| Wilby 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 333 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Fri., 9/3 | V Football | Stamford (Scrim.) | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Sat., 9/4 | V Football | Crosby (Scrim.) | Home - Municipal Stadium-Bethel HS Track & Field Training Center [Directions] | Canceled | Cancelled | |
| Thu., 9/9 | V Football | Ansonia | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:00 p.m. | L 6-48 | |
| Sat., 9/11 | V Boys Soccer | Derby | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 11:00 a.m. | W 5-3 | |
| Tue., 9/14 | V Boys Cross Country | Watertown, Torrington, WCA | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Watertown, Torrington, WCA | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 6:15 p.m. | L 0-3 | |
| Tue., 9/14 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 9/17 | V Football | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 7:00 p.m. | L 6-56 | |
| Fri., 9/17 | V Boys Soccer | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 5:00 p.m. | L 0-7 | |
| Fri., 9/17 | V Girls Swimming and Diving | Woodland | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 4:00 p.m. | ||
| Fri., 9/17 | V Girls Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | L 0-3 | |
| Fri., 9/17 | JV Girls Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 9/18 | FM Football | Seymour | Home - Wilby HS-Football Field [Directions] | 10:00 a.m. | ||
| Mon., 9/20 | V Boys Soccer | Torrington | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 1-5 | |
| Mon., 9/20 | V Girls Volleyball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 9/20 | JV Girls Volleyball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:45 p.m. | ||
| Tue., 9/21 | V Boys Cross Country | Crosby, Oxford | Away - Bucks Hill (MONTOE) Park-Soccer Pitch [Directions] | Postponed | ||
| Tue., 9/21 | V Girls Cross Country | Crosby, Oxford | Away - Bucks Hill (MONTOE) Park-Soccer Pitch [Directions] | Postponed | ||
| Tue., 9/21 | V Girls Volleyball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/21 | JV Girls Volleyball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 9/22 | V Girls Swimming and Diving | Torrington | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | V Football | Watertown | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:00 p.m. | L 6-24 | |
| Thu., 9/23 | JV Boys Soccer | Oxford | Home - Wilby HS-Pedro DeBrito Field [Directions] | 6:00 p.m. | ||
| Fri., 9/24 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/24 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 9/25 | FM Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Tue., 9/28 | V Boys Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-6 | |
| Tue., 9/28 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 5:00 p.m. | ||
| Tue., 9/28 | V Girls Volleyball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 9/28 | JV Girls Volleyball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 9/29 | V Boys Cross Country | Holy Cross, Naugatuck, Woodland | Away - Holy Cross [Directions] | 3:45 p.m. | ||
| Wed., 9/29 | V Girls Cross Country | Holy Cross, Naugatuck, Woodland | Away - Holy Cross [Directions] | 3:45 p.m. | ||
| Thu., 9/30 | JV Boys Soccer | Wolcott | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | ||
| Thu., 9/30 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 5:00 p.m. | ||
| Thu., 9/30 | 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., 9/30 | JV Girls Volleyball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/1 | V Football | WCA | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 7:00 p.m. | L 0-38 | |
| Fri., 10/1 | V Boys Soccer | Wolcott | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 2-6 | |
| Fri., 10/1 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/1 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 10/2 | FM Football | Naugatuck | Home - Wilby HS-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | V Girls Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 11:00 a.m. | L 0-3 | |
| Tue., 10/5 | V Boys Cross Country | Derby, St. Paul Catholic, Wolcott | Away - Witek Park [Directions] | 5:15 p.m. | ||
| Tue., 10/5 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Ave [Directions] | 4:45 p.m. | W 3-0 | |
| Tue., 10/5 | V Girls Cross Country | Derby, St. Paul Catholic, Wolcott | Away - Witek Park [Directions] | 5:15 p.m. | ||
| Tue., 10/5 | V Girls Swimming and Diving | Seymour | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:30 p.m. | L 0-3 | |
| Tue., 10/5 | JV Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:00 p.m. | ||
| Wed., 10/6 | V Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | L 0-7 | |
| Wed., 10/6 | V Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:30 p.m. | L 1-3 | |
| Wed., 10/6 | JV Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 10/8 | V Football | St. Paul Catholic | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 7:00 p.m. | L 30-32 | |
| Fri., 10/8 | V Boys Soccer | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 2:45 p.m. | L 0-5 | |
| Fri., 10/8 | V Girls Swimming and Diving | Oxford | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 6:00 p.m. | ||
| Fri., 10/8 | V Girls Volleyball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 10/8 | JV Girls Volleyball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | ||
| Sat., 10/9 | FM Football | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 10:00 a.m. | ||
| Tue., 10/12 | V Boys Cross Country | Seymour, Kennedy | Away - Seymour HS-Seymour High Lower Field [Directions] | Canceled | Cancelled | |
| Tue., 10/12 | V Boys Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 5:00 p.m. | L 1-6 | |
| Tue., 10/12 | V Girls Cross Country | Seymour, Kennedy | Away - Seymour HS-Seymour High Lower Field [Directions] | Canceled | Cancelled | |
| Tue., 10/12 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/12 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | ||
| Wed., 10/13 | FM Football | Kennedy | Home - Wilby HS-Football Field [Directions] | 5:00 p.m. | ||
| Thu., 10/14 | V Boys Soccer | Kaynor Tech | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 0-2 | |
| Fri., 10/15 | V Football | Kennedy | Away - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 7:00 p.m. | W 24-18 | |
| Fri., 10/15 | V Boys Soccer | St. Paul Catholic | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:45 p.m. | L 0-4 | |
| Fri., 10/15 | V Girls Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 5:15 p.m. | ||
| Fri., 10/15 | V Girls Volleyball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:15 p.m. | W 3-0 | |
| Fri., 10/15 | JV Girls Volleyball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Mon., 10/18 | V Boys Soccer | WCA | Home - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 2:45 p.m. | L 2-5 | |
| Tue., 10/19 | V Girls Swimming and Diving | Kennedy | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 5:00 p.m. | ||
| Tue., 10/19 | V Girls Volleyball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | L 0-3 | |
| Tue., 10/19 | JV Girls Volleyball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 10/20 | V Boys Soccer | Oxford | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 0-6 | |
| Thu., 10/21 | V Football | Holy Cross | Away - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:30 p.m. | L 12-46 | |
| Thu., 10/21 | V Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 5:30 p.m. | L 0-4 | |
| Thu., 10/21 | V Girls Volleyball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Thu., 10/21 | JV Girls Volleyball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 10/22 | FM Football | Holy Cross | Home - Wilby HS-Football Field [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 10/22 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/22 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Mon., 10/25 | V Boys Soccer | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/25 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:15 p.m. | L 0-3 | |
| Mon., 10/25 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 10/27 | V Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:30 p.m. | L 2-3 | |
| Wed., 10/27 | JV Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:15 p.m. | ||
| Thu., 10/28 | V Boys Soccer | Kennedy | Home - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 4-3 | |
| Thu., 10/28 | V Girls Volleyball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:45 p.m. | L 0-3 | |
| Thu., 10/28 | JV Girls Volleyball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class L Championship | Away - Wickham Park | 11:25 a.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class MM Championship | Away - Wickham Park | 10:50 a.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 28-31 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | FM Football | Oxford | Home - Wilby HS-Football Field [Directions] | 10:00 a.m. | ||
| Wed., 11/10 | FM Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 5:30 p.m. | ||
| Thu., 11/11 | V Football | Crosby | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:00 p.m. | L 28-62 | |
| Thu., 11/11 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - East Hartford | 11:30 a.m. | ||
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class LL Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Tue., 11/23 | V Football | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 0-52 | |
| Tue., 12/7 | V Boys Basketball | Pomperaug (Scrim.) | Away - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 12/10 | V Boys Basketball | Brookfield (Scrim.) | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/13 | V Girls Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 13-56 | |
| Mon., 12/13 | JV Girls Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/14 | V Boys Basketball | Harding (Scrim.) | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 12/16 | V Boys Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 81-56 | |
| Thu., 12/16 | JV Boys Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | FR Boys Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 12/16 | V Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:45 p.m. | L 14-60 | |
| Thu., 12/16 | JV Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 12/21 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | W 54-51 | |
| Tue., 12/21 | JV Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 12/21 | V Girls Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 10-50 | |
| Tue., 12/21 | JV Girls Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 12/27 | FR Boys Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Mon., 12/27 | V Girls Basketball | Maloney | Away - Maloney HS-Gym [Directions] | 1:30 p.m. | L 22-64 | |
| Mon., 12/27 | JV Girls Basketball | Maloney | Away - Maloney HS-Gym [Directions] | 12:00 p.m. | ||
| Tue., 12/28 | V Boys Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 66-49 | |
| Tue., 12/28 | JV Boys Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 12/30 | V Boys Basketball | Derby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 85-65 | |
| Thu., 12/30 | JV Boys Basketball | Derby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 1/3 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 65-88 | |
| Mon., 1/3 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/5 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Thu., 1/6 | FR Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Sat., 1/8 | V Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 12:00 p.m. | L 37-81 | |
| Sat., 1/8 | JV Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Sat., 1/8 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 11:30 a.m. | L 15-45 | |
| Sat., 1/8 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 10:00 a.m. | ||
| Mon., 1/10 | FR Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 1/11 | JV Girls Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Thu., 1/13 | FR Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 1/13 | V Girls Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | L 16-52 | |
| Thu., 1/13 | JV Girls Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/14 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | L 19-56 | |
| Fri., 1/14 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 1/15 | V Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 12:00 p.m. | L 62-78 | |
| Sat., 1/15 | JV Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 10:30 a.m. | ||
| Tue., 1/18 | V Girls Basketball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 24-53 | |
| Tue., 1/18 | JV Girls Basketball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | FR Boys Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:30 p.m. | L 13-52 | |
| Fri., 1/21 | JV Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 1/22 | V Boys Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 12:00 p.m. | L 54-70 | |
| Sat., 1/22 | JV Boys Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 1/24 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 43-81 | |
| Mon., 1/24 | JV Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/25 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 7:00 p.m. | L 69-75 | |
| Tue., 1/25 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | L 12-42 | |
| Tue., 1/25 | JV Girls Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 1/27 | V Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 54-84 | |
| Thu., 1/27 | JV Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 1/28 | FR Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Mon., 1/31 | V Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 6:45 p.m. | W 74-55 | |
| Mon., 1/31 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/31 | FR Boys Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Mon., 1/31 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | W 33-27(OT) | |
| Mon., 1/31 | JV Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | Canceled | Cancelled | |
| Tue., 2/1 | V Boys Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 68-73 | |
| Tue., 2/1 | JV Boys Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 15-54 | |
| Tue., 2/1 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/3 | V Boys Basketball | Nonnewaug | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 57-53 | |
| Thu., 2/3 | JV Boys Basketball | Nonnewaug | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:30 p.m. | L 18-72 | |
| Thu., 2/3 | JV Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 2/7 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | L 70-82 | |
| Mon., 2/7 | JV Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:30 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | W 38-33 | |
| Mon., 2/7 | JV Girls Basketball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 42-62 | |
| Tue., 2/8 | JV Girls Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/9 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:30 p.m. | L 69-95 | |
| Wed., 2/9 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 2/10 | V Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 39-78 | |
| Thu., 2/10 | JV Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/10 | FR Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Fri., 2/11 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:00 p.m. | L 26-48 | |
| Fri., 2/11 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 2/14 | V Girls Basketball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 25-76 | |
| Mon., 2/14 | JV Girls Basketball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Tue., 2/15 | V Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 49-80 | |
| Tue., 2/15 | JV Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | V Girls Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 20-66 | |
| Tue., 2/15 | JV Girls Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 2/17 | V Girls Basketball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 15-55 | |
| Thu., 2/17 | JV Girls Basketball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 2/18 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 41-69 | |
| Fri., 2/18 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | Postponed | ||
| Fri., 2/18 | V Girls Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | L 13-44 | |
| Tue., 2/22 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:00 p.m. | L 69-89 | |
| Tue., 2/22 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 4:15 p.m. | ||
| Wed., 2/23 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:30 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 5:30 p.m. | ||
| Mon., 3/14 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class LL Swimming Championships | Away - Cornerstone Pool | 1:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Wed., 3/23 | JV Baseball | Nonnewaug (Scrim.) | Home - Wilby HS-Wilby H.S. [Directions] | 3:30 p.m. | ||
| Sat., 4/2 | V Boys Outdoor Track | Oxford, Holy Cross | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 11:00 a.m. | ||
| Sat., 4/2 | V Boys Tennis | Crosby | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 12:00 p.m. | Cancelled | |
| Sat., 4/2 | V Girls Outdoor Track | Oxford, Holy Cross | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 11:00 a.m. | ||
| Sat., 4/2 | V Softball | Crosby | Home - Municipal Stadium Complex-Joan Joyce Diamond [Directions] | 9:30 a.m. | W 24-12 | |
| Sat., 4/2 | V Girls Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 10:00 a.m. | L 0-7 | |
| Mon., 4/4 | V Baseball | Kennedy | Home - Wilby HS-Wilby H.S. [Directions] | 2:45 p.m. | L 5-19 | |
| Mon., 4/4 | V Softball | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 5:15 p.m. | L 3-5 | |
| Mon., 4/4 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 5:15 p.m. | L 0-7 | |
| Wed., 4/6 | V Baseball | Torrington | Home - Wilby HS-Wilby H.S. [Directions] | Canceled | Cancelled | |
| Wed., 4/6 | V Girls Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/8 | V Baseball | WCA | Away - Municipal Stadium-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 5:00 p.m. | L 8-18 | |
| Fri., 4/8 | V Softball | WCA | Home - Huntington Park #1 [Directions] | 5:00 p.m. | L 9-25 | |
| Fri., 4/8 | V Girls Tennis | St. Paul Catholic | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:30 p.m. | L 0-7 | |
| Mon., 4/11 | V Baseball | Woodland | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 0-24 | |
| Mon., 4/11 | V Boys Golf | Torrington | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Laniah Moffet 48 Aoife Devaney 48 Aidan Devaney 44 | |
| Mon., 4/11 | V Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | 5:00 p.m. | L 0-21 | |
| Mon., 4/11 | V Girls Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | L 0-7 | |
| Tue., 4/12 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 5:30 p.m. | L 2-20 | |
| Tue., 4/12 | V Boys Outdoor Track | Watertown, St. Paul Catholic | Away - Watertown HS [Directions] | 4:45 p.m. | ||
| Tue., 4/12 | V Boys Tennis | Woodland | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 4/12 | V Girls Outdoor Track | Watertown, St. Paul Catholic | Away - Watertown HS [Directions] | 4:45 p.m. | ||
| Wed., 4/13 | V Boys Golf | St. Paul Catholic | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Laniah Moffet 40 Aoife Devaney 46 Aidan Devaney 40 | |
| Wed., 4/13 | V Softball | Wolcott | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 0-19 | |
| Thu., 4/14 | V Baseball | Hillhouse/Career | Home - Wilby HS-Wilby H.S. [Directions] | 3:00 p.m. | L 2-15 | |
| Fri., 4/15 | V Baseball | Crosby | Away - Washington Park Waterbury-Baseball FIeld [Directions] | 11:00 a.m. | L 2-12 | |
| Fri., 4/15 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 11:00 a.m. | Laniah Moffet 39 Aidan Devaney 42 Aoife Devaney 44 Branden Halle 68 | |
| Mon., 4/18 | V Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 0-28 | |
| Mon., 4/18 | V Boys Golf | Watertown | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 11:00 a.m. | Laniah Moffet 47 Aidan Devaney 44 Aoife Devaney 48 Branden Halle 68 | |
| Mon., 4/18 | V Softball | Holy Cross | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 3-22 | |
| Wed., 4/20 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 11:00 a.m. | L 1-13 | |
| Wed., 4/20 | V Boys Outdoor Track | Derby, WCA | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Girls Outdoor Track | Derby, WCA | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:45 p.m. | ||
| Thu., 4/21 | JV Baseball | WCA | Home - Wilby HS-Wilby H.S. [Directions] | 11:00 a.m. | ||
| Thu., 4/21 | V Girls Tennis | Wolcott | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 11:00 a.m. | L 0-7 | |
| Fri., 4/22 | V Baseball | Crosby | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:00 p.m. | W 8-6 | |
| Fri., 4/22 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | Cancelled | |
| Fri., 4/22 | V Softball | Crosby | Away - Municipal Stadium Complex-Joan Joyce Diamond [Directions] | 3:30 p.m. | W 13-12 | |
| Fri., 4/22 | V Girls Tennis | Crosby | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 11:00 a.m. | W 4-1 | |
| Mon., 4/25 | V Baseball | Watertown | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 2-21 | |
| Mon., 4/25 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | 2:30 p.m. | Laniah Moffet 41 Aidan Devaney 46 Aoife Devaney 46 Branden Halle 72 | |
| Mon., 4/25 | V Boys Tennis | Watertown | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 4/25 | V Softball | Watertown | Away - Watertown High-Softball Field [Directions] | 5:00 p.m. | L 0-19 | |
| Mon., 4/25 | V Girls Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 5:00 p.m. | L 0-7 | |
| Tue., 4/26 | V Boys Outdoor Track | Wolcott | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 3:30 p.m. | ||
| Tue., 4/26 | V Girls Outdoor Track | Wolcott | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | Laniah Moffet 44 Aidan Devaney 49 Aoife Devaney 43 Branden Halle 69 | |
| Wed., 4/27 | V Boys Tennis | Naugatuck | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | L 0-5 | |
| Wed., 4/27 | V Boys Tennis | Naugatuck | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:00 p.m. | L 0-5 | |
| Wed., 4/27 | V Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | 5:15 p.m. | L 2-18 | |
| Wed., 4/27 | V Girls Tennis | St. Paul Catholic | Away - Page Park -Tennis Courts [Directions] | 4:45 p.m. | L 0-7 | |
| Thu., 4/28 | V Baseball | St. Paul Catholic | Home - Municipal Stadium Complex-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 5:30 p.m. | L 1-24 | |
| Thu., 4/28 | V Boys Golf | Woodland | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Aoife Devaney 44 Laniah Moffet 43 Aidan Devaney 44 Branden Halle 70 | |
| Fri., 4/29 | V Baseball | Derby | Away - Payden Park [Directions] | 5:30 p.m. | L 3-6 | |
| Fri., 4/29 | V Boys Tennis | Wolcott | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/29 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 4:45 p.m. | L 0-5 | |
| Fri., 4/29 | V Softball | Derby | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 9-21 | |
| Tue., 5/3 | V Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | 5:00 p.m. | L 7-9 | |
| Tue., 5/3 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 2:45 p.m. | Laniah Moffet 39 Aoife Devaney 42 Aidan Devaney 42 Branden Halle 66 | |
| Tue., 5/3 | V Boys Outdoor Track | Naugatuck, Torrington | Away - Naugatuck HS-Veterans Field [Directions] | 5:00 p.m. | ||
| Tue., 5/3 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 5:00 p.m. | L 0-5 | |
| Tue., 5/3 | V Girls Outdoor Track | Naugatuck, Torrington | Away - Naugatuck HS-Veterans Field [Directions] | 5:00 p.m. | ||
| Tue., 5/3 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 5:30 p.m. | L 3-20 | |
| Tue., 5/3 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 5:00 p.m. | L 0-7 | |
| Thu., 5/5 | V Baseball | Naugatuck | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 0-15 | |
| Thu., 5/5 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 6:00 p.m. | L 0-12 | |
| Mon., 5/9 | JV Baseball | Wamogo | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Mon., 5/9 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | Laniah Moffet 49 Aoife Devaney 50 Aidan Devaney 52 Branden Halle 71 | |
| Mon., 5/9 | V Boys Tennis | Holy Cross | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 5/9 | V Boys Tennis | Holy Cross | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:30 p.m. | L 1-4 | |
| Mon., 5/9 | V Softball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 1-19 | |
| Mon., 5/9 | V Girls Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 0-7 | |
| Tue., 5/10 | V Boys Outdoor Track | Woodland, Seymour | Away - Woodland HS-Track [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 5:00 p.m. | L 0-5 | |
| Tue., 5/10 | V Girls Outdoor Track | Woodland, Seymour | Away - Woodland HS-Track [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Softball | Kennedy | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:30 p.m. | L 10-14 | |
| Wed., 5/11 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 5:15 p.m. | L 4-10 | |
| Wed., 5/11 | V Boys Golf | Holy Cross | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Laniah Moffet 40 Aoife Devaney 41 Aidan Devaney 40 Stephanie Cruz 72 | |
| Wed., 5/11 | V Softball | Oxford | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 5:30 p.m. | L 0-21 | |
| Wed., 5/11 | V Girls Tennis | Watertown | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/12 | V Baseball | Holy Cross | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 1-18 | |
| Thu., 5/12 | V Boys Tennis | Kennedy | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:00 p.m. | L 0-5 | |
| Thu., 5/12 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 5:00 p.m. | L 0-7 | |
| Fri., 5/13 | V Boys Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 5/13 | V Boys Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:45 p.m. | L 0-5 | |
| Fri., 5/13 | V Softball | WCA | Away - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | 5:00 p.m. | L 0-13 | |
| Mon., 5/16 | V Boys Golf | Seymour | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Laniah Moffet 42 Aoife Devaney 45 Aidan Devaney 48 | |
| Mon., 5/16 | V Boys Tennis | Watertown | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 2:00 p.m. | L 0-5 | |
| Mon., 5/16 | V Girls Tennis | Ansonia | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/17 | V Baseball | Kaynor Tech | Away - Kaynor Technical School-Municipal Stadium [Directions] | 5:00 p.m. | L 2-14 | |
| Tue., 5/17 | V Boys Outdoor Track | Crosby, Kennedy | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 2:30 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 2:30 p.m. | W 5-0 | |
| Tue., 5/17 | V Girls Outdoor Track | Crosby, Kennedy | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 2:30 p.m. | ||
| Tue., 5/17 | V Softball | Kaynor Tech | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 3-16 | |
| Wed., 5/18 | V Baseball | WCA | Home - Municipal Stadium Complex-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | L 15-16 | |
| Wed., 5/18 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:00 p.m. | Laniah Moffet 44 Aoife Devaney 43 Aidan Devaney 38 | |
| Wed., 5/18 | V Softball | Torrington | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:30 p.m. | L 1-21 | |
| Wed., 5/18 | V Softball | Ansonia | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 5:45 p.m. | L 0-18 | |
| Thu., 5/19 | V Boys Golf | Wolcott | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Aidan Devaney 44 Aoife Devaney 45 Laniah Moffet 41 | |
| Fri., 5/20 | V Baseball | Seymour | Home - Wilby HS-Wilby H.S. [Directions] | 2:30 p.m. | L 2-21 | |
| Mon., 5/23 | V Girls Tennis | NVL Girls Tennis Individual Tournament | Away - Woodland HS-Tennis Courts | 12:00 p.m. | ||
| Tue., 5/24 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 5:00 p.m. | L 1-11 | |
| Tue., 5/24 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | Laniah Moffet 36 Aoife Devaney 44 Aidan Devaney 43 Branden Halle 72 | |
| Wed., 5/25 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 1:30 p.m. | ||
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class MM Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Mon., 6/6 | V Boys Golf | CIAC Division I Spring Championship | Away - Stanley GC | 8:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||