| Woodland 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 395 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Sat., 8/27 | V Football | Platt, Lyman Hall, SMSA Coop (Scrim.) | Away - Falcon Field (Meriden, CT)-Football Field [Directions] | 9:00 a.m. | ||
| Mon., 8/29 | V Boys Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Greens Farms Academy - Turf Blue | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Thu., 9/1 | V Football | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | 4:30 PM; 2 Buses | |
| Thu., 9/1 | V Girls Soccer | Jonathan Law (Scrim.) | Home - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/1 | V Girls Volleyball | Jonathan Law (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/3 | V Girls Volleyball | East Haven, Amity, Coginchaug, Fitch, Haddam-Killingworth, Nonnewaug, Sheehan | Away - East Haven HS-Gym | 9:00 a.m. | 7:30 AM; 1 Bus | |
| Tue., 9/6 | V Girls Volleyball | Northwestern (Scrim.) | Away - Northwestern Regional H.S.-Main Gym [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Wed., 9/7 | V Girls Volleyball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 3:45 p.m. | 2:45 PM; 1 Bus | |
| Thu., 9/8 | V Girls Swimming and Diving | Jonathan Law | Away - Foran HS -Pool [Directions] | Win - 95-83 | 4:00 PM; 1 Bus | |
| Thu., 9/8 | V Girls Volleyball | Brookfield | Home - Woodland HS-Gym [Directions] | W 3-1 | ||
| Fri., 9/9 | V Football | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | W 38-6 | 4:00 PM; 2 Buses | |
| Fri., 9/9 | V Girls Soccer | Watertown | Home - Woodland HS-Woodland Soccer Field [Directions] | W 5-2 | ||
| Sat., 9/10 | V Boys Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | T 1-1 | 8:45 AM; 1 Bus | |
| Mon., 9/12 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | L 1-3 | 4:00 PM; 1 Bus | |
| Tue., 9/13 | V Boys Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | W 3-0 | 4:15 PM; 1 Bus | |
| Tue., 9/13 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | W 3-1 | 4:00 PM; 1 Bus (Jv and Varsity on same bus) | |
| Wed., 9/14 | V Girls Soccer | Wolcott | Home - Woodland HS-Woodland Soccer Field [Directions] | W 5-0 | ||
| Fri., 9/16 | V Football | Ansonia | Away - Nolan Field-Ansonia-Football Field [Directions] | L 7-42 | 4:30 PM; 2 Buses | |
| Fri., 9/16 | V Boys Soccer | Ansonia | Home - Woodland HS-Woodland Soccer Field [Directions] | W 4-0 | ||
| Fri., 9/16 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Ave [Directions] | W 5-1 | 1:30 PM; 1 Bus (Dismiss athletes at 1:15) | |
| Fri., 9/16 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Home - Woodland HS-pool [Directions] | Win - 71-54 | ||
| Fri., 9/16 | V Girls Volleyball | Naugatuck | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Sat., 9/17 | V Boys Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | L 4-1 | 10:30 AM; 1 Bus | |
| Sat., 9/17 | V Girls Soccer | Pomperaug | Home - Woodland HS-Woodland Soccer Field [Directions] | L 0-1 | ||
| Mon., 9/19 | V Girls Volleyball | Pomperaug | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Tue., 9/20 | V Boys Cross Country | St. Paul Catholic, Kennedy, Torrington | Away - St. Paul Catholic HS -SP Track [Directions] | 3:45 p.m. | 2:15 PM; 1 Bus (boys and girls same bus) | |
| Tue., 9/20 | V Girls Cross Country | St. Paul Catholic, Kennedy, Torrington | Away - St. Paul Catholic HS -SP Track [Directions] | 3:45 p.m. | 2:15 PM; 1 Bus (boys and girls teams on same bus) | |
| Tue., 9/20 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland HS-pool [Directions] | Win - 88-64 | ||
| Wed., 9/21 | V Girls Soccer | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | T 3-3 | 2:15 PM; 1 Bus | |
| Wed., 9/21 | V Girls Volleyball | Torrington | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Fri., 9/23 | V Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | W 47-0 | 4:30 PM; 2 Buses | |
| Fri., 9/23 | V Boys Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | T 1-1 | ||
| Fri., 9/23 | V Girls Swimming and Diving | Seymour | Home - Woodland HS-pool [Directions] | Win - 95-75 | ||
| Fri., 9/23 | V Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | W 3-0 | 3:00 PM; 1 Bus (jv and varsity teams on same bus) | |
| Sat., 9/24 | V Girls Soccer | Lewis Mills | Away - Lewis Mills HS-Nassahegan Field [Directions] | L 4-5 | 11:15 AM; 1 Bus | |
| Tue., 9/27 | V Boys Cross Country | Holy Cross, Naugatuck, Wilby | Home - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | T 1-1 | 4:30 PM; 1 Bus | |
| Tue., 9/27 | V Girls Cross Country | Holy Cross, Naugatuck, Wilby | Home - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Torrington | Home - Woodland HS-Woodland Soccer Field [Directions] | W 8-0 | ||
| Tue., 9/27 | V Girls Swimming and Diving | Weston | Home - Woodland HS-pool [Directions] | Loss - 101 - 78 | ||
| Tue., 9/27 | V Girls Volleyball | Crosby | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Thu., 9/29 | V Boys Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | W 9-1 | 4:45 PM; 1 Bus | |
| Thu., 9/29 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | W 3-1 | 2:45 PM; 1 Bus (jv and varsity on same bus) | |
| Fri., 9/30 | V Football | Derby | Home - Woodland HS-Woodland Football Field [Directions] | W 57-0 | ||
| Fri., 9/30 | V Girls Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | W 9-0 | ||
| Fri., 9/30 | V Girls Swimming and Diving | Kennedy | Away - John F. Kennedy HS-John Reardon Pool [Directions] | Win 58-36 | 2:45 PM; 1 Bus | |
| Fri., 9/30 | V Girls Volleyball | Ansonia | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Sat., 10/1 | V Girls Swimming and Diving | Hall, Amity, Branford, Conard, Daniel Hand, East Lyme, Glastonbury, Southington | Away - Cornerstone Aquatics Center-Pool | 3:00 p.m. | 1:30 PM; 1 Bus | |
| Mon., 10/3 | V Boys Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | W 1-0 | ||
| Mon., 10/3 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | W 7-0 | 2:30 PM; 1 Bus | |
| Tue., 10/4 | V Girls Swimming and Diving | Oxford | Home - Woodland HS-pool [Directions] | Win 98 - 76 | ||
| Tue., 10/4 | V Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | W 3-1 | 2:45 PM; 1 Bus (jv and varsity on same bus) | |
| Wed., 10/5 | V Girls Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | W 1-0 | 5:30 PM; 1 Bus | |
| Thu., 10/6 | V Boys Cross Country | Crosby, Seymour, Watertown | Home - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | W 49-0 | 4:00 PM; 2 Buses | |
| Thu., 10/6 | V Boys Soccer | Kennedy | Home - Woodland HS-Woodland Soccer Field [Directions] | W 4-0 | ||
| Thu., 10/6 | V Girls Cross Country | Crosby, Seymour, Watertown | Home - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | L 0-3 | 3:15 PM; 1 Bus | |
| Fri., 10/7 | V Girls Soccer | Holy Cross | Home - Woodland HS-Woodland Soccer Field [Directions] | W 2-1 | ||
| Fri., 10/7 | V Girls Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | Win 87-72 | ||
| Fri., 10/7 | V Girls Volleyball | Wilby | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Tue., 10/11 | V Boys Cross Country | Oxford, Derby, WCA | Away - Oxford HS-OHS XC TRAIL [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus (boys and girls on same bus) | |
| Tue., 10/11 | V Boys Soccer | Wilby | Away - Wilby HS-Pedro DeBrito Field [Directions] | W 5-0 | 2:15 PM; 1 Bus | |
| Tue., 10/11 | V Girls Cross Country | Oxford, Derby, WCA | Away - Oxford HS-OHS XC TRAIL [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus (Boys and girls on same bus) | |
| Tue., 10/11 | V Girls Swimming and Diving | Suffield | Away - Windsor Locks HS-Pool- No diving [Directions] | Postponed | 2:15 PM; 1 Bus | |
| Tue., 10/11 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | W 3-0 | 4:00 PM; 1 Bus (jv and varsity on same bus) | |
| Wed., 10/12 | V Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Thu., 10/13 | V Boys Soccer | Portland | Home - Woodland HS-Woodland Soccer Field [Directions] | W 4-0 | ||
| Thu., 10/13 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | W 3-0 | 4:00 PM; 1 Bus | |
| Fri., 10/14 | V Boys Soccer | Crosby | Home - Woodland HS-Woodland Soccer Field [Directions] | W 2-0 | ||
| Fri., 10/14 | V Girls Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | W 1-0 | 4:15 PM; 1 Bus | |
| Fri., 10/14 | V Girls Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | 5:45 PM; 1 Bus | |
| Sat., 10/15 | V Boys Cross Country | Wolcott | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 10:00 a.m. | 2:20 PM; 1 Bus (Boys and Girls Cross Country on same bus) | |
| Sat., 10/15 | V Girls Cross Country | Wolcott | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 10:00 a.m. | 2:20 PM; 1 Bus | |
| Tue., 10/18 | V Boys Soccer | WCA | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | W 3-0 | 5:15 PM; 1 Bus | |
| Tue., 10/18 | V Girls Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | W 5-0 | 4:45 PM; 1 Bus | |
| Tue., 10/18 | V Girls Swimming and Diving | Watertown | Home - Woodland HS-pool [Directions] | 5:00 p.m. | 4:00 PM; 1 Bus | |
| Wed., 10/19 | V Boys Cross Country | NVL XC Championships | Away - Veterans Memorial Park-Veterans Park XC Course | 2:00 p.m. | ||
| Wed., 10/19 | V Girls Cross Country | NVL XC Championships | Away - Veterans Memorial Park-Veterans Park XC Course | 2:00 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Oxford | Home - Woodland HS-Woodland Soccer Field [Directions] | L 5-1 | ||
| Thu., 10/20 | V Girls Volleyball | Seymour | Home - Woodland HS-Gym [Directions] | W 3-2 | ||
| Fri., 10/21 | V Football | Wolcott | Home - Woodland HS-Woodland Football Field [Directions] | W 33-6 | ||
| Fri., 10/21 | V Girls Soccer | Naugatuck | Home - Woodland HS-Woodland Soccer Field [Directions] | W 8-2 | ||
| Fri., 10/21 | V Girls Swimming and Diving | Waterford | Away - Waterford HS-Pool - WHS [Directions] | 5:00 p.m. | 2:20 PM; 1 Bus | |
| Fri., 10/21 | V Girls Volleyball | Oxford | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Mon., 10/24 | V Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | T 2-2 | 4:45 PM; 1 Bus | |
| Mon., 10/24 | V Girls Soccer | Seymour | Home - Woodland HS-Woodland Soccer Field [Directions] | W 4-0 | ||
| Tue., 10/25 | V Girls Volleyball | Holy Cross | Home - Woodland HS-Gym [Directions] | W 3-0 | ||
| Wed., 10/26 | V Boys Soccer | St. Paul Catholic | Home - Woodland HS-Woodland Football Field [Directions] | L 3-2 | ||
| Wed., 10/26 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | W 3-0 | 4:45 PM; 1 Bus | |
| Thu., 10/27 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | W 8-0 | 4:00 PM; 1 Bus | |
| Fri., 10/28 | V Football | St. Paul Catholic | Home - Woodland HS-Woodland Football Field [Directions] | W 46-16 | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class SS Championship | Away - Wickham Park | 1:30 p.m. | ||
| Sat., 10/29 | V Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:00 p.m. | 12:00 PM | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park | 12:55 p.m. | ||
| Sat., 10/29 | V Girls Soccer | St. Paul Catholic | Home - Woodland HS-Woodland Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/29 | V Girls Volleyball | WCA | Home - Woodland HS-Gym [Directions] | 2:00 p.m. | ||
| Tue., 11/1 | V Girls Soccer | Wolcott | Home - Wolcott HS-Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | NVL SWIM TRIALS | Away - J F Kennedy HS Turf-John Reardon Pool | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Kennedy HS-John Reardon Pool | ||||||
| Tue., 11/1 | V Girls Volleyball | Holy Cross | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | NVL DIVING CHAMPIONSHIP | Away - Watertown HS-Frank M. Reinhold Pool | 6:00 p.m. | ||
| Thu., 11/3 | V Girls Soccer | Watertown | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 11/3 | V Girls Volleyball | Seymour | Away - Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Holy Cross | Home - Woodland HS-Woodland Football Field [Directions] | W 20-7 | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | NVL SWIM FINALS | Away - John F. Kennedy HS-John Reardon Pool | 4:30 p.m. | ||
| Mon., 11/7 | V Boys Soccer | Granby Memorial | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Tue., 11/8 | V Girls Soccer | Goodwin/Innovation | Home - Woodland HS-Woodland Soccer Field [Directions] | W 9-0 | ||
| Wed., 11/9 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/9 | V Girls Volleyball | Mercy | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/10 | V Girls Soccer | Northwest Catholic | Home - Woodland HS-Woodland Soccer Field [Directions] | 2:00 p.m. | ||
| Fri., 11/11 | V Football | Naugatuck | Home - Woodland HS-Woodland Football Field [Directions] | L 0-41 | ||
| Fri., 11/11 | V Girls Volleyball | Nonnewaug | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class S Trials | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Tue., 11/15 | V Girls Swimming and Diving | CIAC Class S Final | Away - SCSU | 6:00 p.m. | ||
| Tue., 11/15 | V Girls Volleyball | Waterford | Home - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 6:00 p.m. | ||
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | V Girls Volleyball | RHAM | Home - East Haven HS-Gym [Directions] | 7:00 p.m. | ||
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Wed., 11/23 | V Football | Seymour | Away - Seymour HS-turf field [Directions] | W 31-7 | 4:30 PM; 2 Buses | |
| Tue., 11/29 | V Football | East Catholic | Home - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:30 p.m. | ||
| Sat., 12/3 | V Wrestling | Shelton (Scrim.) | Home - Amity Regional HS-Middle Practice Gym [Directions] | 10:00 a.m. | ||
| Tue., 12/6 | V Boys Basketball | North Haven (Scrim.) | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 12/6 | V Girls Basketball | Thomaston, Bristol Central (Scrim.) | Away - Thomaston HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/8 | V Girls Basketball | Lyman Hall (Scrim.) | Home - Woodland HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/10 | V Wrestling | Southington, Middletown, Platt, Plainville (Scrim.) | Away - Southington HS-Gym West [Directions] | 8:00 a.m. | 6:00 AM; 1 Bus | |
| Mon., 12/12 | V Boys Basketball | Cheshire (Scrim.) | Away - Cheshire HS-Gym West [Directions] | 3:30 p.m. | 2:30 PM; 1 Bus | |
| Tue., 12/13 | V Girls Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | W 34-31 | 4:00 PM; 1 Bus | |
| Thu., 12/15 | V Boys Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Thu., 12/15 | V Girls Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Fri., 12/16 | V Boys Basketball | Wilby | Home - Woodland HS-Gym [Directions] | L 51-77 | ||
| Fri., 12/16 | V Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | W 50-18 | 4:00 PM; 1 Bus | |
| Sat., 12/17 | V Boys Indoor Track | NVL Meet @ Bethel HS | Away - Not Listed | TBA | TBA, Dismiss TBA | |
| Sat., 12/17 | V Wrestling | Guilford Invitational | Away - Guilford HS-Main gym at GHS | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 12/17 | V Girls Indoor Track | NVL Meet @ Bethel HS | Away - Not Listed | TBA | TBA, Dismiss TBA | |
| Tue., 12/20 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | L 66-67 | 3:30 PM; 1 Bus | |
| Tue., 12/20 | V Boys Swimming and Diving | Northwestern | Home - Woodland HS-pool [Directions] | Loss: 93-87 (0-1) | ||
| Tue., 12/20 | V Girls Basketball | Oxford | Home - Woodland HS-Gym [Directions] | L 39-51 | ||
| Wed., 12/21 | V Wrestling | East Haven | Away - East Haven HS-Gym [Directions] | 6:00 p.m. | 4:30 PM; 1 Bus | |
| Thu., 12/22 | V Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | L 51-67 | 4:00 PM; 1 Bus | |
| Thu., 12/22 | V Boys Indoor Track | Hillhouse Holiday Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | 2:15 PM, Dismiss TBA; 1 Bus | |
| Thu., 12/22 | V Girls Indoor Track | Hillhouse Holiday Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | 2:15 PM, Dismiss TBA; 1 Bus | |
| Tue., 12/27 | V Boys Basketball | Seymour | Home - Woodland HS-Gym [Directions] | L 51-59 | ||
| Tue., 12/27 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | W 45-38 | 4:15 PM; 1 Bus | |
| Thu., 12/29 | V Wrestling | GHS Duals | Away - Glastonbury HS-Gym | 9:00 a.m. | 7:30 AM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Fri., 12/30 | V Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | L 60-88 | 4:00 PM; 1 Bus | |
| Fri., 12/30 | V Boys Indoor Track | Bob Saulsbury Track Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | 8:00 AM, Dismiss TBA; 1 Bus | |
| Fri., 12/30 | V Wrestling | Trumbull, Berlin, Greenwich, Foran, Manchester, Masuk, Minnechaug (MA), TBA, Pomperaug, Stratford | Away - Trumbull HS-Aux Gym | 8:00 a.m. | 7:00 AM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Fri., 12/30 | V Girls Basketball | Holy Cross | Home - Woodland HS-Gym [Directions] | L 30-72 | ||
| Fri., 12/30 | V Girls Indoor Track | Bob Saulsbury Track Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | 8:00 AM, Dismiss TBA; 1 Bus | |
| Tue., 1/3 | V Boys Basketball | Derby | Home - Woodland HS-Gym [Directions] | W 70-61 | ||
| Tue., 1/3 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | W 61-12 | 5:00 PM; 1 Bus | |
| Wed., 1/4 | V Wrestling | New Haven Wrestling | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Girls Basketball | Wolcott | Home - Woodland HS-Gym [Directions] | L 30-35 | ||
| Fri., 1/6 | V Boys Basketball | Naugatuck | Home - Woodland HS-Gym [Directions] | L 71-77 | ||
| Fri., 1/6 | V Boys Swimming and Diving | Cheshire | Home - Woodland HS-pool [Directions] | Win: 93-79 (1-1) | ||
| Fri., 1/6 | V Boys Swimming and Diving | Crosby/WCA | Home - Woodland HS-pool [Directions] | Cancelled | ||
| Fri., 1/6 | V Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | L 38-48 | 4:15 PM; 1 Bus | |
| Sat., 1/7 | V Boys Indoor Track | Elm City Coaches Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | 7:00 AM, Dismiss TBA; 1 Bus | |
| Sat., 1/7 | V Wrestling | New Canaan, Newington, North Haven, New Haven Wrestling | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 9:00 a.m. | 2 mats | |
| Sat., 1/7 | V Girls Indoor Track | Elm City Coaches Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | 7:00 AM, Dismiss TBA; 1 Bus | |
| Tue., 1/10 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | L 32-62 | 3:15 PM; 1 Bus | |
| Tue., 1/10 | V Girls Basketball | Torrington | Home - Woodland HS-Gym [Directions] | W 34-27 | ||
| Wed., 1/11 | V Boys Swimming and Diving | Notre Dame-West Haven | Home - Woodland HS-pool [Directions] | Win: 94-89 (2-1) | ||
| Wed., 1/11 | V Wrestling | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Wed., 1/11 | V Girls Basketball | Seymour | Home - Woodland HS-Gym [Directions] | W 44-28 | ||
| Thu., 1/12 | V Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | L 52-77 | 4:15 PM; 1 Bus | |
| Fri., 1/13 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby HS-Gil Cyr Natatorium [Directions] | Cancelled | 4:15 PM; 1 Bus | |
| Fri., 1/13 | V Wrestling | Fairfield Warde, Brien McMahon, Joel Barlow | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 1/17 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | L 59-95 | 4:15 PM; 1 Bus | |
| Tue., 1/17 | V Girls Basketball | Crosby | Home - Woodland HS-Gym [Directions] | W 51-46 | ||
| Wed., 1/18 | V Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | W 79-71 | 4:00 PM; 1 Bus | |
| Wed., 1/18 | V Boys Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | 2:15 PM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Date to 1/19 | ||||||
| Wed., 1/18 | V Wrestling | Cheshire | Away - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Wed., 1/18 | V Girls Basketball | Kaynor Tech | Home - Woodland HS-Gym [Directions] | W 57-23 | ||
| Wed., 1/18 | V Girls Indoor Track | GHS Home Meet | Away - Glastonbury HS-Gym | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 1/19 | ||||||
| Fri., 1/20 | V Boys Swimming and Diving | Naugatuck | Home - Woodland HS-pool [Directions] | Win: 97-80 (3-1, 1-0 in NVL) | ||
| Sat., 1/21 | V Boys Indoor Track | SCC Coaches Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | TBA, Dismiss TBA | |
| Sat., 1/21 | V Wrestling | Branford, Bristol Eastern, Fairfield Prep, Killingly, Manchester, Morgan, Newington | Away - Branford HS-Gym | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 1/21 | Winter Dance Team | Norwich Free Academy | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/21 | V Girls Indoor Track | SCC Coaches Invite @ Floyd Little Athletic Center (Hillhouse HS) | Away - Not Listed-Floyd Little Athletic Center | TBA | TBA, Dismiss TBA | |
| Tue., 1/24 | V Boys Basketball | Kennedy | Home - Woodland HS-Gym [Directions] | L 55-66 | ||
| Tue., 1/24 | V Boys Indoor Track | Shoreline Coaches Invite @ Floyd Little Athletic Center (Hillhouse High School) | Away - Not Listed-Floyd Little Athletic Center | 3:00 p.m. | TBA, Dismiss TBA | |
| Tue., 1/24 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | W 58-47 | 4:00 PM; 1 Bus | |
| Tue., 1/24 | V Girls Indoor Track | Shoreline Coaches Invite @ Floyd Little Athletic Center (Hillhouse High School) | Away - Not Listed-Floyd Little Athletic Center | TBA | TBA, Dismiss TBA | |
| Thu., 1/26 | V Wrestling | Notre Dame-West Haven | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | St. Paul Catholic | Home - Woodland HS-Gym [Directions] | W 77-62 | ||
| Fri., 1/27 | V Boys Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Fri., 1/27 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | Win: 95-88 (4-1, 2-0 in NVL) | 4:15 PM; 1 Bus | |
| Fri., 1/27 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | L 38-55 | 4:00 PM; 1 Bus | |
| Fri., 1/27 | V Girls Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 a.m. | TBA; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Time to 5:15 p.m. | ||||||
| Sat., 1/28 | V Wrestling | Ridgefield, Arlington (NY), Bethel, Brewster (NY), Bristol Central, Coventry (RI), Fairfield Prep, Fairfield Warde, Greenwich, Hope (RI), Middlebury Union (VT), TBA, New Milford, Washingtonville (NY) | Away - Ridgefield HS-Main Gym | 9:30 a.m. | 6:30 AM; 1 Bus | |
| Tue., 1/31 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | L 56-94 | 4:00 PM; 1 Bus | |
| Tue., 1/31 | V Boys Swimming and Diving | Crosby/WCA, Seymour | Away - Woodland HS-pool [Directions] | Win vs. Seymour: 88-76 Win vs. Crosby. (6-1, 4-0 in NVL) | 4:45 PM; 1 Bus | |
| Tue., 1/31 | V Girls Basketball | WCA | Home - Woodland HS-Gym [Directions] | L 33-36 | ||
| Wed., 2/1 | V Boys Basketball | Nonnewaug | Home - Woodland HS-Gym [Directions] | L 46-65 | ||
| Wed., 2/1 | V Wrestling | Shelton | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 2/1 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | W 53-29 | 2:45 PM; 1 Bus | |
| Thu., 2/2 | Winter Dance Team | NVL Dance Championship | Home - Woodland HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Torrington | Home - Woodland HS-pool [Directions] | Win: 92-73 (7-1, 5-0 in NVL) | ||
| Sat., 2/4 | V Wrestling | Foran High School Duals | Away - Foran HS -Edna L. Fraser Gymnasium | 9:00 a.m. | 7:00 AM; 1 Bus (Drop off and pick up at approx. 2:30) | |
| Mon., 2/6 | V Boys Swimming and Diving | Holy Cross | Home - Woodland HS-pool [Directions] | Loss: 99-84 (7-2, 5-1 in NVL) | ||
| Mon., 2/6 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | ||
| Tue., 2/7 | V Boys Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | L 49-59 | ||
| Tue., 2/7 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | W 43-37 | 3:00 PM; 1 Bus | |
| Wed., 2/8 | V Wrestling | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 6:30 p.m. | 5:30 PM; 1 Bus | |
| Thu., 2/9 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/9 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Oxford | Home - Woodland HS-Gym [Directions] | L 54-63 | ||
| Fri., 2/10 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | L 42-46 | 3:00 PM; 1 Bus | |
| Sat., 2/11 | V Wrestling | Branford, Cheshire, Daniel Hand, East Haven, Fairfield Prep, Guilford, Jonathan Law, Foran, Morgan, North Haven, Notre Dame-West Haven, Shelton, New Haven Wrestling, Xavier | Away - Branford HS-Gym | 10:00 a.m. | 8:00 AM; 1 Bus (Return for pick up at approx. 5:00) | |
| Tue., 2/14 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | W 87-55 | 4:15 PM; 1 Bus | |
| Tue., 2/14 | V Girls Basketball | Derby | Home - Woodland HS-Gym [Directions] | W 51-14 | ||
| Wed., 2/15 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | L 49-78 | 2:45 PM; 1 Bus | |
| Wed., 2/15 | V Girls Basketball | Ansonia | Home - Woodland HS-Gym [Directions] | W 41-39 | ||
| Thu., 2/16 | V Boys Swimming and Diving | Oxford, Wilby/Kaynor | Home - Woodland HS-pool [Directions] | Win: 97-83 vs. Oxford Win vs. Wilby (9-2, 7-1 in NVL) | ||
| Fri., 2/17 | V Wrestling | CIAC S Championship | Away - Killingly | 4:00 p.m. | ||
| Fri., 2/17 | V Wrestling | CIAC L Championship | Away - Guilford | 4:00 p.m. | ||
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC S Championship | Away - Killingly | 10:30 a.m. | ||
| Sat., 2/18 | V Wrestling | CIAC L Championship | Away - Guilford | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Basketball | Torrington | Away - Kennedy HS [Directions] | 12:45 p.m. | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Tue., 2/21 | V Boys Swimming and Diving | Kennedy | Away - John F. Kennedy HS-John Reardon Pool [Directions] | Win: 77-55 (10-2, 8-1 in NVL) | 2:45 PM; 1 Bus | |
| Wed., 2/22 | V Boys Basketball | Watertown | Home - Woodland HS-Gym [Directions] | W 83-63 | ||
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Fri., 2/24 | V Girls Basketball | Naugatuck (Scrim.) | Home - Woodland HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Wed., 3/1 | V Girls Basketball | Canton | Home - Woodland HS-Gym [Directions] | 6:30 p.m. | ||
| Fri., 3/3 | V Girls Basketball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 4:30 p.m. | 2:00 PM; 1 Bus | |
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class S Trials | Away - East Hartford | 4:30 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class S Finals | Away - SCSU | 1:00 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Wed., 3/22 | V Softball | Brookfield (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 3:45 p.m. | ||
| Thu., 3/23 | V Baseball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | 2:15 PM | |
| Fri., 3/24 | V Baseball | North Branford (Scrim.) | Home - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Fri., 3/24 | V Softball | Cromwell (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 3/27 | V Softball | Trumbull (Scrim.) | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Tue., 3/28 | V Baseball | Stratford (Scrim.) | Away - Penders Field-Penders Field - Stratford [Directions] | 3:45 p.m. | 2:15 PM; 1 Bus | |
| Wed., 3/29 | V Softball | St. Joseph (Scrim.) | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Thu., 3/30 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 3:45 p.m. | 2:15 PM; 1 Bus | |
| Thu., 3/30 | V Softball | Cheshire (Scrim.) | Home - Woodland HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/3 | V Baseball | Torrington | Home - Woodland HS-Baseball Diamond [Directions] | W 6-0 | ||
| Mon., 4/3 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | W 4-1 [Detailed Results] | ||
| Mon., 4/3 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | W 10-2 | 2:15 PM; 1 Bus | |
| Mon., 4/3 | V Girls Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | W 4-3 | 2:15 PM; 1 Bus | |
| Tue., 4/4 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | W 11-8 | 2:15 PM; 1 Bus | |
| Tue., 4/4 | V Boys Outdoor Track | Naugatuck, Derby | Away - Naugatuck HS-Veterans Field [Directions] | Naugatuck 83 WRHS 67 WRHS 95. Derby 55 | ||
| Tue., 4/4 | V Girls Outdoor Track | Naugatuck, Derby | Away - Naugatuck HS-Veterans Field [Directions] | Naugatuck 87, WRHS 63 WRHS 131, Derby 19 | ||
| Tue., 4/4 | V Girls Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/5 | V Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | W 23-5 (5) | ||
| Wed., 4/5 | V Boys Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | W 4-1 [Detailed Results] | ||
| Wed., 4/5 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | W 11-3 | 2:15 PM; 1 Bus | |
| Wed., 4/5 | V Girls Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | L 2-5 | 2:15 PM; 1 Bus | |
| Thu., 4/6 | V Softball | Watertown | Home - Woodland HS-Softball Diamond [Directions] | W 3-2 | ||
| Sat., 4/8 | V Baseball | Watertown | Away - Deland Field-Deland field [Directions] | W 11-1 (5) | 9:30 AM; 1 Bus | |
| Mon., 4/10 | V Baseball | Wilby | Home - Woodland HS-Baseball Diamond [Directions] | W 16-0 (5) | ||
| Mon., 4/10 | V Boys Golf | Seymour, Oxford | Away - Seymour HS-Oxford Greens [Directions] | 2:00 p.m. | ||
| Mon., 4/10 | V Softball | Wilby | Away - Bucks Hill Park #1-Bucks Hill Park [Directions] | W 23-0 | 9:30 AM; 1 Bus | |
| Tue., 4/11 | V Boys Outdoor Track | Torrington | Away - Torrington HS [Directions] | WRHS 107, Torrington 43 | 8:15 AM | |
| Tue., 4/11 | V Boys Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Tue., 4/11 | V Boys Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Tue., 4/11 | V Girls Outdoor Track | Torrington | Away - Torrington HS [Directions] | WRHS 121, Torrington 29 | 8:15 AM | |
| Wed., 4/12 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | 2:00 p.m. | ||
| Thu., 4/13 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 3:00 p.m. | 2:00 PM | |
| Thu., 4/13 | V Boys Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Thu., 4/13 | V Softball | Ansonia | Home - Woodland HS-Softball Diamond [Directions] | W 19-0 | ||
| Fri., 4/14 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | W 7-5 | 11:15 AM; 1 Bus | |
| Fri., 4/14 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | W 5-0 | 2:00 PM; 1 Bus | |
| Fri., 4/14 | V Girls Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | L 2-5 | ||
| Sat., 4/15 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | W 10-3 | 9:00 AM | |
| Sat., 4/15 | V Softball | Pomperaug | Home - Woodland HS-Softball Diamond [Directions] | W 7-0 | ||
| Mon., 4/17 | V Baseball | Derby | Home - Woodland HS-Baseball Diamond [Directions] | W 9-6 | ||
| Mon., 4/17 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | W 15-0 | 2:15 PM; 1 Bus | |
| Tue., 4/18 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | L 14-6 | 2:15 PM; 1 Bus | |
| Tue., 4/18 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | 2:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Tue., 4/18 | V Boys Tennis | Watertown | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Tue., 4/18 | V Girls Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | W 7-0 | 2:30 PM; 1 Bus | |
| Wed., 4/19 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | 2:00 p.m. | ||
| Wed., 4/19 | V Softball | Wolcott | Home - Woodland HS-Softball Diamond [Directions] | W 9-3 | ||
| Fri., 4/21 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | W 10-1 | 4:30 PM; 1 Bus | |
| Fri., 4/21 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | W 5-0 | 2:15 PM; 1 Bus | |
| Fri., 4/21 | V Softball | Naugatuck | Home - Woodland HS-Softball Diamond [Directions] | W 7-1 | ||
| Fri., 4/21 | V Girls Tennis | Naugatuck | Home - Woodland HS-Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/24 | V Baseball | Seymour | Home - Woodland HS-Baseball Diamond [Directions] | W 5-4 | ||
| Mon., 4/24 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | 2:00 PM; 1 Bus | |
| Mon., 4/24 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | W 6-1 | 4:00 PM; 1 Bus | |
| Mon., 4/24 | V Girls Tennis | Seymour | Home - Woodland HS-Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/25 | V Boys Outdoor Track | Kennedy, WCA | Home - Woodland HS-Track [Directions] | WRHS 78, WCA 71 WRHS 118, Kennedy 31 | ||
| Tue., 4/25 | V Boys Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Tue., 4/25 | V Boys Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Tue., 4/25 | V Girls Outdoor Track | Kennedy, WCA | Home - Woodland HS-Track [Directions] | WRHS 111, WCA 39 WRHS 98, Kennedy 52 | ||
| Wed., 4/26 | V Baseball | Derby | Away - Payden Park [Directions] | W 15-2 | 4:00 PM; 1 Bus | |
| Wed., 4/26 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | 2:00 PM; 1 Bus | |
| Wed., 4/26 | V Softball | Derby | Home - Woodland HS-Softball Diamond [Directions] | W 25-0 | ||
| Wed., 4/26 | V Girls Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/26 | V Girls Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/27 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | 2:00 PM; 1 Bus | |
| Thu., 4/27 | V Boys Tennis | Torrington | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Fri., 4/28 | V Baseball | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | L 3-2 | 4:30 PM; 1 Bus | |
| Fri., 4/28 | V Softball | Holy Cross | Home - Woodland HS-Softball Diamond [Directions] | W 12-0 | ||
| Fri., 4/28 | V Girls Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | L 1-6 | ||
| Mon., 5/1 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | W 7-2 | 2:15 PM; 1 Bus | |
| Mon., 5/1 | V Boys Golf | Oxford, Seymour | Home - Oxford Greens [Directions] | 2:30 p.m. | ||
| Mon., 5/1 | V Softball | Oxford | Home - Woodland HS-Softball Diamond [Directions] | W 8-0 | ||
| Tue., 5/2 | V Boys Outdoor Track | Crosby, Wolcott | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | WRHS 134, Crosby 7 WRHS 132, Wolcott 8 | 2:15 PM | |
| Tue., 5/2 | V Girls Outdoor Track | Crosby, Wolcott | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | WRHS 134, Crosby 7 WRHS 122, Wolcott 19 | 2:15 PM | |
| Wed., 5/3 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | 2:00 PM; 1 Bus | |
| Wed., 5/3 | V Softball | WCA | Away - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | W 21-1 | 4:00 PM; 1 Bus | |
| Thu., 5/4 | V Baseball | WCA | Home - Woodland HS-Baseball Diamond [Directions] | W 15-0 (5) | ||
| Fri., 5/5 | V Baseball | Ansonia | Home - Woodland HS-Baseball Diamond [Directions] | W 12-2 (5) | ||
| Fri., 5/5 | V Softball | Ansonia | Away - Ansonia HS-Ansonia High School [Directions] | W 12-0 | 2:15 PM; 1 Bus | |
| Fri., 5/5 | V Girls Tennis | Ansonia | Home - Woodland HS-Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/8 | V Baseball | St. Paul Catholic | Home - Woodland HS-Baseball Diamond [Directions] | W 3-2 | ||
| Mon., 5/8 | V Boys Golf | St. Paul Catholic | Home - Oxford Greens [Directions] | 2:30 p.m. | ||
| Mon., 5/8 | V Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | W 28-4 | 2:15 PM; 1 Bus | |
| Mon., 5/8 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS-Tennis Courts [Directions] | W 6-1 | ||
| Tue., 5/9 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | 1:45 PM; 1 Bus | |
| Tue., 5/9 | V Boys Outdoor Track | Wilby, Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | WRHS 83, Seymour 67 WRHS 112, Wilby 36 | 2:15 PM | |
| Tue., 5/9 | V Boys Tennis | Wolcott | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Tue., 5/9 | V Girls Outdoor Track | Wilby, Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | WRHS 111, Seymour 38 WRHS 141, Wilby 8 | 2:15 PM | |
| Wed., 5/10 | V Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | W 11-1 (5) | 2:15 PM; 1 Bus | |
| Wed., 5/10 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | W 5-0 | 2:15 PM; 1 Bus | |
| Wed., 5/10 | V Softball | Kennedy | Home - Woodland HS-Softball Diamond [Directions] | W 19-0 | ||
| Wed., 5/10 | V Girls Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | W 7-0 | ||
| Wed., 5/10 | V Girls Tennis | Kennedy | Home - Woodland HS-Tennis Courts [Directions] | W 6-1 | ||
| Thu., 5/11 | V Baseball | Masuk | Home - Woodland HS-Baseball Diamond [Directions] | W 8-1 | ||
| Thu., 5/11 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | 1:45 PM | |
| Thu., 5/11 | V Boys Outdoor Track | Holy Cross, Watertown | Home - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Thu., 5/11 | V Girls Outdoor Track | Holy Cross, Watertown | Home - Woodland HS-Track [Directions] | Postponed | ||
| Thu., 5/11 | V Girls Tennis | Ansonia | Home - Woodland HS-Tennis Courts [Directions] | W 6-1 | ||
| Fri., 5/12 | V Softball | Seymour | Home - Woodland HS-Softball Diamond [Directions] | W 3-0 | ||
| Fri., 5/12 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | W 5-2 | 2:15 PM; 1 Bus | |
| Mon., 5/15 | V Baseball | Crosby | Home - Woodland HS-Baseball Diamond [Directions] | W 10-0 (5) | ||
| Mon., 5/15 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 2:30 p.m. | ||
| Mon., 5/15 | V Boys Outdoor Track | Oxford, St. Paul Catholic | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | 2:15 PM | |
| Mon., 5/15 | V Boys Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Mon., 5/15 | V Boys Tennis | Crosby | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Mon., 5/15 | V Girls Outdoor Track | Oxford, St. Paul Catholic | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | 2:15 PM | |
| Mon., 5/15 | V Softball | Crosby | Away - Crosby HS-CHS Softball Field #1 [Directions] | W 15-0 | 2:15 PM; 1 Bus | |
| Tue., 5/16 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | 2:30 p.m. | ||
| Tue., 5/16 | V Boys Tennis | Wilby | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Tue., 5/16 | V Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | W 3-2 | 2:15 PM; 1 Bus | |
| Tue., 5/16 | V Girls Tennis | St. Paul Catholic | Home - Woodland HS-Tennis Courts [Directions] | W 6-1 | ||
| Wed., 5/17 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | 2:30 p.m. | ||
| Wed., 5/17 | V Boys Tennis | Holy Cross | Home - Woodland HS-Tennis Courts [Directions] | W 5-0 | ||
| Wed., 5/17 | V Girls Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/19 | V Boys Tennis | Naugatuck | Home - Wilby HS [Directions] | W 4-1 | ||
| Sat., 5/20 | V Boys Outdoor Track | NVL Outdoor Track and Field Championship | Away - Naugatuck HS-Veterans Field | TBA | 7:30 AM | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/24, Time to 10:00 p.m. | ||||||
| Sat., 5/20 | V Girls Outdoor Track | NVL Outdoor Track and Field Championship | Away - Naugatuck HS-Veterans Field | TBA | 7:30 AM | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/24, Time to 10:00 a.m. | ||||||
| Mon., 5/22 | V Baseball | Oxford | Home - Woodland HS-Baseball Diamond [Directions] | W 4-3 | ||
| Mon., 5/22 | V Softball | St. Paul Catholic | Home - Woodland HS-Softball Diamond [Directions] | W 9-1 | ||
| Tue., 5/23 | V Baseball | Torrington | Home - Aces at Chase [Directions] | W 3-2 | ||
| Tue., 5/23 | V Softball | Holy Cross | Home - Wolcott HS-Turf Field and Lower Field [Directions] | W 16-0 | ||
| Thu., 5/25 | V Baseball | St. Paul Catholic | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 2:00 p.m. | ||
| Thu., 5/25 | V Softball | Oxford | Home - Wolcott HS-Wolcott Sports Complex [Directions] | 5:30 p.m. | ||
| Sat., 5/27 | V Boys Tennis | Killingly | Home - Woodland HS-Tennis Courts [Directions] | L 2-5 | ||
| Sat., 5/27 | V Girls Tennis | RHAM | Home - Woodland HS-Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 5/30 | V Baseball | Foran | Home - Woodland HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class M Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class M Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/30 | V Girls Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 1:00 p.m. | ||
| Wed., 5/31 | V Softball | Granby Memorial | Home - Woodland HS-Softball Diamond [Directions] | W 14-0 | ||
| Thu., 6/1 | V Boys Golf | NVL Boys' Golf Championship | Away - Watertown Golf Club | 7:30 a.m. | ||
| Fri., 6/2 | V Softball | Sheehan | Home - Woodland HS-Softball Diamond [Directions] | W 5-4 | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Golf | CIAC Division III Championship | Away - Stanley GC | 8:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Softball | Mercy | Home - Dunn Sports Complex [Directions] | W 8-3 | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Sat., 6/10 | V Boys Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/10 | V Softball | Sacred Heart Academy | Home - [CIAC] Burrill Family Field at UConn Softball Comp-[CIAC] Burrill Family Field at UConn [Directions] | W 16-0 | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||