| Woodland 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 527 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | V Baseball | Bullard Havens Tech (Scrim.) | Home - Woodland High School Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Seymour | Home - Woodland High School Baseball Field [Directions] | 10:00 a.m. | ||
| TBA | JV Baseball | Ansonia | Home - Woodland High School Baseball Field [Directions] | 3:30 p.m. | ||
| TBA | JV Baseball | Derby | Away - Derby -Ryan Athletic Complex-baseball field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| TBA | JV Baseball | Torrington | Home - Woodland High School Baseball Field [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Wolcott | Away - Wolcott High School [Directions] | TBA | 2:30 p.m. | |
| TBA | JV Baseball | Wilby | Away - Wilby H.S. [Directions] | TBA | 2:30 p.m. | |
| TBA | JV Baseball | Seymour | Away - French Park [Directions] | TBA | 9:00 a.m. | |
| TBA | JV Baseball | Derby | Home - Woodland High School Baseball Field [Directions] | TBA | ||
| TBA | FR Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | 2:30 p.m. | |
| TBA | FR Baseball | Seymour | Away - Seymour High School [Directions] | TBA | 2:30 p.m. | |
| TBA | FR Baseball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Boys Soccer | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Girls Soccer | Naugatuck | Away - Breen Field [Directions] | TBA | 2:30 p.m. | |
| TBA | JV Girls Soccer | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | V Softball | Nonnewaug (Scrim.) | Home - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Seymour | Away - Bungay School [Directions] | TBA | 2:45 | |
| TBA | JV Softball | Wilby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Softball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | TBA | 2:30 | |
| TBA | FR Softball | Naugatuck | Home - Woodland Softball Field [Directions] | 11:00 a.m. | ||
| TBA | V Girls Swimming and Diving | Oxford | Home - TBA [Directions] | TBA | 2:30 p.m. | |
| Tue., 8/27 | V Girls Soccer | Newtown (Scrim.) | Away - Treadwell Town Park--Tilson Field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Sat., 8/31 | V Boys Cross Country | West Haven Beach Run | Away - West Haven Beach | TBA | 9:30 a.m. | |
| Sat., 8/31 | V Boys Soccer | Shelton Jamboree | Away - Shelton HIgh School | 3:00 p.m. | 2:00 p.m. | |
| Sat., 8/31 | V Girls Cross Country | WEst Haven Beach Run | Away - West Haven Beach | TBA | ||
| Sat., 8/31 | V Girls Volleyball | East Haven Jamboree | Away - East Haven High School | 8:30 a.m. | TBA | |
| Thu., 9/5 | V Football | Bristol Eastern (Scrim.) | Away - Bristol Eastern High School [Directions] | 4:00 p.m. | 2:15 p.m. | |
| Fri., 9/6 | V Girls Soccer | Bloomfield Jamboree | Away - 330 Park Ave, Bloomfield | TBA | TBA | |
| Fri., 9/6 | V Girls Swimming and Diving | NVL Indicationals | Away - Kennedy | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/6 | V Girls Volleyball | Masuk (Scrim.) | Away - David Strong Gymnasium @ Masuk High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Tue., 9/10 | V Boys Cross Country | Bullard Havens Tech, Abbott Tech | Away - Wooster Cemetery, Danbury [Directions] | 3:30 p.m. | 2:15 p.m. | |
| Tue., 9/10 | V Boys Soccer | Crosby | Away - Crosby HS [Directions] | T 2-2 | 2:30 p.m. | |
| Tue., 9/10 | V Girls Cross Country | Abbott Tech, Bullard Havens Tech | Away - Wooster Cemetery, Danbury [Directions] | 3:30 p.m. | 2:15 p.m. | |
| Tue., 9/10 | V Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | W 3-2 | 3:45 p.m. | |
| Tue., 9/10 | JV Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | W 2-0 | 3:45 p.m. | |
| Wed., 9/11 | JV Boys Soccer | Crosby | Away - Crosby HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 9/12 | V Boys Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | L 7-0 | ||
| Thu., 9/12 | V Girls Volleyball | Watertown | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Thu., 9/12 | JV Girls Volleyball | Watertown | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Fri., 9/13 | V Football | Branford | Home - Woodland Football Field [Directions] | W 44-19 | ||
| Fri., 9/13 | JV Boys Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 9/13 | V Girls Soccer | Naugatuck | Away - Breen Field [Directions] | W 1-0 | 4:45 p.m. | |
| Fri., 9/13 | V Girls Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 7:00 p.m. | 4:45 p.m. | |
| Sat., 9/14 | JV Football | Branford | Home - Woodland Football Field [Directions] | 11:00 a.m. | ||
| Mon., 9/16 | V Boys Soccer | Oxford | Home - Woodland Soccer Field [Directions] | L 2-1 | ||
| Mon., 9/16 | V Girls Soccer | Seymour | Away - Seymour High Main Field [Directions] | W 1-0 | 4:45 p.m. | |
| Tue., 9/17 | V Boys Cross Country | Watertown, Sacred Heart, Wilby | Home - Woodland Track [Directions] | 3:30 p.m. | ||
| Tue., 9/17 | JV Boys Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Sacred Heart, Watertown, Wilby | Home - Woodland Track [Directions] | 3:30 p.m. | ||
| Tue., 9/17 | JV Girls Soccer | Seymour | Away - Seymour High Lower Field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 9/17 | V Girls Swimming and Diving | Suffield | Home - Woodland Pool [Directions] | 5:00 p.m. | ||
| Tue., 9/17 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 3-0 | 3:15 p.m. | |
| Tue., 9/17 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 2-0 | 3:15 p.m. | |
| Wed., 9/18 | FR Football | Crosby | Away - Crosby HS [Directions] | Cancelled | 2:15 p.m. | |
| Wed., 9/18 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | L 2-1 | 2:30 p.m. | |
| Wed., 9/18 | V Girls Soccer | Derby | Home - Woodland Soccer Field [Directions] | W 7-0 | ||
| Thu., 9/19 | JV Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 9/19 | JV Girls Soccer | Derby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 9/20 | V Football | Crosby | Home - Woodland Football Field [Directions] | W 40-6 | ||
| Fri., 9/20 | V Boys Soccer | Holy Cross | Home - Woodland Soccer Field [Directions] | L 3-0 | ||
| Fri., 9/20 | V Girls Soccer | Holy Cross | Away - Holy Cross HS [Directions] | L 1-2 | 2:30 p.m. | |
| Fri., 9/20 | V Girls Swimming and Diving | Torrington | Home - Woodland Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Seymour | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Fri., 9/20 | JV Girls Volleyball | Seymour | Home - Woodland High School Gym [Directions] | L 0-2 | ||
| Sat., 9/21 | JV Football | Crosby | Away - Crosby HS [Directions] | 11:00 a.m. | 9:30 p.m. | |
| Sat., 9/21 | JV Boys Soccer | Holy Cross | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Sat., 9/21 | JV Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 12:00 p.m. | 10:45 a.m. | |
| Mon., 9/23 | V Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | L 3-0 | 2:30 p.m. | |
| Tue., 9/24 | V Boys Cross Country | Wolcott, Holy Cross, St. Paul Catholic | Home - Woodland Track [Directions] | 3:30 p.m. | ||
| Tue., 9/24 | JV Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 9/24 | V Girls Cross Country | Wolcott, Holy Cross, St. Paul Catholic | Home - Woodland Track [Directions] | 3:30 p.m. | ||
| Tue., 9/24 | V Girls Soccer | Brookfield | Home - Woodland Soccer Field [Directions] | L 1-2 | ||
| Tue., 9/24 | JV Girls Soccer | Brookfield | Home - Beacon Falls Rec - Pent Field [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Girls Swimming and Diving | East Haven/Cross/Hillhouse/SHA | Home - Woodland Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 3-0 | 3:00 p.m. | |
| Tue., 9/24 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 2-0 | 3:00 p.m. | |
| Wed., 9/25 | V Boys Soccer | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | L 5-1 | 4:15 p.m. | |
| Wed., 9/25 | V Girls Soccer | Wolcott | Home - Woodland Soccer Field [Directions] | W 4-1 | ||
| Thu., 9/26 | FR Football | Kennedy | Home - Woodland Football Field [Directions] | 3:30 p.m. | ||
| Thu., 9/26 | JV Boys Soccer | Wolcott | Away - Wolcott High School, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/26 | JV Girls Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 9/26 | V Girls Volleyball | Torrington | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Thu., 9/26 | JV Girls Volleyball | Torrington | Home - Woodland High School Gym [Directions] | W 2-1 | ||
| Fri., 9/27 | V Boys Soccer | Sacred Heart | Away - Bucks Hill Park | W 3-2 | 2:30 p.m. | |
| Fri., 9/27 | V Girls Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | W 7-1 | ||
| Fri., 9/27 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Fri., 9/27 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 3-1 | 3:30 p.m. | |
| Fri., 9/27 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 2-0 | 3:30 p.m. | |
| Sat., 9/28 | V Boys Cross Country | Wilton Invitational | Away - Wilton HIgh School | TBA | 7:30 p.m. | |
| Sat., 9/28 | V Football | Kennedy | Away - Municipal Stadium [Directions] | W 34-26 | 7:30 a.m. | |
| Sat., 9/28 | JV Boys Soccer | Sacred Heart | Away - Bucks Hill Park | Cancelled | ||
| Sat., 9/28 | V Girls Cross Country | Wilton Invitational | Away - Wilton High School | TBA | 7:30 a.m. | |
| Sat., 9/28 | JV Girls Soccer | Sacred Heart | Home - Woodland Softball Field [Directions] | 10:30 a.m. | ||
| Tue., 10/1 | V Boys Cross Country | Naugatuck, Seymour, Crosby | Away - Seymour High School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 10/1 | V Boys Soccer | Watertown | Home - Woodland Soccer Field [Directions] | L 2-7 | ||
| Tue., 10/1 | V Girls Cross Country | Seymour, Naugatuck, Crosby | Away - Seymour High School [Directions] | 3:30 p.m. | ||
| Tue., 10/1 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | T 0-0 | 2:30 p.m. | |
| Tue., 10/1 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 10/1 | V Girls Volleyball | Crosby | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Tue., 10/1 | JV Girls Volleyball | Crosby | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Wed., 10/2 | JV Boys Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 10/2 | JV Girls Soccer | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Wed., 10/2 | V Girls Volleyball | East Haven | Away - East Haven High School [Directions] | W 3-0 | 3:45 p.m. | |
| Wed., 10/2 | JV Girls Volleyball | East Haven | Away - East Haven High School [Directions] | L 0-2 | 3:45 p.m. | |
| Fri., 10/4 | V Football | Naugatuck | Home - Woodland Football Field [Directions] | W 25-22 | ||
| Fri., 10/4 | V Boys Soccer | Ansonia | Home - Woodland Soccer Field [Directions] | W 3-2 | ||
| Fri., 10/4 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | W 3-2 | 2:30 p.m. | |
| Fri., 10/4 | V Girls Swimming and Diving | Naugatuck | Home - Woodland Pool [Directions] | 6:00 p.m. | ||
| Fri., 10/4 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | W 3-1 | 3:45 p.m. | |
| Fri., 10/4 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | W 2-0 | 3:45 p.m. | |
| Sat., 10/5 | JV Football | Naugatuck | Away - Naugatuck High School [Directions] | 2:00 p.m. | 12:15 p.m. | |
| Sat., 10/5 | JV Boys Soccer | Ansonia | Home - Woodland Soccer Field [Directions] | 12:00 p.m. | ||
| Sat., 10/5 | JV Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 10:00 a.m. | 8:45 a.m. | |
| Tue., 10/8 | V Boys Cross Country | Torrington, Kennedy | Away - Torrington High School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 10/8 | V Boys Soccer | Torrington | Home - Woodland Soccer Field [Directions] | L 0-4 | ||
| Tue., 10/8 | V Girls Cross Country | Torrington, Kennedy | Away - Torrington HIgh School [Directions] | 3:30 p.m. | TBA | |
| Tue., 10/8 | V Girls Soccer | Torrington | Away - Torrington High School [Directions] | W 3-2 | 4:30 p.m. | |
| Tue., 10/8 | V Girls Volleyball | Wilby | Home - Woodland High School Gym [Directions] | W 3-0 | 3:30 p.m. | |
| Tue., 10/8 | JV Girls Volleyball | Wilby | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Wed., 10/9 | V Boys Soccer | Kennedy | Away - West Side Middle School [Directions] | L 5-8 | 2:30 p.m. | |
| Wed., 10/9 | V Girls Swimming and Diving | Seymour | Home - Woodland Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | FR Football | St. Paul Catholic | Home - Woodland Football Field [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | JV Girls Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Thu., 10/10 | JV Girls Soccer | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Thu., 10/10 | V Girls Volleyball | Naugatuck | Away - Naugatuck High School [Directions] | L 1-3 | 3:30 p.m. | |
| Thu., 10/10 | JV Girls Volleyball | Naugatuck | Away - Naugatuck High School [Directions] | W 2-1 | 3:30 p.m. | |
| Fri., 10/11 | V Boys Soccer | St. Paul Catholic | Away - Farmington Soccer Academy [Directions] | L 3-2 | 5:00 p.m. | |
| Fri., 10/11 | V Girls Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | W 4-0 | ||
| Fri., 10/11 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy High School Pool | 7:00 p.m. | 5:30 p.m. | |
| Fri., 10/11 | V Girls Volleyball | Ansonia | Home - Woodland High School Gym [Directions] | W 3-1 | ||
| Fri., 10/11 | JV Girls Volleyball | Ansonia | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Sat., 10/12 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 59-14 | 10:15 a.m. | bus pick up at Prospect Fire Hall |
| Sat., 10/12 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 10:30 a.m. | 8:45 a.m. | bus pick up from Laurel Ledge/BF |
| Mon., 10/14 | JV Girls Soccer | Seymour | Home - Pent Field, Beacon Falls [Directions] | 10:30 a.m. | ||
| Tue., 10/15 | JV Boys Soccer | Kennedy | Away - West Side Middle School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 10/15 | V Girls Soccer | Seymour | Home - Woodland Soccer Field [Directions] | W 2-0 | ||
| Tue., 10/15 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Boys Cross Country | NVL Championships | Away - Veteran's park | 3:30 p.m. | 12:45 p.m. | |
| Wed., 10/16 | V Boys Soccer | Seymour | Home - Woodland Soccer Field [Directions] | L 2-6 | ||
| Wed., 10/16 | V Girls Cross Country | NVL Championshps | Away - Veteran's Park | 3:30 p.m. | TBA | |
| Wed., 10/16 | V Girls Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | W 2-1 | ||
| Wed., 10/16 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 3-0 | 2:20 p.m. | |
| Wed., 10/16 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 2-0 | 2:20 p.m. | |
| Thu., 10/17 | JV Boys Soccer | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 10/18 | V Boys Cross Country | NVL Novice Race | Home - Woodland Track [Directions] | TBA | ||
| Fri., 10/18 | V Football | Pomperaug | Away - Sports Complex & Track [Directions] | W 42-13 | 4:30 p.m. | |
| Fri., 10/18 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | L 0-3 | 3:45 p.m. | |
| Fri., 10/18 | V Girls Cross Country | NVL Novice Race | Home - Woodland Track [Directions] | 3:30 p.m. | ||
| Fri., 10/18 | V Girls Soccer | Watertown | Home - Woodland Soccer Field [Directions] | W 2-0 | ||
| Fri., 10/18 | V Girls Swimming and Diving | Sheehan | Home - Woodland Pool [Directions] | 5:00 p.m. | Senior Night | |
| Fri., 10/18 | V Girls Volleyball | Wolcott | Home - Woodland High School Gym [Directions] | W 3-1 | ||
| Fri., 10/18 | JV Girls Volleyball | Wolcott | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Sat., 10/19 | JV Football | Pomperaug | Home - Woodland Football Field [Directions] | 12:30 p.m. | ||
| Sat., 10/19 | JV Girls Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 10:30 a.m. | ||
| Mon., 10/21 | V Boys Cross Country | Platt Tech Invitational | Away - Eisenhower Park, Milford | 3:30 p.m. | 2pm | |
| Mon., 10/21 | V Boys Soccer | Wolcott | Home - Woodland Football Field [Directions] | W 3-2 | Senior Night | |
| Mon., 10/21 | V Girls Cross Country | Platt Tech Invitational | Away - Eisenhower Park, Milford | 3:30 p.m. | 2:00 p.m. | |
| Mon., 10/21 | V Girls Soccer | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | L 0-2 | 4:30 p.m. | |
| Mon., 10/21 | V Girls Volleyball | Seymour | Away - Seymour High School [Directions] | W 3-1 | 3:45 p.m. | |
| Mon., 10/21 | JV Girls Volleyball | Seymour | Away - Seymour High School [Directions] | L 1-2 | 3:45 p.m. | |
| Tue., 10/22 | JV Boys Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Tue., 10/22 | JV Girls Soccer | Wolcott | Away - Wolcott High School, Lower Soccer Field [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Tue., 10/22 | V Girls Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Wed., 10/23 | JV Boys Soccer | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Wed., 10/23 | V Girls Soccer | Naugatuck | Home - Woodland Football Field [Directions] | L 1-4 | SENIOR NIGHT | |
| Wed., 10/23 | V Girls Volleyball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Wed., 10/23 | JV Girls Volleyball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | W 2-0 | ||
| Thu., 10/24 | JV Girls Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Thu., 10/24 | V Girls Volleyball | Amity | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Thu., 10/24 | JV Girls Volleyball | Amity | Home - Woodland High School Gym [Directions] | W 2-1 | ||
| Fri., 10/25 | V Football | Sacred Heart | Home - Woodland Football Field [Directions] | W 54-6 | ||
| Fri., 10/25 | JV Girls Volleyball | NHS JV Tournament | Away - Naugatuck High School | 3:30 p.m. | 2:30 p.m. | |
| Sat., 10/26 | V Boys Cross Country | STate Meet | Away - Wickham Park, Manchester | TBA | 8:15 a.m. | |
| Sat., 10/26 | V Girls Soccer | St. Paul Catholic | Away - Naugatuck High School [Directions] | W 4-1 | 11:45 | |
| Sat., 10/26 | V Girls Volleyball | Kennedy | Home - Woodland High School Gym [Directions] | W 3-0 | ||
| Mon., 10/28 | V Girls Cross Country | State Meet | Away - Wickham Park, Manchester | TBA | 8:15 a.m. | |
| Tue., 10/29 | V Girls Swimming and Diving | NVL Tournament Trials | Away - Kennedy High School | 4:00 p.m. | TBA | |
| Tue., 10/29 | V Girls Volleyball | Wolcott | Away - Wilby High School [Directions] | W 3-0 | TBA | |
| Wed., 10/30 | V Girls Swimming and Diving | NVL Diving Championships | Away - Kennedy High School | 6:00 p.m. | ||
| Fri., 11/1 | V Football | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | L 18-37 | 4:30 p.m. | |
| Fri., 11/1 | V Girls Volleyball | Joel Barlow (Scrim.) | Away - Lower Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Sat., 11/2 | JV Football | Holy Cross | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 11/2 | V Girls Swimming and Diving | NVL Finals | Away - Kennedy | 4:00 p.m. | TBA | |
| Mon., 11/4 | V Girls Soccer | Windham | Home - Woodland Soccer Field [Directions] | W 2-0 | ||
| Tue., 11/5 | V Girls Volleyball | Cheshire (Scrim.) | Home - Woodland High School Gym [Directions] | 3:00 p.m. | ||
| Wed., 11/6 | V Girls Soccer | Plainfield | Home - Woodland High School [Directions] | 2:00 p.m. | ||
| Wed., 11/6 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Wed., 11/6 | V Girls Volleyball | East Catholic | Home - Woodland High School Gym [Directions] | 6:30 p.m. | ||
| Wed., 11/6 | V Girls Volleyball | Winner E. Catholic/Weston | Home - Woodland High School Gym [Directions] | 7:00 p.m. | ||
| Fri., 11/8 | V Football | Torrington | Home - Woodland Football Field [Directions] | W 46-14 | ||
| Sat., 11/9 | JV Football | Torrington | Away - Torrington High School [Directions] | 10:00 a.m. | 8:15 a.m. | |
| Sat., 11/9 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 2:00 p.m. | ||
| Wed., 11/13 | V Girls Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 7:00 p.m. | ||
| Fri., 11/15 | V Football | Derby | Home - Woodland Football Field [Directions] | W 32-27 | ||
| Fri., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 11/16 | JV Football | Derby | Away - Ryan Athletic Complex-Deflippo Field [Directions] | 10:00 a.m. | 8:15 a.m. | |
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Sat., 11/23 | JV Football | Seymour | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Fri., 11/29 | V Football | Seymour | Away - Seymour High Main Field [Directions] | W 22-19 | 3:30 p.m. | |
| Sat., 11/30 | V Girls Basketball | East Haven Tri-Scrimmage | Away - East Haven High School | 10:00 a.m. | 8:15 a.m. | |
| Mon., 12/9 | V Boys Indoor Track | Wesleyan Developmental | Away - WEsleyan University | TBA | 3:00 | |
| Wed., 12/11 | V Girls Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | L 62-31 | ||
| Wed., 12/11 | JV Girls Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/13 | V Boys Swimming and Diving | NVL Indicationals | Away - Kennedy High School | 4:00 p.m. | 2:00 p.m. | |
| Sat., 12/14 | V Boys Indoor Track | Wilton Invitational | Away - Wilton High School | TBA | 7:30 a.m. | |
| Sat., 12/14 | V Wrestling | Southington (Scrim.) | Away - Southington HS [Directions] | 9:00 a.m. | 8:00 a.m. | |
| Wed., 12/18 | V Boys Basketball | Sacred Heart | Home - Woodland High School Gym [Directions] | L 44-75 | ||
| Wed., 12/18 | JV Boys Basketball | Sacred Heart | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Boys Basketball | Sacred Heart | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/18 | V Boys Swimming and Diving | Sacred Heart | Home - Woodland High School Pool [Directions] | Sacred heart 91 Woodland 81 | ||
| Wed., 12/18 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | L 49-24 | 4:30 p.m. | |
| Wed., 12/18 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:30 p.m. | 4:30 p.m. | |
| Thu., 12/19 | FR Boys Basketball | Crosby | Home - Woodland High School Gym [Directions] | 7:00 p.m. | ||
| Thu., 12/19 | V Boys Indoor Track | Glastonbury Developmental | Away - Glastonbury High School | 4:00 p.m. | 3:00 p.m. | two buses |
| Thu., 12/19 | V Wrestling | Xavier | Home - Amity High School [Directions] | Xavier 65 Amity 6 Loss | ||
| Fri., 12/20 | V Boys Basketball | Crosby | Home - Woodland High School Gym [Directions] | L 42-97 | ||
| Fri., 12/20 | JV Boys Basketball | Crosby | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | V Girls Basketball | Crosby | Away - Crosby HS [Directions] | L 43-61 | 4:15 p.m. | |
| Fri., 12/20 | JV Girls Basketball | Crosby | Away - Crosby HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Sat., 12/21 | V Wrestling | Shelton Invitational | Away | Amity 5th Place | 8:00 | |
| Sat., 12/21 | V Wrestling | Southington JV Tournamnent | Away - Southington HS | Cancelled | ||
| Mon., 12/23 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | L 52-57 | 4:00 p.m. | |
| Mon., 12/23 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Mon., 12/23 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Mon., 12/23 | V Wrestling | Branford | Away - James L MacVeigh Alumni Athletic Complex - Gym [Directions] | Branford 46-Amity 26 Loss | 12:30 p.m. | |
| Mon., 12/23 | V Girls Basketball | Wolcott | Home - Woodland High School Gym [Directions] | L 34-39 | ||
| Mon., 12/23 | JV Girls Basketball | Wolcott | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/26 | V Boys Basketball | Ansonia | Home - Oxford High School [Directions] | W 55-47 | 3:30 p.m. | Candy Cane Classic Tournament at Oxford HS - semi-finals |
| Thu., 12/26 | V Girls Basketball | Ansonia | Away - Ansonia High School [Directions] | W 41-34 | 5:45 p.m. | Candy Cane Classic Tournament |
| Fri., 12/27 | V Boys Basketball | Amity | Away - Oxford High School [Directions] | L 51-79 | TBA | Consolation game at 5pm: Championship game at 7pm |
| Fri., 12/27 | V Girls Basketball | Amity | Away - Ansonia High School [Directions] | L 26-57 | TBA | consolation game 5pm: Championship 7pm |
| Sat., 12/28 | V Wrestling | Danbury Holiday Tournament | Away - Danbury HS | 10:00 a.m. | 6:30 a.m. | |
| Sat., 1/4 | V Wrestling | Southington Duals | Away - Southington HS | 10:00 a.m. | 8:00 a.m. | |
| Sat., 1/4 | V Wrestling | Bristol Eastern JV Tournament | Away - Bristol Eastern HS | Cancelled | . | |
| Tue., 1/7 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | L 45-51 | 4:15 p.m. | |
| Tue., 1/7 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Tue., 1/7 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 1/7 | V Boys Swimming and Diving | Naugatuck | Home - Woodland High School Pool [Directions] | Naugatuck 93 Woodland 76 | ||
| Tue., 1/7 | V Girls Basketball | Holy Cross | Home - Woodland High School Gym [Directions] | L 33-50 | ||
| Tue., 1/7 | JV Girls Basketball | Holy Cross | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/8 | V Wrestling | Guilford | Away - Kenefick Gymnasium at GHS [Directions] | Guilford 37 Amity 31 Loss | 5:00 | |
| Thu., 1/9 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 58-42 | 4:15 p.m. | |
| Thu., 1/9 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Thu., 1/9 | FR Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Thu., 1/9 | V Girls Basketball | Watertown | Home - Woodland High School Gym [Directions] | L 29-42 | ||
| Thu., 1/9 | JV Girls Basketball | Watertown | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/11 | V Boys Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | L 47-64 | ||
| Sat., 1/11 | JV Boys Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/11 | FR Boys Basketball | Naugatuck | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Sat., 1/11 | V Boys Indoor Track | SCC Coaches invitational | Away - Hillhouse | TBA | optional/Transportation not provided by Region 16 | |
| Sat., 1/11 | V Wrestling | Natick Invitational | Away - Natick, Mass | 10:00 a.m. | 5:30 a.m. | |
| Sat., 1/11 | V Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | W 35-32 (OT) | 4:30 p.m. | |
| Sat., 1/11 | JV Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | 4:30 p.m. | |
| Tue., 1/14 | V Boys Basketball | Seymour | Home - Woodland High School Gym [Directions] | W 70-51 | ||
| Tue., 1/14 | JV Boys Basketball | Seymour | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | FR Boys Basketball | Seymour | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/14 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 1/14 | V Wrestling | Cheshire | Away - Cheshire High East Gym [Directions] | Amity 45 Cheshire 39 Win | 4:30 | |
| Tue., 1/14 | V Girls Basketball | Seymour | Away - Seymour High School [Directions] | L 34-44 | 4:15 p.m. | |
| Tue., 1/14 | JV Girls Basketball | Seymour | Away - Seymour High School [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Fri., 1/17 | V Boys Basketball | Wilby | Home - Woodland High School Gym [Directions] | L 52-53 | ||
| Fri., 1/17 | FR Boys Basketball | Wilby | Home - Woodland High School Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Seymour | Away - Seymour High School [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Fri., 1/17 | V Girls Basketball | Wilby | Home - Woodland High School Gym [Directions] | W 42-40 | ||
| Sat., 1/18 | JV Boys Basketball | Wilby | Home - Woodland High School Gym [Directions] | 11:00 a.m. | ||
| Sat., 1/18 | V Wrestling | New Milford Tournament | Away - New Milford HS | 9:00 a.m. | 5:45 a.m. | |
| Sat., 1/18 | V Wrestling | Xavier JV TOurnament | Away - Xavier HS | 9:00 a.m. | 7:00 a.m. | |
| Sat., 1/18 | JV Girls Basketball | Wilby | Home - Woodland High School Gym [Directions] | 9:30 a.m. | ||
| Wed., 1/22 | V Wrestling | East Haven | Home - Amity High School [Directions] | Amity 60 East Haven 21 Win | ||
| Thu., 1/23 | V Boys Basketball | Derby | Away - Derby High -A. Vitello Gymnasium [Directions] | L 66-69 | 4:30 p.m. | |
| Thu., 1/23 | JV Boys Basketball | Derby | Away - Derby High -A. Vitello Gymnasium [Directions] | 5:30 p.m. | 4:30 p.m. | |
| Thu., 1/23 | V Girls Basketball | Derby | Home - Woodland High School Gym [Directions] | L 45-47 (OT) | ||
| Thu., 1/23 | JV Girls Basketball | Derby | Home - Woodland High School Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/24 | V Boys Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | W 49-41 | ||
| Fri., 1/24 | JV Boys Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/24 | FR Boys Basketball | St. Paul Catholic | Home - Woodland High School Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | 5:45 p.m. | |
| Fri., 1/24 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 27-58 | 3:45 p.m. | |
| Fri., 1/24 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:15 p.m. | 3:45 p.m. | |
| Sat., 1/25 | V Wrestling | Morgan Duals | Away - Morgan HS, Clinton | Cancelled | 7:00 a.m. | |
| Sat., 1/25 | V Wrestling | Ridgefield Challenge | Away - Ridgefield HS | 9:00 a.m. | 6:00 a.m. | |
| Tue., 1/28 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 48-61 | 4:15 p.m. | |
| Tue., 1/28 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Tue., 1/28 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 1/28 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Tue., 1/28 | V Girls Basketball | Kennedy | Home - Woodland High School Gym [Directions] | L 36-54 | ||
| Tue., 1/28 | JV Girls Basketball | Kennedy | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/29 | V Wrestling | Fairfield Prep | Home - Amity High School [Directions] | Amity 49 Fairfield Prep 19 Win | ||
| Fri., 1/31 | V Boys Basketball | Torrington | Home - Woodland High School Gym [Directions] | W 75 - 72 | ||
| Fri., 1/31 | JV Boys Basketball | Torrington | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | Torrington | Home - Woodland High School Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Holy Cross | Home - Woodland High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Torrington | Away - Torrington High School [Directions] | L 18-58 | 4:00 p.m. | |
| Fri., 1/31 | JV Girls Basketball | Torrington | Away - Torrington High School [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Tue., 2/4 | V Boys Basketball | Wolcott | Home - Woodland High School Gym [Directions] | L 49-58 | ||
| Tue., 2/4 | JV Boys Basketball | Wolcott | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Boys Basketball | Wolcott | Home - Woodland High School Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/4 | V Wrestling | Jonathan Law | Away - Jonathan Law New Gym [Directions] | Amity46 Jonathan Law 23 Win | 5:00 | |
| Tue., 2/4 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | L 44-66 | 4:00 p.m. | |
| Tue., 2/4 | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Thu., 2/6 | V Boys Swimming and Diving | Northwestern | Home - Woodland High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | V Wrestling | Shelton | Away - Shelton HS [Directions] | Amity 39 Shelton 33 Win | 5:00 | |
| Fri., 2/7 | V Boys Basketball | Ansonia | Away - Ansonia High School [Directions] | W 60 - 51 | 4:15 p.m. | |
| Fri., 2/7 | JV Boys Basketball | Ansonia | Away - Ansonia High School [Directions] | 4:30 p.m. | 4:15 p.m. | |
| Fri., 2/7 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby H.S. [Directions] | 4:00 p.m. | 4:30 p.m. | |
| Fri., 2/7 | V Girls Basketball | Ansonia | Home - Woodland High School Gym [Directions] | W 49-29 | ||
| Fri., 2/7 | JV Girls Basketball | Ansonia | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/8 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 2/8 | V Wrestling | Foran Dual Tournament | Away - Foran HS | Amity 2nd Place | 7:00 | |
| Sat., 2/8 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Tue., 2/11 | V Boys Basketball | Watertown | Home - Woodland High School Gym [Directions] | L 59-55 | ||
| Tue., 2/11 | JV Boys Basketball | Watertown | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | FR Boys Basketball | Watertown | Home - Woodland High School Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/11 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | L 21-44 | 4:15 p.m. | |
| Tue., 2/11 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Wed., 2/12 | V Boys Basketball | Seymour | Away - Seymour Middle School [Directions] | W 55-30 | 4:15 p.m. | |
| Wed., 2/12 | JV Boys Basketball | Seymour | Away - Seymour Middle School [Directions] | 5:45 p.m. | 4:15 p.m. | |
| Wed., 2/12 | FR Boys Basketball | Seymour | Away - Seymour High School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 2/12 | V Boys Swimming and Diving | Kennedy | Home - Woodland High School Pool [Directions] | 6:00 p.m. | ||
| Wed., 2/12 | V Wrestling | New Haven Wrestling | Away - Wilbur Cross Gym [Directions] | 6:00 p.m. | 4:30 | |
| Wed., 2/12 | V Girls Basketball | Seymour | Home - Woodland High School Gym [Directions] | W 31-24 | ||
| Wed., 2/12 | JV Girls Basketball | Seymour | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/14 | V Wrestling | SCC JV Tournament | Away - Shelton HS | TBA | TBA | |
| Sat., 2/15 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/15 | V Wrestling | SCC Varsity Tournament | Away - Shelton HS | 9:00 a.m. | 6:30 a.m. | |
| Sat., 2/15 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/17 | V Wrestling | NFA JV States | Away | Cancelled | 7:00 | |
| Thu., 2/20 | V Boys Basketball | Derby | Home - Woodland High School Gym [Directions] | W 80 - 54 | ||
| Thu., 2/20 | JV Boys Basketball | Derby | Home - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/20 | V Boys Swimming and Diving | Masuk | Home - Woodland High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 2/20 | V Girls Basketball | Derby | Away - Derby High- A. Vitello Gymnasium [Directions] | W 43-32 | 4:15 p.m. | |
| Thu., 2/20 | JV Girls Basketball | Derby | Away - Derby High- A. Vitello Gymnasium [Directions] | 7:00 p.m. | 4:30 p.m. | |
| Fri., 2/21 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 67 - -58 | 4:00 p.m. | |
| Fri., 2/21 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Fri., 2/21 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 2/21 | V Wrestling | CIAC Class LL Tournament | Away - Trumbull HS | 4:00 p.m. | 2:30 | |
| Sat., 2/22 | V Wrestling | CIAC Class LL Tournament | Away - Trumbull HS | 9:00 a.m. | 8:00 a.m. | |
| Fri., 2/28 | V Wrestling | CIAC Open Championship | Away - NH Athletic Center (Floyd Little) | 4:00 p.m. | ||
| Sat., 3/1 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Sat., 3/1 | V Wrestling | CIAC Open Championship | Away | TBA | ||
| Sat., 3/1 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Tue., 3/4 | V Boys Swimming and Diving | NVL Trials | Away - Kennedy High School Pool | 4:00 p.m. | TBA | |
| Wed., 3/5 | V Boys Basketball | Holy Cross (Scrim.) | Home - Woodland High School Gym [Directions] | 4:30 p.m. | ||
| Wed., 3/5 | V Boys Swimming and Diving | NVL Diving championships | Away | 6:00 p.m. | ||
| Fri., 3/7 | V Boys Swimming and Diving | NVL Championship Finals | Away - TBA | 4:00 p.m. | TBA | |
| Fri., 3/7 | V Wrestling | New England Championship | Away | TBA | TBA | |
| Sat., 3/8 | V Wrestling | New England Championship | Away | TBA | TBA | |
| Tue., 3/11 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | 4:15 p.m. | |
| Wed., 3/12 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 3/15 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 3:30 p.m. | ||
| Tue., 3/18 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 7:15 p.m. | ||
| Thu., 3/20 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/22 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Sat., 3/29 | V Baseball | Oxford (Scrim.) | Home - Beacon Falls Rec - Pent Field [Directions] | 10:00 a.m. | ||
| Tue., 4/1 | V Softball | Masuk (Scrim.) | Home - Woodland Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/2 | V Softball | Kolbe Cathedral (Scrim.) | Away - Seaside Park [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 4/3 | V Baseball | O'Brien Tech (Scrim.) | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 4/3 | V Boys Tennis | Masuk (Scrim.) | Away - Wolfe Park Tennis Courts [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 4/3 | V Girls Tennis | Masuk (Scrim.) | Home - Woodland High School Tennis courts [Directions] | 3:45 p.m. | ||
| Sun., 4/6 | V Baseball | Maine | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 1:00 p.m. | ||
| Sun., 4/6 | V Baseball | Maine | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:00 p.m. | ||
| Sun., 4/6 | V Softball | Nonnewaug (Scrim.) | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 1:00 p.m. | ||
| Sun., 4/6 | V Softball | Maine | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:00 p.m. | ||
| Mon., 4/7 | V Baseball | Oxford (Scrim.) | Away - OHS Baseball Field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Mon., 4/7 | V Boys Tennis | Shelton (Scrim.) | Home - Woodland High School Tennis courts [Directions] | 3:45 p.m. | ||
| Mon., 4/7 | V Softball | Oxford (Scrim.) | Away - OHS Softball Field [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Mon., 4/7 | V Girls Tennis | Shelton (Scrim.) | Away - Shelton High School Tennis Courts [Directions] | 3:45 p.m. | 2:50 p.m. | |
| Wed., 4/9 | V Baseball | Sacred Heart | Home - Woodland High School Baseball Field [Directions] | W 5-2 | ||
| Wed., 4/9 | V Boys Outdoor Track | Kaynor Tech, Bullard Havens Tech | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Wed., 4/9 | V Boys Tennis | Sacred Heart | Home - Woodland High School Tennis courts [Directions] | L 3-6 | ||
| Wed., 4/9 | V Girls Outdoor Track | Kaynor Tech, Bullard Havens Tech | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Wed., 4/9 | V Softball | Sacred Heart | Away - Huntingdon Park | W 10-3 | 2:30 p.m. | |
| Wed., 4/9 | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | 3:30 p.m. | 2:30 | |
| Wed., 4/9 | V Girls Tennis | Sacred Heart | Away - Fulton Park | W 7-0 | 2:50 p.m. | |
| Thu., 4/10 | JV Baseball | Sacred Heart | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 4/10 | V Girls Tennis | Crosby | Home - Woodland High School Tennis courts [Directions] | W 7-0 | ||
| Fri., 4/11 | V Baseball | Crosby | Home - Woodland High School Baseball Field [Directions] | W 7-1 | ||
| Fri., 4/11 | V Boys Tennis | Naugatuck | Away - Naugatuck High School [Directions] | L 0-9 | 8:45 a.m. | |
| Fri., 4/11 | V Softball | Crosby | Away - Huntington Park [Directions] | W 18-2 | 2:30 p.m. | |
| Fri., 4/11 | JV Softball | Crosby | Away - Huntington Park [Directions] | 3:30 p.m. | 2:30 | |
| Sat., 4/12 | JV Baseball | Crosby | Home - Woodland High School Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/12 | V Boys Outdoor Track | Bellringer Invitational | Away - East Hampton High School | TBA | TBA (1 or 2 buses) | QUALIFIERS ONLY |
| Sat., 4/12 | V Softball | New Canaan | Home - Woodland Softball Field [Directions] | W 8-0 | ||
| Mon., 4/14 | V Baseball | Wolcott | Away - Wolcott High School [Directions] | W 9-6 | 2:30 p.m. | |
| Mon., 4/14 | FR Baseball | Wolcott | Away - BAW [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Mon., 4/14 | V Boys Tennis | Wolcott | Home - Woodland High School Tennis courts [Directions] | L 0-9 | ||
| Mon., 4/14 | V Softball | Wolcott | Home - Woodland Softball Field [Directions] | W 12-0 | ||
| Mon., 4/14 | JV Softball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Mon., 4/14 | V Girls Tennis | Wolcott | Away - Wolcott High School [Directions] | W 5-2 | 2:50 p.m. | |
| Tue., 4/15 | V Girls Outdoor Track | Seymour, Kennedy, Wilby | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Thu., 4/17 | V Baseball | Naugatuck | Home - Woodland High School Baseball Field [Directions] | L 1-6 | ||
| Thu., 4/17 | FR Baseball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 1:00 p.m. | ||
| Thu., 4/17 | V Boys Outdoor Track | Seymour, Kennedy, Wilby | Home - Woodland High School Track [Directions] | 10:00 a.m. | ||
| Thu., 4/17 | V Boys Outdoor Track | NVL NOVICE MEET | Home - Woodland High School Track [Directions] | TBA | ||
| Thu., 4/17 | V Boys Tennis | Naugatuck | Home - Woodland High School Tennis courts [Directions] | L 3-6 | ||
| Thu., 4/17 | V Softball | Naugatuck | Away - Breen Field [Directions] | W 6-5 | 9:30 a.m. | |
| Thu., 4/17 | JV Softball | Naugatuck | Away - Breen Field [Directions] | 11:00 a.m. | 9:30 a.m. | |
| Thu., 4/17 | V Girls Tennis | Naugatuck | Away - Naugatuck High School [Directions] | W 4-3 | 2:50 p.m. | |
| Fri., 4/18 | JV Baseball | Naugatuck | Home - Woodland High School Baseball Field [Directions] | 10:00 a.m. | ||
| Fri., 4/18 | FR Softball | Naugatuck | Away - Breen Field [Directions] | 10:00 a.m. | ||
| Sat., 4/19 | V Baseball | Ansonia | Home - Woodland High School Baseball Field [Directions] | W 4-3 | ||
| Sat., 4/19 | FR Baseball | Ansonia | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 1:00 p.m. | ||
| Mon., 4/21 | V Baseball | Holy Cross | Away - HCHS [Directions] | L 6-3 | 2:30 p.m. | |
| Mon., 4/21 | FR Baseball | Holy Cross | Away - Upper Murray Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Mon., 4/21 | V Boys Golf | Holy Cross, Waterbury Coop | Away [Directions] | Woodland 52 46 50 54 Holy Cross 45 49 48 49 Kennedy 63 56 66 72 | 1:30 p.m. | |
| Mon., 4/21 | V Boys Tennis | Holy Cross | Away - HCHS [Directions] | L 3-6 | 2:30 p.m. | |
| Mon., 4/21 | V Softball | Holy Cross | Home - Woodland Softball Field [Directions] | L 5-6 | ||
| Mon., 4/21 | JV Softball | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Mon., 4/21 | V Girls Tennis | Ansonia | Home - Woodland High School Tennis courts [Directions] | W 7-0 | ||
| Tue., 4/22 | JV Baseball | Holy Cross | Away - HCHS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 4/22 | V Boys Golf | St. Paul Catholic, Crosby | Away - Chippanee Golf Club [Directions] | Woodland 42 46 62 50 St. Paul 47 44 44 45 Crosby 59 70 70 70 | 1:30 p.m. | |
| Tue., 4/22 | V Boys Outdoor Track | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 4/22 | V Boys Tennis | Crosby | Away - Woodland HS [Directions] | L 2-7 | 2:30 p.m. | |
| Tue., 4/22 | V Girls Outdoor Track | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | ||
| Tue., 4/22 | FR Softball | Holy Cross | Away - Lower Murray Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 4/23 | V Baseball | Watertown | Away - Deland Field [Directions] | L 5-7 | 2:30 p.m. | |
| Wed., 4/23 | FR Baseball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Wed., 4/23 | V Softball | Watertown | Home - Woodland Softball Field [Directions] | W 1-0 | ||
| Wed., 4/23 | JV Softball | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 4/23 | V Girls Tennis | Watertown | Home - Woodland High School Tennis courts [Directions] | W 4-3 | ||
| Thu., 4/24 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Thu., 4/24 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | Woodland 200 49 43 52 56 Watertown 215 50 54 51 60 | 2:05 p.m. | |
| Thu., 4/24 | V Boys Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | W 5-4 | 2:30 p.m. | |
| Thu., 4/24 | V Girls Tennis | Seymour | Away - Seymour High School [Directions] | W 6-1 | 2:50 p.m. | |
| Fri., 4/25 | V Baseball | Seymour | Home - Woodland High School Baseball Field [Directions] | L 0-1 | ||
| Fri., 4/25 | FR Baseball | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 4/25 | V Boys Tennis | Crosby | Home - Woodland High School Tennis courts [Directions] | L 1-8 | ||
| Fri., 4/25 | V Softball | Seymour | Away - Seymour High School [Directions] | L 1-12 | 2:45 p.m. | |
| Sat., 4/26 | V Boys Outdoor Track | FERMI CO-ED RELAYS | Away - FERMI HIGH SCHOOL | TBA | TBA (1 or 2 buses) | QUALIFIERS ONLY |
| Mon., 4/28 | V Baseball | Wilby | Away - Waterville park [Directions] | W 9-3 | 2:30 p.m. | |
| Mon., 4/28 | FR Baseball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Mon., 4/28 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | Woodland 198 42 55 43 58 Naugatuck 205 53 51 49 52 | 2:05 p.m. | |
| Mon., 4/28 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | W 5-4 | 2:30 p.m. | |
| Mon., 4/28 | V Softball | Wilby | Home - Woodland Softball Field [Directions] | W 15-0 | ||
| Mon., 4/28 | V Girls Tennis | Wilby | Home - Woodland High School Tennis courts [Directions] | W 7-0 | ||
| Tue., 4/29 | V Baseball | Derby | Away - Derby -Ryan Athletic Complex-baseball field [Directions] | L 3-4 | 2:30 p.m. | |
| Tue., 4/29 | V Boys Outdoor Track | Watertown, Wolcott | Away - John J. Mills Complex @ Watertown High School [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Tue., 4/29 | V Boys Tennis | Kennedy | Home - Woodland H.S. [Directions] | W 5-4 | 2:30 p.m. | |
| Tue., 4/29 | V Girls Outdoor Track | Watertown, Wolcott | Away - John J. Mills Complex @ Watertown High School [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Softball | Ansonia | Away - Ansonia High School [Directions] | W 8-0 | 2:30 | |
| Tue., 4/29 | JV Softball | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | 2:30 | |
| Tue., 4/29 | V Girls Tennis | Holy Cross | Away - HCHS [Directions] | W 5-1 | 2:50 p.m. | |
| Wed., 4/30 | JV Softball | Derby | Home - Woodland Softball Field [Directions] | Cancelled | ||
| Thu., 5/1 | V Boys Golf | Woodland Invitational | Home - Oxford Greens [Directions] | Cancelled | 1:30 p.m. | |
| Fri., 5/2 | V Baseball | St. Paul Catholic | Home - Woodland High School Baseball Field [Directions] | L 4-1 | ||
| Fri., 5/2 | V Boys Golf | Wolcott, Waterbury Coop | Away - Farmingbury Country Club [Directions] | Woodland 172 Wolcott 169 | 1:30 | |
| Fri., 5/2 | V Boys Tennis | Sacred Heart | Away - Fulton Park | L 3-6 | 2:30 p.m. | |
| Fri., 5/2 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 4-1 | 2:30 p.m. | |
| Fri., 5/2 | V Girls Tennis | St. Paul Catholic | Away - Peck Park, Bristol [Directions] | L 2-5 | 2:50 p.m. | |
| Sat., 5/3 | JV Baseball | St. Paul Catholic | Home - Woodland High School Baseball Field [Directions] | 2:30 p.m. | ||
| Sat., 5/3 | V Boys Outdoor Track | MIDDLETOWN INVITATIONAL | Away - MIDDLETOWN HIGH SCHOOL | TBA | tba (1 or 2 buses) | QUALIFIERS ONLY |
| Sat., 5/3 | V Softball | Derby | Home - Woodland Softball Field [Directions] | W 15-0 | ||
| Sat., 5/3 | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 9:00 a.m. | 7:45 a.m. | |
| Mon., 5/5 | V Baseball | Kennedy | Away - Waterville Park [Directions] | W 12-2 | 3:15 p.m. | |
| Mon., 5/5 | FR Baseball | Kennedy | Away - Bucks Hill Park [Directions] | 4:15 p.m. | 3:15 p.m. | |
| Mon., 5/5 | V Boys Golf | Crosby, Torrington | Home - Oxford Greens [Directions] | Woodland 179 Torrington 202 Crosby 259 | 2:05 p.m. | |
| Mon., 5/5 | V Softball | Kennedy | Home - Woodland Softball Field [Directions] | W 4-1 | ||
| Mon., 5/5 | JV Softball | Kennedy | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:15 p.m. | ||
| Mon., 5/5 | V Girls Tennis | Kennedy | Home - Woodland High School Tennis courts [Directions] | W 6-1 | ||
| Tue., 5/6 | JV Baseball | Kennedy | Away - Waterville Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 5/6 | V Boys Outdoor Track | Torrington, Crosby, Sacred Heart | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Tue., 5/6 | V Boys Tennis | Wilby | Home - Woodland High School Tennis courts [Directions] | W 7-2 | ||
| Tue., 5/6 | V Girls Outdoor Track | Torrington, Crosby, Sacred Heart | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Wed., 5/7 | V Baseball | Torrington | Home - Woodland High School Baseball Field [Directions] | L 11-5 | ||
| Wed., 5/7 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 5/7 | V Boys Golf | Stigberg | Away | Woodland 75 | ||
| Wed., 5/7 | V Boys Tennis | Torrington | Home - Woodland High School Tennis courts [Directions] | L 2-7 | ||
| Wed., 5/7 | V Softball | Torrington | Away - Torrington High School [Directions] | L 0-4 | 2:30 p.m. | |
| Wed., 5/7 | JV Softball | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:30 | |
| Wed., 5/7 | V Girls Tennis | Torrington | Away - Torrington High School [Directions] | W 6-1 | 2:50 p.m. | |
| Thu., 5/8 | V Boys Golf | Sacred Heart | Away - East Mountain | Woodland 179 Sacred Heart 184 | 2:05 p.m. | |
| Fri., 5/9 | V Baseball | Wolcott | Home - Woodland High School Baseball Field [Directions] | W 4-1 | ||
| Fri., 5/9 | V Boys Outdoor Track | LOUCKS GAMES | Away - WHITE PLAINS HIGH SCHOOL | TBA | QUALIFIERS ONLY - MAY ALSO BE 5/10 | |
| Fri., 5/9 | V Boys Tennis | Wolcott | Away - Wolcott High School [Directions] | L 0-7 | 2:30 p.m. | |
| Fri., 5/9 | V Softball | Wolcott | Away - George Babcock Field, Wolcott High School [Directions] | W 5-1 | 3:30 | |
| Fri., 5/9 | JV Softball | Wolcott | Away - Wolcott 2 [Directions] | 4:45 p.m. | 3:30 | |
| Fri., 5/9 | V Girls Tennis | Wolcott | Home - Woodland High School Tennis courts [Directions] | W 7-0 | ||
| Sat., 5/10 | JV Baseball | Wolcott | Home - Woodland High School Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/10 | FR Softball | Holy Cross | Home - Woodland Softball Field [Directions] | 11:00 a.m. | ||
| Mon., 5/12 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | W 3-1 | 4:30 p.m. | |
| Mon., 5/12 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Mon., 5/12 | V Boys Golf | Watertown | Away - Crestbrook Park Golf Course [Directions] | Woodland 193 Watertown 191 | 1:30 p.m. | |
| Mon., 5/12 | V Softball | Ansonia | Home - Woodland Softball Field [Directions] | W 3-0 | ||
| Mon., 5/12 | V Girls Tennis | St. Paul Catholic | Home - Woodland High School Tennis courts [Directions] | W 5-2 | ||
| Tue., 5/13 | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 5/13 | V Boys Golf | Holy Cross | Home - Western Hills [Directions] | Woodland 182 Watertown 174 Holy Cross 176 Wilby 269 | 2:05 p.m. | |
| Tue., 5/13 | V Boys Outdoor Track | St. Paul Catholic, Derby, Holy Cross | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Tue., 5/13 | V Boys Tennis | Lewis Mills | Away - Lewis Mills H.S. [Directions] | L 1-4 | 2:30 p.m. | |
| Tue., 5/13 | V Girls Outdoor Track | St. Paul Catholic, Derby, Holy Cross | Home - Woodland High School Track [Directions] | 3:30 p.m. | ||
| Tue., 5/13 | JV Softball | Ansonia | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | ||
| Tue., 5/13 | V Girls Tennis | Ansonia | Away - Woodland High School Tennis courts [Directions] | W 7-0 | will start after Ansonia/Wilby on WRHS courts | |
| Wed., 5/14 | V Baseball | Watertown | Home - Woodland High School Baseball Field [Directions] | W 9-0 | ||
| Wed., 5/14 | FR Baseball | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Wed., 5/14 | V Boys Tennis | Watertown | Home - Woodland High School Tennis courts [Directions] | L 4-5 | ||
| Wed., 5/14 | V Softball | Watertown | Away - Watertown High School [Directions] | W 5-4 | 2:30 p.m. | |
| Wed., 5/14 | JV Softball | Watertown | Away - Veteran's Park #1 [Directions] | 3:45 p.m. | 2:30 | |
| Wed., 5/14 | V Girls Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | W 6-1 | 2:50 p.m. | |
| Thu., 5/15 | JV Baseball | Watertown | Home - Woodland High School Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/15 | V Boys Golf | St. Paul Catholic | Home - Oxford Greens [Directions] | Woodland 189 St. Paul Catholic 181 | 2:05 p.m. | |
| Sat., 5/17 | V Girls Tennis | Seymour | Home - Woodland High School Tennis courts [Directions] | W 7-0 | ||
| Mon., 5/19 | V Baseball | Derby | Home - Woodland High School Baseball Field [Directions] | L 7-5 | ||
| Mon., 5/19 | V Boys Golf | Naugatuck | Away - Hop Brook [Directions] | Woodland 182 Naugatuck 175 | 2:05 p.m. | |
| Mon., 5/19 | V Boys Tennis | Holy Cross | Home - Woodland High School Tennis courts [Directions] | L 3-6 | ||
| Mon., 5/19 | V Softball | Derby | Away - Derby- Ryan Athletic Complex- softball field [Directions] | W 10-2 | 2:45 p.m. | |
| Tue., 5/20 | V Baseball | St. Paul Catholic | Away - Muzzy Field, Bristol [Directions] | L 3-2 | 2:30 p.m. | |
| Tue., 5/20 | FR Baseball | St. Paul Catholic | Away - Page Park, Bristol [Directions] | 3:30 p.m. | ||
| Tue., 5/20 | V Boys Outdoor Track | O'Brien Tech, Platt Tech | Home - Woodland High School Track [Directions] | 3:30 p.m. | Senior Night | |
| Tue., 5/20 | V Girls Outdoor Track | O'Brien Tech, Platt Tech | Home - Woodland High School Track [Directions] | 3:30 p.m. | Senior Night | |
| Tue., 5/20 | V Softball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | W 2-1 | ||
| Tue., 5/20 | JV Softball | St. Paul Catholic | Home - Woodland Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Baseball | Goodwin Tech | Away - Goodwin Tech HS Field [Directions] | W 13-3 | 2:30 p.m. | |
| Wed., 5/21 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Wed., 5/21 | V Boys Tennis | Torrington | Away - Torrington High School [Directions] | L 1-6 | 2:30 p.m. | |
| Wed., 5/21 | V Softball | Seymour | Home - Woodland Softball Field [Directions] | L 3-7 | ||
| Wed., 5/21 | JV Softball | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 5/22 | V Boys Golf | Chappa | Away | TBA | ||
| Fri., 5/23 | V Boys Golf | Waterbury Coop, Wolcott | Home - Oxford Greens [Directions] | Woodland 183 Wolcott 179 | 2:05 p.m. | |
| Sat., 5/24 | V Baseball | Seymour | Away - French Park [Directions] | L 0-6 | 1:45 p.m. | |
| Sat., 5/24 | V Softball | NVL Tournament Quarter-Finals | Home - Woodland Softball Field [Directions] | 1:00 p.m. | ||
| Sat., 5/24 | V Girls Tennis | Watertown | Home - Woodland High School Tennis courts [Directions] | 1:00 p.m. | ||
| Sat., 5/24 | V Girls Tennis | nvl semi-finals | Home - Woodland High School Tennis courts [Directions] | 4:00 p.m. | ||
| Tue., 5/27 | V Boys Golf | Torrington, Wilby | Away - Torrington Country Club [Directions] | Woodland 186 Torrington 182 | 1:30 p.m. | |
| Tue., 5/27 | V Boys Tennis | Kennedy | Away - Chase Park [Directions] | L 2-7 | ||
| Thu., 5/29 | V Baseball | Sacred Heart (Scrim.) | Home - Woodland High School Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 5/29 | V Boys Golf | Sacred Heart, Wilby | Home - Oxford Greens [Directions] | Woodland 185 Sacred Heart 205 Wilby | 2:05 p.m. | |
| Mon., 6/2 | V Boys Golf | East Hampton | Home - Oxford Greens [Directions] | Woodland 195 East Hampton 197 | 1:30 p.m. | |
| Thu., 6/5 | V Boys Golf | NVL Tournament | Away | TBA | TBA | |