| Woodland 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 514 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Baseball | Coventry (Scrim.) | Home - Woodland HS Baseball Field [Directions] | TBA | W 9-2 | |
| TBA | JV Baseball | Seymour | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| TBA | JV Baseball | Goodwin Tech | Away - Goodwin Tech HS Field [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Wolcott | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Sacred Heart | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Torrington | Away - Torrington HS [Directions] | TBA | ||
| TBA | JV Baseball | Oxford | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Naugatuck | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | WCA | Away - Washington Park [Directions] | TBA | ||
| TBA | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | TBA | ||
| TBA | JV Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | FR Baseball | Torrington | Away - Torrington HS [Directions] | TBA | ||
| TBA | FR Baseball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | FM Football | Torrington | Away - Torrington HS [Directions] | TBA | ||
| TBA | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | TBA | ||
| TBA | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Girls Soccer | Derby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Holy Cross | Home - Woodland HS Varsity Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Softball | Brookfield | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 12:00 p.m. | ||
| TBA | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Home - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Watertown | Away - Veterans Park [Directions] | TBA | ||
| TBA | JV Softball | Oxford | Home - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Seymour | Home - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Crosby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Softball | Wilby | Away - Bucks Hill Park [Directions] | TBA | ||
| TBA | JV Softball | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Softball | Morgan | Away - Morgan H.S. [Directions] | TBA | ||
| Tue., 1/3 | V Girls Soccer | Amity (Scrim.) | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 1/3 | V Girls Soccer | Amity (Scrim.) | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 8/26 | V Football | Hopkins School (Scrim.) | Away - Hopkins School | 8:00 a.m. | ||
| Mon., 8/28 | V Boys Soccer | Oxford (Scrim.) | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Mon., 8/28 | V Girls Soccer | Lewis Mills (Scrim.) | Away - Lewis Mills JV Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 8/28 | V Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:00 p.m. | ||
| Mon., 8/28 | JV Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:00 p.m. | ||
| Thu., 8/31 | V Football | Newington (Scrim.) | Away - Alumni VAR Field on Alumni Road - LIGHTS [Directions] | 6:15 p.m. | ||
| Thu., 8/31 | V Boys Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Fri., 9/1 | V Girls Soccer | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 4:30 p.m. | ||
| Sat., 9/2 | V Girls Volleyball | East Haven Jamboree | Away - East Haven HS | TBA | ||
| Tue., 9/5 | V Girls Volleyball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/5 | V Girls Volleyball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/6 | V Girls Soccer | Nonnewaug (Scrim.) | Away - NHS Varsity Soccer Field [Directions] | 3:30 p.m. | ||
| Wed., 9/6 | V Girls Soccer | Nonnewaug (Scrim.) | Away - NHS Varsity Soccer Field [Directions] | Cancelled | Cancelled | |
| Fri., 9/8 | V Football | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 7:00 p.m. | W 34-30 | |
| Fri., 9/8 | V Boys Soccer | Seymour | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | L 0-1 | |
| Fri., 9/8 | V Girls Swimming and Diving | Jonathan Law | Away - Foran HS Pool [Directions] | 5:00 p.m. | Win 96-90 | |
| Fri., 9/8 | V Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/8 | JV Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | 4:45 p.m. | L 1-2 | |
| Sat., 9/9 | JV Football | Naugatuck | Away - Naugatuck HS [Directions] | 11:00 a.m. | ||
| Sat., 9/9 | JV Boys Soccer | Seymour | Home - Woodland Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 9/9 | V Girls Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 11:00 a.m. | W 4-1 | |
| Sat., 9/9 | V Girls Volleyball | Brookfield | Home - Woodland HS Gym [Directions] | 1:00 p.m. | L 1-3 | |
| Sat., 9/9 | JV Girls Volleyball | Brookfield | Home - Woodland HS Gym [Directions] | 11:30 a.m. | W 2-0 | |
| Mon., 9/11 | JV Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Naugatuck, Kennedy, Seymour | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Kennedy | Away - West Side MS [Directions] | 3:30 p.m. | W 3-0 | |
| Tue., 9/12 | V Girls Cross Country | Naugatuck, Kennedy, Seymour | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | L 1-2 | |
| Tue., 9/12 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Home - Woodland HS Pool [Directions] | 5:00 p.m. | Win 94-81 | |
| Tue., 9/12 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 9/12 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 4:45 p.m. | L 1-2 | |
| Wed., 9/13 | JV Boys Soccer | Kennedy | Away - West Side MS [Directions] | 3:30 p.m. | ||
| Wed., 9/13 | JV Girls Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 9/14 | JV Boys Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 9/15 | V Football | Watertown | Home - Woodland Football Field [Directions] | 6:30 p.m. | L 21-42 | |
| Fri., 9/15 | V Boys Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | 4:00 p.m. | L 0-4 | |
| Fri., 9/15 | V Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 9/15 | V Girls Swimming and Diving | Suffield | Home - Woodland HS Pool [Directions] | 4:30 p.m. | Win 94-83 | |
| Fri., 9/15 | V Girls Volleyball | Oxford | Home - Woodland HS Gym [Directions] | 5:00 p.m. | W 3-2 | |
| Fri., 9/15 | JV Girls Volleyball | Oxford | Home - Woodland HS Gym [Directions] | 3:45 p.m. | L 0-2 | |
| Sat., 9/16 | FM Football | WCA | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/16 | V Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 10:00 a.m. | L 0-3 | |
| Sat., 9/16 | V Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 12:00 p.m. | W 1-0 | |
| Tue., 9/19 | V Boys Cross Country | Wilby, St. Paul Catholic, WCA | Home - Woodland HS [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 4:30 p.m. | W 7-1 | |
| Tue., 9/19 | V Girls Cross Country | Wilby, St. Paul Catholic, WCA | Home - Woodland HS [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Girls Soccer | Derby | Home - Woodland Soccer Field [Directions] | 3:00 p.m. | W 9-0 | |
| Tue., 9/19 | V Girls Swimming and Diving | Watertown | Home - Woodland HS Pool [Directions] | 4:00 p.m. | Win 100 - 86 | |
| Tue., 9/19 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/19 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 9/20 | JV Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Football | Sacred Heart | Away - Municipal Stadium | 6:00 p.m. | W 57-30 | |
| Thu., 9/21 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | W 7-2 | |
| Fri., 9/22 | V Girls Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 9/22 | V Girls Swimming and Diving | Seymour | Away - Seymour HS [Directions] | 4:00 p.m. | Loss - 71-94 | |
| Fri., 9/22 | V Girls Volleyball | Wolcott | Away - Wolcott HS [Directions] | 6:00 p.m. | L 2-3 | |
| Fri., 9/22 | JV Girls Volleyball | Wolcott | Away - Wolcott HS [Directions] | 4:45 p.m. | L 0-2 | |
| Sat., 9/23 | FM Football | Sacred Heart | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | JV Girls Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 10:00 a.m. | ||
| Tue., 9/26 | V Boys Cross Country | Crosby, Torrington, Wolcott | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | T 2-2 | |
| Tue., 9/26 | V Girls Cross Country | Crosby, Torrington, Wolcott | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | W 3-2 | |
| Tue., 9/26 | V Girls Swimming and Diving | Sacred Heart | Home - Woodland HS Pool [Directions] | 4:00 p.m. | Win 101-77 | |
| Tue., 9/26 | V Girls Volleyball | WCA | Home - Woodland HS Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Tue., 9/26 | JV Girls Volleyball | WCA | Home - Woodland HS Gym [Directions] | 3:45 p.m. | W 2-1 | |
| Wed., 9/27 | JV Boys Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Thu., 9/28 | JV Boys Soccer | Wilby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 9/28 | JV Girls Soccer | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | ||
| Thu., 9/28 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:15 p.m. | W 3-1 | |
| Thu., 9/28 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:45 p.m. | L 0-2 | |
| Fri., 9/29 | V Football | Naugatuck | Home - Woodland Football Field [Directions] | 6:30 p.m. | L 6-35 | |
| Fri., 9/29 | V Boys Soccer | Wilby | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 5-0 | |
| Fri., 9/29 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | Win 89-63 | |
| Fri., 9/29 | V Girls Volleyball | Kennedy | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/29 | JV Girls Volleyball | Kennedy | Home - Woodland HS Gym [Directions] | 4:45 p.m. | L 0-2 | |
| Sat., 9/30 | FM Football | Wilby | Away - Wilby H.S. [Directions] | 10:00 a.m. | ||
| Tue., 10/3 | V Boys Cross Country | Ansonia, Oxford, Watertown | Away - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Boys Soccer | Wolcott | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/3 | V Girls Cross Country | Ansonia, Oxford, Watertown | Away - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | W 4-2 | |
| Tue., 10/3 | V Girls Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | Win 82-68 | |
| Tue., 10/3 | V Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/3 | JV Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/4 | JV Boys Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 10/4 | JV Girls Soccer | Wolcott | Away - Wolcott HS, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | V Football | Oxford | Home - Woodland Football Field [Directions] | 6:30 p.m. | L 14-42 | |
| Fri., 10/6 | V Boys Soccer | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/6 | JV Boys Soccer | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | V Girls Soccer | Torrington | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 5-0 | |
| Fri., 10/6 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Home - Woodland HS Pool [Directions] | 3:45 p.m. | Win 89-63 | |
| Fri., 10/6 | V Girls Volleyball | Watertown | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/6 | JV Girls Volleyball | Watertown | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/7 | FM Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Tue., 10/10 | V Boys Cross Country | Holy Cross, Sacred Heart, Derby | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/10 | V Girls Cross Country | Holy Cross, Sacred Heart, Derby | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Girls Soccer | Oxford | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 6-1 | |
| Tue., 10/10 | JV Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | JV Boys Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Wed., 10/11 | JV Girls Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | V Girls Swimming and Diving | Torrington | Home - Woodland HS Pool [Directions] | 4:00 p.m. | win 92-84 | |
| Wed., 10/11 | V Girls Volleyball | Wilby | Home - Woodland HS Gym [Directions] | 3:00 p.m. | W 3-0 | |
| Thu., 10/12 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/12 | JV Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 4:45 p.m. | ||
| Fri., 10/13 | V Boys Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 4-1 | |
| Fri., 10/13 | V Girls Soccer | Sacred Heart | Away - Waterville Park | 3:45 p.m. | W 9-0 | |
| Fri., 10/13 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland HS Pool [Directions] | 4:00 p.m. | Win - 94-81 | |
| Fri., 10/13 | V Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/13 | JV Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Sat., 10/14 | JV Boys Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | 1:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Holy Cross | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 2-1 | |
| Tue., 10/17 | V Girls Soccer | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | 6:00 p.m. | L 1-0 | |
| Tue., 10/17 | V Girls Swimming and Diving | Oxford | Home - Woodland HS Pool [Directions] | 5:00 p.m. | Win 96-87 | |
| Tue., 10/17 | V Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/17 | JV Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | NVL Championships | Away | TBA | ||
| Wed., 10/18 | JV Boys Soccer | Holy Cross | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Wed., 10/18 | V Girls Cross Country | NVL Championships | Away | TBA | ||
| Wed., 10/18 | JV Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 10/18 | V Girls Volleyball | East Haven | Away - East Haven HS [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/18 | JV Girls Volleyball | East Haven | Away - East Haven HS [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | L 0-2 | |
| Thu., 10/19 | V Girls Soccer | Ansonia | Home - Woodland Football Field [Directions] | 6:00 p.m. | W 9-0 | |
| Fri., 10/20 | V Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:30 p.m. | L 45-64 | |
| Fri., 10/20 | JV Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | ||
| Fri., 10/20 | V Girls Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | Win 89-67 | |
| Fri., 10/20 | V Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 10/20 | JV Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 4:45 p.m. | ||
| Sat., 10/21 | JV Football | Crosby | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/21 | V Girls Soccer | Masuk | Home - Woodland Soccer Field [Directions] | 12:00 p.m. | W 2-0 | |
| Mon., 10/23 | V Boys Cross Country | Platt Tech Invitational | Away - Eisenhower Park, Milford | 3:00 p.m. | ||
| Mon., 10/23 | V Boys Soccer | WCA | Away - Municipal Stadium [Directions] | 5:30 p.m. | W 6-1 | |
| Mon., 10/23 | V Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 2-1 | |
| Mon., 10/23 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 6:00 p.m. | L 1-3 | |
| Mon., 10/23 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 10/25 | V Boys Soccer | Crosby | Home - Woodland Football Field [Directions] | 6:00 p.m. | W 4-1 | |
| Wed., 10/25 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 4-0 | |
| Wed., 10/25 | V Girls Volleyball | Wolcott | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/25 | JV Girls Volleyball | Wolcott | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Thu., 10/26 | JV Boys Soccer | Crosby | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 10/27 | FM Football | St. Paul Catholic | Home - Woodland Football Field [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | JV Girls Volleyball | Naugy JV tournament | Away - Naugatuck HS | 3:00 p.m. | ||
| Sat., 10/28 | V Boys Cross Country | State Class Tournament | Away | TBA | ||
| Sat., 10/28 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 1:00 p.m. | W 15-8 | |
| Sat., 10/28 | V Boys Soccer | Ansonia | Home - Woodland Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/28 | V Girls Cross Country | State Class Tournament | Away | TBA | ||
| Sat., 10/28 | V Girls Soccer | Seymour | Home - Woodland Soccer Field [Directions] | 11:00 a.m. | W 7-1 | |
| Sat., 10/28 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 1:00 p.m. | ||
| Sat., 10/28 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 1:00 p.m. | ||
| Mon., 10/30 | V Boys Soccer | NVL Semi-Finals | Away - Crosby HS | TBA | ||
| Mon., 10/30 | V Girls Volleyball | Torrington | Away - Kennedy HS [Directions] | 5:00 p.m. | ||
| Mon., 10/30 | V Girls Volleyball | NVL Semi-Finals | Away - Kennedy HS | TBA | ||
| Tue., 10/31 | V Girls Soccer | St. Paul Catholic | Away - Torrington HS [Directions] | 5:00 p.m. | ||
| Wed., 11/1 | V Boys Soccer | NVL Championships | Away - Seymour HS | 5:00 p.m. | ||
| Thu., 11/2 | V Girls Soccer | NVL Championships | Away - Seymour HS | 5:00 p.m. | ||
| Thu., 11/2 | V Girls Volleyball | NVL Championships | Away - TBA | TBA | ||
| Thu., 11/2 | V Girls Volleyball | NVL Championships | Away - TBA | TBA | ||
| Fri., 11/3 | V Football | Torrington | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 39-28 | |
| Mon., 11/6 | V Boys Soccer | Wolcott Tech | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Mon., 11/6 | V Boys Soccer | Wolcott Tech | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | W 502 | |
| Mon., 11/6 | V Girls Volleyball | Waterford | Away - Francis X. Sweeney Field House [Directions] | 6:00 p.m. | ||
| Mon., 11/6 | V Girls Volleyball | Waterford | Away - Waterford HS gym [Directions] | 6:00 p.m. | ||
| Tue., 11/7 | V Girls Soccer | Wilcox Tech | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Thu., 11/9 | V Football | Kennedy | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 49-12 | |
| Thu., 11/9 | V Girls Soccer | Cromwell | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Bulkeley HS [Directions] | 4:30 p.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 2:00 p.m. | ||
| Mon., 11/13 | FM Football | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/18 | JV Football | Seymour | Home - Woodland Football Field [Directions] | 11:00 a.m. | ||
| Sat., 11/18 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Wed., 11/22 | V Football | Seymour | Away - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 8-56 | |
| Sat., 12/2 | V Girls Basketball | Griswold (Scrim.) | Away - GHS Gym [Directions] | 10:00 a.m. | ||
| Tue., 12/5 | V Girls Basketball | Terryville (Scrim.) | Away [Directions] | 5:40 p.m. | ||
| Thu., 12/7 | V Boys Basketball | Gilbert (Scrim.) | Home - Woodland HS Gym [Directions] | 6:30 p.m. | ||
| Tue., 12/12 | V Boys Basketball | Abbott Tech (Scrim.) | Home - Woodland HS Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/12 | V Wrestling | Cheshire | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Tue., 12/12 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | W 41-29 | |
| Tue., 12/12 | JV Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 12/16 | V Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS Gym [Directions] | 8:00 a.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Reindeer Relays | Away - Wilton HS | 9:00 a.m. | ||
| Sat., 12/16 | V Wrestling | Shelton Invitational | Away | 10:00 a.m. | ||
| Tue., 12/19 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 44-64 | |
| Tue., 12/19 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Tue., 12/19 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | ||
| Tue., 12/19 | V Boys Swimming and Diving | Oxford | Away - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 12/19 | V Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 33-63 | |
| Tue., 12/19 | JV Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/20 | V Wrestling | East Haven | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Thu., 12/21 | V Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 53-62 | |
| Thu., 12/21 | JV Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/21 | FR Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Thu., 12/21 | V Boys Indoor Track | Old Saybrook Qualifier | Away | 5:00 p.m. | two buses | |
| Thu., 12/21 | V Boys Swimming and Diving | Northwestern | Home - Woodland Pool [Directions] | 4:30 p.m. | ||
| Thu., 12/21 | V Girls Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 6:00 p.m. | W 56-44 | |
| Thu., 12/21 | JV Girls Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/27 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:00 p.m. | W 67-60(OT) | |
| Wed., 12/27 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 2:15 p.m. | ||
| Wed., 12/27 | V Wrestling | Frank Chaves Invitational, Simsbury | Away | 10:00 a.m. | ||
| Wed., 12/27 | V Girls Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 41-34 | |
| Wed., 12/27 | JV Girls Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/28 | V Boys Indoor Track | H-K invitational | Away - New Haven Field House | TBA | ||
| Thu., 12/28 | V Wrestling | New Haven Wrestling, Guilford | Away - Wilbur Cross H. S. [Directions] | 7:00 p.m. | Amity Will Not be Wrestling Guilford | |
| Fri., 12/29 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | W 58-41 | |
| Fri., 12/29 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/29 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 12/29 | V Girls Basketball | Crosby | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 40-50 | |
| Fri., 12/29 | JV Girls Basketball | Crosby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/30 | V Wrestling | Southington Duals | Away | 9:00 a.m. | ||
| Wed., 1/3 | V Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 55-50 | |
| Wed., 1/3 | JV Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/3 | FR Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/3 | V Wrestling | Daniel Hand | Away - Polson Gym/DHHS Campus [Directions] | 7:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | L 47-49 | |
| Wed., 1/3 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Sat., 1/6 | V Boys Indoor Track | Elm City Relays | Away - New Haven Field House | TBA | ||
| Sat., 1/6 | V Wrestling | Bethel, New Haven Wrestling | Home - Paul D. Mengold Gym at Amity HS [Directions] | 9:00 a.m. | ||
| Tue., 1/9 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 39-69 | |
| Tue., 1/9 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Wrestling | Shelton | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | L 34-53 | |
| Tue., 1/9 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:30 p.m. | ||
| Wed., 1/10 | V Boys Basketball | Wilby | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 56-65 | |
| Wed., 1/10 | JV Boys Basketball | Wilby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/10 | FR Boys Basketball | Wilby | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/10 | V Girls Basketball | Wilby | Away - Wilby H.S. [Directions] | 7:00 p.m. | W 58-35 | |
| Wed., 1/10 | JV Girls Basketball | Wilby | Away - Wilby H.S. [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | L 38-83 | |
| Fri., 1/12 | JV Boys Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Fri., 1/12 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Torrington | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 56-47 | |
| Fri., 1/12 | JV Girls Basketball | Torrington | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/13 | V Boys Indoor Track | Fresh/Soph Glastonbury Relays | Away - Glastonbury HS | TBA | ||
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invite | Away - New Haven Field House | TBA | ||
| Sat., 1/13 | V Wrestling | Gilbert Duals | Away - Gilbert School, Winsted, CT | Cancelled | Cancelled | |
| Sat., 1/13 | FR Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 3:00 p.m. | ||
| Tue., 1/16 | V Boys Swimming and Diving | Seymour | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Thu., 1/18 | V Boys Basketball | Oxford | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 53-52 | |
| Thu., 1/18 | JV Boys Basketball | Oxford | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/18 | FR Boys Basketball | Jonathan Law | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/18 | V Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 5:00 p.m. | L 37-47 | |
| Fri., 1/19 | V Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 7:00 p.m. | L 29-78 | |
| Fri., 1/19 | JV Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | WCA | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 52-49 | |
| Fri., 1/19 | JV Girls Basketball | WCA | Home - Woodland HS Gym [Directions] | 5:00 p.m. | ||
| Sat., 1/20 | V Boys Indoor Track | Shoreline Coaches Invite | Away - New Haven Field House | TBA | 1 bus | |
| Sat., 1/20 | V Wrestling | New Milford Invitational | Away | 10:00 a.m. | ||
| Tue., 1/23 | V Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 69-78 | |
| Tue., 1/23 | JV Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/23 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Woodland HS Pool [Directions] | 5:00 p.m. | ||
| Tue., 1/23 | V Wrestling | Branford | Away - James L MacVeigh Alumni Athletic Complex - Gym [Directions] | 6:30 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Wolcott | Away - Wolcott HS [Directions] | 7:00 p.m. | L 48-56 | |
| Tue., 1/23 | JV Girls Basketball | Wolcott | Away - Wolcott HS [Directions] | 5:15 p.m. | ||
| Wed., 1/24 | FR Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 6:30 p.m. | ||
| Wed., 1/24 | V Girls Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 41-52 | |
| Wed., 1/24 | JV Girls Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/25 | V Boys Indoor Track | Glastonbury Developmental | Away - Glastonbury HS | 4:00 p.m. | two buses | |
| Fri., 1/26 | V Boys Basketball | Kennedy | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 63-53 | |
| Fri., 1/26 | JV Boys Basketball | Kennedy | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Kennedy | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Torrington | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 44-54 | |
| Fri., 1/26 | JV Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Sat., 1/27 | V Wrestling | Ridgefield Challenge | Away | 10:00 a.m. | ||
| Mon., 1/29 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 45-104 | |
| Mon., 1/29 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Mon., 1/29 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Mon., 1/29 | V Boys Indoor Track | NVL Championships | Away - New Haven Field House | 4:30 p.m. | ||
| Mon., 1/29 | V Girls Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 45-62 | |
| Mon., 1/29 | JV Girls Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Wrestling | Notre Dame-West Haven | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Fri., 2/2 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | W 53-50 | |
| Fri., 2/2 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 3:45 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Holy Cross | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | V Girls Basketball | Watertown | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 65-56 | |
| Fri., 2/2 | JV Girls Basketball | Watertown | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/3 | V Wrestling | Foran Duals | Away | 9:00 a.m. | ||
| Tue., 2/6 | V Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 47-41 | |
| Tue., 2/6 | JV Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 23-51 | |
| Tue., 2/6 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | ||
| Thu., 2/8 | V Wrestling | Jonathan Law | Away - Jonathan Law HS Old Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | L 60-64 | |
| Fri., 2/9 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 3:30 p.m. | ||
| Fri., 2/9 | JV Wrestling | SCC JV Tournament | Away - Fairfield Prep | 4:00 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 51-65 | |
| Fri., 2/9 | JV Girls Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 2/10 | V Wrestling | SCC Championships | Away - Fairfield Prep - University location | 9:00 a.m. | Drop off and return for pick up at 6:00 pm | |
| Mon., 2/12 | V Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 40-70 | |
| Mon., 2/12 | JV Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | W 36-23 | |
| Mon., 2/12 | JV Girls Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Tue., 2/13 | V Boys Swimming and Diving | Naugatuck | Home - Woodland HS Pool [Directions] | 5:00 p.m. | ||
| Wed., 2/14 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 72-79 | |
| Wed., 2/14 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Seymour | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 2/14 | V Girls Basketball | Seymour | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 65-31 | |
| Wed., 2/14 | JV Girls Basketball | Seymour | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 4:45 p.m. | Drop off & pick up at 9:00 pm | |
| Sat., 2/17 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/17 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 9:00 a.m. | Drop off & pick up at 5:00 pm | |
| Tue., 2/20 | V Boys Basketball | Derby | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 63-62 | |
| Tue., 2/20 | JV Boys Basketball | Derby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/23 | V Boys Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 52-63 | |
| Fri., 2/23 | JV Boys Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:00 p.m. | Drop off only | |
| Sat., 2/24 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | Drop off only | |
| Tue., 2/27 | V Boys Swimming and Diving | NVL Swim Trials | Away - Kennedy HS | 4:00 p.m. | ||
| Wed., 2/28 | V Boys Swimming and Diving | NVL Diving Championships | Away - Kennedy HS | 6:00 p.m. | ||
| Thu., 3/1 | V Boys Swimming and Diving | NVL Championships | Away - Kennedy HS | 4:30 p.m. | ||
| Fri., 3/2 | V Wrestling | New England Tournament | Away - Providence, RI | 4:00 p.m. | ||
| Sat., 3/3 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/3 | V Wrestling | New England Tournament | Away - Providence, RI | 9:00 a.m. | ||
| Tue., 3/27 | V Baseball | East Hartford (Scrim.) | Home - CT Sportsplex [Directions] | TBA | 5-8pm | |
| Wed., 3/28 | V Baseball | Stratford (Scrim.) | Away - Penders Field [Directions] | 3:30 p.m. | ||
| Thu., 3/29 | V Boys Tennis | Farmington (Scrim.) | Away - Farmington HS [Directions] | 3:45 p.m. | ||
| Thu., 3/29 | V Softball | WCA (Scrim.) | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Sat., 3/31 | V Baseball | Wolcott | Home - Woodland HS Baseball Field [Directions] | 1:00 p.m. | L 3-5 | |
| Sat., 3/31 | V Softball | Wolcott Tech (Scrim.) | Home - Woodland Softball Field [Directions] | 9:00 a.m. | ||
| Thu., 4/5 | V Boys Outdoor Track | Torrington, Naugatuck | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Thu., 4/5 | V Boys Tennis | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | L 2-7 | |
| Thu., 4/5 | V Girls Outdoor Track | Torrington, Naugatuck | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Thu., 4/5 | V Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | 3:45 p.m. | W 7-2 | |
| Thu., 4/5 | V Girls Tennis | St. Paul Catholic | Away - Page Park, Bristol [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 4/6 | FR Baseball | Kennedy | Away - Bucks Hill Park [Directions] | Cancelled | Cancelled | |
| Sat., 4/7 | V Baseball | Ansonia | Home - Woodland HS Baseball Field [Directions] | 2:30 p.m. | W 13-7 | |
| Sat., 4/7 | V Boys Outdoor Track | BellRinger | Away - East Hampton HS | TBA | ||
| Sat., 4/7 | V Softball | Brookfield | Home - Woodland Softball Field [Directions] | 12:00 p.m. | L 0-5 | |
| Mon., 4/9 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 1-6 | |
| Mon., 4/9 | FR Baseball | St. Paul Catholic | Away - Page Park, Bristol [Directions] | 3:45 p.m. | ||
| Mon., 4/9 | V Boys Tennis | Sacred Heart | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 9-0 | |
| Mon., 4/9 | V Softball | St. Paul Catholic | Home - Woodland Softball Field [Directions] | 4:00 p.m. | L 3-13 | |
| Mon., 4/9 | V Girls Tennis | Sacred Heart | Away - Fulton Park | 3:45 p.m. | L 2-5 | |
| Tue., 4/10 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | W 9-0 | |
| Wed., 4/11 | V Baseball | Watertown | Away - Deland Field [Directions] | 3:45 p.m. | W 6-2 | |
| Wed., 4/11 | V Boys Golf | Holy Cross | Away - W Hills [Directions] | 2:30 p.m. | Woodland 213 Julian Perino 45 Josh Hassan 48 Chris Guerrette 57 Tom Conroy 63 Holy Cross 181 | |
| Wed., 4/11 | V Boys Outdoor Track | Watertown, Wolcott | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Wed., 4/11 | V Girls Outdoor Track | Watertown, Wolcott | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Wed., 4/11 | V Softball | Watertown | Away - Watertown HS [Directions] | 3:45 p.m. | L 0-2 | |
| Thu., 4/12 | V Baseball | Goodwin Tech | Away - Goodwin Tech HS Field [Directions] | 3:45 p.m. | W 14-2 (5) | |
| Thu., 4/12 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Thu., 4/12 | V Boys Golf | Wilby | Home - Oxford Greens [Directions] | 3:00 p.m. | Woodland-Forfeit Josh Hassan 47 Chris Guerrette 52 Tom Conroy 54 Wilby 238 | |
| Thu., 4/12 | V Boys Tennis | Naugatuck | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 3-6 | |
| Thu., 4/12 | V Softball | Ansonia | Home - Woodland Softball Field [Directions] | 3:30 p.m. | W 10-0 | |
| Fri., 4/13 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 4/13 | V Boys Tennis | Watertown | Away - Crestbrook Park [Directions] | 3:30 p.m. | W 6-3 | |
| Fri., 4/13 | V Softball | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | L 0-15 | |
| Fri., 4/13 | V Girls Tennis | Ansonia | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 7-0 | |
| Sat., 4/14 | V Baseball | Sacred Heart | Home - Woodland HS Baseball Field [Directions] | 12:00 p.m. | W 3-2 | |
| Sat., 4/14 | V Boys Outdoor Track | Seymour, Crosby | Away - Seymour HS Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/14 | V Girls Outdoor Track | Seymour, Crosby | Away - Seymour HS Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/14 | JV Softball | Wolcott | Away - Wolcott HS [Directions] | 12:00 p.m. | ||
| Sat., 4/14 | V Girls Tennis | Wolcott | Home - Woodland HS Tennis courts [Directions] | 11:00 a.m. | W 5-2 | |
| Tue., 4/17 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | 3:45 p.m. | W 12-6 | |
| Tue., 4/17 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | 2:30 p.m. | Woodland 188 Julian Perino 39 Josh Hassan 44 Chris Guerrette 52 Tom Conroy 53 Sacred Heart 194 | |
| Tue., 4/17 | V Boys Tennis | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 11:00 a.m. | W 9-0 | |
| Tue., 4/17 | V Girls Tennis | Kennedy | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 7-0 | |
| Wed., 4/18 | V Baseball | Oxford | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 4-3 (8) | |
| Wed., 4/18 | V Boys Tennis | Torrington | Home - Woodland HS Tennis courts [Directions] | 11:00 a.m. | L 2-7 | |
| Wed., 4/18 | V Softball | Oxford | Away - OHS Softball Field [Directions] | 3:45 p.m. | L 2-17 | |
| Wed., 4/18 | V Girls Tennis | Torrington | Away - Torrington HS [Directions] | 3:30 p.m. | W 5-2 | |
| Fri., 4/20 | V Baseball | East Granby | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | W 6-2 | |
| Fri., 4/20 | V Softball | Seymour | Home - Woodland Softball Field [Directions] | 3:30 p.m. | L 1-13 | |
| Fri., 4/20 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 4/21 | V Softball | Torrington | Home - Woodland Softball Field [Directions] | 11:00 a.m. | W 6-7 | |
| Mon., 4/23 | V Baseball | Crosby | Away - Crosby HS [Directions] | 3:45 p.m. | W 19-0 (5) | |
| Mon., 4/23 | FR Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/23 | V Softball | Crosby | Home - Woodland Softball Field [Directions] | 4:00 p.m. | W 16-1 | |
| Tue., 4/24 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | 3:00 p.m. | Woodland 200 Julian Perino 42 Josh Hassan 46 Chris Guerrette 57 Tom Conroy 55 Watertown 224 | |
| Tue., 4/24 | V Boys Outdoor Track | WCA, Derby | Home - Woodland HS Track [Directions] | 3:30 p.m. | and Kaynor Tech | |
| Tue., 4/24 | V Boys Tennis | Wolcott | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | L 2-7 | |
| Tue., 4/24 | V Girls Outdoor Track | WCA, Derby | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 4/24 | V Girls Tennis | Seymour | Away - Seymour HS [Directions] | 3:30 p.m. | W 6-1 | |
| Thu., 4/26 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | ||
| Thu., 4/26 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | 3:00 p.m. | Woodland 200 Julian Perino 45 Josh Hassan 55 Chris Guerrette 50 Tom Conroy 50 Wolcott 227 | |
| Thu., 4/26 | V Boys Tennis | Crosby | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 9-0 | |
| Thu., 4/26 | V Boys Tennis | Crosby | Home - Woodland HS [Directions] | 5:00 p.m. | W 6-0 | |
| Thu., 4/26 | JV Softball | Naugatuck | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Thu., 4/26 | V Girls Tennis | Crosby | Away - Crosby HS [Directions] | 3:30 p.m. | W 7-0 | |
| Fri., 4/27 | V Boys Golf | Kaynor Tech | Away - East Mountain Golf Course [Directions] | 2:00 p.m. | Woodland 171 Julian Perino 34 Josh Hassan 39 Chris Guerrette 48 Tom Conroy 50 | |
| Sat., 4/28 | V Baseball | WCA | Away - Washington Park [Directions] | 3:30 p.m. | W 7-0 | |
| Mon., 4/30 | V Baseball | Wilby | Away - Wilby H.S. [Directions] | 3:45 p.m. | W 21-0 (5) | |
| Mon., 4/30 | V Boys Golf | Naugatuck | Away - Hop Brook [Directions] | 2:30 p.m. | Woodland -Forfeit Julian Perino 46 Chris Guerrette 45 Alec Robinson 69 | |
| Mon., 4/30 | V Boys Tennis | Holy Cross | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 4-5 | |
| Mon., 4/30 | V Softball | Wilby | Away - Bucks Hill Park [Directions] | 3:45 p.m. | W 18-1 | |
| Tue., 5/1 | V Baseball | Naugatuck | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 4-1 | |
| Tue., 5/1 | JV Baseball | Wilby | Away - Wilby H.S. [Directions] | 3:45 p.m. | ||
| Tue., 5/1 | V Boys Outdoor Track | Sacred Heart, Kennedy | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/1 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | W 6-3 | |
| Tue., 5/1 | V Girls Outdoor Track | Sacred Heart, Kennedy | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/1 | V Softball | Naugatuck | Home - Woodland Softball Field [Directions] | 4:00 p.m. | L 1-5 | |
| Tue., 5/1 | V Girls Tennis | Naugatuck | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 3-4 | |
| Wed., 5/2 | V Baseball | Kennedy | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 10-0 | |
| Wed., 5/2 | FR Baseball | Kennedy | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | Cancelled | |
| Wed., 5/2 | V Boys Golf | Seymour | Away - Oxford Greens [Directions] | 3:00 p.m. | Woodland 181 Julian Perino 37 Josh Hassan 42 Chris Guerrette 50 Tom Conroy 52 Seymour 201 | |
| Wed., 5/2 | V Boys Tennis | Torrington | Away - Torrington HS [Directions] | 3:30 p.m. | L 4-5 | |
| Wed., 5/2 | V Softball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | W 8-2 | |
| Thu., 5/3 | JV Baseball | Kennedy | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 5/3 | V Boys Golf | Woodland Invitational | Home - Oxford Greens [Directions] | TBA | Woodland 193 Julian Perino 40 front Josh Hassan 48 front Tom Conroy 52 Chris Guerrete 53 | |
| Thu., 5/3 | JV Softball | Kennedy | Away - Town Plot Park [Directions] | 3:30 p.m. | ||
| Fri., 5/4 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | L 3-7 | |
| Fri., 5/4 | FR Baseball | Wolcott | Away - BAW [Directions] | 3:45 p.m. | ||
| Fri., 5/4 | V Softball | Wolcott | Home - Woodland Softball Field [Directions] | 3:45 p.m. | L 0-18 | |
| Fri., 5/4 | V Girls Tennis | Seymour | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 4-3 | |
| Sat., 5/5 | JV Baseball | Wolcott | Away - Wolcott HS [Directions] | 11:00 a.m. | ||
| Mon., 5/7 | V Baseball | Watertown | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | L 2-4 | |
| Mon., 5/7 | FR Baseball | St. Paul Catholic | Home - Beacon Falls Rec - Pent Field [Directions] | 3:45 p.m. | ||
| Mon., 5/7 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | 3:00 p.m. | Woodland 198 Julian Perino 45 Josh Hassan 44 Chris Guerrette 53 Tom Conroy 56 Torrington 168 | |
| Mon., 5/7 | V Boys Tennis | Kennedy | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 9-0 | |
| Mon., 5/7 | V Softball | Watertown | Home - Woodland Softball Field [Directions] | 3:30 p.m. | L 4-13 | |
| Mon., 5/7 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | W 7-0 | |
| Tue., 5/8 | JV Baseball | Watertown | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/8 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 3:00 p.m. | Woodland- Forfeit Julian Perino 42 Josh Hassan 40 Tom Conroy 59 Holy Cross | |
| Tue., 5/8 | V Boys Outdoor Track | Holy Cross, Oxford | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/8 | V Girls Outdoor Track | Holy Cross, Oxford | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/8 | V Girls Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | W 4-3 | |
| Wed., 5/9 | V Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 6:30 p.m. | W 5-2 | |
| Wed., 5/9 | FR Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | ||
| Wed., 5/9 | V Boys Golf | Stigberg | Away - Farmingbury Hills | 9:00 a.m. | Julian Perino Josh Hassan 70 | |
| Wed., 5/9 | V Boys Tennis | Watertown | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 8-1 | |
| Wed., 5/9 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 5/9 | JV Softball | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | ||
| Wed., 5/9 | V Girls Tennis | Watertown | Away - Crestbrook Park [Directions] | 3:30 p.m. | W 4-3 | |
| Thu., 5/10 | V Girls Tennis | Wilby | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 4-0 | Senior Night |
| Fri., 5/11 | V Baseball | Derby | Away - Naugatuck HS [Directions] | 6:30 p.m. | L 3-4 | |
| Fri., 5/11 | JV Baseball | Naugatuck | Away - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Fri., 5/11 | FR Baseball | Kennedy | Home - Woodland HS Baseball Field [Directions] | Cancelled | Cancelled | |
| Fri., 5/11 | V Softball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 4:00 p.m. | W 19-3 | |
| Mon., 5/14 | V Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | W 9-2 | Senior Night |
| Mon., 5/14 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Mon., 5/14 | V Boys Golf | St. Paul Catholic | Away - Chippanee Golf Club [Directions] | 3:00 p.m. | Julian Perino 45 Woodland 190 Jash Hassan 48 Chris Guerrette 49 Tom Conroy 48 St. Paul 186 | |
| Mon., 5/14 | V Softball | Torrington | Away - Torrington HS [Directions] | 4:00 p.m. | W 5-4 | |
| Thu., 5/17 | V Boys Golf | Waterbury Coop, Sacred Heart | Away - East Mountain Golf Course [Directions] | 2:30 p.m. | Woodland 184 Sacred Heart 174 Julian Perino 42 Josh Hassan 40 Chris Guerrette 49 Tom Conroy 53 | |
| Thu., 5/17 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | 3:00 p.m. | ||
| Thu., 5/17 | V Boys Outdoor Track | Wilby, St. Paul Catholic, O'Brien Tech, Platt Tech | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Thu., 5/17 | V Girls Outdoor Track | Wilby, St. Paul Catholic, Platt Tech | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Fri., 5/18 | V Baseball | Seymour | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 10-8 | |
| Fri., 5/18 | V Softball | Holy Cross | Home - Woodland Softball Field [Directions] | 3:00 p.m. | L 1-14 | |
| Fri., 5/18 | JV Softball | Holy Cross | Home - Woodland Softball Field [Directions] | 5:00 p.m. | ||
| Sat., 5/19 | V Softball | Thomaston (Scrim.) | Home - Woodland Softball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/19 | V Softball | NVL 1/4 finals | Home - Woodland Softball Field [Directions] | Cancelled | Cancelled | |
| Sat., 5/19 | JV Softball | NVL 1/4 finals | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | Cancelled | |
| Mon., 5/21 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | 3:00 p.m. | Sacred Heart 185 - Woodland Regional 189 Sacred Heart: Jack Vaillancourt 38 (co-medalist), Shea Zaccagnini 40, Matt Arias 49, Veronica Diaz 58 Woodland Regional: Josh Hassan 41, Julian Perino 38 (co-medalist), Chris Guerrette 51, Tom Conroy 59 | Sacred Heart only |
| Mon., 5/21 | V Softball | NVL Semi-Finals | Away | Cancelled | Cancelled | |
| Mon., 5/21 | JV Softball | NVL Semi-Finals | Away | Cancelled | Cancelled | |
| Tue., 5/22 | V Boys Outdoor Track | NVL Track Tournament | Away - Seymour HS | 1:30 p.m. | field starts 1:30/ track starts at 3:30 | |
| Tue., 5/22 | JV Softball | Wolcott | Home - Woodland Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/23 | V Baseball | Seymour | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/23 | V Boys Outdoor Track | JV NVL Tournament | Away - Torrington | 3:30 p.m. | ||
| Wed., 5/23 | V Softball | Morgan | Home - Woodland Softball Field [Directions] | 3:45 p.m. | W 14-4 | |
| Wed., 5/23 | V Softball | NVL Tournament Finals | Away | Cancelled | Cancelled | |
| Wed., 5/23 | JV Softball | NVL Tournament Finals | Away | Cancelled | Cancelled | |
| Thu., 5/24 | V Baseball | NVL Tournament Semi Finals | Away | TBA | ||
| Thu., 5/24 | V Softball | WCA (Scrim.) | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Fri., 5/25 | V Baseball | NVL Tournament Championships | Away | TBA | ||
| Sat., 5/26 | V Girls Tennis | Granby Memorial | Away - Granby Memorial HS [Directions] | 12:30 p.m. | ||
| Tue., 5/29 | V Baseball | Stonington | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/29 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/29 | V Softball | North Branford | Away - North Branford [Directions] | 4:00 p.m. | L 0-6 | |
| Tue., 5/29 | V Softball | First Round State Tournament | Home - Woodland Softball Field [Directions] | TBA | ||
| Tue., 5/29 | JV Softball | First Round State Tournament | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | Cancelled | |
| Wed., 5/30 | V Baseball | Lewis Mills | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Mon., 6/4 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Sat., 6/9 | V Boys Outdoor Track | New England Championship | Away - Univ. of New Hampshire [Directions] | TBA | ||
| Tue., 6/12 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/13 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||