimming and Diving | Oxford | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 2/9 | V Girls Gymnastics | SWC Gymnastics Championships | Away - New Milford HS-Main Gym - NMHS | 5:00 p.m. | ||
| Fri., 2/9 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 6-4 | |
| Fri., 2/9 | V Girls Indoor Track | CIAC S Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 2/10 | V Boys Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/10 | JV Boys Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/10 | FR Boys Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC M Divisional Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/10 | V Wrestling | SWC Wrestling Championships at Newtown High School | Away - Newtown HS-Gym | 9:00 a.m. | ||
| Sat., 2/10 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 6:00 p.m. | W 6-2 | |
| Mon., 2/12 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 2/12 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:15 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Oxford | Home - Watertown HS [Directions] | 6:00 p.m. | L 46-58 | |
| Mon., 2/12 | JV Girls Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/14 | V Boys Ice Hockey | East Haven Coop | Home - Taft School-Mays [Directions] | 7:45 p.m. | L 0-3 | |
| Wed., 2/14 | V Girls Basketball | Wolcott | Home - Watertown HS [Directions] | 6:00 p.m. | W 59-52 | |
| Wed., 2/14 | JV Girls Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/14 | V Girls Ice Hockey | Simsbury | Away - Simsbury - ISCC-NHL [Directions] | 6:10 p.m. | W 6-2 | |
| Thu., 2/15 | V Girls Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 72- 40 | |
| Fri., 2/16 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/16 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/16 | V Boys Swimming and Diving | Kennedy | Away - John F. Kennedy HS-JFK Pool [Directions] | 4:45 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | ||
| Fri., 2/16 | JV Girls Ice Hockey | East Catholic Coop | Home - Newington-Red Rink [Directions] | 4:30 p.m. | ||
| Sat., 2/17 | FR Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/17 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 3:00 p.m. | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Basketball | Oxford | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 2/17 | V Girls Gymnastics | Pomperaug, Hamden, Newtown, Oxford | Away - Kinetic Kids [Directions] | 5:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Girls Basketball | St. Paul Catholic | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/19 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Upper Rink [Directions] | 1:30 p.m. | ||
| Tue., 2/20 | V Boys Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | ||
| Tue., 2/20 | JV Boys Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/20 | FR Boys Basketball | Woodland | Home - Watertown HS [Directions] | 3:30 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | ||
| Fri., 2/23 | V Boys Ice Hockey | Westhill/Stamford | Home - Taft School-Mays [Directions] | 6:30 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Fri., 2/23 | V Girls Ice Hockey | East Catholic Coop | Away - Trinity College-Koeppel Community Sports Center [Directions] | 6:15 p.m. | ||
| Sat., 2/24 | V Girls Basketball | WCA (Scrim.) | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 10:30 a.m. | ||
| Mon., 2/26 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Newington-Red Rink [Directions] | 6:10 p.m. | ||
| Tue., 2/27 | V Boys Swimming and Diving | TBA, Crosby/WCA, Holy Cross, Kennedy, TBA, Oxford, Seymour, Torrington, Wilby/Kaynor | Away - Watertown HS-Frank M. Reinhold Pool | 6:00 p.m. | ||
| Tue., 2/27 | V Girls Basketball | Brookfield | Home - Watertown High-Robert B Cook Gym [Directions] | 6:30 p.m. | L 43-63 | |
| Wed., 2/28 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | ||
| Thu., 2/29 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | 4:30 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | Woodland, Crosby/WCA, Holy Cross, Kennedy, Naugatuck, Oxford, Seymour, Torrington, Wilby/Kaynor | Away - John F. Kennedy HS-JFK Pool | 4:00 p.m. | ||
| Tue., 3/5 | V Boys Ice Hockey | Hamden | Away - Hamden-Lou Astorino Ice Rink [Directions] | 7:30 p.m. | W 4-0 | |
| Tue., 3/5 | V Boys Ice Hockey | CIAC Div II First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Ice Hockey | Cheshire | Away - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | L 1-2 | |
| Fri., 3/8 | V Boys Ice Hockey | CIAC Div II Quarterfinal | Away - Site TBA | TBA | ||
| Fri., 3/8 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 5:15 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Tue., 3/12 | V Boys Ice Hockey | CIAC Div II Semifinal | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 3/18 | V Boys Ice Hockey | CIAC Div II Final | Away - Site TBA | TBA | ||
| Fri., 3/22 | V Baseball | Wamogo (Scrim.) | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Danbury (Scrim.) | Away - Danbury HS-Stadium Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 3/26 | V Girls Lacrosse | Berlin (Scrim.) | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Tue., 3/26 | V Softball | Bristol Eastern (Scrim.) | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | V Girls Tennis | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Baseball | Kaynor Tech (Scrim.) | Home - Deland Field-Deland field [Directions] | 3:30 p.m. | ||
| Sat., 3/30 | V Baseball | Kennedy | Away - Waterville Park-Baseball Field [Directions] | 11:00 a.m. | W 17-6 | |
| Sat., 3/30 | V Girls Lacrosse | Joel Barlow | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | L 17-3 | |
| Sat., 3/30 | V Softball | Kennedy | Home - Watertown High-Softball Field [Directions] | 11:00 a.m. | W 19-0 | |
| Sat., 3/30 | V Girls Tennis | Kennedy | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Mon., 4/1 | V Baseball | Woodland | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 15-3 | |
| Mon., 4/1 | V Boys Tennis | Woodland | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Mon., 4/1 | V Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | W 3-1 | |
| Mon., 4/1 | V Girls Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Tue., 4/2 | JV Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 4/2 | V Boys Outdoor Track | Torrington | Home - Watertown HS [Directions] | Postponed | ||
| Tue., 4/2 | V Girls Lacrosse | Litchfield Coop | Away - Nonnewaug HS-Nonnewaug Track [Directions] | 7:00 p.m. | W 16-1 | |
| Tue., 4/2 | V Girls Outdoor Track | Torrington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Thu., 4/4 | V Girls Lacrosse | Bristol Eastern | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 5:30 p.m. | W 13-12 | |
| Thu., 4/4 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/5 | V Boys Tennis | Holy Cross | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/5 | V Softball | Holy Cross | Home - Watertown High-Softball Field [Directions] | 4:30 p.m. | L 0-3 | |
| Fri., 4/5 | V Girls Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Sat., 4/6 | V Baseball | Ansonia | Home - Deland Field-Deland field [Directions] | 4:00 p.m. | L 11-1 | |
| Sat., 4/6 | V Girls Lacrosse | Griswold/Norwich Tech | Away - Griswold HS-Turf Field and Track [Directions] | 6:00 p.m. | W 16-13 | |
| Sat., 4/6 | JV Girls Lacrosse | Griswold/Norwich Tech | Away - Griswold HS-Soccer/Lacrosse Field [Directions] | 7:30 p.m. | ||
| Mon., 4/8 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 4:30 p.m. | L 8-3 | |
| Mon., 4/8 | V Boys Lacrosse | Lewis Mills | Away - Lewis Mills HS-JV Soccer/Lacrosse Field [Directions] | 4:00 p.m. | L 3-5 | |
| Mon., 4/8 | JV Boys Lacrosse | Lewis Mills | Away - Lewis Mills HS-JV Soccer/Lacrosse Field [Directions] | 5:30 p.m. | ||
| Mon., 4/8 | V Girls Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | W 23-13 | |
| Mon., 4/8 | V Softball | Torrington | Home - Watertown High-Softball Field [Directions] | 4:30 p.m. | W 15-0 | |
| Mon., 4/8 | V Girls Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Tue., 4/9 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 4:00 p.m. | W 11-1 | |
| Tue., 4/9 | V Boys Outdoor Track | Thomaston, St. Paul Catholic | Away - Thomaston HS-Nystrom Park [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:30 p.m. | L 1-4 | |
| Tue., 4/9 | V Girls Outdoor Track | Thomaston, St. Paul Catholic | Away - Thomaston HS-Nystrom Park [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Softball | Seymour | Home - Watertown High-Softball Field [Directions] | 3:15 p.m. | W 4-3 | |
| Wed., 4/10 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:45 p.m. | L 12-2 | |
| Wed., 4/10 | V Boys Golf | Oxford | Away - Oxford Greens [Directions] | 2:45 p.m. | ||
| Wed., 4/10 | V Boys Tennis | Southington | Away - Southington HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/10 | V Girls Tennis | Seymour | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/11 | JV Baseball | Seymour | Away - French Park-Baseball Field [Directions] | Canceled | Cancelled | |
| Thu., 4/11 | V Boys Golf | Torrington | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Thu., 4/11 | V Boys Outdoor Track | Crosby | Home - Watertown HS [Directions] | Postponed | ||
| Thu., 4/11 | V Girls Outdoor Track | Crosby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Thu., 4/11 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | 3:45 p.m. | W 16-4 | |
| Fri., 4/12 | V Baseball | Derby | Away - Payden Park [Directions] | 5:30 p.m. | W 9-1 | |
| Fri., 4/12 | V Girls Lacrosse | Shelton | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 21-7 | |
| Fri., 4/12 | JV Girls Lacrosse | Shelton | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:30 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Litchfield Coop | Away - Nonnewaug HS-football field [Directions] | 11:00 a.m. | W 14-3 | |
| Sat., 4/13 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 11:00 a.m. | W 4-1 | |
| Sat., 4/13 | V Girls Lacrosse | Middletown/Coginchaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:30 a.m. | W 19-12 | |
| Sat., 4/13 | JV Girls Lacrosse | Middletown/Coginchaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Mon., 4/15 | V Baseball | St. Paul Catholic | Home - Deland Field-Deland field [Directions] | 4:30 p.m. | L 8-1 | |
| Mon., 4/15 | V Boys Lacrosse | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 13-12 OT | |
| Mon., 4/15 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 6:00 p.m. | L 15-9 | |
| Mon., 4/15 | V Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | 4:00 p.m. | W 5-1 | |
| Mon., 4/15 | V Girls Tennis | St. Paul Catholic | Away - Page Park -Tennis Courts [Directions] | 4:30 p.m. | W 5-2 | |
| Tue., 4/16 | V Boys Outdoor Track | Kennedy, Thomaston | Home - Watertown HS [Directions] | 10:00 a.m. | ||
| Tue., 4/16 | V Girls Outdoor Track | Kennedy, Thomaston | Home - Watertown HS [Directions] | 10:00 a.m. | ||
| Tue., 4/16 | JV Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | Canceled | Cancelled | |
| Wed., 4/17 | V Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | W 6-1 | |
| Wed., 4/17 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | Postponed | ||
| Wed., 4/17 | V Boys Lacrosse | Capital Prep | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 15-1 | |
| Wed., 4/17 | V Softball | Thomaston | Home - Watertown High-Softball Field [Directions] | 1:30 p.m. | W 6-2 | |
| Wed., 4/17 | V Softball | Wilby | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 19-0 | |
| Thu., 4/18 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | Postponed | ||
| Fri., 4/19 | V Girls Lacrosse | Rockville | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:30 p.m. | T 8-8 | |
| Fri., 4/19 | V Softball | Naugatuck | Home - Watertown High-Softball Field [Directions] | 1:00 p.m. | W 5-0 | |
| Sat., 4/20 | V Boys Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 3:30 p.m. | L 1-10 | |
| Sat., 4/20 | JV Boys Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sat., 4/20 | V Boys Outdoor Track | Wildcat Relays (DO NOT DELETE) | Away - Lyme-Old Lyme HS-Track Field | 10:00 a.m. | ||
| Sat., 4/20 | V Girls Outdoor Track | Wildcat Relays (DO NOT DELETE) | Away - Lyme-Old Lyme HS-Track Field | 10:00 a.m. | ||
| Mon., 4/22 | V Baseball | Crosby | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | W 13-5 | |
| Mon., 4/22 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 4/22 | V Boys Tennis | Crosby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 4/22 | V Softball | Crosby | Home - Watertown High-Softball Field [Directions] | 4:30 p.m. | W 16-0 | |
| Mon., 4/22 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Tue., 4/23 | V Baseball | Holy Cross | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 0-17 | |
| Tue., 4/23 | V Boys Golf | Naugatuck | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Tue., 4/23 | V Boys Lacrosse | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 12-6 | |
| Tue., 4/23 | V Boys Outdoor Track | Torrington, WCA | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 2:30 a.m. | W 3-2 | |
| Tue., 4/23 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 4/23 | V Girls Outdoor Track | Torrington, WCA | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | W 11-1 | |
| Tue., 4/23 | V Girls Tennis | Wilby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 4/24 | V Baseball | Seymour | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 5-8 | |
| Wed., 4/24 | V Boys Golf | Woodland | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Naugatuck | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:30 p.m. | W 4-1 | |
| Wed., 4/24 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 3:45 p.m. | W 16-0 | |
| Wed., 4/24 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 4/25 | V Boys Golf | Holy Cross | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:00 p.m. | ||
| Thu., 4/25 | V Boys Golf | Waterbury Coop | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | L 1-4 | |
| Fri., 4/26 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | L 6-7 | |
| Fri., 4/26 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 4/26 | V Boys Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 11-0 | |
| Fri., 4/26 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | W 3-2 | |
| Fri., 4/26 | V Girls Lacrosse | Housatonic Regional | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Fri., 4/26 | V Softball | Wolcott | Away - Wolcott HS-Softball Field [Directions] | 5:15 p.m. | W 9-1 | |
| Sat., 4/27 | V Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 12:00 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 4/27 | V Girls Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/27 | JV Girls Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | Canceled | Cancelled | |
| Sat., 4/27 | V Girls Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 9:00 a.m. | ||
| Sat., 4/27 | V Girls Tennis | Wolcott | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Mon., 4/29 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | ||
| Mon., 4/29 | V Softball | WCA | Away - Municipal Stadium [Directions] | 5:00 p.m. | W 16-1 | |
| Mon., 4/29 | V Girls Tennis | Woodland | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | WCA | Home - Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | WCA | Home - Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Softball | Ansonia | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 17-5 | |
| Tue., 4/30 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Baseball | Oxford | Home - Deland Field-Deland field [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | V Boys Golf | Oxford | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | V Girls Lacrosse | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Wed., 5/1 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:45 p.m. | L 5-2 | |
| Wed., 5/1 | V Girls Tennis | Woodland (Scrim.) | Away - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/3 | V Baseball | Torrington | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | ||
| Fri., 5/3 | V Softball | St. Paul Catholic | Home - Watertown High-Softball Field [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | V Girls Tennis | St. Paul Catholic | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:30 p.m. | ||
| Sat., 5/4 | V Boys Lacrosse | Bristol Coop | Away - Bristol Central HS-BC Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 5/4 | V Boys Outdoor Track | Marty Roberts invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Mon., 5/6 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | Canceled | Cancelled | |
| Mon., 5/6 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 5/6 | V Boys Lacrosse | Capital Prep | Away - Capital Preparatory Magnet School-Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Mon., 5/6 | V Girls Lacrosse | Litchfield Coop | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Naugatuck | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | JV Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Boys Golf | Seymour | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Wilby | Home - Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Wilby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Ansonia | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | JV Girls Tennis | Ansonia | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 2:00 p.m. | ||
| Wed., 5/8 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Boys Lacrosse | Litchfield Coop | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | ||
| Wed., 5/8 | V Boys Tennis | Wolcott | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 5/9 | JV Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Thu., 5/9 | V Boys Golf | St. Paul Catholic | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Housatonic Regional | Away - Housatonic Valley Regional High-Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Softball | WCA | Home - Watertown High-Softball Field [Directions] | 5:00 p.m. | ||
| Fri., 5/10 | V Baseball | WCA | Away - Bucks Hill (MONTOE) Park-Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Boys Lacrosse | Vinal-Goodwin | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Fri., 5/10 | V Boys Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | Cancelled | |
| Sat., 5/11 | V Boys Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Sat., 5/11 | V Girls Tennis | NVL Girls Tennis - JV Jamboree | Away - Woodland HS-Tennis Courts | 10:00 a.m. | ||
| Mon., 5/13 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Boys Golf | Wolcott | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Mon., 5/13 | V Boys Lacrosse | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | Wolcott | Away - Wolcott HS-WHS Track and Lower Field [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | V Girls Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:15 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | Wolcott | Away - Wolcott HS-WHS Track and Lower Field [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Holy Cross | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/14 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:45 p.m. | ||
| Wed., 5/15 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | ||
| Wed., 5/15 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||