| Woodland 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 527 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/25 | V Football | Pomperaug (Scrim.) | Home - Woodland HS-Woodland Football Field [Directions] | 3:30 p.m. | ||
| Sat., 8/28 | V Football | Platt, Lyman Hall, SMSA Coop (Scrim.) | Away - Platt HS-Platt Turf field [Directions] | 9:00 a.m. | ||
| Mon., 8/30 | V Boys Soccer | Greens Farms Academy (Scrim.) | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/2 | V Football | Northwest United (Scrim.) | Away - Nonnewaug HS-football field [Directions] | 6:00 p.m. | ||
| Thu., 9/2 | V Boys Soccer | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | ||
| Thu., 9/2 | V Girls Soccer | Cheshire (Scrim.) | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 9/2 | V Girls Volleyball | Shelton (Scrim.) | Home - Woodland HS-Gym [Directions] | 3:30 p.m. | ||
| Sat., 9/4 | V Girls Soccer | Milford Jamboree | Away - Jonathan Law HS-Lawmen Stadium | 8:30 a.m. | ||
| Sat., 9/4 | V Girls Volleyball | East Haven, Amity, Coginchaug, Haddam-Killingworth, TBA, TBA, Sheehan | Away - East Haven HS-Gym | 9:00 a.m. | ||
| Wed., 9/8 | V Girls Volleyball | Jonathan Law (Scrim.) | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 9/9 | V Boys Soccer | Brookfield | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/9 | V Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | T 1-1 | |
| Fri., 9/10 | V Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 7:00 p.m. | W 38-27 | |
| Fri., 9/10 | JV Boys Soccer | Brookfield | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 9/10 | V Girls Swimming and Diving | Jonathan Law | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 102-82 | |
| Sat., 9/11 | FM Football | Crosby | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | V Boys Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | 11:00 a.m. | W 3-2 | |
| Sat., 9/11 | V Girls Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:00 p.m. | W 4-0 | |
| Mon., 9/13 | JV Boys Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | 5:15 p.m. | W 4-0 | |
| Mon., 9/13 | V Girls Volleyball | Amity | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 9/13 | JV Girls Volleyball | Amity | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | L 0-2 | |
| Mon., 9/13 | FR Girls Volleyball | Amity | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Wolcott | Home - Woodland HS-Track [Directions] | 3:45 p.m. | Woodland 15 Wolcott 45 | |
| Tue., 9/14 | V Boys Soccer | Wolcott | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 8-0 | |
| Tue., 9/14 | V Girls Cross Country | Wolcott | Home - Woodland HS-Track [Directions] | 3:45 p.m. | Woodland 20 Wolcott 39 | |
| Tue., 9/14 | V Girls Soccer | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 6:00 p.m. | W 6-1 | |
| Tue., 9/14 | V Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Tue., 9/14 | JV Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | 3:00 p.m. | W 2-0 | |
| Wed., 9/15 | JV Boys Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | W 6-0 | |
| Wed., 9/15 | JV Girls Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | 5:15 p.m. | ||
| Fri., 9/17 | V Football | Derby | Home - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | W 40-0 | |
| Fri., 9/17 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Ave [Directions] | 3:00 p.m. | W 9-0 | |
| Fri., 9/17 | V Girls Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 6-0 | |
| Fri., 9/17 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby HS-Gil Cyr Natatorium [Directions] | 4:00 p.m. | Win 76-45 | |
| Fri., 9/17 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:30 p.m. | L 0-3 | |
| Fri., 9/17 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | W 2-0 | |
| Sat., 9/18 | V Boys Cross Country | Wilton Invitational | Away - Not Listed | 9:30 a.m. | Woodland Varsity Boys: 5th Place, Small Schools Woodland JV Boys: 6th Place, Small Schools | |
| Sat., 9/18 | JV Football | Watertown | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:30 a.m. | Woodland Girls JV: 4th Place | |
| Sat., 9/18 | FR Girls Volleyball | Holy Cross, Naugatuck, Seymour | Home - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Tue., 9/21 | V Boys Cross Country | Torrington, Kennedy, St. Paul Catholic | Away - Torrington HS-THS Cross Country Course [Directions] | 5:15 p.m. | Woodland 18 St Paul 41 Woodland 16 Torrington 47 Woodland 15, Kennedy 45 | |
| Tue., 9/21 | JV Boys Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:15 p.m. | W 5-0 | |
| Tue., 9/21 | V Girls Cross Country | Torrington, Kennedy, St. Paul Catholic | Away - Torrington HS-THS Cross Country Course [Directions] | 5:15 p.m. | Woodland 20 St Paul 39 Woodland 15, Kennedy 45 Woodland 15 Torrington 45 | |
| Tue., 9/21 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 95-82 | |
| Tue., 9/21 | V Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:30 p.m. | W 3-1 | |
| Tue., 9/21 | JV Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | W 2-0 | |
| Wed., 9/22 | V Girls Volleyball | East Haven | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 9/22 | JV Girls Volleyball | East Haven | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 9/24 | V Football | Kennedy | Home - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | W 44-6 | |
| Fri., 9/24 | V Girls Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 3:00 p.m. | Win 93-70 | |
| Fri., 9/24 | V Girls Volleyball | Watertown | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/24 | JV Girls Volleyball | Watertown | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | W 2-0 | |
| Sat., 9/25 | FM Football | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | JV Boys Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 9:00 a.m. | W 6-0 | |
| Sat., 9/25 | V Girls Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | 9:30 a.m. | W 3-1 | |
| Sat., 9/25 | JV Girls Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | Postponed | ||
| Sat., 9/25 | FR Girls Volleyball | Naugatuck, St. Paul Catholic, Watertown | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 9/27 | V Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 9/27 | JV Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | W 2-0 | |
| Tue., 9/28 | V Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:30 p.m. | W 8-0 | |
| Tue., 9/28 | V Girls Swimming and Diving | Pomperaug | Home - Woodland HS-pool [Directions] | Postponed | Cacelled | |
| Tue., 9/28 | V Girls Volleyball | Crosby | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Tue., 9/28 | JV Girls Volleyball | Crosby | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | W 2-0 | |
| Wed., 9/29 | V Boys Cross Country | Holy Cross, Naugatuck, Wilby | Away - Holy Cross [Directions] | 3:45 p.m. | Woodland 21, Holy Cross 40 Woodland 15, Wilby 45 Woodland 20, Naugatuck 42 | |
| Wed., 9/29 | JV Boys Soccer | Torrington | Home - Woodland HS-Woodland Soccer Field [Directions] | 4:15 p.m. | W 5-0 | |
| Wed., 9/29 | V Girls Cross Country | Holy Cross, Naugatuck, Wilby | Away - Holy Cross [Directions] | 3:45 p.m. | Woodland 21, Holy Cross 40 Woodland 15, Wilby 45 Woodland 20, Naugatuck 42 | |
| Wed., 9/29 | JV Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | ||
| Thu., 9/30 | V Girls Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 6:00 p.m. | W 9-0 | |
| Thu., 9/30 | V Girls Volleyball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-1 | |
| Thu., 9/30 | JV Girls Volleyball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 10/1 | V Football | Torrington | Home - Woodland HS-Woodland Football Field [Directions] | 6:30 p.m. | L 33-36 | |
| Fri., 10/1 | V Boys Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:00 p.m. | W 8-0 | |
| Fri., 10/1 | V Girls Swimming and Diving | Kennedy | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 73-43 | |
| Sat., 10/2 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:30 a.m. | ||
| Mon., 10/4 | V Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | T 2-2 | |
| Tue., 10/5 | V Boys Cross Country | Watertown, Crosby, Seymour | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:00 p.m. | Woodland 15, Crosby 45 Woodland 15, Seymour 45 Woodland 18, Watertown 42 | |
| Tue., 10/5 | JV Boys Soccer | Naugatuck | Away - Rotary Field-Soccer Field [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 10/5 | V Girls Cross Country | Watertown, Crosby, Seymour | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:00 p.m. | Woodland 21, Seymour 40 Woodland 15, Crosby 45 Woodland 19, Watertown 43 | |
| Tue., 10/5 | JV Girls Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Canceled | Cancelled | |
| Tue., 10/5 | V Girls Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 3:00 p.m. | Win 99-78 | |
| Tue., 10/5 | V Girls Volleyball | Wolcott | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-2 | |
| Tue., 10/5 | JV Girls Volleyball | Wolcott | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | W 2-1 | |
| Wed., 10/6 | V Boys Soccer | Kennedy | Away - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | W 8-0 | |
| Wed., 10/6 | V Girls Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 2-0 | |
| Thu., 10/7 | JV Boys Soccer | Kennedy | Away - West Side MS-Waterbury-Soccer Field [Directions] | 3:30 p.m. | W 8-1 | |
| Thu., 10/7 | V Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Thu., 10/7 | JV Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 10/8 | V Boys Soccer | Torrington | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 10/8 | V Girls Soccer | Holy Cross | Away - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 5:15 p.m. | T 1-1 | |
| Fri., 10/8 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | Win 94-81 | |
| Fri., 10/8 | V Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | W 3-0 | |
| Fri., 10/8 | JV Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | W 11-1 | |
| Sat., 10/9 | V Football | Holy Cross | Away - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 4:30 p.m. | L 28-40 | |
| Mon., 10/11 | JV Girls Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/12 | V Boys Cross Country | Derby, Oxford | Home - Woodland HS-Track [Directions] | 3:15 p.m. | Woodland 15, Oxford 45 Woodland 15, Derby 45 Brass Division Champions | |
| Tue., 10/12 | V Boys Soccer | Wilby | Home - Woodland HS-Woodland Soccer Field [Directions] | 5:00 p.m. | W 6-1 | |
| Tue., 10/12 | V Girls Cross Country | Derby, Oxford | Home - Woodland HS-Track [Directions] | 3:15 p.m. | Woodland 15, Oxford 45 Derby 20, Woodland 35 | |
| Tue., 10/12 | V Girls Swimming and Diving | Suffield | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 89-762 | |
| Tue., 10/12 | V Girls Volleyball | WCA | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Tue., 10/12 | JV Girls Volleyball | WCA | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | W 2-0 | |
| Wed., 10/13 | V Boys Soccer | Holy Cross | Away - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | T 1-1 | |
| Thu., 10/14 | V Girls Volleyball | Kennedy | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 3-1 | |
| Thu., 10/14 | JV Girls Volleyball | Kennedy | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | W 2-0 | |
| Fri., 10/15 | V Boys Soccer | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | W 9-0 | |
| Fri., 10/15 | V Girls Soccer | Wolcott | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 10/15 | V Girls Swimming and Diving | Torrington | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win 85-79 | |
| Fri., 10/15 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/15 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | W 2-0 | |
| Sat., 10/16 | V Girls Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | T 2-2 | |
| Sat., 10/16 | JV Girls Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Canceled | Cancelled | |
| Mon., 10/18 | V Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | W 2-0 | |
| Mon., 10/18 | V Girls Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 3-1 | |
| Mon., 10/18 | V Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 10/18 | JV Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | W 2-0 | |
| Mon., 10/18 | FR Girls Volleyball | Pomperaug | Away - Pomperaug HS-Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Tue., 10/19 | JV Boys Soccer | Oxford | Away - Oxford HS-OHS Soccer Field-West [Directions] | 3:30 p.m. | W 3-0 | |
| Tue., 10/19 | V Girls Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 6:00 p.m. | Win 96-76 | |
| Tue., 10/19 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Tue., 10/19 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 3:00 p.m. | W 2-0 | |
| Wed., 10/20 | V Boys Soccer | WCA | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:45 p.m. | W 3-0 | |
| Wed., 10/20 | V Girls Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/21 | JV Boys Soccer | WCA | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:00 p.m. | W 6-1 | |
| Thu., 10/21 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 10/21 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | L 1-2 | |
| Fri., 10/22 | V Football | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 42-7 | |
| Fri., 10/22 | V Boys Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 2-1 | |
| Fri., 10/22 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | W 6-1 | |
| Fri., 10/22 | V Girls Swimming and Diving | Waterford | Home - Woodland HS-pool [Directions] | 5:00 p.m. | win 94-86 | |
| Sat., 10/23 | FM Football | Oxford | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | JV Girls Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | JV Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | Canceled | Cancelled | |
| Sat., 10/23 | JV Girls Volleyball | East Haven JV Volleyball Invite | Away - East Haven HS-Gym | 8:00 a.m. | ||
| Mon., 10/25 | V Boys Soccer | Seymour | Home - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | W 2-1 | |
| Mon., 10/25 | V Girls Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | W 6-1 | |
| Mon., 10/25 | V Girls Volleyball | Nonnewaug | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 10/25 | JV Girls Volleyball | Nonnewaug | Home - Woodland HS-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Mon., 10/25 | FR Girls Volleyball | Nonnewaug | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Tue., 10/26 | JV Boys Soccer | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Rainout | ||
| Wed., 10/27 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/28 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 6:00 p.m. | W 4-0 | |
| Thu., 10/28 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-Upper Soccer Field [Directions] | Canceled | Cancelled | |
| Thu., 10/28 | V Girls Soccer | St. Paul Catholic | Home - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | W 3-1 | |
| Thu., 10/28 | JV Girls Soccer | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Canceled | Cancelled | |
| Fri., 10/29 | V Football | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 6:30 p.m. | W 44-7 | |
| Sat., 10/30 | FM Football | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 10:00 a.m. | ||
| Sat., 10/30 | V Girls Volleyball | Torrington | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | W 3-2 | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class M Championship | Away - Wickham Park | 9:15 a.m. | ||
| Mon., 11/1 | V Boys Soccer | Torrington | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:00 p.m. | W 1-0 | |
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class SS Championship | Away - Wickham Park | 3:40 p.m. | ||
| Mon., 11/1 | V Girls Soccer | Ansonia | Home - Derby HS-Amendola Field Derby Var [Directions] | 2:00 p.m. | ||
| Tue., 11/2 | V Boys Soccer | Watertown | Home - Torrington HS-Robert Frost Sports Complex [Directions] | 5:30 p.m. | L 1-0 | |
| Tue., 11/2 | V Girls Soccer | St. Paul Catholic | Home - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 7:30 p.m. | ||
| Thu., 11/4 | V Girls Soccer | Holy Cross | Home - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 7:30 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Ansonia | Home - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | L 6-23 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Northwest United | Away - Nonnewaug HS-football field [Directions] | 10:00 a.m. | ||
| Mon., 11/8 | V Girls Volleyball | Sacred Heart Academy | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 11/9 | V Boys Soccer | Windham Tech | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | W 6-1 | |
| Wed., 11/10 | V Girls Soccer | Bacon Academy | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/10 | V Girls Volleyball | Plainville | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 11/11 | V Boys Soccer | Ellington | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | L 3-0 | |
| Fri., 11/12 | V Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 7:00 p.m. | L 13-35 | |
| Fri., 11/12 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 7:00 p.m. | ||
| Sat., 11/13 | FM Football | Naugatuck | Home - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/19 | FM Football | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Wed., 11/24 | V Football | Seymour | Home - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | L 15-22 | |
| Sat., 12/4 | V Girls Basketball | Wethersfield (Scrim.) | Away - Wethersfield HS-Gym A [Directions] | 10:30 a.m. | ||
| Tue., 12/7 | V Girls Basketball | Shepaug Valley (Scrim.) | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/9 | V Boys Basketball | Cheshire (Scrim.) | Away - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Thu., 12/9 | V Girls Basketball | Thomaston, Wolcott (Scrim.) | Away - Thomaston HS-Gym [Directions] | 3:00 p.m. | ||
| Sun., 12/12 | V Boys Basketball | North Haven (Scrim.) | Home - Woodland HS-Gym [Directions] | 12:00 p.m. | ||
| Tue., 12/14 | V Girls Basketball | Watertown | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 56-44 | |
| Tue., 12/14 | JV Girls Basketball | Watertown | Home - Woodland HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/15 | V Wrestling | Cheshire | Away - Cheshire HS-Gym - East [Directions] | Postponed | ||
| Thu., 12/16 | V Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 56-81 | |
| Thu., 12/16 | JV Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | FR Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 12/16 | V Girls Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 60-14 | |
| Thu., 12/16 | JV Girls Basketball | Wilby | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 12/17 | V Boys Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 4:00 p.m. | Loss: 96-84 (Non-League) (0-1) | |
| Sat., 12/18 | FR Boys Basketball | Seymour, Torrington | Away - Seymour HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/18 | V Wrestling | Guilford Invitational | Away - Guilford HS-Main gym at GHS | 9:00 a.m. | ||
| Tue., 12/21 | V Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | L 60-46 | |
| Tue., 12/21 | JV Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Tue., 12/21 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:30 p.m. | W 56-41 | |
| Tue., 12/21 | JV Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/22 | V Wrestling | Morgan | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | Postponed | ||
| Thu., 12/23 | V Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 53-44 | |
| Thu., 12/23 | JV Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/23 | V Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 7:00 p.m. | W 47-46 | |
| Thu., 12/23 | JV Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 12/27 | V Boys Basketball | Seymour | Away - Litchfield HS-Gym [Directions] | 5:00 p.m. | W 58-47 | |
| Tue., 12/28 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 6:25 p.m. | W 49-46 | |
| Tue., 12/28 | V Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | W 47-43(OT) | |
| Tue., 12/28 | JV Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 12/30 | V Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | L 65-57 | |
| Thu., 12/30 | JV Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/30 | FR Boys Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Thu., 12/30 | V Wrestling | Shelton, Masuk | Away - Shelton HS-Auxillary Gym [Directions] | 9:00 a.m. | ||
| Thu., 12/30 | V Wrestling | Trumbull Duals | Away - Trumbull HS-THS Main Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Thu., 12/30 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | L 31-66 | |
| Thu., 12/30 | JV Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 1/7 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS-CHS Pool [Directions] | 6:00 p.m. | Cancelled | |
| Sat., 1/8 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 1/8 | V Wrestling | Bethel, Newington, New Haven Wrestling | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 9:30 a.m. | 2 mats | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Tue., 1/11 | V Boys Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | L 41-49 | |
| Tue., 1/11 | JV Boys Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/11 | FR Boys Basketball | Torrington | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/11 | V Boys Swimming and Diving | Crosby/WCA, Seymour | Home - Woodland HS-pool [Directions] | 6:15 p.m. | Woodland: 51 - Seymour: 33 Woodland: 51 - Crosby: 17 (2-1) | |
| Tue., 1/11 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 41-52 | |
| Tue., 1/11 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/12 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 51-82 | |
| Wed., 1/12 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/12 | V Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | L 44-54(OT) | |
| Wed., 1/12 | JV Girls Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/14 | V Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 74-70 | |
| Fri., 1/14 | JV Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/14 | V Boys Swimming and Diving | Shelton | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win: 95-65 (Non-League) (3-1) | |
| Fri., 1/14 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | L 29-60 | |
| Fri., 1/14 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/15 | V Wrestling | Platt, Brien McMahon, Cheshire | Away - Platt HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/15 | Winter Dance Team | Norwich Free Academy | Home - Woodland HS-Gym [Directions] | 2:30 p.m. | ||
| Sat., 1/15 | Winter Dance Team | Wolcott | Home - Woodland HS-Gym [Directions] | 2:00 p.m. | ||
| Mon., 1/17 | JV Wrestling | Notre Dame-West Haven | Away - Notre Dame HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/18 | V Boys Basketball | Crosby | Home - Woodland HS-Gym [Directions] | 7:00 p.m. | L 71-46 | |
| Tue., 1/18 | JV Boys Basketball | Crosby | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/18 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | W 65-40 | |
| Tue., 1/18 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:30 p.m. | ||
| Wed., 1/19 | V Boys Basketball | Kaynor Tech | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 66-48 | |
| Wed., 1/19 | JV Boys Basketball | Kaynor Tech | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/19 | V Wrestling | Daniel Hand, Morgan | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/19 | JV Wrestling | Daniel Hand | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/19 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 6:00 p.m. | W 54 - 27 | |
| Fri., 1/21 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 5:30 p.m. | Win: 94-87 (4-1) | |
| Sat., 1/22 | FR Boys Basketball | Torrington | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/22 | FR Boys Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/22 | V Wrestling | The 35th Annual New Milford Wrestling Tournament | Away - New Milford HS-Main Gym - NMHS | 8:30 a.m. | ||
| Mon., 1/24 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 7:00 p.m. | W 52-49 | |
| Mon., 1/24 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/24 | V Wrestling | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 6:30 p.m. | ||
| Tue., 1/25 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 59-78 | |
| Tue., 1/25 | JV Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 45-23 | |
| Tue., 1/25 | JV Girls Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/26 | FR Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 1/26 | V Wrestling | Xavier | Away - Xavier HS-Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/26 | V Girls Basketball | Harding | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | W 56-21 | |
| Wed., 1/26 | JV Girls Basketball | Harding | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/28 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | L 67-71(OT) | |
| Fri., 1/28 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | Postponed | ||
| Fri., 1/28 | V Boys Swimming and Diving | Watertown | Home - Woodland HS-pool [Directions] | 5:30 p.m. | Win: 93 - 70 (5-1) | |
| Fri., 1/28 | V Girls Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | W 63-58 OT | |
| Fri., 1/28 | JV Girls Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | Postponed | ||
| Sat., 1/29 | FR Boys Basketball | Freshmen Basketball Jamboree | Away - TBA | 9:00 a.m. | ||
| Sat., 1/29 | FR Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/29 | V Wrestling | Fitch, Foran | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 1/31 | FR Boys Basketball | WCA | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Boys Basketball | WCA | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | L 73-60 | |
| Tue., 2/1 | JV Boys Basketball | WCA | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/1 | V Wrestling | Branford | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 2/1 | JV Wrestling | Branford | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 2/1 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | W 57-41 | |
| Tue., 2/1 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/2 | V Wrestling | Foran | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 2/3 | Winter Dance Team | NVL Dance Championship | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 2/5 | FR Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | Postponed | ||
| Sat., 2/5 | FR Boys Basketball | Torrington | Home - Woodland HS-Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/5 | V Girls Basketball | Derby | Home - Woodland HS-Gym [Directions] | 11:30 a.m. | W 52-20 | |
| Tue., 2/8 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:30 p.m. | L 76-82 | |
| Tue., 2/8 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/8 | V Boys Swimming and Diving | Holy Cross | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Loss: 94-92 (5-2) | |
| Tue., 2/8 | V Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | L 48-49 | |
| Tue., 2/8 | JV Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 2/9 | V Wrestling | East Haven | Away - East Haven HS-Gym [Directions] | 6:30 p.m. | ||
| Fri., 2/11 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:30 p.m. | L 52-56 | |
| Fri., 2/11 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | W 56-45 | |
| Fri., 2/11 | JV Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/12 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | V Girls Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 6:45 p.m. | W 78-27 | |
| Tue., 2/15 | JV Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Kennedy | Home - Woodland HS-pool [Directions] | 5:15 p.m. | Win: 98-53 (6-2) | |
| Tue., 2/15 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | W 58-15 | |
| Tue., 2/15 | JV Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/17 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:00 p.m. | Loss (6-3) | |
| Thu., 2/17 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:30 p.m. | W 57-45 | |
| Thu., 2/17 | JV Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | V Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 5:00 p.m. | L 67-78 | |
| Fri., 2/18 | JV Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Fri., 2/18 | V Boys Swimming and Diving | Oxford | Home - Woodland HS-pool [Directions] | 3:30 p.m. | ||
| Fri., 2/18 | V Wrestling | Class LL Championship - Day 1 | Away - Trumbull | 1:45 p.m. | ||
| Fri., 2/18 | V Wrestling | Class S Championship - Day 1 | Away - Killingly | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class S Championship - Day 2 | Away - Killingly | 9:00 a.m. | ||
| Sat., 2/19 | V Wrestling | Class LL Championship - Day 2 | Away - Trumbull | 12:00 p.m. | ||
| Sat., 2/19 | V Girls Basketball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 2:30 p.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | FR Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:00 p.m. | ||
| Tue., 2/22 | V Girls Basketball | Holy Cross | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:30 p.m. | ||
| Wed., 2/23 | V Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 57-45 | |
| Wed., 2/23 | JV Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/23 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | Win (7-3) | |
| Sat., 2/26 | V Boys Swimming and Diving | Crosby/WCA, Holy Cross, Kennedy, Naugatuck, Oxford, Seymour, Torrington, WCA, Watertown | Home - John F. Kennedy HS-John Reardon Pool [Directions] | 12:00 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Tue., 3/1 | V Girls Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/3 | V Boys Basketball | Sheehan (Scrim.) | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 3/5 | V Boys Swimming and Diving | Crosby/WCA, Holy Cross, Kennedy, Naugatuck, Oxford, Seymour, Torrington, WCA, Watertown | Home - John F. Kennedy HS-John Reardon Pool [Directions] | 11:00 a.m. | NVL Champions - 1st Place | |
| Mon., 3/7 | V Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 4:00 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:30 p.m. | Class S Championship Runner-Up (2nd Place) | |
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | 38th Place | |
| Wed., 3/23 | V Softball | St. Joseph (Scrim.) | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 3/24 | V Baseball | West Haven (Scrim.) | Away - West Haven HS-Whitey Piurek Field [Directions] | 3:30 p.m. | ||
| Fri., 3/25 | V Baseball | North Branford (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | Postponed | ||
| Sat., 3/26 | V Baseball | Gilbert (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | 12:00 p.m. | ||
| Sat., 3/26 | V Baseball | Portland (Scrim.) | Away - Portland HS-Portland HS [Directions] | 1:00 p.m. | Cancelled | |
| Sat., 3/26 | V Softball | Cheshire (Scrim.) | Away - Cheshire HS-Softball Diamond [Directions] | 12:30 p.m. | ||
| Wed., 3/30 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | Masuk (Scrim.) | Away - Masuk HS-Masuk High School Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Baseball | Xavier (Scrim.) | Away - Xavier HS-Richard Magner Field [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Softball | WCA (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 5:15 p.m. | Cancelled | |
| Fri., 4/1 | V Softball | Trumbull (Scrim.) | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 4/2 | FR Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | Postponed | ||
| Sat., 4/2 | JV Softball | Cheshire | Away - Cheshire HS-Softball Diamond 2 [Directions] | 2:30 p.m. | ||
| Sat., 4/2 | V Girls Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | 10:00 a.m. | L 2-5 | |
| Mon., 4/4 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | W 14-5 | |
| Mon., 4/4 | V Boys Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 [Detailed Results] | |
| Mon., 4/4 | V Softball | Torrington | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 4/4 | V Girls Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/5 | JV Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 4/5 | V Boys Outdoor Track | Derby, Naugatuck | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | Naugatuck 96, WRHS 54 WRHS 87, Derby 62 | |
| Tue., 4/5 | V Girls Outdoor Track | Derby, Naugatuck | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | Naugatuck 78, WRHS 72 WRHS 102, Derby 44 | |
| Tue., 4/5 | V Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | 3:00 p.m. | W 11-0 | |
| Tue., 4/5 | JV Softball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Canceled | Cancelled | |
| Fri., 4/8 | V Boys Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | L 2-3 [Detailed Results] | |
| Fri., 4/8 | V Softball | Watertown | Away - Watertown High-Softball Field [Directions] | 4:15 p.m. | W 10-0 | |
| Sat., 4/9 | JV Baseball | Watertown | Home - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 4/11 | V Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | W 24-0 (5) | |
| Mon., 4/11 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:30 p.m. | ||
| Mon., 4/11 | V Boys Golf | Seymour | Home - Oxford Greens [Directions] | 2:00 p.m. | Win-229-245-Norton-49,Barbarito-55, Ianniruberto-60,Sciarretto-65 | |
| Mon., 4/11 | V Softball | Wilby | Home - Woodland HS-Softball Diamond [Directions] | 5:00 p.m. | W 21-0 | |
| Mon., 4/11 | JV Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | 2:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Tue., 4/12 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 3:30 p.m. | W 6-2 | |
| Tue., 4/12 | JV Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 4/12 | V Boys Outdoor Track | O'Brien Tech, Platt Tech, Torrington | Home - Woodland HS-Track [Directions] | 3:30 p.m. | WRHS 104.5, Torrington 44.5 WRHS 122, Platt Tech 27 WRHS 113, O'Brien Tech 35 | |
| Tue., 4/12 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Tue., 4/12 | V Girls Outdoor Track | Platt Tech, Torrington | Home - Woodland HS-Track [Directions] | 3:30 p.m. | WRHS 123, Torrington 27 WRHS136, Platt Tech 11 No Girls from O'Brien Tech | |
| Wed., 4/13 | FR Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 4/13 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | Loss-219-228,Ianniruberto-52,Barbarito-57,Sciarretto-59,Norton-60 | |
| Wed., 4/13 | V Boys Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | Cancelled | |
| Wed., 4/13 | V Softball | Thomaston | Home - Woodland HS-Softball Diamond [Directions] | 4:15 p.m. | W 20-0 | |
| Thu., 4/14 | V Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 3:00 p.m. | W 6-3 | |
| Thu., 4/14 | JV Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 12:00 p.m. | ||
| Thu., 4/14 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-0 [Detailed Results] | |
| Thu., 4/14 | V Girls Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | 1:30 p.m. | L 1-6 | |
| Fri., 4/15 | JV Softball | Wolcott | Away - Wolcott HS-JV Softball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/16 | V Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | 10:00 a.m. | L 7-4 (8) | |
| Sat., 4/16 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 10:00 a.m. | ||
| Sat., 4/16 | V Boys Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | 10:00 a.m. | W 4-1 [Detailed Results] | |
| Sat., 4/16 | V Softball | Wolcott | Away - Wolcott HS-George Babcock Softball Field [Directions] | 10:00 a.m. | W 20-0 | |
| Sat., 4/16 | V Girls Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 10:00 a.m. | L 2-5 | |
| Mon., 4/18 | V Baseball | Derby | Away - Payden Park [Directions] | 4:45 p.m. | W 13-0 (5) | |
| Mon., 4/18 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | W 3-2 [Detailed Results] | |
| Mon., 4/18 | V Softball | Derby | Home - Woodland HS-Softball Diamond [Directions] | 3:45 p.m. | W 24-0 | |
| Mon., 4/18 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Tue., 4/19 | V Boys Outdoor Track | Watertown, Holy Cross | Away - Watertown HS [Directions] | 3:45 p.m. | WRHS 95.5 HCHS 55.5 WRHS 109, Watertown 40 | |
| Tue., 4/19 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 4/19 | V Girls Outdoor Track | Watertown, Holy Cross | Away - Watertown HS [Directions] | 3:45 p.m. | WRHS 136, HCHS 13 WRHS127, Watertown 22 | |
| Tue., 4/19 | JV Softball | Derby | Away - Derby HS-Payden Park [Directions] | Canceled | Cancelled | |
| Wed., 4/20 | V Baseball | Ansonia | Home - Woodland HS-Baseball Diamond [Directions] | 3:00 p.m. | W 10-0 (6) | |
| Wed., 4/20 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | Loss-189-255,Barbarito-55,Sciarretto-65,Ianniruberto-67,Norton-68 | |
| Wed., 4/20 | V Softball | Ansonia | Home - Woodland HS-Softball Diamond [Directions] | 3:00 p.m. | W 26-0 | |
| Thu., 4/21 | JV Baseball | Nonnewaug | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Thu., 4/21 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | Win-216-217,Norton-49,Ianniruberto-53,Barbarito-56,Sciarretto-58 | |
| Thu., 4/21 | V Boys Tennis | Shepaug Valley | Home - Woodland HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-3 [Detailed Results] | |
| Thu., 4/21 | V Softball | Immaculate | Away - Immaculate HS-Softball Diamond [Directions] | 4:30 p.m. | W 7-0 | |
| Fri., 4/22 | V Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | W 1-0 (9) | |
| Fri., 4/22 | FR Baseball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 4/22 | V Boys Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Fri., 4/22 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 4:00 p.m. | W 5-4 | |
| Fri., 4/22 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | W 4-3 | |
| Sat., 4/23 | V Baseball | St. Joseph | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | W 16-13 | |
| Sat., 4/23 | FR Baseball | Wolcott | Away - Wolcott HS-Baseball Diamond [Directions] | 2:00 p.m. | ||
| Sat., 4/23 | V Boys Outdoor Track | Kennedy, WCA | Home - Woodland HS-Track [Directions] | 10:00 a.m. | WRHS 108 WCA 40 WRHS 114 Kennedy 34 WCA 84 Kennedy 56 | |
| Sat., 4/23 | V Girls Outdoor Track | Kennedy, WCA | Home - Woodland HS-Track [Directions] | 10:00 a.m. | WRHS 134, WCA 15 WRHS 127, Kennedy 21 WCA 85, Kennedy 48 | |
| Sat., 4/23 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 11:00 a.m. | ||
| Mon., 4/25 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:00 p.m. | ||
| Mon., 4/25 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 6:00 p.m. | W 9-4 | |
| Mon., 4/25 | FR Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | Postponed | ||
| Mon., 4/25 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 2:00 p.m. | Loss-188-236, Ianniruberto-56, Barbarito-57, Norton-57, Sciarretto-66 | |
| Mon., 4/25 | V Boys Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 [Detailed Results] | |
| Mon., 4/25 | V Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | 3:00 p.m. | W 12-0 | |
| Mon., 4/25 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 3:00 p.m. | W 5-2 | |
| Tue., 4/26 | V Baseball | Watertown | Home - Woodland HS-Baseball Diamond [Directions] | 3:00 p.m. | L 3-2 | |
| Tue., 4/26 | JV Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:00 p.m. | ||
| Tue., 4/26 | JV Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 3:00 p.m. | ||
| Wed., 4/27 | V Baseball | Derby | Home - Woodland HS-Baseball Diamond [Directions] | 4:15 p.m. | W 12-2 (5) | |
| Wed., 4/27 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | 2:00 p.m. | Win-214-234-Ianniruberto-48, Norton-51, Barbarito-54, Sciarretto-61 | |
| Wed., 4/27 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-0 [Detailed Results] | |
| Wed., 4/27 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | 5:30 p.m. | W 16-0 | |
| Wed., 4/27 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 4/28 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Loss-201-232.Barbarito-49, Ianniruberto-58, Norton-62, Sciarretto-63 | |
| Fri., 4/29 | V Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | L 6-0 | |
| Fri., 4/29 | JV Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 3:00 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 4/29 | V Softball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:00 p.m. | W 15-0 | |
| Fri., 4/29 | V Girls Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:00 p.m. | L 2-5 | |
| Sat., 4/30 | JV Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 11:30 a.m. | ||
| Sat., 4/30 | FR Baseball | Holy Cross | Home - Woodland HS-Baseball Diamond [Directions] | 9:30 a.m. | ||
| Tue., 5/3 | V Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | 3:15 p.m. | L 11-8 | |
| Tue., 5/3 | JV Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 5/3 | V Boys Outdoor Track | Crosby, Wolcott | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 2:30 p.m. | WRHS 133, Wolcott 17 WRHS 115, Crosby 35 | |
| Tue., 5/3 | V Boys Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | W 5-0 [Detailed Results] | |
| Tue., 5/3 | V Girls Outdoor Track | Crosby, Wolcott | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 2:30 p.m. | WRHS 129, Wolcott 21 WRHS130, Crosby 20 | |
| Tue., 5/3 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:15 p.m. | W 8-3 | |
| Tue., 5/3 | JV Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | Postponed | ||
| Wed., 5/4 | V Softball | WCA | Home - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | 4:00 p.m. | W 13-0 | |
| Thu., 5/5 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 5/5 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 2:45 p.m. | Loss-173-235. Norton-55,Ianniruberto-59,Sciarretto-60,Barbarito-61 | |
| Thu., 5/5 | V Softball | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 4:30 p.m. | W 17-0 | |
| Thu., 5/5 | V Girls Tennis | Ansonia | Home - Woodland HS-Tennis Courts [Directions] | 4:30 p.m. | W 4-3 | |
| Sat., 5/7 | FR Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | Postponed | ||
| Sat., 5/7 | JV Softball | Cheshire | Home - Woodland HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 5/9 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:00 p.m. | L 5-0 | |
| Mon., 5/9 | FR Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | 4:45 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | W 4-1 [Detailed Results] | |
| Mon., 5/9 | V Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | 5:30 p.m. | W 13-0 | |
| Tue., 5/10 | V Baseball | WCA | Away - Municipal Stadium-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | W 15-0 (5) | |
| Tue., 5/10 | V Boys Outdoor Track | Seymour, Wilby | Home - Woodland HS-Track [Directions] | 5:00 p.m. | WRHS 99, Seymour 47 WRHS 128, Wilby 18 | |
| Tue., 5/10 | V Girls Outdoor Track | Seymour, Wilby | Home - Woodland HS-Track [Directions] | 5:00 p.m. | WRHS 127.5, Seymour 22.5 WRHS 148, Wilby 2 | |
| Tue., 5/10 | JV Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | 4:45 p.m. | ||
| Tue., 5/10 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS-Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Wed., 5/11 | V Baseball | Kennedy | Home - Woodland HS-Baseball Diamond [Directions] | 5:00 p.m. | W 8-1 | |
| Wed., 5/11 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | 2:00 p.m. | Loss-177-229 Barbarito-54, Ianniruberto-54, Norton-58, Sciarretto-63 | |
| Wed., 5/11 | V Boys Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | W 5-0 [Detailed Results] | |
| Wed., 5/11 | V Softball | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 3:45 p.m. | W 13-0 | |
| Wed., 5/11 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/12 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 3:00 p.m. | Cancelled | |
| Thu., 5/12 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/12 | FR Baseball | Kennedy | Home - Woodland HS-Baseball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 5/12 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | 2:00 p.m. | Win 221-230. Norton-54, Sciarretto-55,Barbarito-56,Ianniruberto-56 | |
| Thu., 5/12 | JV Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | 3:00 p.m. | ||
| Fri., 5/13 | V Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | 3:00 p.m. | W 5-4 | |
| Fri., 5/13 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 6:30 p.m. | W 20-0 | |
| Fri., 5/13 | V Girls Tennis | Seymour | Home - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Sat., 5/14 | JV Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Sat., 5/14 | JV Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 10:00 a.m. | ||
| Mon., 5/16 | V Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 2:45 p.m. | W 18-3 (5) | |
| Mon., 5/16 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Loss-186-248. Ianniruberto-56, Barbarito-59, Norton-63, Sciarretto-70 | |
| Mon., 5/16 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | Cancelled | |
| Mon., 5/16 | V Girls Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | 1:45 p.m. | W 7-0 | |
| Tue., 5/17 | JV Baseball | Nonnewaug | Home - Woodland HS-Baseball Diamond [Directions] | 3:15 p.m. | ||
| Tue., 5/17 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | Loss-210-215, Ianniruberto-48,Barbarito-51, Norton-51, Sciarretto-65 | |
| Tue., 5/17 | V Boys Outdoor Track | Oxford, Platt Tech, St. Paul Catholic | Home - Woodland HS-Track [Directions] | 4:30 p.m. | WRHS 123 Oxford 27 WRHS 122 St Paul 28 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:45 p.m. | ||||||
| Tue., 5/17 | V Boys Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | 2:30 p.m. | W 5-0 | |
| Tue., 5/17 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 5/17 | V Girls Outdoor Track | Oxford, Platt Tech, St. Paul Catholic | Home - Woodland HS-Track [Directions] | 4:30 p.m. | WRHS 121 Oxford 27 WRHS 131 St Paul 18 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:45 p.m. | ||||||
| Tue., 5/17 | V Girls Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Wed., 5/18 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | 2:00 p.m. | Win - 231 - 235 Norton-52, Ianniruberto-55, Barbarito-62, Sciarretto-62 | |
| Wed., 5/18 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | W 5-0 | |
| Wed., 5/18 | V Softball | Crosby | Home - Woodland HS-Softball Diamond [Directions] | 5:00 p.m. | W 23-0 | |
| Wed., 5/18 | V Girls Tennis | Ansonia | Home - Woodland HS-Tennis Courts [Directions] | 2:45 p.m. | ||
| Thu., 5/19 | JV Baseball | Wolcott | Home - Woodland HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | V Boys Golf | Shelton | Away - Brownson Country Club [Directions] | 2:45 p.m. | ||
| Fri., 5/20 | V Girls Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 2:00 p.m. | ||
| Sat., 5/21 | V Baseball | Naugatuck | Home - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | W 4-0 | |
| Sat., 5/21 | V Softball | Torrington | Home - Woodland HS-Softball Diamond [Directions] | 12:00 p.m. | ||
| Mon., 5/23 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | 1:45 p.m. | ||
| Mon., 5/23 | V Softball | Naugatuck | Home - Wolcott HS-George Babcock Softball Field [Directions] | 7:00 p.m. | ||
| Mon., 5/23 | V Girls Tennis | NVL Girls Tennis Individual Tournament | Home - Woodland HS-Tennis Courts [Directions] | 12:00 p.m. | ||
| Tue., 5/24 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | 2:00 p.m. | ||
| Wed., 5/25 | V Baseball | St. Paul Catholic | Away - Municipal Stadium-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 7:00 p.m. | W 6-4 | |
| Wed., 5/25 | V Softball | Oxford | Home - Seymour HS-Softball Diamond [Directions] | 7:00 p.m. | ||
| Fri., 5/27 | V Girls Tennis | Plainville | Home - Woodland HS-Tennis Courts [Directions] | 2:00 p.m. | ||
| Sun., 5/29 | V Softball | Masuk (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 12:00 p.m. | ||
| Tue., 5/31 | V Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Tennis | Immaculate | Home - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | W 6-1 | |
| Tue., 5/31 | V Girls Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Wed., 6/1 | V Baseball | Grasso Tech | Home - Woodland HS-Baseball Diamond [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Boys Tennis | Shepaug Valley | Home - Woodland HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Softball | Plainville | Home - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | W 15-1 | |
| Thu., 6/2 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Thu., 6/2 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Fri., 6/3 | V Softball | Wolcott | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 6/3 | V Softball | Wolcott | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 6/4 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Mon., 6/6 | V Boys Golf | CIAC Division II Spring Championship | Away - Tallwood CC | 7:30 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Baseball | Jonathan Law | Home - Muzzy Field-Baseball Diamond [Directions] | 7:00 p.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Softball | Watertown | Home - DeLuca Field-Deluca Field [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Baseball | Joel Barlow | Away - Palmer Field-Baseball Diamond [Directions] | 7:00 p.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/11 | V Softball | Oxford | Home - DeLuca Field-Deluca Field [Directions] | 12:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||