| Woodland 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 188 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. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||