| Woodland 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 526 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/23 | V Football | Joint Practice @ Weston HS | Away - Not Listed | 8:00 a.m. | ||
| Sat., 8/26 | V Football | Platt, Jonathan Law, Lyman Hall (Scrim.) | Away - Falcon Field (Meriden, CT)-Football Field [Directions] | 9:00 a.m. | ||
| Tue., 8/29 | V Girls Soccer | Jonathan Law (Scrim.) | Home - Woodland HS-Woodland Soccer Field [Directions] | 4:30 p.m. | ||
| Tue., 8/29 | V Girls Volleyball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 8/31 | V Football | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Thu., 8/31 | V Girls Volleyball | Cheshire (Scrim.) | Away - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 9/1 | V Girls Soccer | Sheehan (Scrim.) | Home - Woodland HS-Woodland Soccer Field [Directions] | 4:30 p.m. | ||
| Sat., 9/2 | V Boys Cross Country | Beach Run @ West Haven | Away - Not Listed | 10:00 a.m. | ||
| Sat., 9/2 | V Boys Soccer | Sheehan (Scrim.) | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | V Girls Cross Country | Beach Run @ West Haven | Away - Not Listed | 10:00 a.m. | ||
| Sat., 9/2 | V Girls Volleyball | East Haven, Amity, Coginchaug, Fitch, Haddam-Killingworth, Nonnewaug, Sheehan, Stratford | Away - East Haven HS-Gym | 9:00 a.m. | ||
| Tue., 9/5 | V Boys Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Default Facility | 4:00 p.m. | Cancelled | |
| Tue., 9/5 | V Girls Volleyball | Northwestern (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/7 | V Football | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | L 14-20 (OT) | |
| Thu., 9/7 | V Boys Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/7 | V Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 8:00 p.m. | T 1-1 | |
| Fri., 9/8 | JV Football | Holy Cross | Home - Woodland HS-Woodland Football Field [Directions] | Postponed | ||
| Fri., 9/8 | JV Boys Soccer | Pomperaug | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Postponed | ||
| Fri., 9/8 | V Girls Swimming and Diving | Sheehan | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win 102-84 | |
| Fri., 9/8 | V Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/8 | JV Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | L 1-2 | |
| Sat., 9/9 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | Boys: 5th Place JV | |
| Sat., 9/9 | V Boys Soccer | Wilby | Away - Wilby HS-Pedro DeBrito Field [Directions] | 11:00 a.m. | W 8-0 | |
| Sat., 9/9 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | Girls: 1st and 2nd place in JV Race 8th place in Freshman Race | |
| Sat., 9/9 | V Girls Soccer | Hamden | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | W 6-2 | |
| Sat., 9/9 | JV Girls Soccer | Hamden | Home - Woodland HS-Woodland Soccer Field [Directions] | 12:15 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Watertown, Holy Cross, St. Paul Catholic | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 4:45 p.m. | HCHS 26, WRHS 31 WRHS 19, St Paul 38 WRHS 22, Watertown 33 | |
| Tue., 9/12 | V Boys Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 7-2 | |
| Tue., 9/12 | V Girls Cross Country | Watertown, Holy Cross, St. Paul Catholic | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 4:45 p.m. | HCHS 29, WRHS 30 Watertown 24, WRHS 32 WRHS 15, St Paul 45 | |
| Tue., 9/12 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Ave-Chargers Field [Directions] | 3:30 p.m. | W 3-0 | |
| Thu., 9/14 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Thu., 9/14 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | W 2-1 | |
| Thu., 9/14 | FR Girls Volleyball | Seymour (Scrim.) | Away - Seymour HS-Gym [Directions] | 3:00 p.m. | ||
| Fri., 9/15 | V Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 7:00 p.m. | W 46-6 | |
| Fri., 9/15 | V Girls Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 9/15 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 96-52 | |
| Sat., 9/16 | JV Football | Wolcott | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/16 | JV Girls Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Tue., 9/19 | V Boys Cross Country | Crosby, Oxford | Away - Bucks Hill (MONTOE) Park-XC Course [Directions] | 3:45 p.m. | WRHS 15, Crosby 45 WRHS 22, Oxford 35 | |
| Tue., 9/19 | V Boys Soccer | Bassick | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 9/19 | V Girls Cross Country | Crosby, Oxford | Away - Bucks Hill (MONTOE) Park-Soccer Pitch [Directions] | 3:45 p.m. | WRHS 16, Crosby 44 WRHS 15, Oxford 50 | |
| Tue., 9/19 | V Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:00 p.m. | W 5-1 | |
| Tue., 9/19 | V Girls Swimming and Diving | Watertown | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win 95-68 | |
| Tue., 9/19 | V Girls Volleyball | Derby | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/19 | JV Girls Volleyball | Derby | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 9/20 | V Boys Soccer | Torrington | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Wed., 9/20 | JV Girls Soccer | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 9/21 | JV Boys Soccer | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:30 p.m. | ||
| Thu., 9/21 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/21 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 9/21 | FR Girls Volleyball | East Haven | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/22 | V Boys Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | T 2-2 | |
| Fri., 9/22 | V Girls Soccer | Wolcott | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 9/22 | V Girls Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:00 p.m. | Win 99-81 | |
| Fri., 9/22 | V Girls Volleyball | Torrington | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/22 | JV Girls Volleyball | Torrington | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/23 | V Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 10:00 a.m. | W 46-8 | |
| Sat., 9/23 | JV Girls Soccer | Wolcott | Home - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Mon., 9/25 | JV Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Tue., 9/26 | V Boys Cross Country | Derby, Seymour, Torrington | Home - Woodland HS-Track [Directions] | 3:45 p.m. | WRHS 16, Seymour 33 WRHS 21, Torrington 34 WRHS 18, Derby 41 | |
| Tue., 9/26 | V Girls Cross Country | Derby, Seymour, Torrington | Home - Woodland HS-Track [Directions] | 3:45 p.m. | WRHS 25, Derby 30 WRHS 24, Seymour 31 WRHS 15, Torrington 50 | |
| Tue., 9/26 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 9/26 | V Girls Swimming and Diving | Torrington | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win 84-46 | |
| Tue., 9/26 | V Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/26 | JV Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | W 2-0 | |
| Wed., 9/27 | V Boys Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Wed., 9/27 | JV Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | Canceled | Cancelled | |
| Thu., 9/28 | JV Boys Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Girls Soccer | St. Paul Catholic | Home - Woodland HS-Woodland Soccer Field [Directions] | 4:45 p.m. | W 9-0 | |
| Thu., 9/28 | V Girls Swimming and Diving | Kennedy | Away - John F. Kennedy HS-JFK Pool [Directions] | 4:00 p.m. | Win 57-27 | |
| Thu., 9/28 | V Girls Volleyball | Wolcott | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Thu., 9/28 | JV Girls Volleyball | Wolcott | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 9/29 | V Girls Volleyball | Naugatuck | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | W 3-0 | |
| Fri., 9/29 | JV Girls Volleyball | Naugatuck | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | L 1-2 | |
| Sat., 9/30 | V Football | Gilbert/Northwestern/Housy | Home - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 2:00 p.m. | W 34-0 | |
| Sat., 9/30 | JV Girls Soccer | St. Paul Catholic | Home - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Sat., 9/30 | V Girls Swimming and Diving | Hall, Amity, Conard, Daniel Hand, East Lyme, Glastonbury, Southington | Away - Cornerstone Aquatics Center-Pool | 3:00 p.m. | ||
| Sat., 9/30 | FR Girls Volleyball | Crosby, Seymour, Wolcott | Home - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/2 | JV Football | Gilbert/Northwestern/Housy | Away - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Boys Soccer | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 3:30 p.m. | W 4-2 | |
| Mon., 10/2 | V Girls Soccer | Watertown | Away - Municipal stadium [Directions] | 6:30 p.m. | W 4-0 | |
| Tue., 10/3 | V Boys Cross Country | Kennedy, Naugatuck, WCA | Home - Woodland HS-Track [Directions] | 2:45 p.m. | WRHS 24, Naugatuck 31 WRHS 15, Kennedy 50 WRHS 19, WCA 38 | |
| Tue., 10/3 | V Girls Cross Country | Kennedy, Naugatuck, WCA | Home - Woodland HS-Track [Directions] | 2:45 p.m. | WRHS 23, Naugatuck 32 WRHS 16, WCA 38 WRHS 15, Kennedy 50 | |
| Tue., 10/3 | JV Girls Soccer | Watertown | Away - Veterans Memorial Park-Veterans Park Field #2 [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland HS-pool [Directions] | 4:45 p.m. | Win 95-77 | |
| Tue., 10/3 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-2 | |
| Tue., 10/3 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:30 p.m. | W 2-1 | |
| Wed., 10/4 | V Boys Soccer | Crosby | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 10/5 | V Girls Volleyball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/5 | JV Girls Volleyball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 10/6 | V Football | Oxford | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | L 13-16 | |
| Fri., 10/6 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | Win 88-77 | |
| Fri., 10/6 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 10/6 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 4:00 p.m. | W 0-2 | |
| Sat., 10/7 | JV Football | Oxford | Away - Oxford HS-Wolverine Field [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | V Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 1:00 p.m. | L 0-3 | |
| Sat., 10/7 | JV Girls Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | Postponed | ||
| Mon., 10/9 | V Girls Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | W 4-0 | |
| Tue., 10/10 | V Boys Cross Country | Wilby, Wolcott | Home - Woodland HS-Track [Directions] | 2:45 p.m. | WR 16, Wolcott 47 WR 15, Wilby 45 | |
| Tue., 10/10 | V Girls Cross Country | Wilby, Wolcott | Home - Woodland HS-Track [Directions] | 2:45 p.m. | WR 18, Wolcott 39 WR 15, Wilby 45 | |
| Tue., 10/10 | V Girls Volleyball | Wilby | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/10 | JV Girls Volleyball | Wilby | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/11 | V Boys Soccer | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 1-0 | |
| Wed., 10/11 | V Girls Swimming and Diving | Suffield | Home - Woodland HS-pool [Directions] | 4:30 p.m. | Win 90-66 | |
| Thu., 10/12 | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | Canceled | Cancelled | |
| Thu., 10/12 | V Girls Swimming and Diving | Jonathan Law | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win 101-82 | |
| Thu., 10/12 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/12 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Thu., 10/12 | FR Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Boys Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 10/13 | V Girls Soccer | Seymour | Away - Seymour HS-turf field [Directions] | 6:00 p.m. | W 4-0 | |
| Fri., 10/13 | V Girls Volleyball | Crosby | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/13 | JV Girls Volleyball | Crosby | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 10/14 | JV Boys Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Sat., 10/14 | JV Girls Soccer | Seymour | Away - Seymour HS-turf field [Directions] | Postponed | ||
| Sat., 10/14 | FR Girls Volleyball | Naugatuck, St. Paul Catholic, Watertown | Home - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/16 | V Boys Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:30 p.m. | L 0-1 | |
| Mon., 10/16 | V Girls Soccer | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | W 3-0 | |
| Tue., 10/17 | JV Boys Soccer | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Tue., 10/17 | V Girls Soccer | Derby | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 9-0 | |
| Tue., 10/17 | V Girls Swimming and Diving | Seymour | Home - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 10/17 | JV Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 10/17 | FR Girls Volleyball | Amity | Home - Woodland HS-Gym [Directions] | 3:45 p.m. | ||
| Wed., 10/18 | V Boys Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 6:00 p.m. | W 9-1 | |
| Thu., 10/19 | V Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 7:00 p.m. | L 7-35 | |
| Thu., 10/19 | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | Canceled | Cancelled | |
| Thu., 10/19 | JV Boys Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Girls Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | 6:00 p.m. | W 9-1 | |
| Thu., 10/19 | V Girls Volleyball | Derby | Away - Derby MS-DMS Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/19 | JV Girls Volleyball | Derby | Away - Derby MS-DMS Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/19 | FR Girls Volleyball | Holy Cross | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/20 | V Girls Swimming and Diving | Weston | Away - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/20 | JV Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 10/21 | JV Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 5:00 p.m. | ||
| Sat., 10/21 | JV Girls Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Sat., 10/21 | JV Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 1:30 p.m. | ||
| Mon., 10/23 | V Boys Soccer | St. Paul Catholic | Home - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 10/23 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/23 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/24 | JV Boys Soccer | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Tue., 10/24 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/25 | V Boys Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-2 | |
| Wed., 10/25 | V Girls Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Wed., 10/25 | V Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Wed., 10/25 | JV Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-1 | |
| Thu., 10/26 | JV Boys Soccer | Watertown | Away - Veterans Memorial Park-Veterans Park [Directions] | 3:30 p.m. | ||
| Thu., 10/26 | JV Girls Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 10/26 | V Girls Volleyball | East Haven | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/26 | JV Girls Volleyball | East Haven | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/27 | V Football | Watertown | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | W 36-27 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class SS Championship | Away | 10:45 a.m. | ||
| Sat., 10/28 | FM Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 9:30 a.m. | ||
| Sat., 10/28 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:30 p.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park | 10:10 a.m. | ||
| Sat., 10/28 | V Girls Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | 11:00 a.m. | W 5-1 | |
| Sat., 10/28 | V Girls Volleyball | Wolcott | Home - Woodland HS-Gym [Directions] | 2:00 p.m. | ||
| Mon., 10/30 | V Girls Soccer | Ansonia | Home - Wolcott HS-Turf Field [Directions] | 5:00 p.m. | W 1-0 | |
| Mon., 10/30 | V Girls Volleyball | Holy Cross | Home - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 11/1 | V Girls Soccer | Watertown | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | St. Paul/Lewis Mills, Kennedy, TBA, Naugatuck, Oxford, Seymour, Watertown | Away - Woodland HS-pool | 6:00 p.m. | ||
| Wed., 11/1 | V Girls Volleyball | Seymour | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 11/3 | V Football | Ansonia | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | L 20-49 | |
| Fri., 11/3 | V Boys Soccer | Thomaston (Scrim.) | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:15 p.m. | ||
| Fri., 11/3 | V Girls Swimming and Diving | St. Paul/Lewis Mills, Kennedy, Naugatuck, Oxford, Seymour, Watertown, Wilby/Kaynor Tech/WCA | Away - John F. Kennedy HS-JFK Pool | 4:30 p.m. | ||
| Sat., 11/4 | JV Football | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 10:00 a.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Plainville | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | W 4-0 | |
| Mon., 11/6 | V Girls Volleyball | Bacon Academy | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 11/7 | V Boys Soccer | Stonington | Home - Woodland HS-Woodland Soccer Field [Directions] | 1:00 p.m. | ||
| Wed., 11/8 | V Girls Soccer | Plainfield | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/8 | V Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 11/10 | V Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 7:00 p.m. | W 48-20 | |
| Fri., 11/10 | V Girls Soccer | RHAM | Home - Woodland HS-Woodland Soccer Field [Directions] | 1:00 p.m. | ||
| Sat., 11/11 | JV Football | Derby | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:15 p.m. | ||
| Tue., 11/14 | V Girls Soccer | Bacon Academy | Home - Veteran's Stadium-Willow Brook Park-New Britain HS [Directions] | 7:00 p.m. | ||
| Wed., 11/15 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/18 | JV Football | Seymour | Away - Seymour HS-turf field [Directions] | 10:00 a.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Wed., 11/22 | V Football | Seymour | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | L 14-34 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Thu., 11/30 | V Girls Basketball | Shepaug Valley (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 12/2 | V Wrestling | Shelton (Scrim.) | Home - Amity Regional HS-Amity HS [Directions] | 10:15 a.m. | ||
| Sat., 12/2 | V Girls Basketball | Wolcott Jamboree @ Wolcott HS | Away - Wolcott HS-gym | 8:30 a.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Tue., 12/5 | V Boys Basketball | Sheehan (Scrim.) | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 12/5 | V Girls Basketball | Thomaston (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/7 | V Girls Basketball | Bristol Central (Scrim.) | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 12/9 | V Boys Basketball | O'Brien Tech (Scrim.) | Home - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Mon., 12/11 | V Boys Basketball | North Haven (Scrim.) | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Mon., 12/11 | V Boys Indoor Track | @ Wesleyan University | Away - Not Listed-Wesleyan University | 4:30 p.m. | ||
| Mon., 12/11 | V Girls Indoor Track | @ Wesleyan University | Away - Not Listed-Wesleyan University | TBA | ||
| Tue., 12/12 | V Girls Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | L 44-65 | |
| Tue., 12/12 | JV Girls Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/14 | V Boys Indoor Track | GHS Indoor Track Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Thu., 12/14 | V Girls Indoor Track | GHS Indoor Track and Field Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Fri., 12/15 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 59-63 | |
| Fri., 12/15 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/15 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/15 | V Girls Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 6:15 p.m. | L 45-56 | |
| Fri., 12/15 | JV Girls Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Sat., 12/16 | V Boys Indoor Track | @ Bethel HS | Away - Not Listed-Bethel HS | 2:00 p.m. | ||
| Sat., 12/16 | V Wrestling | Guilford Wrestling Invitational | Away - Guilford HS-Main gym at GHS | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Indoor Track | @ Bethel HS | Away - Not Listed-Bethel HS | 2:00 p.m. | ||
| Tue., 12/19 | V Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 46-49 | |
| Tue., 12/19 | JV Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Tue., 12/19 | FR Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | Postponed | ||
| Tue., 12/19 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | L 39-43 | |
| Tue., 12/19 | JV Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:15 p.m. | ||
| Wed., 12/20 | V Boys Indoor Track | GHS Indoor Track Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Wed., 12/20 | V Wrestling | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 12/20 | V Girls Indoor Track | GHS Indoor Track and Field Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Thu., 12/21 | V Boys Swimming and Diving | Northwestern | Home - Woodland HS-pool [Directions] | 4:30 p.m. | Win: 94-84 (1-0) | |
| Thu., 12/21 | V Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 46-43 | |
| Thu., 12/21 | JV Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/22 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 58-78 | |
| Fri., 12/22 | JV Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/22 | FR Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 12/22 | JV Wrestling | Foran | Home - Amity Regional HS-Aux. Gym [Directions] | 3:30 p.m. | ||
| Fri., 12/22 | FR Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 1:30 p.m. | ||
| Wed., 12/27 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 12:00 p.m. | W 104-67 | |
| Wed., 12/27 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 10:30 a.m. | ||
| Wed., 12/27 | FR Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/27 | V Wrestling | Cheshire, Morgan | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/27 | V Wrestling | Morgan | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/27 | V Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 12:00 p.m. | W 49-46 | |
| Wed., 12/27 | JV Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Fri., 12/29 | V Boys Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 1:30 p.m. | L 63-108 | |
| Fri., 12/29 | JV Boys Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 12:00 p.m. | ||
| Fri., 12/29 | FR Boys Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Fri., 12/29 | V Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 12:30 p.m. | W 43-41 | |
| Fri., 12/29 | JV Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/30 | V Wrestling | Trumbull Duals | Away - Trumbull HS-McDougall Stadium | 9:00 a.m. | ||
| Wed., 1/3 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 7:00 p.m. | L 55-59 (OT) | |
| Wed., 1/3 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/3 | V Wrestling | North Haven | Away - North Haven MS-Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Derby | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | W 68-39 | |
| Fri., 1/5 | V Boys Basketball | Watertown | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 70-52 | |
| Fri., 1/5 | JV Boys Basketball | Watertown | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Watertown | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Amity, Wilby/Kaynor | Home - Woodland HS-pool [Directions] | 5:00 p.m. | WRHS: 55 - Wilby: 15 & WRHS: 91 - Amity: 92 (2-1, 1-0 in NVL) | |
| Fri., 1/5 | V Girls Basketball | Watertown | Away - Watertown HS [Directions] | 6:00 p.m. | L 51-56 | |
| Fri., 1/5 | JV Girls Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/6 | V Wrestling | Amity Duals | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 9:00 a.m. | 2 or 3 mats | |
| Sat., 1/6 | FR Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Mon., 1/8 | V Boys Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 55-71 | |
| Mon., 1/8 | JV Boys Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:00 p.m. | W 60-44 | |
| Tue., 1/9 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | Postponed | ||
| Wed., 1/10 | V Boys Basketball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 6:00 p.m. | L 57-61 | |
| Wed., 1/10 | JV Boys Basketball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 1/10 | V Boys Swimming and Diving | Notre Dame-West Haven | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 98-86 (3-1, 1-0 in NVL) | |
| Wed., 1/10 | V Wrestling | Daniel Hand | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/10 | JV Wrestling | Daniel Hand | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/10 | FR Girls Basketball | Shelton | Home - Woodland HS-Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/11 | FR Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Thu., 1/11 | V Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | W 53-47 | |
| Thu., 1/11 | JV Girls Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 63-52 | |
| Fri., 1/12 | JV Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Fri., 1/12 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 6:00 p.m. | Win: 92-86 (4-1, 2-0 in NVL) | |
| Sat., 1/13 | V Wrestling | Bunnell, Canton, Notre Dame-Fairfield, Wilton | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 1/13 | FR Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Wed., 1/17 | V Boys Basketball | Seymour | Away - Seymour MS-Gymnasium [Directions] | 7:00 p.m. | L 47-57 | |
| Wed., 1/17 | JV Boys Basketball | Seymour | Away - Seymour MS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Seymour | Away - Seymour MS-Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 1/17 | V Boys Indoor Track | Old Saybrook Qualifier @ Floyd Little | Away - Not Listed-Floyd Little Athletic Center - Hillhouse | 5:00 p.m. | ||
| Wed., 1/17 | V Wrestling | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 46-41 | |
| Wed., 1/17 | JV Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Wed., 1/17 | V Girls Indoor Track | Old Saybrook Qualifier @ Floyd Little | Away - Not Listed-Floyd Little Athletic Center - Hillhouse | 5:00 p.m. | ||
| Thu., 1/18 | V Boys Indoor Track | GHS Indoor Track Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Thu., 1/18 | V Girls Indoor Track | GHS Indoor Track and Field Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 54-57 | |
| Fri., 1/19 | JV Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | Win: 92-67 (5-1, 3-0 in NVL) | |
| Fri., 1/19 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 45-75 | |
| Fri., 1/19 | JV Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 1/20 | V Wrestling | Rockville JV Wrestling Tournament | Away - Rockville HS-Main gymnasium | 10:00 a.m. | ||
| Sat., 1/20 | V Wrestling | New Milford, Bethel, Bunnell, Enfield, Joel Barlow, Maloney, Masuk, Norwalk, Pomperaug Coop, RHAM, Stratford, Terryville-Thomaston, Harding/Bassick/Bridgeport Central, Weston | Away - New Milford HS-Main Gym - NMHS | 9:00 a.m. | ||
| Sat., 1/20 | FR Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/20 | Miscellaneous Events | Dance Competition (Dancing in the Woods) | Home - Woodland HS-Gym [Directions] | 9:00 a.m. | ||
| Mon., 1/22 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:30 p.m. | ||
| Mon., 1/22 | V Boys Indoor Track | Joe Sinicrope Invitational @ Floyd Little Athletic Center | Away - Not Listed-Floyd Little Athletic Center - Hillhouse | 5:00 p.m. | ||
| Mon., 1/22 | V Girls Basketball | WCA | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 43-46 | |
| Mon., 1/22 | JV Girls Basketball | WCA | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Mon., 1/22 | V Girls Indoor Track | Joe Sinicrope Invitational @ Floyd Little Athletic Center | Away - Not Listed-Floyd Little Athletic Center - Hillhouse | 5:00 p.m. | ||
| Tue., 1/23 | JV Wrestling | Guilford | Home - Amity Regional HS-Aux. Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/24 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | W 73-70 | |
| Wed., 1/24 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/24 | V Girls Basketball | Pomperaug | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | L 45-56 | |
| Wed., 1/24 | JV Girls Basketball | Pomperaug | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 61-50 | |
| Fri., 1/26 | JV Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Fri., 1/26 | V Boys Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Crosby/WCA, Kennedy | Home - Woodland HS-pool [Directions] | 5:15 p.m. | Win: 70-32; Win 68-53 (7-1, 5-0 in NVL) | |
| Fri., 1/26 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 59-61 | |
| Fri., 1/26 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | V Girls Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Sat., 1/27 | FR Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/27 | V Wrestling | 2024 Gary Tiger Ridgefield Challenge | Away - Ridgefield HS-Main Gym | 9:00 a.m. | ||
| Sat., 1/27 | FR Girls Basketball | Pomperaug | Home - Woodland HS-Gym [Directions] | 11:45 a.m. | ||
| Mon., 1/29 | V Boys Basketball | Kaynor Tech | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 73-46 | |
| Mon., 1/29 | JV Boys Basketball | Kaynor Tech | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Mon., 1/29 | FR Boys Basketball | Kaynor Tech | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Seymour | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 87-77 (8-1, 6-0 in NVL) | |
| Wed., 1/31 | V Wrestling | Branford | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/31 | JV Wrestling | Branford | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/31 | V Girls Basketball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 49-57 | |
| Wed., 1/31 | JV Girls Basketball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Thu., 2/1 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | ||
| Fri., 2/2 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | L 59-113 | |
| Fri., 2/2 | JV Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win: 105-73 (9-1, 7-0 in NVL) | |
| Fri., 2/2 | V Girls Basketball | Crosby | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 55-10 | |
| Fri., 2/2 | JV Girls Basketball | Crosby | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/3 | FR Boys Basketball | Amity | Home - Woodland HS-Gym [Directions] | 12:15 p.m. | ||
| Sat., 2/3 | V Boys Swimming and Diving | Hall, Amity, Conard, East Lyme NFA, Glastonbury, Oxford, Pomperaug, Southington, Xavier | Away - Cornerstone Aquatics Center-Pool | 3:00 p.m. | ||
| Sat., 2/3 | V Wrestling | Foran Duals | Away - Foran HS -Edna L. Fraser Gymnasium | 9:00 a.m. | ||
| Sat., 2/3 | FR Girls Basketball | Cheshire | Home - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Mon., 2/5 | V Wrestling | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 6:30 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 65-49 | |
| Tue., 2/6 | JV Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 49-53 | |
| Tue., 2/6 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 4:15 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Thu., 2/8 | V Boys Swimming and Diving | Holy Cross | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Dive Only, for 2/9 meet | |
| Thu., 2/8 | Miscellaneous Events | NVL DANCE COMPETITION | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 58-71 | |
| Fri., 2/9 | JV Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | V Boys Indoor Track | CIAC S Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS (Waterbury) [Directions] | 4:00 p.m. | Loss: 89-97 (9-2; 7-1 in NVL) | |
| Fri., 2/9 | V Girls Indoor Track | CIAC S Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 47-36 | |
| Mon., 2/12 | JV Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/14 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/14 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/15 | V Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | W 89-50 | |
| Thu., 2/15 | JV Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/15 | FR Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/15 | V Girls Basketball | WCA | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/16 | V Boys Swimming and Diving | Oxford | Home - Woodland HS-pool [Directions] | 3:00 p.m. | Win: 93-85 (10-2; 8-1 in NVL) | |
| Fri., 2/16 | V Wrestling | CIAC L Divisional Championship | Away - Wilton | TBA | ||
| Fri., 2/16 | V Wrestling | CIAC S Divisional Championship | Away - Killingly | TBA | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Basketball | Holy Cross | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:15 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Tue., 2/20 | V Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 59-53 | |
| Tue., 2/20 | JV Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/20 | FR Boys Basketball | Watertown | Away - Watertown HS [Directions] | 3:30 p.m. | ||
| Fri., 2/23 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:45 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Basketball | WCA | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:15 p.m. | ||
| Mon., 2/26 | V Girls Basketball | Stonington | Away - Stonington HS-SHS Main Gym [Directions] | 6:00 p.m. | W 39-23 | |
| Thu., 2/29 | V Girls Basketball | Windham | Away - Windham HS-Callahan Gymnasium [Directions] | 6:30 p.m. | L 35-52 | |
| Fri., 3/1 | V Boys Basketball | Seymour (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | Crosby/WCA, Holy Cross, Kennedy, Naugatuck, Oxford, Seymour, Torrington, Watertown, Wilby/Kaynor | Home - John F. Kennedy HS-JFK Pool [Directions] | 4:00 p.m. | 1st Place Team: NVL Champions | |
| Mon., 3/4 | V Boys Basketball | Innovation | Away - Innovation-Gymnasium [Directions] | 6:30 p.m. | L 49-70 | |
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 5:15 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Fri., 3/22 | V Baseball | Nonnewaug (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 3/22 | V Baseball | Bristol Central (Scrim.) | Home - Amity Regional HS-Amity HS [Directions] | 4:25 p.m. | ||
| Fri., 3/22 | V Baseball | Bristol Central (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 4:25 p.m. | Cancelled | |
| Fri., 3/22 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 5:20 p.m. | ||
| Fri., 3/22 | JV Baseball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | ||
| Fri., 3/22 | V Softball | Trumbull (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 3/25 | V Baseball | North Branford (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Softball | Cheshire (Scrim.) | Away - Cheshire HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 3/26 | V Baseball | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Baseball | West Haven (Scrim.) | Away - West Haven HS-Whitey Piurek Field [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Softball | Bristol Eastern (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Baseball | Xavier (Scrim.) | Away - Xavier HS-Richard Magner Field [Directions] | Canceled | Cancelled | |
| Thu., 3/28 | V Softball | St. Joseph (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Sat., 3/30 | V Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | W 3-1 | |
| Sat., 3/30 | FR Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 1:30 p.m. | ||
| Sat., 3/30 | V Boys Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | 11:00 a.m. | L 3-2 | |
| Sat., 3/30 | V Softball | Holy Cross | Home - Woodland HS-Softball Diamond [Directions] | 12:00 p.m. | W 26-0 | |
| Sat., 3/30 | V Girls Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 11:00 a.m. | ||
| Mon., 4/1 | V Baseball | Watertown | Away - Deland Field-Deland field [Directions] | 3:45 p.m. | ||
| Mon., 4/1 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 3-2 | |
| Mon., 4/1 | V Softball | Watertown | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | L 1-3 | |
| Mon., 4/1 | V Girls Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | JV Baseball | Watertown | Home - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 4/5 | V Baseball | Ansonia | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Fri., 4/5 | V Girls Tennis | Ansonia | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Sat., 4/6 | V Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | JV Baseball | Masuk | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Mon., 4/8 | V Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 4/8 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:15 p.m. | W 5-0 | |
| Mon., 4/8 | V Softball | Wilby | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | W 22-0 | |
| Mon., 4/8 | V Girls Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 4/9 | JV Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Tue., 4/9 | V Boys Golf | Oxford | Away - Oxford Greens [Directions] | 2:45 p.m. | ||
| Tue., 4/9 | V Boys Outdoor Track | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 4/9 | V Girls Outdoor Track | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 4/9 | V Softball | Brookfield | Home - Woodland HS-Softball Diamond [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 4/9 | JV Softball | Shelton | Home - Woodland HS-Softball Diamond [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | V Girls Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Baseball | Crosby | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Boys Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Wed., 4/10 | V Softball | Crosby | Away - Crosby HS-CHS Softball Field #1 [Directions] | 3:30 p.m. | W 28-0 | |
| Wed., 4/10 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | JV Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Thu., 4/11 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Fri., 4/12 | FR Baseball | Wolcott | Away - BAW B Field Salerno-BAW - B Field [Directions] | Postponed | ||
| Sat., 4/13 | JV Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | Postponed | ||
| Mon., 4/15 | V Baseball | Torrington | Home - Woodland HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Mon., 4/15 | V Boys Golf | St. Paul Catholic | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Mon., 4/15 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | ||
| Mon., 4/15 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 3:45 p.m. | W 25-0 | |
| Tue., 4/16 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | ||
| Tue., 4/16 | V Boys Outdoor Track | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 3:30 p.m. | ||
| Tue., 4/16 | V Girls Outdoor Track | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 3:30 p.m. | ||
| Tue., 4/16 | V Softball | Wolcott | Home - Woodland HS-Softball Diamond [Directions] | 10:30 a.m. | W 8-3 | |
| Wed., 4/17 | V Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Wed., 4/17 | FR Baseball | Shelton | Away - Shelton HS-Baseball Diamond - N Constitution Blvd [Directions] | 3:45 p.m. | ||
| Wed., 4/17 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 11:00 a.m. | ||
| Wed., 4/17 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 6:00 p.m. | L 3-7 | |
| Wed., 4/17 | V Girls Tennis | Seymour | Home - Woodland HS-Tennis Courts [Directions] | 11:00 a.m. | ||
| Thu., 4/18 | JV Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | Postponed | ||
| Fri., 4/19 | V Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | 4:45 p.m. | ||
| Fri., 4/19 | FR Baseball | St. Paul Catholic | Away - Page Park -Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | V Softball | Derby | Home - Woodland HS-Softball Diamond [Directions] | 11:00 a.m. | W 23-0 | |
| Fri., 4/19 | JV Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | Postponed | ||
| Fri., 4/19 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Sat., 4/20 | JV Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | Postponed | ||
| Sat., 4/20 | JV Softball | Shelton | Away - Shelton HS-Upper Field [Directions] | Canceled | Cancelled | |
| Mon., 4/22 | V Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 4/22 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 4/22 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 4/22 | V Girls Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | ||
| Tue., 4/23 | JV Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Derby, Kennedy | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Derby, Kennedy | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | JV Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 4/24 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | 2:45 p.m. | ||
| Wed., 4/24 | V Softball | Holy Cross | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | W 11-8 | |
| Wed., 4/24 | JV Softball | Holy Cross | Home - Woodland HS-Softball Diamond [Directions] | 5:45 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | JV Baseball | Wolcott | Away - Wolcott HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Thu., 4/25 | V Boys Golf | Seymour | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | V Softball | Ansonia | Away - Ansonia HS-Softball Diamond [Directions] | 3:45 p.m. | W 19-0 | |
| Fri., 4/26 | V Baseball | Kennedy | Away - Waterville Park-Baseball Field [Directions] | 3:30 p.m. | ||
| Fri., 4/26 | V Boys Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 4/26 | V Boys Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | ||
| Fri., 4/26 | V Softball | Kennedy | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | W 23-1 | |
| Sat., 4/27 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Baseball | Kennedy | Home - Woodland HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Mon., 4/29 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 6:00 p.m. | ||
| Mon., 4/29 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:45 p.m. | ||
| Mon., 4/29 | V Boys Golf | Oxford | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Mon., 4/29 | V Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | W 14-2 | |
| Mon., 4/29 | V Girls Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | JV Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | JV Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | V Baseball | WCA | Away - Municipal Stadium-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Amity | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:00 p.m. | ||
| Wed., 5/1 | V Softball | WCA | Away - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | 3:45 p.m. | W 15-1 | |
| Wed., 5/1 | V Girls Tennis | Naugatuck, Watertown (Scrim.) | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | V Baseball | St. Joseph | Home - Dunkin' Park (Hartford, CT)-Yard Goats [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | ||
| Thu., 5/2 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Fri., 5/3 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 5/3 | V Girls Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Sat., 5/4 | JV Baseball | St. Joseph | Home - Woodland HS-Baseball Diamond [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | FR Baseball | St. Joseph | Home - Woodland HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 5/4 | JV Softball | Cheshire | Away - Derby HS-Payden Park [Directions] | 1:00 p.m. | ||
| Mon., 5/6 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 2:30 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | ||
| Mon., 5/6 | V Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | 4:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Tue., 5/7 | V Baseball | Derby | Away - Payden Park [Directions] | 6:00 p.m. | ||
| Tue., 5/7 | JV Baseball | Derby | Away - Payden Park [Directions] | 3:00 p.m. | ||
| Tue., 5/7 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Holy Cross | Away - Holy Cross-Holy Cross Track [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Holy Cross | Away - Holy Cross-Holy Cross Track [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | JV Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | 4:45 p.m. | ||
| Tue., 5/7 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | JV Baseball | Shelton | Away - Riverview Park - Shelton-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Wolcott | Away - Wolcott HS-Softball Field [Directions] | 5:15 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 5/9 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 5/10 | V Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | FR Baseball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 5/10 | V Boys Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 5/10 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Sat., 5/11 | JV Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 5/11 | V Girls Tennis | NVL Girls Tennis - JV Jamboree | Home - Woodland HS-Tennis Courts [Directions] | 10:00 a.m. | ||
| Mon., 5/13 | V Baseball | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | FR Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Boys Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Tue., 5/14 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | FR Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | 4:45 p.m. | ||
| Tue., 5/14 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | 2:45 p.m. | ||
| Tue., 5/14 | JV Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | 2:00 p.m. | ||
| Wed., 5/15 | V Softball | Pomperaug | Away - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | JV Softball | Pomperaug | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | 2:45 p.m. | ||