| Woodland 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 546 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | V Baseball | Wilbur Cross (Scrim.) | Home - Woodland High School Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Naugatuck | Away - Rotary Field [Directions] | TBA | 2:20 p.m. | |
| TBA | JV Baseball | Oxford | Home - Woodland High School Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Derby | Away - Derby -Ryan Athletic Complex-baseball field [Directions] | TBA | 2:20 p.m. | |
| TBA | JV Baseball | Sacred Heart | Home - Woodland High School Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 8:30 a.m. | |
| TBA | FR Baseball | Naugatuck | Away - Rotary Field [Directions] | TBA | 2:20 p.m. | |
| TBA | FR Baseball | Sacred Heart | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 2:20 p.m. | |
| TBA | JV Football | Seymour | Away - Seymour High Lower Field [Directions] | Cancelled | ||
| TBA | V Boys Soccer | Seymour (Scrim.) | Away - Seymour High Main Field [Directions] | TBA | ||
| TBA | V Wrestling | Jonathan Law | Home - Amity High School [Directions] | 6:30 p.m. | ||
| TBA | JV Girls Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | TBA | ||
| TBA | V Softball | Nonnewaug (Scrim.) | Home - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| TBA | JV Softball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Kennedy | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| Thu., 1/9 | FR Girls Basketball | Sacred Heart | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Wed., 8/27 | V Football | Oxford (Scrim.) | Home - Woodland Football Field [Directions] | 3:30 p.m. | ||
| Fri., 8/29 | V Girls Volleyball | Shelton (Scrim.) | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Fri., 8/29 | JV Girls Volleyball | Shelton (Scrim.) | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Sat., 8/30 | V Football | North Haven (Scrim.) | Away - North Haven High School [Directions] | 10:00 a.m. | 8:30 a.m. | |
| Sat., 8/30 | V Girls Volleyball | East Haven Jamboree | Away - east haven high school | 9:00 a.m. | 8:00 a.m. | |
| Tue., 9/2 | V Girls Volleyball | Cheshire (Scrim.) | Home - Woodland High School Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/2 | JV Girls Volleyball | Cheshire (Scrim.) | Home - Woodland High School Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/3 | V Girls Soccer | Pomperaug (Scrim.) | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Thu., 9/4 | V Boys Soccer | New Fairfield (Scrim.) | Home - Woodland Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/4 | V Girls Soccer | Litchfield (Scrim.) | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | 2:45 p.m. | |
| Thu., 9/4 | V Girls Volleyball | Joel Barlow (Scrim.) | Away - Lower Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 9/4 | JV Girls Volleyball | Joel Barlow (Scrim.) | Away - Lower Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/5 | V Football | Bristol Eastern (Scrim.) | Away - Bristol Eastern HIgh School [Directions] | 3:30 p.m. | 2:15 p.m. | |
| Fri., 9/5 | V Girls Swimming and Diving | NVL Indicational | Away - Kennedy High School | 4:00 p.m. | 2:15 | |
| Sat., 9/6 | V Boys Cross Country | West Haven Beach Run | Away | TBA | TBA | |
| Sat., 9/6 | V Boys Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 10:00 a.m. | 8:30 a.m. | |
| Sat., 9/6 | V Girls Volleyball | Blast at the Beach | Away - West Haven Beach | TBA | TBA | |
| Tue., 9/9 | V Boys Cross Country | Bullard Havens Tech, Abbott Tech | Away - WOOSTER CEMETERY, DANBURY [Directions] | 3:30 p.m. | 2:15 P.M. | |
| Tue., 9/9 | V Boys Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | L 1-4 | ||
| Tue., 9/9 | V Girls Soccer | Naugatuck | Away - Naugatuck High School [Directions] | W 2-1 | 4:45 p.m. | |
| Tue., 9/9 | V Girls Volleyball | Naugatuck | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Tue., 9/9 | JV Girls Volleyball | Naugatuck | Home - Woodland High School Gym [Directions] | W 2-1 | ||
| Wed., 9/10 | FR Football | Watertown | Home - Woodland Football Field [Directions] | 3:30 p.m. | ||
| Wed., 9/10 | JV Boys Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 9/10 | JV Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:30 p.m. | 2:30 | |
| Wed., 9/10 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Home - Woodland High School Pool [Directions] | Win | ||
| Thu., 9/11 | V Boys Soccer | Holy Cross | Home - Woodland Soccer Field [Directions] | L 1-6 | ||
| Thu., 9/11 | V Girls Soccer | Holy Cross | Away - Holy Cross HS [Directions] | L 0-1 | 2:30 p.m. | |
| Thu., 9/11 | V Girls Volleyball | Torrington | Away - Torrington High School [Directions] | W 3-2 | 3:30 p.m. | |
| Thu., 9/11 | JV Girls Volleyball | Torrington | Away - Torrington High School [Directions] | L 1-2 | 3:30 p.m. | |
| Fri., 9/12 | V Football | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | W 24-0 | 4:00 p.m. | |
| Fri., 9/12 | JV Boys Soccer | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 9/12 | JV Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 9/12 | V Girls Swimming and Diving | East Haven/Cross/Hillhouse/SHA | Home - Woodland High School Pool [Directions] | Win | ||
| Fri., 9/12 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | L 0-3 | 3:30 p.m. | |
| Fri., 9/12 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | L 0-2 | 3:30 p.m. | |
| Sat., 9/13 | V Boys Cross Country | Wilton Invitational | Away - Wilton High School | TBA | 7:15 a.m. | |
| Sat., 9/13 | JV Football | Watertown | Home - Woodland Football Field [Directions] | 10:30 a.m. | ||
| Mon., 9/15 | V Boys Soccer | International | Home - Woodland Soccer Field [Directions] | W 6-2 | ||
| Tue., 9/16 | V Boys Cross Country | Kennedy, Oxford, Holy Cross, Wolcott | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Tue., 9/16 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | L 1-6 | 2:30 p.m. | |
| Tue., 9/16 | V Girls Soccer | Watertown | Home - Woodland Soccer Field [Directions] | L 0-1 | ||
| Tue., 9/16 | V Girls Swimming and Diving | Holy Cross | Home - Woodland High School Pool [Directions] | Win | ||
| Tue., 9/16 | V Girls Volleyball | Nonnewaug | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Tue., 9/16 | JV Girls Volleyball | Nonnewaug | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Wed., 9/17 | JV Boys Soccer | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 9/17 | V Girls Soccer | International/AAE | Away - MLC [Directions] | W 8-0 | 2:30 p.m. | |
| Wed., 9/17 | V Girls Volleyball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Wed., 9/17 | JV Girls Volleyball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Thu., 9/18 | V Football | Torrington | Home - Woodland High School [Directions] | L 27-28 (OT) | ||
| Thu., 9/18 | JV Girls Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 9/19 | FR Football | Torrington | Home - Woodland Football Field [Directions] | 3:45 p.m. | ||
| Fri., 9/19 | V Boys Soccer | Sacred Heart | Away - Hamilton Park | W 4-0 | 2:30 p.m. | |
| Fri., 9/19 | V Girls Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | W 7-0 | ||
| Fri., 9/19 | V Girls Swimming and Diving | Torrington | Away - Torrington Y [Directions] | Win | 6:00 p.m. | |
| Fri., 9/19 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 3-2 | 3:30 p.m. | |
| Fri., 9/19 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | L 1-2 | 3:30 p.m. | |
| Sat., 9/20 | JV Football | Torrington | Home - Woodland High School [Directions] | 10:30 a.m. | ||
| Sat., 9/20 | JV Boys Soccer | Sacred Heart | Away - Bucks Hill Park | 10:30 a.m. | 9:00 a.m. | |
| Sat., 9/20 | JV Girls Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 9/22 | V Girls Volleyball | Amity | Home - Woodland High School Gym [Directions] | L 1-3 | ||
| Mon., 9/22 | JV Girls Volleyball | Amity | Home - Woodland High School Gym [Directions] | W 2-1 | ||
| Tue., 9/23 | V Boys Cross Country | Sacred Heart, St. Paul Catholic, Seymour, Wilby | Away - Montoe Park | 3:30 p.m. | 2:30 p.m. | |
| Tue., 9/23 | V Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | L 0-4 | 3:00 p.m. | JV/Varsity same bus |
| Tue., 9/23 | JV Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | 3:00 p.m. | JV/Varsity on same bus |
| Tue., 9/23 | V Girls Soccer | Bunnell | Home - Woodland Soccer Field [Directions] | W 2-1 | ||
| Tue., 9/23 | V Girls Swimming and Diving | Oxford | Away - OHS Pool [Directions] | Loss | 2:30 p.m. | |
| Tue., 9/23 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 3-0 | 3:30 p.m. | |
| Tue., 9/23 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 2-0 | 3:30 p.m. | |
| Wed., 9/24 | V Boys Soccer | Torrington | Away - Torrington Middle School [Directions] | L 0-7 | 4:30 p.m. | |
| Wed., 9/24 | V Girls Soccer | Torrington | Home - Woodland Soccer Field [Directions] | W 4-2 | ||
| Thu., 9/25 | FR Football | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | 6:00 p.m. | 4:00 p.m. | |
| Thu., 9/25 | JV Boys Soccer | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Thu., 9/25 | JV Girls Soccer | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 9/26 | V Football | Wolcott | Home - Woodland Football Field [Directions] | L 7-26 | ||
| Fri., 9/26 | V Boys Soccer | Oxford | Home - Woodland Soccer Field [Directions] | L 3-4 | ||
| Fri., 9/26 | V Girls Swimming and Diving | Watertown | Home - Woodland High School Pool [Directions] | Loss | ||
| Fri., 9/26 | V Girls Volleyball | Oxford | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Fri., 9/26 | JV Girls Volleyball | Oxford | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Sat., 9/27 | JV Football | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | 9:00 a.m. | 8:15 a.m. | |
| Sat., 9/27 | JV Boys Soccer | Oxford | Home - Woodland Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/27 | JV Girls Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | 10:00 a.m. | 9:45 a.m. | |
| Mon., 9/29 | V Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | W 4-2 | ||
| Tue., 9/30 | V Boys Cross Country | Torrington, Watertown, Crosby | Away - Veterans Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 9/30 | JV Girls Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Tue., 9/30 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | W 3-2 | 3:45 p.m. | |
| Tue., 9/30 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | W 2-0 | 3:45 p.m. | |
| Wed., 10/1 | V Boys Soccer | Wilby | Away - Municipal Stadium [Directions] | W 3-0 | 3:45 p.m. | |
| Wed., 10/1 | V Girls Swimming and Diving | Seymour | Away - Seymour High School [Directions] | Loss | 2:15 p.m. | |
| Thu., 10/2 | FR Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:15 p.m. | |
| Thu., 10/2 | JV Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 10/2 | V Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | W 3-0 | 2:20 p.m. | |
| Thu., 10/2 | JV Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | W 2-0 | 2:20 p.m. | |
| Fri., 10/3 | V Football | St. Paul Catholic | Home - Woodland Football Field [Directions] | W 30-13 | ||
| Fri., 10/3 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 3-4(OT) | 2:30 p.m. | |
| Fri., 10/3 | V Girls Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | W 4-0 | ||
| Fri., 10/3 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck High School [Directions] | Loss | 4:30 p.m. | |
| Sat., 10/4 | JV Football | Derby | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/4 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 10:00 a.m. | 8:15 a.m. | |
| Mon., 10/6 | V Girls Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | L 1-2 | 2:30 p.m. | |
| Tue., 10/7 | V Boys Cross Country | Derby, Naugatuck | Away - Derby High School [Directions] | 3:30 p.m. | 2:30 p.m. | DeFlippo Field (Ryan Field) |
| Tue., 10/7 | V Boys Soccer | Wolcott | Home - Woodland Soccer Field [Directions] | W 3-0 | ||
| Tue., 10/7 | V Girls Soccer | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | W 3-0 | 2:30 p.m. | |
| Tue., 10/7 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 3-0 | 3:45 p.m. | |
| Tue., 10/7 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 2-0 | 3:45 p.m. | |
| Wed., 10/8 | JV Boys Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 10/8 | JV Girls Soccer | Wolcott | Away - Wolcott High School, Lower Soccer Field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 10/8 | V Girls Swimming and Diving | Suffield | Home - Woodland High School Pool [Directions] | Win | ||
| Wed., 10/8 | V Girls Volleyball | Wolcott | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Wed., 10/8 | JV Girls Volleyball | Wolcott | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Thu., 10/9 | V Girls Soccer | Torrington | Away - Torrington High School [Directions] | W 6-1 | 4:30 p.m. | |
| Fri., 10/10 | V Boys Soccer | Crosby | Home - Woodland Soccer Field [Directions] | L 1-3 | ||
| Fri., 10/10 | JV Girls Soccer | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 10/10 | V Girls Swimming and Diving | Sacred Heart | Home - Woodland High School Pool [Directions] | Loss | ||
| Fri., 10/10 | V Girls Volleyball | Crosby | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Fri., 10/10 | JV Girls Volleyball | Crosby | Home - Woodland High School Gym [Directions] | W 2-1 | ||
| Sat., 10/11 | JV Boys Soccer | Crosby | Home - Woodland Soccer Field [Directions] | 1:00 p.m. | ||
| Tue., 10/14 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | W 4-2(OT) | 2:30 p.m. | |
| Tue., 10/14 | V Girls Soccer | Ansonia | Home - Woodland Soccer Field [Directions] | W 3-0 | ||
| Tue., 10/14 | V Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | W 3-2 | 3:00 p.m. | |
| Tue., 10/14 | JV Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | W 2-1 | 3:00 p.m. | |
| Wed., 10/15 | V Boys Cross Country | NVL Tournament | Away - Veteran's Park | 3:30 p.m. | rain date 10/16/14 | |
| Wed., 10/15 | JV Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | Cancelled | . | |
| Wed., 10/15 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland High School Pool [Directions] | Win | ||
| Thu., 10/16 | V Girls Volleyball | Seymour | Home - Woodland High School Gym [Directions] | L 1-3 | ||
| Thu., 10/16 | JV Girls Volleyball | Seymour | Home - Woodland High School Gym [Directions] | W 2-1 | ||
| Fri., 10/17 | V Boys Cross Country | NVL Novice Race | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Fri., 10/17 | V Football | Weston | Home - Woodland Football Field [Directions] | L 8-19 | ||
| Fri., 10/17 | V Boys Soccer | Kennedy | Home - Woodland Soccer Field [Directions] | W 4-2 | ||
| Fri., 10/17 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | W 4-0 | 2:30 p.m. | |
| Fri., 10/17 | V Girls Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | Loss | 2:30 p.m. | |
| Fri., 10/17 | V Girls Volleyball | Torrington | Home - Woodland High School Gym [Directions] | W 3-2 | ||
| Fri., 10/17 | JV Girls Volleyball | Torrington | Home - Woodland High School Gym [Directions] | W 2-1 | ||
| Sat., 10/18 | JV Football | Weston | Away - WHS Stadium Field [Directions] | 1:00 p.m. | 11:00 A.M. | |
| Sat., 10/18 | JV Boys Soccer | Kennedy | Home - Woodland Soccer Field [Directions] | 1:00 p.m. | ||
| Sat., 10/18 | JV Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | Cancelled | 11:45 a.m. | |
| Mon., 10/20 | V Boys Cross Country | Platt Tech Invitational | Away - Eisenhower Park, Milford | 3:30 p.m. | 2:20 p.m. | |
| Mon., 10/20 | V Boys Soccer | Derby | Home - Woodland Football Field [Directions] | W 10-0 | Senior Night | |
| Mon., 10/20 | V Girls Soccer | Derby | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | W 7-0 | 2:30 p.m. | |
| Mon., 10/20 | V Girls Swimming and Diving | Kennedy | Home - Woodland High School Pool [Directions] | Win | ||
| Mon., 10/20 | V Girls Volleyball | Naugatuck | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Mon., 10/20 | JV Girls Volleyball | Naugatuck | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Tue., 10/21 | JV Boys Soccer | Derby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Tue., 10/21 | JV Girls Soccer | Derby | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 10/22 | V Boys Soccer | Seymour | Away - Seymour High Main Field [Directions] | T 2-2 | 4:45 p.m. | |
| Wed., 10/22 | V Girls Soccer | Seymour | Home - Woodland Football Field [Directions] | W 3-0 | SENIOR NIGHT | |
| Wed., 10/22 | V Girls Volleyball | Watertown | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Wed., 10/22 | JV Girls Volleyball | Watertown | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Thu., 10/23 | FR Football | Naugatuck | Home - Woodland Football Field [Directions] | 3:00 p.m. | ||
| Thu., 10/23 | JV Boys Soccer | Seymour | Away - Bungay School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 10/23 | V Girls Volleyball | Amity | Away - Amity High School [Directions] | L 1-3 | 3:00 p.m. | |
| Thu., 10/23 | JV Girls Volleyball | Amity | Away - Amity High School [Directions] | L 1-2 | 3:00 p.m. | |
| Fri., 10/24 | V Football | Naugatuck | Away - Naugatuck High School [Directions] | L 35-58 | 4:30 p.m. | |
| Fri., 10/24 | JV Girls Soccer | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 10/24 | JV Girls Volleyball | Junior Varsity Tournament | Home - Wolcott High School [Directions] | 3:00 p.m. | 2:20 p.m. | |
| Sat., 10/25 | V Boys Cross Country | CIAC Class SS Championship | Away - Wickham Park - East Hartford [Directions] | 3:45 p.m. | ||
| Sat., 10/25 | JV Football | Naugatuck | Home - Woodland Football Field [Directions] | 10:30 a.m. | ||
| Sat., 10/25 | V Girls Soccer | nvl tournament vs Ansonia | Away - Naugatuck High School | 2:00 p.m. | 12:30 p.m. | |
| Sat., 10/25 | V Girls Volleyball | NVL Tournament vs Ansonia | Home - Woodland High School Gym [Directions] | 12:30 p.m. | ||
| Mon., 10/27 | V Girls Soccer | Oxford | Away - Wolcott High School [Directions] | 7:00 p.m. | 5:00 p.m. | |
| Tue., 10/28 | V Girls Volleyball | Torrington | Away - Wilby High School [Directions] | W 3-2 | 3:00 p.m. | |
| Wed., 10/29 | FR Football | Wilby | Home - Woodland Football Field [Directions] | 3:30 p.m. | ||
| Wed., 10/29 | V Girls Soccer | NVL Championships vs Watertown | Away - Municipal Stadium | 5:30 p.m. | 4:00 p.m. | |
| Wed., 10/29 | V Girls Swimming and Diving | NVL Swim Trials | Away - Kennedy High School | 4:00 p.m. | 1:15 p.m. | 1:15 warm ups |
| Thu., 10/30 | V Football | Wilby | Home - Wilby H.S. [Directions] | W 50-14 | ||
| Thu., 10/30 | V Girls Swimming and Diving | NVL Diving Championships | Away - Kennedy | 1st Place | ||
| Thu., 10/30 | V Girls Volleyball | NVL Championships vs Seymour | Away - Kennedy High School | 7:00 p.m. | 5:30 p.m. | |
| Fri., 10/31 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | Region 16 is not providing transportation | |
| Sat., 11/1 | JV Football | Wilby | Home - Woodland Football Field [Directions] | 10:30 a.m. | ||
| Sat., 11/1 | V Girls Swimming and Diving | NVL Swim Championships | Away - Kennedy | 4:00 p.m. | 4:30 warm ups | |
| Mon., 11/3 | V Boys Soccer | Montville | Away - Montville Turf Field [Directions] | 4:00 p.m. | 1:00 p.m. | |
| Tue., 11/4 | V Girls Soccer | Foran | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Wed., 11/5 | FR Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Wed., 11/5 | V Girls Volleyball | 2nd Round States vs Wolcott | Home - Woodland High School Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/6 | V Girls Soccer | 2nd round state tournament vs Weston | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Thu., 11/6 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Fri., 11/7 | V Football | Ansonia | Home - Woodland Football Field [Directions] | L 28-30 | ||
| Fri., 11/7 | V Girls Volleyball | State Tournament 1/4 finals vs Foran | Home - Woodland High School Gym [Directions] | 6:00 p.m. | ||
| Sat., 11/8 | V Boys Cross Country | New England Championship | Away - Wickham Park - East Hartford [Directions] | TBA | ||
| Sat., 11/8 | JV Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 10:00 a.m. | 8:30 p.m. | |
| Sat., 11/8 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 4:00 p.m. | ||
| Sat., 11/8 | V Girls Swimming and Diving | CIAC Class S Swim Trials | Away - Plainville High School | 4:00 p.m. | ||
| Tue., 11/11 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Wed., 11/12 | FR Football | Holy Cross | Away - Holy Cross HS [Directions] | 3:15 p.m. | 2:15 p.m. | |
| Fri., 11/14 | V Football | Holy Cross | Home - Woodland Football Field [Directions] | L 7-14 | ||
| Fri., 11/14 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/15 | JV Football | Holy Cross | Away - Holy Cross HS [Directions] | 10:00 a.m. | 8:30 p.m. | |
| Sat., 11/15 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Fri., 11/21 | V Football | Derby | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | L 19-20 | 4:30 p.m. | |
| Tue., 11/25 | V Football | Seymour | Home - Woodland Football Field [Directions] | W 41-14 | ||
| Tue., 11/25 | FR Football | Seymour | Away - Seymour High Lower Field [Directions] | Cancelled | 2:30 p.m. | |
| Wed., 12/3 | V Girls Basketball | Shepaug Valley (Scrim.) | Away - Ted Alex Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 12/6 | V Boys Basketball | Australia | Home - Woodland High School Gym [Directions] | 6:30 p.m. | ||
| Sat., 12/6 | JV Boys Basketball | Australia | Home - Woodland High School Gym [Directions] | 5:00 p.m. | ||
| Sat., 12/6 | FR Boys Basketball | Australia | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/6 | V Girls Basketball | Griswold (Scrim.) | Away - Griswold [Directions] | 11:00 a.m. | 8:45 a.m. | |
| Wed., 12/10 | V Boys Basketball | Kaynor Tech (Scrim.) | Away - Dick Ierardi Gymnasium [Directions] | 5:30 p.m. | 3:15 p.m. | |
| Wed., 12/10 | JV Boys Basketball | Kaynor Tech (Scrim.) | Away - Dick Ierardi Gymnasium [Directions] | 4:00 p.m. | 3:15 p.m. | |
| Wed., 12/10 | FR Girls Basketball | Torrington | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Thu., 12/11 | V Girls Basketball | Torrington | Home - Woodland High School Gym [Directions] | L 27-59 | ||
| Thu., 12/11 | JV Girls Basketball | Torrington | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/12 | V Boys Swimming and Diving | NVL Indicational | Away - Kennedy High School | 4:00 p.m. | 2:30 p.m. | |
| Fri., 12/12 | V Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | W 33-29 | 4:30 p.m. | |
| Fri., 12/12 | JV Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | 4:30 p.m. | |
| Sat., 12/13 | V Boys Basketball | Ansonia (Scrim.) | Home - Woodland High School Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/13 | V Wrestling | Southington (Scrim.) | Away [Directions] | 9:00 a.m. | 8:00 | |
| Mon., 12/15 | V Boys Indoor Track | Wesleyan Developmental | Away | TBA | 2:30 p.m. | |
| Wed., 12/17 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | W 85-74 | 4:00 p.m. | |
| Wed., 12/17 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Wed., 12/17 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | Loss | 2:45 p.m. | |
| Wed., 12/17 | V Girls Basketball | Oxford | Home - Woodland High School Gym [Directions] | L 34-28 | ||
| Wed., 12/17 | JV Girls Basketball | Oxford | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/18 | V Boys Indoor Track | Glastonbury Developmental | Away - Glastonbury High School | TBA | 2:30 p.m. | 2 buses |
| Thu., 12/18 | V Wrestling | Xavier | Away - Xavier H.S. [Directions] | L 54-24 | 3:30 | |
| Fri., 12/19 | V Boys Basketball | Kennedy | Home - Woodland High School Gym [Directions] | L 64-99 | ||
| Fri., 12/19 | JV Boys Basketball | Kennedy | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/19 | FR Boys Basketball | Kennedy | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Fri., 12/19 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck High School [Directions] | Loss | 4:30 p.m. | |
| Fri., 12/19 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 59-36 | 4:15 p.m. | |
| Fri., 12/19 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Sat., 12/20 | V Boys Indoor Track | Reindeer Relays | Away - Wilton High School | TBA | TBA | |
| Sat., 12/20 | V Wrestling | Shelton Invitational | Away [Directions] | 6th Place out of 12 | 7:15 a.m. | |
| Mon., 12/22 | V Wrestling | Branford | Home - Amity High School [Directions] | L 22 - 58 | ||
| Mon., 12/22 | V Girls Basketball | Kaynor Tech | Away - Dick Ierardi Gymnansium [Directions] | L 43-38 | 4:00 p.m. | |
| Mon., 12/22 | JV Girls Basketball | Kaynor Tech | Away - Dick Ierardi Gymnasium [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Sat., 12/27 | V Boys Indoor Track | Hillhouse Winter Relays | Away - FLAC - Hillhouse | TBA | TBA | |
| Sat., 12/27 | V Wrestling | Danbury Holiday Tournament | Away [Directions] | 11th Place | 7:00 a.m. | |
| Sat., 12/27 | V Girls Basketball | Bacon Academy | Home - Woodland High School Gym [Directions] | L 56-39 | ||
| Sat., 12/27 | JV Girls Basketball | Bacon Academy | Home - Woodland High School Gym [Directions] | 12:00 p.m. | ||
| Mon., 12/29 | V Boys Basketball | Platt Tech | Home - Woodland High School Gym [Directions] | L 52-71 | ||
| Mon., 12/29 | JV Boys Basketball | Platt Tech | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/29 | FR Boys Basketball | Platt Tech | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/29 | V Wrestling | Shelton | Home - Amity High School [Directions] | L 14 - 64 | ||
| Tue., 12/30 | V Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | L 69-74 | 4:00 p.m. | |
| Tue., 12/30 | FR Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 3:15 p.m. | 1;45 P.M. | |
| Tue., 12/30 | V Boys Indoor Track | NVL Developmental | Away - Danbury Sports Dome | TBA | 2:30 | |
| Tue., 12/30 | V Girls Basketball | Wilby | Away - Wilby H.S. [Directions] | W 44-20 | 3:45 p.m. | |
| Sat., 1/3 | JV Boys Basketball | Wilby | Home - Woodland High School Gym [Directions] | 12:30 p.m. | ||
| Sat., 1/3 | V Boys Indoor Track | Shoreline Coaches Invitational | Away - FLAC - Hillhouse | TBA | TBA | |
| Sat., 1/3 | V Wrestling | Southington Duals | Away - Southington High School | 12th Place | 7:00 a.m. | |
| Sat., 1/3 | JV Girls Basketball | Wilby | Home - Woodland High School Gym [Directions] | 2:00 p.m. | ||
| Tue., 1/6 | V Boys Basketball | Derby | Home - Woodland High School Gym [Directions] | L 60-62 | ||
| Tue., 1/6 | JV Boys Basketball | Derby | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/6 | V Girls Basketball | Derby | Away - Derby HS Vitello Gymnasium [Directions] | W 44-39 | 4:00 p.m. | |
| Tue., 1/6 | JV Girls Basketball | Derby | Away - Derby HS Vitello Gymnasium [Directions] | Cancelled | 4:00 p.m. | |
| Wed., 1/7 | FR Boys Basketball | Bethel | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/7 | V Boys Swimming and Diving | Northwestern | Home - Woodland High School Pool [Directions] | Loss | ||
| Wed., 1/7 | V Wrestling | Guilford | Home - Amity High School [Directions] | L 12 - 66 | ||
| Thu., 1/8 | V Boys Basketball | Bethel | Home - Woodland High School Gym [Directions] | L 54-58 | ||
| Thu., 1/8 | JV Boys Basketball | Bethel | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/10 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 12:00 p.m. | 11:00 a.m. | |
| Sat., 1/10 | V Boys Indoor Track | Glastonbury Fro-Soph | Away - Glastonbury High School | TBA | TBA | |
| Sat., 1/10 | V Boys Indoor Track | Springfield Winter Classic | Away - Springfield College | TBA | Region16 will not be providing transportation | |
| Sat., 1/10 | V Wrestling | Natick Invitational | Away - Natick, MA | 7th place out of 14 | 5:00 a.m. | |
| Tue., 1/13 | V Wrestling | Cheshire | Home - Amity High School [Directions] | L 30 - 48 | ||
| Wed., 1/14 | V Boys Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | L 68-73 | ||
| Wed., 1/14 | JV Boys Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/14 | FR Boys Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/14 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 17-59 | 4:00 p.m. | |
| Wed., 1/14 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Fri., 1/16 | V Boys Basketball | Ansonia | Home - Woodland High School Gym [Directions] | L 66-71 | ||
| Fri., 1/16 | JV Boys Basketball | Ansonia | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/16 | V Boys Indoor Track | NVL Developmental | Away - Wesleyan University | TBA | 2:30 p.m. | 2 buses |
| Fri., 1/16 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Woodland High School Pool [Directions] | Won | ||
| Fri., 1/16 | V Girls Basketball | Ansonia | Away - Ansonia High School [Directions] | W 46-28 | 3:15 | |
| Fri., 1/16 | JV Girls Basketball | Ansonia | Away - Ansonia High School [Directions] | 4:15 p.m. | 3:15 p.m. | |
| Sat., 1/17 | V Boys Indoor Track | Hillhouse Invite | Away - Hillhouse-FLAC | 9:00 a.m. | 8:00 a.m. | |
| Sat., 1/17 | V Boys Indoor Track | H-K Invitational | Away - FLAC - Hillhouse | TBA | 2:30 p.m. | |
| Sat., 1/17 | V Wrestling | New Milford Invitational | Away - New Milford High School | 10th place out of 22 | 6:00 a.m. | |
| Tue., 1/20 | V Boys Basketball | Holy Cross | Away - Tim McDonald Gymnasium [Directions] | L 44-92 | 4:15 p.m. | |
| Tue., 1/20 | JV Boys Basketball | Holy Cross | Away - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Tue., 1/20 | FR Boys Basketball | Holy Cross | Away - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 1/20 | V Boys Indoor Track | NVL Developmental | Away - Danbury Sports Zone | TBA | 2:30 | |
| Tue., 1/20 | V Boys Swimming and Diving | Seymour | Away - Seymour High School [Directions] | Won | 4:30 p.m. | |
| Tue., 1/20 | V Girls Basketball | Holy Cross | Home - Woodland High School Gym [Directions] | L 47-72 | ||
| Tue., 1/20 | JV Girls Basketball | Holy Cross | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/21 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | L 36-72 | 4:15 p.m. | |
| Wed., 1/21 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | 4:15 p.m. | |
| Wed., 1/21 | V Wrestling | East Haven | Away [Directions] | L 34 - 43 | 4:30 | |
| Wed., 1/21 | V Girls Basketball | Sacred Heart | Home - Woodland High School Gym [Directions] | L 33-46 | ||
| Wed., 1/21 | JV Girls Basketball | Sacred Heart | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/22 | V Boys Swimming and Diving | Kennedy | Home - Woodland High School Pool [Directions] | Won | ||
| Fri., 1/23 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | L 44-67 | 4:15 p.m. | |
| Fri., 1/23 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Fri., 1/23 | V Boys Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | Loss | 2:30 p.m. | |
| Fri., 1/23 | V Girls Basketball | Watertown | Home - Woodland High School Gym [Directions] | L 40-37 | ||
| Fri., 1/23 | JV Girls Basketball | Watertown | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/24 | V Boys Indoor Track | SCC Coaches Invitational | Away - FLAC - Hillhouse | TBA | 2:30 p.m. | |
| Sat., 1/24 | V Wrestling | Somers Duals | Away - Somers High School | Cancelled | ||
| Wed., 1/28 | V Boys Basketball | Seymour | Home - Woodland High School Gym [Directions] | W 81-45 | ||
| Wed., 1/28 | JV Boys Basketball | Seymour | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/28 | FR Boys Basketball | Seymour | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/28 | V Boys Swimming and Diving | Oxford | Away - OHS Pool [Directions] | Won | 2:30 p.m. | |
| Wed., 1/28 | V Girls Basketball | Seymour | Away - Seymour High School [Directions] | L 41-57 | 4:30 p.m. | |
| Wed., 1/28 | JV Girls Basketball | Seymour | Away - Seymour High School [Directions] | 5:15 p.m. | 4:30 p.m. | |
| Fri., 1/30 | V Boys Basketball | Crosby | Away - Crosby HS [Directions] | L 44-93 | 4:15 p.m. | |
| Fri., 1/30 | JV Boys Basketball | Crosby | Away - Crosby HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Fri., 1/30 | V Girls Basketball | Crosby | Home - Woodland High School Gym [Directions] | L 27-50 | ||
| Fri., 1/30 | JV Girls Basketball | Crosby | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/31 | FR Boys Basketball | Crosby | Away - Crosby HS [Directions] | 10:00 a.m. | 8:45 a.m. | |
| Sat., 1/31 | V Boys Indoor Track | NVL Prep | Away - Wilton High School | TBA | TBA | NVL Qualifiers only |
| Sat., 1/31 | V Wrestling | Ridgefield Challenge | Away - Ridgefield High School | 10:00 a.m. | 7:00 a.m. | |
| Wed., 2/4 | V Boys Swimming and Diving | Crosby/WCA | Home - Woodland High School Pool [Directions] | Won | ||
| Thu., 2/5 | V Boys Basketball | Torrington | Home - Woodland High School Gym [Directions] | W 68-66 | ||
| Thu., 2/5 | JV Boys Basketball | Torrington | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/5 | FR Boys Basketball | Torrington | Home - Woodland High School Gym [Directions] | 3:45 p.m. | ||
| Thu., 2/5 | V Wrestling | Fairfield Prep | Home - Amity High School [Directions] | 6:30 p.m. | SENIOR NIGHT | |
| Thu., 2/5 | V Girls Basketball | Torrington | Away - Torrington High School [Directions] | L 21-53 | 4:15 p.m. | |
| Thu., 2/5 | JV Girls Basketball | Torrington | Away - Torrington High School [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Fri., 2/6 | V Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | L 51-77 | 4:15 p.m. | |
| Fri., 2/6 | JV Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Fri., 2/6 | FR Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 2/6 | V Boys Swimming and Diving | Watertown | Home - Woodland High School Pool [Directions] | Loss | . | |
| Fri., 2/6 | V Girls Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | W 54-28 | ||
| Fri., 2/6 | JV Girls Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/7 | V Wrestling | Foran Duals | Away - Foran High School | Won 3 out of 5 | 7:30 a.m. | |
| Sun., 2/8 | V Boys Indoor Track | NVL Indoor Championships | Away - FLAC - Hillhouse | 9:30 a.m. | 7:30 a.m. | 2 buses |
| Tue., 2/10 | V Boys Basketball | Watertown | Home - Woodland High School Gym [Directions] | L 42-66 | ||
| Tue., 2/10 | JV Boys Basketball | Watertown | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/10 | FR Boys Basketball | Highville Charter School | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/10 | V Boys Swimming and Diving | Sacred Heart | Home - Woodland High School Pool [Directions] | Loss | ||
| Tue., 2/10 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | L 21-42 | 4:15 p.m. | |
| Tue., 2/10 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Wed., 2/11 | V Wrestling | New Haven Wrestling | Away - Wilbur Cross Gym [Directions] | L 34 - 39 | 5:00 | |
| Wed., 2/11 | V Girls Basketball | Wolcott | Home - Woodland High School Gym [Directions] | L 44-60 | ||
| Wed., 2/11 | JV Girls Basketball | Wolcott | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/12 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | L 47-74 | 4:00 p.m. | |
| Thu., 2/12 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Thu., 2/12 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Thu., 2/12 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/13 | V Boys Basketball | Wolcott | Home - Woodland High School Gym [Directions] | L 61-76 | ||
| Fri., 2/13 | JV Boys Basketball | Wolcott | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/13 | FR Boys Basketball | Wolcott | Home - Woodland High School Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/13 | V Boys Swimming and Diving | Torrington | Home - Woodland High School Pool [Directions] | Loss | ||
| Fri., 2/13 | V Wrestling | JV SCC Tournament | Home [Directions] | 4:00 p.m. | ||
| Fri., 2/13 | JV Wrestling | SCC JV Tournament | Home - Amity High School [Directions] | 4:00 p.m. | ||
| Fri., 2/13 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | L 36-41 | 4:00 p.m. | |
| Fri., 2/13 | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Sat., 2/14 | V Wrestling | SCC Tournament | Home - Amity High School [Directions] | 9:00 a.m. | ||
| Mon., 2/16 | JV Wrestling | NFA JV Tournament | Away | 10:00 a.m. | TBA | |
| Fri., 2/20 | V Boys Basketball | Torrington | Away - Torrington High School [Directions] | L 67-76 | 4:00 p.m. | |
| Fri., 2/20 | JV Boys Basketball | Torrington | Away - Torrington High School [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Fri., 2/20 | FR Boys Basketball | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Fri., 2/20 | V Wrestling | CLASS LL Tournament | Away - Trumbull High School [Directions] | 4:30 p.m. | 2:30 | |
| Sat., 2/21 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/21 | V Wrestling | CLASS LL Tournament | Away - Trumbull High School [Directions] | 10:00 a.m. | 7:00 a.m. | drop off and return for pick up 4:00 p.m.. If Amity is still participating in the event, the bus may have to wait a little while. |
| Tue., 2/24 | V Boys Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | L 58-84 | ||
| Tue., 2/24 | JV Boys Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/24 | FR Boys Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/27 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | ||
| Fri., 2/27 | V Wrestling | STATE OPEN | Away - Floyd Little Athletic Center [Directions] | 4:30 p.m. | ||
| Sat., 2/28 | V Boys Swimming and Diving | Girls Splash Classic | Away - Plainville High School | 10:00 a.m. | warm ups from 8am -10am | |
| Sat., 2/28 | V Wrestling | STATE OPEN | Away - Floyd Little Athletic Center [Directions] | 9:00 a.m. | ||
| Wed., 3/4 | V Boys Swimming and Diving | NVL Trials | Away - Kennedy High School | 4:00 p.m. | 2:30 p.m. | |
| Thu., 3/5 | V Boys Swimming and Diving | NVL Diving | Away - Kennedy High School | 6:00 p.m. | 4:30 p.m. | |
| Fri., 3/6 | V Boys Swimming and Diving | NVL Finals | Away - Kennedy High School | 6:00 p.m. | 4:30 p.m. | |
| Fri., 3/6 | V Wrestling | NEW ENGLANDS | Away - North Andover HS, MA [Directions] | Cancelled | ||
| Sat., 3/7 | V Wrestling | NEW ENGLANDS | Away - N. Andover HS, MA [Directions] | Cancelled | ||
| Thu., 3/12 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 3:30 p.m. | ||
| Wed., 3/18 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | ||
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Sat., 3/28 | V Baseball | Gilbert (Scrim.) | Home - Woodland High School Baseball Field [Directions] | Cancelled | ||
| Mon., 4/6 | V Baseball | Bethel (Scrim.) | Away - Hunt Field at Bethel High School [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Wed., 4/8 | V Boys Outdoor Track | Bullard Havens Tech, Kaynor Tech | Home - Woodland High School Track [Directions] | 3:45 p.m. | ||
| Wed., 4/8 | V Girls Outdoor Track | Bullard Havens Tech, Kaynor Tech | Home - Woodland High School Track [Directions] | 3:45 p.m. | ||
| Thu., 4/9 | V Baseball | Naugatuck | Away - Rotary Field [Directions] | W 5-1 | 2:20 p.m. | |
| Thu., 4/9 | V Boys Tennis | Naugatuck | Away - Naugatuck High School [Directions] | L 1-8 | 2:30 p.m. | |
| Thu., 4/9 | V Softball | Naugatuck | Away - Breen Field [Directions] | W 6-4 | ||
| Thu., 4/9 | V Girls Tennis | Naugatuck | Home - Woodland High School Tennis courts [Directions] | W 4-3 | ||
| Fri., 4/10 | V Girls Tennis | St. Paul Catholic | Home - Woodland High School Tennis courts [Directions] | W 5-2 | ||
| Sat., 4/11 | V Baseball | Oxford | Home - OHS Baseball Field [Directions] | L 10-9 | ||
| Sat., 4/11 | FR Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 3:00 p.m. | 1:30 | |
| Sat., 4/11 | V Softball | Oxford | Away - OHS Softball Field [Directions] | L 0-4 | 9:00 a.m. | |
| Sat., 4/11 | JV Softball | Oxford | Away - OHS Softball Field [Directions] | 12:30 p.m. | 9:00 a.m. | |
| Mon., 4/13 | V Baseball | Kennedy | Away - Waterville Park [Directions] | W 17-6 | 2:20 p.m. | |
| Mon., 4/13 | FR Baseball | Kennedy | Away - Bucks Hill Park [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Mon., 4/13 | V Softball | Kennedy | Home - Woodland Softball Field [Directions] | W 16-1 | ||
| Mon., 4/13 | V Girls Tennis | Seymour | Home - Woodland High School Tennis courts [Directions] | W 6-2 | ||
| Tue., 4/14 | V Boys Outdoor Track | Crosby, Oxford | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Tue., 4/14 | V Girls Outdoor Track | Crosby, Oxford | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Wed., 4/15 | V Baseball | Goodwin Tech | Home - Woodland High School Baseball Field [Directions] | W 5-1 | ||
| Wed., 4/15 | JV Baseball | Kennedy | Home - Woodland High School Baseball Field [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Wed., 4/15 | V Boys Tennis | Kennedy | Away - Chase Park [Directions] | L 3-6 | 2:30 p.m. | |
| Wed., 4/15 | V Girls Tennis | Kennedy | Home - Woodland High School Tennis courts [Directions] | W 4-3 | ||
| Thu., 4/16 | JV Baseball | Goodwin Tech | Home - Woodland High School Baseball Field [Directions] | 11:00 a.m. | ||
| Thu., 4/16 | V Boys Tennis | Sacred Heart | Away - Fulton Park | L 1-8 | 2:30 p.m. | |
| Thu., 4/16 | V Softball | Wilby | Away - Bucks Hill Park [Directions] | W 21-0(5) | 2:30 p.m. | |
| Thu., 4/16 | JV Softball | Wilby | Away - Bucks Hill Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 4/17 | V Baseball | Wilby | Home - Woodland High School Baseball Field [Directions] | W 7-5 | ||
| Fri., 4/17 | FR Baseball | Wilby | Home - Wilby High School [Directions] | 3:30 p.m. | ||
| Fri., 4/17 | V Boys Tennis | Wilby | Home - Woodland High School Tennis courts [Directions] | L 3-6 | ||
| Fri., 4/17 | V Girls Tennis | Wilby | Away - Wilby H.S. [Directions] | W 7-0 | 2:30 p.m. | |
| Sat., 4/18 | JV Baseball | Wilby | Home - Woodland High School Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/18 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | L 1-8 | 2:30 p.m. | |
| Tue., 4/21 | V Baseball | Derby | Away - Derby -Ryan Athletic Complex-baseball field [Directions] | L 6-4 | 2:20 p.m. | |
| Tue., 4/21 | V Boys Outdoor Track | Naugatuck, Derby, Watertown | Away - Naugatuck Track [Directions] | 3:30 p.m. | ||
| Tue., 4/21 | V Boys Tennis | Torrington | Home - Woodland High School Tennis courts [Directions] | L 1-8 | ||
| Tue., 4/21 | V Girls Outdoor Track | Naugatuck, Derby, Watertown | Away - Naugatuck Track [Directions] | 3:30 p.m. | ||
| Tue., 4/21 | V Girls Tennis | Torrington | Away - Torrington High School [Directions] | W 5-2 | 2:30 p.m. | |
| Wed., 4/22 | V Baseball | Sacred Heart | Home - Waterville Park [Directions] | W 15-5 | ||
| Wed., 4/22 | V Softball | Sacred Heart | Away - Municipal Stadium | W 11-3 | 2:30 p.m. | |
| Wed., 4/22 | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | Cancelled | 2:30 p.m. | |
| Thu., 4/23 | JV Baseball | Torrington | Home - Woodland High School Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/23 | V Boys Golf | Crosby | Away - East Mountain [Directions] | Woodland 171 Crosby 262 Mike Erickson 37 Ryan Warner 43 Zach Crowell 43 Julian Perino 48 | 2:10 p.m. | |
| Thu., 4/23 | V Boys Tennis | Kennedy | Home - Woodland High School Tennis courts [Directions] | L 4-5 | ||
| Fri., 4/24 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 9-8 | 2:20 p.m. | |
| Fri., 4/24 | FR Baseball | St. Paul Catholic | Away - Nassahegan Recreation Complex, Burlington [Directions] | 4:00 p.m. | 2:20 p.m. | |
| Fri., 4/24 | V Boys Golf | Wolcott | Away - Farmingbury Country Club [Directions] | Woodland 172 Wolcott 199 Mike Erickson 36 Ryan Warner 47 Zach Crowell 47 Julian Perino 42 | 2:10 p.m. | |
| Fri., 4/24 | V Softball | St. Paul Catholic | Home - Woodland Softball Field [Directions] | L 1-7 | ||
| Fri., 4/24 | JV Softball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:00 p.m. | ||
| Fri., 4/24 | V Girls Tennis | St. Paul Catholic | Home - Woodland High School Tennis courts [Directions] | L 1-6 | 2:30 p.m. | |
| Sat., 4/25 | V Baseball | Torrington | Home - Woodland High School Baseball Field [Directions] | L 15-0 | ||
| Sat., 4/25 | FR Baseball | Torrington | Home - Woodland High School Baseball Field [Directions] | 1:30 p.m. | ||
| Sat., 4/25 | V Softball | Torrington | Away - Torrington High School [Directions] | L 2-16 | 9:15 a.m. | |
| Mon., 4/27 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | W 17-1 | 2:20 p.m. | |
| Mon., 4/27 | FR Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Mon., 4/27 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | Woodland 176 Torrington 196 Mike Erickson 42 Ryan Warner 43 Zach Crowell 45 Owen Harris 46 | 2:10 p.m. | |
| Mon., 4/27 | V Boys Tennis | Watertown | Home - Woodland High School Tennis courts [Directions] | L 2-7 | ||
| Mon., 4/27 | V Softball | Ansonia | Home - Woodland Softball Field [Directions] | W 4-3 | ||
| Mon., 4/27 | JV Softball | WCA | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Tue., 4/28 | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Tue., 4/28 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | Woodland 169 Naugatuck 236 Mike Erickson 40 Ryan Warner 40 Zach Crowell 42 Owen Harris 47 | 2:10 p.m. | |
| Tue., 4/28 | V Boys Outdoor Track | Seymour, St. Paul Catholic, Wilby | Away - Seymour High School [Directions] | 4:00 p.m. | ||
| Tue., 4/28 | V Girls Outdoor Track | Seymour, St. Paul Catholic, Wilby | Away - Seymour High School [Directions] | 4:00 p.m. | ||
| Tue., 4/28 | V Girls Tennis | Ansonia | Home - Woodland High School Tennis courts [Directions] | W 7-0 | ||
| Wed., 4/29 | V Baseball | Holy Cross | Home - Woodland High School Baseball Field [Directions] | L 6-1 | ||
| Wed., 4/29 | FR Baseball | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 4/29 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | Woodland 183 Kennedy Mike Erickson 40 Ryan Warner 43 Owen Harris 49 Zach Crowell 51 | 2:10 p.m. | |
| Wed., 4/29 | V Boys Tennis | Holy Cross | Home - Woodland High School Tennis courts [Directions] | L 0-9 | ||
| Wed., 4/29 | V Softball | Holy Cross | Away - HCHS [Directions] | L 1-6 | 2:30 p.m. | |
| Wed., 4/29 | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 4/29 | V Girls Tennis | Holy Cross | Away - Holy Cross HS [Directions] | W 5-2 | 2:30 p.m. | |
| Thu., 4/30 | V Baseball | Watertown | Home - Woodland High School Baseball Field [Directions] | L 5-9 | ||
| Thu., 4/30 | JV Baseball | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 4/30 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | Woodland 172 Sacred Heart 217 Mike Erickson 39 Ryan Warner 43 Owen Harris 45 Julian Perino 46 | 2:10 p.m. | |
| Thu., 4/30 | V Softball | Watertown | Away - Watertown High School [Directions] | L 1-13 | 2:30 p.m. | |
| Thu., 4/30 | JV Softball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Thu., 4/30 | V Girls Tennis | Sacred Heart | Away - Fulton Park | W 5-2 | 2:30 p.m. | |
| Fri., 5/1 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | L 2-7 | 2:30 p.m. | |
| Sat., 5/2 | JV Baseball | Watertown | Home - Woodland High School Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/2 | V Softball | Derby | Home - Woodland Softball Field [Directions] | W 15-0 | ||
| Sat., 5/2 | JV Softball | Naugatuck | Home - Naugatuck High School [Directions] | Cancelled | ||
| Mon., 5/4 | V Baseball | Wolcott | Away - Wolcott High School [Directions] | L 2-11 | 2:20 p.m. | |
| Mon., 5/4 | FR Baseball | Wolcott | Away - BAW [Directions] | 3:45 p.m. | 2:20 p.m. | |
| Mon., 5/4 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | Woodland 179 Holy Cross 186 Mike Erickson 37 Ryan Warner 48 Zach Crowell 46 Owen Harris 48 | 2:10 p.m. | |
| Mon., 5/4 | V Boys Tennis | Wolcott | Home - Woodland High School Tennis courts [Directions] | L 0-9 | ||
| Mon., 5/4 | V Softball | Wolcott | Home - Woodland Softball Field [Directions] | W 13-9 | ||
| Mon., 5/4 | JV Softball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Mon., 5/4 | V Girls Tennis | Wolcott | Home - Woodland High School Tennis courts [Directions] | L 2-5 | ||
| Tue., 5/5 | JV Baseball | Wolcott | Away - Wolcott High School [Directions] | 3:45 p.m. | 2:20 | |
| Tue., 5/5 | V Boys Outdoor Track | Kennedy, Sacred Heart | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Tue., 5/5 | V Girls Outdoor Track | Kennedy, Sacred Heart | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Wed., 5/6 | V Baseball | Seymour | Away - French Park [Directions] | W 11-0 | 2:20 p.m. | |
| Wed., 5/6 | FR Baseball | Seymour | Away - Seymour High School [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Wed., 5/6 | V Boys Golf | Abbott Tech | Home - Oxford Greens [Directions] | Woodland 166 Abbott Tech.-239 Mike Erickson-36 Ryan Warner-40 Owen Harris-45 Julian Perino-45 | 2:10 p.m. | |
| Wed., 5/6 | V Boys Tennis | Torrington | Away - Torrington High School [Directions] | L 1-8 | 2:30 p.m. | |
| Wed., 5/6 | V Softball | Seymour | Home - Woodland Softball Field [Directions] | L 1-12 | ||
| Thu., 5/7 | JV Baseball | Seymour | Away - French Park [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Thu., 5/7 | V Boys Golf | Woodland Invitational | Home - Oxford Greens [Directions] | Woodland 369 Mike Erickson 38,38-76 Ryan Warner 44,51-95 Zach Crowell 44,50-94 Owen Harris 52,52-104 | ||
| Thu., 5/7 | JV Softball | Seymour | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Fri., 5/8 | V Baseball | Crosby | Home - Woodland High School Baseball Field [Directions] | W 15-5 | ||
| Fri., 5/8 | V Boys Tennis | Crosby | Home - Woodland High School Tennis courts [Directions] | W 6-3 | ||
| Fri., 5/8 | V Softball | Crosby | Away - Crosby HS Field #1 [Directions] | W 22-2 | 2:30 p.m. | |
| Fri., 5/8 | JV Softball | Crosby | Away - Crosby HS Field #2 [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 5/8 | V Girls Tennis | Crosby | Away - Crosby HS [Directions] | W 4-3 | 2:30 p.m. | |
| Sat., 5/9 | JV Baseball | Crosby | Home - Woodland High School Baseball Field [Directions] | 10:00 a.m. | ||
| Mon., 5/11 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | W 10-2 | 2:20 p.m. | |
| Mon., 5/11 | FR Baseball | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:20 p.m. | |
| Mon., 5/11 | V Boys Golf | Watertown | Away - Crestbrook Park Golf Course [Directions] | Woodland 195 Watertown 174 Mike Erickson- 49 Ryan Warner- 48 Zach Crowell- 49 Julian Perino- 49 | 2:10 p.m. | |
| Mon., 5/11 | V Boys Tennis | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | L 0-9 | 2:30 p.m. | |
| Mon., 5/11 | V Softball | Torrington | Home - Woodland Softball Field [Directions] | L 0-9 | ||
| Mon., 5/11 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | W 7-0 | 2:30 p.m. | |
| Tue., 5/12 | JV Baseball | Torrington | Home - Torrington High School [Directions] | 3:45 p.m. | . | |
| Tue., 5/12 | V Boys Golf | St. Paul Catholic | Away - Chippanee [Directions] | Woodland-173 St. Paul-181 Mike Erickson-40 Ryan Warner-42 Zach Crowell-42 Julian Perino-49 | 2:10 p.m. | |
| Tue., 5/12 | V Boys Outdoor Track | Holy Cross, Wolcott, Torrington | Away - Torrington [Directions] | 3:30 p.m. | ||
| Tue., 5/12 | V Girls Outdoor Track | Holy Cross, Wolcott, Torrington | Away - Torrington [Directions] | 3:30 p.m. | ||
| Wed., 5/13 | V Baseball | Naugatuck | Home - Woodland High School Baseball Field [Directions] | L 8-1 | ||
| Wed., 5/13 | FR Baseball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 5/13 | V Boys Golf | Stigberg Tournament | Away | Woodland- 70, 2nd place Ryan Warner Julian Perino | ||
| Wed., 5/13 | V Boys Tennis | Naugatuck | Home - Woodland High School Tennis courts [Directions] | L 4-5 | ||
| Wed., 5/13 | V Softball | Naugatuck | Home - Woodland Softball Field [Directions] | L 4-11 | ||
| Wed., 5/13 | JV Softball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | . | |
| Wed., 5/13 | V Girls Tennis | Seymour | Away - Seymour High School [Directions] | W 6-1 | 2:30 p.m. | |
| Thu., 5/14 | V Baseball | Watertown | Away - Deland Field [Directions] | L 10-4 | 2:20 p.m. | |
| Thu., 5/14 | JV Baseball | Naugatuck | Home - Woodland High School Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 5/14 | V Boys Golf | Kaynor Tech | Home - Oxford Greens [Directions] | Woodland 183 Kaynor Tech. 225 Mike Erickson 44 Ryan Warner 45 Zach Crowell 40 Julian Perion 54 | 2:10 p.m. | |
| Thu., 5/14 | V Boys Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | L 4-5 | 2:30 p.m. | |
| Thu., 5/14 | V Softball | Watertown | Home - Woodland Softball Field [Directions] | W 7-2 | ||
| Thu., 5/14 | JV Softball | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 5/14 | V Girls Tennis | Watertown | Home - Woodland High School Tennis courts [Directions] | L 3-4 | ||
| Sat., 5/16 | JV Baseball | Watertown | Away - Deland Field [Directions] | 11:00 a.m. | 9:30 a.m. | |
| Mon., 5/18 | V Baseball | Wolcott | Home - Woodland High School Baseball Field [Directions] | L 0-5 | ||
| Mon., 5/18 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Mon., 5/18 | V Boys Golf | Holy Cross, Wilby | Away [Directions] | Woodland 172 Holy Cross 174 Wilby Mike Erickson 37 Ryan Warner 44 Julian Perino 47 Will Flormann 44 | 2:10 p.m. | |
| Mon., 5/18 | V Boys Outdoor Track | Platt Tech, O'Brien Tech | Home - Woodland High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/18 | V Girls Outdoor Track | Platt Tech, O'Brien Tech | Home - Woodland High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/18 | V Softball | Wolcott | Away - George Babcock Field, Wolcott High School [Directions] | W 14-4 | 3:30 p.m. | |
| Mon., 5/18 | JV Softball | Wolcott | Away - Wolcott High School [Directions] | 5:15 p.m. | 3:30 p.m. | |
| Mon., 5/18 | V Girls Tennis | Holy Cross | Home - Woodland High School Tennis courts [Directions] | 3:30 p.m. | Qtr-Finals Team NVL Tournament | |
| Tue., 5/19 | V Softball | Hamden | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | W 5-4 | ||
| Tue., 5/19 | JV Softball | Hamden | Home - Woodland Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | V Baseball | Joel Barlow | Home - Woodland High School Baseball Field [Directions] | W 6-5 (9) | ||
| Wed., 5/20 | V Boys Golf | Crosby | Home - Oxford Greens [Directions] | Woodland 168 Crosby 265 Mike Erickson 37 Will Flormann 47 Ryan Warner 40 Zach Crowell 44 | 2:10 p.m. | |
| Wed., 5/20 | V Girls Tennis | Naugatuck | Home - Woodland High School Tennis courts [Directions] | TBA | NVL Girls Tennis Semi-Finals | |
| Thu., 5/21 | JV Baseball | Wolcott | Home - Woodland High School Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/21 | V Boys Golf | Chappa | Away | Mike Ryan 75 | ||
| Fri., 5/22 | FR Baseball | Bunnell | Home - Woodland High School Baseball Field [Directions] | 3:45 p.m. | ||
| Sat., 5/23 | V Softball | Oxford | Away - OHS Softball Field [Directions] | 1:30 p.m. | 12:00 p.m. | qtr finals NVL tournament |
| Sat., 5/23 | V Softball | Oxford | Away - OHS Softball Field [Directions] | 1:30 p.m. | 12:00 p.m. | qtr finals NVL tournament |
| Sat., 5/23 | V Girls Tennis | Watertown | Home - Woodland High School Tennis courts [Directions] | 11:00 a.m. | NVL Championships | |
| Tue., 5/26 | V Boys Outdoor Track | LJ/TJ NVL tournament trials | Away - Naugatuck High School Track | 3:15 p.m. | ||
| Tue., 5/26 | V Girls Tennis | NVL individual Championships | Home [Directions] | 12:00 p.m. | warm ups at 11am | |
| Wed., 5/27 | V Boys Golf | Waterbury Coop | Away - Western Hills [Directions] | Mike Erickson 39 Ryan Warner 42 Zach Crowell 42 Owen Harris 48 Woodland 171 Kennedy 238 | 2:10 p.m. | |
| Wed., 5/27 | V Boys Outdoor Track | NVL League Championshps | Away - Naugatuck High School Track | 3:30 p.m. | ||
| Wed., 5/27 | V Girls Outdoor Track | NVL League Championshps | Away - Naugatuck High School Track | 3:30 p.m. | ||
| Thu., 5/28 | V Baseball | Notre Dame-Fairfield (Scrim.) | Away - High School Field [Directions] | 4:00 p.m. | 2:20 p.m. | |
| Thu., 5/28 | V Baseball | Notre Dame-Fairfield (Scrim.) | Away - High School Field [Directions] | 4:00 p.m. | 2:20 p.m. | |
| Thu., 5/28 | V Boys Outdoor Track | NVL JV Tournament | Away | 3:30 p.m. | ||
| Thu., 5/28 | V Girls Outdoor Track | NVL JV Tournament | Away | 3:30 p.m. | ||
| Thu., 5/28 | V Girls Tennis | NVL Individual Championship Finals | Home - Woodland High School Tennis courts [Directions] | 1:00 p.m. | warm ups 12noon. | |
| Sat., 5/30 | V Softball | Thomaston (Scrim.) | Away - Black Rock Field [Directions] | 10:00 a.m. | 8?45 a.m. | |
| Mon., 6/1 | V Boys Golf | Sacred Heart | Away - East Mountain | Woodland 170 Sacred Heart 188 Mike Erickson 40 Ryan Warner 41 Owen Harris 45 Julian Perino 44 | 2:10 p.m. | |
| Thu., 6/4 | V Boys Golf | NVL Championships | Away - Watertown Golf Club | 8:00 a.m. | ||
| Thu., 6/4 | V Softball | Morgan | Away - Peters Complex [Directions] | 3:30 p.m. | 12:45 p.m. | |
| Tue., 6/9 | V Boys Golf | CIAC Div. Championship | Away [Directions] | TBA | ||
| Mon., 6/22 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||