| Woodland 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 553 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Naugatuck | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| TBA | JV Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | ||
| TBA | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Holy Cross | Away - Holy Cross HS [Directions] | TBA | ||
| TBA | JV Baseball | Seymour | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | FR Baseball | Kennedy | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| TBA | JV Boys Basketball | Wilby | Away - Wilby gym [Directions] | TBA | ||
| TBA | JV Boys Soccer | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| TBA | JV Girls Basketball | Wilby | Home - Woodland HS Gym [Directions] | TBA | ||
| TBA | JV Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:30 p.m. | ||
| TBA | JV Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | ||
| TBA | JV Softball | Masuk | Home - Pent Field Beacon Falls [Directions] | 3:30 p.m. | ||
| TBA | JV Softball | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| TBA | JV Softball | Watertown | Away - Veteran's Park #1 [Directions] | 3:30 p.m. | ||
| TBA | JV Softball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | Cancelled | |
| TBA | JV Softball | Crosby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | TBA | ||
| Sat., 8/29 | V Football | Hopkins School (Scrim.) | Away - Hopkins School Football field | 8:30 a.m. | ||
| Sat., 8/29 | V Football | Hopkins School (Scrim.) | Away - Hopkins School Football field | 8:30 a.m. | ||
| Mon., 8/31 | V Boys Soccer | Cheshire (Scrim.) | Away - Cheshire HS soccer field [Directions] | 4:00 p.m. | ||
| Mon., 8/31 | V Girls Volleyball | St. Joseph (Scrim.) | Away - St. Joseph HS [Directions] | 4:00 p.m. | 3 varsity and 2 jv games | |
| Thu., 9/3 | V Football | Old Saybrook (Scrim.) | Home - Woodland Football Field [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | V Football | Old Saybrook (Scrim.) | Home - Woodland Football Field [Directions] | 4:30 p.m. | ||
| Fri., 9/4 | V Girls Soccer | Pomperaug (Scrim.) | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 9/4 | V Girls Swimming and Diving | NVL Indicationals | Away - Kennedy HS | 4:00 p.m. | 2:30 warm ups | |
| Sat., 9/5 | V Boys Cross Country | West Haven Beach Run | Away - West Haven Beach | TBA | ||
| Sat., 9/5 | V Girls Volleyball | East Haven Play-around | Away | TBA | ||
| Tue., 9/8 | V Girls Volleyball | Bethel (Scrim.) | Away - Bethel HS [Directions] | 3:30 p.m. | ||
| Wed., 9/9 | V Girls Volleyball | Shelton (Scrim.) | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/9 | JV Girls Volleyball | Shelton (Scrim.) | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/11 | V Football | Oxford | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 27-7 | |
| Fri., 9/11 | JV Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:30 p.m. | ||
| Fri., 9/11 | JV Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 9/11 | V Girls Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | Win - 100-77 | |
| Fri., 9/11 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 9/11 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 4:45 p.m. | L 1-2 | |
| Sat., 9/12 | JV Football | Oxford | Away [Directions] | 10:00 a.m. | froshmore game | |
| Sat., 9/12 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | L 0-3 | |
| Sat., 9/12 | V Girls Soccer | Naugatuck | Home - Woodland Soccer Field [Directions] | 3:00 p.m. | W 2-1 | |
| Tue., 9/15 | V Boys Cross Country | Wilby, St. Paul Catholic, WCA | Home - Woodland HS Track [Directions] | 3:45 p.m. | Abbot and Wolcott Tech | |
| Tue., 9/15 | V Boys Soccer | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | W 3-1(OT) | |
| Tue., 9/15 | V Girls Cross Country | Wilby, St. Paul Catholic, WCA | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 9/15 | V Girls Soccer | Holy Cross | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 4-2 | |
| Tue., 9/15 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | Loss 85-95 | |
| Tue., 9/15 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/15 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 9/16 | JV Boys Soccer | Holy Cross | Away - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 9/16 | JV Girls Soccer | Holy Cross | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 9/18 | V Football | Torrington | Home - Woodland Football Field [Directions] | 6:30 p.m. | L 13-44 | |
| Fri., 9/18 | V Boys Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | L 1-2 | |
| Fri., 9/18 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 9/18 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:15 p.m. | W 3-0 | |
| Fri., 9/18 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 9/19 | V Boys Cross Country | Wilton Invitational | Away - Wilton HS | TBA | ||
| Sat., 9/19 | JV Football | Torrington | Away - Torrington HS [Directions] | 10:00 a.m. | Froshmore Game | |
| Sat., 9/19 | JV Boys Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/19 | JV Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 10:30 a.m. | ||
| Mon., 9/21 | V Girls Soccer | Branford | Away - Branford HS-Turf Field [Directions] | 6:30 p.m. | W 4-1 | |
| Tue., 9/22 | V Boys Cross Country | Crosby, Torrington, Wolcott | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 9/22 | V Girls Cross Country | Crosby, Torrington, Wolcott | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 9/22 | JV Girls Soccer | Branford | Away - 'Flax Mill Field [Directions] | 3:45 p.m. | ||
| Tue., 9/22 | V Girls Swimming and Diving | Oxford | Home - Woodland HS Pool [Directions] | 4:00 p.m. | Win 101-85 | |
| Tue., 9/22 | V Girls Volleyball | Wolcott | Home - Woodland HS Gym [Directions] | 6:15 p.m. | W 3-0 | |
| Tue., 9/22 | JV Girls Volleyball | Wolcott | Home - Woodland HS Gym [Directions] | 5:00 p.m. | W 2-0 | |
| Wed., 9/23 | V Boys Soccer | Sacred Heart | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 5-1 | |
| Wed., 9/23 | V Girls Soccer | Sacred Heart | Away - Bucks Hill Park | 3:45 p.m. | W 9-0 | |
| Thu., 9/24 | JV Boys Soccer | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 9/24 | V Girls Volleyball | Watertown | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/24 | JV Girls Volleyball | Watertown | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 9/25 | V Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:30 p.m. | L 15-55 | |
| Fri., 9/25 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 6:00 p.m. | Loss 80-100 | |
| Fri., 9/25 | V Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 9/25 | JV Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 9/26 | JV Football | Wolcott | Home - Woodland Football Field [Directions] | 10:00 a.m. | Froshmore Game | |
| Sat., 9/26 | V Boys Soccer | Bunnell | Home - Woodland Soccer Field [Directions] | 11:00 a.m. | L 0-1 | |
| Mon., 9/28 | JV Boys Soccer | Bunnell | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Mon., 9/28 | V Girls Soccer | Jonathan Law | Away - Jonathan Law HS Stadium [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 9/29 | V Boys Cross Country | Ansonia, Oxford, Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Tue., 9/29 | V Girls Cross Country | Ansonia, Oxford, Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Wed., 9/30 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | 6:30 p.m. | W 4-0 | |
| Wed., 9/30 | V Girls Swimming and Diving | Naugatuck | Home - Woodland HS Pool [Directions] | 4:00 p.m. | Win 95-88 | |
| Thu., 10/1 | V Boys Soccer | Torrington | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 4-1 | |
| Thu., 10/1 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Thu., 10/1 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 10/2 | V Football | Watertown | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 40-7 | |
| Fri., 10/2 | V Boys Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 3:30 p.m. | W 2-1 | |
| Fri., 10/2 | V Girls Soccer | Oxford | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 7-1 | |
| Fri., 10/2 | V Girls Swimming and Diving | Suffield | Home - Woodland HS Pool [Directions] | 5:00 p.m. | Tie 90-90 | |
| Fri., 10/2 | V Girls Volleyball | Holy Cross | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/2 | JV Girls Volleyball | Holy Cross | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/3 | JV Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | Froshmore Game | |
| Sat., 10/3 | JV Boys Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | 10:30 a.m. | ||
| Sat., 10/3 | JV Girls Soccer | Oxford | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 10/5 | V Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/5 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | 4:00 p.m. | Win 85-74 | |
| Tue., 10/6 | V Boys Cross Country | Holy Cross, Sacred Heart, Derby | Away - Holy Cross HS [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Holy Cross, Sacred Heart, Derby | Away - Holy Cross HS [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Girls Volleyball | Wilby | Home - Woodland HS Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 10/6 | JV Girls Volleyball | Wilby | Home - Woodland HS Gym [Directions] | 3:30 p.m. | W 2-0 | |
| Wed., 10/7 | V Boys Soccer | Wilby | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 4-0 | |
| Wed., 10/7 | V Girls Swimming and Diving | Seymour | Home - Woodland HS Pool [Directions] | 3:30 p.m. | Loss 82-93 | |
| Thu., 10/8 | JV Boys Soccer | Wilby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Thu., 10/8 | V Girls Volleyball | Kennedy | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 10/8 | JV Girls Volleyball | Kennedy | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 10/9 | V Football | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | 6:30 p.m. | W 30-7 | |
| Fri., 10/9 | V Boys Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/9 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 10/10 | JV Football | Holy Cross | Home - Woodland Football Field [Directions] | 10:00 a.m. | Froshmore Game | |
| Sat., 10/10 | JV Boys Soccer | St. Paul Catholic | Home - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Sat., 10/10 | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 11:00 a.m. | ||
| Tue., 10/13 | V Boys Cross Country | Naugatuck, Kennedy, Seymour | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/13 | V Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 10/13 | V Girls Cross Country | Naugatuck, Kennedy, Seymour | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Wolcott | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 10/13 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland HS Pool [Directions] | 4:00 p.m. | Win 92-82 | |
| Tue., 10/13 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/13 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/14 | JV Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 3:45 p.m. | ||
| Wed., 10/14 | JV Girls Soccer | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | V Boys Soccer | Oxford | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | L 0-3 | Out of League Game |
| Thu., 10/15 | V Girls Swimming and Diving | Jonathan Law | Away - Foran HS Pool [Directions] | 4:00 p.m. | Win 93-87 | |
| Thu., 10/15 | V Girls Volleyball | Crosby | Away - Wilby HS [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/15 | JV Girls Volleyball | Crosby | Away - Wilby HS [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 10/16 | V Boys Soccer | Crosby | Away - Crosby HS [Directions] | 3:45 p.m. | L 1-4 | |
| Fri., 10/16 | V Girls Soccer | Torrington | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 10/16 | V Girls Swimming and Diving | Masuk | Home - Woodland HS Pool [Directions] | 4:00 p.m. | loss 82-100 | |
| Fri., 10/16 | V Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/16 | JV Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/17 | JV Boys Soccer | Crosby | Away - Crosby HS [Directions] | 11:00 a.m. | ||
| Mon., 10/19 | V Girls Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | WIn 89-81 | |
| Tue., 10/20 | V Boys Soccer | Ansonia | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | W 1-0 | |
| Tue., 10/20 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | W 4-0 | |
| Tue., 10/20 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/20 | JV Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 4:45 p.m. | L 1-2 | |
| Wed., 10/21 | V Boys Cross Country | NVL Championships | Away - Veterans Park | 3:45 p.m. | ||
| Wed., 10/21 | JV Boys Soccer | Ansonia | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 10/21 | V Girls Cross Country | NVL Championships | Away - Veterans Park | 3:45 p.m. | ||
| Wed., 10/21 | V Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 10/21 | JV Girls Volleyball | Naugatuck | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Thu., 10/22 | FR Football | Sacred Heart | Home - Woodland Football Field [Directions] | Cancelled | Cancelled | |
| Thu., 10/22 | V Girls Soccer | Watertown | Home - Woodland Soccer Field [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 10/23 | JV Football | Sacred Heart | Home - Woodland Football Field [Directions] | 6:00 p.m. | ||
| Fri., 10/23 | V Boys Soccer | Kennedy | Away - West Side MS [Directions] | 3:30 p.m. | T 1-1 | |
| Fri., 10/23 | JV Girls Soccer | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 10/23 | V Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/23 | JV Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-1 | |
| Sat., 10/24 | V Football | Sacred Heart | Away - Municipal Stadium | 10:30 a.m. | W 42-7 | |
| Sat., 10/24 | JV Boys Soccer | Kennedy | Away - West Side MS [Directions] | 10:00 a.m. | ||
| Mon., 10/26 | V Boys Cross Country | Platt Tech | Away - Eisenhower Park, Milford [Directions] | Cancelled | Cancelled | |
| Mon., 10/26 | V Boys Soccer | Derby | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 6:00 p.m. | W 2-1 | |
| Mon., 10/26 | V Girls Soccer | Derby | Home - Woodland Football Field [Directions] | 6:00 p.m. | W 9-1 | Senior night |
| Mon., 10/26 | V Girls Volleyball | Masuk | Home - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/26 | JV Girls Volleyball | Masuk | Home - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Tue., 10/27 | V Boys Soccer | Seymour | Home - Woodland Football Field [Directions] | 6:00 p.m. | L 0-1 | Senior night |
| Tue., 10/27 | JV Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | Cancelled | Cancelled | |
| Tue., 10/27 | JV Girls Soccer | Derby | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | Cancelled | Cancelled | |
| Tue., 10/27 | V Girls Swimming and Diving | Torrington | Home - Woodland HS Pool [Directions] | 5:00 p.m. | ||
| Wed., 10/28 | FR Football | Wilby | Away - Wilby H.S. [Directions] | Cancelled | Cancelled | |
| Wed., 10/28 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/28 | JV Girls Volleyball | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 4:45 p.m. | W 2-0 | |
| Thu., 10/29 | JV Boys Soccer | Seymour | Home - Woodland Soccer Field [Directions] | 3:30 p.m. | ||
| Thu., 10/29 | V Girls Soccer | Seymour | Away - Seymour High Main Field [Directions] | 6:00 p.m. | W 5-1 | |
| Thu., 10/29 | JV Girls Soccer | Seymour | Away - Seymour High Lower Field [Directions] | Cancelled | Cancelled | |
| Fri., 10/30 | V Football | Wilby | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 39-6 | |
| Fri., 10/30 | JV Girls Volleyball | Naugy JV Tournament | Away - Naugatuck HS | 3:00 p.m. | two taems entered | |
| Sat., 10/31 | V Boys Cross Country | CIAC Class SS Championship | Away - Wickham Park - East Hartford [Directions] | 1:35 p.m. | ||
| Sat., 10/31 | V Boys Cross Country | Class Chammpionships | Away - TBA | 3:45 p.m. | ||
| Sat., 10/31 | JV Football | Wilby | Away - Wilby H.S. [Directions] | 10:00 a.m. | Froshm,ore Game | |
| Sat., 10/31 | V Boys Soccer | Ansonia | Away - Watertown HS [Directions] | 12:00 p.m. | ||
| Sat., 10/31 | V Girls Cross Country | Class Chammpionships | Away - TBA | 3:45 p.m. | ||
| Sat., 10/31 | V Girls Soccer | Seymour | Away - Municipal Stadium [Directions] | 3:00 p.m. | W 8-0 | |
| Sat., 10/31 | V Girls Volleyball | Ansonia | Home - Woodland HS Gym [Directions] | 11:00 a.m. | nvl quarter-finals | |
| Mon., 11/2 | V Girls Soccer | St. Paul Catholic | Away - Municipal Stadium [Directions] | 7:30 p.m. | W 2-0 | NVL Semi-Finals |
| Tue., 11/3 | V Boys Soccer | Oxford | Away - Municipal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 11/3 | V Girls Volleyball | Torrington | Home - Woodland HS Gym [Directions] | 5:00 p.m. | NVL Semi-Finals | |
| Thu., 11/5 | V Boys Soccer | Naugatuck | Away - Municipal Stadium [Directions] | 7:30 p.m. | NVL Championship | |
| Thu., 11/5 | V Girls Soccer | Watertown | Away - Municipal Stadium [Directions] | 5:30 p.m. | NVL Championship | |
| Thu., 11/5 | V Girls Soccer | NVL Championship Game | Away - Municipal Stadium | 5:30 p.m. | ||
| Thu., 11/5 | V Girls Volleyball | Oxford | Away - Kennedy HS [Directions] | 7:00 p.m. | NVL Championships | |
| Fri., 11/6 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Fri., 11/6 | V Football | Naugatuck | Home - Woodland Football Field [Directions] | 6:30 p.m. | W 50-24 | |
| Sat., 11/7 | V Boys Cross Country | State Open Championships | Away - TBA | 3:45 p.m. | ||
| Sat., 11/7 | JV Football | Naugatuck | Away - Naugatuck HS [Directions] | 10:00 a.m. | Froshmore Game | |
| Sat., 11/7 | V Girls Cross Country | State Open Championships | Away - TBA | 3:45 p.m. | ||
| Mon., 11/9 | V Girls Soccer | Shelton (Scrim.) | Away - Shelton HS [Directions] | 3:45 p.m. | ||
| Mon., 11/9 | V Girls Volleyball | Torrington (Scrim.) | Away - Torrington HS [Directions] | 3:15 p.m. | ||
| Tue., 11/10 | V Boys Soccer | Ansonia | Away - Ansonia Soccer Field [Directions] | 2:00 p.m. | First Round State tournament | |
| Tue., 11/10 | V Girls Volleyball | Amity (Scrim.) | Home - Woodland HS Gym [Directions] | 3:00 p.m. | ||
| Wed., 11/11 | V Girls Soccer | Rocky Hill | Home - Woodland HS [Directions] | 2:00 p.m. | W 2-1 (PKs 8-7) | |
| Wed., 11/11 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Middletown HS [Directions] | Cancelled | Cancelled | |
| Wed., 11/11 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Fri., 11/13 | V Football | Kennedy | Away - Municipal Stadium [Directions] | 7:00 p.m. | W 48-13 | |
| Fri., 11/13 | V Girls Soccer | Stonington | Home - Woodland Soccer Field [Directions] | 2:00 p.m. | W 4-1 | |
| Fri., 11/13 | V Girls Volleyball | Rockville | Home - Woodland HS Gym [Directions] | 5:00 p.m. | ||
| Sat., 11/14 | V Boys Cross Country | New England Championship | Away - Thetford Academy (VT) [Directions] | TBA | ||
| Sat., 11/14 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | Cancelled | Cancelled | |
| Sat., 11/14 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 2:00 p.m. | ||
| Mon., 11/16 | JV Football | Kennedy | Home - Woodland Football Field [Directions] | 3:45 p.m. | Froshmore Game | |
| Tue., 11/17 | V Girls Soccer | State semi-finals vs Enfield | Away - Middletown HS | 6:30 p.m. | ||
| Tue., 11/17 | V Girls Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | Cancelled | Cancelled | |
| Tue., 11/17 | V Girls Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 7:00 p.m. | ||
| Wed., 11/18 | V Girls Volleyball | State Semi-finals vs Waterford | Away - Guilford HS | 7:00 p.m. | ||
| Thu., 11/19 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | Cancelled | Cancelled | |
| Thu., 11/19 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/21 | JV Football | Seymour | Home - Woodland Football Field [Directions] | 10:00 a.m. | Froshmore Game | |
| Sat., 11/21 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | Cancelled | Cancelled | |
| Sat., 11/21 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Wed., 11/25 | V Football | Seymour | Away - Seymour High Main Field [Directions] | 6:00 p.m. | L 7-53 | |
| Sat., 12/5 | V Girls Basketball | Shepaug Valley (Scrim.) | Home - Woodland HS Gym [Directions] | 1:30 p.m. | ||
| Thu., 12/10 | V Girls Basketball | Griswold (Scrim.) | Away - Griswold [Directions] | 5:00 p.m. | ||
| Sat., 12/12 | V Boys Basketball | Thomaston (Scrim.) | Home - Woodland HS Gym [Directions] | 12:00 p.m. | ||
| Sat., 12/12 | V Wrestling | Southington (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Mon., 12/14 | V Boys Indoor Track | Wesleyan Developmental | Away - Wesleyan | 3:00 p.m. | ||
| Tue., 12/15 | V Boys Basketball | TBA | Away - Chase of Waterbury | 6:00 p.m. | ||
| Tue., 12/15 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | L 31-41 | |
| Tue., 12/15 | JV Girls Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Wed., 12/16 | V Wrestling | Foran | Away - Edna L. Fraser Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 12/17 | V Boys Basketball | Capital Prep Harbor | Home - Woodland HS Gym [Directions] | 6:15 p.m. | ||
| Fri., 12/18 | V Girls Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 41-27 | |
| Fri., 12/18 | JV Girls Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/18 | FR Girls Basketball | Naugatuck | Home [Directions] | Cancelled | Cancelled | |
| Sat., 12/19 | V Boys Indoor Track | Wilton Reindeer Relays | Away - Wilton HS | TBA | ||
| Sat., 12/19 | V Wrestling | Shelton Invitational Tournament | Away | 10:00 a.m. | Bus drop off and return (do not stay all day) | |
| Mon., 12/21 | V Boys Basketball | Oxford | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 33-71 | |
| Mon., 12/21 | JV Boys Basketball | Oxford | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | FR Boys Basketball | WCA | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/21 | V Wrestling | Xavier | Away - Xavier H.S. [Directions] | 7:00 p.m. | ||
| Mon., 12/21 | V Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 7:00 p.m. | W 41-23 | |
| Mon., 12/21 | JV Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/21 | Unified Sports Basketball | Oxford | Away - Oxford HS [Directions] | 3:00 p.m. | ||
| Wed., 12/23 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | L 37-70 | |
| Wed., 12/23 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | ||
| Wed., 12/23 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | ||
| Wed., 12/23 | V Girls Basketball | Kennedy | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 64-56 | |
| Wed., 12/23 | JV Girls Basketball | Kennedy | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/26 | V Boys Indoor Track | Hillhouse Relay | Away - Hillhouse | TBA | ||
| Mon., 12/28 | V Wrestling | Danbury Holiday Tournament | Away | 10:00 a.m. | Bus Drop off and return | |
| Mon., 12/28 | FR Girls Basketball | Crosby | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Tue., 12/29 | V Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 7:00 p.m. | W 45-21 | |
| Tue., 12/29 | JV Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | ||
| Wed., 12/30 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS [Directions] | 4:00 p.m. | Woodland 56 Crosby 31 | |
| Sat., 1/2 | V Boys Indoor Track | Shoreline Coaches | Away | TBA | ||
| Sat., 1/2 | V Wrestling | Southington Duals | Away | 10:00 a.m. | ||
| Mon., 1/4 | V Boys Indoor Track | Old Saybrook Developmental | Away - Hillhouse | TBA | ||
| Tue., 1/5 | V Boys Basketball | Wilby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | L 48-88 | |
| Tue., 1/5 | FR Boys Basketball | Wilby | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/5 | V Girls Basketball | Wilby | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 71-20 | |
| Wed., 1/6 | V Wrestling | Daniel Hand | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:30 p.m. | ||
| Wed., 1/6 | V Girls Basketball | Kaynor Tech | Away - Kaynor Tech [Directions] | 7:00 p.m. | W 47-42 | |
| Wed., 1/6 | JV Girls Basketball | Kaynor Tech | Away - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/7 | V Boys Basketball | HMTCA | Away - The Learning Corridor [Directions] | 7:00 p.m. | W 62-51 | |
| Thu., 1/7 | JV Boys Basketball | HMTCA | Away - The Learning Corridor [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | V Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | W 71-54 | |
| Fri., 1/8 | JV Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/8 | V Boys Indoor Track | SCSU Developmental | Away - Southern | TBA | ||
| Fri., 1/8 | V Boys Swimming and Diving | Seymour | Away - Seymour HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | V Girls Basketball | Derby | Away - Woodland HS Gym [Directions] | 5:15 p.m. | W 57-37 | |
| Fri., 1/8 | JV Girls Basketball | Derby | Home - Woodland HS Gym [Directions] | Cancelled | Cancelled | |
| Sat., 1/9 | V Boys Indoor Track | fresh/soph relays | Away - Glastonbury HS | TBA | ||
| Sat., 1/9 | V Wrestling | Natick Invitational Tournament | Away | 10:00 a.m. | ||
| Mon., 1/11 | V Boys Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 49-99 | |
| Mon., 1/11 | JV Boys Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/11 | FR Boys Basketball | Sacred Heart | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Mon., 1/11 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | W 37-30 | |
| Mon., 1/11 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Tue., 1/12 | V Wrestling | New Haven Wrestling | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:30 p.m. | ||
| Wed., 1/13 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 50-53 | |
| Wed., 1/13 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Wed., 1/13 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | ||
| Wed., 1/13 | V Boys Swimming and Diving | Northwestern | Home - Woodland HS Pool [Directions] | 4:30 p.m. | ||
| Wed., 1/13 | V Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 39-44 | |
| Wed., 1/13 | JV Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/13 | FR Girls Basketball | St. Paul Catholic | Home - Woodland HS Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 46-65 | |
| Fri., 1/15 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Fri., 1/15 | FR Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 3:00 p.m. | ||
| Fri., 1/15 | V Boys Indoor Track | NVL Developmental | Away - Wesleyan | TBA | two buses | |
| Fri., 1/15 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Girls Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 64-25 | |
| Fri., 1/15 | JV Girls Basketball | Ansonia | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/16 | V Boys Indoor Track | HK Meet | Away - Hillhouse | TBA | ||
| Sat., 1/16 | V Wrestling | Gilbert | Away - Gilbert HS | 10:00 a.m. | ||
| Tue., 1/19 | V Boys Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 63-92 | |
| Tue., 1/19 | JV Boys Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | Holy Cross | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/19 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 41-83 | |
| Tue., 1/19 | JV Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Wed., 1/20 | V Boys Swimming and Diving | Naugatuck | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/20 | V Wrestling | Jonathan Law | Away - Jonathan Law HS Old Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/20 | FR Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | ||
| Thu., 1/21 | Unified Sports Basketball | Cheshire | Away - Cheshire HS [Directions] | 2:30 p.m. | pick up lower lot | |
| Fri., 1/22 | V Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 44-57 | |
| Fri., 1/22 | JV Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/22 | FR Boys Basketball | Watertown | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/22 | V Boys Swimming and Diving | Masuk | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | L 45-61 | |
| Fri., 1/22 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:30 p.m. | ||
| Sat., 1/23 | V Wrestling | New Milford Tournament | Away | Cancelled | Cancelled | |
| Mon., 1/25 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | L 39-55 | |
| Mon., 1/25 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | ||
| Mon., 1/25 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 3:30 p.m. | ||
| Mon., 1/25 | V Boys Indoor Track | NVL Championships | Away - Hillhouse | TBA | ||
| Mon., 1/25 | V Girls Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 52-59 | |
| Mon., 1/25 | JV Girls Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Mon., 1/25 | Unified Sports Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/26 | FR Boys Basketball | Seymour | Home - Woodland HS Gym [Directions] | 3:00 p.m. | ||
| Tue., 1/26 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | ||
| Tue., 1/26 | V Wrestling | East Haven | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:30 p.m. | ||
| Wed., 1/27 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | W 71-67 | |
| Wed., 1/27 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 1/27 | V Girls Basketball | Seymour | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 51-49 | |
| Wed., 1/27 | JV Girls Basketball | Seymour | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/29 | V Boys Basketball | Crosby | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 45-87 | |
| Fri., 1/29 | JV Boys Basketball | Crosby | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/29 | V Boys Indoor Track | Hillhouse Developmental | Away - Hillhouse | TBA | ||
| Fri., 1/29 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/29 | V Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 33-37 | |
| Fri., 1/29 | JV Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Sat., 1/30 | FR Boys Basketball | Crosby | Home - Woodland HS Gym [Directions] | 12:30 p.m. | ||
| Sat., 1/30 | V Wrestling | Ridgefield Challenge | Away | 10:00 a.m. | ||
| Tue., 2/2 | V Boys Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | L 40-85 | |
| Tue., 2/2 | JV Boys Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Tue., 2/2 | FR Boys Basketball | Torrington | Away - Torrington HS [Directions] | 3:30 p.m. | ||
| Tue., 2/2 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:00 p.m. | ||
| Tue., 2/2 | V Wrestling | Cheshire | Away - Cheshire High East Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/2 | V Girls Basketball | Torrington | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 42-29 | |
| Tue., 2/2 | JV Girls Basketball | Torrington | Home - Woodland HS Gym [Directions] | 4:45 p.m. | ||
| Tue., 2/2 | Unified Sports Basketball | Torrington | Home - Woodland HS Gym [Directions] | 6:00 p.m. | ||
| Sat., 2/6 | V Wrestling | Foran Duals | Away | 10:00 a.m. | Drop off and pick up at Foran at 3:30 | |
| Mon., 2/8 | FR Girls Basketball | Naugatuck | Away [Directions] | Cancelled | Cancelled | |
| Mon., 2/8 | FR Girls Basketball | Naugatuck | Away [Directions] | Cancelled | Cancelled | |
| Tue., 2/9 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | L 44-65 | |
| Tue., 2/9 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Tue., 2/9 | FR Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 3:30 p.m. | ||
| Tue., 2/9 | V Boys Swimming and Diving | Holy Cross | Home - Woodland HS Pool [Directions] | 5:00 p.m. | ||
| Tue., 2/9 | V Girls Basketball | Watertown | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 25-34 | |
| Tue., 2/9 | JV Girls Basketball | Watertown | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/9 | FR Girls Basketball | Watertown | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/10 | V Wrestling | Fairfield Prep | Home - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 6:30 p.m. | ||
| Thu., 2/11 | V Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 30-58 | |
| Thu., 2/11 | JV Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/11 | FR Boys Basketball | Wolcott | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/11 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | W 48-42 | |
| Thu., 2/11 | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | V Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 7:00 p.m. | W 67-53 | |
| Fri., 2/12 | JV Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Boys Basketball | Naugatuck | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/12 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | W 40-31 | |
| Fri., 2/12 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:30 p.m. | ||
| Fri., 2/12 | FR Girls Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Sat., 2/13 | V Wrestling | S.C.C. Tournament | Away - Wilbur Cross HS | 9:00 a.m. | ||
| Wed., 2/17 | V Boys Basketball | Joel Barlow | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 27-45 | |
| Wed., 2/17 | JV Boys Basketball | Joel Barlow | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/17 | V Boys Swimming and Diving | Oxford | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Thu., 2/18 | FR Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 3:15 p.m. | ||
| Fri., 2/19 | V Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 7:00 p.m. | L 37-79 | |
| Fri., 2/19 | JV Boys Basketball | Torrington | Home - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/19 | V Boys Swimming and Diving | Torrington | Home - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/19 | V Wrestling | CIAC Class LL State Tournament | Away - Trumbull HS | 4:30 p.m. | will be returning at approx. 8:00 p.m., bus to stay after drop off | |
| Sat., 2/20 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/20 | V Wrestling | CIAC Class LL State Tournament | Away - Trumbull HS | 9:00 a.m. | Bus to drop off and return at 7:30 p.m. | |
| Sat., 2/20 | V Girls Basketball | Kennedy | Away - Holy Cross HS Gym [Directions] | 1:45 p.m. | ||
| Mon., 2/22 | FR Boys Basketball | Joel Barlow | Home - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/23 | Unified Sports Basketball | Naugatuck | Away - Naugatuck [Directions] | 6:00 p.m. | ||
| Thu., 2/25 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 26-63 | |
| Thu., 2/25 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:30 p.m. | ||
| Thu., 2/25 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | ||
| Fri., 2/26 | V Wrestling | CIAC State Open Tournament | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 2/27 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away - Plainville HS | TBA | ||
| Sat., 2/27 | V Wrestling | CIAC State Open Tournament | Away - Floyd Little Athletic Center | 9:00 a.m. | ||
| Sun., 2/28 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Tue., 3/1 | V Boys Swimming and Diving | NVL Tournament Trials | Away - Kennedy HS | 4:00 p.m. | ||
| Wed., 3/2 | V Boys Swimming and Diving | NVL Tournament Diving Championships | Away - Kennedy HS | 6:00 p.m. | ||
| Fri., 3/4 | V Boys Swimming and Diving | NVL Swim Championships | Away - Kennedy HS | 4:00 p.m. | ||
| Fri., 3/4 | V Wrestling | New England Tournament | Away - TBA | Cancelled | Cancelled | |
| Sat., 3/5 | V Wrestling | New England Tournament | Away - TBA | Cancelled | Cancelled | |
| Wed., 3/9 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Thu., 3/10 | Unified Sports Basketball | NVL Tournament | Away - Torrington HS | 3:00 p.m. | ||
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 3:30 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Wed., 3/23 | V Softball | Trumbull (Scrim.) | Home - Woodland Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/23 | JV Softball | Trumbull (Scrim.) | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:00 p.m. | ||
| Thu., 3/24 | V Baseball | Branford (Scrim.) | Away - James L. MacVeigh Alumni Athletic Complex - Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/24 | JV Baseball | Branford (Scrim.) | Away - Branford HS [Directions] | 3:30 p.m. | subvarsity game | |
| Fri., 3/25 | V Baseball | Hopkinson New Hampshire | Home - Woodland HS Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 3/26 | V Baseball | Holy Cross (Scrim.) | Away - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | V Baseball | Hopkinson New Hampshire | Home - Woodland HS Baseball Field [Directions] | 1:30 p.m. | ||
| Mon., 3/28 | V Baseball | Kaynor Tech (Scrim.) | Home - Woodland HS Baseball Field [Directions] | Cancelled | Cancelled | |
| Tue., 3/29 | V Baseball | WCA (Scrim.) | Away - Bucks Hill [Directions] | 3:30 p.m. | ||
| Tue., 3/29 | V Softball | Nonnewaug (Scrim.) | Home - Woodland Softball Field [Directions] | 3:30 p.m. | ||
| Wed., 3/30 | V Baseball | East Hartford (Scrim.) | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 3/30 | V Girls Tennis | Lewis Mills (Scrim.) | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | ||
| Wed., 4/6 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | 3:30 p.m. | L 1-3 | |
| Wed., 4/6 | V Boys Outdoor Track | Kaynor Tech, Bullard Havens Tech | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Wed., 4/6 | V Girls Outdoor Track | Kaynor Tech, Bullard Havens Tech | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Wed., 4/6 | V Softball | Oxford | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | L 2-3 | |
| Wed., 4/6 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 4/8 | V Boys Tennis | Naugatuck | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 3-6 | |
| Fri., 4/8 | V Softball | Kennedy | Away - Huntington Field [Directions] | 3:30 p.m. | W 25-7 | |
| Fri., 4/8 | JV Softball | Kennedy | Away - Huntington Field [Directions] | 3:30 p.m. | ||
| Fri., 4/8 | V Girls Tennis | Seymour | Away - Seymour HS [Directions] | 3:30 p.m. | W 4-3 | |
| Sat., 4/9 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | 1:00 p.m. | L 1-4 | |
| Sat., 4/9 | FR Baseball | Torrington | Away - Torrington HS [Directions] | 1:00 p.m. | ||
| Sat., 4/9 | V Softball | Torrington | Home - Woodland Softball Field [Directions] | 12:00 p.m. | L 0-10 | |
| Mon., 4/11 | V Boys Tennis | Sacred Heart | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 3-6 | |
| Mon., 4/11 | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | 3:30 p.m. | W 6-1 | |
| Tue., 4/12 | V Boys Golf | Crosby | Home - Oxford Greens [Directions] | 2:45 p.m. | Woodland 176 Crosby 286 Woodland Ryan Warner 39 Zach Crowell 45 Julian Perino 42 Alec Feducia 50 Crosby Michelle Escobar 72 Sophia Vega 72 Michael Garcia 72 Eileen Escobar 68 | |
| Tue., 4/12 | V Boys Outdoor Track | Crosby, Sacred Heart, St. Paul Catholic | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Tue., 4/12 | V Girls Outdoor Track | Crosby, Sacred Heart, St. Paul Catholic | Home - Woodland HS Track [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Baseball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | W 13-3 | |
| Wed., 4/13 | FR Baseball | Naugatuck | Away - Rotary Field [Directions] | 4:30 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | W 7-2 | |
| Wed., 4/13 | V Softball | Wilby | Home - Woodland Softball Field [Directions] | 3:30 p.m. | W 21-2 | |
| Wed., 4/13 | V Girls Tennis | Wilby | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 4/14 | V Baseball | Goodwin Tech | Away - Goodwin Tech HS Field [Directions] | 4:00 p.m. | L 3-5 | |
| Thu., 4/14 | JV Baseball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Thu., 4/14 | V Boys Golf | Waterbury Coop | Away [Directions] | 2:30 p.m. | Woodland Ryan Warner 49 Zach Crowell 41 Julian Perino 44 Alec Feducia 55 Kennedy Kyle Cleary Dylan McGrath Ansel McKinney Tyler Riccioni | Wilby at meet but scoring for Kennedy only |
| Thu., 4/14 | V Boys Outdoor Track | AT vacation invitational | Away - East Hartford | TBA | 1 bus | |
| Thu., 4/14 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | W 7-0 | |
| Fri., 4/15 | V Baseball | Derby | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 15-2 | |
| Fri., 4/15 | V Softball | Derby | Away - Derby- Ryan Athletic Complex- softball field [Directions] | 4:00 p.m. | W 20-0 | |
| Fri., 4/15 | V Girls Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | W 5-2 | |
| Sat., 4/16 | V Baseball | Naugatuck | Home - Woodland HS Baseball Field [Directions] | 10:00 a.m. | W 8-5 | |
| Sat., 4/16 | JV Baseball | Derby | Home - Woodland HS Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 4/16 | FR Baseball | Naugatuck | Home - Naugatuck HS [Directions] | 10:00 a.m. | ||
| Mon., 4/18 | V Baseball | Sacred Heart | Away - Fulton Park | 3:30 p.m. | L 1-4 | |
| Mon., 4/18 | V Boys Tennis | Kaynor Tech | Away - Bucks Hill park [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 4/18 | V Softball | Sacred Heart | Home - Woodland Softball Field [Directions] | 3:30 p.m. | W 8-5 | |
| Mon., 4/18 | V Girls Tennis | Sacred Heart | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 3-4 | |
| Tue., 4/19 | JV Baseball | Sacred Heart | Away - Fulton Park | 3:30 p.m. | ||
| Tue., 4/19 | V Boys Outdoor Track | Derby, Oxford, Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 4/19 | V Boys Tennis | Kennedy | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 8-1 | |
| Tue., 4/19 | V Girls Outdoor Track | Derby, Oxford, Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | L 2-6 | |
| Wed., 4/20 | FR Baseball | St. Paul Catholic | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Boys Tennis | Kennedy | Away - Chase Park [Directions] | 11:00 a.m. | W 8-1 | |
| Wed., 4/20 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 6-11 | |
| Wed., 4/20 | V Girls Tennis | St. Paul Catholic | Away - Peck Park, Bristol [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 4/21 | JV Baseball | St. Paul Catholic | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Baseball | Ansonia | Home - Woodland HS Baseball Field [Directions] | 1:00 p.m. | L 12-14 | |
| Fri., 4/22 | FR Baseball | Ansonia | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 1:00 p.m. | ||
| Fri., 4/22 | V Softball | Ansonia | Away - Ansonia HS [Directions] | 3:00 p.m. | W 22-1 | |
| Sat., 4/23 | JV Baseball | Ansonia | Home - Woodland HS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/23 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | 12:00 p.m. | W 6-0 | |
| Sat., 4/23 | JV Softball | Naugatuck | Away - Naugatuck HS [Directions] | 2:00 p.m. | ||
| Mon., 4/25 | V Baseball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 4-7 | |
| Mon., 4/25 | FR Baseball | Holy Cross | Away - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 0-9 | |
| Mon., 4/25 | V Softball | Holy Cross | Home - Woodland Softball Field [Directions] | 3:30 p.m. | L 5-6 | |
| Mon., 4/25 | V Girls Tennis | Holy Cross | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 6-1 | |
| Wed., 4/27 | V Baseball | Watertown | Away - Deland Field [Directions] | 3:30 p.m. | L 2-4 | |
| Wed., 4/27 | FR Baseball | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Boys Outdoor Track | Wilby, Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Wilby | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 9-0 | |
| Wed., 4/27 | V Girls Outdoor Track | Wilby, Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | ||
| Wed., 4/27 | V Softball | Watertown | Home - Woodland Softball Field [Directions] | 3:30 p.m. | W 4-3 | |
| Thu., 4/28 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | ||
| Thu., 4/28 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | 2:45 p.m. | Woodland Ryan Warner 46 Zach Crowell 45 Julian Perino 42 Josh Hassan 46 Sacred Heart Fran Fahy 48 James Gruszka 44 Anthony Corbo 45 John Keane 47 | |
| Thu., 4/28 | JV Softball | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Fri., 4/29 | V Baseball | Wolcott | Home - Woodland HS Baseball Field [Directions] | 3:45 p.m. | L 5-8 | |
| Fri., 4/29 | FR Baseball | Wolcott | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Wolcott | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | L 1-8 | boys/girls double header |
| Fri., 4/29 | V Softball | Wolcott | Away - George Babcock Field, Wolcott HS [Directions] | 4:00 p.m. | W 8-5 | |
| Fri., 4/29 | V Girls Tennis | Wolcott | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | L 3-4 | boys/girls double header |
| Sat., 4/30 | JV Baseball | Wolcott | Home - Woodland HS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/30 | JV Softball | Wolcott | Away - Wolcott HS [Directions] | 10:00 a.m. | ||
| Mon., 5/2 | V Boys Golf | Holy Cross | Away - Western Hills [Directions] | 2:30 p.m. | Woodland Ryan Warner 42 Julian Perino 46 Chris Guerrette 48 Zach Crowell 43 Holy Cross Alex Matos 41 Vincent Graziano 43 Greg Picard 45 Chris Ford 48 | |
| Mon., 5/2 | V Softball | Seymour | Away - Seymour HS [Directions] | 5:00 p.m. | L 2-6 | |
| Mon., 5/2 | JV Softball | Seymour | Away - Bungay School [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Boys Golf | Kaynor Tech | Away - East Mountain Golf Course [Directions] | 2:00 p.m. | Woodland Ryan Warner 41 Julian Perino 43 Alec Feducia 47 Josh Hassan 48 Kaynor Tech. Ryan Pelletier 49 Tim Mcallen 54 George Psstorok 49 John Mader 57 | |
| Tue., 5/3 | V Boys Outdoor Track | WCA, Seymour, Kennedy | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | WCA, Seymour, Kennedy | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Wed., 5/4 | V Baseball | Crosby | Away - Crosby HS [Directions] | 3:45 p.m. | W 20-0 | |
| Wed., 5/4 | FR Baseball | Holy Cross | Away - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 5/4 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | 2:45 p.m. | Woodland 177 Julian Perino 39- Medalist Zach Crowell 41 Josh Hassan 45 Chris Guerrette 48 Wolcott 185 Kyle Fishbein 41 Preston Lavoie 42 Mason Cipriano 48 Jack Gould 54 | |
| Wed., 5/4 | V Boys Tennis | Crosby | Away - Crosby HS [Directions] | 3:30 p.m. | W 9-0 | |
| Wed., 5/4 | V Softball | Crosby | Home - Woodland Softball Field [Directions] | 3:30 p.m. | W 17-2 | |
| Thu., 5/5 | V Baseball | Kennedy | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 8-1 | |
| Thu., 5/5 | JV Baseball | Crosby | Away - Crosby HS [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Golf | Woodland Invitational | Home - Oxford Greens [Directions] | 8:00 a.m. | ||
| Thu., 5/5 | V Boys Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | 3:30 p.m. | L 3-6 | |
| Thu., 5/5 | V Girls Tennis | Ansonia | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 7-0 | |
| Fri., 5/6 | JV Softball | Torrington | Away - Torrington HS [Directions] | Cancelled | Cancelled | |
| Sat., 5/7 | V Boys Outdoor Track | Middletown Invitational | Away - Middletown HS | TBA | ||
| Mon., 5/9 | V Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | W 9-6 | |
| Mon., 5/9 | FR Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | ||
| Mon., 5/9 | V Boys Golf | Wilby, Watertown | Home - Oxford Greens [Directions] | 2:45 p.m. | Woodland 197 Ryan Warner 45 Josh Hassan 47 Alec Feducia 52 Julian Perino Watertown 168 Zach Corderra 40 Mike Buckley 42 Anthony Guererra 42 Tom Labbe 44 | |
| Mon., 5/9 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | L 3-6 | |
| Mon., 5/9 | V Softball | Naugatuck | Home - Woodland Softball Field [Directions] | 3:45 p.m. | L 1-5 | |
| Mon., 5/9 | JV Softball | Naugatuck | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Mon., 5/9 | V Girls Tennis | Seymour | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 4-3 | |
| Tue., 5/10 | V Baseball | Seymour | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | W 8-6 | |
| Tue., 5/10 | FR Baseball | Seymour | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Tue., 5/10 | V Boys Golf | East Hampton | Home - Oxford Greens [Directions] | 2:45 p.m. | Woodland 167 Josh Hassan 40 -Medalist Julian Perino 40 Alec Feducia 43 Ryan Warner 44 East Hampton 234 Mike DeZinno 53 Liam Curtin 55 Nate Goff 58 Kurt Sturmer 68 | |
| Tue., 5/10 | V Boys Outdoor Track | Holy Cross, Naugatuck, Watertown | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | L 0-9 | |
| Tue., 5/10 | V Girls Outdoor Track | Holy Cross, Naugatuck, Watertown | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Crosby | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | W 5-2 | |
| Wed., 5/11 | V Baseball | Watertown | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | L 2-9 | |
| Wed., 5/11 | FR Baseball | Watertown | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 5/11 | V Boys Golf | Stigberg Memorial | Away - Farmingbury Hills Country Club | 9:00 a.m. | Zach Crowell Ryan Warner 76 | |
| Wed., 5/11 | V Boys Tennis | Watertown | Home - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 4-5 | |
| Wed., 5/11 | V Softball | Watertown | Away - Watertown HS [Directions] | 3:30 p.m. | L 5-8 | |
| Wed., 5/11 | V Girls Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | 3:30 p.m. | L 3-4 | |
| Thu., 5/12 | JV Baseball | Watertown | Home - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 5/12 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 2:45 p.m. | Woodland 183 Ryan Warner 47 Julian Perino 41 Josh Hassan 55 Zach Crowell 43 Holy Cross 180 | |
| Thu., 5/12 | V Boys Tennis | Torrington | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | L 3-6 | |
| Thu., 5/12 | V Boys Tennis | Torrington | Away - Torrington HS [Directions] | 5:00 p.m. | L 1-8 | |
| Thu., 5/12 | V Softball | Wolcott | Home - Woodland HS Varsity Field [Directions] | 3:30 p.m. | L 7-9 | |
| Fri., 5/13 | V Girls Tennis | Torrington | Home - Woodland HS Tennis courts [Directions] | 3:45 p.m. | W 4-0 | |
| Sat., 5/14 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | 12:00 p.m. | L 1-3 | |
| Sat., 5/14 | JV Baseball | Wolcott | Away - Wolcott HS [Directions] | 3:00 p.m. | ||
| Sat., 5/14 | JV Softball | Holy Cross | Home - Woodland Softball Field [Directions] | 10:30 a.m. | ||
| Mon., 5/16 | FR Baseball | Wolcott | Away - BAW [Directions] | 3:45 p.m. | ||
| Mon., 5/16 | V Boys Golf | Crosby | Away - East Mountain [Directions] | 2:30 p.m. | Woodland 180 Ryan Warner 47 Zach Crowell 43 Julian Perino 45 Josh Hassan 45 Crosby 260 | |
| Mon., 5/16 | V Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 5/16 | JV Softball | Coginchaug | Away - JV Softball Field @ CRHS [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Baseball | Torrington | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | W 12-4 | |
| Tue., 5/17 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | 2:45 p.m. | Woodland 177 Kennedy 266 Woodland Ryan Warner 44 Zach Crowell 46 Josh Hassan 42 Chris Guerrette 45 | |
| Tue., 5/17 | V Boys Outdoor Track | Platt Tech, O'Brien Tech | Home - Woodland HS Track [Directions] | 3:30 p.m. | Bullards Haven | |
| Tue., 5/17 | V Girls Outdoor Track | Platt Tech, O'Brien Tech | Home - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/17 | V Softball | Torrington | Away - Torrington HS [Directions] | 4:00 p.m. | L 6-9 | |
| Wed., 5/18 | V Baseball | Coginchaug | Home - Woodland HS Baseball Field [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 5/18 | JV Baseball | Coginchaug | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 4:00 p.m. | Sub-Varsity Game | |
| Wed., 5/18 | V Softball | Hamden | Away - HHS Softball Field [Directions] | 3:45 p.m. | W 12-1 | |
| Wed., 5/18 | JV Softball | Hamden | Away - Bassett Field [Directions] | 3:45 p.m. | ||
| Thu., 5/19 | FR Baseball | Torrington | Home - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Thu., 5/19 | V Boys Golf | St. Paul Catholic, Wilby | Away - Chippanee Golf Club [Directions] | 3:00 p.m. | Woodland 180 St. Paul 185 Ryan Warner 46 Zachary Crowell 43 Julian Perino 41 Josh Hassan 50 St. Paul Ryne Salius 41 Dan Stump 46 Sam Mozzarella 49 Paul Wiecki 49 | Wilby at meet for St. Paul only |
| Sat., 5/21 | V Softball | Seymour | Away - Seymour HS [Directions] | 11:00 a.m. | ||
| Mon., 5/23 | V Boys Tennis | Boys NVL Individual Tournament | Home [Directions] | 12:00 p.m. | ||
| Tue., 5/24 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | Woodland Zach Crowell 48 Julian Perino 45 Josh Hassan 42 Alec Feducia 49 Torrington Nick Paniati Adien Mattiello Carson Sparks Tyler Young Matt Calabrese | |
| Wed., 5/25 | V Baseball | Naugatuck (Scrim.) | Home - Woodland HS Baseball Field [Directions] | 3:15 p.m. | ||
| Wed., 5/25 | V Boys Golf | Sacred Heart | Away - East Mountain | 2:30 p.m. | Woodland Regional 174 Zach Crowell 42 Julian Perino 45 Ryan Warner 45 Josh Hassan 42 Sacred Heart 191 Sacred Heart Fran Fahy 46 James Gruszka 46 John Keane 52 Shea Zaccagnini 47 Woodland Regional Ryan Warner 45 Zach Corwell 42 (co-medalist) Julian Perino 45 Josh Hassan 42 (co-medalist) | |
| Wed., 5/25 | V Boys Tennis | nvl Boys Tennis Individual Championships | Away - Wolcott HS | 12:00 p.m. | ||
| Wed., 5/25 | V Softball | Wamogo/Litchfield (Scrim.) | Away - Wamogo Regional HS [Directions] | 3:30 p.m. | ||
| Wed., 5/25 | V Girls Tennis | Girls Individual NVL Tournament | Home - Woodland HS Tennis courts [Directions] | 12:00 p.m. | ||
| Thu., 5/26 | V Boys Golf | Chappa | Away | TBA | Julian Perino, Ryan Warner 87 | |
| Thu., 5/26 | V Girls Tennis | Girls Individual Tennis Championships | Home - Woodland HS Tennis courts [Directions] | 12:00 p.m. | ||
| Sat., 5/28 | V Baseball | Brookfield | Home - Woodland HS Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 5/28 | V Boys Tennis | Boys Tennis Preliminary States | Away - TBA | TBA | ||
| Sat., 5/28 | V Girls Tennis | Coginchaug | Home - Woodland HS Tennis courts [Directions] | 10:00 a.m. | ||
| Sat., 5/28 | V Girls Tennis | State Tennis Qualifying match | Away - TBA | TBA | ||
| Mon., 5/30 | V Boys Outdoor Track | O'Grady's | Away - Dnabury HS | TBA | ||
| Mon., 5/30 | V Girls Tennis | First Round Girls State Tournament | Away | TBA | ||
| Tue., 5/31 | V Boys Golf | Naugatuck | Home - Hop Brook [Directions] | 2:45 p.m. | Ryan47.0 Zach 51.0 Julian 40.0 Josh H.49.0 | |
| Tue., 5/31 | V Softball | Rocky Hill | Away - Elm Ridge Park [Directions] | 6:00 p.m. | ||
| Thu., 6/2 | V Boys Golf | NVL tournament | Away | TBA | ||