| Oxford 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 553 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Watertown | Home - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Torrington | Home - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | ||
| TBA | JV Baseball | Sacred Heart | Home - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | TBA | ||
| TBA | V Boys Basketball | Platt Tech (Scrim.) | Home - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| TBA | FM Football | Wilby (Scrim.) | Home - OHS Football Field - West [Directions] | TBA | ||
| TBA | FM Football | Holy Cross | Away - Holy Cross HS [Directions] | TBA | ||
| TBA | JV Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | ||
| TBA | JV Boys Soccer | Kennedy | Home - OHS Soccer Field-West [Directions] | TBA | ||
| TBA | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Boys Soccer | Wilby | Home - OHS Soccer Field-West [Directions] | TBA | ||
| TBA | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | Cancelled | Cancelled | |
| TBA | JV Girls Basketball | Ansonia | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| TBA | JV Girls Soccer | Sacred Heart | Away - Bucks Hill (Montoe) Park | TBA | ||
| TBA | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Girls Soccer | St. Paul Catholic | Home - OHS Soccer Field-West [Directions] | TBA | ||
| TBA | JV Girls Soccer | Bethel | Away - Bethel MS Field [Directions] | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Home - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Softball | Crosby | Home - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | TBA | ||
| TBA | JV Softball | Wolcott | Away - Wolcott HS [Directions] | TBA | ||
| TBA | JV Softball | Woodland | Home - OHS Softball Field [Directions] | TBA | ||
| Sat., 8/25 | V Football | Fairfield Warde/Nonnewaug | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sun., 8/26 | V Girls Soccer | Newtown Jamboree | Away | 3:45 p.m. | ||
| Thu., 8/30 | V Football | Amity (Scrim.) | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Thu., 8/30 | V Girls Volleyball | Bethel (Scrim.) | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | JV Girls Volleyball | Bethel (Scrim.) | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 8/31 | V Girls Soccer | Nonnewaug (Scrim.) | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Sat., 9/1 | V Girls Volleyball | Jamboree/Scrimmage | Away [Directions] | 9:30 a.m. | ||
| Fri., 9/7 | V Girls Soccer | Bunnell | Home - OHS Wolverine Field (Turf) [Directions] | 4:00 p.m. | W 5-4 | |
| Sat., 9/8 | V Football | Wilby | Away - Municipal Stadium [Directions] | 10:00 a.m. | W 42-0 | |
| Sat., 9/8 | V Boys Soccer | Derby | Home - OHS Wolverine Field (Turf) [Directions] | 11:30 a.m. | W 7-3 | |
| Sat., 9/8 | V Girls Soccer | Derby | Away - Derby -Witek Park [Directions] | 10:00 a.m. | W 6-1 | |
| Mon., 9/10 | JV Girls Soccer | Watertown | Away - Swift MS [Directions] | 3:30 p.m. | ||
| Mon., 9/10 | V Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Mon., 9/10 | JV Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Tue., 9/11 | V Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | L 1-4 | |
| Tue., 9/11 | V Girls Soccer | Wolcott | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 1-5 | |
| Tue., 9/11 | V Girls Volleyball | Ansonia | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 9/11 | JV Girls Volleyball | Ansonia | Home - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/12 | V Boys Cross Country | St. Paul Catholic, Seymour, Kennedy | Home - OHS Wolverine Field (Turf) [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | JV Boys Soccer | Wolcott | Away - Wolcott HS, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 9/12 | V Girls Cross Country | St. Paul Catholic, Seymour, Kennedy | Home - OHS Wolverine Field (Turf) [Directions] | 4:00 p.m. | St. Paul Catholic 15 Oxford 50 Seymour 15 Oxford 50 Kennedy 15 Oxford 50 | |
| Wed., 9/12 | JV Girls Soccer | Wolcott | Home - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Thu., 9/13 | V Boys Soccer | Watertown | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 5-1 | |
| Fri., 9/14 | V Football | Wolcott | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 20-38 | |
| Fri., 9/14 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | L 0-5 | |
| Fri., 9/14 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - OHS Pool [Directions] | 5:00 p.m. | ||
| Fri., 9/14 | V Girls Volleyball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 9/14 | JV Girls Volleyball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Sat., 9/15 | V Boys Cross Country | Wilton Invitational | Away [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | JV Boys Soccer | Watertown | Home - OHS Soccer Field-West [Directions] | 9:30 a.m. | ||
| Mon., 9/17 | V Boys Soccer | Bassick | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 6-1 | |
| Mon., 9/17 | V Girls Soccer | Torrington | Home - OHS Wolverine Field (Turf) [Directions] | 6:30 p.m. | W 6-1 | |
| Mon., 9/17 | V Girls Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 9/17 | JV Girls Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/18 | V Girls Swimming and Diving | Seymour | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/18 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/18 | JV Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 4:45 p.m. | ||
| Wed., 9/19 | V Boys Cross Country | Watertown, Derby | Home - OHS Wolverine Field (Turf) [Directions] | 3:30 p.m. | ||
| Wed., 9/19 | V Girls Cross Country | Watertown, Derby | Home - OHS Wolverine Field (Turf) [Directions] | 3:30 p.m. | Watertown 15 Oxford 50 Derby 15 Oxford 50 | |
| Wed., 9/19 | V Girls Soccer | Sacred Heart | Away - Municipal Stadium | 6:30 p.m. | W 8-0 | |
| Thu., 9/20 | V Football | Ansonia | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 9-45 | |
| Thu., 9/20 | V Boys Soccer | WCA | Away - Municipal Stadium [Directions] | 6:30 p.m. | W 2-0 | |
| Fri., 9/21 | FM Football | Ansonia | Home - OHS Wolverine Field (Turf) [Directions] | 3:15 p.m. | ||
| Fri., 9/21 | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | 3:45 p.m. | ||
| Fri., 9/21 | V Girls Swimming and Diving | Naugatuck | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Girls Volleyball | Wilby | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/21 | JV Girls Volleyball | Wilby | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | 6:30 p.m. | W 6-0 | |
| Tue., 9/25 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | 4:00 p.m. | ||
| Tue., 9/25 | V Girls Volleyball | Crosby | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/25 | JV Girls Volleyball | Crosby | Home - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/26 | V Girls Volleyball | Nonnewaug | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Wed., 9/26 | JV Girls Volleyball | Nonnewaug | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Boys Cross Country | Naugatuck, Wilby, Sacred Heart | Away - Breen S (middle school) [Directions] | 3:30 p.m. | ||
| Thu., 9/27 | V Girls Cross Country | Naugatuck, Wilby, Sacred Heart | Away - Breen S (middle school) [Directions] | 3:30 p.m. | ||
| Thu., 9/27 | V Girls Soccer | St. Paul Catholic | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 2-0 | |
| Fri., 9/28 | V Football | Derby | Away - Oxford HS - Turf Field [Directions] | 7:00 p.m. | W 41-40 (OT) | |
| Fri., 9/28 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | ||
| Fri., 9/28 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/28 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 4:45 p.m. | ||
| Sat., 9/29 | FM Football | Derby | Away - OHS Wolverine Field (Turf) [Directions] | 12:00 p.m. | ||
| Sat., 9/29 | V Boys Soccer | St. Paul Catholic | Home - Oxford H.S. [Directions] | 9:00 a.m. | L 5-1 | |
| Mon., 10/1 | V Boys Soccer | Kennedy | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 4-2 | |
| Tue., 10/2 | V Boys Cross Country | Holy Cross, Wolcott, WCA | Away - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | L 0-5 | |
| Tue., 10/2 | V Girls Cross Country | Holy Cross, Wolcott, WCA | Away - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Soccer | Naugatuck | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 0-2 | |
| Tue., 10/2 | V Girls Swimming and Diving | Woodland | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/2 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 4:30 p.m. | ||
| Tue., 10/2 | Unified Sports Soccer | Crosby and Wilby | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Wed., 10/3 | JV Boys Soccer | Naugatuck | Away - Breen SS (JV & Fr.) [Directions] | 3:45 p.m. | ||
| Wed., 10/3 | JV Girls Soccer | Naugatuck | Home - OHS Soccer Field-West [Directions] | Cancelled | Cancelled | |
| Wed., 10/3 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Wed., 10/3 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Girls Soccer | Holy Cross | Home - Oxford HS [Directions] | 6:00 p.m. | L 2-5 | |
| Thu., 10/4 | Unified Sports Soccer | Torrington Tournament | Away [Directions] | 3:00 p.m. | ||
| Fri., 10/5 | V Football | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 7-49 | |
| Fri., 10/5 | V Boys Soccer | Holy Cross | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 3-1 | |
| Fri., 10/5 | JV Girls Soccer | Naugatuck | Home - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Fri., 10/5 | V Girls Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | Seymour | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/5 | JV Girls Volleyball | Seymour | Home - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Sat., 10/6 | V Boys Cross Country | Wickham Invitational | Away | 11:20 a.m. | Wickham Park | |
| Sat., 10/6 | JV Boys Soccer | Holy Cross | Home - OHS Soccer Field-West [Directions] | 10:00 a.m. | ||
| Sat., 10/6 | JV Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 10:00 a.m. | ||
| Tue., 10/9 | V Boys Cross Country | Woodland, Torrington, Crosby | Away - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/9 | V Boys Soccer | Woodland | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 8-0 | |
| Tue., 10/9 | V Girls Cross Country | Woodland, Torrington, Crosby | Away - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/9 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 10/9 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | Unified Sports Soccer | Cheshire | Away - [Directions] | 3:00 p.m. | ||
| Wed., 10/10 | JV Boys Soccer | Woodland | Home - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Wed., 10/10 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | W 2-1 | |
| Wed., 10/10 | V Girls Swimming and Diving | New Fairfield | Away [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | FR Girls Volleyball | Sacred Heart | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/11 | V Girls Volleyball | Torrington | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Thu., 10/11 | JV Girls Volleyball | Torrington | Home - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Fri., 10/12 | FM Football | Nonnewaug | Away - Nonnewaug HS Field [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 4:00 p.m. | L 5-3 | |
| Fri., 10/12 | V Girls Soccer | Seymour | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | T 2-2 | |
| Fri., 10/12 | V Girls Swimming and Diving | Torrington | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 10/12 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 4:45 p.m. | ||
| Sat., 10/13 | JV Boys Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/15 | V Girls Volleyball | Bassick | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/15 | JV Girls Volleyball | Bassick | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Boys Soccer | Wilby | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | W 3-1 | |
| Tue., 10/16 | V Girls Swimming and Diving | Watertown | Home - OHS Pool [Directions] | 5:00 p.m. | ||
| Tue., 10/16 | V Girls Volleyball | Woodland | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/16 | JV Girls Volleyball | Woodland | Home - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Tue., 10/16 | Unified Sports Soccer | Torrington | Away [Directions] | 2:30 p.m. | ||
| Wed., 10/17 | V Boys Cross Country | NVL Championships | Away | 3:00 p.m. | ||
| Wed., 10/17 | V Girls Cross Country | NVL Championships | Away [Directions] | 3:00 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Crosby | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 2-3 | |
| Fri., 10/19 | V Football | Seymour | Away - Seymour HS Turf Field [Directions] | 6:30 p.m. | L 27-45 | |
| Fri., 10/19 | V Girls Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | W 3-2 | |
| Fri., 10/19 | V Girls Volleyball | WCA | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/19 | JV Girls Volleyball | WCA | Home - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Sat., 10/20 | FM Football | Seymour | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | JV Boys Soccer | Crosby | Home - OHS Soccer Field-West [Directions] | 11:00 a.m. | ||
| Sat., 10/20 | V Girls Soccer | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 2:00 p.m. | L 0-2 | |
| Sat., 10/20 | JV Girls Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 10/22 | V Boys Soccer | Torrington | Away - Torrington HS [Directions] | 6:30 p.m. | L 0-4 | |
| Mon., 10/22 | V Girls Soccer | Watertown | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | L 2-6 | |
| Mon., 10/22 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | W 3-2 | |
| Mon., 10/22 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | ||
| Mon., 10/22 | Unified Sports Soccer | Wolcott | Away [Directions] | 3:00 p.m. | ||
| Tue., 10/23 | JV Boys Soccer | Torrington | Away - Torrington HS [Directions] | 4:30 p.m. | ||
| Tue., 10/23 | JV Girls Soccer | Watertown | Home - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Wed., 10/24 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | T 2-2 | |
| Wed., 10/24 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 10/24 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 4:30 p.m. | ||
| Thu., 10/25 | V Girls Soccer | Ansonia | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 7-0 | |
| Thu., 10/25 | JV Girls Soccer | Ansonia | Home - OHS Soccer Field-West [Directions] | Cancelled | Cancelled | |
| Fri., 10/26 | V Boys Cross Country | CIAC Championships | Away [Directions] | 1:00 p.m. | Wickham Park | |
| Fri., 10/26 | V Football | WCA | Home - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 50-6 | |
| Fri., 10/26 | V Girls Cross Country | CIAC Championships | Away [Directions] | 1:00 p.m. | Wickham Park | |
| Fri., 10/26 | JV Girls Volleyball | Naugatuck JV Tournament | Away [Directions] | 3:00 pm | ||
| Sat., 10/27 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 1:30 p.m. | NVL Quarterfinal | |
| Sat., 10/27 | V Girls Volleyball | Seymour | Away [Directions] | TBA | ||
| Mon., 10/29 | V Girls Soccer | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | 5:15 p.m. | NVL Quarterfinal | |
| Mon., 10/29 | V Girls Volleyball | NVL Semi Final | Away | TBA | ||
| Tue., 10/30 | V Girls Swimming and Diving | NVL Trials | Away [Directions] | 4:30 p.m. | ||
| Thu., 11/1 | FM Football | Masuk | Away [Directions] | 3:45 p.m. | ||
| Thu., 11/1 | V Girls Soccer | Brookfield (Scrim.) | Away - BHS Back Turf [Directions] | 3:30 p.m. | CIAC 1st Round | |
| Thu., 11/1 | V Girls Swimming and Diving | NVL Diving Championships | Away [Directions] | 6:00 p.m. | ||
| Thu., 11/1 | V Girls Volleyball | Bethel (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Thu., 11/1 | V Girls Volleyball | NVL Championship | Away | TBA | ||
| Fri., 11/2 | V Football | Sacred Heart | Away - Municipal Stadium | 5:30 p.m. | W 49-22 | |
| Fri., 11/2 | V Girls Swimming and Diving | NVL Championships | Away [Directions] | 4:30 p.m. | ||
| Sat., 11/3 | FM Football | Sacred Heart | Home - OHS Wolverine Field (Turf) [Directions] | Cancelled | Cancelled | |
| Sat., 11/3 | FM Football | Holy Cross | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Mon., 11/5 | V Girls Soccer | Wilcox Tech | Away - Wilcox Tech School Field [Directions] | 2:00 p.m. | W 7-0 | |
| Mon., 11/5 | V Girls Volleyball | Cheney Tech | Away [Directions] | 5:30 p.m. | CIAC 1st Round | |
| Wed., 11/7 | V Girls Soccer | Plainfield | Away - Plainfield HS soccer field [Directions] | 2:00 p.m. | ||
| Wed., 11/7 | V Girls Volleyball | East Catholic | Away [Directions] | 6:00 p.m. | ||
| Fri., 11/9 | V Girls Volleyball | SMSA | Away - SMSA [Directions] | 6:00 p.m. | ||
| Sat., 11/10 | V Football | Woodland | Home - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | L 7-21 | |
| Sat., 11/10 | V Girls Swimming and Diving | Class S Qualifying Meet | Away [Directions] | 10:00 a.m. | ||
| Mon., 11/12 | FM Football | Woodland | Away - Woodland Football Field [Directions] | 3:45 p.m. | ||
| Wed., 11/14 | V Girls Swimming and Diving | Class S Championships | Away | 7:00 p.m. | at Wesleyan | |
| Fri., 11/16 | FM Football | St. Paul Catholic | Home - OHS Wolverine Field (Turf) [Directions] | Cancelled | Cancelled | |
| Wed., 11/21 | V Football | St. Paul Catholic | Home - OHS Wolverine Field (Turf) [Directions] | 5:00 p.m. | L 22-38 | |
| Fri., 11/30 | V Girls Basketball | Masuk (Scrim.) | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/1 | V Boys Ice Hockey | Westfield (MA) (Scrim.) | Away | 2:00 p.m. | ||
| Sun., 12/2 | V Boys Ice Hockey | Longmeadow (MA) (Scrim.) | Away | 4:30 p.m. | ||
| Wed., 12/5 | V Girls Basketball | Amity (Scrim.) | Away - Paul D. Mengold Gym at Amity HS [Directions] | 3:30 p.m. | ||
| Wed., 12/5 | V Girls Ice Hockey | Fairfield Ludlowe/Warde (Scrim.) | Away - Wonderland of Ice [Directions] | 3:15 p.m. | ||
| Fri., 12/7 | V Boys Basketball | Gilbert (Scrim.) | Home - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/7 | V Boys Ice Hockey | Jamboree | Home - Bennett Rink [Directions] | 6:00 p.m. | ||
| Fri., 12/7 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 8-2 | |
| Sat., 12/8 | V Boys Ice Hockey | Alumni Game | Home - Bennett Rink [Directions] | 7:00 p.m. | ||
| Tue., 12/11 | V Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 38-45 | |
| Wed., 12/12 | V Boys Ice Hockey | Guilford | Home - Bennett Rink [Directions] | 5:00 p.m. | L 7-8 | |
| Wed., 12/12 | V Wrestling | Derby/Oxford/Holy Cross | Home - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/12 | V Wrestling | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/12 | V Girls Ice Hockey | Branford | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 6-1 | |
| Thu., 12/13 | V Girls Basketball | Ansonia | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 43-29 | |
| Thu., 12/13 | Miscellaneous Events | Football Senior Center Trip | 12:00 p.m. | Pick up at 1:30 pm | ||
| Fri., 12/14 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 48-79 | |
| Fri., 12/14 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | V Boys Indoor Track | Hillhouse Invitational | Away - Hillhouse HS | 4:00 p.m. | ||
| Fri., 12/14 | V Girls Basketball | Naugatuck | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 36-51 | |
| Fri., 12/14 | V Girls Indoor Track | Hillhouse Invitational | Away - Hillhouse HS | 4:00 p.m. | ||
| Fri., 12/14 | Unified Sports Basketball | WCA | Away [Directions] | 2:45 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | W 5-3 | |
| Sat., 12/15 | V Wrestling | Oxford Invitational | Away - Oxford HS | 10:00 a.m. | ||
| Sat., 12/15 | V Wrestling | Oxford Invitational | Home [Directions] | 9:30 a.m. | ||
| Sat., 12/15 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | 1:00 p.m. | L 7-0 | |
| Mon., 12/17 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 55-58 | |
| Mon., 12/17 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Mon., 12/17 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 4:30 p.m. | W 5-2 | |
| Tue., 12/18 | V Boys Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 12/18 | V Girls Basketball | Shelton | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 26-50 | |
| Tue., 12/18 | JV Girls Basketball | Shelton | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Wed., 12/19 | V Boys Ice Hockey | Westhill/Stamford | Home - Bennett Rink [Directions] | 6:30 p.m. | W 5-2 | |
| Wed., 12/19 | V Wrestling | Thomaston | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/19 | V Wrestling | Northwestern | Home - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/19 | V Girls Ice Hockey | Hamden Coop | Home - The Rinks at Shelton [Directions] | 5:00 p.m. | L 8-0 | |
| Thu., 12/20 | V Boys Basketball | Kennedy | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 61-73 | |
| Thu., 12/20 | JV Boys Basketball | Kennedy | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/20 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - OHS Pool [Directions] | 4:30 p.m. | ||
| Thu., 12/20 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 6:00 p.m. | L 41-52 | |
| Fri., 12/21 | V Girls Ice Hockey | East Catholic Coop | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 8-0 | |
| Sat., 12/22 | V Wrestling | Brookfield/Shepaug, Bethel | Home - OHS-Main Gym [Directions] | 12:00 p.m. | ||
| Wed., 12/26 | V Boys Ice Hockey | Branford | Home - Bennett Rink [Directions] | 6:30 p.m. | L 2-0 | |
| Wed., 12/26 | V Wrestling | Terryville-Thomaston | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 12/27 | V Boys Basketball | Woodland | Away - Litchfield HS [Directions] | 6:00 p.m. | W 53-50 | Cowboy Classic |
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away | 12:00 p.m. | SCSU | |
| Thu., 12/27 | V Wrestling | Shelton, Fairfield Prep | Away - Shelton HS - Auxillary Gym [Directions] | 10:00 a.m. | ||
| Thu., 12/27 | V Girls Indoor Track | Jack Long Invitational | Away | 12:00 p.m. | SCSU | |
| Sat., 12/29 | V Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 7:30 p.m. | W 63-58 | Cowboy Classic |
| Sat., 12/29 | V Boys Indoor Track | 3rd Annual Wilton Wright Invitational | Away | 3:00 p.m. | ||
| Sat., 12/29 | V Wrestling | Holy Cross, Somers, Stratford | Home - Derby HS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/29 | V Wrestling | Milford Duals | Away [Directions] | TBA | ||
| Sat., 12/29 | V Girls Indoor Track | 3rd Annual Wilton Wright Invitational | Away | 3:00 p.m. | ||
| Wed., 1/2 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | L 74-81 | |
| Wed., 1/2 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:30 p.m. | ||
| Wed., 1/2 | V Boys Ice Hockey | Simsbury | Away - Westminster School [Directions] | 6:00 p.m. | W 3-2 (OT) | |
| Wed., 1/2 | V Girls Basketball | Wolcott | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 60-30 | |
| Wed., 1/2 | Unified Sports Basketball | Wolcott | Home - OHS-Main Gym [Directions] | 3:00 p.m. | ||
| Thu., 1/3 | V Boys Indoor Track | 5th Annual Wintergreen Invitational | Away | TBA | ||
| Thu., 1/3 | V Wrestling | Northwestern | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/3 | V Wrestling | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | ||
| Thu., 1/3 | V Girls Gymnastics | Fairfield Ludlowe, Darien | Away - GCA [Directions] | 6:30 p.m. | 112.35 | |
| Thu., 1/3 | V Girls Indoor Track | 5th Annual Wintergreen Invitational | Away | TBA | ||
| Fri., 1/4 | V Boys Basketball | Derby | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 41-71 | |
| Fri., 1/4 | JV Boys Basketball | Derby | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS [Directions] | 4:00 p.m. | ||
| Fri., 1/4 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 6:00 p.m. | W 60-30 | |
| Fri., 1/4 | V Girls Ice Hockey | Guilford Coop | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 5-0 | |
| Sat., 1/5 | V Boys Ice Hockey | Guilford | Away - East Haven Ice Rink [Directions] | 1:00 p.m. | L 5-4 | |
| Sat., 1/5 | V Boys Indoor Track | James Barber Invitational | Away | 12:00 p.m. | SCSU | |
| Sat., 1/5 | V Boys Indoor Track | 3rd Annual James Barber Invitational | Away | TBA | ||
| Sat., 1/5 | V Wrestling | Lawless Duals | Away [Directions] | 9:00 a.m. | ||
| Sat., 1/5 | V Wrestling | Lawless Tournament | Away - Nonnewaug HS | 9:30 a.m. | ||
| Sat., 1/5 | V Girls Gymnastics | Pomperaugh Invitational | Away [Directions] | TBA | 132.65 | |
| Sat., 1/5 | V Girls Indoor Track | James Barber Invitational | Away | 12:00 p.m. | SCSU | |
| Sat., 1/5 | V Girls Indoor Track | 3rd Annual James Barber Invitational | Away | TBA | ||
| Sun., 1/6 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - The Rinks at Shelton [Directions] | 4:30 p.m. | L 7-4 | |
| Tue., 1/8 | V Boys Swimming and Diving | Sacred Heart | Home - OHS Pool [Directions] | 7:00 p.m. | ||
| Tue., 1/8 | V Girls Basketball | Woodland | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 42-35 | |
| Tue., 1/8 | V Girls Gymnastics | New Milford, Joel Barlow, Newtown | Away - New Milford HS [Directions] | 5:00 p.m. | 118.65 | |
| Wed., 1/9 | V Boys Ice Hockey | Cheshire | Home - Bennett Rink [Directions] | 6:00 p.m. | W 2-1 (OT) | |
| Wed., 1/9 | V Wrestling | Thomaston | Home - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/10 | V Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 6:00 p.m. | L 46-54 | |
| Thu., 1/10 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | 4:00 p.m. | L 9-1 | |
| Fri., 1/11 | V Boys Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | L 43-83 | |
| Fri., 1/11 | JV Boys Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Fri., 1/11 | V Girls Basketball | Torrington | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 65-46 | |
| Fri., 1/11 | Unified Sports Basketball | Cheshire | Home - OHS-Main Gym [Directions] | 2:30 p.m. | ||
| Sat., 1/12 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 1:00 p.m. | W 7-3 | |
| Sat., 1/12 | V Wrestling | Canton, Northwestern, Farmington, Haddam-Killingworth | Away - Canton H.S. [Directions] | 10:00 a.m. | ||
| Sat., 1/12 | V Wrestling | Darien, Weston, Bunnell | Away - DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/12 | Winter Dance Team | Dancin' in the Woods | Away [Directions] | 4:00 p.m. | ||
| Sat., 1/12 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - The Rinks at Shelton - Upper [Directions] | 8:50 p.m. | L 6-1 | |
| Mon., 1/14 | V Boys Basketball | WCA | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 52-73 | |
| Mon., 1/14 | JV Boys Basketball | WCA | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 1/14 | V Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 6:00 p.m. | W 50-20 | |
| Tue., 1/15 | V Boys Swimming and Diving | Holy Cross | Home - OHS Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/15 | V Wrestling | Terryville-Thomaston | Home - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/15 | V Girls Gymnastics | Pomperaug, Nonnewaug, Newtown | Away - Auxiliary Gym [Directions] | 5:00 p.m. | 122.15 | |
| Wed., 1/16 | V Boys Basketball | Seymour | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 43-73 | |
| Wed., 1/16 | JV Boys Basketball | Seymour | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/16 | V Boys Ice Hockey | Fairfield Prep | Home - Bennett Rink [Directions] | 6:00 p.m. | L 4-1 | |
| Wed., 1/16 | V Wrestling | Gilbert/Torrington | Away - Gilbert [Directions] | 6:00 p.m. | ||
| Wed., 1/16 | V Girls Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 31-46 | |
| Wed., 1/16 | JV Girls Basketball | Seymour | Away - Seymour HS [Directions] | Cancelled | Cancelled | |
| Wed., 1/16 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 11-6 | |
| Thu., 1/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden Ice Rink [Directions] | 4:30 p.m. | L 6-0 | Pick up @ Shelton |
| Fri., 1/18 | V Boys Basketball | Wilby | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 70-43 | |
| Fri., 1/18 | JV Boys Basketball | Wilby | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/18 | V Boys Indoor Track | HK Invitational | Away - Hillhouse HS | 5:00 p.m. | ||
| Fri., 1/18 | V Boys Swimming and Diving | Naugatuck | Home - OHS Pool [Directions] | 4:30 p.m. | ||
| Fri., 1/18 | V Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 62-32 | |
| Fri., 1/18 | V Girls Indoor Track | HK Invitational | Away - Hillhouse HS | 5:00 p.m. | ||
| Sat., 1/19 | V Wrestling | Eagle Classic | Away - East Catholic HS | 10:00 a.m. | ||
| Sat., 1/19 | V Competitive Cheerleading | Seymour Invitational | Away [Directions] | TBA | ||
| Sat., 1/19 | V Girls Gymnastics | Joel Barlow, New Milford, Newtown | Away - Gymnastics & Cheerleading Academy - Fairfield [Directions] | Cancelled | Cancelled | |
| Tue., 1/22 | Unified Sports Basketball | Nonnewaug | Away [Directions] | 2:30 p.m. | ||
| Wed., 1/23 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 39-56 | |
| Wed., 1/23 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Wed., 1/23 | V Boys Ice Hockey | Hamden | Home - Bennett Rink [Directions] | 6:30 p.m. | L 2-10 | |
| Wed., 1/23 | V Wrestling | Nonnewaug, St. Joseph | Away - Nonnewaug HS Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/23 | V Girls Basketball | St. Paul Catholic | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 39-58 | |
| Wed., 1/23 | V Girls Gymnastics | Daniel Hand, Newtown, Hamden | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 6:00 p.m. | 128.5 | |
| Thu., 1/24 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | 8:00 p.m. | L 8-0 | Pick up @ Shelton |
| Fri., 1/25 | V Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | L 66-68 | |
| Fri., 1/25 | JV Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:30 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Derby | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 49-26 | |
| Fri., 1/25 | V Girls Gymnastics | Wilton | Away [Directions] | 5:00 p.m. | 129.9 | |
| Fri., 1/25 | V Girls Ice Hockey | West Haven/SHA | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 6-1 | |
| Sat., 1/26 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton - Lower [Directions] | 8:30 p.m. | L 1-2 | |
| Sat., 1/26 | V Wrestling | Doc Meyers Invitational | Away [Directions] | 9:00 a.m. | ||
| Sat., 1/26 | V Wrestling | Doc Meyers Tournament | Away - Rocky Hill HS | 9:30 a.m. | ||
| Sat., 1/26 | V Competitive Cheerleading | Quinnipiac Invitational | Away | TBA | Quinnipiac University | |
| Sat., 1/26 | Winter Dance Team | QU Dance Challenge | Away | 6:00 p.m. | Quinnipiac University | |
| Sat., 1/26 | V Girls Gymnastics | Joel Barlow, New Milford, Newtown | Away [Directions] | 5:00 p.m. | 117.250 | |
| Mon., 1/28 | V Boys Ice Hockey | East Catholic | Home - Bennett Rink [Directions] | 5:45 p.m. | W 3-1 | |
| Mon., 1/28 | V Boys Indoor Track | NVL Championships | Away | 4:30 p.m. | ||
| Mon., 1/28 | V Boys Indoor Track | NVL Championship | Away | TBA | Hillhouse | |
| Mon., 1/28 | V Girls Indoor Track | NVL Championships | Away - Hillhouse HS | 4:30 p.m. | ||
| Mon., 1/28 | V Girls Indoor Track | NVL Championships | Away | TBA | Hillhouse | |
| Tue., 1/29 | Unified Sports Basketball | Masuk | Home - OHS-Main Gym [Directions] | 2:30 p.m. | ||
| Thu., 1/31 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 1/31 | V Wrestling | Gilbert/Torrington | Away - Gilbert [Directions] | 6:00 p.m. | ||
| Fri., 2/1 | V Boys Basketball | Ansonia | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 67-69(OT) | |
| Fri., 2/1 | JV Boys Basketball | Ansonia | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | Torrington | Home - OHS Pool [Directions] | 5:00 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 49-54 | |
| Fri., 2/1 | V Girls Gymnastics | Joel Barlow, Foran | Away - Gymnastics & Cheerleading Academy - Fairfield [Directions] | 6:30 p.m. | 135.30 | |
| Fri., 2/1 | V Girls Ice Hockey | Daniel Hand Coop | Home - The Rinks at Shelton [Directions] | 5:00 p.m. | L 8-0 | |
| Sat., 2/2 | V Wrestling | Four Corners Duals | Away - Canton H.S. | 10:00 a.m. | ||
| Sat., 2/2 | V Wrestling | Foran Duals | Away [Directions] | 9:00 a.m. | ||
| Sat., 2/2 | V Competitive Cheerleading | Torrington Invitational | Away [Directions] | TBA | ||
| Sat., 2/2 | V Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 3:00 p.m. | W 42-39 | |
| Sat., 2/2 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena [Directions] | 8:50 p.m. | L 6-1 | Pick up @ Masuk |
| Mon., 2/4 | V Boys Basketball | Woodland | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 64-72 | |
| Mon., 2/4 | JV Boys Basketball | Woodland | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 2/4 | V Boys Indoor Track | Last Chance Relays | Away - Hillhouse HS | 5:00 p.m. | ||
| Mon., 2/4 | V Girls Indoor Track | Last Chance Relays | Away - Hillhouse HS | 5:00 p.m. | ||
| Tue., 2/5 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 41-58 | |
| Tue., 2/5 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Seymour | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 37-56 | |
| Tue., 2/5 | JV Girls Basketball | Seymour | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Tue., 2/5 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | 7:30 p.m. | L 6-3 | Pick up @ Shelton |
| Tue., 2/5 | Unified Sports Basketball | WCA | Home - OHS-Main Gym [Directions] | 2:45 p.m. | ||
| Wed., 2/6 | V Boys Ice Hockey | North Haven | Home - Bennett Rink [Directions] | 6:00 p.m. | W 7-2 | |
| Wed., 2/6 | V Wrestling | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/6 | V Wrestling | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | ||
| Wed., 2/6 | Winter Dance Team | NVL Championship | Away [Directions] | 6:00 p.m. | ||
| Wed., 2/6 | Unified Sports Basketball | Wolcott | Away [Directions] | 3:00 p.m. | ||
| Thu., 2/7 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/7 | V Boys Indoor Track | State Championship | Away | TBA | ||
| Thu., 2/7 | V Girls Gymnastics | SWC Championship | Away [Directions] | 5:00 p.m. | 130.8 | |
| Thu., 2/7 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/7 | V Girls Indoor Track | State Championship | Away | TBA | ||
| Fri., 2/8 | V Boys Basketball | Watertown | Home - OHS-Main Gym [Directions] | 6:00 p.m. | W 80-78(OT) | |
| Fri., 2/8 | JV Boys Basketball | Watertown | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 6:00 p.m. | W 41-40 | |
| Fri., 2/8 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton [Directions] | 5:00 p.m. | L 0-6 | |
| Sat., 2/9 | V Boys Ice Hockey | Immaculate | Home - Bennett Rink [Directions] | 1:00 p.m. | W 5-4 (OT) | |
| Sat., 2/9 | V Wrestling | NVL/Berkshire Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 2/9 | V Wrestling | BNVL League Tournament | Home - OHS-Main Gym [Directions] | TBA | ||
| Sat., 2/9 | V Competitive Cheerleading | Watertown Invitational | Away [Directions] | TBA | ||
| Sat., 2/9 | Winter Dance Team | Warde Dance Dance | Away [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | V Girls Basketball | Holy Cross | Home - OHS-Main Gym [Directions] | 6:00 p.m. | L 40-50 | |
| Mon., 2/11 | Unified Sports Basketball | Newtown Tournament | Away | 3:00 p.m. | Newtown Youth Academy | |
| Wed., 2/13 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Bennett Rink [Directions] | 6:00 p.m. | L 4-0 | |
| Thu., 2/14 | V Girls Gymnastics | Jonathan Law, Hamden | Away - Jonathan Law HS Old Gym [Directions] | 6:00 p.m. | 124.65 | |
| Thu., 2/14 | V Girls Gymnastics | Jonathan Law, Hamden | Away [Directions] | Cancelled | Cancelled | |
| Thu., 2/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 5:30 p.m. | L 1-7 | |
| Fri., 2/15 | V Boys Swimming and Diving | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | ||
| Fri., 2/15 | V Wrestling | Class S Championship | Away - TBA | 5:30 p.m. | ||
| Fri., 2/15 | V Girls Ice Hockey | Simsbury | Home - The Rinks at Shelton [Directions] | 5:30 p.m. | L 0-4 | |
| Sat., 2/16 | V Boys Ice Hockey | Glastonbury | Home - Bennett Rink [Directions] | 1:00 p.m. | L 1-5 | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | Class S Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 2/16 | V Competitive Cheerleading | NVL Championships | Away [Directions] | TBA | ||
| Sat., 2/16 | V Girls Basketball | St. Paul Catholic | Away [Directions] | 12:45 p.m. | L 29-50 | |
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sun., 2/17 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | 1:15 p.m. | L 0-8 | Pick up @ Shelton |
| Mon., 2/18 | V Girls Gymnastics | Newtown, Nonnewaug, Pomperaug | Away - Kinetic Kids [Directions] | 1:00 p.m. | 134.2 | |
| Tue., 2/19 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | W 69-66 | |
| Tue., 2/19 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Wed., 2/20 | JV Boys Basketball | Crosby | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Thu., 2/21 | V Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 6:00 p.m. | W 80-46 | |
| Thu., 2/21 | JV Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 2/21 | V Boys Swimming and Diving | Kennedy | Home - OHS Pool [Directions] | 4:00 p.m. | ||
| Thu., 2/21 | Unified Sports Basketball | Pomperaug | Away [Directions] | 2:45 p.m. | ||
| Fri., 2/22 | V Boys Basketball | Crosby | Home - OHS-Main Gym [Directions] | 4:15 p.m. | L 59-99 | |
| Fri., 2/22 | V Wrestling | State Open Championship | Away - TBA | 5:00 p.m. | ||
| Sat., 2/23 | V Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | 10:00 a.m. | L 3-4(OT) | |
| Sat., 2/23 | V Wrestling | State Open Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 2/23 | Winter Dance Team | State Championships | Away [Directions] | 11:00 a.m. | ||
| Mon., 2/25 | V Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 4-6 | |
| Tue., 2/26 | V Boys Swimming and Diving | NVL Trials | Away [Directions] | 4:30 p.m. | ||
| Tue., 2/26 | V Girls Basketball | Sacred Heart | Away | 7:00 p.m. | CIAC First Round | |
| Tue., 2/26 | Unified Sports Basketball | Ansonia | Away [Directions] | 2:30 p.m. | ||
| Wed., 2/27 | V Boys Swimming and Diving | NVL Diving Championship | Away [Directions] | 6:00 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | NVL Championships | Away [Directions] | 4:30 p.m. | ||
| Fri., 3/1 | V Wrestling | New England Championship | Away - TBA | 5:00 a.m. | ||
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/2 | V Wrestling | State Open Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 3/2 | V Competitive Cheerleading | State Championships | Away | TBA | Hillhouse Field House | |
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Thu., 3/7 | Unified Sports Basketball | NVL Unified Basketball Tournament | Away [Directions] | 3:00 p.m. | ||
| Sat., 3/9 | V Competitive Cheerleading | Quest for the Best | Away [Directions] | TBA | ||
| Sat., 3/16 | V Competitive Cheerleading | New England Regionals | Away | TBA | Worchester State University, MA | |
| Tue., 3/19 | V Softball | Trumbull (Scrim.) | Away - Insports [Directions] | 4:00 p.m. | ||
| Wed., 3/20 | V Baseball | Masuk (Scrim.) | Home - Oxford HS [Directions] | 3:30 p.m. | ||
| Sun., 3/24 | V Baseball | Staples (Scrim.) | Away - Staples Baseball Field [Directions] | 12:30 p.m. | ||
| Mon., 3/25 | V Baseball | Branford (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Mon., 3/25 | V Softball | Bethel (Scrim.) | Away - Kisling field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Softball | Immaculate (Scrim.) | Away - Immaculate HS [Directions] | 4:00 p.m. | ||
| Fri., 3/29 | V Softball | Pomperaug (Scrim.) | Away - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 3/30 | V Baseball | Pomperaug | Home - OHS Baseball Field [Directions] | 12:00 p.m. | W 5-2 | |
| Sat., 3/30 | JV Baseball | Pomperaug | Home - OHS Baseball Field [Directions] | 2:30 p.m. | ||
| Sat., 3/30 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 11:00 a.m. | L 4-6 | |
| Mon., 4/1 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 4/1 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Baseball | Holy Cross | Away - Waterville Park [Directions] | 3:45 p.m. | L 11-1 | |
| Tue., 4/2 | V Boys Outdoor Track | Crosby, Woodland | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Girls Outdoor Track | Crosby, Woodland | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Softball | Holy Cross | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 5-3 | |
| Wed., 4/3 | JV Baseball | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | ||
| Wed., 4/3 | V Boys Volleyball | Masuk | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Wed., 4/3 | JV Boys Volleyball | Masuk | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | JV Softball | Holy Cross | Home - OHS Softball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/4 | V Baseball | Joel Barlow | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 5-3 | |
| Thu., 4/4 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 4:00 p.m. | W 14-1 | |
| Sat., 4/6 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 4/6 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 10:30 a.m. | ||
| Sat., 4/6 | JV Softball | Watertown | Away - Veterans Park [Directions] | 10:00 a.m. | ||
| Mon., 4/8 | V Boys Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 4/8 | JV Boys Volleyball | Newtown | Away [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | V Softball | Torrington | Home - OHS Softball Field [Directions] | 4:00 p.m. | W 18-10 | |
| Tue., 4/9 | V Boys Outdoor Track | Watertown, Wolcott | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | Oxford 90 Wolcott 40 Oxford 43 Watertown 80 Watertown 114 Wolcott 16 | |
| Tue., 4/9 | V Girls Outdoor Track | Watertown, Wolcott | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | Oxford 94 Wolcott 32 Oxford 61 Watertown 84 Wolcott 23 Watertown 119 | |
| Tue., 4/9 | V Softball | Watertown | Away - Watertown HS [Directions] | 3:45 p.m. | W 9-1 | |
| Wed., 4/10 | V Baseball | WCA | Away - Washington Park [Directions] | 3:45 p.m. | W 2-1 | |
| Wed., 4/10 | V Boys Volleyball | Southington | Away - West Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 4/10 | JV Boys Volleyball | Southington | Away - West Gym [Directions] | 5:00 p.m. | ||
| Wed., 4/10 | V Softball | WCA | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 19-1 | |
| Thu., 4/11 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | 3:45 p.m. | W 4-1 | |
| Thu., 4/11 | JV Baseball | WCA | Away - Washington Park [Directions] | 3:45 p.m. | ||
| Thu., 4/11 | V Boys Volleyball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 4/11 | JV Boys Volleyball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | JV Softball | WCA | Home - OHS Softball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/12 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 7-1 | |
| Fri., 4/12 | V Boys Outdoor Track | Holy Cross, Seymour | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2 Buses | |
| Fri., 4/12 | V Girls Outdoor Track | Holy Cross, Seymour | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 4/12 | V Softball | St. Paul Catholic | Home - OHS Softball Field [Directions] | 4:00 p.m. | L 2-6 | |
| Mon., 4/15 | V Boys Volleyball | Joel Barlow | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Mon., 4/15 | JV Boys Volleyball | Joel Barlow | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Baseball | Ansonia | Home - OHS Baseball Field [Directions] | 3:15 p.m. | L 5-3 (8) | |
| Tue., 4/16 | JV Baseball | Ansonia | Home - OHS Baseball Field [Directions] | Cancelled | Cancelled | |
| Tue., 4/16 | JV Softball | Ansonia | Away [Directions] | Cancelled | Cancelled | |
| Wed., 4/17 | V Baseball | Woodland | Home - OHS Baseball Field [Directions] | 3:45 p.m. | L 11-1 | |
| Wed., 4/17 | V Softball | Ansonia | Away - Ansonia HS [Directions] | 11:00 a.m. | W 20-0 | |
| Thu., 4/18 | V Baseball | Seymour | Home - OHS Baseball Field [Directions] | 11:00 a.m. | W 12-2 | |
| Thu., 4/18 | JV Baseball | Woodland | Home - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/18 | V Boys Volleyball | Staples | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 4/18 | JV Boys Volleyball | Staples | Home - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 4/19 | JV Baseball | Seymour | Home - OHS Baseball Field [Directions] | 11:00 a.m. | ||
| Fri., 4/19 | JV Softball | Seymour | Away - Seymour HS [Directions] | 10:00 a.m. | ||
| Tue., 4/23 | V Baseball | Kennedy | Away - Waterville Park [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/23 | V Boys Outdoor Track | Derby, Kennedy | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Derby, Kennedy | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Baseball | Derby | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 17-5 | |
| Wed., 4/24 | V Softball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:45 p.m. | W 25-2 | |
| Thu., 4/25 | JV Baseball | Derby | Home - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/25 | V Boys Volleyball | Shelton | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 4/25 | JV Boys Volleyball | Shelton | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Softball | Crosby | Home - OHS Softball Field [Directions] | 4:00 p.m. | W 21-1 | |
| Sat., 4/27 | V Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | 10:00 a.m. | W 18-2 | |
| Mon., 4/29 | V Baseball | Watertown | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 4/29 | V Boys Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Mon., 4/29 | JV Boys Volleyball | Lewis Mills | Home - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Mon., 4/29 | JV Boys Volleyball | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Naugatuck, WCA | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Naugatuck, WCA | Home - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Softball | Woodland | Home - Oxford [Directions] | 3:45 p.m. | W 19-4 | |
| Wed., 5/1 | V Baseball | Naugatuck | Home - OHS Baseball Field [Directions] | 3:45 p.m. | L 2-0(8) | |
| Wed., 5/1 | V Boys Volleyball | Daniel Hand | Away - DHHS Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 5/1 | JV Boys Volleyball | Daniel Hand | Away - DHHS Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | W 7-0 | |
| Wed., 5/1 | JV Softball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | JV Baseball | Naugatuck | Home - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | V Softball | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | W 8-0 | |
| Fri., 5/3 | V Softball | Ansonia | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 17-0 | |
| Sat., 5/4 | V Baseball | Sacred Heart | Home - OHS Baseball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Sat., 5/4 | JV Baseball | Ansonia | Away [Directions] | Cancelled | Cancelled | |
| Sat., 5/4 | JV Softball | Ansonia | Home - OHS Softball Field [Directions] | Cancelled | Cancelled | |
| Mon., 5/6 | V Baseball | Seymour | Away - French Park [Directions] | 3:30 p.m. | W 11-9 | |
| Mon., 5/6 | V Boys Volleyball | Xavier | Away - Xavier H.S. [Directions] | 5:00 p.m. | W 3-1 | |
| Mon., 5/6 | JV Boys Volleyball | Xavier | Away - Xavier H.S. [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Seymour | Home - OHS Softball Field [Directions] | 3:45 p.m. | L 7-8 | |
| Tue., 5/7 | JV Baseball | Seymour | Away - French Park [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Torrington, Sacred Heart | Away - Torrington HS [Directions] | 3:45 p.m. | 2 Buses | |
| Tue., 5/7 | V Girls Outdoor Track | Torrington, Sacred Heart | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | JV Softball | Seymour | Home - OHS Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Baseball | Wolcott | Home - OHS Baseball Field [Directions] | 4:00 p.m. | L 7-0 | |
| Wed., 5/8 | V Boys Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | W 3-0 | |
| Wed., 5/8 | JV Boys Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Wolcott | Away - George Babcock Field, Wolcott HS [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 5/9 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 2:30 p.m. | W 9-0 | |
| Thu., 5/9 | JV Baseball | Wolcott | Home - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/9 | V Boys Volleyball | Kolbe Cathedral | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Thu., 5/9 | JV Boys Volleyball | Kolbe Cathedral | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:45 p.m. | L 12-1 | |
| Fri., 5/10 | V Softball | Woodland | Away - Woodland Softball Field [Directions] | 3:45 p.m. | W 9-0 | |
| Sat., 5/11 | JV Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 1:00 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Newtown | Home - OHS-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Mon., 5/13 | JV Boys Volleyball | Newtown | Home - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Softball | Wilby | Away - Municipal Stadium [Directions] | 6:00 p.m. | W 20-2 | |
| Wed., 5/15 | V Baseball | Wilby | Home - OHS Baseball Field [Directions] | 3:45 p.m. | W 10-0 | |
| Wed., 5/15 | V Boys Volleyball | Cheshire | Away - Cheshire High - West Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 5/15 | JV Boys Volleyball | Cheshire | Away - Cheshire High - West Gym [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | V Softball | Derby | Home - OHS Softball Field [Directions] | 3:45 p.m. | W 14-3 | |
| Fri., 5/17 | V Boys Volleyball | Lewis Mills | Home - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Fri., 5/17 | JV Boys Volleyball | Lewis Mills | Away [Directions] | Cancelled | Cancelled | |
| Fri., 5/17 | JV Boys Volleyball | Lewis Mills | Home [Directions] | 4:00 p.m. | ||
| Sat., 5/18 | V Baseball | Derby | Away - OHS Baseball Field [Directions] | 4:00 p.m. | W 13-1 | |
| Mon., 5/20 | V Boys Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 5/20 | JV Boys Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 5:30 p.m. | ||
| Tue., 5/21 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 4:00 p.m. | NVL Quarterfinals | |
| Tue., 5/21 | V Boys Outdoor Track | NVL Championship | Away [Directions] | 1:30 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | NVL Championship | Away [Directions] | 1:30 p.m. | ||
| Tue., 5/21 | V Softball | Wolcott | Home - OHS Softball Field [Directions] | 4:00 p.m. | W 12-4 | |
| Wed., 5/22 | V Baseball | NVL Semifinals | Away | Cancelled | Cancelled | Municipal Stadium |
| Wed., 5/22 | V Boys Volleyball | Joel Barlow | Away [Directions] | 6:00 p.m. | SWC Championship Play In Game | |
| Wed., 5/22 | V Softball | Watertown | Away [Directions] | 4:00 p.m. | W 6-0 | NVL Semifinals @ Seymour |
| Thu., 5/23 | V Baseball | NVL Finals | Away | Cancelled | Cancelled | Municipal Stadium |
| Thu., 5/23 | V Softball | Seymour | Away [Directions] | 5:00 p.m. | W 11-6 | NVL Finals |
| Fri., 5/24 | V Boys Volleyball | SWC Championship | Home - OHS-Main Gym [Directions] | 6:00 p.m. | Played at #1 Seed | |
| Fri., 5/24 | JV Boys Volleyball | SWC Championship | Home - OHS-Main Gym [Directions] | 4:00 p.m. | Played at #1 Seed | |
| Tue., 5/28 | V Girls Outdoor Track | State Championship | Away | 3:00 p.m. | ||
| Tue., 5/28 | Miscellaneous Events | NVL Unified Sports Picnic | Away | 10:00 a.m. | Wolcott | |
| Wed., 5/29 | V Baseball | Wamogo | Home - OHS Baseball Field [Directions] | 2:30 p.m. | State Playoffs 1st Round | |
| Wed., 5/29 | V Boys Volleyball | Masuk | Home - OHS-Main Gym [Directions] | 6:00 p.m. | Class M 1st Round | |
| Wed., 5/29 | V Softball | Nonnewaug | Home - OHS Softball Field [Directions] | 3:30 p.m. | CIAC Class M 1st Round | |
| Thu., 5/30 | V Baseball | St. Paul Catholic | Away - Muzzy Field, Bristol [Directions] | 3:30 p.m. | State Playoffs 2nd Round | |
| Thu., 5/30 | V Boys Outdoor Track | State Championship Meet | Away | 3:00 p.m. | ||
| Thu., 5/30 | V Softball | Lauralton Hall | Home - OHS Softball Field [Directions] | 3:30 p.m. | CIAC Class M 2nd Round | |