| Watertown 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 596 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 8/26 | V Football | Plainville, Holy Cross (Scrim.) | Away - Plainville HS-Plainville HS- Tinty Field and Track [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 8/28, Time to 10:00 a.m. | ||||||
| Thu., 9/2 | V Football | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | ||
| Sat., 9/4 | FR Football | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/4 | V Boys Soccer | Nonnewaug, East Hampton, Immaculate (Scrim.) | Away - Nonnewaug HS-Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 9/4 | V Field Hockey | Field Hockey Pre-Season Play Day | Away - Farmington HS-Turf Field | 10:00 a.m. | ||
| Tue., 9/7 | V Field Hockey | Pomperaug (Scrim.) | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | ||
| Thu., 9/9 | V Field Hockey | Litchfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | W 8-0 | |
| Thu., 9/9 | JV Field Hockey | Litchfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Thu., 9/9 | V Girls Soccer | Weston | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 1-3 | |
| Fri., 9/10 | V Football | WCA | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 22-8 | |
| Sat., 9/11 | FM Football | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | V Boys Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 11:00 a.m. | L 3-2 | |
| Sat., 9/11 | V Girls Soccer | Woodland | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | L 0-4 | |
| Mon., 9/13 | JV Boys Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 5:15 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Torrington, WCA, Wilby | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Boys Soccer | Seymour | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 2-0 | |
| Tue., 9/14 | V Girls Cross Country | Torrington, WCA, Wilby | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Girls Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | W 8-0 | |
| Tue., 9/14 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 2-3 | |
| Tue., 9/14 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/15 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 6:00 p.m. | L 0-2 | |
| Wed., 9/15 | JV Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | Canceled | Cancelled | |
| Thu., 9/16 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/17 | V Football | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 6:30 p.m. | L 7-28 | |
| Fri., 9/17 | V Boys Soccer | WCA | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | W 5-0 | |
| Fri., 9/17 | V Girls Swimming and Diving | Naugatuck | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | Naugatuck 92 Watertown 83 | |
| Fri., 9/17 | V Girls Volleyball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/17 | JV Girls Volleyball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:45 p.m. | ||
| Sat., 9/18 | V Boys Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/18 | JV Football | Woodland | Away - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FM Football | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/18 | JV Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | Canceled | Cancelled | |
| Mon., 9/20 | V Girls Soccer | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 9/21 | V Boys Cross Country | Naugatuck, Derby | Away - Hop Brook Park [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | V Boys Soccer | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 6:00 p.m. | W 7-1 | |
| Tue., 9/21 | V Girls Cross Country | Naugatuck, Derby | Away - Hop Brook Park [Directions] | 3:30 p.m. | ||
| Tue., 9/21 | V Girls Swimming and Diving | Kennedy | Away - John F. Kennedy HS-John Reardon Pool [Directions] | 5:30 p.m. | Watertown 92 Kennedy 67 | |
| Tue., 9/21 | V Girls Volleyball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 0-3 | |
| Tue., 9/21 | JV Girls Volleyball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/22 | V Field Hockey | Nonnewaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | L 0-1 | |
| Wed., 9/22 | JV Field Hockey | Nonnewaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:30 p.m. | ||
| Thu., 9/23 | V Football | Wilby | Away - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:00 p.m. | W 24-6 | |
| Thu., 9/23 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 6:30 p.m. | W 7-1 | |
| Thu., 9/23 | JV Girls Soccer | Torrington | Home - Veterans Memorial Park-Veterans Park Field #2 [Directions] | 3:45 p.m. | ||
| Fri., 9/24 | JV Field Hockey | Wamogo | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Fri., 9/24 | V Girls Soccer | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 3-1 | |
| Fri., 9/24 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | Watertown 99 St. Paul 88 | |
| Fri., 9/24 | V Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 6:30 p.m. | L 0-3 | |
| Fri., 9/24 | JV Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Sat., 9/25 | FM Football | Wilby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-Upper Soccer Field [Directions] | Postponed | ||
| Sat., 9/25 | JV Girls Soccer | Seymour | Away - Seymour HS-Seymour High Lower Field [Directions] | Canceled | Cancelled | |
| Sat., 9/25 | FR Girls Volleyball | Naugatuck, St. Paul Catholic, Woodland | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 9/27 | V Field Hockey | Wamogo | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 9/28 | V Boys Soccer | Wilby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 6-0 | |
| Tue., 9/28 | V Girls Soccer | Holy Cross | Away - Municipal Stadium-Bethel HS Track & Field Training Center [Directions] | 7:15 p.m. | L 1-5 | |
| Tue., 9/28 | V Girls Volleyball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:15 p.m. | L 0-3 | |
| Tue., 9/28 | JV Girls Volleyball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/29 | V Boys Cross Country | Wolcott, Kennedy, Oxford | Away - Bucks Hill (MONTOE) Park-Soccer Pitch [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Wolcott HS-Monroe Field | ||||||
| Wed., 9/29 | V Girls Cross Country | Wolcott, Kennedy, Oxford | Away - Bucks Hill (MONTOE) Park-Soccer Pitch [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Wolcott HS-Soccer Field | ||||||
| Wed., 9/29 | V Girls Swimming and Diving | Torrington | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | Watertown 91 Torrington 76 | |
| Thu., 9/30 | JV Boys Soccer | WCA | Home - Veterans Memorial Park-Vets #1 [Directions] | Postponed | ||
| Thu., 9/30 | V Field Hockey | Lauralton Hall | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/30 | JV Field Hockey | Lauralton Hall | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | ||
| Thu., 9/30 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:45 p.m. | W 3-0 | |
| Thu., 9/30 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 5:15 p.m. | ||
| Fri., 10/1 | V Football | Seymour | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 20-31 | |
| Fri., 10/1 | V Field Hockey | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:00 p.m. | L 0-1 | |
| Fri., 10/1 | JV Field Hockey | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 4:30 p.m. | ||
| Fri., 10/1 | V Girls Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 5:30 p.m. | ||
| Fri., 10/1 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3 to 1 | |
| Fri., 10/1 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Sat., 10/2 | FM Football | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | FR Girls Volleyball | Holy Cross, Naugatuck, Torrington | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/4 | V Boys Soccer | Kennedy | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 7-2 | |
| Tue., 10/5 | V Boys Cross Country | Crosby, Seymour, Woodland | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:00 p.m. | ||
| Tue., 10/5 | V Boys Soccer | Oxford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:30 p.m. | W 3-2 | |
| Tue., 10/5 | V Girls Cross Country | Crosby, Seymour, Woodland | Home - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:00 p.m. | ||
| Tue., 10/5 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 5:00 p.m. | W 6-0 | |
| Tue., 10/5 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | Postponed | ||
| Tue., 10/5 | JV Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 5:30 p.m. | ||
| Tue., 10/5 | V Girls Volleyball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Tue., 10/5 | JV Girls Volleyball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:00 p.m. | ||
| Wed., 10/6 | V Field Hockey | Northwestern | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 5-1 | |
| Wed., 10/6 | JV Field Hockey | Northwestern | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Canceled | Cancelled | |
| Wed., 10/6 | V Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | L 0-2 | |
| Wed., 10/6 | V Girls Volleyball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | W 3-2 | |
| Wed., 10/6 | JV Girls Volleyball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/7 | FR Football | Plainville | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Thu., 10/7 | V Girls Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 5-0 | |
| Fri., 10/8 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 4:15 p.m. | ||
| Fri., 10/8 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 10/8 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 10/8 | V Girls Swimming and Diving | Seymour | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 10/8 | V Girls Volleyball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/8 | JV Girls Volleyball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Mon., 10/11 | V Boys Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 6:15 p.m. | W 1-0 | |
| Mon., 10/11 | V Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 12:15 p.m. | L 2-0 | |
| Mon., 10/11 | JV Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Mon., 10/11 | V Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 10/11 | JV Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/12 | V Boys Cross Country | St. Paul Catholic, Holy Cross | Away - St. Paul Catholic HS-St. Paul Track [Directions] | 3:30 p.m. | ||
| Tue., 10/12 | V Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | W 4-2 | |
| Tue., 10/12 | V Girls Cross Country | St. Paul Catholic, Holy Cross | Away - St. Paul Catholic HS-St. Paul Track [Directions] | 3:30 p.m. | ||
| Tue., 10/12 | V Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/12 | JV Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Tue., 10/12 | V Girls Soccer | Naugatuck | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | W 3-2 | |
| Tue., 10/12 | V Girls Volleyball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | L 1-3 | |
| Tue., 10/12 | JV Girls Volleyball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 10/13 | JV Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 5:15 p.m. | ||
| Thu., 10/14 | FM Football | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | ||
| Thu., 10/14 | V Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:30 p.m. | W 3-2 | |
| Thu., 10/14 | JV Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 10/15 | V Football | Oxford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 20-13 | |
| Fri., 10/15 | V Boys Soccer | Ansonia | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:00 p.m. | W 7-1 | |
| Fri., 10/15 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Ave [Directions] | 3:00 p.m. | W 1-0 | |
| Fri., 10/15 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Home - Watertown HS-Pool [Directions] | 5:15 p.m. | ||
| Fri., 10/15 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 6:30 p.m. | L 2-3 | |
| Fri., 10/15 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 10/16 | JV Football | Northwest United | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | JV Football | Oxford | Away - Oxford HS-Wolverine Field [Directions] | Canceled | Cancelled | |
| Sat., 10/16 | JV Girls Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | 10:00 a.m. | ||
| Mon., 10/18 | V Girls Soccer | Torrington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | W 7-0 | |
| Tue., 10/19 | V Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/19 | V Girls Swimming and Diving | Woodland | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Tue., 10/19 | V Girls Volleyball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 6:30 p.m. | L 1-3 | |
| Tue., 10/19 | JV Girls Volleyball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 10/20 | V Boys Cross Country | Wolcott | Home - Watertown HS-Veteran's Park [Directions] | 2:15 p.m. | ||
| Wed., 10/20 | V Boys Soccer | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 4-1 | |
| Wed., 10/20 | V Girls Cross Country | Wolcott | Home - Watertown HS-Veteran's Park [Directions] | 2:15 p.m. | ||
| Wed., 10/20 | V Girls Soccer | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 6:00 p.m. | W 1-0 | |
| Thu., 10/21 | FR Football | Shelton | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | ||
| Thu., 10/21 | JV Girls Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | 5:30 p.m. | ||
| Thu., 10/21 | V Girls Volleyball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 10/21 | JV Girls Volleyball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Fri., 10/22 | V Football | Naugatuck | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 12-34 | |
| Fri., 10/22 | JV Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | Postponed | ||
| Fri., 10/22 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:00 p.m. | W 2-0 | |
| Fri., 10/22 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | Canceled | Cancelled | |
| Sat., 10/23 | FM Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | JV Boys Soccer | Nonnewaug, Litchfield, Wamogo | Away - Nonnewaug HS-JV Field [Directions] | 10:00 a.m. | ||
| Mon., 10/25 | V Boys Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 6:00 p.m. | W 9-2 | |
| Mon., 10/25 | V Field Hockey | Thomaston | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | T 1-1 | |
| Mon., 10/25 | JV Field Hockey | Thomaston | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Mon., 10/25 | V Girls Soccer | Derby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:00 p.m. | W 8-0 | |
| Mon., 10/25 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:30 p.m. | L 0-3 | |
| Mon., 10/25 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 10/27 | V Boys Soccer | Holy Cross | Away - Municipal Stadium-Bethel HS Track & Field Training Center [Directions] | 6:30 p.m. | L 4-1 | |
| Wed., 10/27 | V Girls Soccer | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 5-0 | |
| Wed., 10/27 | V Girls Volleyball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 10/27 | JV Girls Volleyball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Thu., 10/28 | JV Boys Soccer | Holy Cross | Home - Watertown HS-Veteran's Park [Directions] | 3:30 p.m. | ||
| Thu., 10/28 | V Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 10/28 | JV Field Hockey | Shepaug Valley | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Fri., 10/29 | V Football | Kennedy | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 22-14 | |
| Sat., 10/30 | FM Football | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | Canceled | Cancelled | |
| Sat., 10/30 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 12:30 p.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class MM Championship | Away - Wickham Park | 10:20 a.m. | ||
| Mon., 11/1 | V Boys Soccer | WCA | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 8:00 p.m. | W 3-0 | |
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class M Championship | Away - Wickham Park | 9:45 a.m. | ||
| Mon., 11/1 | V Girls Soccer | Seymour | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | W 5-0 | |
| Tue., 11/2 | V Boys Soccer | Woodland | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 5:30 p.m. | W 1-0 | |
| Tue., 11/2 | V Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 4-2 | |
| Tue., 11/2 | JV Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | Canceled | Cancelled | |
| Tue., 11/2 | V Girls Soccer | Holy Cross | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 5:30 p.m. | L 2-1 | |
| Thu., 11/4 | V Boys Soccer | Holy Cross | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | L 3-3 | |
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | FM Football | Crosby | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | ||
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | V Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 10:00 a.m. | W 7-6 | |
| Mon., 11/8 | V Girls Soccer | Montville | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | W 9-2 | |
| Mon., 11/8 | V Girls Volleyball | Branford | Away - Branford HS-Gym [Directions] | 6:00 p.m. | ||
| Tue., 11/9 | V Field Hockey | Granby Memorial | Away - Granby Memorial HS-Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 11/10 | V Girls Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 2:00 p.m. | ||
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/11 | V Football | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 6:00 p.m. | W 34-12 | |
| Thu., 11/11 | V Boys Soccer | Brookfield | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 1:00 p.m. | W 6-4 | |
| Sat., 11/13 | FM Football | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Sat., 11/13 | FM Football | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 11/13 | V Boys Soccer | E.O. Smith | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 1:00 p.m. | W 3-1 | |
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Wed., 11/17 | V Boys Soccer | Fitch | Home - Jonathan Law HS-Lawmen Stadium [Directions] | 7:00 p.m. | L 2-1 | |
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/20 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:00 a.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Thu., 11/25 | V Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:15 a.m. | L 6-39 | |
| Sat., 12/4 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:30 p.m. | ||
| Wed., 12/8 | V Boys Basketball | Litchfield (Scrim.) | Home - Watertown HS [Directions] | 6:30 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Tri-Town (Scrim.) | Away - Enfield Twin Rinks-Rink 2 [Directions] | 3:50 p.m. | ||
| Thu., 12/9 | V Girls Basketball | Kaynor Tech | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Mon., 12/13 | V Boys Basketball | Lewis Mills (Scrim.) | Away - Lewis Mills HS-Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 12/14 | V Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:45 p.m. | L 44-56 | |
| Tue., 12/14 | JV Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/15 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 4-5 | |
| Wed., 12/15 | V Wrestling | Weston | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Weston 39 Pomperaug 33 | |
| Thu., 12/16 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Postponed | ||
| Fri., 12/17 | V Girls Basketball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 57-22 | |
| Fri., 12/17 | JV Girls Basketball | Crosby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/18 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 12:00 p.m. | L 36-86 | |
| Sat., 12/18 | JV Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 10:30 a.m. | ||
| Sat., 12/18 | FR Boys Basketball | Wolcott, St. Paul Catholic | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Daniel Hand | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 3-0 | |
| Sat., 12/18 | V Wrestling | Pomperaug Quads (2 mats) | Home - Pomperaug HS-Auxiliary Gym [Directions] | 10:00 a.m. | Pomperaug 59 Terryville 12 Pomperaug 48 bacon academy 24 Pomperaug 48 nonnewaug 21 Pomperaug 45 new Canaan 30 Pomperaug 48 Portland 18 | |
| Mon., 12/20 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 5-0 | |
| Tue., 12/21 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | W 66-26 | |
| Tue., 12/21 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 12/21 | V Girls Gymnastics | Jonathan Law, Hamden | Away - Jonathan Law HS-Old Gym [Directions] | 6:00 p.m. | 37.3 | |
| Wed., 12/22 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/22 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/22 | V Boys Ice Hockey | Sheehan | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 1-8 | |
| Wed., 12/22 | V Wrestling | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:00 p.m. | Pomperaug 36 Masuk 15 | |
| Thu., 12/23 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 42-66 | |
| Thu., 12/23 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/23 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 12/23 | JV Girls Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Mon., 12/27 | FR Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 12/28 | V Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 49-66 | |
| Tue., 12/28 | JV Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/28 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 1:30 p.m. | L 1-5 | |
| Wed., 12/29 | V Girls Gymnastics | Farmington, Ellington/Tolland | Away - Farmington Valley Gymnastics & More-Farmington Valley Gymnastics-Plainville [Directions] | 6:00 p.m. | 90.75 | |
| Thu., 12/30 | V Boys Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 42-56 | |
| Thu., 12/30 | JV Boys Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/30 | FR Boys Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Thu., 12/30 | V Wrestling | Trumbull Duals | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | Cancelled | |
| Tue., 1/4 | V Boys Basketball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 34-78 | |
| Tue., 1/4 | JV Boys Basketball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/4 | FR Boys Basketball | Kennedy | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Tue., 1/4 | V Boys Swimming and Diving | Nonnewaug | Home - Watertown HS-Pool [Directions] | 5:30 p.m. | ||
| Tue., 1/4 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 1/5 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms-Jennings Rink [Directions] | 8:00 p.m. | L 1-4 | |
| Thu., 1/6 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 7:00 p.m. | L 47-50 | |
| Thu., 1/6 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/6 | V Wrestling | Haddam-Killingworth, Middletown, Nonnewaug (2 mats) | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | Pomperaug 39 Middletown 27 Pomperaug 36 Haddam-killingworth 30 | |
| Thu., 1/6 | V Girls Basketball | Derby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 55-14 | |
| Thu., 1/6 | JV Girls Basketball | Derby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Sat., 1/8 | V Boys Ice Hockey | Immaculate | Home - Taft School-Mays [Directions] | 8:00 p.m. | L 4-6 | |
| Sat., 1/8 | V Wrestling | Bristol Central Invitational (4 mats) | Away - Bristol Central HS-Charles C. Marsh Gymnasium | 8:00 a.m. | Mike carpenter 1st Zach Hartman 1st Julianna Morris 4th Noen Jian 5th Alex Lee 5th Emin ismaili 5th Steve Purcell 6th Blake Dawson 6th | |
| Sat., 1/8 | V Girls Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:00 p.m. | L 46-47 | |
| Mon., 1/10 | V Wrestling | Brookfield/Shepaug | Away - Brookfield HS-BHS Small Gym [Directions] | 6:00 p.m. | Pomperaug 63 Brookfield 4 | |
| Mon., 1/10 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:00 p.m. | W 44-40 | |
| Mon., 1/10 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | Postponed | ||
| Tue., 1/11 | V Boys Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 68-41 | |
| Tue., 1/11 | JV Boys Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/11 | FR Boys Basketball | Seymour | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Tue., 1/11 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 5:30 p.m. | ||
| Tue., 1/11 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | L 50-74 | |
| Tue., 1/11 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/12 | V Wrestling | Stratford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 47 Stratford 24 | |
| Thu., 1/13 | V Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 7:00 p.m. | W 66-57 | |
| Thu., 1/13 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/13 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 1/13 | V Girls Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 52-16 | |
| Thu., 1/13 | JV Girls Basketball | Wilby | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/14 | V Boys Basketball | Wolcott | Home - Watertown HS [Directions] | 7:00 p.m. | W 66-54 | |
| Fri., 1/14 | JV Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/14 | FR Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/14 | V Boys Swimming and Diving | Crosby/WCA | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 1/14 | JV Girls Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Sat., 1/15 | FR Boys Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/15 | V Boys Ice Hockey | Lyman Hall | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 2-4 | |
| Sat., 1/15 | V Wrestling | Berlin, Avon, Bethel, Branford, Portland, Terryville/Thomaston (3 mats) | Away - Berlin HS-Jim Day Gymnasium | 10:00 a.m. | Pomperaug 18 Branford 46 Pomperaug 54 Berlin 15 Pomperaug 45 Bethel 24 Pomperaug 22 Avon 60 | |
| Sat., 1/15 | V Girls Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:00 p.m. | W 61-51 | |
| Mon., 1/17 | V Boys Ice Hockey | North Haven | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 3-5 | |
| Mon., 1/17 | V Girls Gymnastics | Joel Barlow, Newtown | Home - Vasi's Gymnastics [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Tue., 1/18 | V Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 33-43 | |
| Tue., 1/18 | JV Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Boys Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Tue., 1/18 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 6:45 p.m. | L 43-71 | |
| Tue., 1/18 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 1/19 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | W 5-2 | |
| Wed., 1/19 | V Wrestling | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | Pomperaug 42 Bunnell 39 | |
| Fri., 1/21 | V Boys Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 50-76 | |
| Fri., 1/21 | JV Boys Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/21 | FR Boys Basketball | Ansonia | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Fri., 1/21 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:30 p.m. | W 63-60(OT) | |
| Fri., 1/21 | JV Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | Branford | Away - Northford Ice Pavilion-Red [Directions] | 5:00 p.m. | L 4-5 | |
| Sat., 1/22 | V Wrestling | Xavier, Bristol Central, Bristol Eastern, Burlington (MA), Cheshire, Fitch, Guilford, Joel Barlow, TBA, Ridgefield, Simsbury, Trumbull, Hall, Xaverian Brothers (MA) | Away - Xavier HS-Gym | 9:00 a.m. | ||
| Sat., 1/22 | V Girls Gymnastics | Daniel Hand, TBA | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus [Directions] | 10:00 a.m. | 108.05 | |
| Mon., 1/24 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 44-47 | |
| Mon., 1/24 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 1/24 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/25 | V Girls Gymnastics | New Milford, Newtown | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:00 p.m. | 115.4 | |
| Wed., 1/26 | FR Boys Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/26 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:25 p.m. | W 5-4 | |
| Wed., 1/26 | V Boys Swimming and Diving | Litchfield | Home - Watertown HS-Pool [Directions] | 5:30 p.m. | ||
| Wed., 1/26 | V Wrestling | Newtown | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Newtown 38 Pomperaug 36 | |
| Wed., 1/26 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:30 p.m. | L 43-47 | |
| Wed., 1/26 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/28 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:30 p.m. | W 59-48 | |
| Fri., 1/28 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | Postponed | ||
| Fri., 1/28 | V Boys Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 5:30 p.m. | ||
| Fri., 1/28 | V Girls Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:30 p.m. | W 65-53 | |
| Fri., 1/28 | JV Girls Basketball | Oxford | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Sat., 1/29 | FR Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/29 | FR Boys Basketball | Freshmen Basketball Jamboree | Away - TBA | 9:00 a.m. | ||
| Sat., 1/29 | V Wrestling | Brookfield, Bethel, Canton, Danbury, Darien, Joel Barlow, Montville, New Canaan, Newtown, Stratford, Harding, Wilton | Away - Brookfield HS-BHS Small & Big Gym | Canceled | Cancelled | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/30, Time to 11:00 a.m. | ||||||
| Mon., 1/31 | V Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 7:00 p.m. | W 54-49 | |
| Mon., 1/31 | JV Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 1/31 | JV Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/31 | FR Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 7:00 p.m. | W 55-52 | |
| Tue., 2/1 | JV Boys Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/1 | FR Boys Basketball | Litchfield | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/1 | FR Boys Basketball | Wolcott | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Tue., 2/1 | V Boys Swimming and Diving | Naugatuck | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | Conard | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 5-1 | |
| Wed., 2/2 | V Wrestling | New Milford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | New milford 48 Pomperaug 26 | |
| Thu., 2/3 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 42-66 | |
| Thu., 2/3 | JV Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | V Boys Swimming and Diving | Seymour | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Thu., 2/3 | V Girls Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 51-48 | |
| Thu., 2/3 | JV Girls Basketball | Torrington | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | V Girls Gymnastics | Newtown, Brookfield | Away - Vasi's Gymnastics [Directions] | 7:30 p.m. | 112.65 | |
| Fri., 2/4 | FR Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | Postponed | ||
| Fri., 2/4 | V Wrestling | Farmington, Maloney, TBA, New Milford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:30 p.m. | Cancelled | |
| Sat., 2/5 | FR Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | North Branford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 5-3 | |
| Sat., 2/5 | V Wrestling | Farmington, Maloney | Home - Pomperaug HS-Auxiliary Gym [Directions] | 11:00 a.m. | Pomperaug 42 Farmington 26 Pomperaug 42 Maloney 36 | |
| Sat., 2/5 | V Girls Gymnastics | Newtown | Home - Vasi's Gymnastics [Directions] | TBA | 113.90 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Tue., 2/8 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 36-62 | |
| Tue., 2/8 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Girls Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 56-43 | |
| Tue., 2/8 | JV Girls Basketball | St. Paul Catholic | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/9 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 4:15 p.m. | L 1-4 | |
| Wed., 2/9 | V Boys Swimming and Diving | Kennedy | Away - J F Kennedy HS Turf-John Reardon Pool [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | V Girls Gymnastics | SWC Gymnastics Championships | Away - New Milford HS-Main Gym - NMHS | 5:00 p.m. | 117.95 | |
| Fri., 2/11 | V Boys Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 29-83 | |
| Fri., 2/11 | JV Boys Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/11 | FR Boys Basketball | Naugatuck | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | Postponed | ||
| Fri., 2/11 | V Boys Swimming and Diving | Oxford | Home - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 49-64 | |
| Fri., 2/11 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 2/12 | V Boys Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 11:30 a.m. | W 52-44 | |
| Sat., 2/12 | JV Boys Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | Postponed | ||
| Sat., 2/12 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | Postponed | ||
| Sat., 2/12 | V Boys Ice Hockey | Guilford | Home - Taft School-Mays [Directions] | 8:00 p.m. | T 4-4(OT) | |
| Sat., 2/12 | V Wrestling | New Milford, Brookfield, Bunnell, Joel Barlow, Masuk, SWC Tournament, New Fairfield, Newtown, Stratford, Weston | Away - New Milford HS-Main Gym - NMHS | 8:30 a.m. | ||
| Mon., 2/14 | V Boys Basketball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 46-71 | |
| Mon., 2/14 | JV Boys Basketball | WCA | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS (Waterbury) [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | V Girls Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 5:30 p.m. | W 70-61 | |
| Wed., 2/16 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:30 p.m. | W 3-1 | |
| Thu., 2/17 | V Girls Basketball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 52-76 | |
| Thu., 2/17 | JV Girls Basketball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | FR Baseball | Boys Basketball | Away - TBA | 3:30 p.m. | ||
| Fri., 2/18 | V Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 58-91 | |
| Fri., 2/18 | JV Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/18 | V Wrestling | Class L Championship - Day 1 | Away - Wilton | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | W 3-1 | |
| Sat., 2/19 | V Wrestling | Class L Championship - Day 2 | Away - Wilton | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Basketball | St. Paul Catholic | Away - Holy Cross HS-Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/19 | V Girls Gymnastics | Joel Barlow, Brookfield, Newtown | Away - Gymnastics Revolution [Directions] | 5:00 p.m. | 86.25 | |
| Mon., 2/21 | FR Boys Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:00 p.m. | ||
| Mon., 2/21 | V Boys Swimming and Diving | Torrington | Home - Watertown HS-Pool [Directions] | 5:00 p.m. | ||
| Wed., 2/23 | V Boys Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 45-57 | |
| Wed., 2/23 | JV Boys Basketball | Woodland | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | Westhill/Stamford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 2-1 | |
| Thu., 2/24 | FR Boys Basketball | Holy Cross | Home - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:00 p.m. | ||
| Sat., 2/26 | V Boys Swimming and Diving | Woodland, Crosby/WCA, Holy Cross, Kennedy, Naugatuck, Oxford, Seymour, Torrington, WCA | Away - John F. Kennedy HS-John Reardon Pool | 12:00 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/28 | FR Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Small Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | East Haven Coop | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-3(OT) | |
| Tue., 3/1 | V Girls Basketball | Plainfield | Home - Watertown High-Robert B Cook Gym [Directions] | 6:00 p.m. | ||
| Wed., 3/2 | V Girls Swimming and Diving | TBA, Crosby, Holy Cross, Kennedy, TBA, Oxford, Seymour, Torrington, WCA | Away - Watertown HS | 6:00 p.m. | ||
| Fri., 3/4 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | ||
| Sat., 3/5 | V Boys Swimming and Diving | Woodland, Crosby/WCA, Holy Cross, Kennedy, Naugatuck, Oxford, Seymour, Torrington, WCA | Away - John F. Kennedy HS-John Reardon Pool | 11:00 a.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Mon., 3/7 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | 5:30 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/11 | V Boys Ice Hockey | Wethersfield | Away - Koeppel Community Sports Center - Trinity College-Albert Creighton Williams '64 Rink [Directions] | 8:00 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class M Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Fri., 3/25 | V Girls Lacrosse | Immaculate (Scrim.) | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | ||
| Fri., 3/25 | V Softball | Thomaston (Scrim.) | Home - Watertown High-Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 3/26 | V Baseball | East Hampton (Scrim.) | Home - Deland Field-Deland field [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Boys Lacrosse | Pomperaug (Scrim.) | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 11:00 a.m. | ||
| Tue., 3/29 | V Baseball | Pomperaug (Scrim.) | Home - Deland Field-Deland field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Girls Lacrosse | Brookfield (Scrim.) | Away - Brookfield HS-BHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 3/30 | V Boys Lacrosse | Hamden (Scrim.) | Away - Hamden HS-HHS Turf Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Girls Tennis | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Sat., 4/2 | V Boys Tennis | Holy Cross | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 10:00 a.m. | W 5-0 [Detailed Results] | |
| Sat., 4/2 | V Girls Tennis | St. Paul Catholic | Away - Page Park -Baseball Field [Directions] | 12:00 p.m. | W 6-1 | |
| Mon., 4/4 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:00 p.m. | W 8-2 | |
| Mon., 4/4 | V Boys Lacrosse | Vinal-Goodwin | Away - Vinal Tech-Lacrosse Field 1 [Directions] | 5:00 p.m. | W 20-1 | |
| Mon., 4/4 | V Softball | Seymour | Home - Watertown High-Softball Field [Directions] | 3:00 p.m. | W 9-1 | |
| Mon., 4/4 | V Girls Tennis | Seymour | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:00 p.m. | W 6-1 | |
| Tue., 4/5 | V Baseball | WCA | Home - Deland Field-Deland field [Directions] | 5:00 p.m. | W 14-0 | |
| Tue., 4/5 | JV Baseball | Seymour | Away - French Park-Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 4/5 | V Boys Outdoor Track | Seymour | Home - Watertown HS [Directions] | 3:00 p.m. | ||
| Tue., 4/5 | V Boys Tennis | Southington | Away - Southington HS-Tennis Courts [Directions] | 4:45 p.m. | L 2-5 [Detailed Results] | |
| Tue., 4/5 | V Girls Lacrosse | Berlin | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 13-12 | |
| Tue., 4/5 | V Girls Outdoor Track | Seymour | Home - Watertown HS [Directions] | 3:00 p.m. | ||
| Tue., 4/5 | V Softball | WCA | Away - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | 4:00 p.m. | W 24-3 | |
| Thu., 4/7 | V Boys Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 5:00 p.m. | L 11-16 | |
| Fri., 4/8 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | W 3-2 [Detailed Results] | |
| Fri., 4/8 | V Girls Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 18-3 | |
| Fri., 4/8 | V Softball | Woodland | Home - Watertown High-Softball Field [Directions] | 4:15 p.m. | L 0-10 | |
| Sat., 4/9 | JV Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 4/11 | V Baseball | Crosby | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | W 10-0 | |
| Mon., 4/11 | V Boys Tennis | Crosby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | Cancelled | |
| Mon., 4/11 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Mon., 4/11 | V Softball | Crosby | Away - Crosby HS-CHS Softball Field #1 [Directions] | 3:30 p.m. | W 18-0 | |
| Mon., 4/11 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Tue., 4/12 | V Boys Outdoor Track | St. Paul Catholic, Wilby | Home - Watertown HS [Directions] | 4:45 p.m. | ||
| Tue., 4/12 | V Girls Outdoor Track | St. Paul Catholic, Wilby | Home - Watertown HS [Directions] | 4:45 p.m. | ||
| Wed., 4/13 | V Baseball | Ansonia | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 8-5 | |
| Wed., 4/13 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | forte 44 Wolcott 225 lacapra 48 krayeske 43 lamadeleine 48 | |
| Wed., 4/13 | V Girls Lacrosse | Southington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | L 12-6 | |
| Wed., 4/13 | JV Girls Lacrosse | Southington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:30 p.m. | ||
| Wed., 4/13 | V Softball | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:00 p.m. | W 7-3 | |
| Wed., 4/13 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Thu., 4/14 | V Boys Golf | Naugatuck | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 12:45 p.m. | forte 47 Naugatuck 233 lacapra 44 krayeske 51 lamadeleine 47 | |
| Thu., 4/14 | V Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | 2:00 p.m. | W 11-5 | |
| Thu., 4/14 | V Girls Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 1:30 p.m. | W 6-1 | |
| Fri., 4/15 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 4:00 p.m. | W 16-0 | |
| Fri., 4/15 | V Girls Lacrosse | Housatonic Regional | Away - Housatonic Valley Regional High-football field [Directions] | 4:00 p.m. | W 15-6 | |
| Sat., 4/16 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 11:00 a.m. | L 3-1 | |
| Sat., 4/16 | FR Baseball | Naugatuck | Away - Rotary Field-Baseball [Directions] | Canceled | Cancelled | |
| Sat., 4/16 | V Boys Lacrosse | Newington | Away - Newington HS-Clem Lemire Turf Field (150 New Britain Ave) [Directions] | 9:00 a.m. | W 11-6 | |
| Sat., 4/16 | JV Boys Lacrosse | Newington | Away - Newington HS-VA Field 1 [Directions] | 10:45 a.m. | ||
| Sat., 4/16 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 11:00 a.m. | W 4-1 [Detailed Results] | |
| Sat., 4/16 | V Girls Tennis | Naugatuck | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 10:00 a.m. | W 4-3 | |
| Mon., 4/18 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 11:00 a.m. | forte 45 lacapra 47 lamadeleine 47 krayeske 45 | |
| Mon., 4/18 | V Boys Tennis | Woodland | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 2-3 [Detailed Results] | |
| Mon., 4/18 | V Softball | Nonnewaug | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 4/19 | V Boys Outdoor Track | Holy Cross, Woodland | Home - Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 4/19 | V Girls Lacrosse | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 11:00 a.m. | W 12-7 | |
| Tue., 4/19 | V Girls Outdoor Track | Holy Cross, Woodland | Home - Watertown HS [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | L 4-1 | |
| Wed., 4/20 | V Boys Golf | Woodland | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | lacapra 45 woodland 256 lamadeleine 47 leach 49 krayeske 48 | |
| Wed., 4/20 | V Boys Lacrosse | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | W 13-4 | |
| Wed., 4/20 | V Boys Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 11:00 a.m. | W 5-0 [Detailed Results] | |
| Wed., 4/20 | V Softball | Torrington | Home - Watertown High-Softball Field [Directions] | 2:00 p.m. | W 8-0 | |
| Wed., 4/20 | V Girls Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Thu., 4/21 | V Baseball | New Milford | Away - New Milford HS-Baseball Varsity Field - NMHS [Directions] | 4:00 p.m. | L 8-7 | |
| Thu., 4/21 | JV Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | Canceled | Cancelled | |
| Thu., 4/21 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | 2:30 p.m. | forte 47 seymour249 lacapra 46 krayeske 43 lamadeleine 47 | |
| Thu., 4/21 | V Girls Lacrosse | Middletown/Coginchaug | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 19-10 | |
| Thu., 4/21 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | 5:30 p.m. | W 21-5 | |
| Fri., 4/22 | V Baseball | Derby | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | W 7-1 | |
| Fri., 4/22 | V Boys Lacrosse | Capital Prep | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | W 17-0 | |
| Sat., 4/23 | V Baseball | St. Paul Catholic | Home - Deland Field-Deland field [Directions] | 2:00 p.m. | L 2-1 | |
| Sat., 4/23 | V Boys Lacrosse | Stamford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 12:00 p.m. | W 14-4 | |
| Sat., 4/23 | JV Boys Lacrosse | Stamford | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 1:30 p.m. | ||
| Mon., 4/25 | V Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | W 21-2 | |
| Mon., 4/25 | V Boys Golf | Torrington | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | forte44 torrington 254 lacapra 44 krayeske 46 lamadeleine 45 | |
| Mon., 4/25 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 6:00 p.m. | W 10-4 | |
| Mon., 4/25 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Mon., 4/25 | V Softball | Wilby | Home - Watertown High-Softball Field [Directions] | 5:00 p.m. | W 19-0 | |
| Mon., 4/25 | V Girls Tennis | Wilby | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Tue., 4/26 | V Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 3:00 p.m. | W 3-2 | |
| Tue., 4/26 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 3:00 p.m. | forte 45 St Paul 176 lacapra 46 krayeske 44 lamadeleine 45 | |
| Tue., 4/26 | V Girls Lacrosse | Lewis Mills | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 16-7 | |
| Wed., 4/27 | V Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | 3:45 p.m. | W 16-4 | |
| Wed., 4/27 | V Boys Lacrosse | Holy Cross | Away - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 4:00 p.m. | W 15-7 | |
| Wed., 4/27 | V Boys Outdoor Track | Crosby, Derby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 5:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Wed., 4/27 | V Girls Lacrosse | Housatonic Regional | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | W 14-4 | |
| Wed., 4/27 | V Girls Outdoor Track | Crosby, Derby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 5:00 p.m. | ||
| Wed., 4/27 | V Softball | Kennedy | Home - Watertown High-Softball Field [Directions] | 5:00 p.m. | W 16-1 | |
| Wed., 4/27 | V Girls Tennis | Kennedy | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 4/29 | V Baseball | Torrington | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | W 6-3 | |
| Fri., 4/29 | V Boys Tennis | Torrington | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Fri., 4/29 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 4/29 | V Girls Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Sat., 4/30 | JV Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-THS Varsity Ladies Softball [Directions] | Canceled | Cancelled | |
| Sat., 4/30 | JV Girls Tennis | JV Girls Tennis Tournament | Away - Nonnewaug HS-Tennis Courts | 9:00 a.m. | ||
| Mon., 5/2 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | forte 44 HC 193 lacapra 42 krayeske 44 lamadeleine 45 | |
| Mon., 5/2 | V Boys Lacrosse | Wolcott | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | W 11-4 | |
| Mon., 5/2 | V Softball | Naugatuck | Home - Watertown High-Softball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Baseball | Naugatuck | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 9-8 | |
| Tue., 5/3 | V Boys Outdoor Track | Oxford, WCA | Home - Watertown HS [Directions] | 2:30 p.m. | ||
| Tue., 5/3 | V Boys Tennis | Naugatuck | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Tue., 5/3 | V Girls Lacrosse | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 8-7 | |
| Tue., 5/3 | V Girls Outdoor Track | Oxford, WCA | Home - Watertown HS [Directions] | 2:30 p.m. | ||
| Tue., 5/3 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | W 4-3 | |
| Wed., 5/4 | FR Baseball | Wolcott | Away - BAW B Field Salerno-BAW - B Field [Directions] | Canceled | Cancelled | |
| Wed., 5/4 | V Boys Golf | Wolcott | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | forte45 Wolcott 246 lacapra 46 krayeske 41 lamadeleine 45 | |
| Thu., 5/5 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 5:15 p.m. | W 4-2 | |
| Thu., 5/5 | JV Baseball | Wolcott | Away - Wolcott HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Thu., 5/5 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | forte 42 naugy 222 lacapra 46 krayeske 42 leach 41 | |
| Thu., 5/5 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 5:00 p.m. | W 4-1 [Detailed Results] | |
| Thu., 5/5 | V Girls Lacrosse | Danbury | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:30 p.m. | L 18-9 | |
| Thu., 5/5 | JV Girls Lacrosse | Danbury | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | V Softball | Oxford | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | L 0-5 | |
| Sat., 5/7 | V Boys Lacrosse | Canton | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | W 11-8 | |
| Sat., 5/7 | JV Boys Lacrosse | Canton | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 11:30 a.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Mon., 5/9 | V Baseball | Oxford | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 9-2 | |
| Mon., 5/9 | V Boys Golf | Waterbury Coop | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | lacapra 42 WTBY 222 krayeske 44 leach 44 lamadeleine 47 | |
| Mon., 5/9 | V Boys Tennis | Kennedy | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Mon., 5/9 | V Girls Lacrosse | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 4:00 p.m. | L 17-8 | |
| Mon., 5/9 | JV Girls Lacrosse | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 5:30 p.m. | ||
| Mon., 5/9 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:45 p.m. | L 7-12 | |
| Tue., 5/10 | V Boys Outdoor Track | Torrington, Kennedy | Away - Torrington HS [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | Cancelled | |
| Tue., 5/10 | V Boys Tennis | Holy Cross | Away - Wilby HS [Directions] | 3:30 p.m. | W 5-0 [Detailed Results] | |
| Tue., 5/10 | V Girls Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 4:30 p.m. | L 13-6 | |
| Tue., 5/10 | JV Girls Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 6:00 p.m. | ||
| Tue., 5/10 | V Girls Outdoor Track | Torrington, Kennedy | Away - Torrington HS [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Softball | Naugatuck | Home - Watertown High-Softball Field [Directions] | 3:45 p.m. | L 5-9 | |
| Tue., 5/10 | JV Softball | Wolcott | Away - Wolcott HS-JV Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/10 | V Girls Tennis | Nonnewaug | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Wed., 5/11 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:00 p.m. | lacapra 40 woodland 229 krayeske 50 lamadeleine 40 leach 47 | |
| Wed., 5/11 | V Boys Lacrosse | Capital Prep | Away - Quirk MS-Soccer Field [Directions] | 3:30 p.m. | W 20-1 | |
| Wed., 5/11 | V Girls Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/12 | V Boys Golf | Seymour | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | 178 | |
| Thu., 5/12 | V Boys Lacrosse | Holy Cross | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 15-8 | |
| Thu., 5/12 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 7:00 p.m. | L 2-8 | |
| Thu., 5/12 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Thu., 5/12 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Thu., 5/12 | V Girls Tennis | Wolcott | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 2:00 p.m. | W 4-3 | |
| Thu., 5/12 | V Girls Tennis | Holy Cross | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Fri., 5/13 | V Baseball | Wolcott | Home - Deland Field-Deland field [Directions] | 4:30 p.m. | L 5-3 | |
| Fri., 5/13 | JV Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | Canceled | Cancelled | |
| Fri., 5/13 | V Boys Tennis | Wolcott | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:30 p.m. | W 4-1 [Detailed Results] | |
| Fri., 5/13 | V Softball | Wolcott | Away - Wolcott HS-George Babcock Softball Field [Directions] | 3:45 p.m. | L 3-13 | |
| Fri., 5/13 | V Girls Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | L 2-5 | |
| Sat., 5/14 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Canceled | Cancelled | |
| Sat., 5/14 | V Boys Tennis | Pomperaug | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 10:00 a.m. | W 5-0 [Detailed Results] | |
| Mon., 5/16 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 2:00 p.m. | W 5-0 [Detailed Results] | |
| Tue., 5/17 | V Baseball | New Milford | Home - Deland Field-Deland field [Directions] | 3:45 p.m. | L 19-11 | |
| Tue., 5/17 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Boys Golf | St. Paul Catholic | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | 183 | |
| Tue., 5/17 | V Boys Lacrosse | Lewis Mills | Away - Lewis Mills HS-JV Soccer/Lacrosse Field [Directions] | 4:00 p.m. | W 17-8 | |
| Tue., 5/17 | JV Boys Lacrosse | Lewis Mills | Away - Lewis Mills HS-JV Soccer/Lacrosse Field [Directions] | 5:30 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 3:30 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Holy Cross | Away - Wilby HS [Directions] | 3:30 p.m. | ||
| Tue., 5/17 | V Girls Lacrosse | Shelton | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 15-7 | |
| Tue., 5/17 | V Girls Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 3:30 p.m. | ||
| Tue., 5/17 | V Softball | Wolcott | Home - Watertown High-Softball Field [Directions] | 3:15 p.m. | L 0-13 | |
| Tue., 5/17 | V Softball | Holy Cross | Home - Watertown High-Softball Field [Directions] | 5:30 p.m. | W 9-6 | |
| Tue., 5/17 | V Girls Tennis | St. Paul Catholic | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Wed., 5/18 | V Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 0-10 | |
| Wed., 5/18 | V Boys Golf | Holy Cross | Home - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | 182 | |
| Wed., 5/18 | V Boys Lacrosse | Bristol Coop | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 17-4 | |
| Wed., 5/18 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:30 p.m. | L 15-10 | |
| Wed., 5/18 | V Softball | St. Paul Catholic | Home - Watertown High-Softball Field [Directions] | 5:30 p.m. | W 5-2 | |
| Thu., 5/19 | V Baseball | St. Paul Catholic | Away - Waterville Park-Baseball Diamond [Directions] | 4:30 p.m. | L 16-1 | |
| Thu., 5/19 | V Girls Lacrosse | Newington | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 11-19 | |
| Sat., 5/21 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 6:30 p.m. | ||
| Mon., 5/23 | V Girls Lacrosse | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 4:00 p.m. | W 22-15 | |
| Mon., 5/23 | JV Girls Lacrosse | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 5:30 p.m. | ||
| Mon., 5/23 | V Girls Tennis | NVL Girls Tennis Individual Tournament | Away - Woodland HS-Tennis Courts | 12:00 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:00 p.m. | L 8-19 | |
| Thu., 5/26 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | 170 | |
| Thu., 5/26 | V Boys Lacrosse | St. Paul Catholic | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 8:00 p.m. | ||
| Thu., 5/26 | V Girls Lacrosse | Away - St. Paul Catholic HS -McPhee Field | 3:00 p.m. | |||
| Fri., 5/27 | V Softball | Holy Cross (Scrim.) | Home - Watertown High-Softball Field [Directions] | 5:00 p.m. | ||
| Sun., 5/29 | V Baseball | Goodwin Tech | Home - Deland Field-Deland field [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Baseball | Bacon Academy | Away - Bacon Academy-Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Tennis | Lyman Hall | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 1:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/31 | V Girls Lacrosse | Stonington | Away - Stonington HS-Palmer Field-turf [Directions] | 5:00 p.m. | ||
| Tue., 5/31 | V Softball | Sacred Heart Academy | Home - Watertown High-Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Tennis | Waterford | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Baseball | Jonathan Law | Away - Jonathan Law HS-Baseball Field [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Avon | Home - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | ||
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class MM Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 6/1 | V Boys Tennis | Berlin | Home - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:00 p.m. | L 1-6 [Detailed Results] | |
| Wed., 6/1 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 6/2 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Fri., 6/3 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 6/6 | V Boys Golf | CIAC Division II Spring Championship | Away - Tallwood CC | 7:30 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Softball | Woodland | Away - DeLuca Field-Deluca Field [Directions] | 4:00 p.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||