| Oxford 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 591 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Derby | Home - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Ansonia | Home - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Sacred Heart | Home - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Wilby | Home - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | TBA | ||
| TBA | JV Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | TBA | ||
| TBA | JV Boys Basketball | Derby | Home - OHS-Main Gym [Directions] | TBA | ||
| TBA | JV Boys Basketball | Sacred Heart | Home - OHS-Main Gym [Directions] | TBA | ||
| TBA | FM Football | Wilby | Away - Wilby H.S. [Directions] | TBA | ||
| TBA | FM Football | WCA | Home - OHS Wolverine Field (Turf) [Directions] | TBA | ||
| TBA | V Boys Outdoor Track | WCA, Kennedy | Home - OHS Track [Directions] | 3:30 p.m. | ||
| TBA | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | TBA | ||
| TBA | JV Boys Soccer | Wilby | Home - OHS Soccer Field-West [Directions] | TBA | ||
| TBA | JV Boys Soccer | Sacred Heart | Away - Waterville Park | TBA | ||
| TBA | V Boys Volleyball | Cheshire | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | Senior Night |
| TBA | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| TBA | JV Boys Volleyball | Cheshire | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | Senior Night |
| TBA | JV Girls Basketball | Ansonia | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| TBA | V Girls Outdoor Track | WCA, Kennedy | Home - OHS Track [Directions] | 3:30 p.m. | ||
| TBA | JV Girls Soccer | Derby | Away - Derby -Witek Park [Directions] | TBA | ||
| TBA | JV Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | TBA | ||
| TBA | JV Girls Soccer | Naugatuck | Away - Breen Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Derby | Home - OHS Soccer Field-West [Directions] | TBA | ||
| TBA | JV Softball | Wilby | Home - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Wolcott | Home - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Woodland | Away - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | WCA | Home - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Crosby | Away - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Seymour | Away - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Home - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | TBA | ||
| Mon., 7/3 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 6:00 p.m. | ||
| Wed., 7/5 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 6:00 p.m. | ||
| Mon., 7/10 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 6:00 p.m. | ||
| Wed., 7/12 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 6:00 p.m. | ||
| Mon., 7/17 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 6:00 p.m. | ||
| Wed., 7/19 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 6:00 p.m. | ||
| Mon., 7/24 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Tue., 7/25 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Tue., 7/25 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Wed., 7/26 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Thu., 7/27 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Fri., 7/28 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Mon., 7/31 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 6:00 p.m. | ||
| Tue., 8/1 | Miscellaneous Events | Oxford Youth Football & Cheer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Wed., 8/2 | Miscellaneous Events | Oxford Youth Football & Cheer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Wed., 8/2 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 7:00 p.m. | ||
| Thu., 8/3 | Miscellaneous Events | Oxford Youth Football & Cheer | - OHS Wolverine Field (Turf) | 5:00 p.m. | ||
| Sat., 8/5 | Miscellaneous Events | Oxford Youth Soccer | - OHS Wolverine Field (Turf) | 2:00 p.m. | ||
| Sat., 8/26 | V Football | Warde and Nonnewaug | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Mon., 8/28 | V Boys Soccer | Woodland (Scrim.) | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Tue., 8/29 | V Girls Soccer | Jonathan Law (Scrim.) | Home - OHS Wolverine Field (Turf) [Directions] | 3:30 p.m. | ||
| Wed., 8/30 | V Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:00 p.m. | ||
| Wed., 8/30 | JV Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:00 p.m. | ||
| Thu., 8/31 | V Football | Amity (Scrim.) | Home - OHS Wolverine Field (Turf) [Directions] | 5:00 p.m. | ||
| Fri., 9/1 | FM Football | Amity (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Fri., 9/1 | V Boys Soccer | Platt Tech (Scrim.) | Away - Platt Tech soccer field [Directions] | 3:45 p.m. | ||
| Fri., 9/1 | V Girls Volleyball | Staples (Scrim.) | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/1 | JV Girls Volleyball | Staples (Scrim.) | Home - OHS-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Shelton Boys Soccer Jamboree | Away | 2:00 p.m. | ||
| Tue., 9/5 | V Girls Soccer | Nonnewaug (Scrim.) | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Thu., 9/7 | FM Football | Holy Cross (Scrim.) | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 9/8 | V Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 16-37 | |
| Fri., 9/8 | V Boys Soccer | Crosby | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/8 | V Girls Soccer | Derby | Away - Derby -Witek Park [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 9/8 | V Girls Volleyball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Fri., 9/8 | JV Girls Volleyball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/9 | JV Boys Soccer | Crosby | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Tue., 9/12 | V Boys Cross Country | Wolcott, Holy Cross, WCA | Home - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | T 2-2 | |
| Tue., 9/12 | V Girls Cross Country | Wolcott, Holy Cross, WCA | Home - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Soccer | Wolcott | Home - OHS Wolverine Field (Turf) [Directions] | 7:00 p.m. | L 3-6 | |
| Tue., 9/12 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:00 p.m. | ||
| Tue., 9/12 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 5:30 p.m. | L 2-3 | |
| Tue., 9/12 | JV Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | JV Boys Soccer | Wolcott | Away - Wolcott HS, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 9/13 | JV Girls Soccer | Wolcott | Home - OHS Soccer Field-West [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | V Girls Volleyball | Nonnewaug | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 9/13 | JV Girls Volleyball | Nonnewaug | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Football | Sacred Heart | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 40-12 | |
| Thu., 9/14 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/15 | V Boys Soccer | Torrington | Home - OHS Wolverine Field (Turf) [Directions] | 4:00 p.m. | L 2-5 | |
| Fri., 9/15 | V Girls Swimming and Diving | Seymour | Away - Seymour HS [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | V Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 5:00 p.m. | L 2-3 | |
| Fri., 9/15 | JV Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Sat., 9/16 | V Boys Cross Country | Wilton Invitational | Away | 9:30 a.m. | ||
| Sat., 9/16 | FM Football | Sacred Heart | Away - Municipal Stadium | 10:00 a.m. | ||
| Sat., 9/16 | JV Boys Soccer | Torrington | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 9/16 | V Girls Cross Country | Wilton Invitational | Away | 9:30 a.m. | ||
| Mon., 9/18 | V Girls Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 4-2 | |
| Mon., 9/18 | V Girls Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 9/18 | JV Girls Volleyball | Bassick | Away [Directions] | 4:00 p.m. | ||
| Mon., 9/18 | Unified Sports Soccer | Nonnewaug | Away [Directions] | 2:30 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Derby, Torrington, Kennedy | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 6:30 p.m. | L 1-2 | |
| Tue., 9/19 | V Girls Cross Country | Derby, Torrington, Kennedy | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Girls Swimming and Diving | Sacred Heart | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Volleyball | Ansonia | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Tue., 9/19 | JV Girls Volleyball | Ansonia | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | JV Boys Soccer | Seymour | Away - Seymour High Lower Field [Directions] | 3:45 p.m. | ||
| Wed., 9/20 | V Girls Soccer | New Fairfield | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 0-5 | |
| Wed., 9/20 | JV Girls Soccer | New Fairfield | Home - OHS Soccer Field-West [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 7:00 p.m. | L 0-43 | |
| Fri., 9/22 | V Boys Soccer | Kennedy | Away - West Side MS [Directions] | 3:45 p.m. | L 2-3 | |
| Fri., 9/22 | V Girls Soccer | Ansonia | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | W 8-0 | |
| Fri., 9/22 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/22 | JV Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Sat., 9/23 | V Boys Cross Country | Winding Trails Invitational | Away | 9:00 a.m. | ||
| Sat., 9/23 | FM Football | Torrington | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | JV Boys Soccer | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Girls Cross Country | Winding Trails Invitational | Away | 9:00 a.m. | ||
| Tue., 9/26 | V Boys Cross Country | Wilby, Naugatuck, Sacred Heart | Away - Bucks Hill (Montoe) Park [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Holy Cross | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 3-2 | |
| Tue., 9/26 | V Girls Cross Country | Wilby, Naugatuck, Sacred Heart | Away - Bucks Hill (Montoe) Park [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Soccer | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | L 1-5 | |
| Tue., 9/26 | V Girls Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 7:00 p.m. | ||
| Tue., 9/26 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:45 p.m. | W 3-0 | |
| Tue., 9/26 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | ||
| Tue., 9/26 | Unified Sports Soccer | WCA | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Wed., 9/27 | JV Boys Soccer | Holy Cross | Home - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Thu., 9/28 | V Girls Soccer | Watertown | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | T 1-1 | |
| Fri., 9/29 | V Football | Crosby | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 40-50 | |
| Fri., 9/29 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | L 1-4 | |
| Fri., 9/29 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/29 | V Girls Volleyball | Torrington | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 9/29 | JV Girls Volleyball | Torrington | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | JV Boys Soccer | Watertown | Away - Swift MS [Directions] | 10:00 a.m. | ||
| Sat., 9/30 | JV Girls Soccer | Watertown | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Mon., 10/2 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:15 p.m. | W 7-0 | |
| Mon., 10/2 | V Girls Volleyball | Bassick | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/2 | JV Girls Volleyball | Bassick | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Woodland, Watertown, Ansonia | Home - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Woodland, Watertown, Ansonia | Home - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Soccer | St. Paul Catholic | Home - OHS Wolverine Field (Turf) [Directions] | 7:00 p.m. | L 2-5 | |
| Tue., 10/3 | V Girls Volleyball | Wolcott | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 10/3 | JV Girls Volleyball | Wolcott | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:15 p.m. | ||
| Wed., 10/4 | JV Girls Soccer | St. Paul Catholic | Home - OHS Soccer Field-West [Directions] | 4:15 p.m. | ||
| Wed., 10/4 | V Girls Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | ||
| Thu., 10/5 | Unified Sports Soccer | Torrington | Away [Directions] | 3:00 p.m. | ||
| Fri., 10/6 | V Football | Woodland | Away - Woodland Football Field [Directions] | 6:30 p.m. | W 42-14 | |
| Fri., 10/6 | V Boys Soccer | Ansonia | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 2-1 | |
| Fri., 10/6 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | W 4-0 | |
| Fri., 10/6 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - OHS Pool [Directions] | 4:30 p.m. | ||
| Fri., 10/6 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 5:30 p.m. | L 2-3 | |
| Fri., 10/6 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 4:00 p.m. | ||
| Sat., 10/7 | V Boys Cross Country | Wikham Park Invitational | Away | 9:00 a.m. | ||
| Sat., 10/7 | FM Football | Woodland | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | JV Boys Soccer | Ansonia | Home - OHS Soccer Field-West [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | V Girls Cross Country | Wickham Park Invitational | Away | 9:00 a.m. | ||
| Tue., 10/10 | V Boys Cross Country | Seymour, Crosby, St. Paul Catholic | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Woodland | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 4-1 | |
| Tue., 10/10 | V Girls Cross Country | Seymour, Crosby, St. Paul Catholic | Away - Seymour H.S. [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Girls Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | L 1-6 | |
| Tue., 10/10 | V Girls Volleyball | Holy Cross | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Tue., 10/10 | JV Girls Volleyball | Holy Cross | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | JV Boys Soccer | Woodland | Home - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Wed., 10/11 | JV Girls Soccer | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | JV Girls Soccer | Seymour | Home - OHS Soccer Field-West [Directions] | 4:30 p.m. | ||
| Thu., 10/12 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 10/12 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | Unified Sports Soccer | Bassick | Home - OHS-Main Gym [Directions] | 3:15 p.m. | ||
| Fri., 10/13 | V Boys Soccer | WCA | Away - Municipal Stadium [Directions] | 6:00 p.m. | W 4-0 | |
| Fri., 10/13 | V Girls Soccer | Seymour | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | T 3-3 | |
| Fri., 10/13 | V Girls Swimming and Diving | Kennedy | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Naugatuck | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Fri., 10/13 | JV Girls Volleyball | Naugatuck | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Soccer | Immaculate | Away - Mustang Valley [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/16 | JV Girls Soccer | Immaculate | Away - Immaculate HS [Directions] | 3:45 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:15 p.m. | W 3-0 | |
| Mon., 10/16 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:45 p.m. | ||
| Mon., 10/16 | Unified Sports Soccer | Wilby | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Wilby | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 4-2 | |
| Tue., 10/17 | V Girls Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 5:00 p.m. | ||
| Tue., 10/17 | Unified Sports Soccer | Torrington | Away - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | NVL Championships | Away - Veterans Park | TBA | ||
| Wed., 10/18 | V Boys Soccer | Bassick | Away - Went Field [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 10/18 | V Girls Cross Country | NVL Championship | Away - Veterans Park | TBA | ||
| Wed., 10/18 | V Girls Volleyball | Daniel Hand | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Wed., 10/18 | JV Girls Volleyball | Daniel Hand | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Boys Soccer | Naugatuck | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 2-0 | |
| Fri., 10/20 | V Football | Derby | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 26-32 | Homecoming |
| Fri., 10/20 | V Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | L 1-2 | |
| Fri., 10/20 | V Girls Swimming and Diving | Watertown | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/20 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 3:30 p.m. | ||
| Sat., 10/21 | FM Football | Derby | Home - OHS Wolverine Field (Turf) [Directions] | 10:30 a.m. | ||
| Sat., 10/21 | JV Boys Soccer | Naugatuck | Home - OHS Soccer Field-West [Directions] | 10:00 a.m. | ||
| Mon., 10/23 | V Boys Soccer | Sacred Heart | Away - Municipal Stadium | 7:30 p.m. | T 2-2 | |
| Mon., 10/23 | V Girls Soccer | Sacred Heart | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | W 6-0 | |
| Mon., 10/23 | V Girls Volleyball | Crosby | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/23 | JV Girls Volleyball | Crosby | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | Unified Sports Soccer | Wolcott | Away [Directions] | 3:00 p.m. | ||
| Wed., 10/25 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 4:30 p.m. | W 7-3 | |
| Wed., 10/25 | V Girls Soccer | Derby | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 6-0 | |
| Wed., 10/25 | V Girls Volleyball | Seymour | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 10/25 | JV Girls Volleyball | Seymour | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | JV Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | V Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:30 p.m. | L 34-58 | |
| Fri., 10/27 | JV Girls Volleyball | JV NVL Tournament | Away | 3:30 p.m. | ||
| Sat., 10/28 | V Boys Cross Country | CIAC Championships | Away | TBA | ||
| Sat., 10/28 | FM Football | Amistad | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Championship | Away | TBA | ||
| Tue., 10/31 | V Girls Soccer | Foran (Scrim.) | Away [Directions] | 5:30 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | NVL Trials | Away [Directions] | 4:00 p.m. | ||
| Thu., 11/2 | V Girls Swimming and Diving | NVL Diving Championships | Away [Directions] | 4:30 p.m. | ||
| Fri., 11/3 | V Football | Wilby | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 43-0 | |
| Fri., 11/3 | V Girls Swimming and Diving | NVL Swimming Championships | Away [Directions] | 6:00 p.m. | ||
| Sat., 11/4 | V Boys Cross Country | State Open | Away | TBA | ||
| Sat., 11/4 | FM Football | Seymour | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 11/4 | V Girls Cross Country | State Open Championship | Away | TBA | ||
| Mon., 11/6 | V Girls Volleyball | Plainfield | Away [Directions] | 5:00 p.m. | ||
| Tue., 11/7 | V Girls Soccer | Nonnewaug | Away [Directions] | 2:00 p.m. | ||
| Thu., 11/9 | V Girls Swimming and Diving | Class S Diving Championships | Away [Directions] | 4:30 p.m. | ||
| Thu., 11/9 | Unified Sports Soccer | Wilby | Away [Directions] | 3:00 p.m. | ||
| Fri., 11/10 | V Football | Seymour | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 19-38 | |
| Sat., 11/11 | FM Football | Brookfield | Away [Directions] | 10:00 a.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | Class S Qualifier | Away [Directions] | 2:00 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | Class S Swimming Championship | Away | 6:00 p.m. | ||
| Sat., 11/18 | FM Football | St. Paul Catholic | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Wed., 11/22 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | L 22-44 | |
| Sat., 12/2 | V Wrestling | Shelton (Scrim.) | Away - Shelton HS - Auxillary Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/2 | V Girls Ice Hockey | Guilford Jamboree | Away - DiLungo Memorial Ice Rink, East Haven | 5:45 p.m. | ||
| Sun., 12/3 | V Girls Ice Hockey | New Canaan (Scrim.) | Home - The Rinks at Shelton [Directions] | 6:00 p.m. | ||
| Tue., 12/5 | V Girls Basketball | Amity (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Wed., 12/6 | V Boys Ice Hockey | Glastonbury (Scrim.) | Home - Bennett Rink [Directions] | 6:30 p.m. | ||
| Wed., 12/6 | V Girls Basketball | North Branford (Scrim.) | Away - North Branford HS [Directions] | 4:00 p.m. | ||
| Thu., 12/7 | V Boys Basketball | Immaculate (Scrim.) | Home - OHS-Main Gym [Directions] | 5:45 p.m. | ||
| Fri., 12/8 | V Boys Ice Hockey | St. Lukes (Scrim.) | Home - Bennett Rink [Directions] | 4:00 p.m. | ||
| Fri., 12/8 | V Girls Basketball | Shepaug Valley (Scrim.) | Home - OHS-Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 12/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - The Rinks at Shelton [Directions] | 5:30 p.m. | L 6-1 | |
| Tue., 12/12 | V Girls Basketball | Shelton | Away - Shelton HS Gym [Directions] | 7:00 p.m. | L 14-38 | |
| Wed., 12/13 | V Boys Basketball | O'Brien Tech (Scrim.) | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/13 | V Boys Ice Hockey | Jamboree | Home - Bennett Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/13 | V Girls Ice Hockey | Hamden Coop | Home - The Rinks at Shelton [Directions] | 5:00 p.m. | L 0-16 | |
| Sat., 12/16 | V Boys Basketball | Gilbert (Scrim.) | Home - OHS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/16 | V Wrestling | Derby Invitational | Away | 10:00 a.m. | ||
| Sat., 12/16 | V Wrestling | Derby Invitational | Home - Derby HS Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | 1:00 p.m. | L 0-7 | |
| Sun., 12/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - The Rinks at Shelton [Directions] | 6:30 p.m. | L 0-8 | |
| Mon., 12/18 | V Boys Indoor Track | Relay Rust Buster Invitational | Away - SCSU | 5:00 p.m. | ||
| Mon., 12/18 | V Boys Indoor Track | Relay Rust Buster Invitational | Away | 5:00 p.m. | @ SCSU Moore Fieldhouse | |
| Mon., 12/18 | V Girls Basketball | Westbrook | Home - OHS-Main Gym [Directions] | 6:30 p.m. | W Forfeit | |
| Mon., 12/18 | V Girls Indoor Track | Relay Rust Buster Invitational | Away - SCSU | 5:00 p.m. | ||
| Mon., 12/18 | V Girls Indoor Track | Relay Rust Buster Invitational | Away | 5:00 p.m. | @ SCSU Moore Fieldhouse | |
| Tue., 12/19 | V Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 7:00 p.m. | L 46-82 | |
| Tue., 12/19 | JV Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | ||
| Tue., 12/19 | V Boys Swimming and Diving | Woodland | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 12/19 | V Girls Basketball | WCA | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 42-48 | |
| Tue., 12/19 | Unified Sports Basketball | WCA | Away [Directions] | 2:45 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Greenwich | Home - Bennett Rink [Directions] | 6:30 p.m. | L 5-2 | |
| Wed., 12/20 | V Wrestling | Thomaston | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/20 | V Wrestling | Northwestern | Away - Northwestern HS [Directions] | 6:00 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | 4:00 p.m. | L 0-9 | |
| Thu., 12/21 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | L 33-37 | |
| Thu., 12/21 | JV Girls Basketball | Torrington | Away - Torrington HS [Directions] | Cancelled | Cancelled | |
| Thu., 12/21 | Miscellaneous Events | Football Senior Center Visit | 12:00 p.m. | Pick up at 1:30 pm | ||
| Thu., 12/21 | Unified Sports Basketball | Cheshire | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Bennett Rink [Directions] | 1:00 p.m. | L 4-7 | |
| Sat., 12/23 | V Boys Indoor Track | Hillhouse Winter Relays | Away | 9:00 a.m. | @ Floyd Little Athletic Center | |
| Sat., 12/23 | V Girls Indoor Track | Hillhouse Winter Relays | Away | 9:00 a.m. | @ Floyd Little Athletic Center | |
| Wed., 12/27 | V Boys Basketball | Mt. Everett (MA) | Away [Directions] | 5:30 p.m. | W 60-29 | |
| Wed., 12/27 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 5:30 p.m. | L 2-9 | |
| Wed., 12/27 | V Wrestling | Shelton, Fairfield Prep | Away - Shelton HS Gym [Directions] | 10:00 a.m. | ||
| Wed., 12/27 | V Wrestling | Terryville-Thomaston | Away - New Terryville HS [Directions] | 6:00 p.m. | ||
| Wed., 12/27 | V Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:00 p.m. | L 30-33 | |
| Thu., 12/28 | V Boys Indoor Track | Wilton Wright Invitational | Away - SCSU | 12:00 p.m. | ||
| Thu., 12/28 | V Girls Indoor Track | Wilton Wright Invitational | Away - SCSU | 12:00 p.m. | ||
| Fri., 12/29 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 47-55 | |
| Fri., 12/29 | V Boys Indoor Track | 2nd Annual Hillhouse Track and Field Qualifier | Away | 10:00 a.m. | @ Floyd Little Athletic Complex | |
| Fri., 12/29 | V Girls Basketball | Wilton (Scrim.) | Away - Nicholas Zeoli Field House [Directions] | Cancelled | Cancelled | |
| Fri., 12/29 | V Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 2:00 p.m. | L 43-47 | |
| Fri., 12/29 | V Girls Indoor Track | 2nd Hillhouse Track and Field Qualifier | Away | 10:00 a.m. | @ Floyd Little Athletic Center | |
| Sat., 12/30 | V Boys Ice Hockey | St. Joseph | Home - Bennett Rink [Directions] | 1:00 p.m. | W 7-5 | |
| Sat., 12/30 | V Boys Indoor Track | 2nd Annual Hillhouse Track and Field Qualifier | Away | 10:00 a.m. | @ Floyd Little Athletic Center | |
| Sat., 12/30 | V Boys Indoor Track | Wintergreen Invitational | Away - SCSU | 9:00 a.m. | ||
| Sat., 12/30 | V Wrestling | Somers, Fairfield Prep | Away - Somers HS [Directions] | 10:00 a.m. | ||
| Sat., 12/30 | V Girls Indoor Track | 2nd Hillhouse Track and Field Qualifier | Away | 10:00 a.m. | @ Floyd Little Athletic Center | |
| Sat., 12/30 | V Girls Indoor Track | Wintergreen Invitational | Away - SCSU | 9:00 a.m. | ||
| Wed., 1/3 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 39-102 | |
| Wed., 1/3 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Simsbury | Home - Bennett Rink [Directions] | 6:30 p.m. | W 6-3 | |
| Wed., 1/3 | V Wrestling | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/3 | V Wrestling | Northwestern | Away - Northwestern Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Seymour | Home - OHS-Main Gym [Directions] | 7:00 p.m. | L 46-56 | |
| Fri., 1/5 | JV Girls Basketball | Derby | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Sat., 1/6 | V Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 3:00 p.m. | L 53-72 | |
| Sat., 1/6 | V Boys Ice Hockey | Guilford | Home - Bennett Rink [Directions] | 1:00 p.m. | L 3-8 | |
| Sat., 1/6 | V Wrestling | Lawless Tournament | Away - Nonnewaug HS | 9:00 a.m. | ||
| Sat., 1/6 | V Wrestling | Lawless Duals | Away | 9:00 a.m. | ||
| Sat., 1/6 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 1:00 p.m. | L 45-49 | |
| Sat., 1/6 | V Girls Gymnastics | Pomperaug Invitational | Away | 10:00 a.m. | 129.6 | |
| Sun., 1/7 | V Boys Indoor Track | 2nd Annual James Barber Invitational | Away | TBA | @ Moore Fieldhouse - SCSU | |
| Sun., 1/7 | V Boys Indoor Track | James Barber Invitational | Away - SCSU | TBA | ||
| Sun., 1/7 | V Girls Indoor Track | 2nd Annual James Barber Invitational | Away | TBA | @ Moore Fieldhouse - SCSU | |
| Sun., 1/7 | V Girls Indoor Track | James Barber Invitational | Away - SCSU | TBA | ||
| Tue., 1/9 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | ||
| Tue., 1/9 | V Girls Gymnastics | New Milford, Joel Barlow, Newtown | Away [Directions] | 5:00 p.m. | 127.25 | |
| Wed., 1/10 | V Boys Basketball | Torrington | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 43-78 | |
| Wed., 1/10 | JV Boys Basketball | Torrington | Home - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 1/10 | V Boys Ice Hockey | Amity | Home - Bennett Rink - West Haven [Directions] | 6:30 p.m. | L 1-3 | |
| Wed., 1/10 | V Wrestling | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/10 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 6:30 p.m. | L 24-47 | |
| Wed., 1/10 | Unified Sports Basketball | Wolcott | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Thu., 1/11 | V Boys Swimming and Diving | Crosby/WCA | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Thu., 1/11 | V Wrestling | Oxford | Home - Derby HS Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 1/11 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby HS Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 1/12 | V Boys Basketball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 44-76 | |
| Fri., 1/12 | JV Boys Basketball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 1/12 | V Boys Swimming and Diving | Bethel | Home - OHS Pool [Directions] | 5:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | L 37-60 | |
| Sat., 1/13 | V Boys Ice Hockey | East Haven Coop | Home - Bennett Rink [Directions] | 11:30 a.m. | L 1-2(OT) | |
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invitational | Away | 9:00 a.m. | @ Floyd Little Athletic Center | |
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invitational | Away - Hillhouse HS | TBA | ||
| Sat., 1/13 | V Wrestling | Canton, Weston, Farmington, Northwestern | Away - Canton H.S. [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | Winter Dance Team | Woodland Dance Competition | Away | 4:00 p.m. | ||
| Sat., 1/13 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 1-6 | |
| Sat., 1/13 | V Girls Indoor Track | SCC Coaches Invitational | Away | 9:00 a.m. | @ Flyod Little Athletic Complex | |
| Sat., 1/13 | V Girls Indoor Track | SCC Coaches Invitational | Away - Hillhouse HS | TBA | ||
| Mon., 1/15 | V Boys Ice Hockey | Harvey School (NY) | Home - Bennett Rink [Directions] | 4:00 p.m. | T 2-2 (OT) | |
| Tue., 1/16 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 7:00 p.m. | ||
| Tue., 1/16 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | 7:30 p.m. | L 0-3 | |
| Wed., 1/17 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | 6:00 p.m. | L 0-8 | |
| Thu., 1/18 | V Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 7:00 p.m. | L 52-53 | |
| Thu., 1/18 | JV Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/18 | V Wrestling | Gilbert/Torrington | Home - Derby HS Gymnasium [Directions] | 7:00 p.m. | ||
| Thu., 1/18 | V Girls Basketball | Woodland | Home - OHS-Main Gym [Directions] | 5:00 p.m. | W 47-37 | |
| Fri., 1/19 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | L 57-72 | |
| Fri., 1/19 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | V Boys Indoor Track | Yale High School Invitational | Away | TBA | ||
| Fri., 1/19 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Kennedy | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 46-22 | |
| Fri., 1/19 | V Girls Ice Hockey | Guilford Coop | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 1/19 | V Girls Indoor Track | Yale High School Invitational | Away | TBA | ||
| Sat., 1/20 | V Wrestling | Eagle Classic | Away - East Catholic HS | 9:00 a.m. | ||
| Sat., 1/20 | V Competitive Cheerleading | Seymour Competition | Away | 12:00 p.m. | ||
| Sat., 1/20 | Miscellaneous Events | GBBall Quinnipiac Game | Away | 12:30 p.m. | ||
| Mon., 1/22 | V Girls Gymnastics | Jonathan Law, Daniel Hand, Newtown | Away - Jonathan Law HS Old Gym [Directions] | 6:00 p.m. | 132.7 | |
| Mon., 1/22 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 8:30 p.m. | W 5-1 | |
| Tue., 1/23 | V Boys Swimming and Diving | Watertown | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | W 40-22 | |
| Tue., 1/23 | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | Cancelled | Cancelled | |
| Wed., 1/24 | V Boys Basketball | Ansonia | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 49-46 | |
| Wed., 1/24 | JV Boys Basketball | Ansonia | Home - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Hamden | Home - Bennett Rink [Directions] | 6:15 p.m. | L 4-1 | |
| Wed., 1/24 | V Wrestling | Nonnewaug | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/25 | V Wrestling | Terryville-Thomaston | Away - New Terryville HS [Directions] | 6:30 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | W 53-41 | |
| Fri., 1/26 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Watertown | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 42-33 | |
| Fri., 1/26 | JV Girls Basketball | Watertown | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Fri., 1/26 | V Girls Ice Hockey | Daniel Hand Coop | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 1-6 | |
| Sat., 1/27 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Bennett Rink [Directions] | 1:00 p.m. | L 2-1 (OT) | |
| Sat., 1/27 | V Wrestling | Doc Meyers Classic | Away - Rocky Hill HS | 9:00 a.m. | ||
| Sat., 1/27 | V Wrestling | Doc Meyers Tournament - Rocky Hill | Away | 9:30 a.m. | ||
| Sat., 1/27 | V Competitive Cheerleading | Quinnipiac Competition | Away | 1:30 p.m. | ||
| Sat., 1/27 | Winter Dance Team | Quinnipiac Competition | Away | 4:30 p.m. | ||
| Sun., 1/28 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - The Rinks at Shelton [Directions] | 8:15 p.m. | L 1-5 | |
| Mon., 1/29 | V Boys Indoor Track | NVL Championships | Away - Hillhouse HS | 4:30 p.m. | ||
| Mon., 1/29 | V Boys Indoor Track | NVL Championships | Away | 4:30 p.m. | @ Flyod Little Athletic Complex | |
| Mon., 1/29 | V Girls Indoor Track | NVL Championships | Away - Hillhouse HS | 4:30 p.m. | ||
| Mon., 1/29 | V Girls Indoor Track | NVL Championships | Away | 4:30 p.m. | @ Floyd Little Athletic Complex | |
| Mon., 1/29 | Unified Sports Basketball | Nonnewaug | Away [Directions] | 2:30 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Seymour | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Wilby | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 52-16 | |
| Wed., 1/31 | V Boys Basketball | Wilby | Away - Wilby H.S. [Directions] | 7:00 p.m. | L 38-76 | |
| Wed., 1/31 | JV Boys Basketball | Wilby | Away - Wilby H.S. [Directions] | 5:15 p.m. | ||
| Wed., 1/31 | V Wrestling | Notre Dame-West Haven | Away [Directions] | Cancelled | Cancelled | |
| Wed., 1/31 | V Wrestling | Gilbert/Torrington | Home - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/31 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | 7:30 p.m. | L 0-2 | |
| Thu., 2/1 | V Girls Ice Hockey | Lauralton Hall | Away - Wonderland of Ice [Directions] | 3:15 p.m. | W 1-0 (Forfeit( | |
| Fri., 2/2 | V Boys Basketball | Derby | Home - OHS-Main Gym [Directions] | 7:15 p.m. | L 54-66 | |
| Fri., 2/2 | V Girls Basketball | Derby | Home - OHS-Main Gym [Directions] | 5:30 p.m. | W 42-30 | |
| Fri., 2/2 | JV Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | Cancelled | Cancelled | |
| Fri., 2/2 | V Girls Gymnastics | Newtown, Joel Barlow | Away - Gymnastics & Cheer Academy [Directions] | 5:30 p.m. | 132.05 | |
| Fri., 2/2 | V Girls Ice Hockey | West Haven/SHA | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 0-6 | |
| Sat., 2/3 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Bennett Rink [Directions] | 1:00 p.m. | L 1-4 | |
| Sat., 2/3 | V Wrestling | Morgan, Griswold/Wheeler, Granby Memorial, Canton | Away - Morgan HS [Directions] | 9:00 a.m. | ||
| Sat., 2/3 | V Wrestling | Foran Duals | Away | 9:00 a.m. | ||
| Mon., 2/5 | V Boys Indoor Track | Capital Prep State Qualifier | Away | 5:00 p.m. | ||
| Mon., 2/5 | V Girls Indoor Track | Capital Prep State Qualifier | Away | 5:00 p.m. | ||
| Tue., 2/6 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 37-80 | |
| Tue., 2/6 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Wilby/Kaynor | Home - OHS Pool [Directions] | 5:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 30-46 | |
| Wed., 2/7 | Unified Sports Basketball | IPPI Learning Academy | Away | 3:00 p.m. | ||
| Thu., 2/8 | V Wrestling | Nonnewaug | Home - OHS-Main Gym [Directions] | 5:00 p.m. | Senior Night | |
| Thu., 2/8 | V Wrestling | St. Paul Catholic | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 2/8 | V Girls Gymnastics | SWC Championship | Away [Directions] | 5:00 p.m. | 135.7 | |
| Fri., 2/9 | V Boys Basketball | Seymour | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 50-83 | |
| Fri., 2/9 | JV Boys Basketball | Seymour | Home - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 51-66 | |
| Fri., 2/9 | V Girls Ice Hockey | Branford | Home - The Rinks at Shelton [Directions] | 5:30 p.m. | L 0-4 | |
| Sat., 2/10 | V Boys Ice Hockey | Xavier | Home - Bennett Rink [Directions] | 1:00 p.m. | L 0-6 | |
| Sat., 2/10 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC State Tournament | Away | 4:30 p.m. | @ Floyd Little Athletic Complex | |
| Sat., 2/10 | V Wrestling | BL/NVL Championships | Away [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Wrestling | Berkshire/Valley Tournament | Away - Northwestern HS | 9:00 a.m. | ||
| Sat., 2/10 | V Competitive Cheerleading | Watertown Competition | Away [Directions] | 10:30 a.m. | ||
| Sat., 2/10 | Winter Dance Team | Fairfield Warde Dance Jam | Away [Directions] | 2:00 p.m. | @ Fairfield Warde HS | |
| Sat., 2/10 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 2/10 | V Girls Indoor Track | CIAC State Championship | Away | 4:30 p.m. | @ Floyd Little Athletic Complex | |
| Sun., 2/11 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | 7:00 p.m. | L 0-8 | |
| Mon., 2/12 | V Boys Basketball | Wolcott | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 39-59 | |
| Mon., 2/12 | JV Boys Basketball | Wolcott | Home - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Mon., 2/12 | V Boys Ice Hockey | North Rockland (NY) | Home - Bennett Rink [Directions] | 5:00 p.m. | L 10-5 | |
| Mon., 2/12 | V Girls Basketball | Wolcott | Away - Wolcott HS [Directions] | 6:00 p.m. | W 45-41 | |
| Tue., 2/13 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | ||
| Tue., 2/13 | V Girls Gymnastics | New Milford, Newtown | Away [Directions] | 5:00 p.m. | 131.50 | |
| Tue., 2/13 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | 6:30 p.m. | L 0-5 | |
| Wed., 2/14 | V Boys Ice Hockey | Milford Coop | Home - Bennett Rink [Directions] | 6:30 p.m. | W 6-2 | |
| Wed., 2/14 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | 7:00 p.m. | L 0-6 | |
| Wed., 2/14 | Unified Sports Basketball | Ansonia | Home - OHS-Main Gym [Directions] | 2:15 p.m. | ||
| Thu., 2/15 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 43-54 | |
| Thu., 2/15 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Thu., 2/15 | V Girls Basketball | Ansonia | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 42-39 | |
| Thu., 2/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 6:30 p.m. | L 2-7 | |
| Thu., 2/15 | Unified Sports Basketball | Wolcott | Away [Directions] | 3:30 p.m. | ||
| Fri., 2/16 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | ||
| Fri., 2/16 | V Wrestling | Class S State Championships | Away - Windham HS | 4:00 p.m. | ||
| Fri., 2/16 | V Girls Gymnastics | Newtown, Fairfield Ludlowe, Nonnewaug, Pomperaug | Away - Auxiliary Gym [Directions] | 6:00 p.m. | 130.45 | |
| Fri., 2/16 | V Girls Ice Hockey | Lauralton Hall | Home - The Rinks at Shelton [Directions] | TBA | W Forfeit | |
| Sat., 2/17 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | 4:00 p.m. | L 2-5 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/17 | V Wrestling | Class S State Championships | Away - Windham HS | 9:00 a.m. | ||
| Sat., 2/17 | V Competitive Cheerleading | NVL Championship | Away [Directions] | 10:30 a.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Crosby | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 53-96 | |
| Mon., 2/19 | JV Boys Basketball | Crosby | Home - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Mon., 2/19 | V Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | 2:00 p.m. | W 4-1 | |
| Mon., 2/19 | V Girls Gymnastics | Pomperaug, Nonnewaug, Newtown | Away - Kinetic Kids [Directions] | 10:00 a.m.p.m. | 126.55 | |
| Wed., 2/21 | V Boys Basketball | Sacred Heart | Home - OHS-Main Gym [Directions] | 5:30 p.m. | L 46-93 | |
| Wed., 2/21 | Winter Dance Team | NVL Championship | Away [Directions] | 4:30 p.m. | @ Woodland HS | |
| Fri., 2/23 | V Boys Basketball | Naugatuck | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 45-50 | |
| Fri., 2/23 | JV Boys Basketball | Naugatuck | Home - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 2/23 | V Wrestling | State Open Championships | Away - Floyd Little Athletic Center, NH | 3:30 p.m. | ||
| Sat., 2/24 | V Boys Ice Hockey | Glastonbury | Away - Trinity College [Directions] | 7:30 p.m. | L 1-2 | |
| Sat., 2/24 | V Boys Indoor Track | Dream Big Pentathalon Invitational | Away - The Armory | TBA | ||
| Sat., 2/24 | V Wrestling | State Open Championships | Away - Floyd Little Athletic Center, NH | 9:00 a.m. | ||
| Sat., 2/24 | V Competitive Cheerleading | Woodland Competition | Away [Directions] | 10:30 a.m. | ||
| Sat., 2/24 | Winter Dance Team | State Championship | Away [Directions] | 9:00 a.m. | ||
| Sat., 2/24 | V Girls Gymnastics | CIAC Class Meet | Away | TBA | ||
| Sat., 2/24 | V Girls Indoor Track | Dream Big Pentathalon Invitational | Away - The Armory | TBA | ||
| Mon., 2/26 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | CIAC State 1st Round | |
| Tue., 2/27 | V Boys Swimming and Diving | NVL Trials | Away [Directions] | 4:00 p.m. | ||
| Wed., 2/28 | V Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | 7:00 p.m. | L 3-4(OT) | |
| Wed., 2/28 | V Boys Swimming and Diving | NVL Diving Championship | Away [Directions] | 6:00 p.m. | ||
| Wed., 2/28 | Unified Sports Basketball | Wilby | Away [Directions] | 3:00 p.m. | ||
| Thu., 3/1 | V Boys Swimming and Diving | NVL Championship | Away [Directions] | 4:00 p.m. | ||
| Sat., 3/3 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/3 | V Competitive Cheerleading | State Championship | Away | 4:00 p.m. | ||
| Sat., 3/3 | V Girls Gymnastics | CIAC Open | Away | TBA | ||
| Sat., 3/3 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Thu., 3/8 | Unified Sports Basketball | Torrington | Away [Directions] | 3:00 p.m. | ||
| Sat., 3/10 | V Competitive Cheerleading | Team of the Year | Away [Directions] | 2:30 p.m. | ||
| Sat., 3/10 | V Competitive Cheerleading | Team of the Year Competition | Away | TBA | ||
| Sat., 3/10 | V Girls Gymnastics | New Englands | Away | TBA | ||
| Thu., 3/15 | Unified Sports Basketball | Wilby | Away [Directions] | 3:00 p.m. | ||
| Sat., 3/17 | V Competitive Cheerleading | Cheerleading Regional Competition | Away | TBA | ||
| Sat., 3/17 | V Competitive Cheerleading | Regional Competition | Away | TBA | ||
| Sat., 3/24 | V Baseball | Staples (Scrim.) | Away - Sportsplex in North Haven [Directions] | 1:30 p.m. | ||
| Sat., 3/24 | V Boys Volleyball | Oxford Round Robin Scrimmage | Home - OHS-Main Gym [Directions] | 9:00 a.m. | New Canaan, Newington and St. Josephs | |
| Tue., 3/27 | V Baseball | Masuk (Scrim.) | Home - OHS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 3/27 | V Softball | Lauralton Hall (Scrim.) | Away - Lauralton Hall Field [Directions] | 4:00 p.m. | ||
| Thu., 3/29 | V Boys Volleyball | Trumbull (Scrim.) | Home - Oxford Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/29 | V Softball | Trumbull (Scrim.) | Away - Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 3/31 | V Baseball | Pomperaug | Away - PHS Baseball Field [Directions] | 3:00 p.m. | W 8-5 | |
| Sat., 3/31 | JV Baseball | Pomperaug | Home - OHS Baseball Field [Directions] | 12:00 p.m. | ||
| Tue., 4/3 | V Boys Volleyball | Newtown | Home - OHS-Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 4/3 | JV Boys Volleyball | Newtown | Home - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 4/4 | V Boys Volleyball | Wolcott Tech | Home - OHS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/4 | JV Boys Volleyball | Wolcott Tech | Home - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 4/5 | V Boys Outdoor Track | Crosby, Watertown | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Thu., 4/5 | V Girls Outdoor Track | Crosby, Watertown | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Thu., 4/5 | V Softball | New Fairfield | Home - Oxford HS [Directions] | 4:15 p.m. | W 7-3 | |
| Fri., 4/6 | V Boys Volleyball | Amity | Home - OHS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/6 | JV Boys Volleyball | Amity | Home - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 4/7 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | 1:00 p.m. | L 7-5 | |
| Sat., 4/7 | JV Baseball | Wolcott | Away - Wolcott HS [Directions] | 3:00 p.m. | ||
| Sat., 4/7 | V Softball | Wolcott | Home - OHS Softball Field [Directions] | 3:00 p.m. | W 15-6 | |
| Mon., 4/9 | V Baseball | Watertown | Away - Deland Field [Directions] | 3:45 p.m. | L 3-0 | |
| Mon., 4/9 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Mon., 4/9 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 4/9 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/10 | V Softball | West Haven | Home - OHS Softball Field [Directions] | 3:45 p.m. | L 1-15 | |
| Wed., 4/11 | V Baseball | Torrington | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 2-1 | |
| Wed., 4/11 | V Boys Outdoor Track | Wilby, Derby | Home - OHS Track [Directions] | 3:30 p.m. | ||
| Wed., 4/11 | V Boys Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 4/11 | JV Boys Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/11 | V Girls Outdoor Track | Wilby, Derby | Home - OHS Track [Directions] | 3:30 p.m. | ||
| Wed., 4/11 | V Softball | Torrington | Away - Torrington HS [Directions] | 4:00 p.m. | W 6-4 | |
| Thu., 4/12 | JV Baseball | Torrington | Home - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/13 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:45 p.m. | L 3-0 | |
| Fri., 4/13 | V Boys Volleyball | St. Joseph | Home - OHS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/13 | JV Boys Volleyball | St. Joseph | Home - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 4/13 | V Softball | Ansonia | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 15-0 | |
| Sat., 4/14 | V Baseball | Wilby | Home - OHS Baseball Field [Directions] | 12:00 p.m. | W 10-0 (5) | |
| Sat., 4/14 | JV Baseball | Holy Cross | Away - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 4/14 | V Boys Outdoor Track | Torrington, Sacred Heart | Home - OHS Track [Directions] | 9:00 a.m. | ||
| Sat., 4/14 | V Girls Outdoor Track | Torrington, Sacred Heart | Home - OHS Track [Directions] | 9:00 a.m. | ||
| Sat., 4/14 | V Softball | Wilby | Home - OHS Softball Field [Directions] | 10:00 a.m. | W 20-0 | |
| Mon., 4/16 | V Boys Volleyball | Masuk | Home - OHS-Main Gym [Directions] | 3:30 p.m. | W 3-0 | |
| Mon., 4/16 | JV Boys Volleyball | Masuk | Home - OHS-Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 4/17 | V Softball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 4:00 p.m. | W 22-1 | |
| Tue., 4/17 | JV Softball | West Haven | Home - OHS Softball Field [Directions] | 12:00 p.m. | ||
| Wed., 4/18 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:30 p.m. | L 4-3 (8) | |
| Wed., 4/18 | V Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 4/18 | JV Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 4:30 p.m. | ||
| Wed., 4/18 | V Softball | Woodland | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 17-2 | |
| Fri., 4/20 | V Baseball | St. Paul Catholic | Home - OHS Baseball Field [Directions] | 3:45 p.m. | L 9-6 | |
| Fri., 4/20 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 3-4 | |
| Sat., 4/21 | V Baseball | Derby | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 14-0(5) | |
| Sat., 4/21 | JV Baseball | St. Paul Catholic | Home - OHS Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/21 | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 10:30 a.m. | ||
| Mon., 4/23 | V Baseball | Kennedy | Away - Waterville Park [Directions] | 3:45 p.m. | W 12-1(5) | |
| Mon., 4/23 | V Boys Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Mon., 4/23 | JV Boys Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/23 | V Softball | WCA | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 4/24 | V Baseball | Seymour | Away - French Park [Directions] | 3:30 p.m. | L 12-0(5) | |
| Tue., 4/24 | JV Baseball | Kennedy | Away - Waterville Park [Directions] | 3:45 p.m. | ||
| Tue., 4/24 | V Boys Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS [Directions] | 3:30 p.m. | ||
| Tue., 4/24 | V Girls Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS [Directions] | 3:30 p.m. | ||
| Tue., 4/24 | V Softball | Seymour | Home - OHS Softball Field [Directions] | 3:30 p.m. | L 6-8 | |
| Thu., 4/26 | JV Baseball | Seymour | Away - French Park [Directions] | 4:00 p.m. | ||
| Thu., 4/26 | V Boys Volleyball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 4/26 | JV Boys Volleyball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 4:00 p.m. | ||
| Thu., 4/26 | JV Softball | Seymour | Home - OHS Softball Field [Directions] | 3:30 p.m. | ||
| Sat., 4/28 | V Baseball | Holy Cross | Home - OHS Baseball Field [Directions] | 2:00 p.m. | L 16-3(5) | |
| Sat., 4/28 | JV Baseball | Holy Cross | Home - OHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/28 | V Softball | Holy Cross | Away - Holy Cross HS [Directions] | 2:00 p.m. | L 5-6(8) | |
| Sat., 4/28 | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | 12:00 p.m. | ||
| A request to make the following change(s) to the above event has been submitted by one of the schools involved, but has not yet been accepted by the other -- Change facility to | ||||||
| Mon., 4/30 | V Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | L 5-2 | |
| Mon., 4/30 | JV Baseball | Naugatuck | Home - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/30 | V Boys Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 4/30 | JV Boys Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 4/30 | V Softball | Naugatuck | Home - OHS Softball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 4/30 | Unified Sports Volleyball | Wilby | Home - OHS-Main Gym [Directions] | 3:15 p.m. | ||
| Tue., 5/1 | V Baseball | Lyman Hall | Away - Lyman Hall, Pat Wall Field [Directions] | 4:00 p.m. | L 7-3 | |
| Tue., 5/1 | JV Baseball | Lyman Hall | Away - Lyman Hall- Doolittle Park [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Boys Outdoor Track | St. Paul Catholic, Seymour | Home - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 5/1 | V Girls Outdoor Track | St. Paul Catholic, Seymour | Home - OHS Track [Directions] | 3:45 p.m. | ||
| Wed., 5/2 | V Boys Volleyball | Daniel Hand | Away - DHHS Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 5/2 | JV Boys Volleyball | Daniel Hand | Away - DHHS Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/2 | V Softball | Crosby | Away - Crosby HS Field #1 [Directions] | 4:00 p.m. | W 16-0 | |
| Thu., 5/3 | JV Softball | New Fairfield | Home - OHS Softball Field [Directions] | 4:30 p.m. | ||
| A request to make the following change(s) to the above event has been submitted by one of the schools involved, but has not yet been accepted by the other -- Change facility to | ||||||
| Fri., 5/4 | V Baseball | Watertown | Home - OHS Baseball Field [Directions] | 3:45 p.m. | L 10-0 (5) | |
| Fri., 5/4 | V Boys Volleyball | Joel Barlow | Home - OHS-Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 5/4 | JV Boys Volleyball | Joel Barlow | Home - OHS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/4 | V Softball | Watertown | Away - Watertown HS [Directions] | 3:45 p.m. | W 8-5 | |
| Sat., 5/5 | JV Baseball | Watertown | Home - OHS Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 5/5 | JV Softball | Watertown | Away - Watertown HS [Directions] | 10:00 a.m. | ||
| Mon., 5/7 | V Baseball | Derby | Away - Oxford HS [Directions] | 3:45 p.m. | W 17-7 (6) | |
| Mon., 5/7 | V Softball | Derby | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 11-4 | |
| Tue., 5/8 | V Boys Outdoor Track | Holy Cross, Woodland | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/8 | V Girls Outdoor Track | Holy Cross, Woodland | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/8 | JV Softball | Naugatuck | Home - OHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/9 | V Baseball | Ansonia | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 14-4 | |
| Wed., 5/9 | V Boys Volleyball | Xavier | Home - OHS-Main Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 5/9 | JV Boys Volleyball | Xavier | Home - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 5/9 | V Softball | Ansonia | Away - Ansonia HS [Directions] | 3:30 p.m. | W 25-0 | |
| Thu., 5/10 | V Boys Volleyball | Shelton | Home - OHS-Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Thu., 5/10 | JV Boys Volleyball | Shelton | Home - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 5/11 | V Baseball | Seymour | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 4-0 | |
| Fri., 5/11 | JV Baseball | Seymour | Away - French Park [Directions] | 3:45 p.m. | ||
| Fri., 5/11 | V Boys Outdoor Track | Irv Black Invitational | Away | 3:30 p.m. | ||
| Fri., 5/11 | V Boys Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | L 1-3 | |
| Fri., 5/11 | JV Boys Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | ||
| Fri., 5/11 | V Girls Outdoor Track | Irv Black Invitational | Away | 3:30 p.m. | ||
| Fri., 5/11 | V Softball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 0-13 | |
| Sat., 5/12 | V Boys Outdoor Track | Irv Black Invitational | Away | 10:00 a.m. | 1 Bus | |
| Sat., 5/12 | V Girls Outdoor Track | Irv Black Invitational | Away | 10:00 a.m. | ||
| Mon., 5/14 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | W 8-4 | |
| Mon., 5/14 | V Softball | St. Paul Catholic | Home - OHS Softball Field [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 5/14 | Unified Sports Volleyball | Nonnewaug | Away [Directions] | 3:30 p.m. | ||
| Tue., 5/15 | V Boys Volleyball | Kolbe Cathedral | Home - OHS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 5/15 | JV Boys Volleyball | Kolbe Cathedral | Home - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 5/17 | Unified Sports Volleyball | NVL Unified Volleyball Tournament | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Tue., 5/22 | V Boys Outdoor Track | NVL Championship | Away [Directions] | 1:30 p.m. | ||
| Tue., 5/22 | V Girls Outdoor Track | NVL Championship | Away [Directions] | 1:30 p.m. | ||
| Wed., 5/23 | V Baseball | Sacred Heart | Home - Wolcott HS [Directions] | 12:30 p.m. | W 5-3 | |
| Wed., 5/23 | V Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | 12:45 p.m. | W 7-1 | |
| Thu., 5/24 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 5/29 | V Boys Outdoor Track | CIAC Championship | Away | 3:00 p.m. | 1 Bus | |
| Tue., 5/29 | V Girls Outdoor Track | CIAC Championships | Away | 3:00 p.m. | ||
| Tue., 5/29 | Miscellaneous Events | Unified Picnic | 12:45 p.m. | |||
| Mon., 6/4 | V Boys Outdoor Track | CIAC Open Championship | Away | 1:30 p.m. | ||
| Mon., 6/4 | V Girls Outdoor Track | CIAC Open Championship | Away | 1:30 p.m. | ||