| Woodland 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 496 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Tue., 9/3 | V Boys Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy | 4:30 p.m. | ||
| Thu., 9/5 | V Football | Plainville | Away - Plainville HS-Plainville HS- Tinty Field and Track [Directions] | 6:00 p.m. | ||
| Thu., 9/5 | V Girls Soccer | Lyman Hall (Scrim.) | Home - Woodland HS-Woodland Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/5 | V Girls Volleyball | Brookfield (Scrim.) | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/5 | JV Girls Volleyball | Brookfield (Scrim.) | Home - Woodland HS-Gym [Directions] | 5:35 p.m. | ||
| Mon., 9/9 | V Girls Volleyball | Shelton (Scrim.) | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 9/9 | JV Girls Volleyball | Shelton (Scrim.) | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Holy Cross, St. Paul Catholic, Watertown | Home - Woodland HS-Track [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | Holy Cross, St. Paul Catholic, Watertown | Home - Woodland HS-Track [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Soccer | Pomperaug | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Volleyball | Amity (Scrim.) | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 9/10 | JV Girls Volleyball | Amity (Scrim.) | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 9/12 | V Boys Soccer | Sacred Heart | Away - Waterville Park-Soccer Pitch (Behind Building) | 3:45 p.m. | W 3-0 | |
| Thu., 9/12 | V Girls Soccer | Sacred Heart | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 9-0 | |
| Fri., 9/13 | V Football | Torrington | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | W 18-8 | |
| Fri., 9/13 | JV Boys Soccer | Sacred Heart | Away - Waterville Park-Soccer Pitch (Behind Building) | 3:45 p.m. | W 7-0 | |
| Fri., 9/13 | JV Girls Soccer | Sacred Heart | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 9/13 | V Girls Swimming and Diving | Waterford | Away - Waterford HS - official -Pool - WHS [Directions] | 4:30 p.m. | Win 105-77 | |
| Fri., 9/13 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/13 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/14 | FM Football | Torrington | Away - Torrington HS [Directions] | 10:30 a.m. | ||
| Sat., 9/14 | V Boys Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 10:00 a.m. | L 1-0 | |
| Sat., 9/14 | V Girls Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 1:00 p.m. | L 0-4 | |
| Sat., 9/14 | V Girls Volleyball | Amity, Avon, Darien, East Haven, Fairfield Ludlowe, Glastonbury, Joel Barlow, New Britain, New Canaan, North Haven, Seymour, Simsbury, SMSA, St. Joseph, St. Paul Catholic, Suffield, Trinity Catholic, Trumbull | Away - Connecticut Sports Center | 8:30 a.m. | ||
| Tue., 9/17 | V Boys Cross Country | Sacred Heart, Derby, Kennedy | Away - Bucks Hill (MONTOE) Park-XC Course | 3:45 p.m. | ||
| Tue., 9/17 | V Boys Soccer | WCA | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 5-2 | |
| Tue., 9/17 | V Boys Swimming and Diving | Naugatuck (Scrim.) | Home - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Sacred Heart, Derby, Kennedy | Away - Bucks Hill (MONTOE) Park-XC Course | 3:45 p.m. | ||
| Tue., 9/17 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/17 | V Girls Volleyball | Sacred Heart | Away - Sacred Heart HS-Alumni Hall | 6:00 p.m. | W 3-0 | |
| Tue., 9/17 | JV Girls Volleyball | Sacred Heart | Away - Sacred Heart HS-Alumni Hall | 4:45 p.m. | W 2-0 | |
| Wed., 9/18 | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-Upper Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Football | Wilby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 6:00 p.m. | W 54-12 | |
| Thu., 9/19 | V Boys Soccer | Portland | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 2-0 | |
| Thu., 9/19 | JV Boys Soccer | WCA | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | W 5-1 | |
| Thu., 9/19 | V Girls Soccer | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 4:00 p.m. | L 2-1 | |
| Thu., 9/19 | V Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/19 | JV Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 9/20 | FM Football | Wilby | Home - Woodland HS-Woodland Football Field [Directions] | 3:30 p.m. | ||
| Fri., 9/20 | V Boys Soccer | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | W 3-0 | |
| Fri., 9/20 | V Boys Swimming and Diving | Watertown (Scrim.) | Home - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Kennedy | Away - J F Kennedy HS Turf-Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 9/20 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 9/21 | JV Boys Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:00 a.m. | W 7-0 | |
| Sat., 9/21 | JV Boys Soccer | Crosby | Away - Crosby HS-CHS - Grass Soccer Field [Directions] | Canceled | Cancelled | |
| Mon., 9/23 | V Girls Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 8-0 | |
| Tue., 9/24 | V Boys Cross Country | Torrington, Crosby, Oxford | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Boys Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 8-0 | |
| Tue., 9/24 | V Boys Swimming and Diving | St. Paul Catholic (Scrim.) | Home - Woodland HS-pool [Directions] | 4:30 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Torrington, Crosby, Oxford | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Girls Volleyball | Watertown | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/24 | JV Girls Volleyball | Watertown | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 9/25 | V Girls Soccer | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | T 2-2 | |
| Thu., 9/26 | V Boys Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | 4:00 p.m. | L 3-1 | |
| Thu., 9/26 | JV Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | Postponed | ||
| Fri., 9/27 | V Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 7:00 p.m. | W 45-19 | |
| Fri., 9/27 | V Boys Swimming and Diving | Seymour (Scrim.) | Home - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | T 4-4 | |
| Fri., 9/27 | V Girls Volleyball | Crosby | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/27 | JV Girls Volleyball | Crosby | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 9/28 | FM Football | Derby | Home - Woodland HS-Woodland Football Field [Directions] | Canceled | Cancelled | |
| Sat., 9/28 | JV Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 9:30 a.m. | ||
| Tue., 10/1 | V Boys Cross Country | Wilby, Wolcott | Home - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Tue., 10/1 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/1 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-Upper Soccer Field [Directions] | 3:45 p.m. | W 6-1 | |
| Tue., 10/1 | V Boys Swimming and Diving | Naugatuck (Scrim.) | Home - Woodland HS-pool [Directions] | Canceled | Cancelled | |
| Tue., 10/1 | V Girls Cross Country | Wilby, Wolcott | Home - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Girls Soccer | St. Paul Catholic | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 2-0 | |
| Tue., 10/1 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/1 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | L 1-2 | |
| Wed., 10/2 | JV Girls Soccer | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 10/3 | V Girls Volleyball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 10/3 | JV Girls Volleyball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-1 | |
| Fri., 10/4 | V Football | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 3:30 p.m. | W 21-8 | |
| Fri., 10/4 | V Girls Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | Win 77-62 | |
| Fri., 10/4 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 10/4 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:45 p.m. | L 0-2 | |
| Sat., 10/5 | FM Football | Wolcott | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/5 | V Girls Soccer | Portland | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | W 3-1 | |
| Mon., 10/7 | Unified Sports Soccer | Oxford | Away - Oxford HS-softball Field [Directions] | 3:00 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Naugatuck, Seymour, WCA | Away - Hop Brook Park [Directions] | 3:30 p.m. | ||
| Tue., 10/8 | V Boys Soccer | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 3:30 p.m. | W 7-1 | |
| Tue., 10/8 | V Boys Swimming and Diving | Oxford (Scrim.) | Home - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | Naugatuck, Seymour, WCA | Away - Hop Brook Park [Directions] | 3:30 p.m. | ||
| Tue., 10/8 | V Girls Soccer | Wolcott | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 2-1 | |
| Tue., 10/8 | V Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/8 | JV Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/9 | JV Girls Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Postponed | ||
| Thu., 10/10 | JV Boys Soccer | Portland | Away - Portland HS-JV Soccer Field [Directions] | Canceled | Cancelled | |
| Thu., 10/10 | V Girls Volleyball | Wilby | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/10 | JV Girls Volleyball | Wilby | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/11 | V Football | St. Paul Catholic | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | W 21-8 | |
| Fri., 10/11 | V Boys Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 3-1 | |
| Fri., 10/11 | V Boys Swimming and Diving | Sacred Heart (Scrim.) | Away - J F Kennedy HS Turf-John Reardon Pool | 6:00 p.m. | ||
| Fri., 10/11 | V Girls Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | L 0-2 | |
| Fri., 10/11 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:00 p.m. | W 3-0 | |
| Fri., 10/11 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 3:45 p.m. | W 2-0 | |
| Sat., 10/12 | FM Football | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 9:30 a.m. | ||
| Sat., 10/12 | JV Boys Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | W 6-0 | |
| Sat., 10/12 | JV Girls Soccer | Watertown | Away - Swift MS-Swift MS [Directions] | 10:00 a.m. | ||
| Mon., 10/14 | JV Girls Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 1:00 p.m. | ||
| Tue., 10/15 | V Boys Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 5-2 | |
| Tue., 10/15 | V Girls Swimming and Diving | Suffield | Away - Suffield HS-Windsor Locks Pool- No Diving [Directions] | 4:00 p.m. | Win | |
| Tue., 10/15 | V Girls Volleyball | Wolcott | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/15 | JV Girls Volleyball | Wolcott | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 10/16 | JV Boys Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 10/17 | V Boys Swimming and Diving | Wilby/Kaynor (Scrim.) | Home - Woodland HS-pool [Directions] | 5:00 p.m. | ||
| Thu., 10/17 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/17 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 10/18 | V Boys Soccer | Torrington | Away - Torrington HS [Directions] | 6:30 p.m. | W 1-0 | |
| Fri., 10/18 | JV Boys Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | V Girls Soccer | Torrington | Home - Woodland HS-Woodland Soccer Field [Directions] | 6:00 p.m. | W 6-0 | |
| Sat., 10/19 | JV Girls Soccer | Torrington | Home - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Mon., 10/21 | V Girls Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 5-1 | |
| Mon., 10/21 | V Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/21 | JV Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/22 | V Boys Soccer | Kennedy | Away - West Side MS-Waterbury-Soccer Field [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 10/22 | V Boys Swimming and Diving | Kennedy (Scrim.) | Away - John F. Kennedy HS-John Reardon Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Girls Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | T 0-0 | |
| Wed., 10/23 | JV Boys Soccer | Kennedy | Away - West Side MS-Waterbury-Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/23 | JV Girls Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 10/23 | V Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 10/23 | JV Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/24 | JV Boys Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | W 2-0 | |
| Thu., 10/24 | JV Boys Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex-Oxford Greens [Directions] | 3:45 p.m. | ||
| Thu., 10/24 | V Boys Swimming and Diving | Pomperaug (Scrim.) | Away - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:30 p.m. | W 6-2 | |
| Thu., 10/24 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/24 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/24 | FR Girls Volleyball | Shelton | Home - Woodland HS-Gym [Directions] | 3:00 p.m. | ||
| Fri., 10/25 | V Football | Sacred Heart | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | W 42-0 | |
| Fri., 10/25 | V Boys Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 3-2 | |
| Fri., 10/25 | JV Girls Soccer | Oxford | Away - Oxford HS-OHS Soccer Field-West [Directions] | Canceled | Cancelled | |
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class M Divisional Championship | Away - Wickham Park | 12:00 p.m. | ||
| Sat., 10/26 | FM Football | Sacred Heart | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field | Postponed | ||
| Sat., 10/26 | JV Boys Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | W 6-0 | |
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class SS Divisional Championship | Away - Wickham Park | 10:20 a.m. | ||
| Mon., 10/28 | V Boys Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 6:00 p.m. | W 1-0 | |
| Mon., 10/28 | V Girls Soccer | Derby | Away - Ryan Field-Football Field [Directions] | 4:30 p.m. | W 7-0 | |
| Mon., 10/28 | V Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/28 | JV Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-1 | |
| Tue., 10/29 | JV Boys Soccer | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 10/29 | JV Girls Soccer | Derby | Away - Witek Park-Soccer Field [Directions] | Canceled | Cancelled | |
| Wed., 10/30 | FM Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Wed., 10/30 | V Boys Soccer | Derby | Away - Ryan Field-Football Field [Directions] | 3:45 p.m. | W 8-1 | |
| Wed., 10/30 | V Girls Volleyball | Sacred Heart | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/30 | JV Girls Volleyball | Sacred Heart | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 10/31 | JV Boys Soccer | Derby | Away - Witek Park-Soccer Field [Directions] | Canceled | Cancelled | |
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Football | Crosby | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | W 42-14 | |
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Sat., 11/2 | V Boys Soccer | WCA | Home - Woodland HS-Woodland Soccer Field [Directions] | 1:30 p.m. | W 7-0 | |
| Sat., 11/2 | V Girls Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | 11:00 a.m. | L 3-1 | |
| Sat., 11/2 | V Girls Volleyball | TBA | Home - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 11/2 | V Girls Volleyball | Holy Cross | Home - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 11/4 | V Girls Volleyball | Naugatuck | Away - Torrington HS-High School Gym [Directions] | 5:00 p.m. | ||
| Mon., 11/4 | V Girls Volleyball | Naugatuck | Away - Torrington HS [Directions] | 5:00 p.m. | ||
| Tue., 11/5 | V Boys Soccer | Holy Cross | Home - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 11/7 | V Boys Soccer | Naugatuck | Away - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 11/8 | V Football | Ansonia | Away - Nolan Field-Ansonia-Football Field [Directions] | 6:00 p.m. | L 20-26 | |
| Sat., 11/9 | FM Football | Ansonia | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Mon., 11/11 | V Boys Soccer | Norwich Tech | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | W 5-0 | |
| Tue., 11/12 | V Girls Soccer | Immaculate | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | W 3-1 | |
| Wed., 11/13 | V Boys Soccer | Northwestern | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | W 3-2 | |
| Wed., 11/13 | V Girls Volleyball | Weston | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/14 | V Girls Soccer | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 11/14 | V Girls Swimming and Diving | CIAC Girls Class S Diving Championship | Away - Plainville HS-Pool | 5:30 p.m. | ||
| Fri., 11/15 | V Football | Oxford | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | W 35-15 | |
| Fri., 11/15 | V Boys Soccer | Ledyard | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | L 2-1 | |
| Sat., 11/16 | FM Football | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Girls Class S Trials | Away - Cheshire Community Pool | 5:15 p.m. | ||
| Tue., 11/19 | V Girls Swimming and Diving | CIAC Girls Class S Finals | Away - Moore Field House, SCSU | 6:00 p.m. | First Place - NVL Champs | |
| Thu., 11/21 | V Girls Swimming and Diving | CIAC Girls State Open Diving | Away - Middletown HS-Pool | 5:30 p.m. | ||
| Sat., 11/23 | FM Football | Seymour | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sun., 11/24 | V Girls Swimming and Diving | CIAC Girls State Open Swimming | Away - Yale | 2:00 p.m. | ||
| Wed., 11/27 | V Football | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | W 16-0 | |
| Wed., 12/4 | V Football | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 6:30 p.m. | ||
| Sat., 12/7 | V Wrestling | Shelton (Scrim.) | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 12/7 | V Girls Basketball | Griswold (Scrim.) | Away - Griswold HS-GHS Gym [Directions] | 10:00 a.m. | ||
| Fri., 12/13 | V Boys Basketball | Naugatuck, New Milford, Oxford, Pomperaug, Torrington, Wamogo, Watertown | Away - Naugatuck HS-Edward Mariano Gymnasium | 5:20 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Nonnewaug (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/17 | V Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Gym [Directions] | 7:00 p.m. | ||
| Tue., 12/17 | V Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/18 | V Wrestling | Cheshire | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/18 | JV Wrestling | Cheshire | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/18 | V Girls Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 29-23 | |
| Wed., 12/18 | JV Girls Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/19 | V Boys Basketball | Crosby | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 93-67 | |
| Thu., 12/19 | JV Boys Basketball | Crosby | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/19 | V Boys Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Thu., 12/19 | V Boys Swimming and Diving | Northwestern | Home - Woodland HS-pool [Directions] | 4:30 p.m. | ||
| Thu., 12/19 | V Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 6:00 p.m. | W 28-20 | |
| Thu., 12/19 | JV Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 12/19 | V Girls Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Crosby | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Sat., 12/21 | V Wrestling | Shelton, Bunnell, Canton, Greens Farms Academy, Masuk, Morgan, Norwalk, Notre Dame-Fairfield, Notre Dame-West Haven, St. Joseph, Weston | Away - Shelton HS-High School - Murray Gymnasium | 9:00 a.m. | ||
| Mon., 12/23 | V Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 45-63 | |
| Mon., 12/23 | JV Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/23 | FR Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/23 | V Wrestling | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | ||
| Mon., 12/23 | V Girls Basketball | Watertown | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 62-49 | |
| Mon., 12/23 | JV Girls Basketball | Watertown | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 12/27 | V Boys Basketball | Oxford | Away - Litchfield HS-Gym [Directions] | 6:00 p.m. | W 66-49 | |
| Fri., 12/27 | V Girls Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 64-40 | |
| Fri., 12/27 | JV Girls Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/27 | FR Girls Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 12/28 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:30 p.m. | W 58-48 | |
| Sat., 12/28 | V Wrestling | Trumbull Duals | Away - Trumbull HS-Aux Gym | 9:00 a.m. | ||
| Mon., 12/30 | V Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 70-83 | |
| Mon., 12/30 | JV Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/30 | FR Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/30 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 40-75 | |
| Mon., 12/30 | JV Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 12/30 | FR Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 1/2 | V Wrestling | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 5:45 p.m. | ||
| Fri., 1/3 | V Boys Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 65-74 | |
| Fri., 1/3 | JV Boys Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/3 | FR Boys Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/3 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 26-63 | |
| Fri., 1/3 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/3 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 1/4 | V Wrestling | Windham Duals | Away - Windham HS-Callahan Gymnasium | 9:30 a.m. | ||
| Mon., 1/6 | FR Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 1/7 | V Boys Swimming and Diving | Torrington | Home - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Tue., 1/7 | JV Wrestling | Foran | Home - Amity Regional HS-Aux. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/7 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | W 57-27 | |
| Tue., 1/7 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/8 | V Boys Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Wed., 1/8 | V Girls Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Thu., 1/9 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 52-45 | |
| Thu., 1/9 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:15 p.m. | ||
| Thu., 1/9 | FR Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 3:00 p.m. | ||
| Fri., 1/10 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS-CHS Pool [Directions] | 4:00 p.m. | Woodland: 78 Crosby: 62 | |
| Fri., 1/10 | V Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 46-41 | |
| Fri., 1/10 | JV Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/11 | V Wrestling | Maloney, TBA, New Haven Wrestling | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 1/11 | Winter Dance Team | Wolcott | Home - Woodland HS [Directions] | 2:00 p.m. | ||
| Mon., 1/13 | V Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 40-28 | |
| Mon., 1/13 | JV Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | V Boys Swimming and Diving | Seymour | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Woodland: 86 Seymour: 76 | |
| Tue., 1/14 | JV Wrestling | Fairfield Warde, Staples | Away - Fairfield Warde HS-Small Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/15 | V Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 56-45 | |
| Wed., 1/15 | JV Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/15 | FR Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/15 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | L 63-46 | |
| Wed., 1/15 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/16 | V Wrestling | Guilford | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/16 | JV Wrestling | Guilford | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 1/17 | V Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 74-62 | |
| Fri., 1/17 | JV Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Kennedy | Away - John F. Kennedy HS-John Reardon Pool [Directions] | 4:00 p.m. | Woodland: 97 Kennedy: 73 | |
| Fri., 1/17 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | W 39-37 | |
| Fri., 1/17 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 1/18 | V Wrestling | New Milford Wrestling Tournament | Away - New Milford HS-Main Gym - NMHS | Canceled | Cancelled | |
| Sat., 1/18 | FR Girls Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Mon., 1/20 | JV Wrestling | Notre Dame-West Haven | Away - Notre Dame HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/22 | V Boys Basketball | Derby | Away - Derby HS-Gym [Directions] | 7:00 p.m. | W 66-62 | |
| Wed., 1/22 | JV Boys Basketball | Derby | Away - Derby HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/22 | V Wrestling | Daniel Hand | Away - Polson MS, Madison-Polson Big Gym/DHHS Campus [Directions] | 6:30 p.m. | ||
| Wed., 1/22 | V Girls Basketball | Derby | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | W 47-29 | |
| Wed., 1/22 | JV Girls Basketball | Derby | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/24 | V Boys Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | L 48-63 | |
| Fri., 1/24 | JV Boys Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Fri., 1/24 | FR Boys Basketball | Torrington | Away - Torrington HS [Directions] | 3:30 p.m. | ||
| Fri., 1/24 | V Boys Swimming and Diving | Holy Cross | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Woodland: 77 Holy Cross: 100 | |
| Fri., 1/24 | V Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 65-47 | |
| Fri., 1/24 | JV Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/25 | V Wrestling | 2020 Ridgefield Challenge | Away - Ridgefield HS-Main Gym | 9:00 a.m. | ||
| Sat., 1/25 | JV Wrestling | Godleski Invitational JV Tournament | Away - Norwalk HS-Tom Scarso Gymnasium | 9:00 a.m. | ||
| Mon., 1/27 | Unified Sports Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 3:00 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Sacred Heart | Away - Sacred Heart HS-Alumni Hall | 7:00 p.m. | L 50-69 | |
| Tue., 1/28 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart HS-Alumni Hall | 5:15 p.m. | ||
| Tue., 1/28 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart HS-Alumni Hall | Postponed | ||
| Tue., 1/28 | V Boys Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Woodland 100 Naugatuck 84 | |
| Tue., 1/28 | V Girls Basketball | Sacred Heart | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 50-40 | |
| Tue., 1/28 | JV Girls Basketball | Sacred Heart | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/29 | V Wrestling | Xavier | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/29 | JV Wrestling | Xavier | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/30 | V Boys Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Thu., 1/30 | JV Wrestling | East Haven | Home - Amity Regional HS-Aux. Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/30 | V Girls Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Fri., 1/31 | V Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 42-40 | |
| Fri., 1/31 | JV Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Sacred Heart | Away - John F. Kennedy HS-John Reardon Pool | 7:00 p.m. | Woodland 94 Sacred Heart 86 | |
| Fri., 1/31 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | L 47-34 | |
| Fri., 1/31 | JV Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:15 p.m. | ||
| Fri., 1/31 | Unified Sports Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 2/1 | V Wrestling | Hastings Duals | Away - Newington HS-Gym | 9:00 a.m. | ||
| Sat., 2/1 | FR Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Tue., 2/4 | V Wrestling | Branford | Away - Branford HS-Gym [Directions] | 6:30 p.m. | ||
| Tue., 2/4 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | W 48-40 | |
| Tue., 2/4 | JV Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:15 p.m. | ||
| Tue., 2/4 | Winter Dance Team | NVL Dance Competition | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/5 | V Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 72-55 | |
| Wed., 2/5 | JV Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 44-81 | |
| Fri., 2/7 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/7 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Woodland 91 Wilby 83 | |
| Fri., 2/7 | V Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 56-39 | |
| Fri., 2/7 | JV Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/8 | V Wrestling | Foran Duals | Away - Foran HS -Edna L. Fraser Gymnasium | 9:00 a.m. | ||
| Tue., 2/11 | V Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 42-46 | |
| Tue., 2/11 | JV Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/11 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Tue., 2/11 | V Girls Basketball | Derby | Away - Derby HS-Gym [Directions] | 5:30 p.m. | W 46-44 Ot | |
| Tue., 2/11 | JV Girls Basketball | Derby | Away - Derby HS-Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/12 | V Wrestling | East Haven | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 2/12 | JV Wrestling | East Haven | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 2/13 | V Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | L 58-61 | |
| Thu., 2/13 | JV Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/13 | FR Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/13 | V Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 60-46 | |
| Thu., 2/13 | JV Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 2/13 | FR Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/14 | JV Wrestling | Branford, Cheshire, Daniel Hand, East Haven, Fairfield Prep, Guilford, Jonathan Law, Foran, Morgan, Notre Dame-West Haven, Shelton, New Haven Wrestling, Xavier | Home - Mercy HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 2/15 | V Wrestling | Branford, Cheshire, Daniel Hand, East Haven, Fairfield Prep, Guilford, Jonathan Law, Foran, Morgan, TBA, Notre Dame-West Haven, Shelton, West Haven, New Haven Wrestling, Xavier | Home - Mercy HS-Gym [Directions] | 9:00 a.m. | ||
| Mon., 2/17 | JV Wrestling | JV Tournament - Pomperaug | Away - Not Listed | 9:00 a.m. | ||
| Tue., 2/18 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:00 p.m. | ||
| Tue., 2/18 | V Girls Basketball | Wilby | Away - Wilby HS-Gym [Directions] | 7:00 p.m. | W 57-20 | |
| Tue., 2/18 | JV Girls Basketball | Wilby | Away - Wilby HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/20 | V Boys Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 7:00 p.m. | W 69-61 | |
| Thu., 2/20 | JV Boys Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/20 | FR Boys Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 2/21 | V Wrestling | CIAC Class L Divisional Championship | Away - Bristol Central-Charles C. Marsh Gymnasium | 3:00 p.m. | ||
| Sat., 2/22 | V Wrestling | CIAC Class L Divisional Championship | Away - Bristol Central-Charles C. Marsh Gymnasium | 9:00 a.m. | ||
| Sat., 2/22 | V Girls Basketball | Holy Cross | Away - Holy Cross-gym [Directions] | 12:45 p.m. | ||
| Tue., 2/25 | V Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 7:00 p.m. | W 66-50 | |
| Tue., 2/25 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/25 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 2/25 | Unified Sports Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 3:00 p.m. | ||
| Thu., 2/27 | V Boys Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 58 51 | |
| Thu., 2/27 | JV Boys Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/27 | FR Boys Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/28 | V Boys Swimming and Diving | NVL Diving Championship | Away - Watertown High-WHS Pool | 6:00 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 3:00 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center-Field House | 3:15 p.m. | ||
| Fri., 2/28 | V Girls Basketball | Oxford (Scrim.) | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Sat., 2/29 | V Boys Swimming and Diving | Crosby/WCA, Ansonia, Kennedy, TBA, TBA, Naugatuck, Oxford, Sacred Heart, Seymour, Torrington, WCA, Watertown, Wilby/Kaynor, Wolcott | Away - John F. Kennedy HS-John Reardon Pool | 11:00 a.m. | ||
| Sat., 2/29 | V Boys Swimming and Diving | Sacred Heart, Ansonia, Crosby/WCA, Holy Cross, Kennedy, TBA, TBA, Naugatuck, Oxford, Seymour, Torrington, WCA, Watertown, Wilby/Kaynor, Wolcott | Away - John F. Kennedy HS-John Reardon Pool | 5:00 p.m. | ||
| Sat., 2/29 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center-Field House | 10:00 a.m. | ||
| Sat., 2/29 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 9:00 a.m. | ||
| Sat., 2/29 | V Competitive Cheerleading | Bunnell | Home - Woodland HS-Gym [Directions] | 9:10 a.m. | ||
| Mon., 3/2 | V Girls Basketball | Valley Regional | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/5 | V Girls Basketball | Cromwell | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | ||
| Sat., 3/7 | V Wrestling | New England Wrestling Championships @ Methuen, MA | Away - Not Listed | 9:00 a.m. | ||
| Tue., 3/10 | V Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | Canceled | Cancelled | |
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Boys Class S Diving Championship | Away - Plainville HS-Pool | Canceled | Cancelled | |
| Fri., 3/13 | V Co-ed Weightlifting | NVL Weightlifting Competition | Away - Seymour HS-Gym | Cancelled | ||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Boys Class S Trials | Away - Cheshire Community Pool | Canceled | Cancelled | |
| Wed., 3/18 | V Boys Swimming and Diving | CIAC Boys Class S Finals | Away - Wesleyan University-Pool | Canceled | Cancelled | |
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Boys State Open Diving | Away - Bulkeley HS-Pool | Canceled | Cancelled | |
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Boys State Open Swimming | Away - Yale | Canceled | Cancelled | |
| Thu., 3/26 | V Softball | Trumbull (Scrim.) | Away - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | Cancelled | |
| Sat., 3/28 | V Baseball | Pomperaug (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | Cancelled | |
| Tue., 3/31 | V Baseball | Stratford (Scrim.) | Away - Penders Field-Penders Field - Stratford [Directions] | Cancelled | Cancelled | |
| Wed., 4/1 | V Baseball | East Hartford (Scrim.) | Away - McKenna Field-Baseball Diamond [Directions] | Cancelled | Cancelled | |
| Wed., 4/1 | V Softball | Masuk (Scrim.) | Away - Masuk HS-Masuk High School Softball Field [Directions] | Cancelled | ||
| Thu., 4/2 | V Softball | Brookfield (Scrim.) | Away - Brookfield HS-BHS Softball Field [Directions] | Cancelled | ||
| Fri., 4/3 | V Softball | WCA (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | Cancelled | |
| Mon., 4/6 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | Cancelled | ||
| Mon., 4/6 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/6 | V Girls Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/7 | V Baseball | Sacred Heart | Away - Fulton Park-Baseball Diamond | Cancelled | ||
| Tue., 4/7 | V Boys Outdoor Track | Holy Cross, Oxford | Away - Holy Cross-Holy Cross Track [Directions] | Cancelled | ||
| Tue., 4/7 | V Girls Outdoor Track | Holy Cross, Oxford | Away - Holy Cross-Holy Cross Track [Directions] | Cancelled | ||
| Tue., 4/7 | V Softball | Sacred Heart | Away - Municipal Stadium-Joan Joyce Softball Diamond | Cancelled | ||
| Wed., 4/8 | V Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/8 | JV Baseball | Sacred Heart | Away - Fulton Park-Baseball Diamond | Cancelled | ||
| Wed., 4/8 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | Cancelled | ||
| Wed., 4/8 | V Boys Tennis | Sacred Heart | Away - Fulton Park-Tennis Courts | Cancelled | ||
| Wed., 4/8 | V Softball | Wolcott | Away - Wolcott HS-George Babcock Softball Field [Directions] | Cancelled | ||
| Wed., 4/8 | V Girls Tennis | Sacred Heart | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/9 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Thu., 4/9 | V Boys Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/9 | JV Softball | Wolcott | Away - Wolcott HS-JV Softball Field [Directions] | Cancelled | ||
| Thu., 4/9 | V Girls Tennis | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | Cancelled | ||
| Fri., 4/10 | JV Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 4/11 | V Baseball | Thomaston | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 4/13 | V Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 4/13 | FR Baseball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Mon., 4/13 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/13 | V Softball | Wilby | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/13 | V Girls Tennis | St. Paul Catholic | Away - St. Paul Catholic HS-Page Park, Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/14 | JV Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 4/14 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | Cancelled | ||
| Tue., 4/14 | V Boys Outdoor Track | Sacred Heart, Wilby | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Tue., 4/14 | V Girls Outdoor Track | Sacred Heart, Wilby | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Tue., 4/14 | JV Softball | Wilby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Wed., 4/15 | V Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | Cancelled | ||
| Wed., 4/15 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/15 | V Softball | Crosby | Away - Crosby HS-CHS Softball Field #1 [Directions] | Cancelled | ||
| Wed., 4/15 | JV Softball | Crosby | Away - Crosby HS-CHS Softball Field #2 [Directions] | Cancelled | ||
| Wed., 4/15 | V Girls Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/17 | V Baseball | Derby | Away - Payden Park-Payden Field [Directions] | Cancelled | ||
| Fri., 4/17 | V Boys Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/17 | V Softball | Derby | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Fri., 4/17 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | Cancelled | ||
| Sat., 4/18 | JV Baseball | Derby | Away - Amendola Field Derby Var-Baseball Field [Directions] | Cancelled | ||
| Sat., 4/18 | JV Softball | Derby | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/20 | V Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 4/20 | FR Baseball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Mon., 4/20 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | Cancelled | ||
| Mon., 4/20 | V Softball | Naugatuck | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Tue., 4/21 | JV Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 4/21 | V Boys Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS-WHS Track and Lower Field [Directions] | Cancelled | ||
| Tue., 4/21 | V Girls Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS-WHS Track and Lower Field [Directions] | Cancelled | ||
| Tue., 4/21 | JV Softball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Wed., 4/22 | V Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/22 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | Cancelled | ||
| Wed., 4/22 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/22 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | Cancelled | ||
| Wed., 4/22 | V Girls Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/23 | JV Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Thu., 4/23 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | Cancelled | ||
| Thu., 4/23 | JV Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | Cancelled | ||
| Fri., 4/24 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | Cancelled | ||
| Fri., 4/24 | V Boys Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/24 | V Softball | Ansonia | Away - Ansonia HS-Charger Field [Directions] | Cancelled | Cancelled | |
| Fri., 4/24 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | Cancelled | Cancelled | |
| Mon., 4/27 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 4/27 | FR Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Tennis | Holy Cross | Away - Holy Cross [Directions] | Cancelled | ||
| Mon., 4/27 | V Softball | Torrington | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/28 | JV Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | Cancelled | ||
| Tue., 4/28 | V Boys Outdoor Track | Kennedy, Torrington | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Tue., 4/28 | V Girls Outdoor Track | Kennedy, Torrington | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Tue., 4/28 | JV Softball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | Cancelled | |
| Wed., 4/29 | V Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/29 | FR Baseball | Wolcott | Away - BAW - B Field [Directions] | Cancelled | ||
| Wed., 4/29 | V Boys Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/29 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | Cancelled | Cancelled | |
| Wed., 4/29 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/30 | JV Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 5/1 | V Baseball | Watertown | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 5/1 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | Cancelled | ||
| Fri., 5/1 | V Softball | Watertown | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Fri., 5/1 | V Girls Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Sat., 5/2 | JV Baseball | Watertown | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 5/2 | JV Softball | Watertown | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 5/4 | V Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | Cancelled | ||
| Mon., 5/4 | V Softball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/5 | JV Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | Cancelled | ||
| Tue., 5/5 | V Boys Outdoor Track | Derby, St. Paul Catholic | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | Cancelled | ||
| Tue., 5/5 | V Girls Outdoor Track | Derby, St. Paul Catholic | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | Cancelled | ||
| Tue., 5/5 | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | Cancelled | ||
| Wed., 5/6 | V Boys Tennis | Sacred Heart | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 5/6 | V Softball | Shepaug Valley | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | Cancelled | |
| Fri., 5/8 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 5/8 | FR Baseball | St. Paul Catholic | Away - Page Park [Directions] | Cancelled | ||
| Fri., 5/8 | V Boys Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Fri., 5/8 | V Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Fri., 5/8 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Chase Park [Directions] | Cancelled | ||
| Sat., 5/9 | V Baseball | Kolbe Cathedral | Away - Kolbe-cathedral HS-Seaside Park [Directions] | Cancelled | ||
| Sat., 5/9 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 5/9 | JV Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 5/11 | V Baseball | Ansonia | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 5/11 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | Cancelled | ||
| Mon., 5/11 | V Boys Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 5/11 | V Softball | Ansonia | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 5/11 | V Girls Tennis | Seymour | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Outdoor Track | Seymour, WCA | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Tue., 5/12 | V Girls Outdoor Track | Seymour, WCA | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Wed., 5/13 | V Baseball | Derby | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/13 | V Boys Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 5/13 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | Cancelled | Cancelled | |
| Wed., 5/13 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | Cancelled | ||
| Thu., 5/14 | JV Baseball | Derby | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Thu., 5/14 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | Cancelled | ||
| Thu., 5/14 | JV Softball | Derby | Away - Amendola Field Derby Var-Softball Field [Directions] | Cancelled | Cancelled | |
| Fri., 5/15 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | Cancelled | ||
| Fri., 5/15 | V Boys Outdoor Track | O'Brien Tech, Platt Tech, Kaynor Tech | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Fri., 5/15 | V Girls Outdoor Track | O'Brien Tech, Platt Tech, Kaynor Tech | Home - Woodland HS-Track [Directions] | Cancelled | ||
| Fri., 5/15 | V Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Sat., 5/16 | JV Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | Cancelled | ||
| Sat., 5/16 | JV Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 5/18 | V Baseball | Seymour | Away - French Park [Directions] | Cancelled | Cancelled | |
| Mon., 5/18 | FR Baseball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Mon., 5/18 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | Cancelled | ||
| Mon., 5/18 | V Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Tue., 5/19 | V Baseball | WCA | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 5/19 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | Cancelled | ||
| Tue., 5/19 | V Softball | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | Cancelled | ||
| Wed., 5/20 | JV Baseball | WCA | Home - Woodland HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/20 | JV Softball | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Thu., 5/21 | JV Baseball | Seymour | Away - French Park [Directions] | Cancelled | ||
| Thu., 5/21 | JV Softball | Kennedy | Away - Town Plot Park [Directions] | Cancelled | ||
| Wed., 5/27 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | Cancelled | ||