| Woodland 2016-17 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 521 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | TBA | 2:20 | |
| TBA | JV Baseball | Crosby | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Wilby | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | ||
| TBA | JV Baseball | Derby | Home - Beacon Falls Rec - Pent Field [Directions] | TBA | ||
| TBA | FR Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | TBA | 2:30 | |
| TBA | FR Baseball | Naugatuck | Away - Rotary Field [Directions] | TBA | 2:30 | |
| TBA | FR Baseball | Wolcott | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | V Boys Golf | Crosby | Away - East Mountain [Directions] | 2:30 p.m. | ||
| TBA | JV Boys Soccer | Kennedy | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 8:00 a.m. | |
| TBA | JV Girls Soccer | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Softball | Torrington | Home - Woodland Softball Field [Directions] | 11:30 a.m. | ||
| TBA | JV Softball | Kennedy | Home - Woodland Softball Field [Directions] | 9:00 a.m. | ||
| TBA | JV Softball | Sacred Heart | Home - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Softball | Seymour | Away - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | Crosby | Away - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Naugatuck | Away - Naugatuck HS [Directions] | TBA | ||
| Tue., 11/17 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Thu., 9/1 | V Boys Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Thu., 9/1 | V Girls Soccer | Newtown (Scrim.) | Away - Treadwell Town Park--Tilson Field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 9/2 | V Football | O'Brien Tech (Scrim.) | Away - O'Brien Tech Athletic Complex [Directions] | 4:30 p.m. | 2:30 p.m. | |
| Sat., 9/3 | V Boys Cross Country | West Haven Beach Run | Away - West Haven Beach | TBA | 7:00 a.m. | |
| Sat., 9/3 | V Girls Cross Country | West Haven Beach Run | Away - West Haven Beach | TBA | 7:00 a.m. | |
| Sat., 9/3 | V Girls Soccer | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 11:00 a.m. | 9:45 A.M. | |
| Sat., 9/3 | V Girls Volleyball | East Haven Jamboree | Away - East Haven HS | 8:30 a.m. | 7:45 a.m. | |
| Tue., 9/6 | V Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 9/6 | JV Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:30 p.m. | 2:20 p.m. | |
| Thu., 9/8 | V Girls Volleyball | Masuk (Scrim.) | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 9/9 | V Football | Crosby | Home - Woodland Football Field [Directions] | L 29-41 | ||
| Fri., 9/9 | V Boys Soccer | Seymour | Away - Seymour HS [Directions] | W 2-1 | 5:00 p.m. | |
| Fri., 9/9 | V Girls Soccer | Seymour | Home - Woodland Soccer Field [Directions] | W 7-0 | ||
| Fri., 9/9 | V Girls Swimming and Diving | NVL Indicationals | Away - Kennedy HS | Cancelled | 2:30 warm up | |
| Fri., 9/9 | V Girls Volleyball | Torrington | Away - Torrington HS [Directions] | L 0-3 | 3:30 | |
| Fri., 9/9 | JV Girls Volleyball | Torrington | Away - Torrington HS [Directions] | L 0-2 | 3:30 | |
| Sat., 9/10 | JV Football | Crosby | Away - Crosby HS [Directions] | 11:00 a.m. | 8:30 a.m. | Froshmore game |
| Sat., 9/10 | JV Boys Soccer | Seymour | Away - Seymour HS [Directions] | 11:00 a.m. | 10:00 a.m. | |
| Sat., 9/10 | V Girls Volleyball | Blast at the Beach | Away - West Haven Beach | TBA | TBA | |
| Tue., 9/13 | V Boys Cross Country | Naugatuck, Kennedy, Seymour | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 9/13 | V Boys Soccer | Kennedy | Home - Woodland Soccer Field [Directions] | W 4-2 | ||
| Tue., 9/13 | V Girls Cross Country | Naugatuck, Kennedy, Seymour | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 9/13 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | W 3-1 | 2:30 p.m. | |
| Tue., 9/13 | V Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | W 3-2 | ||
| Tue., 9/13 | JV Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | L 1-2 | ||
| Wed., 9/14 | JV Girls Soccer | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 9/14 | V Girls Swimming and Diving | Jonathan Law | Home - Woodland Pool [Directions] | Win 96-81 | ||
| Thu., 9/15 | JV Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Fri., 9/16 | V Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | L 6-44 | 4:15 p.m. | |
| Fri., 9/16 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | L 0-1 | 4:45 p.m. | |
| Fri., 9/16 | V Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | W 5-0 | ||
| Fri., 9/16 | V Girls Swimming and Diving | Suffield | Home - Woodland Pool [Directions] | Win 99-82 | ||
| Fri., 9/16 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | W 3-0 | 4:15 | |
| Fri., 9/16 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | W 2-0 | 4:15 | |
| Sat., 9/17 | V Boys Cross Country | Wilton Invitational | Away - Wilton HS | TBA | 7:30 a.m. | |
| Sat., 9/17 | FR Football | Watertown | Home - Woodland Football Field [Directions] | 10:00 a.m. | Froshmore game | |
| Sun., 9/18 | V Girls Volleyball | Hike at Sleeping Giant | Away - Sleeping Giant | TBA | TBA | |
| Tue., 9/20 | V Boys Cross Country | WCA, St. Paul Catholic, Wilby | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:20 p.m. | |
| Tue., 9/20 | V Boys Soccer | Derby | Home - Woodland Soccer Field [Directions] | W 8-1 | ||
| Tue., 9/20 | V Girls Cross Country | St. Paul Catholic, Wilby, WCA | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:20 p.m. | |
| Tue., 9/20 | V Girls Soccer | Derby | Away - Derby -Witek Park [Directions] | W 9-0 | 2:30 p.m. | |
| Tue., 9/20 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | Win 93-90 | 4:30 p.m. | |
| Tue., 9/20 | V Girls Volleyball | Watertown | Home - Woodland HS Gym [Directions] | W 3-0 | ||
| Tue., 9/20 | JV Girls Volleyball | Watertown | Home - Woodland HS Gym [Directions] | W 2-0 | ||
| Wed., 9/21 | JV Boys Soccer | Derby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 9/21 | V Girls Volleyball | Wilby | Home - Woodland HS Gym [Directions] | W 3-0 | ||
| Wed., 9/21 | JV Girls Volleyball | Wilby | Home - Woodland HS Gym [Directions] | W 2-0 | ||
| Fri., 9/23 | V Football | Sacred Heart | Home - Woodland Football Field [Directions] | L 28-67 | ||
| Fri., 9/23 | V Boys Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | W 5-3 | ||
| Fri., 9/23 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 2-1 | 2:30 p.m. | |
| Fri., 9/23 | V Girls Swimming and Diving | Seymour | Home - Woodland Pool [Directions] | Loss 85-95 | ||
| Fri., 9/23 | V Girls Volleyball | Wolcott | Home - Woodland HS Gym [Directions] | W 3-0 | ||
| Fri., 9/23 | JV Girls Volleyball | Wolcott | Home - Woodland HS Gym [Directions] | W 3-0 | ||
| Sat., 9/24 | FM Football | Sacred Heart | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | JV Boys Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 11:00 a.m. | ||
| Tue., 9/27 | V Boys Cross Country | Torrington, Wolcott, Crosby | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 9/27 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | T 0-0 | 4:30 p.m. | |
| Tue., 9/27 | V Girls Cross Country | Torrington, Crosby, Wolcott | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Watertown | Home - Woodland Soccer Field [Directions] | L 0-1 | ||
| Tue., 9/27 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | Loss 83-94 | 5:30 p.m. | |
| Tue., 9/27 | V Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | W 3-0 | 2:30 | |
| Tue., 9/27 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | W 2-0 | 2:30 | |
| Wed., 9/28 | JV Boys Soccer | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 9/28 | JV Girls Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 9/29 | JV Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 9/29 | JV Girls Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 9/29 | V Girls Volleyball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | W 3-0 | ||
| Thu., 9/29 | JV Girls Volleyball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | W 2-0 | ||
| Fri., 9/30 | V Football | Naugatuck | Away - Naugatuck HS [Directions] | L 0-39 | 4:45 p.m. | |
| Fri., 9/30 | V Boys Soccer | Wilby | Away - Municipal Stadium [Directions] | W 7-4 | 2:30 p.m. | |
| Fri., 9/30 | V Girls Soccer | Jonathan Law | Home - Woodland Soccer Field [Directions] | W 4-0 | ||
| Fri., 9/30 | V Girls Swimming and Diving | Naugatuck | Home - Woodland Pool [Directions] | Win 93-85 | ||
| Fri., 9/30 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 3-1 | 3:30 | |
| Fri., 9/30 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 2-1 | 3:30 | |
| Sat., 10/1 | FR Football | Naugatuck | Home - Woodland Football Field [Directions] | 3:45 p.m. | Froshmore game | |
| Sat., 10/1 | V Boys Soccer | Bunnell | Away - Pender's Field [Directions] | W 1-0 | 1:15 p.m. | |
| Mon., 10/3 | JV Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:30 p.m. | ||
| Tue., 10/4 | V Boys Cross Country | Watertown, Oxford, Ansonia | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/4 | V Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | W 4-0 | 2:30 p.m. | |
| Tue., 10/4 | V Girls Cross Country | Ansonia, Oxford, Watertown | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Wolcott | Home - Woodland Soccer Field [Directions] | W 5-1 | ||
| Tue., 10/4 | V Girls Swimming and Diving | Holy Cross | Home - Woodland HS Pool [Directions] | Win 87-71 | ||
| Tue., 10/4 | V Girls Volleyball | Crosby | Home - Woodland HS Gym [Directions] | W 3-0 | ||
| Tue., 10/4 | JV Girls Volleyball | Crosby | Home - Woodland HS Gym [Directions] | W 2-0 | ||
| Wed., 10/5 | JV Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 5:15 p.m. | 2:30 p.m. | |
| Wed., 10/5 | JV Girls Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 10/6 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | W 5-0 | 4:00 p.m. | |
| Fri., 10/7 | V Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | L 6-48 | 4:00 p.m. | |
| Fri., 10/7 | V Boys Soccer | Torrington | Home - Woodland Soccer Field [Directions] | W 4-2 | ||
| Fri., 10/7 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | Win 91-64 | 2:30 p.m. | |
| Fri., 10/7 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | W 3-0 | 3:30 | |
| Fri., 10/7 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | W 2-1 | 3:30 | |
| Sat., 10/8 | FM Football | Oxford | Home - Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | JV Boys Soccer | Torrington | Home - Woodland HS Varsity Field [Directions] | 10:30 a.m. | ||
| Sun., 10/9 | V Girls Volleyball | Hall of Fame visit/overnight | Away - Massachussets | TBA | ||
| Mon., 10/10 | V Girls Volleyball | Spalding Volleyball Classic | Away - American International College, Springfield, MA | TBA | ||
| Tue., 10/11 | V Boys Cross Country | Holy Cross, Derby, Sacred Heart | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/11 | V Boys Soccer | Oxford | Home - Woodland Soccer Field [Directions] | W 3-1 | ||
| Tue., 10/11 | V Girls Cross Country | Holy Cross, Derby, Sacred Heart | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | W 5-1 | 4:30 p.m. | |
| Wed., 10/12 | JV Boys Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 10/12 | JV Girls Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 10/12 | V Girls Swimming and Diving | Torrington | Away - Torrington Y [Directions] | Win 88-71 | 6:00 p.m. | |
| Thu., 10/13 | V Girls Volleyball | Seymour | Home - Woodland HS Gym [Directions] | L 2-3 | ||
| Thu., 10/13 | JV Girls Volleyball | Seymour | Home - Woodland HS Gym [Directions] | L 1-2 | ||
| Fri., 10/14 | V Football | Wolcott | Home - Woodland Football Field [Directions] | L 14-46 | ||
| Fri., 10/14 | V Boys Soccer | Sacred Heart | Away - Waterville Park | T 1-1 | 2:30 p.m. | |
| Fri., 10/14 | V Girls Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | W 8-0 | ||
| Fri., 10/14 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland Pool [Directions] | Win 88-78 | ||
| Fri., 10/14 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | W 3-0 | 3:30 | |
| Fri., 10/14 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | W 2-1 | 3:30 | |
| Sat., 10/15 | JV Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | Cancelled | 7:30 a.m. | Froshmore game |
| Sat., 10/15 | JV Boys Soccer | Sacred Heart | Away - Waterville Park | 1:00 p.m. | 11:45 a.m. | |
| Sat., 10/15 | V Girls Soccer | Bethel | Away - DeSantis Field at Bethel HS [Directions] | T 0-0 | 9:15 a.m. | |
| Tue., 10/18 | V Boys Soccer | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | W 2-0 | 4:45 p.m. | |
| Tue., 10/18 | V Girls Soccer | Holy Cross | Home - Woodland Football Field [Directions] | W 2-0 | SENIOR NIGHT | |
| Tue., 10/18 | V Girls Swimming and Diving | Oxford | Away - OHS Pool [Directions] | Win 100-83 | 2:30 p.m. | |
| Tue., 10/18 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | W 3-1 | 3:30 | |
| Tue., 10/18 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | L 1-2 | 3:30 | |
| Wed., 10/19 | V Boys Cross Country | NVL Championships | Away - Veterans Field, Watertown | 3:30 p.m. | 2:20 p.m. | 3:30 varsity girls; 4pm varsity boys; 4:30 combined JV |
| Wed., 10/19 | JV Boys Soccer | Holy Cross | Away - Lower Murray Park [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 10/19 | V Girls Cross Country | NVL Championships | Away - Veteran's Park, Watertown | 3:30 p.m. | TBA | |
| Wed., 10/19 | JV Girls Soccer | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 10/20 | JV Girls Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Fri., 10/21 | V Boys Soccer | Ansonia | Home - Woodland Football Field [Directions] | T 1-1 | SENIOR NIGHT | |
| Fri., 10/21 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | W 7-0 | 2:30 p.m. | |
| Fri., 10/21 | V Girls Swimming and Diving | Kennedy | Home - Woodland Pool [Directions] | Win 97-70 | SENIOR NIGHT | |
| Fri., 10/21 | V Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | L 1-3 | ||
| Fri., 10/21 | JV Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | L 0-2 | ||
| Sat., 10/22 | JV Boys Soccer | Ansonia | Home - Woodland HS Varsity Field [Directions] | 10:30 a.m. | ||
| Sat., 10/22 | V Girls Volleyball | East Haven | Home - Woodland HS Gym [Directions] | W 3-2 | ||
| Sat., 10/22 | JV Girls Volleyball | East Haven | Home - Woodland HS Gym [Directions] | W 2-0 | ||
| Mon., 10/24 | V Boys Cross Country | Platt Tech Invite | Away - Eisenhower Park, Milford | 3:30 p.m. | 2:15 p.m. | |
| Mon., 10/24 | V Boys Soccer | WCA | Home - Woodland Soccer Field [Directions] | W 7-0 | ||
| Mon., 10/24 | V Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | W 3-1 | 4:00 p.m. | |
| Mon., 10/24 | V Girls Volleyball | Holy Cross | Home - Woodland HS Gym [Directions] | W 3-1 | ||
| Mon., 10/24 | JV Girls Volleyball | Holy Cross | Home - Woodland HS Gym [Directions] | W 2-0 | ||
| Tue., 10/25 | JV Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | 5:00 p.m. | |
| Wed., 10/26 | V Boys Soccer | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | W 8-0 | 5:15 p.m. | |
| Wed., 10/26 | V Girls Soccer | Torrington | Home - Woodland Soccer Field [Directions] | W 4-0 | ||
| Wed., 10/26 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | W 3-0 | 3:15 | |
| Wed., 10/26 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | W 2-0 | 3:15 | |
| Thu., 10/27 | JV Boys Soccer | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 10/27 | JV Girls Soccer | Derby | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Thu., 10/27 | V Girls Volleyball | Amity | Away - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | L 1-3 | 2:45 | |
| Thu., 10/27 | JV Girls Volleyball | Amity | Away - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 3:45 p.m. | 2:45 | |
| Fri., 10/28 | V Football | St. Paul Catholic | Home - Woodland Football Field [Directions] | L 19-28 | ||
| Fri., 10/28 | JV Boys Soccer | WCA | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class SS Championship | Away - Wickham Park - East Hartford [Directions] | 10:20 a.m. | ||
| Sat., 10/29 | FM Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 10:00 a.m. | 7:15 a.m. | |
| Sat., 10/29 | V Boys Soccer | Torrington | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class MM Championship | Away - Wickham Park - East Hartford [Directions] | 1:30 p.m. | ||
| Sat., 10/29 | V Girls Soccer | Seymour | Home - Woodland Soccer Field [Directions] | 12:00 p.m. | ||
| Sat., 10/29 | V Girls Volleyball | Holy Cross | Home - Woodland HS Gym [Directions] | W 3-0 | ||
| Tue., 11/1 | V Boys Soccer | NVL Tournament Semi-Finals | Away - Seymour HS | TBA | ||
| Tue., 11/1 | V Girls Soccer | NVL Semi-Finals | Away - Watertown HS | TBA | ||
| Tue., 11/1 | V Girls Swimming and Diving | NVL Swim Trials | Away - Kennedy HS | 4:00 p.m. | 1:15 p.m. | 2pm warm ups |
| Wed., 11/2 | V Girls Swimming and Diving | NVL Diving championships | Away - Woodland HS Pool | 6:00 p.m. | 4pm warm ups | |
| Thu., 11/3 | V Boys Soccer | NVL Championships | Away - Naugatuck HS | TBA | ||
| Thu., 11/3 | V Girls Soccer | NVL Championships | Away - Naugatuck HS | TBA | ||
| Fri., 11/4 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Torrington | Away - Torrington HS [Directions] | L 15-40 | 4:45 p.m. | |
| Fri., 11/4 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | NVL Championships | Away - Kennedy HS | 4:00 p.m. | ||
| Sat., 11/5 | FM Football | Torrington | Home - Woodland Football Field [Directions] | 11:00 a.m. | ||
| Sat., 11/5 | V Boys Soccer | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 1:00 p.m. | 12noon | |
| Mon., 11/7 | V Girls Volleyball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 5:00 p.m. | ||
| Tue., 11/8 | V Boys Soccer | Wolcott Tech | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Girls Volleyball | Tolland | Away - Tolland HS [Directions] | 6:00 p.m. | 3:30 p.m. | |
| Thu., 11/10 | FM Football | Kennedy | Home - Woodland Football Field [Directions] | 3:30 p.m. | ||
| Thu., 11/10 | V Boys Soccer | Plainville | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Thu., 11/10 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Fri., 11/11 | V Football | Kennedy | Away - Municipal Stadium [Directions] | W 40-20 | 4:45 p.m. | |
| Sat., 11/12 | V Boys Cross Country | New England Championship | Away - Ponaganset HS (RI) [Directions] | TBA | ||
| Sat., 11/12 | V Girls Cross Country | New England Championship | Away - Ponaganset HS (RI) [Directions] | TBA | ||
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 2:00 p.m. | ||
| Fri., 11/18 | FM Football | Seymour | Away - Seymour HS Turf Field [Directions] | 3:30 p.m. | 8:00 a.m. | |
| Fri., 11/18 | V Girls Swimming and Diving | CIAC Open Diving | Away - Bulkeley HS [Directions] | 5:30 p.m. | ||
| Sat., 11/19 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Wed., 11/23 | V Football | Seymour | Home - Woodland Football Field [Directions] | L 20-55 | ||
| Sat., 12/3 | V Girls Basketball | Griswold (Scrim.) | Away - GHS Gym [Directions] | 10:30 a.m. | 8:30 p.m. | |
| Sat., 12/10 | V Boys Basketball | Thomaston (Scrim.) | Away - Thomaston H.S. Gymnasium [Directions] | 10:00 a.m. | 8:30 a.m. | |
| Mon., 12/12 | V Boys Indoor Track | Practice @ Wesleyan | Away | TBA | 3:45 | qualifiers only |
| Mon., 12/12 | V Girls Indoor Track | Practice @ Wesleyan | Away - Wesleyan | TBA | 3:45 | |
| Tue., 12/13 | V Girls Basketball | Derby | Home - Woodland HS Gym [Directions] | W 61-43 | ||
| Tue., 12/13 | JV Girls Basketball | Derby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/14 | V Boys Basketball | Whitney Tech (Scrim.) | Home - Woodland HS Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/14 | V Wrestling | Foran | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:00 p.m. | ||
| Wed., 12/14 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | W 53-27 | 3:15 p.m. | |
| Wed., 12/14 | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | 3:15 | |
| Sat., 12/17 | V Boys Indoor Track | Reindeer Relays | Away - Wilton HS | TBA | 7:15 a.m. | qualifiers only |
| Sat., 12/17 | V Girls Indoor Track | Reindeer Relays | Away - Wilton HS | TBA | 7:15 | |
| Sun., 12/18 | V Wrestling | Shelton, Masuk | Away - Shelton HS [Directions] | 2:00 p.m. | 12:15 p.m. | |
| Tue., 12/20 | V Boys Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | L 32-52 | ||
| Tue., 12/20 | JV Boys Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | FR Boys Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Boys Swimming and Diving | Crosby/WCA | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 56-36 | 4:00 p.m. | |
| Tue., 12/20 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Wed., 12/21 | V Boys Indoor Track | GLastonbury Invitational | Away - Glastonbury HS | TBA | 3:00 p.m. | 2 buses |
| Wed., 12/21 | V Wrestling | Xavier | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:00 p.m. | ||
| Wed., 12/21 | V Girls Indoor Track | Glastonbury Invitational | Away - Glastonbury HS | TBA | 3:00 | tw buses |
| Thu., 12/22 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | L 54-69 | 4:15 p.m. | |
| Thu., 12/22 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Thu., 12/22 | FR Boys Basketball | Seymour | Away - Seymour HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 12/22 | V Boys Swimming and Diving | Northwestern | Home - Woodland HS Pool [Directions] | 4:30 p.m. | ||
| Tue., 12/27 | V Boys Basketball | Ansonia | Home - Woodland HS Gym [Directions] | L 44-65 | ||
| Tue., 12/27 | JV Boys Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/27 | FR Boys Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/27 | V Wrestling | Frank Chaves Invitational - Simsbury | Away - Simsbury HS | 10:00 a.m. | 8:00 a.m. | |
| Thu., 12/29 | V Boys Indoor Track | Hillhouse Winter Relays | Away - Hillhouse a.k.a. F.L.A.C | 10:00 a.m. | 7:45 a.m. | |
| Thu., 12/29 | V Girls Indoor Track | Hillhouse Winter Relays | Away - Hillhouse / FLAC | 10:00 a.m. | ||
| Fri., 12/30 | V Boys Indoor Track | Wintergreen Invitational | Away - SCSU | TBA | TBA | tentatively scheduled |
| Fri., 12/30 | V Girls Indoor Track | Wintergreen Invitational | Away - SCSU | TBA | tentatively scheduled | |
| Sat., 12/31 | V Wrestling | Southington Duals | Away - Southington HS | 9:00 a.m. | 7:00 a.m. | |
| Tue., 1/3 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | L 58-70 | 4:15 p.m. | |
| Tue., 1/3 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Tue., 1/3 | FR Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 1/3 | V Girls Basketball | Watertown | Home - Woodland HS Gym [Directions] | L 45-48 | ||
| Tue., 1/3 | JV Girls Basketball | Watertown | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/4 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | 6:00 p.m. | |
| Wed., 1/4 | V Wrestling | Daniel Hand | Away - Polson Gym/DHHS Campus [Directions] | 6:30 p.m. | 4:30 | |
| Fri., 1/6 | V Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | L 45-79 | ||
| Fri., 1/6 | JV Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Seymour | Away - Seymour HS [Directions] | 4:00 p.m. | 4:45 p.m. | |
| Fri., 1/6 | V Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | W 46-39 | 4:15 p.m. | |
| Fri., 1/6 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Sat., 1/7 | V Wrestling | Darien, Bethel | Away - Darien HS [Directions] | 9:00 a.m. | 6:30 a.m. | |
| Mon., 1/9 | V Girls Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | L 43-38 | ||
| Mon., 1/9 | JV Girls Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/10 | V Wrestling | New Haven Wrestling | Away - Wilbur Cross H. S. [Directions] | 7:00 p.m. | 5:30 | |
| Wed., 1/11 | V Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | L 22-75 | Yes | |
| Wed., 1/11 | JV Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Wed., 1/11 | V Girls Basketball | Wilby | Home - Woodland HS Gym [Directions] | W 67-22 | ||
| Wed., 1/11 | JV Girls Basketball | Wilby | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | 5:00 p.m. | |
| Fri., 1/13 | V Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | L 38-84 | ||
| Fri., 1/13 | JV Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Kennedy | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | L 56-47 | 4:00 p.m. | |
| Fri., 1/13 | JV Girls Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Sat., 1/14 | V Wrestling | Gilbert Duals | Away - The Gilbert School, Winsted | 9:00 a.m. | 7:00 a.m. | |
| Tue., 1/17 | JV Girls Basketball | Oxford | Home - Woodland HS Gym [Directions] | Cancelled | ||
| Wed., 1/18 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | L 43-62 | 3:00 p.m. | |
| Wed., 1/18 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 4:00 p.m. | 3:00 p.m. | |
| Wed., 1/18 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | 4:45 p.m. | |
| Wed., 1/18 | V Wrestling | Jonathan Law | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:00 p.m. | ||
| Wed., 1/18 | V Girls Basketball | East Lyme | Home - Woodland HS Gym [Directions] | L 46-50 | ||
| Wed., 1/18 | JV Girls Basketball | East Lyme | Home - Woodland HS Gym [Directions] | Cancelled | ||
| Fri., 1/20 | V Boys Basketball | WCA | Home - Woodland HS Gym [Directions] | L 54-76 | ||
| Fri., 1/20 | JV Boys Basketball | WCA | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | WCA | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 1/20 | V Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | W 55-47 | 4:15 p.m. | |
| Fri., 1/20 | JV Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Sat., 1/21 | V Wrestling | New Milford Tournament | Away - New Milford HS | 10:00 a.m. | 6:30 a.m. | |
| Sat., 1/21 | V Girls Basketball | Oxford | Home - Woodland HS Gym [Directions] | W 48-20 | ||
| Tue., 1/24 | V Wrestling | East Haven | Away - East Haven HS [Directions] | 7:00 p.m. | 5:15 | |
| Wed., 1/25 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | L 45-49 | 4:00 p.m. | |
| Wed., 1/25 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Wed., 1/25 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 3:45 p.m. | 2:20 p.m. | |
| Wed., 1/25 | V Girls Basketball | Wolcott | Home - Woodland HS Gym [Directions] | W 63-57 | ||
| Wed., 1/25 | JV Girls Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Thu., 1/26 | V Boys Indoor Track | Glastonbury Invite | Away - Glastonbury HS | TBA | 3:00 | |
| Thu., 1/26 | V Boys Swimming and Diving | Sacred Heart | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 33-74 | 4:30 p.m. | |
| Fri., 1/27 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:00 p.m. | 4:30 p.m. | |
| Fri., 1/27 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 1/27 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby H.S. [Directions] | 6:00 p.m. | 5:00 p.m. | |
| Fri., 1/27 | V Girls Basketball | Crosby | Home - Woodland HS Gym [Directions] | L 38-39 | ||
| Fri., 1/27 | JV Girls Basketball | Crosby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/28 | V Wrestling | Ridgefield Challenge Tournament | Away - Ridgefield HS | 10:00 a.m. | 6:30 a.m. | |
| Mon., 1/30 | V Boys Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | L 59-80 | ||
| Mon., 1/30 | JV Boys Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/30 | FR Boys Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Mon., 1/30 | V Boys Indoor Track | NVL Championships | Away - New Haven Athletic | 4:30 p.m. | 2:45 p.m. | |
| Mon., 1/30 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | L 44-53 | 4:15 p.m. | |
| Mon., 1/30 | JV Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Mon., 1/30 | V Girls Indoor Track | NVL Championships | Away - FLAC - New Haven | 4:30 p.m. | TBA | |
| Wed., 2/1 | V Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | W 65-54 | ||
| Wed., 2/1 | JV Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/1 | FR Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/1 | V Boys Swimming and Diving | Watertown | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Wrestling | Cheshire | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:00 p.m. | ||
| Wed., 2/1 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | L 39-62 | 4:15 p.m. | |
| Wed., 2/1 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | 4:15p.m. | |
| Fri., 2/3 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | L 43-54 | 4:15 p.m. | |
| Fri., 2/3 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Fri., 2/3 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 2/3 | V Girls Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | W 38-25 | ||
| Fri., 2/3 | JV Girls Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Sat., 2/4 | V Wrestling | Foran Duals | Away - Foran HS | 9:00 a.m. | 7:00 a.m. | |
| Wed., 2/8 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | 3:00 p.m. | |
| Wed., 2/8 | V Wrestling | Fairfield Prep | Away - Alumni Hall, Fairfield University [Directions] | 5:30 p.m. | 3:30 | |
| Wed., 2/8 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | L 45-48 | 4:15 p.m. | |
| Wed., 2/8 | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Thu., 2/9 | V Girls Indoor Track | CIAC Class M Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Fri., 2/10 | JV Wrestling | JV SCC Tournament | Away - Wilbur Cross | 4:30 p.m. | 3:30 p.m. | |
| Sat., 2/11 | V Boys Basketball | Torrington | Away - Torrington HS [Directions] | L 58-63 | 4:00 p.m. | |
| Sat., 2/11 | JV Boys Basketball | Torrington | Away - Torrington HS [Directions] | 5:30 p.m. | 4:00 p.m. | |
| Sat., 2/11 | FR Boys Basketball | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | 2:20 p.m. | |
| Sat., 2/11 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | ||
| Sat., 2/11 | V Wrestling | SCC Championships | Away - Wilbur Cross | 11:00 a.m. | 9:00 | |
| Mon., 2/13 | V Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | L 50-58 | ||
| Mon., 2/13 | V Girls Basketball | Torrington | Home - Woodland HS Gym [Directions] | L 36-41 | ||
| Mon., 2/13 | JV Girls Basketball | Torrington | Home - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | L 53-75 | ||
| Tue., 2/14 | JV Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/14 | FR Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/14 | V Boys Swimming and Diving | Oxford | Home - Woodland HS Pool [Directions] | 5:00 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Seymour | Away - Seymour HS [Directions] | L 37-58 | 3:15 p.m. | |
| Tue., 2/14 | JV Girls Basketball | Seymour | Away - Seymour HS [Directions] | 4:00 p.m. | 3:15 p.m. | |
| Thu., 2/16 | V Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | L 50-52 | 4:00 p.m. | |
| Thu., 2/16 | JV Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:00 p.m. | 4:00 p.m. | |
| Thu., 2/16 | V Girls Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | W 56-37 | ||
| Thu., 2/16 | JV Girls Basketball | Kaynor Tech | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Fri., 2/17 | JV Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/17 | FR Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/17 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:00 p.m. | 2:20 | |
| Sat., 2/18 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | 7:00 a.m. | |
| Sat., 2/18 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Tue., 2/21 | V Boys Basketball | HMTCA | Home - Woodland HS Gym [Directions] | W 46-42 | ||
| Tue., 2/21 | JV Boys Basketball | HMTCA | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/22 | V Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | W 68-54 | 4:15 p.m. | |
| Wed., 2/22 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 5:15 p.m. | 4:15 p.m. | |
| Wed., 2/22 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 2/24 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 2/25 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Tue., 2/28 | V Boys Swimming and Diving | NVL Swim Trials | Away - Kennedy HS | 4:00 p.m. | ||
| Wed., 3/1 | V Boys Swimming and Diving | NVL Diving Championships | Home - Woodland HS Pool [Directions] | 6:00 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | NVL Swim Championships | Away - Kennedy HS Pool | 6:00 p.m. | ||
| Fri., 3/3 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | Cancelled | ||
| Sat., 3/4 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/4 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | Cancelled | ||
| Sat., 3/4 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 3:30 p.m. | ||
| Wed., 3/15 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Sat., 3/25 | V Baseball | Stratford (Scrim.) | Away - Penders Field [Directions] | 1:00 p.m. | 11:30 a.m. | |
| Sat., 3/25 | V Baseball | East Hartford Jamboree | Away | TBA | ||
| Thu., 3/30 | V Softball | Trumbull (Scrim.) | Away - Varsity Softball Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 4/3 | V Boys Tennis | Wilby | Home - Woodland HS Tennis courts [Directions] | W 7-2 | ||
| Mon., 4/3 | V Softball | Ansonia | Away - Ansonia HS [Directions] | W 21-2 | 2:30 p.m. | |
| Mon., 4/3 | V Girls Tennis | Wilby | Away - Bucks Hill Park [Directions] | W 7-0 | 2:30 | |
| Tue., 4/4 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | W 1-0 | 2:15 p.m. | |
| Wed., 4/5 | V Boys Outdoor Track | Watertown, Crosby | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 4/5 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | L 2-7 | 2:30 | |
| Wed., 4/5 | V Girls Outdoor Track | Watertown, Crosby | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | ||
| Wed., 4/5 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS Tennis courts [Directions] | L 2-5 | ||
| Fri., 4/7 | V Boys Tennis | Wolcott | Home - Woodland HS Tennis courts [Directions] | L 1-8 | ||
| Fri., 4/7 | V Softball | Sacred Heart | Away - change from Woodland Softball Field to Municipal Stadium - Joan Joyce Field | W 16-3 | ||
| Fri., 4/7 | V Girls Tennis | Wolcott | Away - Wolcott HS [Directions] | W 5-2 | 2:30 | |
| Sat., 4/8 | V Baseball | Wilby | Home - Woodland HS Baseball Field [Directions] | W 7-3 | ||
| Sat., 4/8 | JV Baseball | Sacred Heart | Away - Fulton Park | 12:30 p.m. | 9:45 | |
| Sat., 4/8 | V Boys Outdoor Track | Bellringer Invite | Away - East Hampton HS | 9:30 a.m. | 7:30 a.m. | |
| Sat., 4/8 | V Softball | Joel Barlow | Home - Woodland Softball Field [Directions] | L 0-29 | ||
| Mon., 4/10 | V Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | L 6-3 | ||
| Mon., 4/10 | FR Baseball | St. Paul Catholic | Home - Hotchkiss Field (Prospect) [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Sacred Heart | Away - Fulton Park | W 6-3 | 2:30 | |
| Mon., 4/10 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 0-15 | 2:30 p.m. | |
| Mon., 4/10 | V Girls Tennis | Sacred Heart | Home - Woodland HS Tennis courts [Directions] | W 5-2 | ||
| Tue., 4/11 | JV Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | V Boys Golf | Crosby | Home - Oxford Greens [Directions] | Woodland 188, Crosby 240 | ||
| Tue., 4/11 | V Boys Outdoor Track | Torrington, Oxford | Away - Torrington HS [Directions] | 10:00 a.m. | 8:00 a.m. | |
| Tue., 4/11 | V Girls Outdoor Track | Torrington, Oxford | Away - Torrington HS [Directions] | 10:00 a.m. | ||
| Wed., 4/12 | V Baseball | Watertown | Home - Woodland HS Baseball Field [Directions] | W 7-5 | ||
| Wed., 4/12 | JV Baseball | Watertown | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 4/12 | V Softball | Watertown | Home - Woodland Softball Field [Directions] | L 3-6 | ||
| Thu., 4/13 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | W 7-3 | 2:15 p.m. | |
| Thu., 4/13 | FR Baseball | Wolcott | Away - BAW [Directions] | 3:45 p.m. | 2:30 | |
| Thu., 4/13 | V Boys Tennis | Watertown | Home - Woodland HS Tennis courts [Directions] | L 4-5 | ||
| Thu., 4/13 | V Softball | Wolcott | Home - Woodland Softball Field [Directions] | L 1-13 | ||
| Thu., 4/13 | JV Softball | Wolcott | Home - Woodland HS Varsity Field [Directions] | 2:00 p.m. | ||
| Thu., 4/13 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | W 7-0 | 12:00 noon | |
| Sat., 4/15 | JV Baseball | Wolcott | Away - Wolcott HS [Directions] | 11:00 a.m. | 9:15 | |
| Sat., 4/15 | JV Softball | Watertown | Home - Woodland Softball Field [Directions] | 11:00 a.m. | ||
| Mon., 4/17 | V Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | W 13-2 | ||
| Mon., 4/17 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Mon., 4/17 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | Woodland 206, Sacred Heart 208 | ||
| Mon., 4/17 | V Boys Tennis | Kennedy | Home - Woodland HS Tennis courts [Directions] | W 9-0 | ||
| Mon., 4/17 | V Softball | Torrington | Away - Torrington HS [Directions] | L 0-12 | 2:30 p.m. | |
| Mon., 4/17 | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | W 7-0 | 2:30 | |
| Tue., 4/18 | V Baseball | Sacred Heart | Away - Fulton Park | L 3-7 | 2:15 p.m. | |
| Tue., 4/18 | JV Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/18 | V Boys Outdoor Track | Holy Cross, Naugatuck | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 4/18 | V Girls Outdoor Track | Holy Cross, Naugatuck | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Wed., 4/19 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | L 3-2 (9) | 2:15 p.m. | |
| Wed., 4/19 | V Softball | Oxford | Home - Woodland Softball Field [Directions] | L 6-18 | ||
| Wed., 4/19 | V Girls Tennis | Torrington | Home - Woodland HS Tennis courts [Directions] | W 6-1 | ||
| Thu., 4/20 | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | 3:45 p.m. | 2:30 | |
| Thu., 4/20 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | Woodland 208, Holy Cross 185 Woodland- 208 Alec Feducia-47 Josh Hassan-57 Julian Perino-50 Chris Guerrette- 54 Holy Cross- 185 Vin Grasiano-45 Mike Mencio-47 Greg Picard-46 Chris Ford-47 | ||
| Thu., 4/20 | V Boys Tennis | Torrington | Away - Torrington HS [Directions] | L 0-9 | 2:30 | |
| Thu., 4/20 | JV Softball | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Mon., 4/24 | V Baseball | Crosby | Home - Woodland HS Baseball Field [Directions] | W 21-5 | ||
| Mon., 4/24 | V Boys Golf | Watertown | Away [Directions] | Woodland 203 Watertown 197 | ||
| Mon., 4/24 | V Softball | Crosby | Away - Crosby HS Field #1 [Directions] | W 24-2 | 2:30 p.m. | |
| Wed., 4/26 | V Boys Outdoor Track | Derby, WCA | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Wed., 4/26 | V Boys Tennis | Wolcott | Away - Wolcott HS [Directions] | L 0-9 | 2:30 | |
| Wed., 4/26 | V Girls Outdoor Track | Derby, WCA | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Wed., 4/26 | V Girls Tennis | Seymour | Home - Woodland HS Tennis courts [Directions] | W 5-2 | ||
| Thu., 4/27 | V Baseball | WCA | Home - Woodland HS Baseball Field [Directions] | W 7-0 | ||
| Thu., 4/27 | JV Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:20 | |
| Thu., 4/27 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | Woodland 197, Naugatuck 230 | ||
| Thu., 4/27 | V Boys Tennis | Crosby | Away - Crosby HS [Directions] | W 7-0 | 2:30 | |
| Thu., 4/27 | V Boys Tennis | Crosby | Home - Crosby HS [Directions] | W 6-1 | ||
| Thu., 4/27 | V Softball | Seymour | Away - Seymour HS [Directions] | L 4-17 | 2:30 p.m. | |
| Thu., 4/27 | V Girls Tennis | Crosby | Home - Woodland HS Tennis courts [Directions] | W 7-0 | ||
| Fri., 4/28 | JV Baseball | WCA | Home - Pent Field, Beacon Falls [Directions] | 3:30 p.m. | ||
| Fri., 4/28 | V Boys Golf | Wolcott | Away - Farmingbury Country Club [Directions] | Woodland 182, Wolcott 174 | ||
| Fri., 4/28 | V Boys Tennis | Holy Cross | Away - Holy Cross HS [Directions] | L 3-6 | 2:30 | |
| Fri., 4/28 | V Softball | Shelton | Away - Shelton HS Softball Field [Directions] | L 3-15 | ||
| Fri., 4/28 | V Girls Tennis | Holy Cross | Home - Woodland HS Tennis courts [Directions] | W 5-2 | ||
| Sat., 4/29 | V Baseball | Seymour | Away - French Park [Directions] | L 3-2 | 2:15 p.m. | |
| Sat., 4/29 | FR Baseball | Seymour | Away - French Park [Directions] | 5:15 p.m. | 2:30 | |
| Sun., 4/30 | V Baseball | Naugatuck | Away - Naugatuck HS [Directions] | W 7-3 | 2:15 p.m. | |
| Mon., 5/1 | V Boys Golf | Wilby, Seymour | Home - Oxford Greens [Directions] | Woodland 190, Seymour 201 | ||
| Mon., 5/1 | V Softball | Wilby | Home - Woodland Softball Field [Directions] | W 24-1 | ||
| Mon., 5/1 | JV Softball | Wilby | Home - Woodland Softball Field [Directions] | 5:00 p.m. | ||
| Tue., 5/2 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | Woodland 203 Torrington 175 | ||
| Tue., 5/2 | V Boys Outdoor Track | St. Paul Catholic, Wilby | Home - Woodland HS Track [Directions] | 3:30 p.m. | Kayor also included | |
| Tue., 5/2 | V Boys Tennis | Naugatuck | Home - Woodland HS Tennis courts [Directions] | L 4-5 | ||
| Tue., 5/2 | V Girls Outdoor Track | St. Paul Catholic, Wilby | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/2 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | L 1-8 | 2:30 p.m. | |
| Tue., 5/2 | V Girls Tennis | Naugatuck | Away - Naugatuck HS [Directions] | L 2-5 | 2:30 | |
| Wed., 5/3 | V Baseball | Kennedy | Away - Waterville Park [Directions] | W 17-3 | 2:15 p.m. | |
| Wed., 5/3 | V Boys Tennis | Torrington | Home - Woodland HS Tennis courts [Directions] | L 0-9 | ||
| Wed., 5/3 | V Softball | Kennedy | Home - Woodland Softball Field [Directions] | W 16-1 | ||
| Thu., 5/4 | V Boys Golf | Woodland Invitational | Home - Oxford Greens [Directions] | Woodland 378 | ||
| Thu., 5/4 | V Girls Tennis | St. Paul Catholic | Away - Peck Park, Bristol [Directions] | L 4-3 | 2:30 | |
| Sat., 5/6 | V Softball | Wolcott | Away - Tyrell MS [Directions] | L 0-5 | 2:30 p.m. | |
| Mon., 5/8 | V Baseball | Watertown | Away - Deland Field [Directions] | L 4-3 | 2:15 p.m. | |
| Mon., 5/8 | FR Baseball | Kennedy | Away - Bucks Hill Park [Directions] | 3:30 p.m. | 2:30 | subvarsity |
| Mon., 5/8 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | Woodland 173 | ||
| Mon., 5/8 | V Boys Tennis | Kennedy | Away - Kennedy HS [Directions] | W 9-0 | 2:30 | |
| Mon., 5/8 | V Softball | Watertown | Away - Watertown HS [Directions] | L 8-11 | 2:30 p.m. | |
| Mon., 5/8 | V Girls Tennis | Ansonia | Home - Woodland HS Tennis courts [Directions] | W 7-0 | ||
| Tue., 5/9 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | 2:20 | |
| Tue., 5/9 | V Boys Outdoor Track | Seymour, Wolcott | Away - Seymour HS [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Tue., 5/9 | V Girls Outdoor Track | Seymour, Wolcott | Away - Seymour HS [Directions] | 3:30 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Seymour | Away - Seymour HS [Directions] | W 5-2 | 2:30 | |
| Wed., 5/10 | V Baseball | Naugatuck | Home - Woodland HS Baseball Field [Directions] | L 1-0 | ||
| Wed., 5/10 | FR Baseball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 5/10 | V Boys Golf | Stigberg | Away | TBA | ||
| Wed., 5/10 | V Boys Tennis | Watertown | Away - Crestbrook Park [Directions] | W 7-2 | 2:30 | |
| Wed., 5/10 | V Softball | Naugatuck | Home - Woodland Softball Field [Directions] | L 2-8 | ||
| Wed., 5/10 | V Girls Tennis | Watertown | Home - Woodland HS Tennis courts [Directions] | L 2-5 | ||
| Thu., 5/11 | V Baseball | Derby | Home - Woodland HS Baseball Field [Directions] | W 5-2 | ||
| Thu., 5/11 | V Softball | Derby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | W 16-6 | ||
| Fri., 5/12 | JV Baseball | Naugatuck | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Fri., 5/12 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | Woodland 193, Sacred Heart 180 | ||
| Fri., 5/12 | JV Softball | Naugatuck | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | W 13-0 | 2:15 p.m. | |
| Mon., 5/15 | FR Baseball | Torrington | Home - Beacon Falls Rec - Pent Field [Directions] | 3:45 p.m. | 2:30 | |
| Mon., 5/15 | V Boys Golf | Holy Cross | Away - Western Hills [Directions] | Woodland 206 Holy Cross 179 | ||
| Mon., 5/15 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | L 2-7 | 2:30 | |
| Mon., 5/15 | V Softball | Torrington | Home - Woodland Softball Field [Directions] | L 0-13 | ||
| Mon., 5/15 | V Girls Tennis | NVL Quarter-final Team tournament vs Sacred Heart | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | possible move to 5/16/17 - higher seed | |
| Tue., 5/16 | V Baseball | Goodwin Tech | Home - Woodland HS Baseball Field [Directions] | W 4-1 | ||
| Tue., 5/16 | JV Baseball | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | 2:20 | |
| Tue., 5/16 | V Boys Golf | Waterbury Coop, Wilby | Away - Western Hills [Directions] | Woodland 188, Wilby 240 | ||
| Tue., 5/16 | V Boys Outdoor Track | Kennedy, Sacred Heart | Home - Woodland HS Track [Directions] | 3:30 p.m. | O'Brien and Platt Tech incl | |
| Tue., 5/16 | V Girls Outdoor Track | Kennedy, Sacred Heart | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Softball | Holy Cross | Away - Holy Cross HS [Directions] | L 0-8 | 2:30 p.m. | |
| Wed., 5/17 | V Baseball | East Granby | Away - East Granby HS [Directions] | W 13-11 | ||
| Wed., 5/17 | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 5/17 | V Girls Tennis | NVL Team Semi-Finals | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | Possible move to 5/18 - higher seed | |
| Thu., 5/18 | V Baseball | Wolcott | Home - Woodland HS Baseball Field [Directions] | W 4-2 | ||
| Thu., 5/18 | JV Baseball | Seymour | Away - French Park [Directions] | 3:30 p.m. | 2:30 | |
| Thu., 5/18 | V Boys Golf | St. Paul Catholic | Home - Oxford Greens [Directions] | Woodland 199 St. Paul 190 | ||
| Fri., 5/19 | JV Baseball | Wolcott | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/19 | V Girls Tennis | NVL Team Championshps | Home - Woodland HS Tennis courts [Directions] | 3:00 p.m. | ||
| Sat., 5/20 | V Baseball | NVL Quarter-finals vs St. Paul | Away - St. Paul HS | 1:00 p.m. | 11:30 p.m. | |
| Sat., 5/20 | V Baseball | NVL Tournament - Quarterfinals | Home - TBA - higher seed [Directions] | TBA | ||
| Sat., 5/20 | JV Softball | Wolcott | Away - Wolcott HS [Directions] | 9:00 a.m. | ||
| Sat., 5/20 | JV Softball | Watertown | Away - Wolcott HS [Directions] | 11:00 p.m. | ||
| Mon., 5/22 | V Baseball | NVL Tournament - semi finals | Away - Municipal Stadium | TBA | TBA | |
| Mon., 5/22 | V Boys Golf | Kaynor Tech | Home - Oxford Greens [Directions] | Woodland 166 Kaynor Tech. 201 | ||
| Mon., 5/22 | V Girls Tennis | NVL Individual Opening Rounds | Home - Woodland HS Tennis courts [Directions] | 12:00 p.m. | ||
| Tue., 5/23 | V Boys Outdoor Track | NVL Championships | Away - Seymour HS | TBA | ||
| Wed., 5/24 | V Baseball | NVL Tournament Championships | Away - Municipal Stadium | TBA | ||
| Wed., 5/24 | V Boys Outdoor Track | JV NVL Championships | Away - TBA | TBA | ||
| Wed., 5/24 | V Girls Tennis | NVL Individual Championships | Home - Woodland HS Tennis courts [Directions] | 12:00 p.m. | ||
| Sat., 5/27 | V Girls Tennis | Rocky Hill | Home [Directions] | 10:00 a.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Thu., 6/1 | V Boys Golf | NVL Championships | Away | TBA | ||
| Mon., 6/5 | V Boys Golf | CIAC Div. III Championship | Away - Timberlin GC - Kensington [Directions] | 8:00 a.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Sat., 6/10 | V Boys Outdoor Track | New England Championship | Away - Norwell (MA) HS [Directions] | TBA | ||
| Sat., 6/10 | V Girls Outdoor Track | New England Championship | Away - Norwell (MA) HS [Directions] | TBA | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Wed., 6/21 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||