| Wilby 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 338 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/23 | V Football | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Sat., 8/26 | V Football | Bristol Eastern, Prince Tech-Innovation, Wilbur Cross (Scrim.) | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 9:00 a.m. | ||
| Wed., 8/30 | V Football | Northwest United (Scrim.) | Away - Nonnewaug HS-Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 9/7 | V Football | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:30 p.m. | L 0-34 | |
| Sat., 9/9 | FM Football | Oxford | Home - Wilby HS-Football Field [Directions] | 11:00 a.m. | ||
| Sat., 9/9 | V Boys Soccer | Woodland | Home - Wilby HS-Pedro DeBrito Field [Directions] | 11:00 a.m. | L 0-8 | |
| Tue., 9/12 | V Boys Cross Country | Naugatuck, Crosby, Torrington | Away - Hop Brook Park [Directions] | 4:45 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Holy Cross | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 0-8 | |
| Tue., 9/12 | V Girls Cross Country | Naugatuck, Crosby, Torrington | Away - Hop Brook Park [Directions] | 4:45 p.m. | ||
| Tue., 9/12 | V Girls Volleyball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 9/12 | JV Girls Volleyball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 2:30 p.m. | L 0-8 | |
| Thu., 9/14 | V Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/14 | JV Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:45 p.m. | ||
| Fri., 9/15 | V Football | Watertown | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | L 6-41 | |
| Fri., 9/15 | V Girls Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 5:00 p.m. | ||
| Fri., 9/15 | V Girls Volleyball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 9/15 | JV Girls Volleyball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 9/16 | FM Football | Watertown | Home - Wilby HS-Football Field [Directions] | 11:00 a.m. | ||
| Tue., 9/19 | V Boys Cross Country | Holy Cross, Seymour, WCA | Away - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Holy Cross, Seymour, WCA | Away - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Girls Volleyball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:45 p.m. | L 1-3 | |
| Tue., 9/19 | JV Girls Volleyball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 9/20 | V Boys Soccer | Watertown | Away - Swift MS-Soccer Field [Directions] | 4:30 p.m. | L 0-4 | |
| Thu., 9/21 | V Girls Volleyball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | L 0-3 | |
| Thu., 9/21 | JV Girls Volleyball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/22 | V Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 7:00 p.m. | L 2-45 | |
| Fri., 9/22 | V Boys Soccer | Torrington | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 2-6 | |
| Fri., 9/22 | V Girls Swimming and Diving | Seymour | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 3:45 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:15 p.m. | L 1-3 | |
| Fri., 9/22 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:45 p.m. | ||
| Sat., 9/23 | JV Football | Derby | Home - Wilby HS [Directions] | 11:00 a.m. | ||
| Mon., 9/25 | V Girls Volleyball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 9/25 | JV Girls Volleyball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Boys Cross Country | Oxford, Kennedy, Watertown | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Ansonia | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 2-3 | |
| Tue., 9/26 | V Girls Cross Country | Oxford, Kennedy, Watertown | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Girls Swimming and Diving | Watertown | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 3:45 p.m. | ||
| Thu., 9/28 | V Football | Wolcott | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 14-35 | |
| Fri., 9/29 | V Boys Soccer | Seymour | Away - Seymour HS-turf field [Directions] | 6:00 p.m. | L 0-4 | |
| Fri., 9/29 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 5:00 p.m. | ||
| Sat., 9/30 | FM Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 11:00 a.m. | ||
| Tue., 10/3 | V Boys Cross Country | Derby, St. Paul Catholic | Away - Witek Park [Directions] | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Leo F. Ryan Athletic Complex-DeFilippo Field | ||||||
| Tue., 10/3 | V Girls Cross Country | Derby, St. Paul Catholic | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Girls Swimming and Diving | Torrington | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Volleyball | Derby | Away - Derby MS-DMS Gym [Directions] | 6:15 p.m. | L 0-3 | |
| Tue., 10/3 | JV Girls Volleyball | Derby | Away - Derby MS-DMS Gym [Directions] | 5:00 p.m. | ||
| Wed., 10/4 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:00 p.m. | L 1-6 | |
| Thu., 10/5 | V Football | St. Paul Catholic | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 0-22 | |
| Thu., 10/5 | V Girls Volleyball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Thu., 10/5 | JV Girls Volleyball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | V Boys Soccer | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 2:45 p.m. | L 1-5 | |
| Fri., 10/6 | V Girls Swimming and Diving | Oxford | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 6:00 p.m. | ||
| Fri., 10/6 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/6 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | ||
| Sat., 10/7 | FM Football | Northwest United | Home - Wilby HS-Football Field [Directions] | 11:00 a.m. | ||
| Tue., 10/10 | V Boys Cross Country | Woodland, Wolcott | Away - Woodland HS-Track [Directions] | 2:45 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 1-11 | |
| Tue., 10/10 | V Girls Cross Country | Woodland, Wolcott | Away - Woodland HS-Track [Directions] | 2:45 p.m. | ||
| Tue., 10/10 | V Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/10 | JV Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 4:45 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 1-3 | |
| Wed., 10/11 | JV Girls Volleyball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/12 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 10/13 | V Boys Soccer | Crosby | Home - Wilby HS-Wilby H.S. [Directions] | 2:30 p.m. | W 2-0 | |
| Fri., 10/13 | V Girls Swimming and Diving | Kennedy | Away - J F Kennedy HS Turf-John Reardon Pool [Directions] | 4:45 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 10/13 | JV Girls Volleyball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 10/16 | V Boys Soccer | Kaynor Tech | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | T 0-0 | |
| Tue., 10/17 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 4:30 p.m. | ||
| Wed., 10/18 | FM Football | Crosby | Home - Wilby HS-Football Field [Directions] | 4:45 p.m. | ||
| Wed., 10/18 | V Boys Soccer | Wolcott | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 1-5 | |
| Wed., 10/18 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/18 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/20 | V Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | L 2-3 | |
| Fri., 10/20 | JV Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 4:45 p.m. | ||
| Sat., 10/21 | V Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 10:00 a.m. | ||
| Mon., 10/23 | V Boys Soccer | Kennedy | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 0-5 | |
| Mon., 10/23 | V Girls Volleyball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 10/23 | JV Girls Volleyball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 10/25 | V Boys Soccer | Derby | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 2-0 | |
| Wed., 10/25 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/25 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 4:45 p.m. | ||
| Thu., 10/26 | V Girls Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:45 p.m. | L 0-3 | |
| Thu., 10/26 | JV Girls Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 10/27 | V Football | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | L 0-47 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/28 | FM Football | Holy Cross | Home - Wilby HS-Football Field [Directions] | Postponed | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class MM Championship | Away - Wickham Park | 12:55 p.m. | ||
| Thu., 11/2 | V Football | Kennedy | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 12-49 | |
| Fri., 11/3 | V Girls Swimming and Diving | St. Paul/Lewis Mills, Kennedy, Naugatuck, Oxford, Seymour, Watertown, Woodland | Away - John F. Kennedy HS-JFK Pool | 4:30 p.m. | ||
| Sat., 11/4 | JV Football | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 10:00 a.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Fri., 11/10 | V Football | Torrington | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | L 0-54 | |
| Sat., 11/11 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:00 a.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 11/20 | V Football | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 14-62 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Mon., 12/4 | V Boys Basketball | Pomperaug (Scrim.) | Away - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/4 | V Girls Basketball | Maloney (Scrim.) | Away - Maloney HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 12/5 | V Girls Basketball | Maloney (Scrim.) | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | Cancelled | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Mon., 12/11 | V Boys Basketball | Maloney (Scrim.) | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 12/12 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | L 23-54 | |
| Tue., 12/12 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/15 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 7:00 p.m. | W 64-62 | |
| Fri., 12/15 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS (Waterbury) [Directions] | 6:30 p.m. | ||
| Fri., 12/15 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:00 p.m. | L 19-40 | |
| Mon., 12/18 | V Boys Basketball | Seymour | Away - Seymour MS-Gymnasium [Directions] | 7:00 p.m. | W 60-52 | |
| Mon., 12/18 | JV Boys Basketball | Seymour | Away - Seymour MS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/18 | V Girls Basketball | Platt | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 37-31 | |
| Mon., 12/18 | JV Girls Basketball | Platt | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/19 | V Girls Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 49-55 | |
| Tue., 12/19 | JV Girls Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | FR Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 12/22 | V Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 97-53 | |
| Fri., 12/22 | JV Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 49-62 | |
| Fri., 12/22 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/27 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 1:00 p.m. | W 84-51 | |
| Wed., 12/27 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 11:30 a.m. | ||
| Fri., 12/29 | V Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 1:30 p.m. | W 108-63 | |
| Fri., 12/29 | JV Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 12:00 p.m. | ||
| Fri., 12/29 | FR Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Fri., 12/29 | V Girls Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 12:30 p.m. | L 41-43 | |
| Fri., 12/29 | JV Girls Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 1/2 | FR Boys Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 1/3 | V Boys Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 95-61 | |
| Wed., 1/3 | JV Boys Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Watertown | Away - Watertown HS [Directions] | 6:00 p.m. | L 31-54 | |
| Wed., 1/3 | JV Girls Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/5 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 67-71 | |
| Fri., 1/5 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Woodland, Amity | Away - Woodland HS-pool [Directions] | 5:00 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 43-48 | |
| Fri., 1/5 | JV Girls Basketball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/6 | FR Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 11:00 a.m. | ||
| Mon., 1/8 | FR Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 1/10 | V Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 65-74 | |
| Wed., 1/10 | JV Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 1/11 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 32-54 | |
| Thu., 1/11 | JV Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | V Boys Swimming and Diving | Torrington | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Postponed | ||
| Mon., 1/15 | V Boys Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 2:00 p.m. | W 92-40 | |
| Mon., 1/15 | JV Boys Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 12:30 p.m. | ||
| Mon., 1/15 | FR Boys Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 11:00 a.m. | ||
| Wed., 1/17 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Canceled | Cancelled | |
| Thu., 1/18 | V Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 65-68 | |
| Thu., 1/18 | JV Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | Canceled | Cancelled | |
| Fri., 1/19 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | W 50-38 | |
| Fri., 1/19 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Canceled | Cancelled | |
| Mon., 1/22 | V Girls Basketball | Derby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | W 45-35 | |
| Wed., 1/24 | V Boys Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 70-55 | |
| Wed., 1/24 | JV Boys Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/24 | FR Boys Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 1/25 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | W 62-58 | |
| Thu., 1/25 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Boys Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Seymour | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Girls Basketball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 44-69 | |
| Fri., 1/26 | JV Girls Basketball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Girls Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Mon., 1/29 | FR Boys Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 1/29 | FR Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 1/29 | V Girls Basketball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | L 44-56 | |
| Mon., 1/29 | JV Girls Basketball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Boys Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 101-51 | |
| Tue., 1/30 | JV Boys Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Oxford, Crosby/WCA, Torrington | Away - Oxford HS-Pool [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:30 p.m. | L 51-71 | |
| Tue., 1/30 | JV Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/31 | V Girls Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 23-38 | |
| Wed., 1/31 | JV Girls Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | L 71-87 | |
| Fri., 2/2 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 2/2 | V Girls Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 36-35 | |
| Fri., 2/2 | JV Girls Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/3 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 11:00 a.m. | ||
| Mon., 2/5 | V Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 7:00 p.m. | W 82-70 | |
| Mon., 2/5 | JV Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/5 | FR Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | Canceled | Cancelled | |
| Mon., 2/5 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 26-54 | |
| Mon., 2/5 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 33-60 | |
| Tue., 2/6 | JV Girls Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/7 | V Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 70-50 | |
| Wed., 2/7 | JV Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Fri., 2/9 | V Boys Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 71-58 | |
| Fri., 2/9 | JV Boys Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/12 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:30 p.m. | W 67-42 | |
| Wed., 2/14 | V Girls Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | W 51-23 | |
| Wed., 2/14 | JV Girls Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Thu., 2/15 | V Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 6:00 p.m. | W 85-45 | |
| Thu., 2/15 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 2/15 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 2/15 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/16 | V Boys Swimming and Diving | Kennedy | Away - J F Kennedy HS Turf-John Reardon Pool [Directions] | 4:45 p.m. | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Derby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | W 113-29 | |
| Mon., 2/19 | JV Boys Basketball | Derby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 2/20 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 2:00 p.m. | W 106-61 | |
| Tue., 2/20 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 12:30 p.m. | ||
| Fri., 2/23 | V Boys Swimming and Diving | Crosby/WCA | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Sat., 2/24 | V Boys Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 2:30 p.m. | W 61-46 | |
| Mon., 2/26 | V Boys Basketball | WCA | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:30 p.m. | L 57-63 | |
| Tue., 2/27 | V Boys Swimming and Diving | TBA, Crosby/WCA, Holy Cross, Kennedy, TBA, Oxford, Seymour, Torrington, Watertown | Away - Watertown HS-Frank M. Reinhold Pool | 6:00 p.m. | ||
| Tue., 2/27 | V Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:30 p.m. | L 39-60 | |
| Fri., 3/1 | V Boys Basketball | Guilford (Scrim.) | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:15 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | Woodland, Crosby/WCA, Holy Cross, Kennedy, Naugatuck, Oxford, Seymour, Torrington, Watertown | Away - John F. Kennedy HS-JFK Pool | 4:00 p.m. | ||
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class L Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Thu., 3/7 | V Boys Basketball | Fairfield Ludlowe | Home - Wilby HS-Gym [Directions] | 6:30 p.m. | L 42-44 | |
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 11:15 a.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Thu., 3/28 | JV Baseball | Nonnewaug (Scrim.) | Home - Wilby HS-Wilby H.S. [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Sat., 3/30 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 11:00 a.m. | L 0-14 | |
| Sat., 3/30 | V Girls Tennis | Naugatuck | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 11:00 a.m. | L 0-7 | |
| Mon., 4/1 | V Baseball | Kennedy | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 7-20 | |
| Mon., 4/1 | V Softball | Kennedy | Away - Kennedy HS-Softball Field [Directions] | 3:45 p.m. | L 9-21 | |
| Mon., 4/1 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/4 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | 5:30 p.m. | L 3-19 | |
| Fri., 4/5 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Fri., 4/5 | V Boys Tennis | Naugatuck | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/5 | V Girls Tennis | Wolcott | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/6 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 12:30 p.m. | L 4-8 | |
| Sat., 4/6 | JV Baseball | WCA | Home - Wilby HS-Wilby H.S. [Directions] | Postponed | ||
| Mon., 4/8 | V Baseball | Woodland | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 2-18 | |
| Mon., 4/8 | V Boys Tennis | Woodland | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 4/8 | V Boys Tennis | Woodland | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:15 p.m. | L 0-5 | |
| Mon., 4/8 | V Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-22 | |
| Mon., 4/8 | V Girls Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | L 0-7 | |
| Tue., 4/9 | V Boys Golf | Holy Cross, Seymour | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Holy Cross | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 2:45 p.m. | L 0-5 | |
| Tue., 4/9 | V Boys Tennis | Holy Cross | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 4/9 | JV Boys Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 4/10 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 3:00 p.m. | L 0-10 | |
| Wed., 4/10 | V Boys Golf | Wolcott | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 4/10 | V Softball | St. Paul Catholic | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 11:00 a.m. | L 0-17 | |
| Thu., 4/11 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:45 p.m. | ||
| Thu., 4/11 | JV Boys Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:00 p.m. | ||
| Mon., 4/15 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 3:00 p.m. | L 0-10 | |
| Mon., 4/15 | V Softball | Ansonia | Home - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 3:45 p.m. | L 21-25 | |
| Tue., 4/16 | V Baseball | Oxford | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 3:30 p.m. | L 2-16 | |
| Tue., 4/16 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 11:00 a.m. | L 0-22 | |
| Wed., 4/17 | V Baseball | Watertown | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 4/17 | V Softball | Watertown | Away - Watertown High-Softball Field [Directions] | 3:45 p.m. | L 0-19 | |
| Fri., 4/19 | V Softball | Crosby | Away - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 3:00 p.m. | L 6-24 | |
| Mon., 4/22 | V Baseball | Torrington | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 3:30 p.m. | L 3-18 | |
| Mon., 4/22 | V Boys Golf | Torrington | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 4/22 | V Boys Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | L 0-5 | |
| Mon., 4/22 | V Boys Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:45 p.m. | ||
| Mon., 4/22 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 4:00 p.m. | L 2-20 | |
| Mon., 4/22 | V Girls Tennis | Torrington | Away - Durand St Park [Directions] | 3:30 p.m. | L 0-7 | |
| Tue., 4/23 | JV Baseball | WCA | Home - Wilby HS-Wilby H.S. [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | V Boys Golf | Oxford, Holy Cross | Away - Oxford HS-Oxford Greens [Directions] | 2:45 p.m. | ||
| Tue., 4/23 | JV Boys Volleyball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/24 | V Baseball | Kennedy | Away - Waterville Park-Baseball Field [Directions] | 3:30 p.m. | L 6-7 | |
| Wed., 4/24 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 4/24 | V Softball | Kennedy | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | W 18-17 | |
| Wed., 4/24 | V Girls Tennis | Ansonia | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:00 p.m. | L 0-7 | |
| Wed., 4/24 | V Girls Tennis | Ansonia | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | L 0-7 | |
| Thu., 4/25 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:00 p.m. | ||
| Thu., 4/25 | V Boys Outdoor Track | Crosby, WCA | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Kennedy | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 12:30 p.m. | L 0-5 | |
| Thu., 4/25 | V Boys Tennis | Kennedy | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 1:30 p.m. | L 0-5 | |
| Thu., 4/25 | V Girls Outdoor Track | Crosby, WCA | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Fri., 4/26 | V Baseball | WCA | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | W 8-4 | |
| Fri., 4/26 | V Softball | WCA | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 0-16 | |
| Sat., 4/27 | JV Baseball | Crosby | Home - Wilby HS-Wilby H.S. [Directions] | 12:00 p.m. | ||
| Mon., 4/29 | V Baseball | Derby | Away - Payden Park [Directions] | 5:30 p.m. | L 0-14 | |
| Mon., 4/29 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 2:30 p.m. | ||
| Mon., 4/29 | V Boys Outdoor Track | Crosby, St. Paul Catholic | Away - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Crosby, St. Paul Catholic | Away - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Softball | Wolcott | Home - Bucks Hill Park #2-Buck Hill Park #2 [Directions] | 3:45 p.m. | L 0-27 | |
| Mon., 4/29 | V Girls Tennis | Kennedy | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | L 0-7 | |
| Tue., 4/30 | V Boys Golf | St. Paul Catholic | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 2:30 p.m. | L 0-5 | |
| Tue., 4/30 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 4:00 p.m. | L 0-5 | |
| Tue., 4/30 | JV Boys Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:00 p.m. | ||
| Tue., 4/30 | V Softball | Nonnewaug | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 0-24 | |
| Wed., 5/1 | V Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 1-11 | |
| Wed., 5/1 | V Boys Tennis | Watertown | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 5/1 | V Boys Tennis | Watertown | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:30 p.m. | L 0-5 | |
| Thu., 5/2 | V Boys Golf | Woodland | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Thu., 5/2 | JV Boys Volleyball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 5/2 | V Softball | Naugatuck | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Holy Cross | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 2:30 p.m. | ||
| Thu., 5/2 | V Girls Tennis | St. Paul Catholic | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | V Baseball | Thomaston | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | ||
| Fri., 5/3 | V Girls Tennis | Seymour | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | ||
| Sat., 5/4 | JV Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 10:30 a.m. | ||
| Mon., 5/6 | V Baseball | Crosby | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 7:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Crosby | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | ||
| Mon., 5/6 | V Softball | Holy Cross | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Boys Golf | Oxford | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Watertown | Away - Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | JV Boys Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Softball | Crosby | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Baseball | WCA | Away - Municipal Stadium-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 7:00 p.m. | ||
| Wed., 5/8 | V Softball | Ansonia | Away - Ansonia HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | ||
| Thu., 5/9 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | 2:30 p.m. | ||
| Fri., 5/10 | V Baseball | Seymour | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 3:30 p.m. | ||
| Sat., 5/11 | V Boys Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | Torrington Varsity Alumni Club Invitational | Away - Torrington HS | 10:00 a.m. | ||
| Mon., 5/13 | V Baseball | Crosby | Away - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 7:00 p.m. | ||
| Mon., 5/13 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Softball | Derby | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Crosby | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | ||
| Tue., 5/14 | V Boys Golf | Naugatuck | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 5/15 | V Boys Golf | Watertown | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 5/15 | V Softball | Kaynor Tech | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Baseball | Kaynor Tech | Away - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 3:45 p.m. | ||
| Mon., 5/20 | V Baseball | Derby | Home - Wilby HS-Wilby H.S. [Directions] | 3:30 p.m. | ||
| Mon., 5/20 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | ||