| Woodland 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 609 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Derby | Home - Woodland HS Baseball Field [Directions] | 10:00 a.m. | ||
| TBA | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Wolcott | Away - Wolcott HS [Directions] | TBA | ||
| TBA | JV Baseball | Holy Cross | Home - Beacon Falls Rec - Pent Field [Directions] | TBA | ||
| TBA | JV Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Seymour | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | FR Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | FR Baseball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | FR Baseball | St. Paul Catholic | Away - Page Park, Bristol [Directions] | TBA | separate bus | |
| TBA | FR Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| TBA | FR Boys Basketball | Wamogo | Home - Woodland HS Gym [Directions] | TBA | ||
| TBA | FM Football | Holy Cross | Away - Holy Cross HS [Directions] | TBA | ||
| TBA | FM Football | Seymour | Away - Seymour HS Turf Field [Directions] | TBA | ||
| TBA | V Boys Soccer | Wilcox Tech (Scrim.) | Home - Woodland Soccer Field [Directions] | Cancelled | Cancelled | |
| TBA | JV Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | ||
| TBA | JV Boys Soccer | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Boys Soccer | Kennedy | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Boys Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | TBA | ||
| TBA | JV Girls Basketball | Wilby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| TBA | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | TBA | ||
| TBA | FR Girls Basketball | Pomperaug | Home - Woodland Gym [Directions] | TBA | ||
| TBA | FR Girls Basketball | Kennedy | Home - Woodland HS Gym [Directions] | TBA | ||
| TBA | FR Girls Basketball | Seymour | Away - Seymour HS [Directions] | TBA | ||
| TBA | V Girls Soccer | Cheshire (Scrim.) | Away - Cheshire HS soccer field [Directions] | 5:00 p.m. | ||
| TBA | JV Girls Soccer | Sacred Heart | Away - Bucks Hill (Montoe) Park | 3:45 p.m. | ||
| TBA | JV Softball | Seymour | Away - Seymour HS [Directions] | 3:30 p.m. | ||
| TBA | JV Softball | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Softball | Oxford | Away - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Kennedy | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| Sat., 8/25 | V Football | Hopkins School (Scrim.) | Away | 9:00 a.m. | ||
| Thu., 8/30 | V Football | Plainville (Scrim.) | Away [Directions] | 6:00 p.m. | ||
| Thu., 8/30 | V Boys Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 8/30 | V Girls Soccer | Lewis Mills (Scrim.) | Away - Lewis Mills HS [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | V Girls Volleyball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 3:45 p.m. | ||
| Fri., 8/31 | V Girls Volleyball | Fairfield Warde (Scrim.) | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Sat., 9/1 | V Boys Cross Country | WEst Haven Beach Run | Away | TBA | ||
| Sat., 9/1 | V Girls Cross Country | West Haven Beach Run | Away | TBA | ||
| Sat., 9/1 | V Girls Volleyball | EAst Haven Jamboree | Away | TBA | ||
| Mon., 9/3 | V Girls Volleyball | Labor Day Jamboree | Away - CT Sports Center, Woodbridge CT | TBA | ||
| Wed., 9/5 | V Girls Soccer | Nonnewaug (Scrim.) | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/7 | V Football | Torrington | Away - Torrington HS [Directions] | 6:30 p.m. | W 35-0 | |
| Fri., 9/7 | V Boys Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/7 | V Girls Soccer | Sacred Heart | Away - Bucks Hill (Montoe) Park | 3:45 p.m. | W 9-0 | |
| Sat., 9/8 | V Boys Soccer | Brookfield | Home - Woodland Soccer Field [Directions] | 1:00 p.m. | T 2-2 | |
| Sat., 9/8 | V Girls Soccer | Brookfield | Home - Woodland Soccer Field [Directions] | 11:00 a.m. | T 3-3 | |
| Sat., 9/8 | V Girls Volleyball | Blast at the Beach | Away | TBA | ||
| Sat., 9/8 | JV Girls Volleyball | Blast at the Beach | Away | TBA | ||
| Mon., 9/10 | V Girls Volleyball | Oxford | Home - Woodland HS Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Mon., 9/10 | JV Girls Volleyball | Oxford | Home - Woodland HS Gym [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 9/11 | V Boys Cross Country | Wilby, Wolcott | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 9/11 | V Boys Soccer | WCA | Away - Municipal Stadium [Directions] | 6:30 p.m. | W 4-0 | |
| Tue., 9/11 | V Girls Cross Country | Wilby, Wolcott | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 9/11 | V Girls Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 4:00 p.m. | W 8-1 | |
| Tue., 9/11 | V Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Tue., 9/11 | JV Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | W 2-1 | |
| Wed., 9/12 | FM Football | Wilby | Away - Wilby H.S. [Directions] | 3:45 p.m. | ||
| Wed., 9/12 | JV Girls Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Girls Swimming and Diving | Waterford | Home - Woodland Pool [Directions] | 4:30 p.m. | Win 100-82 | |
| Thu., 9/13 | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | 3:30 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Wolcott | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/13 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | W 3-1 | |
| Thu., 9/13 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 9/14 | V Football | Wilby | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 49-0 | |
| Fri., 9/14 | V Boys Soccer | Crosby | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 3-0 | |
| Fri., 9/14 | JV Girls Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 9/14 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:00 p.m. | Win 101-85 | |
| Fri., 9/14 | V Girls Volleyball | Kennedy | Home - Woodland HS Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 9/14 | JV Girls Volleyball | Kennedy | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 9/15 | V Boys Cross Country | Wilton Invitational | Away - Wilton HS | TBA | ||
| Sat., 9/15 | JV Boys Soccer | Crosby | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 9/17 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | W 10-0 | |
| Tue., 9/18 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland Pool [Directions] | 4:30 p.m. | Win 97-80 | |
| Tue., 9/18 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/18 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 9/19 | V Boys Cross Country | Naugatuck, Seymour, WCA | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 9/19 | JV Boys Soccer | Sacred Heart | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 9/19 | V Girls Cross Country | Naugatuck, Seymour, WCA | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 9/19 | V Girls Soccer | Holy Cross | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 9/20 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | T 1-1 | |
| Thu., 9/20 | JV Girls Soccer | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 9/21 | V Football | Derby | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 35-14 | |
| Fri., 9/21 | JV Boys Soccer | Naugatuck | Away - Breen SS (JV & Fr.) [Directions] | 3:45 p.m. | ||
| Fri., 9/21 | V Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | T 1-1 | |
| Fri., 9/21 | V Girls Swimming and Diving | Seymour | Away - Seymour HS [Directions] | 4:00 p.m. | Loss 74-92 | |
| Fri., 9/21 | V Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/21 | JV Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 9/22 | FM Football | Derby | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/22 | JV Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 9/24 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | W 2-0 | |
| Tue., 9/25 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | Loss 86-94 | |
| Tue., 9/25 | V Girls Volleyball | Seymour | Home - Woodland HS Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 9/25 | JV Girls Volleyball | Seymour | Home - Woodland HS Gym [Directions] | 4:45 p.m. | L 0-2 | |
| Thu., 9/27 | V Boys Cross Country | Holy Cross, Watertown, St. Paul Catholic | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Thu., 9/27 | V Girls Cross Country | Holy Cross, Watertown, St. Paul Catholic | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Thu., 9/27 | V Girls Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 9/27 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:15 p.m. | W 3-1 | |
| Thu., 9/27 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 9/28 | V Football | Wolcott | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 41-14 | |
| Fri., 9/28 | V Girls Swimming and Diving | Torrington | Home - Woodland Pool [Directions] | 4:00 p.m. | Win 97-81 | |
| Fri., 9/28 | V Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/28 | JV Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 9/29 | V Boys Soccer | Amity | Home - Woodland Soccer Field [Directions] | 9:00 a.m. | L 3-1 | |
| Sat., 9/29 | JV Boys Soccer | Amity | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 10/1 | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Boys Cross Country | Derby, Sacred Heart, Kennedy | Away - Derby H.S. [Directions] | 3:45 p.m. | Home meet for Woodland | |
| Tue., 10/2 | V Boys Soccer | Wolcott | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/2 | V Girls Cross Country | Derby, Sacred Heart, Kennedy | Away - Derby HS [Directions] | 3:30 p.m. | ||
| Tue., 10/2 | V Girls Swimming and Diving | Oxford | Away - OHS Pool [Directions] | 4:00 p.m. | win 87-79 | |
| Tue., 10/2 | V Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/2 | JV Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/3 | JV Girls Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 3:45 p.m. | ||
| Thu., 10/4 | V Boys Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 10/5 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | W 23-22 | |
| Fri., 10/5 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | L 1-2 | |
| Fri., 10/5 | V Girls Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | T 0-0 | |
| Fri., 10/5 | V Girls Swimming and Diving | Sacred Heart | Home - Woodland Pool [Directions] | 4:00 p.m. | Win 93-88 | |
| Fri., 10/5 | V Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/5 | JV Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | W 2-0 | |
| Sat., 10/6 | FM Football | St. Paul Catholic | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/6 | JV Boys Soccer | Watertown | Away - Swift MS [Directions] | 10:30 a.m. | ||
| Mon., 10/8 | JV Girls Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Tue., 10/9 | V Boys Cross Country | Crosby, Oxford, Torrington | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/9 | V Boys Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | W 8-0 | |
| Tue., 10/9 | V Girls Cross Country | Crosby, Oxford, Torrington | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/9 | V Girls Swimming and Diving | Jonathan Law | Home - Woodland HS Pool [Directions] | 4:00 p.m. | Loss 81-96 | |
| Tue., 10/9 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/9 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 10/10 | JV Boys Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | 3:45 p.m. | ||
| Thu., 10/11 | FR Boys Soccer | Naugatuck | Away - Breen SS (JV & Fr.) [Directions] | 3:30 p.m. | ||
| Thu., 10/11 | V Girls Volleyball | WCA | Home - Woodland HS Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 10/11 | JV Girls Volleyball | WCA | Home - Woodland HS Gym [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/12 | V Boys Soccer | Torrington | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 10/12 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | 6:30 p.m. | W 6-0 | |
| Fri., 10/12 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | 4:00 p.m. | Win 86-72 | |
| Fri., 10/12 | V Girls Volleyball | Holy Cross | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/12 | JV Girls Volleyball | Holy Cross | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/13 | JV Boys Soccer | Torrington | Away - Torrington HS [Directions] | 10:00 a.m. | ||
| Sat., 10/13 | V Girls Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 12:00 p.m. | L 0-1 | |
| Mon., 10/15 | V Boys Soccer | Kennedy | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 3-0 | |
| Mon., 10/15 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | W 4-0 | |
| Tue., 10/16 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 10/16 | V Girls Swimming and Diving | Kennedy | Home - Woodland Pool [Directions] | 5:00 p.m. | Win 82-57 | senior night |
| Tue., 10/16 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/16 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/17 | V Boys Cross Country | NVL Championships | Away | TBA | ||
| Wed., 10/17 | V Girls Cross Country | NVL Championships | Away | TBA | ||
| Thu., 10/18 | V Football | Sacred Heart | Away - Municipal Stadium | 6:00 p.m. | W 42-12 | |
| Thu., 10/18 | FR Boys Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 10/18 | JV Girls Soccer | Watertown | Away - Veteran's Park #1 [Directions] | 3:30 p.m. | ||
| Thu., 10/18 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 10/18 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 4:45 p.m. | L 1-2 | |
| Fri., 10/19 | V Boys Soccer | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/19 | V Girls Soccer | Oxford | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | L 2-3 | |
| Fri., 10/19 | V Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 10/19 | JV Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-1 | |
| Sat., 10/20 | FM Football | Sacred Heart | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | JV Boys Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | JV Girls Soccer | Oxford | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 10/22 | V Boys Cross Country | Platt Tech Invitational | Away - Eisenhower park | 3:00 p.m. | ||
| Mon., 10/22 | V Boys Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/22 | V Girls Soccer | Derby | Home - Woodland Soccer Field [Directions] | 6:00 p.m. | W 9-0 | |
| Mon., 10/22 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/22 | JV Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 4:45 p.m. | L 0-2 | |
| Wed., 10/24 | V Boys Soccer | Derby | Home - Woodland Soccer Field [Directions] | 6:00 p.m. | W 6-0 | |
| Wed., 10/24 | JV Boys Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/24 | V Girls Soccer | Pomperaug | Away - Sports Complex & Track [Directions] | 7:00 p.m. | L 0-4 | |
| Wed., 10/24 | JV Girls Soccer | Pomperaug | Away - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Wed., 10/24 | V Girls Volleyball | East Haven | Home - East Haven HS [Directions] | 6:00 p.m. | L 2-3 | |
| Wed., 10/24 | JV Girls Volleyball | East Haven | Home - Woodland HS [Directions] | 4:45 p.m. | W 2-0 | |
| Thu., 10/25 | JV Boys Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 10/26 | V Boys Cross Country | Class Championships | Away | TBA | ||
| Fri., 10/26 | V Football | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 7:00 p.m. | W 40-0 | |
| Fri., 10/26 | V Girls Cross Country | Class Championships | Away | TBA | ||
| Sat., 10/27 | V Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 11:00 a.m. | NVL Quarter Finals | |
| Mon., 10/29 | FM Football | Torrington | Home - Woodland Football Field [Directions] | 5:30 p.m. | ||
| Mon., 10/29 | V Boys Soccer | Seymour | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 2-1 (5-3 PKs) | NVL Quarter Finals |
| Mon., 10/29 | V Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | W 2-1 | NVL Quarter-finals |
| Mon., 10/29 | V Girls Volleyball | Kennedy | Away - seymour middle school [Directions] | 5:00 p.m. | NVL Semi-final tournament game | |
| Tue., 10/30 | V Boys Soccer | Naugatuck | Away - Crosby HS [Directions] | 5:00 p.m. | W 2-0 | |
| Tue., 10/30 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-2 | |
| Tue., 10/30 | V Girls Swimming and Diving | NVL Swim Trials | Away - Kennedy HS | 4:30 p.m. | ||
| Thu., 11/1 | V Boys Soccer | Watertown | Away - Naugatuck HS [Directions] | 5:00 p.m. | ||
| Thu., 11/1 | V Girls Soccer | NVL Championships | Away - Naugatuck HS | TBA | to start 30 mins after boys final | |
| Thu., 11/1 | V Girls Swimming and Diving | NVL Diving Championships | Away - TBA | 6:00 p.m. | ||
| Thu., 11/1 | V Girls Volleyball | NVl Championships | Away - Kennedy HS | 7:00 p.m. | ||
| Fri., 11/2 | V Boys Cross Country | State Open Championships | Away | TBA | ||
| Fri., 11/2 | V Football | Ansonia | Home - Woodland Football Field [Directions] | 5:30 p.m. | L 20-36 | |
| Fri., 11/2 | V Girls Cross Country | State Open Championships | Away | TBA | ||
| Fri., 11/2 | V Girls Swimming and Diving | NVL Swim Championships | Away - Kennedy HS | 4:30 p.m. | ||
| Sat., 11/3 | V Boys Soccer | CIAC Tourney Qualifying Round | Away - Site TBA | TBA | ||
| Sat., 11/3 | V Girls Soccer | CIAC Tourney Qualifying Round | Away - Site TBA | TBA | ||
| Mon., 11/5 | V Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 2:00 p.m. | ||
| Mon., 11/5 | V Girls Volleyball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 6:00 p.m. | ||
| Mon., 11/5 | V Girls Volleyball | Kaynor Tech | Home - Higher Seed [Directions] | TBA | W 3-0 | |
| Wed., 11/7 | V Boys Soccer | Aerospace | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | W 2-1 | |
| Wed., 11/7 | V Girls Soccer | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Wed., 11/7 | V Girls Volleyball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Thu., 11/8 | V Boys Soccer | Windham | Away - WHS Ferrigno Field [Directions] | 5:00 p.m. | ||
| Thu., 11/8 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Bulkeley HS [Directions] | 5:30 p.m. | ||
| Fri., 11/9 | V Girls Soccer | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Fri., 11/9 | V Girls Volleyball | Montville | Home - Woodland HS Gym [Directions] | 6:00 p.m. | ||
| Sat., 11/10 | V Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | W 21-7 | |
| Sat., 11/10 | V Boys Soccer | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Cheshire Community Pool [Directions] | 10:00 p.m. | ||
| Mon., 11/12 | FM Football | Oxford | Home - Woodland Football Field [Directions] | 3:45 p.m. | ||
| Mon., 11/12 | V Girls Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Girls Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Girls Volleyball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Wed., 11/14 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Wed., 11/14 | V Girls Swimming and Diving | CIAC Class S Finals | Away - Wesleyan [Directions] | 7:00 p.m. | ||
| Thu., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/17 | V Boys Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | V Girls Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Sat., 11/17 | V Girls Volleyball | CIAC Tourney Final | Away - East Haven [Directions] | TBA | ||
| Wed., 11/21 | V Football | Seymour | Home - Woodland Football Field [Directions] | 5:30 p.m. | W 14-12 | |
| Sat., 12/1 | V Girls Basketball | Griswold (Scrim.) | Away - GHS Gym [Directions] | 10:00 a.m. | ||
| Wed., 12/5 | V Boys Basketball | Abbott Tech (Scrim.) | Home - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Thu., 12/6 | V Girls Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/8 | V Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/8 | V Girls Basketball | Shepaug Valley (Scrim.) | Away - Ted Alex Gymnasium [Directions] | 3:00 p.m. | ||
| Mon., 12/10 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | W 39-22 | |
| Mon., 12/10 | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:30 p.m. | ||
| Mon., 12/10 | FR Girls Basketball | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | ||
| Tue., 12/11 | V Boys Basketball | Thomaston (Scrim.) | Home - Woodland HS Gym [Directions] | 4:15 p.m. | ||
| Wed., 12/12 | V Wrestling | Cheshire | Away - Cheshire High East Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/13 | FR Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Thu., 12/13 | V Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 25-52 | |
| Thu., 12/13 | JV Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | V Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 59-106 | |
| Fri., 12/14 | JV Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Sat., 12/15 | V Boys Indoor Track | Southern Invite | Away - SCSU | TBA | ||
| Sat., 12/15 | V Wrestling | Shelton Invitational | Away | 10:00 a.m. | ||
| Tue., 12/18 | V Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 70-44 | |
| Tue., 12/18 | JV Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/18 | FR Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/18 | V Boys Swimming and Diving | Oxford | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 12/18 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | L 33-46 | |
| Tue., 12/18 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | V Boys Indoor Track | Glastonbury Developmental | Away - Glastonbury HS | TBA | ||
| Wed., 12/19 | V Wrestling | East Haven | Away - East Haven HS [Directions] | 6:00 p.m. | ||
| Thu., 12/20 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 47-79 | |
| Thu., 12/20 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Thu., 12/20 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | ||
| Thu., 12/20 | V Boys Swimming and Diving | Northwestern | Home - Woodland HS Pool [Directions] | 4:30 p.m. | ||
| Fri., 12/21 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 41-55 | |
| Fri., 12/21 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 12/21 | V Girls Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 35-61 | |
| Fri., 12/21 | JV Girls Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Girls Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/22 | V Boys Indoor Track | Wilton Reindeer Reindeers | Away | 9:30 a.m. | ||
| Sat., 12/22 | V Wrestling | Southington Duals | Away | 10:00 a.m. | ||
| Thu., 12/27 | V Boys Basketball | Oxford | Home - Litchfield HS [Directions] | 6:00 p.m. | L 50-53 | Cowboy Classic Tournament |
| Thu., 12/27 | FR Boys Basketball | Shelton | Home - Woodland HS Gym [Directions] | 12:00 p.m. | ||
| Thu., 12/27 | V Wrestling | New Haven Wrestling | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Sat., 12/29 | V Boys Basketball | Thomaston | Away - Litchfield HS [Directions] | TBA | W 67-54 | |
| Sat., 12/29 | V Boys Indoor Track | Hillouse Relays | Away - Hillhouse | TBA | ||
| Sat., 12/29 | V Wrestling | Trumbull Duals | Away | 9:00 a.m. | ||
| Wed., 1/2 | V Girls Basketball | WCA | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 33-42 | |
| Wed., 1/2 | JV Girls Basketball | WCA | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/3 | V Wrestling | Daniel Hand | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Fri., 1/4 | V Boys Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 55-66 | |
| Fri., 1/4 | JV Boys Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:00 p.m. | ||
| Fri., 1/4 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | W 41-38(OT) | |
| Sat., 1/5 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 2 (Small Gym) [Directions] | 10:00 a.m. | ||
| Sat., 1/5 | V Boys Indoor Track | Elm City Coaches Invite | Away - Hillhouse | TBA | ||
| Sat., 1/5 | V Wrestling | Amity Duals | Home - Paul D. Mengold Gym at Amity HS [Directions] | 9:00 a.m. | Bethel, Morgan, New Haven, Maloney, Joel Barlow | |
| Sat., 1/5 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:00 p.m. | ||
| Mon., 1/7 | FR Girls Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 3:00 p.m. | ||
| Tue., 1/8 | V Boys Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 67-53 | |
| Tue., 1/8 | JV Boys Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/8 | FR Boys Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/8 | V Boys Swimming and Diving | Crosby/WCA | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/8 | V Wrestling | Shelton | Away - Shelton HS Gym [Directions] | 7:00 p.m. | ||
| Tue., 1/8 | V Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | L 35-42 | |
| Thu., 1/10 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | W 62-45 | |
| Thu., 1/10 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | Seymour | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Thu., 1/10 | V Girls Basketball | Seymour | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 40-50 | |
| Thu., 1/10 | JV Girls Basketball | Seymour | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Girls Basketball | Seymour | Home - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/11 | V Boys Swimming and Diving | Kennedy | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/11 | V Wrestling | Fairfield Warde Quad | Away | 4:00 p.m. | ||
| Fri., 1/11 | JV Girls Basketball | Wright Tech | Away - Thomas R. Good Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/11 | FR Girls Basketball | Wright Tech | Away - Thomas R. Good Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/12 | V Boys Indoor Track | Shoreline Coaches invite | Away | TBA | ||
| Sat., 1/12 | V Boys Indoor Track | Glastonbury 9th/10th grade relays | Away - Glastonbury HS | TBA | ||
| Mon., 1/14 | V Boys Indoor Track | Old Saybrook Qualifier | Away - Old Saybrook | TBA | ||
| Mon., 1/14 | V Girls Basketball | Kennedy | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 53-50(OT) | |
| Mon., 1/14 | JV Girls Basketball | Kennedy | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/15 | V Boys Swimming and Diving | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | ||
| Wed., 1/16 | V Boys Basketball | Derby | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 64-71 | |
| Wed., 1/16 | JV Boys Basketball | Derby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/16 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | L 45-48(OT) | |
| Wed., 1/16 | JV Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 1/17 | JV Wrestling | JV only event | Away - Fairfield Warde | 5:00 p.m. | approx. 2 1/2 hours | |
| Fri., 1/18 | V Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 62-75 | |
| Fri., 1/18 | JV Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/18 | FR Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/18 | V Boys Indoor Track | H-K Invitational | Away - TBA | TBA | ||
| Fri., 1/18 | V Boys Swimming and Diving | Sacred Heart | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/18 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 39-36 | |
| Sat., 1/19 | V Wrestling | New Milford Invitational | Away | 10:00 a.m. | ||
| Sat., 1/19 | FR Girls Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 1:00 p.m. | ||
| Wed., 1/23 | V Boys Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 40-77 | |
| Wed., 1/23 | JV Boys Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/23 | FR Boys Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/23 | V Wrestling | Branford | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Wed., 1/23 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | L 25-47 | |
| Wed., 1/23 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Thu., 1/24 | JV Wrestling | Foran | Home - AHS Aux. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 64-66 | |
| Fri., 1/25 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Fri., 1/25 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 38-42(OT) | |
| Fri., 1/25 | JV Girls Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/26 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 1:00 p.m. | L 67-78 | |
| Sat., 1/26 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 11:30 a.m. | ||
| Sat., 1/26 | V Wrestling | Ridgefield Challenge | Away | 10:00 a.m. | ||
| Sat., 1/26 | JV Wrestling | JV event only | Away - Norwalk HS - 23 Calvin Murphy | 9:00 a.m. | until approx. 4:00/5:00 | |
| Sat., 1/26 | FR Girls Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 10:30 a.m. | ||
| Mon., 1/28 | V Boys Indoor Track | NVL Championships | Away | TBA | ||
| Tue., 1/29 | V Wrestling | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | 7:00 p.m. | ||
| Wed., 1/30 | JV Girls Basketball | Bulkeley | Away - Bulkeley HS Field House [Directions] | Cancelled | Cancelled | |
| Fri., 2/1 | V Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 43-63 | |
| Fri., 2/1 | JV Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/1 | FR Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 33-40 | |
| Fri., 2/1 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 4:45 p.m. | ||
| Fri., 2/1 | FR Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | ||
| Sat., 2/2 | FR Boys Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 11:30 p.m. | ||
| Sat., 2/2 | V Wrestling | Foran Duals | Away | 9:00 a.m. | ||
| Sat., 2/2 | V Girls Basketball | Oxford | Home - Woodland HS Gym [Directions] | 3:00 p.m. | L 39-42 | |
| Sat., 2/2 | FR Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 1:00 p.m. | ||
| Mon., 2/4 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | W 72-64 | |
| Mon., 2/4 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 2/4 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | ||
| Tue., 2/5 | V Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | W 64-48 | |
| Tue., 2/5 | JV Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Derby | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 45-24 | |
| Tue., 2/5 | JV Girls Basketball | Derby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Girls Basketball | Holy Cross | Away - HCHS [Directions] | 3:30 p.m. | ||
| Wed., 2/6 | V Wrestling | Jonathan Law | Home - Paul D. Mengold Gym at Amity HS [Directions] | 6:00 p.m. | ||
| Thu., 2/7 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/7 | FR Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 3:45 p.m. | ||
| Fri., 2/8 | V Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 68-58 | |
| Fri., 2/8 | JV Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/8 | V Boys Swimming and Diving | Watertown | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 43-52 | |
| Fri., 2/8 | JV Girls Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | ||
| Sat., 2/9 | V Wrestling | SCC Tournament | Away - Jonathan Law | 9:00 a.m. | ||
| Sat., 2/9 | V Girls Basketball | Bulkeley | Away - Bulkeley HS Field House [Directions] | 12:00 p.m. | W 55-42 | |
| Mon., 2/11 | V Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 71-65(OT) | |
| Mon., 2/11 | JV Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/11 | V Girls Basketball | Wilby | Home - Woodland HS Gym [Directions] | 6:30 p.m. | W 50-18 | |
| Thu., 2/14 | V Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 64-70 | |
| Thu., 2/14 | JV Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/14 | FR Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/14 | V Boys Swimming and Diving | Masuk | Home - Woodland HS Pool [Directions] | 5:00 p.m. | ||
| Fri., 2/15 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Fri., 2/15 | V Wrestling | Class LL Tournament Day 1 | Away - Trumbull HS | 4:45 p.m. | ||
| Fri., 2/15 | V Girls Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 5:00 p.m. | W 53-17 | |
| Fri., 2/15 | JV Girls Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | Class LL Tournament Day 2 | Away - Trumbull HS | 9:00 a.m. | ||
| Sat., 2/16 | V Girls Basketball | NVL Quarter-finals | Away - Holy Cross HS | TBA | ||
| Mon., 2/18 | V Girls Basketball | NVL Semi-Finals | Away - Kennedy HS | TBA | ||
| Wed., 2/20 | V Girls Basketball | NVL Championships | Away - Kennedy HS | 7:00 p.m. | ||
| Fri., 2/22 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:00 p.m. | one way bus only | |
| Fri., 2/22 | V Girls Basketball | Amistad | Away - Amistad [Directions] | 6:00 p.m. | ||
| Sat., 2/23 | V Boys Basketball | NVL Quarter finals | Away - Wilby HS | TBA | ||
| Sat., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Mon., 2/25 | V Boys Basketball | NVL Semi-Finals | Away - Wilby HS | TBA | ||
| Tue., 2/26 | V Boys Swimming and Diving | NVL Trials | Away - Kennedy HS | 4:00 p.m. | ||
| Tue., 2/26 | V Girls Basketball | CIAC Tourney 1st Round | Away - Higher Seed | TBA | ||
| Wed., 2/27 | V Boys Basketball | NVL Championships | Away - Wilby HS | TBA | ||
| Wed., 2/27 | V Boys Swimming and Diving | NVL Diving Championships | Away - Kennedy HS | 6:00 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | NVL Championships | Away - Kennedy HS | 4:30 p.m. | ||
| Fri., 3/1 | V Girls Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Tue., 3/5 | V Boys Basketball | Ellington | Away - Ellington HS [Directions] | 7:00 p.m. | ||
| Wed., 3/6 | V Boys Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Thu., 3/7 | V Girls Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Fri., 3/8 | V Boys Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Cheshire Community Pool [Directions] | 3:00 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | ||
| Mon., 3/11 | V Girls Basketball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Tue., 3/12 | V Boys Basketball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | ||
| Sat., 3/16 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sat., 3/16 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sun., 3/17 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sun., 3/17 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Thu., 3/21 | V Baseball | Branford (Scrim.) | Away - James L. MacVeigh Alumni Athletic Complex - Baseball Field [Directions] | 4:00 p.m. | ||
| Sat., 3/23 | V Baseball | Kolbe Cathedral (Scrim.) | Away - Harding HS [Directions] | 1:00 p.m. | ||
| Mon., 3/25 | V Softball | Trumbull (Scrim.) | Away - THS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Baseball | Pomperaug (Scrim.) | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 3/27 | V Baseball | Stratford (Scrim.) | Away - Penders Field [Directions] | 3:30 p.m. | ||
| Thu., 3/28 | V Baseball | Coginchaug (Scrim.) | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 3/29 | V Baseball | Joel Barlow (Scrim.) | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 3/29 | V Softball | WCA (Scrim.) | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Sat., 3/30 | V Softball | Ansonia | Home - Woodland Softball Field [Directions] | 11:00 a.m. | W 15-0(6) | |
| Mon., 4/1 | V Baseball | Wilbur Cross | Away - Rice Field I [Directions] | 3:45 p.m. | L 1-14 | |
| Mon., 4/1 | V Boys Tennis | Wolcott | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 4/1 | V Girls Tennis | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/2 | V Baseball | Sacred Heart | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | W 6-5 | |
| Tue., 4/2 | V Boys Outdoor Track | Crosby, Oxford | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Girls Outdoor Track | Crosby, Oxford | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Softball | Sacred Heart | Home - Woodland Softball Field [Directions] | 3:45 p.m. | W 19-0 | |
| Wed., 4/3 | JV Baseball | Sacred Heart | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/3 | V Boys Tennis | Sacred Heart | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | W 5-0 | |
| Wed., 4/3 | JV Softball | Sacred Heart | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Wed., 4/3 | V Girls Tennis | Sacred Heart | Away - Fulton Park | 3:45 p.m. | L 3-4 | |
| Thu., 4/4 | FR Baseball | Pomperaug | Away - Community Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 4/4 | V Girls Tennis | Wilby | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | W 7-0 | |
| Sat., 4/6 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | 3:00 p.m. | L 1-3 | |
| Sat., 4/6 | FR Baseball | Wolcott | Away - BAW [Directions] | 1:00 p.m. | separate bus | |
| Sat., 4/6 | V Boys Outdoor Track | Bellringer | Away - EAst Hampton | TBA | ||
| Sat., 4/6 | V Girls Outdoor Track | Bellringer | Away - East Hampton | TBA | ||
| Sat., 4/6 | JV Softball | Naugatuck | Home - Wolcott JV field [Directions] | 1:30 p.m. | ||
| Sat., 4/6 | JV Softball | Wolcott | Away - Naugatuck HS [Directions] | 3:00 p.m. | ||
| A request to make the following change(s) to the above event has been submitted by one of the schools involved, but has not yet been accepted by the other -- Change facility to | ||||||
| Mon., 4/8 | FR Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Softball | Wilby | Away - Bucks Hill Park [Directions] | 3:45 p.m. | W 22-2 | |
| Mon., 4/8 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 4/9 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 3-8 | |
| Tue., 4/9 | JV Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 2:30 p.m. | Woodland 245 Tom Conroy 57 Mark Barbarito 58 Holy Cross 173 | |
| Tue., 4/9 | V Boys Tennis | Kennedy | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 5-0 | |
| Tue., 4/9 | JV Softball | Wilby | Away - Bucks Hill Park [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Baseball | Crosby | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | W 17-0 | |
| Wed., 4/10 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Boys Outdoor Track | WCA, Kennedy | Home - Woodland HS Track [Directions] | 2:45 p.m. | ||
| Wed., 4/10 | V Boys Tennis | Naugatuck | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 2-3 | |
| Wed., 4/10 | V Girls Outdoor Track | WCA, Kennedy | Home - Woodland HS Track [Directions] | 2:45 p.m. | ||
| Wed., 4/10 | V Softball | Crosby | Home - Woodland Softball Field [Directions] | 4:00 p.m. | W 18-0 | |
| Wed., 4/10 | V Girls Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | L 2-5 | |
| Thu., 4/11 | JV Baseball | Crosby | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Boys Golf | Wilby | Away - Western Hills [Directions] | 2:30 p.m. | Woodland 247 Tom Conroy 52 Mark Barbarito 57 Wilby 264 | |
| Thu., 4/11 | JV Softball | Crosby | Home - Woodland Softball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/12 | V Baseball | Derby | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | W 13-3 | |
| Fri., 4/12 | FR Baseball | Brookfield | Away - BHS Baseball Field [Directions] | 3:15 p.m. | ||
| Fri., 4/12 | V Softball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:45 p.m. | W 18-1 | |
| Mon., 4/15 | V Softball | Naugatuck | Away - Disney Wide World of Sports [Directions] | TBA | W 2-1 | |
| Tue., 4/16 | JV Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 11:00 a.m. | ||
| Tue., 4/16 | V Boys Outdoor Track | Watertown, Torrington | Away - John J. Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Tue., 4/16 | V Boys Tennis | Watertown | Away - Crestbrook Park [Directions] | 3:00 p.m. | W 5-0 | |
| Tue., 4/16 | V Girls Outdoor Track | Watertown, Torrington | Away - John J. Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Tue., 4/16 | V Softball | Windsor Locks | Home - Disney World [Directions] | 10:00 a.m. | W 10-0 | |
| Wed., 4/17 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | 3:45 p.m. | W 11-1 | |
| Wed., 4/17 | V Boys Tennis | Torrington | Away - Torrington HS [Directions] | 11:00 a.m. | W 3-2 | |
| Wed., 4/17 | V Softball | Wolcott | Home - Disney World [Directions] | 10:00 a.m. | W 9-2 | |
| Wed., 4/17 | V Girls Tennis | Torrington | Home - Woodland HS Tennis courts [Directions] | 11:00 a.m. | W 8-0 | |
| Thu., 4/18 | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/18 | V Girls Tennis | Seymour | Home - Woodland HS Tennis courts [Directions] | 11:00 a.m. | W 5-2 | |
| Fri., 4/19 | V Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 3:00 p.m. | W 3-2 | |
| Tue., 4/23 | V Boys Outdoor Track | Sacred Heart, Naugatuck | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 4/23 | V Girls Outdoor Track | Sacred Heart, Naugatuck | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | W 4-3 | |
| Wed., 4/24 | V Baseball | Seymour | Away - French Park [Directions] | 3:30 p.m. | W 11-0 | |
| Wed., 4/24 | JV Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Boys Golf | Watertown | Away - Crestbrook Park [Directions] | 2:30 p.m. | Woodland 249 Tom Conroy 53 Mark Barbarito 56 Watertown 193 | |
| Wed., 4/24 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | L 2-3 | |
| Wed., 4/24 | V Softball | Seymour | Home - Beacon Falls Rec - Pent Field [Directions] | 3:30 p.m. | L 1-3 | |
| Wed., 4/24 | V Girls Tennis | Ansonia | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 6-1 | |
| Wed., 4/24 | V Girls Tennis | Ansonia | Home - Woodland HS Tennis courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 4/25 | V Baseball | Ansonia | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | W 10-1 | |
| Thu., 4/25 | JV Baseball | Seymour | Away - French Park [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Watertown | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 5-0 | |
| Thu., 4/25 | V Softball | Torrington | Away - Torrington HS [Directions] | 4:00 p.m. | W 11-3 | |
| Thu., 4/25 | V Girls Tennis | Watertown | Away - Crestbrook Park [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 4/26 | FR Baseball | Kennedy | Away [Directions] | Cancelled | Cancelled | |
| Sat., 4/27 | JV Softball | Watertown | Away - Watertown HS [Directions] | 12:00 p.m. | ||
| Mon., 4/29 | V Baseball | Holy Cross | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | L 10-5 | |
| Mon., 4/29 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | 2:30 p.m. | Woodland 226 Tom Conroy 46 Mark Barbarito 54 Naugatuck 230 | |
| Mon., 4/29 | V Softball | Holy Cross | Home - Woodland Softball Field [Directions] | 3:30 p.m. | L 3-12 | |
| Mon., 4/29 | V Girls Tennis | St. Paul Catholic | Away - Page Park, Bristol [Directions] | 4:30 p.m. | L 1-6 | |
| Tue., 4/30 | V Boys Outdoor Track | Seymour, St. Paul Catholic | Away - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Holy Cross | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 5-0 | |
| Tue., 4/30 | V Girls Outdoor Track | Seymour, St. Paul Catholic | Away - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Softball | Oxford | Away - Oxford [Directions] | 3:45 p.m. | L 4-19 | |
| Wed., 5/1 | FR Baseball | Naugatuck | Home - Pent Field, Beacon Falls [Directions] | 3:30 p.m. | ||
| Wed., 5/1 | V Boys Golf | Seymour | Home - Oxford Greens [Directions] | 2:30 p.m. | Woodland 228 Tom Conroy 42 Mark Barbarito 50 Seymour 200 | |
| Wed., 5/1 | V Boys Tennis | Sacred Heart | Away - Fulton Park | 3:45 p.m. | W 5-0 | |
| Thu., 5/2 | V Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | W 11-2 | |
| Thu., 5/2 | FR Baseball | Xavier | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | 10:45 a.m. | Woodland 246 Tom Conroy 54 Mark Barbarito 59 Sacred Heart 233 | |
| Thu., 5/2 | V Boys Golf | Woodland Invitational | Home - Oxford Greens [Directions] | TBA | ||
| Thu., 5/2 | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 5/3 | JV Baseball | Xavier | Away - Xavier H.S. [Directions] | Cancelled | Cancelled | |
| Mon., 5/6 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | Woodland 236 Tom Conroy 47 Mark Barbarito 53 Torrington 166 | |
| Mon., 5/6 | V Boys Tennis | Torrington | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | W 3-2 | |
| Mon., 5/6 | V Softball | Ansonia | Away - Beacon Falls Rec - Pent Field [Directions] | 3:30 p.m. | W 17-0 | |
| Mon., 5/6 | V Girls Tennis | Seymour | Away - Seymour HS [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/7 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | W 4-0 | |
| Tue., 5/7 | FR Baseball | Wolcott | Away - BAW [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Boys Golf | Wolcott | Away - Farmingbury Country Club [Directions] | 2:30 p.m. | Woodland 223 Tom Conroy 45 Mark Barbarito 58 Wolcott 208 | |
| Tue., 5/7 | V Boys Outdoor Track | Derby, Wilby | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | W 5-0 | |
| Tue., 5/7 | V Girls Outdoor Track | Derby, Wilby | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Softball | Watertown | Away - Watertown HS [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 5/7 | V Girls Tennis | Kennedy | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 6-1 | SENIOR NIGHT |
| Wed., 5/8 | V Baseball | Derby | Away - Naugatuck HS [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/8 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Boys Golf | Stigberg | Away - Farmingbury Hills | 9:30 a.m. | Woodland 223 Tom Conroy 45 Mark Barbarito 58 Wolcott 208 | |
| Wed., 5/8 | V Boys Tennis | Crosby | Away - Crosby HS [Directions] | 3:30 p.m. | W 5-0 | |
| Wed., 5/8 | V Softball | Derby | Home - Woodland Softball Field [Directions] | 3:45 p.m. | W 20-5 | |
| Wed., 5/8 | V Girls Tennis | Crosby | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 5/9 | V Baseball | Watertown | Away - Deland Field [Directions] | 3:45 p.m. | W 9-2 | |
| Thu., 5/9 | V Boys Golf | Waterbury Coop, Wilby | Home - Oxford Greens [Directions] | 3:30 p.m. | Woodland 228 Tom Conroy 48 Mark Barbarito 50 Wilby 265 Kennedy 275 | |
| Thu., 5/9 | JV Softball | Seymour | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Fri., 5/10 | V Baseball | Oxford | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | W 12-1 | |
| Fri., 5/10 | FR Baseball | Pomperaug | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Softball | Oxford | Home - Woodland Softball Field [Directions] | 3:45 p.m. | L 0-9 | |
| Sat., 5/11 | V Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | 10:30 a.m. | W 5-4 | |
| Sat., 5/11 | JV Baseball | Oxford | Home - Woodland HS Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 5/11 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 10:30 a.m. | L 14-17 | |
| Tue., 5/14 | V Baseball | WCA | Away - Waterville Park [Directions] | 6:30 p.m. | W 16-0 | |
| Tue., 5/14 | V Boys Golf | Holy Cross | Away - Western Hills [Directions] | 2:30 p.m. | Woodland 230 Tom Conroy 51 Mark Barbarito 53 Holy Cross 157 | |
| Tue., 5/14 | V Boys Tennis | Holy Cross | Home - Woodland Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 5/14 | V Softball | Kennedy | Home - Woodland Softball Field [Directions] | 5:00 p.m. | W 10-1 | |
| Tue., 5/14 | V Girls Tennis | St. Paul Catholic | Away - Bristol Central [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | JV Baseball | WCA | Away - Washington Park [Directions] | 3:45 p.m. | ||
| Wed., 5/15 | V Boys Tennis | NVL Semi-finals | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | at higher seed (could be 5/16) | |
| Wed., 5/15 | V Softball | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | L 2-5 | |
| Wed., 5/15 | V Girls Tennis | NVL Semi Finals | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | at higher seed (could be 5/16/) | |
| Thu., 5/16 | V Baseball | Xavier | Home - Woodland HS Baseball Field [Directions] | 4:15 p.m. | W 3-2 | |
| Thu., 5/16 | V Boys Golf | Waterbury Coop | Away - Western Hills [Directions] | 2:30 p.m. | Woodland 235 Tom Conroy 48 Mark Barbarito 51 Kennedy 285 | |
| Thu., 5/16 | V Boys Outdoor Track | Platt Tech, O'Brien Tech | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Thu., 5/16 | V Girls Outdoor Track | Platt Tech, O'Brien Tech | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Thu., 5/16 | V Softball | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | W 12-1 | |
| Fri., 5/17 | V Baseball | Seymour | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 8-0 | |
| Fri., 5/17 | FR Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | ||
| Fri., 5/17 | V Boys Tennis | NVL Championships | Away - Wilby HS | 3:00 p.m. | ||
| Fri., 5/17 | V Girls Tennis | NVL Championships | Home - Woodland HS Tennis courts [Directions] | 3:00 p.m. | ||
| Sat., 5/18 | FR Baseball | Torrington | Away - Torrington [Directions] | 12:30 p.m. | ||
| Mon., 5/20 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | 2:30 p.m. | Woodland 216 Tom Conroy 44 Mark Barbarito 49 Sacred Heart 203 | |
| Mon., 5/20 | V Boys Tennis | Individual NVL tournament | Away - Wilby HS | 11:00 a.m. | 11am warm ups/12noon start time | |
| Mon., 5/20 | V Softball | NVL Semi Finals | Away - Seymour HS | TBA | 4:00 or 6:30 start time | |
| Mon., 5/20 | V Girls Tennis | Individual NVL tournament | Home - Woodland HS Tennis courts [Directions] | 11:00 a.m. | warm ups 11/start time 12noon | |
| Tue., 5/21 | V Baseball | Oxford | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | NVL Championships | Away - Torrington HS | 1:30 p.m. | ||
| Tue., 5/21 | V Boys Tennis | Individual NVL Championships | Away - Wilby HS | 12:00 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | NVL Championships | Away - Torrington HS | 1:30 p.m. | ||
| Tue., 5/21 | V Softball | Seymour | Away [Directions] | 6:00 p.m. | ||
| Tue., 5/21 | V Girls Tennis | NVL Championships | Home - Woodland HS Tennis courts [Directions] | 12:00 p.m. | warm ups noon/start time 1pm | |
| Wed., 5/22 | V Baseball | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Boys Golf | St. Paul Catholic | Home - Oxford Greens [Directions] | 2:30 p.m. | Woodland 236 Tom Conroy 47 Mark Barbarito 60 St. Paul 171 | |
| Wed., 5/22 | V Softball | NVL Semi Finals | Away - Seymour HS | TBA | ||
| Thu., 5/23 | V Baseball | NVL Championships | Away - Municipal Stadium | 6:00 p.m. | ||
| Thu., 5/23 | V Boys Golf | Kaynor Tech | Home - Oxford Greens [Directions] | 2:30 p.m. | Woodland Tom Conroy 44 Mark Barbarito 50 Kaynor Tech. | |
| Fri., 5/24 | V Boys Tennis | CIAC Tourney Through Rnd. of 16 | Away - Conard HS [Directions] | 8:30 a.m. | ||
| Fri., 5/24 | V Girls Tennis | CIAC Tourney Qualifying Round | Away - Highest Seed | TBA | ||
| Sat., 5/25 | V Baseball | CIAC Tourney Qualifying Round | Away - Higher Seed | TBA | ||
| Sat., 5/25 | V Softball | CIAC Tourney Qualifying Round | Away - Higher Seed | TBA | ||
| Sat., 5/25 | V Girls Tennis | CIAC Tourney 1st Rounds | Away - Highest Seed | TBA | ||
| Tue., 5/28 | V Baseball | Wolcott Tech | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/28 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | V Boys Tennis | CIAC Tourney Quarterfinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | V Softball | Jonathan Law | Home - Woodland Softball Field [Directions] | 4:00 p.m. | L 2-4 | |
| Tue., 5/28 | V Girls Tennis | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Through Quarterfinals | Away - Conard HS [Directions] | TBA | ||
| Wed., 5/29 | V Softball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Wed., 5/29 | V Girls Tennis | CIAC Tourney Semifinals | Away - Higher Seed | TBA | ||
| Thu., 5/30 | V Baseball | Lewis Mills | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 5/30 | V Boys Golf | NVL Tournament | Away - Watertown | TBA | ||
| Thu., 5/30 | V Boys Tennis | CIAC Tourney Finals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Girls Tennis | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Fri., 5/31 | V Softball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 6/1 | V Baseball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 6/1 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Wesleyan [Directions] | 12:00 p.m. | ||
| Sat., 6/1 | V Girls Tennis | State Open Qualifying, 1st and 2nd Rounds | Away - Singles @ Conard/Doubles @ Hall | 1:00 p.m. | ||
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | ||
| Mon., 6/3 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | ||
| Mon., 6/3 | V Girls Tennis | State Open Round of 16/Quarterfinals | Away - Yale University [Directions] | 12:00 p.m. | ||
| Tue., 6/4 | V Baseball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Tue., 6/4 | V Boys Golf | CIAC Div. III Championship | Away - Fairview Farms - Harwinton [Directions] | 8:30 a.m. | ||
| Tue., 6/4 | V Boys Golf | CIAC Div. III Championship | Away - Fairview Farms - Harwinton [Directions] | 8:30 a.m. | ||
| Tue., 6/4 | V Boys Tennis | State Open Singles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Tue., 6/4 | V Softball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Tue., 6/4 | V Girls Tennis | State Open Semifinals | Away - Yale University [Directions] | 3:00 p.m. | ||
| Wed., 6/5 | V Boys Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Wed., 6/5 | V Girls Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Sat., 6/8 | V Baseball | CIAC Tourney Final | Away - Palmer Field, Middletown [Directions] | TBA | ||
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Softball | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||