| Wilby 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 300 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 9/8 | V Football | Torrington | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 30-20 | |
| Sat., 9/10 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | Postponed | ||
| Sat., 9/10 | V Boys Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 1:30 p.m. | T 3-3 | |
| Wed., 9/14 | V Boys Cross Country | Torrington, WCA, Watertown | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Girls Cross Country | Watertown, Torrington, WCA | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Wed., 9/14 | JV Girls Volleyball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:15 p.m. | ||||||
| Thu., 9/15 | V Girls Volleyball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:45 p.m. | L 2-3 | |
| Thu., 9/15 | JV Girls Volleyball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 9/16 | V Football | Oxford | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | L 22-34 | |
| Fri., 9/16 | V Boys Soccer | Holy Cross | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 0-7 | |
| Fri., 9/16 | V Girls Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 5:00 p.m. | ||
| Fri., 9/16 | V Girls Volleyball | Crosby | Home - Wilby HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/16 | JV Girls Volleyball | Crosby | Home - Wilby HS-Gym [Directions] | 4:45 p.m. | ||
| Sat., 9/17 | FM Football | Oxford | Home - Wilby HS-Football Field [Directions] | 10:00 a.m. | ||
| Tue., 9/20 | V Boys Cross Country | Oxford, Crosby | Away - Oxford HS-OHS XC TRAIL [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Naugatuck | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 1-6 | |
| Tue., 9/20 | V Girls Cross Country | Oxford, Crosby | Away - Oxford HS-OHS XC TRAIL [Directions] | 4:30 p.m. | ||
| Wed., 9/21 | V Girls Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | Postponed | ||
| Wed., 9/21 | V Girls Volleyball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | L 1-3 | |
| Wed., 9/21 | JV Girls Volleyball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | V Girls Volleyball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 9/23 | JV Girls Volleyball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | V Football | Gilbert/Northwestern/Housy | Away - Gilbert School-Football Field [Directions] | 1:00 p.m. | L 0-35 | |
| Sat., 9/24 | FM Football | Gilbert/Northwestern/Housy | Home - Wilby HS-Football Field [Directions] | Postponed | ||
| Tue., 9/27 | V Boys Cross Country | Woodland, Holy Cross, Naugatuck | Away - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Soccer | Watertown | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 2-5 | |
| Tue., 9/27 | V Girls Cross Country | Woodland, Holy Cross, Naugatuck | Away - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 4:15 p.m. | ||
| Tue., 9/27 | V Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/27 | JV Girls Volleyball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 9/28 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Thu., 9/29 | V Boys Soccer | Kennedy | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | T 1-1 | |
| Thu., 9/29 | JV Boys Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | Canceled | Cancelled | |
| Thu., 9/29 | V Girls Volleyball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 9/29 | JV Girls Volleyball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:30 p.m. | L 16-35 | |
| Fri., 9/30 | V Girls Swimming and Diving | Naugatuck | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | FM Football | Wolcott | Home - Wilby HS-Football Field [Directions] | 9:30 a.m. | ||
| Mon., 10/3 | V Boys Soccer | Ansonia | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | T 2-2 | |
| Mon., 10/3 | V Girls Volleyball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Mon., 10/3 | JV Girls Volleyball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Cross Country | Derby, St. Paul Catholic, Wolcott | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 4:45 p.m. | ||
| Tue., 10/4 | V Girls Cross Country | Derby, St. Paul Catholic, Wolcott | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 4:45 p.m. | ||
| Tue., 10/4 | V Girls Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 6:00 p.m. | ||
| Thu., 10/6 | FM Football | St. Paul Catholic | Home - Wilby HS-Football Field [Directions] | Canceled | Cancelled | |
| Thu., 10/6 | V Boys Soccer | Seymour | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 1-4 | |
| Thu., 10/6 | V Girls Volleyball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/6 | JV Girls Volleyball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Boys Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 4:00 p.m. | L 0-6 | |
| Fri., 10/7 | V Girls Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/7 | JV Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/8 | V Football | Derby | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 11:00 a.m. | W 36-0 | |
| Mon., 10/10 | JV Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 12:00 p.m. | ||
| Tue., 10/11 | V Boys Cross Country | Kennedy | Away - Bucks Hill Park #2-Buck Hill Park #2 [Directions] | 3:45 p.m. | ||
| Tue., 10/11 | V Boys Soccer | Woodland | Home - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | L 0-6 | |
| Tue., 10/11 | V Girls Cross Country | Kennedy | Away - Bucks Hill Park #2-Buck Hill Park #2 [Directions] | 3:45 p.m. | ||
| Tue., 10/11 | V Girls Volleyball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 0-3 | |
| Tue., 10/11 | JV Girls Volleyball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 10/13 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/13 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Watertown | Home - Wilby HS-Gil Cyr Natatorium [Directions] | 5:00 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Mon., 10/17 | V Boys Soccer | WCA | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 1-4 | |
| Tue., 10/18 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 3:45 p.m. | L 3-6 | |
| Tue., 10/18 | V Girls Swimming and Diving | Kennedy, Torrington | Away - John F. Kennedy HS-John Reardon Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/18 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:00 p.m. | ||
| 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 Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | L 1-7 | |
| 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 Football | Kennedy | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 34-42 | |
| Fri., 10/21 | V Boys Soccer | Kennedy | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:30 p.m. | L 2-7 | |
| Sat., 10/22 | FM Football | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Soccer | Crosby | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 0-2 | |
| Mon., 10/24 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/24 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Boys Soccer | Kaynor Tech | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:45 p.m. | L 0-2 | |
| Wed., 10/26 | V Girls Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 10/26 | JV Girls Volleyball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | V Girls Volleyball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/27 | JV Girls Volleyball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/28 | V Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 8-42 | |
| Sat., 10/29 | FM Football | Watertown | Home - Wilby HS-Football Field [Directions] | 10:30 a.m. | ||
| Wed., 11/2 | FM Football | Crosby | Home - Wilby HS-Football Field [Directions] | 3:30 p.m. | ||
| Sat., 11/5 | V Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 10:00 a.m. | L 50-58 | |
| Thu., 11/10 | V Football | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 7:00 p.m. | W 40-20 | |
| Sat., 11/12 | FM Football | St. Paul Catholic | Home - Wilby HS-Football Field [Directions] | Postponed | ||
| Wed., 11/23 | V Football | WCA | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 14-31 | |
| Tue., 12/13 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | L 15-76 | |
| Tue., 12/13 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/16 | V Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:45 p.m. | W 77-51 | |
| Fri., 12/16 | JV Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 12/16 | FR Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 18-50 | |
| Fri., 12/16 | JV Girls Basketball | Woodland | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 12/19 | FR Boys Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Mon., 12/19 | V Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:30 p.m. | W 32-31 | |
| Mon., 12/19 | JV Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Boys Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 63-56 | |
| Tue., 12/20 | JV Boys Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/21 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | L 16-62 | |
| Wed., 12/21 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/27 | V Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 63-38 | |
| Tue., 12/27 | JV Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/27 | FR Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Wed., 12/28 | V Boys Basketball | Washington (WV) | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | W 71-54 | |
| Wed., 12/28 | JV Boys Basketball | Washington (WV) | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 12/30 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | W 72-37 | |
| Fri., 12/30 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/30 | V Girls Basketball | Derby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | W 43-19 | |
| Tue., 1/3 | V Boys Basketball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 61-60 OT | |
| Tue., 1/3 | JV Boys Basketball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 21-60 | |
| Tue., 1/3 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | FR Boys Basketball | St. Paul Catholic | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 1/5 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | L 51-52 | |
| Fri., 1/6 | JV Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Holy Cross | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Fri., 1/6 | V Girls Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 39-60 | |
| Fri., 1/6 | JV Girls Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/9 | V Boys Basketball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 81-51 | |
| Mon., 1/9 | JV Boys Basketball | Kaynor Tech | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 27-45 | |
| Tue., 1/10 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/11 | V Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 76-59 | |
| Wed., 1/11 | JV Boys Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 1/13 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | L 71-87 | |
| Fri., 1/13 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Woodland | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Fri., 1/13 | V Girls Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 21-60 | |
| Fri., 1/13 | JV Girls Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | V Boys Basketball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 61-59 | |
| Tue., 1/17 | JV Boys Basketball | Ansonia | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:30 p.m. | L 27-61 | |
| Tue., 1/17 | JV Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | W 84-61 | |
| Fri., 1/20 | JV Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Watertown | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Fri., 1/20 | V Girls Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 24-75 | |
| Fri., 1/20 | JV Girls Basketball | Wolcott | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:15 p.m. | W 86-57 | |
| Tue., 1/24 | JV Boys Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:45 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | L 21-48 | |
| Tue., 1/24 | JV Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 1/25 | FR Boys Basketball | Oxford | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Thu., 1/26 | V Girls Basketball | Shepaug Valley | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 24-41 | |
| Thu., 1/26 | JV Girls Basketball | Shepaug Valley | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 55-63 | |
| Fri., 1/27 | JV Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | Canceled | Cancelled | |
| Fri., 1/27 | V Girls Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 22-75 | |
| Fri., 1/27 | JV Girls Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | V Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | L 76-79 | |
| Tue., 1/31 | JV Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | V Boys Swimming and Diving | Kennedy | Away - John F. Kennedy HS-John Reardon Pool [Directions] | Canceled | Cancelled | |
| Tue., 1/31 | V Girls Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 24-83 | |
| Tue., 1/31 | JV Girls Basketball | Seymour | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/2 | V Girls Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 24-66 | |
| Thu., 2/2 | JV Girls Basketball | Watertown | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Oxford | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Mon., 2/6 | FR Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 2/7 | V Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 65-72 | |
| Tue., 2/7 | JV Boys Basketball | Crosby | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | L 37-51 | |
| Tue., 2/7 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Canceled | Cancelled | |
| Thu., 2/9 | FR Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 2/9 | V Girls Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 32-62 | |
| Thu., 2/9 | JV Girls Basketball | Kennedy | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | L 69-79 | |
| Fri., 2/10 | JV Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 63-81 | |
| Tue., 2/14 | JV Boys Basketball | Holy Cross | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 18-87 | |
| Tue., 2/14 | JV Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/16 | FR Boys Basketball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 2/16 | V Boys Swimming and Diving | Woodland, Oxford | Away - Woodland HS-pool [Directions] | 5:30 p.m. | ||
| Thu., 2/16 | V Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | L 15-55 | |
| Thu., 2/16 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/17 | V Boys Basketball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 67-56 | |
| Fri., 2/17 | JV Boys Basketball | Naugatuck | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/17 | V Boys Swimming and Diving | Crosby/WCA | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Mon., 2/20 | FR Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 2/21 | V Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 64-99 | |
| Tue., 2/21 | JV Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/24 | V Boys Swimming and Diving | Seymour | Home - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Mon., 4/3 | V Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | 2:45 p.m. | L 2-12 | |
| Mon., 4/3 | V Softball | Kennedy | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:00 p.m. | W 28-9 | |
| Mon., 4/3 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 2:45 p.m. | L 1-6 | |
| Tue., 4/4 | V Boys Outdoor Track | Oxford, Holy Cross | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Girls Outdoor Track | Oxford, Holy Cross | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Softball | Crosby | Away - Crosby HS-CHS Softball Field #1 [Directions] | 3:30 p.m. | L 5-22 | |
| Wed., 4/5 | V Baseball | Torrington | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 0-15 | |
| Wed., 4/5 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 3:45 p.m. | L 1-17 | |
| Wed., 4/5 | V Girls Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | L 0-7 | |
| Wed., 4/5 | V Girls Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:00 p.m. | L 0-7 | |
| Thu., 4/6 | V Baseball | Crosby | Home - Wilby HS-Wilby H.S. [Directions] | 3:30 p.m. | L 5-9 | |
| Thu., 4/6 | V Girls Tennis | St. Paul Catholic | Away - Page Park -Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Sat., 4/8 | V Baseball | WCA | Home - Wilby HS-Wilby H.S. [Directions] | 12:00 p.m. | W 6-5 | |
| Sat., 4/8 | V Softball | WCA | Away - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | 11:00 a.m. | L 0-13 | |
| Mon., 4/10 | V Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 11:00 a.m. | L 0-16 | |
| Mon., 4/10 | V Softball | Woodland | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 11:00 a.m. | L 0-20 | |
| Tue., 4/11 | V Boys Outdoor Track | Watertown, St. Paul Catholic | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 11:00 a.m. | L 0-5 | |
| Tue., 4/11 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 12:15 p.m. | L 0-5 | |
| Tue., 4/11 | V Girls Outdoor Track | Watertown, St. Paul Catholic | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | ||
| Wed., 4/12 | V Baseball | Wolcott | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 2:00 p.m. | L 0-24 | |
| Mon., 4/17 | V Baseball | Holy Cross | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 1-21 | |
| Mon., 4/17 | V Softball | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 3:30 p.m. | L 0-12 | |
| Tue., 4/18 | V Boys Outdoor Track | Derby, WCA | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 2:45 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | Derby, WCA | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 2:45 p.m. | ||
| Tue., 4/18 | V Softball | Wolcott | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 0-21 | |
| Tue., 4/18 | V Girls Tennis | Woodland | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/19 | V Boys Golf | Holy Cross | Away - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | ||
| Wed., 4/19 | V Girls Tennis | Wolcott | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:15 p.m. | L 0-7 | |
| Wed., 4/19 | V Girls Tennis | Wolcott | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:00 p.m. | L 0-7 | |
| Thu., 4/20 | V Boys Tennis | Crosby | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 2:30 p.m. | W 5-0 | |
| Thu., 4/20 | V Boys Tennis | Crosby | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 4/21 | V Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 3:30 p.m. | L 5-7 | |
| Fri., 4/21 | V Softball | Crosby | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 15-19 | |
| Fri., 4/21 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W 5-1 | |
| Sat., 4/22 | JV Baseball | WCA | Home - Wilby HS-Wilby H.S. [Directions] | 11:00 a.m. | ||
| Mon., 4/24 | V Baseball | Watertown | Away - Deland Field-Deland field [Directions] | 3:45 p.m. | L 0-12 | |
| Mon., 4/24 | V Boys Golf | Seymour, Oxford | Away - Seymour HS-Oxford Greens [Directions] | 2:30 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 4/24 | V Softball | Watertown | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 1-21 | |
| Mon., 4/24 | V Girls Tennis | Watertown | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/25 | V Boys Golf | Torrington | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 4/25 | V Boys Outdoor Track | Wolcott | Away - Wolcott HS-Turf Field and Lower Field [Directions] | 3:30 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Naugatuck | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 1-4 | |
| Tue., 4/25 | V Girls Outdoor Track | Wolcott | Away - Wolcott HS-Turf Field and Lower Field [Directions] | 3:30 p.m. | ||
| Wed., 4/26 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:00 p.m. | L 0-10 | |
| Wed., 4/26 | V Boys Golf | Naugatuck | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 4/26 | V Softball | St. Paul Catholic | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 4:30 p.m. | L 3-17 | |
| Wed., 4/26 | V Girls Tennis | St. Paul Catholic | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:30 p.m. | L 0-7 | |
| Thu., 4/27 | V Boys Golf | Woodland | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Fri., 4/28 | V Baseball | Derby | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 3-19 | |
| Fri., 4/28 | V Boys Tennis | Wolcott | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:00 p.m. | L 2-3 | |
| Fri., 4/28 | V Boys Tennis | Wolcott | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:30 p.m. | W 4-1 | |
| Fri., 4/28 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | 5:30 p.m. | L 0-16 | |
| Mon., 5/1 | V Boys Tennis | Kennedy | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 5/2 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | Torrington, Naugatuck | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Torrington, Naugatuck | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Wed., 5/3 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:45 p.m. | L 1-11 | |
| Wed., 5/3 | V Boys Golf | St. Paul Catholic | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 5/3 | V Softball | Seymour | Home - Municipal Stadium [Directions] | 3:45 p.m. | L 0-19 | |
| Wed., 5/3 | V Girls Tennis | Seymour | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/4 | V Boys Golf | Wolcott | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Thu., 5/4 | V Softball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Softball Diamond [Directions] | 3:45 p.m. | L 13-18 | |
| Fri., 5/5 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 6:00 p.m. | L 1-14 | |
| Fri., 5/5 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 2:30 p.m. | L Forfeit | |
| Fri., 5/5 | V Softball | Naugatuck | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 1-16 | |
| Fri., 5/5 | V Girls Tennis | Naugatuck | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 5/6 | V Baseball | Kennedy | Home - Waterville Park-Baseball Field [Directions] | 10:00 a.m. | L 6-10 | |
| Mon., 5/8 | V Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 0-15 | |
| Mon., 5/8 | V Boys Golf | Watertown | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Mon., 5/8 | V Boys Tennis | Holy Cross | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:30 p.m. | L 0-5 | |
| Mon., 5/8 | V Softball | Holy Cross | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | L 0-13 | |
| Mon., 5/8 | V Girls Tennis | Holy Cross | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/9 | V Baseball | Oxford | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | L 0-14 | |
| Tue., 5/9 | V Boys Outdoor Track | Seymour, Woodland | Home - Seymour HS-Seymour High School Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 2:30 p.m. | L Forfeit | |
| Tue., 5/9 | V Girls Outdoor Track | Seymour, Woodland | Home - Seymour HS-Seymour High School Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 5/9 | V Softball | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 3:30 p.m. | L 15-27 | |
| Wed., 5/10 | V Boys Golf | Holy Cross | Home - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 5/10 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:00 p.m. | L 0-21 | |
| Thu., 5/11 | JV Baseball | WCA | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | ||
| Fri., 5/12 | V Baseball | WCA | Away - Bucks Hill (MONTOE) Park-Baseball Field [Directions] | 3:15 p.m. | W 11-1 | |
| Fri., 5/12 | V Boys Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:30 p.m. | L 1-4 | |
| Fri., 5/12 | V Boys Tennis | Torrington | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:00 p.m. | L 1-4 | |
| Fri., 5/12 | V Softball | WCA | Home - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:15 p.m. | L 0-15 | |
| Fri., 5/12 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | L 0-7 | |
| Sat., 5/13 | JV Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | 12:00 p.m. | ||
| Mon., 5/15 | V Baseball | Ansonia | Home - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | L 0-11 | |
| Mon., 5/15 | V Boys Golf | Seymour, Oxford | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Watertown | Home - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 3-1 | |
| Mon., 5/15 | V Softball | Ansonia | Away - Ansonia HS-Ansonia High School [Directions] | 3:30 p.m. | L 0-19 | |
| Mon., 5/15 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | 3:30 p.m. | L 0-7 | |
| Tue., 5/16 | JV Baseball | Watertown | Home - Wilby HS-Wilby H.S. [Directions] | Postponed | ||
| Tue., 5/16 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | Crosby, Kennedy | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Crosby, Kennedy | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Wed., 5/17 | V Baseball | Kaynor Tech | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | L 3-15 | |
| Wed., 5/17 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:30 p.m. | ||
| Thu., 5/18 | V Baseball | Hillhouse/Career | Away - Bowen Field-Baseball Field [Directions] | 3:00 p.m. | L 0-11 | |
| Thu., 5/18 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | ||
| Mon., 5/22 | V Boys Golf | St. Paul Catholic, Canton | Away - Westwoods Golf Course [Directions] | 2:15 p.m. | ||
| Wed., 5/24 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||