| Woodland 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 329 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 9/26 | V Girls Volleyball | Naugatuck (Scrim.) | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 9:00 a.m. | ||
| Tue., 9/29 | V Boys Soccer | Naugatuck (Scrim.) | Away - Naugatuck HS-Veterans Field [Directions] | 5:15 p.m. | ||
| Tue., 9/29 | V Girls Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 10/1 | V Boys Soccer | Derby | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:15 p.m. | W 8-1 | |
| Thu., 10/1 | V Girls Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:15 p.m. | W 9-0 | |
| Fri., 10/2 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:30 p.m. | W 3-2 | |
| Fri., 10/2 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 5:30 p.m. | W 2-0 | |
| Sat., 10/3 | V Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 10:00 a.m. | T 1-1 | |
| Sat., 10/3 | V Girls Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 2:00 p.m. | W 4-1 | |
| Mon., 10/5 | V Girls Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:15 p.m. | W 4-1 | |
| Tue., 10/6 | V Boys Soccer | O'Brien Tech | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 10/6 | V Girls Swimming and Diving | Watertown | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Virtual Meet | |
| Tue., 10/6 | V Girls Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 0-3 | |
| Tue., 10/6 | JV Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 10/7 | V Girls Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 4-3 | |
| Wed., 10/7 | FR Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Boys Soccer | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:30 p.m. | W 7-1 | |
| Thu., 10/8 | V Girls Volleyball | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 10/8 | JV Girls Volleyball | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/9 | V Boys Cross Country | Holy Cross | Home - Woodland HS-Track [Directions] | 3:45 p.m. | ||
| Fri., 10/9 | V Girls Cross Country | Holy Cross | Home - Woodland HS-Track [Directions] | 3:45 p.m. | ||
| Fri., 10/9 | V Girls Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 4:00 p.m. | ||
| Sat., 10/10 | JV Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 10:00 a.m. | ||
| Mon., 10/12 | V Girls Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 4-0 | |
| Tue., 10/13 | V Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 10/13 | V Girls Swimming and Diving | Oxford | Home - Woodland HS-pool [Directions] | 4:15 p.m. | ||
| Tue., 10/13 | V Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Tue., 10/13 | JV Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 10/14 | V Boys Cross Country | Seymour | Home - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Wed., 10/14 | V Girls Cross Country | Seymour | Home - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Wed., 10/14 | V Girls Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 10/15 | V Boys Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 10/15 | V Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/15 | JV Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/16 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/16 | V Girls Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Sat., 10/17 | JV Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 9:00 a.m. | ||
| Sat., 10/17 | JV Girls Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | Postponed | ||
| Mon., 10/19 | V Girls Soccer | Derby | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:15 p.m. | W 8-0 | |
| Tue., 10/20 | V Boys Cross Country | Oxford | Home - Woodland HS-Track [Directions] | 3:45 p.m. | ||
| Tue., 10/20 | V Boys Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 3-2 | |
| Tue., 10/20 | V Girls Cross Country | Oxford | Home - Woodland HS-Track [Directions] | 3:45 p.m. | ||
| Wed., 10/21 | V Girls Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 10/22 | V Boys Soccer | O'Brien Tech | Away - OBrien Tech-O'Brien Tech Athletic Complex [Directions] | 3:00 p.m. | W 3-1 | |
| Thu., 10/22 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Thu., 10/22 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 10/23 | V Girls Swimming and Diving | Watertown | Home - Woodland HS-pool [Directions] | 3:45 p.m. | Virtual Meet | |
| Fri., 10/23 | V Girls Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 10/23 | FR Girls Volleyball | Naugatuck | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/24 | JV Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | JV Girls Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:00 a.m. | ||
| Mon., 10/26 | JV Boys Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Mon., 10/26 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 5:30 p.m. | T 2-2 | |
| Tue., 10/27 | V Boys Cross Country | Naugatuck | Home - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Tue., 10/27 | V Boys Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | W 4-0 | |
| Tue., 10/27 | V Girls Cross Country | Naugatuck | Home - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Tue., 10/27 | V Girls Swimming and Diving | Seymour | Home - Woodland HS-pool [Directions] | 5:45 p.m. | ||
| Tue., 10/27 | V Girls Volleyball | O'Brien Tech | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Tue., 10/27 | JV Girls Volleyball | O'Brien Tech | Home - Woodland HS-Gym [Directions] | 3:45 p.m. | W 2-0 | |
| Wed., 10/28 | V Girls Soccer | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:30 p.m. | W 4-0 | |
| Thu., 10/29 | V Boys Soccer | O'Brien Tech | Away - OBrien Tech-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 10/29 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/29 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | Postponed | ||
| Thu., 10/29 | FR Girls Volleyball | Shelton | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/30 | V Girls Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | Canceled | Cancelled | |
| Fri., 10/30 | V Girls Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/31 | JV Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | JV Girls Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 8:30 a.m. | ||
| Sat., 10/31 | FR Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 11/2 | V Girls Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:15 p.m. | W 2-0 | |
| Mon., 11/2 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 3:30 p.m. | Virtual Meet | |
| Mon., 11/2 | V Girls Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Mon., 11/2 | V Girls Volleyball | O'Brien Tech | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Mon., 11/2 | JV Girls Volleyball | O'Brien Tech | Home - Woodland HS-Gym [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 11/3 | V Boys Cross Country | Derby | Home - Woodland HS-Track [Directions] | 3:00 p.m. | ||
| Tue., 11/3 | V Boys Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 8-1 | |
| Tue., 11/3 | V Girls Cross Country | Derby | Home - Woodland HS-Track [Directions] | 3:00 p.m. | ||
| Wed., 11/4 | V Girls Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 3-0 | |
| Thu., 11/5 | V Boys Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 4-1 | |
| Thu., 11/5 | V Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | W 8-2 | |
| Thu., 11/5 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | Postponed | ||
| Tue., 11/10 | V Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/5 | V Boys Basketball | North Haven (Scrim.) | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 2/5 | V Girls Basketball | Thomaston (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/10 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:00 p.m. | L 55-51 OT | |
| Sat., 2/13 | V Boys Basketball | Oxford (Scrim.) | Away - Oxford HS-Main Gym [Directions] | 11:00 a.m. | ||
| Tue., 2/16 | V Boys Basketball | Derby | Away - Derby HS-Gym [Directions] | 6:30 p.m. | L 62-58 | |
| Tue., 2/16 | JV Boys Basketball | Derby | Away - Derby HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/16 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS-CHS Pool [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 2/16 | V Boys Swimming and Diving | Crosby/WCA | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 100-55 [Detailed Results] | Virtual Swim Meet |
| Fri., 2/19 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | ||
| Sat., 2/20 | V Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 1:30 p.m. | W 62-42 | |
| Sat., 2/20 | JV Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/20 | FR Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/20 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 10:30 a.m. | W 51-40 | |
| Sat., 2/20 | V Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/20 | JV Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | JV Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Tue., 2/23 | V Boys Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 70-52 | |
| Tue., 2/23 | JV Boys Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/23 | V Boys Swimming and Diving | Seymour | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Virtual Meet | |
| Wed., 2/24 | V Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 4:30 p.m. | L 41-56 | |
| Wed., 2/24 | JV Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 2:45 p.m. | ||
| Wed., 2/24 | V Boys Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 58-61 | |
| Wed., 2/24 | JV Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 2/25 | FR Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Fri., 2/26 | V Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 47-55 | |
| Fri., 2/26 | JV Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/26 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | W 46-39 | |
| Fri., 2/26 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/27 | FR Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 11:00 a.m. | ||
| Mon., 3/1 | V Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 64-73 | |
| Mon., 3/1 | JV Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Mon., 3/1 | V Boys Swimming and Diving | Kennedy | Away - J F Kennedy HS Turf-John Reardon Pool [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/2 | ||||||
| Mon., 3/1 | V Boys Swimming and Diving | Kennedy | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 89-49 | Virtual Meet |
| Tue., 3/2 | V Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 6:00 p.m. | W 49-39 | |
| Wed., 3/3 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 7:00 p.m. | W 57-39 | |
| Wed., 3/3 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 3/3 | V Boys Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 103-81 | Virtual meet |
| Wed., 3/3 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Wed., 3/3 | V Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 47-44 | |
| Wed., 3/3 | JV Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 3/5 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | W 61-47 | |
| Fri., 3/5 | JV Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 3/5 | V Boys Swimming and Diving | Sacred Heart | Home - Woodland HS-pool [Directions] | 6:00 p.m. | Win: 101-74 | |
| Fri., 3/5 | V Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 53-34 | |
| Fri., 3/5 | JV Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Sat., 3/6 | FR Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 9:30 a.m. | ||
| Mon., 3/8 | V Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 52-43 | |
| Mon., 3/8 | JV Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 3/9 | V Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 78-68 | |
| Tue., 3/9 | JV Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 3/9 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 88-63 | Virtual meet |
| Tue., 3/9 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby HS-Gil Cyr Natatorium [Directions] | 5:30 p.m. | ||
| Tue., 3/9 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 6:30 p.m. | L 37-73 | |
| Tue., 3/9 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 3/11 | FR Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 3/12 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:30 p.m. | L 83-86 | |
| Fri., 3/12 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 3/12 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 4:00 p.m. | ||
| Fri., 3/12 | V Boys Swimming and Diving | Watertown | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 124-44 | Virtual Meet |
| Fri., 3/12 | V Girls Basketball | Crosby | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 41-15 | |
| Fri., 3/12 | JV Girls Basketball | Crosby | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 3/13 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 11:00 a.m. | ||
| Mon., 3/15 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 57-55 | |
| Mon., 3/15 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:30 p.m. | ||
| Mon., 3/15 | V Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 52-43 | |
| Mon., 3/15 | JV Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Tue., 3/16 | V Boys Swimming and Diving | Holy Cross | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Loss: 102-83 | |
| Wed., 3/17 | V Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | Cancelled | |
| Wed., 3/17 | V Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 75 84 | |
| Wed., 3/17 | JV Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 3/17 | JV Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 3/17 | FR Boys Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 3/17 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:30 p.m. | W 68-40 | |
| Wed., 3/17 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 3/18 | FR Boys Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 3/19 | V Boys Swimming and Diving | Oxford | Home - Woodland HS-pool [Directions] | 5:30 p.m. | Win: 102-79 | |
| Sat., 3/20 | V Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 10:00 a.m. | W 62-61 | |
| Sat., 3/20 | V Girls Basketball | Watertown | Home - Woodland HS-Gym [Directions] | 1:00 p.m. | ||
| Mon., 3/22 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 7:15 p.m. | L 52-49 | |
| Mon., 3/22 | V Girls Basketball | Sacred Heart | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 3/24 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS (Waterbury) [Directions] | 6:00 p.m. | ||
| Wed., 3/24 | V Boys Swimming and Diving | Kennedy, Holy Cross | Away - John F. Kennedy HS-John Reardon Pool [Directions] | 6:00 p.m. | ||
| Wed., 3/24 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | ||
| Thu., 4/1 | V Softball | Trumbull (Scrim.) | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 4/3 | V Softball | Southington (Scrim.) | Away - Southington HS-Softball Varsity Field [Directions] | 10:30 a.m. | ||
| Tue., 4/6 | V Baseball | Pomperaug (Scrim.) | Away - Pomperaug HS-Baseball Field [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 4/6 | FR Baseball | Pomperaug (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 4/6 | V Softball | Trumbull (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 4/7 | V Baseball | Holy Cross (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Wed., 4/7 | V Softball | WCA (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Thu., 4/8 | V Softball | Nonnewaug (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Sat., 4/10 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 11:00 a.m. | L 0-5-0 | |
| Sat., 4/10 | V Softball | Sacred Heart | Away - Municipal Stadium-Joan Joyce Softball Diamond | 11:00 a.m. | W 22-0 | |
| Sat., 4/10 | V Girls Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | 11:00 a.m. | L 2-5 | |
| Mon., 4/12 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | 2:00 p.m. | Watertown 189 Woodland 214 Mark Barbarito 49 Ryan Bucciferro 51 Albert Marchant 56 Aden Ianniruberto 58 | |
| Mon., 4/12 | V Softball | Wolcott | Away - Wolcott HS-George Babcock Softball Field [Directions] | 3:45 p.m. | W 8-5 | |
| Tue., 4/13 | V Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | W 13-3 (5) | |
| Tue., 4/13 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Tue., 4/13 | V Boys Outdoor Track | Oxford | Home - Woodland HS-Track [Directions] | 3:15 p.m. | Woodland 107, Oxford 29 | |
| Tue., 4/13 | V Boys Outdoor Track | Holy Cross, Oxford | Away - Holy Cross [Directions] | 3:30 p.m. | ||
| Tue., 4/13 | V Boys Tennis | Sacred Heart | Away - Fulton Park-Tennis Courts | 3:00 p.m. | W 3-0 | |
| Tue., 4/13 | V Girls Outdoor Track | Oxford | Home - Woodland HS-Track [Directions] | 3:15 p.m. | Woodland 115, Oxford 28 | |
| Tue., 4/13 | V Girls Outdoor Track | Holy Cross, Oxford | Away - Holy Cross [Directions] | 3:30 p.m. | ||
| Tue., 4/13 | JV Softball | Wolcott | Away - Wolcott HS-JV Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 4/13 | V Girls Tennis | Sacred Heart | Home - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | L 3-4 | |
| Wed., 4/14 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS-Baseball Diamond [Directions] | 4:00 p.m. | W 5-3 | |
| Wed., 4/14 | FR Baseball | St. Paul Catholic | Away - Page Park-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 4/14 | V Softball | Wilby | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | W 19-0 | |
| Wed., 4/14 | V Girls Tennis | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 4/16 | FR Baseball | Naugatuck | Away - Rotary Field-Baseball [Directions] | Postponed | ||
| Fri., 4/16 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Canceled | Cancelled | |
| Fri., 4/16 | V Softball | Crosby | Away - Municipal Stadium (Waterbury, CT)-Joan Joyce Softball Diamond [Directions] | 6:00 p.m. | W 27-1 | |
| Sat., 4/17 | JV Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Sat., 4/17 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 11:00 a.m. | W 4-1 | |
| Sat., 4/17 | JV Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 4/19 | V Baseball | Derby | Away - Payden Park-Payden Field [Directions] | 3:00 p.m. | W 13-2 (5) | |
| Mon., 4/19 | V Softball | Derby | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | W 19-1 | |
| Tue., 4/20 | JV Baseball | Derby | Away - Leo F. Ryan Athletic Complex-Payden Park [Directions] | 3:00 p.m. | ||
| Tue., 4/20 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | 2:00 p.m. | Woodland 240 Aden Ianniruberto 57 Rayn Bucciferro 59 Albert Marchant 56 Nick Sciaretto 68 Torrington 232 | |
| Tue., 4/20 | V Boys Outdoor Track | Sacred Heart, Wilby | Home - Woodland HS-Track [Directions] | 3:30 p.m. | Woodland 111, Sacred Heart 33 Woodland 119, Wilby 26 | |
| Tue., 4/20 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 | No Bus |
| Tue., 4/20 | V Girls Outdoor Track | Sacred Heart, Wilby | Home - Woodland HS-Track [Directions] | 3:30 p.m. | Woodland 135, Sacred Heart 10 Woodland 142 Wilby 2 | |
| Thu., 4/22 | JV Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Thu., 4/22 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | 2:30 p.m. | Woodland 236 Aden Ianniruberto 63 Nick Sciaretto 66 Ryan Bucciferro 41 Skylar Difazio 66 Seymour 223 | |
| Thu., 4/22 | JV Softball | Naugatuck | Home - Woodland HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 4/23 | V Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | 3:15 p.m. | W 2-1 | |
| Fri., 4/23 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:00 p.m. | ||
| Fri., 4/23 | V Boys Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | L 1-4 | |
| Fri., 4/23 | JV Boys Tennis | Wilcox Tech | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 4/23 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:15 p.m. | W 10-8 | |
| Fri., 4/23 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | 3:00 p.m. | W 7-0 | |
| Sat., 4/24 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic HS-Baseball Diamond [Directions] | 12:00 p.m. | ||
| Sat., 4/24 | V Softball | Naugatuck | Home - Woodland HS-Softball Diamond [Directions] | 10:30 a.m. | W 8-6 | |
| Sat., 4/24 | V Girls Tennis | St. Paul Catholic | Away - St. Paul Catholic HS-Page Park, Tennis Courts [Directions] | 10:00 a.m. | W 5-2 | |
| Mon., 4/26 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 3:00 p.m. | W 20-2 (5) | |
| Mon., 4/26 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Woodland 225 Mark Barbarito 57 Aden Ianniruberto 62 Ryan Bucciferro 48 Albert Marchant 58 Holy Cross 187 | NO BUS |
| Mon., 4/26 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 4/26 | V Softball | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:00 p.m. | W 15-0 | |
| Mon., 4/26 | V Girls Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | No Bus |
| Tue., 4/27 | JV Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 3:00 p.m. | ||
| Tue., 4/27 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | 2:00 p.m. | Sacred Heart228 Woodland 232 Mark Barbarito 49 Ryan Bucciferro 57-d'q'd Aden Ianniruberto 60 Skykar Difazio 66 Nick Sciaretto 67 | |
| Tue., 4/27 | V Boys Golf | Naugatuck | Away - Oxford Greens [Directions] | 2:15 p.m. | Naugatuck 236 Woodland 242 Mark Barbarito 49 Ryan Bucciferro 57-d'q'd Aden Ianniruberto 60 Skykar Difazio 66 Nick Sciaretto 67 | |
| Tue., 4/27 | V Boys Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS-WHS Track and Lower Field [Directions] | 3:30 p.m. | Naugatuck 119, WRHS 31 WRHS 104 Wolcott 45 | |
| Tue., 4/27 | V Girls Outdoor Track | Wolcott, Naugatuck | Away - Wolcott HS-WHS Track and Lower Field [Directions] | 3:30 p.m. | WRHS 124 Naugatuck 26 WRHS 127 Wolcott 21 | |
| Wed., 4/28 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | W 3-0 | No Bus |
| Wed., 4/28 | FR Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 4/28 | FR Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | Canceled | Cancelled | |
| Wed., 4/28 | V Boys Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 4/28 | V Softball | Torrington | Home - Woodland HS-Softball Diamond [Directions] | 3:45 p.m. | W 8-3 | |
| Wed., 4/28 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 3:00 p.m. | W 4-3 | |
| Thu., 4/29 | JV Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | Postponed | ||
| Fri., 4/30 | V Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | 3:15 p.m. | W 4-3 | |
| Fri., 4/30 | V Boys Tennis | Holy Cross | Away - Holy Cross [Directions] | 3:30 p.m. | W 4-1 | No Bus |
| Fri., 4/30 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 4/30 | V Girls Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | L 2-5 | |
| Sat., 5/1 | V Baseball | Sacred Heart | Away - Fulton Park-Baseball Diamond | 11:00 a.m. | W 10-0 (6) | |
| Sat., 5/1 | JV Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 5/1 | JV Softball | Torrington | Home - Woodland HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 5/3 | V Baseball | Watertown | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 5/3 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:30 p.m. | No Bus | |
| Mon., 5/3 | V Boys Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 | |
| Mon., 5/3 | V Softball | Watertown | Home - Woodland HS-Softball Diamond [Directions] | 3:45 p.m. | W 8-3 | |
| Tue., 5/4 | JV Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/19 | ||||||
| Tue., 5/4 | V Girls Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | L 1-6 | |
| Thu., 5/6 | V Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 3:30 p.m. | W 4-2 | No Bus |
| Thu., 5/6 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 5/6 | V Boys Outdoor Track | Kennedy, Torrington | Home - Woodland HS-Track [Directions] | 3:45 p.m. | WRHS 118 Torrington 31 WRHS 117 Kennedy 32 | |
| Thu., 5/6 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | No Bus |
| Thu., 5/6 | V Girls Outdoor Track | Kennedy, Torrington | Home - Woodland HS-Track [Directions] | 3:45 p.m. | WRHS 129 Kennedy 16 WRHS 119 Torrington 26 | |
| Thu., 5/6 | V Softball | Holy Cross | Away - Municipal Stadium (Waterbury, CT)-Joan Joyce Softball Diamond [Directions] | 6:00 p.m. | W 16-0 | No Bus |
| Thu., 5/6 | V Girls Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 5/7 | V Baseball | Thomaston | Home - Woodland HS-Baseball Diamond [Directions] | 4:00 p.m. | W 9-3 | |
| Fri., 5/7 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | W 6-1 | Senior Night |
| Sat., 5/8 | V Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | W Forfeit | |
| Sat., 5/8 | FR Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 5/8 | V Boys Tennis | Sacred Heart | Home - Woodland HS-Tennis Courts [Directions] | 10:00 a.m. | W 4-1 | |
| Sat., 5/8 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 10:00 a.m. | W 23-0 | |
| Mon., 5/10 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | 2:00 p.m. | Wolcott 221 Woodland 241 Albert Marchant 59 Aden Ianniruberto 59 Nick Sciaretto 62 Skylar Difazio 68 | |
| Tue., 5/11 | V Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | 4:45 p.m. | L 7-2 | |
| Tue., 5/11 | JV Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 5/11 | FR Baseball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:30 p.m. | ||
| Tue., 5/11 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 3:00 p.m. | Woodland 249 Ryan Bucciferro 51 Aden Inniruberto 58 Nick Sciaretto 69 Skylar Difazio 65 St. Paul 181 | No Bus |
| Tue., 5/11 | V Boys Outdoor Track | Derby, St. Paul Catholic | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | Derby 78 WRHS 72 WRHS 136 St Paul 11 | |
| Tue., 5/11 | V Girls Outdoor Track | Derby, St. Paul Catholic | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | WRHS 120 Derby 29 WRHS 126 St Paul 15 | |
| Tue., 5/11 | V Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | 4:45 p.m. | W 21-3 | |
| Tue., 5/11 | V Girls Tennis | Nonnewaug | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | Cancelled | |
| Wed., 5/12 | V Baseball | Ansonia | Home - Woodland HS-Baseball Diamond [Directions] | 3:15 p.m. | W 2-1 | |
| Wed., 5/12 | V Boys Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 | Senior Night |
| Wed., 5/12 | V Softball | Ansonia | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 6:00 p.m. | W 16-0 | Senior Night |
| Wed., 5/12 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Chase Park [Directions] | 3:30 p.m. | W 7-0 | No Bus |
| Thu., 5/13 | JV Baseball | Ansonia | Home - Woodland HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Thu., 5/13 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | 2:30 p.m. | Woodland 226 Ryan Bucciferro 44 Aden Innuriberto 58 Nick Sciaretto 61 Skylar Difazio 63 Sacred Heart 202 | |
| Thu., 5/13 | V Girls Tennis | Ansonia | Home - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | W 6-1 | |
| Fri., 5/14 | V Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | W 10-4 | NO BUS |
| Fri., 5/14 | V Boys Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 3:30 p.m. | W 4-1 | No Bus |
| Fri., 5/14 | V Girls Tennis | Seymour | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | L 2-5 | |
| Sat., 5/15 | V Baseball | Derby | Home - Woodland HS-Baseball Diamond [Directions] | 2:30 p.m. | W 12-1 (5) | Senior Night |
| Sat., 5/15 | JV Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/15 | JV Baseball | Wolcott | Away - Wolcott HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Sat., 5/15 | V Boys Outdoor Track | Seymour, WCA | Home - Woodland HS-Track [Directions] | 10:00 a.m. | WRHS 105 Seymour 45 WRHS 118 WCA 31 | Senior Night |
| Sat., 5/15 | V Girls Outdoor Track | Seymour, WCA | Home - Woodland HS-Track [Directions] | 10:00 a.m. | WRHS 97 Seymour 53 WRHS 137 WCA 9 | Senior Night |
| Sat., 5/15 | V Softball | Derby | Away - Leo F. Ryan Athletic Complex-Payden Park - William Red Clynch Memorial Softba [Directions] | 6:00 p.m. | W 20-0 | |
| Sat., 5/15 | JV Softball | Derby | Away - Payden Park-Payden Field [Directions] | Canceled | Cancelled | |
| Mon., 5/17 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 3:15 p.m. | W 6-0 | |
| Mon., 5/17 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 2:00 p.m. | Woodland 227 Ryan Bucciferro 50 Aden Innuriberto 50 Nick Sciaretto 63 Dean Norton 64 Holy Cross 188 | |
| Mon., 5/17 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W Forfeit | |
| Tue., 5/18 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:30 p.m. | W 10-7 | |
| Tue., 5/18 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Canceled | Cancelled | |
| Tue., 5/18 | V Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | 3:15 p.m. | W 7-0 | |
| Wed., 5/19 | FR Baseball | Naugatuck | Away - Rotary Field-Baseball [Directions] | 3:30 p.m. | ||
| Wed., 5/19 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 5/19 | V Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | 3:15 p.m. | W 4-3 | |
| Wed., 5/19 | V Girls Tennis | Holy Cross | Away - Holy Cross [Directions] | 3:00 p.m. | ||
| Thu., 5/20 | V Baseball | WCA | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | W 12-1 (5) | |
| Thu., 5/20 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | W 3-2 | |
| Thu., 5/20 | JV Softball | Kennedy | Away - Town Plot Park [Directions] | Canceled | Cancelled | |
| Sat., 5/22 | V Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 11:30 a.m. | ||
| Sat., 5/22 | V Softball | Watertown | Home - Woodland HS-Softball Diamond [Directions] | 11:30 a.m. | ||
| Mon., 5/24 | V Softball | Seymour | Home - Seymour HS-Softball Diamond [Directions] | 7:00 p.m. | ||
| Mon., 5/24 | V Girls Tennis | NVL Indvidual Girls Tournament | Home - Woodland HS-Tennis Courts [Directions] | 12:00 p.m. | ||
| Tue., 5/25 | V Girls Tennis | NVL Indvidual Girls Tournament | Home - Woodland HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Wed., 5/26 | V Softball | Naugatuck | Home - Naugatuck HS-Softball Diamond [Directions] | 5:30 p.m. | ||
| Fri., 5/28 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 6/1 | V Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | 3:15 p.m. | ||
| Wed., 6/2 | V Baseball | Watertown | Home - Woodland HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 6/2 | V Boys Outdoor Track | CIAC Class M Boys Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 6/2 | V Girls Outdoor Track | CIAC Class M Girls Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 6/2 | V Softball | Nonnewaug | Home - Woodland HS-Softball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 6/3 | V Boys Golf | NVL Championship Tournament | Away - Watertown Golf Club | 7:30 a.m. | ||
| Sat., 6/5 | V Baseball | Bacon Academy | Home - Woodland HS-Baseball Diamond [Directions] | 3:00 p.m. | ||
| Sat., 6/5 | V Softball | Wolcott | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Mon., 6/7 | V Boys Golf | CIAC Boys Div. III Golf Championship | Away - Stanley GC | 8:00 a.m. | ||
| Mon., 6/7 | V Softball | North Branford | Home - West Haven HS-Frank Biondi Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 6/9 | V Baseball | Northwestern | Away - Muzzy Field-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Wed., 6/9 | V Boys Outdoor Track | CIAC Open Boys Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Wed., 6/9 | V Girls Outdoor Track | CIAC Open Girls Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Sat., 6/12 | V Boys Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/14 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Mon., 6/14 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Tue., 6/15 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 1 | Away - Manchester | 10:00 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 1 | Away - Manchester | 10:30 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||