| Holy Cross 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 540 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/24 | V Football | Plainville (Scrim.) | Away - Plainville HS-Plainville HS- Tinty Field and Track [Directions] | 4:00 p.m. | ||
| Tue., 8/30 | V Girls Soccer | Thomaston (Scrim.) | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | V Football | Hillhouse (Scrim.) | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 9/1 | V Boys Soccer | Seymour (Scrim.) | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | JV Boys Soccer | Seymour (Scrim.) | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | V Girls Volleyball | Bristol Eastern (Scrim.) | Away - Bristol Eastern HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/1 | JV Girls Volleyball | Bristol Eastern (Scrim.) | Away - Bristol Eastern HS-Gym 2 [Directions] | 4:00 p.m. | ||
| Sun., 9/4 | V Girls Soccer | Granby Memorial Soccer Jamboree | Away - Granby Memorial HS-Stadium Field | 9:00 a.m. | ||
| Tue., 9/6 | V Boys Soccer | Masuk (Scrim.) | Away - Masuk HS-Masuk High School Middle Field [Directions] | Rainout | ||
| Tue., 9/6 | V Girls Soccer | Sacred Heart Academy (Scrim.) | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 9/9 | V Football | Kennedy | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | W 32-6 | |
| Fri., 9/9 | V Girls Volleyball | Suffield | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/9 | JV Girls Volleyball | Suffield | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 9/10 | JV Football | Kennedy | Home - Holy Cross [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | V Boys Soccer | Oxford | Home - Holy Cross-Alumni Field [Directions] | 12:00 p.m. | L 1-3 | |
| Sat., 9/10 | V Girls Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 1:00 p.m. | W 10-1 | |
| Mon., 9/12 | JV Girls Soccer | Haddam-Killingworth | Home - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | ||
| Tue., 9/13 | V Girls Volleyball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/13 | JV Girls Volleyball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 9/14 | V Boys Cross Country | Crosby, Derby, Kennedy | Away - Bucks Hill (MONTOE) Park-XC Course [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 3:45 p.m. | T 2-2 | |
| Wed., 9/14 | V Girls Cross Country | Crosby, Derby, Kennedy | Away - Bucks Hill (MONTOE) Park-Soccer Pitch [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Girls Soccer | St. Paul Catholic | Home - Holy Cross-Alumni Field [Directions] | 4:30 p.m. | W 8-2 | |
| Thu., 9/15 | V Football | Watertown | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | W 54-12 | |
| Fri., 9/16 | V Boys Soccer | Wilby | Away - Wilby HS-Pedro DeBrito Field [Directions] | 3:30 p.m. | W 7-0 | |
| Fri., 9/16 | V Girls Soccer | Wolcott | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 8-0 | |
| Fri., 9/16 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/16 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 9/17 | FM Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Tue., 9/20 | V Boys Cross Country | Seymour, WCA, Wolcott | Home - Holy Cross [Directions] | 3:45 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Kennedy | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 3-0 | |
| Tue., 9/20 | V Girls Cross Country | Seymour, WCA, Wolcott | Home - Holy Cross [Directions] | 3:45 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 3:45 p.m. | W 9-1 | |
| Tue., 9/20 | V Girls Volleyball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/20 | JV Girls Volleyball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 9/21 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Wed., 9/21 | JV Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | ||
| Wed., 9/21 | V Girls Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Wed., 9/21 | V Girls Soccer | Woodland | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:45 p.m. | T 3-3 | |
| Wed., 9/21 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Wed., 9/21 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 9/22 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 4:30 p.m. | ||
| Fri., 9/23 | V Football | Seymour | Away - Seymour HS-turf field [Directions] | 7:00 p.m. | W 28-21 | |
| Fri., 9/23 | V Boys Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Sat., 9/24 | JV Football | Seymour | Home - Holy Cross [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | JV Boys Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | Canceled | Cancelled | |
| Sat., 9/24 | FR Girls Volleyball | Torrington, Naugatuck, Watertown | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 9:00 a.m. | ||
| Tue., 9/27 | V Boys Cross Country | Woodland, Naugatuck, Wilby | Away - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Soccer | Crosby | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 7-0 | |
| Tue., 9/27 | V Girls Cross Country | Woodland, Naugatuck, Wilby | Away - Woodland HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-1 | |
| Tue., 9/27 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/27 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 9/28 | JV Girls Volleyball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 9/30 | JV Football | WCA | Away - Waterbury Career Academy-Football Field [Directions] | 3:45 p.m. | ||
| Fri., 9/30 | V Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/30 | V Girls Soccer | Seymour | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 5-0 | |
| Fri., 9/30 | V Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/30 | JV Girls Volleyball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 4:15 p.m. | ||
| Sat., 10/1 | V Football | WCA | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 4:00 p.m. | W 48-12 | |
| Sat., 10/1 | JV Boys Soccer | Oxford | Home - Holy Cross-Alumni Field [Directions] | Postponed | ||
| Mon., 10/3 | V Boys Soccer | WCA | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 2-1 | |
| Tue., 10/4 | V Boys Cross Country | Oxford, Torrington | Home - Holy Cross [Directions] | 3:45 p.m. | ||
| Tue., 10/4 | V Girls Cross Country | Cross Country | Home - Holy Cross [Directions] | 3:45 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:00 p.m. | W 7-1 | |
| Tue., 10/4 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/4 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 10/5 | V Boys Soccer | Torrington | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/5 | JV Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | Postponed | ||
| Thu., 10/6 | V Football | Naugatuck | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | W 21-19 | |
| Thu., 10/6 | V Girls Volleyball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 10/6 | JV Girls Volleyball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | L 1-2 | |
| Fri., 10/7 | V Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/7 | JV Girls Volleyball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 4:45 p.m. | ||
| Sat., 10/8 | FM Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | JV Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 10/10 | V Boys Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | L 3-0 | |
| Tue., 10/11 | V Boys Cross Country | Watertown, St. Paul Catholic | Away - Veterans Memorial Park-Veterans Park XC Course [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Boys Soccer | Ansonia | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 8-0 | |
| Tue., 10/11 | V Girls Cross Country | Watertown, St. Paul Catholic | Away - Watertown HS-Veteran's Park [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Ave [Directions] | 3:30 p.m. | W 5-1 | |
| Tue., 10/11 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/11 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 4:45 p.m. | ||
| Tue., 10/11 | FR Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 3:00 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 6:00 p.m. | W 8-0 | |
| Thu., 10/13 | V Girls Soccer | Notre Dame-Fairfield | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | L 0-9 | |
| Thu., 10/13 | V Girls Volleyball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/13 | JV Girls Volleyball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 10/14 | V Girls Soccer | Derby | Home - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 3:00 p.m. | W 8-1 | |
| Sat., 10/15 | V Boys Soccer | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 2:00 p.m. | W 3-0 | |
| Tue., 10/18 | V Girls Volleyball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/18 | JV Girls Volleyball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 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 | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | W 2-1 | |
| Wed., 10/19 | V Girls Cross Country | NVL XC Championships | Away - Veterans Memorial Park-Veterans Park XC Course | 2:00 p.m. | ||
| Wed., 10/19 | V Girls Soccer | Naugatuck | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | W 9-4 | |
| Wed., 10/19 | V Girls Volleyball | Housatonic Regional | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/19 | JV Girls Volleyball | Housatonic Regional | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Thu., 10/20 | JV Boys Soccer | Naugatuck | Away - Rotary Field-Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/20 | V Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/20 | JV Girls Volleyball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 4:45 p.m. | ||
| Fri., 10/21 | V Football | Ansonia | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | L 28-31 | |
| Sat., 10/22 | JV Football | Ansonia | Away - Nolan Field-Ansonia-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | JV Boys Soccer | Seymour | Away - Seymour HS-Seymour High Lower Field [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | V Girls Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 11:00 a.m. | L 1-6 | |
| Mon., 10/24 | V Boys Soccer | Wolcott | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:30 p.m. | W 4-1 | |
| Mon., 10/24 | V Girls Soccer | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:30 p.m. | W 1-0 | |
| Tue., 10/25 | JV Girls Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/25 | V Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 6:00 p.m. | L 3-0 | |
| Tue., 10/25 | JV Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | V Boys Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 1-0 | |
| Wed., 10/26 | V Girls Soccer | Watertown | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:30 p.m. | L 1-2 | |
| Wed., 10/26 | V Girls Volleyball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 10/26 | JV Girls Volleyball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Thu., 10/27 | V Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/27 | JV Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/28 | FM Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | Postponed | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class SS Championship | Away - Wickham Park | 1:30 p.m. | ||
| Sat., 10/29 | V Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 10:00 a.m. | W 35-8 | |
| Sat., 10/29 | V Boys Soccer | St. Paul Catholic | Home - Naugatuck HS-Veterans Field [Directions] | 5:00 p.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park | 12:55 p.m. | ||
| Sat., 10/29 | V Girls Soccer | Naugatuck | Home - Post University [Directions] | 3:30 p.m. | W 8-2 | |
| Sat., 10/29 | V Girls Volleyball | Oxford | Home - Holy Cross HS-Tim McDonald Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 11/1 | V Boys Soccer | Torrington | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 11/1 | V Girls Soccer | Watertown | Away - Wolcott HS-Turf Field [Directions] | 7:30 p.m. | L 0-1 | |
| Tue., 11/1 | V Girls Volleyball | Woodland | Home - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 11/3 | V Boys Soccer | Oxford | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:30 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Woodland | Away - Woodland HS-Woodland Football Field [Directions] | 6:00 p.m. | L 7-20 | |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Sat., 11/5 | FM Football | Woodland | Away - Woodland HS-Woodland Football Field [Directions] | 10:00 a.m. | ||
| Sat., 11/5 | V Girls Soccer | Ridgefield (Scrim.) | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 10:00 a.m. | L 1-4 | |
| Mon., 11/7 | V Boys Soccer | Windham Tech | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 2:00 p.m. | ||
| Tue., 11/8 | V Girls Soccer | Bristol Central | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Boys Soccer | Weston | Away - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | ||
| Wed., 11/9 | V Girls Volleyball | Wheeler | Home - Holy Cross HS-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 11/10 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 2:00 p.m. | ||
| Sat., 11/12 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:30 a.m. | ||
| Mon., 11/14 | V Football | Torrington | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | W 56-6 | |
| Thu., 11/24 | V Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 10:00 a.m. | W 42-13 | |
| Fri., 11/25 | FM Football | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 11/29 | V Football | New Fairfield | Home - Municipal Stadium Complex (Waterbury, CT) [Directions] | 6:30 p.m. | ||
| Fri., 12/2 | V Girls Ice Hockey | Fairfield Ludlowe/Warde (Scrim.) | Away - Wonderland of Ice-New [Directions] | 7:30 p.m. | ||
| Sat., 12/3 | V Girls Basketball | Brookfield (Scrim.) | Away - Brookfield HS-BHS Big Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/3 | V Girls Ice Hockey | Shelton Jamboree | Away - Shelton - Sports Center of CT | 7:00 p.m. | ||
| Sat., 12/3 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:45 p.m. | ||
| Sun., 12/4 | V Football | Bloomfield | Away - Bloomfield HS-Phil Rubin Stadium- Turf Field & Track [Directions] | 12:30 p.m. | ||
| Mon., 12/5 | V Boys Basketball | Ridgefield (Scrim.) | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/5 | V Girls Basketball | Sacred Heart Academy (Scrim.) | Away - Sacred Heart Academy-Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/6 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:30 p.m. | L 2-4 | |
| Wed., 12/7 | V Boys Basketball | Wilton (Scrim.) | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/7 | V Girls Basketball | West Haven (Scrim.) | Away - West Haven HS-Gym [Directions] | 3:00 p.m. | ||
| Fri., 12/9 | V Girls Basketball | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/9 | JV Girls Basketball | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | ||
| Mon., 12/12 | V Boys Basketball | Guilford (Scrim.) | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/14 | V Wrestling | Gilbert/Torrington | Away - Gilbert School-Gym [Directions] | 6:30 p.m. | ||
| Wed., 12/14 | V Girls Basketball | Mercy | Away - Mercy HS-Gym [Directions] | 7:00 p.m. | L 51-56 | |
| Wed., 12/14 | JV Girls Basketball | Mercy | Away - Mercy HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/14 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 12/17 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/17 | V Wrestling | Darien Invitational | Away - Darien HS-DHS Main Gym | 8:00 a.m. | ||
| Sat., 12/17 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | Postponed | ||
| Sat., 12/17 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks-Rink 1 [Directions] | 4:10 p.m. | L 0-2 | |
| Mon., 12/19 | FR Boys Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Boys Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 77-70 | |
| Tue., 12/20 | JV Boys Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 12/20 | V Boys Swimming and Diving | Crosby/WCA | Home - Kennedy HS (Waterbury) [Directions] | 5:00 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:00 p.m. | W 74-42 | |
| Tue., 12/20 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Canceled | Cancelled | |
| Wed., 12/21 | V Wrestling | Nonnewaug | Home - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/21 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:15 p.m. | W 4-3 | |
| Thu., 12/22 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | W 60-51 | |
| Thu., 12/22 | JV Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/22 | FR Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 3:30 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:30 p.m. | W 81-51 | |
| Fri., 12/23 | FR Boys Basketball | Oxford | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Postponed | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 2/8, Time to 6:30 p.m. | ||||||
| Tue., 12/27 | V Wrestling | Jonathan Law, Bunnell, Masuk, Middletown, Morgan, North Haven, Platt, Plainville, Ridgefield, Shelton, Harding | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium | 9:00 a.m. | ||
| Tue., 12/27 | V Girls Basketball | St. Marys Bay View (RI) | Home - Mohegan Sun Arena-Arena [Directions] | 12:00 p.m. | W 71-63 | |
| Wed., 12/28 | V Boys Basketball | Oxford | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 84-65 | |
| Wed., 12/28 | JV Boys Basketball | Oxford | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/28 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 2:30 p.m. | W 3-0 | |
| Thu., 12/29 | V Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:00 p.m. | W 59-46 | |
| Thu., 12/29 | JV Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 4:15 p.m. | ||
| Thu., 12/29 | FR Boys Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 2:30 p.m. | ||
| Thu., 12/29 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Hamden-Lou Astorino Ice Rink [Directions] | 12:00 p.m. | L 1-3 | |
| Fri., 12/30 | V Boys Basketball | Woodland | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 88-60 | |
| Fri., 12/30 | JV Boys Basketball | Woodland | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/30 | FR Boys Basketball | Woodland | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 12/30 | V Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:00 p.m. | W 72-30 | |
| Fri., 12/30 | JV Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | Postponed | ||
| Mon., 1/2 | FR Girls Basketball | Sacred Heart Academy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Tue., 1/3 | V Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 7:00 p.m. | W 71-54 | |
| Tue., 1/3 | JV Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 51-33 | |
| Tue., 1/3 | JV Girls Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Girls Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 1/4 | V Wrestling | Terryville-Thomaston | Away - Terryville HS-Gym [Directions] | 6:30 p.m. | ||
| Wed., 1/4 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | L 0-2 | |
| Thu., 1/5 | FR Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | L 55-58 | |
| Fri., 1/6 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby HS-Gil Cyr Natatorium [Directions] | Canceled | Cancelled | |
| Fri., 1/6 | V Girls Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 74-34 | |
| Fri., 1/6 | JV Girls Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 1/7 | V Wrestling | Warrior Invitational | Away - Canton HS-Gym | 9:30 a.m. | ||
| Sat., 1/7 | V Girls Basketball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:30 p.m. | W 57-45 | |
| Sat., 1/7 | JV Girls Basketball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 1/7 | FR Girls Basketball | Brookfield | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Postponed | ||
| Sat., 1/7 | FR Girls Basketball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 2:00 p.m. | ||
| Sat., 1/7 | V Girls Ice Hockey | East Catholic Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 1-2 (OT) | |
| Tue., 1/10 | V Boys Basketball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 87-53 | |
| Tue., 1/10 | JV Boys Basketball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/10 | V Boys Swimming and Diving | Brookfield | Home - Kennedy HS (Waterbury) [Directions] | 5:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 79-21 | |
| Tue., 1/10 | JV Girls Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:15 p.m. | ||
| Wed., 1/11 | V Wrestling | Northwestern | Home - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/11 | V Girls Basketball | Derby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 73-40 | |
| Wed., 1/11 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | W 9-3 | |
| Fri., 1/13 | V Boys Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 66-77 | |
| Fri., 1/13 | JV Boys Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Torrington | Home - Kennedy HS (Waterbury) [Directions] | 7:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | W 84-33 | |
| Fri., 1/13 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 1/14 | V Wrestling | Darien, Bunnell, New Fairfield, Weston | Away - Darien HS-DHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 1/14 | FR Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | V Girls Ice Hockey | Avon | Away - Newington-Blue Rink [Directions] | 4:10 p.m. | L 0-3 | |
| Tue., 1/17 | V Boys Basketball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 70-51 | |
| Tue., 1/17 | JV Boys Basketball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | W 62-53 | |
| Tue., 1/17 | JV Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | FR Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/18 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 1/20 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | W 65-47 | |
| Fri., 1/20 | JV Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Seymour | Home - Kennedy HS (Waterbury) [Directions] | 6:00 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:00 p.m. | W 65-39 | |
| Fri., 1/20 | JV Girls Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Postponed | ||
| Sat., 1/21 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 7-4 | |
| Mon., 1/23 | FR Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | Postponed | ||
| Mon., 1/23 | FR Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | Postponed | ||
| Tue., 1/24 | V Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | W 70-41 | |
| Tue., 1/24 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 72-46 | |
| Tue., 1/24 | JV Girls Basketball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Girls Basketball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 1/26 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:00 p.m. | ||
| Thu., 1/26 | V Wrestling | North Haven | Home - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/26 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 1/27 | V Boys Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 63-55 | |
| Fri., 1/27 | JV Boys Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/27 | V Boys Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Fri., 1/27 | V Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 75-22 | |
| Fri., 1/27 | JV Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | V Girls Indoor Track | NVL INDOOR TRACK AND FIELD CHAMPIONSHIP | Away - New Haven Athletic Center/Hillhouse HS | 5:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:15 p.m. | ||||||
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Away - Brookfield HS-BHS Small Gym | 9:30 a.m. | ||
| Sat., 1/28 | FR Girls Basketball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 1/28 | V Girls Ice Hockey | Simsbury | Away - Simsbury - ISCC-NHL [Directions] | 5:40 p.m. | T 2-2 | |
| Tue., 1/31 | V Boys Basketball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 86-76 | |
| Tue., 1/31 | JV Boys Basketball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | L 76-71 | |
| Tue., 1/31 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | W 8-1 | |
| Thu., 2/2 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | L 67-76 | |
| Fri., 2/3 | JV Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Postponed | ||
| Fri., 2/3 | V Boys Swimming and Diving | Kennedy | Home - Kennedy HS (Waterbury) [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 72-33 | |
| Fri., 2/3 | JV Girls Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 2/4 | V Wrestling | Stafford Wrestling Invitation Tournament | Away - Stafford HS-Gym | 9:15 a.m. | ||
| Sat., 2/4 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 4-1 | |
| Mon., 2/6 | V Boys Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 5:00 p.m. | ||
| Tue., 2/7 | V Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 99-76 | |
| Tue., 2/7 | JV Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | W 75-49 | |
| Tue., 2/7 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/8 | V Wrestling | St. Paul Catholic | Home - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/8 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | W 5-0 | |
| Thu., 2/9 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/9 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 2/11 | V Boys Basketball | Conard | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:00 p.m. | W 55-53 | |
| Sat., 2/11 | JV Boys Basketball | Conard | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Sat., 2/11 | V Wrestling | BVL Wrestling Championships | Home - Derby HS-DHS Vitello Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/11 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:45 p.m. | L 2-3 | |
| Mon., 2/13 | FR Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 81-63 | |
| Tue., 2/14 | JV Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 87-18 | |
| Tue., 2/14 | JV Girls Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | L 5-6 | |
| Thu., 2/16 | V Girls Basketball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 86-51 | |
| Thu., 2/16 | JV Girls Basketball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/16 | FR Girls Basketball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/17 | V Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 102-58 | |
| Fri., 2/17 | JV Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/17 | FR Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/17 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 5:30 p.m. | ||
| Fri., 2/17 | V Wrestling | CIAC M Championship | Away - Jonathan Law | 4:00 p.m. | ||
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC M Championship | Away - Jonathan Law | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Basketball | Naugatuck | Home - Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:15 p.m. | ||
| Sat., 2/18 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 6-0 | |
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Girls Basketball | Wolcott | Home - Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:30 p.m. | ||
| Mon., 2/20 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | ||
| Tue., 2/21 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 7:00 p.m. | W 97-62 | |
| Tue., 2/21 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | 3:30 p.m. | ||
| Thu., 2/23 | V Girls Basketball | St. Paul Catholic | Away - Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | V Boys Basketball | Torrington | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 7:15 p.m. | ||
| Wed., 3/1 | V Boys Basketball | Kennedy | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 3/2 | V Girls Basketball | Masuk | Home - Holy Cross-gym [Directions] | 6:30 p.m. | ||
| Mon., 3/6 | V Girls Basketball | New Milford | Home - Holy Cross-gym [Directions] | 7:00 p.m. | ||
| Tue., 3/7 | V Boys Basketball | St. Joseph | Home - Holy Cross-gym [Directions] | 6:30 p.m. | ||
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Thu., 3/9 | V Boys Basketball | Conard | Home - Holy Cross-gym [Directions] | 6:30 p.m. | ||
| Fri., 3/10 | V Girls Basketball | E.O. Smith | Home - New Britain HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class S Trials | Away - East Hartford | 4:30 p.m. | ||
| Mon., 3/13 | V Boys Basketball | Staples | Home - Holy Cross-gym [Directions] | 7:00 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class S Finals | Away - SCSU | 1:00 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Thu., 3/23 | V Softball | Nonnewaug (Scrim.) | Home - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 4:00 p.m. | ||
| Fri., 3/24 | V Baseball | Pomperaug (Scrim.) | Away - Pomperaug HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 3/24 | V Softball | Brookfield (Scrim.) | Home - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 4:15 p.m. | ||
| Sat., 3/25 | V Softball | Norwalk (Scrim.) | Away - Norwalk HS-Ray Barry Field [Directions] | 11:00 a.m. | Cancelled | |
| Mon., 3/27 | V Boys Lacrosse | Granby Memorial (Scrim.) | Away - Granby Memorial HS-Stadium Field [Directions] | 4:30 p.m. | ||
| Mon., 3/27 | V Softball | New Fairfield (Scrim.) | Home - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 4:15 p.m. | ||
| Tue., 3/28 | V Softball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | ||
| Wed., 3/29 | V Boys Lacrosse | Morgan (Scrim.) | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | ||
| Wed., 3/29 | V Boys Lacrosse | TBA | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 3/30 | V Baseball | Shelton (Scrim.) | Away - Shelton HS-Baseball Diamond - N Constitution Blvd [Directions] | 4:00 p.m. | ||
| Sat., 4/1 | V Boys Lacrosse | Pomperaug | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 11:30 a.m. | L 7-20 | |
| Sat., 4/1 | JV Boys Lacrosse | Pomperaug | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/1 | V Softball | WCA | Home - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 2:30 p.m. | W 17-2 | |
| Mon., 4/3 | V Baseball | Ansonia | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 11-1 | |
| Mon., 4/3 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | L 2-3 | |
| Mon., 4/3 | V Softball | Ansonia | Away - Ansonia HS-Ansonia High School [Directions] | 3:30 p.m. | W 19-4 | |
| Mon., 4/3 | V Girls Tennis | Woodland | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 4-3 [Detailed Results] | |
| Tue., 4/4 | V Baseball | WCA | Away - Bucks Hill (MONTOE) Park-Baseball Field [Directions] | 4:00 p.m. | W 12-1 | |
| Tue., 4/4 | V Boys Outdoor Track | Oxford, Wilby | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Girls Outdoor Track | Oxford, Wilby | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 4:00 p.m. | W 8-5 | |
| Tue., 4/4 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 4:00 p.m. | L 5-2 [Detailed Results] | |
| Wed., 4/5 | V Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 3:30 p.m. | W 19-0 | |
| Wed., 4/5 | V Boys Lacrosse | St. Paul Catholic | Home - Holy Cross-Municipal Stadium [Directions] | 4:45 p.m. | W 16-8 | |
| Wed., 4/5 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W 5-0 | |
| Wed., 4/5 | V Softball | Crosby | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 16-1 | |
| Wed., 4/5 | V Girls Tennis | Crosby | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/6 | V Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | 3:00 p.m. | L 4-3 | |
| Thu., 4/6 | V Softball | Derby | Away - Payden Park-Payden Field [Directions] | 4:00 p.m. | W 14-1 | |
| Sat., 4/8 | V Baseball | Derby | Home - Holy Cross-Alumni Field [Directions] | 10:00 a.m. | W 14-2 | |
| Sat., 4/8 | V Boys Outdoor Track | Naugatuck, Crosby | Away - Naugatuck HS-Veterans Field [Directions] | 10:00 a.m. | ||
| Sat., 4/8 | V Girls Outdoor Track | Naugatuck, Crosby | Away - Naugatuck HS-Veterans Field [Directions] | 10:00 a.m. | ||
| Mon., 4/10 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 1:00 p.m. | W 3-2 | |
| Mon., 4/10 | FR Baseball | Torrington | Away - Torrington High Baseball Field [Directions] | 1:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Torrington | Home - Holy Cross [Directions] | 3:30 p.m. | L 2-3 | |
| Mon., 4/10 | V Softball | Torrington | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 5-4 | |
| Mon., 4/10 | V Girls Tennis | Torrington | Home - Holy Cross-Tennis Courts [Directions] | 12:30 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/11 | JV Baseball | Torrington | Home - Holy Cross-Alumni Field [Directions] | 11:00 a.m. | W 8-3 | |
| Tue., 4/11 | V Boys Lacrosse | Capital Prep | Home - Holy Cross-Municipal Stadium [Directions] | 4:00 p.m. | W 14-0 | |
| Tue., 4/11 | V Boys Tennis | Kennedy | Home - Holy Cross-Tennis Courts [Directions] | 11:00 a.m. | L 0-5 | |
| Wed., 4/12 | V Baseball | Kennedy | Home - Holy Cross-Alumni Field [Directions] | 11:00 a.m. | W 8-3 | |
| Wed., 4/12 | V Softball | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 11:00 a.m. | W 14-1 | |
| Wed., 4/12 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 11:00 a.m. | W 5-1 [Detailed Results] | |
| Thu., 4/13 | V Boys Lacrosse | Bethel | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 3:45 p.m. | L 11-15 | |
| Fri., 4/14 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 11:00 a.m. | W 2-1 | |
| Fri., 4/14 | V Softball | Oxford | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 4-3 | |
| Sat., 4/15 | JV Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 11:00 a.m. | L 11-11 | |
| Sat., 4/15 | JV Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 11:00 a.m. | ||
| Mon., 4/17 | V Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | W 21-1 | |
| Mon., 4/17 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 4:00 p.m. | W 22-3 | |
| Mon., 4/17 | V Softball | Wilby | Home - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 3:30 p.m. | W 12-0 | |
| Tue., 4/18 | V Girls Tennis | Ansonia | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Wed., 4/19 | V Baseball | Crosby | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 15-0 | |
| Wed., 4/19 | V Boys Golf | Naugatuck | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | HC 194 Naugatuck 202 | |
| Wed., 4/19 | V Boys Golf | Waterbury Coop | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | HC 194 CO-OP 182 | |
| Wed., 4/19 | V Boys Lacrosse | Litchfield Coop | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 18-3 | |
| Wed., 4/19 | V Boys Tennis | Crosby | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 [Detailed Results] | |
| Wed., 4/19 | V Softball | Crosby | Away - Crosby HS-CHS Softball Field #1 [Directions] | 3:30 p.m. | W 14-2 | |
| Wed., 4/19 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/20 | V Girls Tennis | Seymour | Home - Holy Cross-Tennis Courts [Directions] | 2:30 p.m. | W 5-2 [Detailed Results] | |
| Fri., 4/21 | V Baseball | WCA | Home - Holy Cross-Municipal Stadium [Directions] | 6:00 p.m. | W 16-1 | |
| Fri., 4/21 | V Boys Tennis | Wolcott | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 3-2 [Detailed Results] | |
| Fri., 4/21 | V Softball | WCA | Away - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | 5:30 p.m. | W 13-0 | |
| Sat., 4/22 | JV Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | 11:00 a.m. | W 15-0 | |
| Sat., 4/22 | V Softball | Immaculate | Home - Holy Cross-Alumni Field [Directions] | 10:30 a.m. | W 10-9 | |
| Sat., 4/22 | JV Softball | WCA | Away - Huntingdon Park #2 [Directions] | Canceled | Cancelled | |
| Mon., 4/24 | V Boys Golf | Woodland | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | ||
| Mon., 4/24 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 11-15 | |
| Tue., 4/25 | JV Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | W 10-3 | |
| Tue., 4/25 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 4/25 | V Boys Outdoor Track | St. Paul Catholic, Torrington | Home - Holy Cross-Holy Cross Track [Directions] | 3:00 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 2:45 p.m. | L 0-5 [Detailed Results] | |
| Tue., 4/25 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-5 [Detailed Results] | |
| Tue., 4/25 | V Girls Outdoor Track | St. Paul Catholic, Torrington | Home - Holy Cross-Holy Cross Track [Directions] | 3:00 p.m. | ||
| Wed., 4/26 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 4:00 p.m. | L 16-9 | |
| Wed., 4/26 | V Boys Golf | Seymour, Oxford | Away - Seymour HS-Oxford Greens [Directions] | 2:00 p.m. | ||
| Wed., 4/26 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | L 2-3 | |
| Wed., 4/26 | V Softball | Wolcott | Home - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | W 8-5 | |
| Wed., 4/26 | V Girls Tennis | Wolcott | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 4-3 [Detailed Results] | |
| Thu., 4/27 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 3:00 p.m. | ||
| Fri., 4/28 | V Baseball | Woodland | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 4/28 | FR Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 3:30 p.m. | L 7-2 | |
| Fri., 4/28 | V Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | 3:30 p.m. | L 0-12 | |
| Fri., 4/28 | V Girls Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Sat., 4/29 | JV Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 4/29 | V Boys Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 10:00 a.m. | L 4-17 | |
| Sat., 4/29 | JV Boys Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | Canceled | Cancelled | |
| Sat., 4/29 | JV Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | Postponed | ||
| Mon., 5/1 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | ||
| Mon., 5/1 | V Boys Lacrosse | Capital Prep | Away - Capital Preparatory Magnet School-Quirk MS [Directions] | 3:45 p.m. | W 16-0 | |
| Tue., 5/2 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | Kennedy, Seymour | Home - Holy Cross-Holy Cross Track [Directions] | 3:30 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Kennedy, Seymour | Home - Holy Cross-Holy Cross Track [Directions] | 3:30 p.m. | ||
| Wed., 5/3 | V Baseball | St. Paul Catholic | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | L 3-1 | |
| Wed., 5/3 | V Boys Golf | Torrington | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | ||
| Wed., 5/3 | V Girls Tennis | St. Paul Catholic | Away - Page Park -Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Thu., 5/4 | JV Baseball | St. Paul Catholic | Home - Holy Cross-Alumni Field [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Lacrosse | Wolcott | Home - Holy Cross-Municipal Stadium [Directions] | 3:45 p.m. | W 22-4 | |
| Thu., 5/4 | JV Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | Postponed | ||
| Fri., 5/5 | V Baseball | Watertown | Away - Deland Field-Deland field [Directions] | 3:45 p.m. | W 14-2 | |
| Fri., 5/5 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 2:30 p.m. | L 0-5 [Detailed Results] | |
| Fri., 5/5 | V Softball | Watertown | Home - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 3:00 p.m. | L 1-7 | |
| Sat., 5/6 | V Baseball | Cheshire | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 10:30 a.m. | L 5-3 | |
| Sat., 5/6 | V Boys Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 3:00 p.m. | L 10-17 | |
| Sat., 5/6 | JV Boys Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | Canceled | Cancelled | |
| Sat., 5/6 | V Boys Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Mon., 5/8 | V Baseball | Wilby | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 15-0 | |
| Mon., 5/8 | V Boys Golf | Wolcott | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | ||
| Mon., 5/8 | V Boys Lacrosse | Litchfield Coop | Away - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | W 15-6 | |
| Mon., 5/8 | JV Boys Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/8 | V Boys Tennis | Wilby | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 [Detailed Results] | |
| Mon., 5/8 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 5:30 p.m. | W 5-0 [Detailed Results] | |
| Mon., 5/8 | V Softball | Wilby | Away - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | W 13-0 | |
| Mon., 5/8 | V Girls Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/8 | V Girls Tennis | Watertown | Home - Wilby HS [Directions] | 4:30 p.m. | W 4-3 [Detailed Results] | |
| Tue., 5/9 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Wolcott, Derby | Away - Wolcott HS-Turf Field and Lower Field [Directions] | 3:30 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Watertown | Away - Holy Cross-Tennis Courts [Directions] | 2:45 p.m. | W 3-2 [Detailed Results] | |
| Tue., 5/9 | V Girls Outdoor Track | Wolcott, Derby | Away - Wolcott HS-Turf Field and Lower Field [Directions] | 3:30 p.m. | ||
| Tue., 5/9 | V Softball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Softball Field [Directions] | 4:00 p.m. | L 10-11 | |
| Tue., 5/9 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Wed., 5/10 | V Baseball | Naugatuck | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 6:00 p.m. | L 8-3 | |
| Wed., 5/10 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 5/10 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:00 p.m. | W 7-5 | |
| Wed., 5/10 | V Boys Tennis | Naugatuck | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 2-3 [Detailed Results] | |
| Wed., 5/10 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 5:45 p.m. | L 2-7 | |
| Wed., 5/10 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 5/10 | V Girls Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | W 5-2 [Detailed Results] | |
| Thu., 5/11 | V Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | 3:30 p.m. | W 3-1 | |
| Thu., 5/11 | JV Baseball | Naugatuck | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 5-5 | |
| Thu., 5/11 | JV Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | Postponed | ||
| Thu., 5/11 | V Boys Outdoor Track | Woodland, Watertown | Away - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 3:30 p.m. | W 4-1 [Detailed Results] | |
| Thu., 5/11 | V Girls Outdoor Track | Woodland, Watertown | Away - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Thu., 5/11 | V Softball | Kennedy | Home - Holy Cross-Alumni Field [Directions] | 5:00 p.m. | W 17-1 | |
| Thu., 5/11 | V Girls Tennis | Kennedy | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Fri., 5/12 | V Boys Lacrosse | Avon | Home - Holy Cross-Municipal Stadium [Directions] | 4:00 p.m. | W 11-9 | |
| Fri., 5/12 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Sat., 5/13 | JV Baseball | Wolcott | Away - Wolcott HS-Baseball Diamond [Directions] | 9:00 a.m. | L 6-5 | |
| Sat., 5/13 | V Boys Lacrosse | Somers | Home - Holy Cross-Municipal Stadium [Directions] | 11:00 a.m. | L 7-14 | |
| Sat., 5/13 | JV Softball | Woodland | Away - Wolcott HS-Softball Field [Directions] | 8:00 a.m. | ||
| Mon., 5/15 | V Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:45 p.m. | L 1-0 | |
| Mon., 5/15 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:30 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Torrington | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 3-2 | |
| Mon., 5/15 | V Softball | Seymour | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 1-5 | |
| Mon., 5/15 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 3:30 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/16 | JV Baseball | Seymour | Away - French Park-Baseball Field [Directions] | 3:45 p.m. | W 9-7 | |
| Tue., 5/16 | V Boys Golf | Oxford, Seymour | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | WCA | Home - Holy Cross-Holy Cross Track [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | WCA | Home - Holy Cross-Holy Cross Track [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Girls Tennis | Ansonia | Home - Holy Cross-Tennis Courts [Directions] | 2:30 p.m. | W 6-1 [Detailed Results] | |
| Wed., 5/17 | V Boys Golf | St. Paul Catholic, Watertown | Home - Western Hills Golf Course (Wtby) [Directions] | 2:15 p.m. | ||
| Wed., 5/17 | V Boys Lacrosse | Watertown | Home - Holy Cross-Municipal Stadium [Directions] | 6:00 p.m. | L 4-16 | |
| Wed., 5/17 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 2:30 p.m. | ||
| Wed., 5/17 | V Girls Tennis | Watertown | Home - Holy Cross-Tennis Courts [Directions] | 2:30 p.m. | W 4-3 [Detailed Results] | |
| Thu., 5/18 | JV Baseball | Kennedy | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Thu., 5/18 | V Softball | Pomperaug (Scrim.) | Away - Pomperaug HS-Softball Field [Directions] | 3:30 p.m. | ||
| Fri., 5/19 | V Girls Tennis | Wolcott | Home - Woodland Regional HS-Woodland regional HS [Directions] | 3:30 p.m. | W 4-3 [Detailed Results] | |
| Sat., 5/20 | V Boys Lacrosse | St. Paul Catholic | Home - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 5/20 | V Boys Outdoor Track | NVL Outdoor Track and Field Championship | Away - Naugatuck HS-Veterans Field | TBA | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/24, Time to 10:00 p.m. | ||||||
| Sat., 5/20 | V Girls Outdoor Track | NVL Outdoor Track and Field Championship | Away - Naugatuck HS-Veterans Field | TBA | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/24, Time to 10:00 a.m. | ||||||
| Mon., 5/22 | V Baseball | Torrington | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | ||
| Mon., 5/22 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 6:30 p.m. | W 16-7 | |
| Tue., 5/23 | JV Baseball | St. Paul Catholic | Home - Holy Cross-Alumni Field [Directions] | 4:30 p.m. | ||
| Tue., 5/23 | V Softball | Woodland | Away - Wolcott HS-Turf Field and Lower Field [Directions] | 5:00 p.m. | L 0-16 | |
| Thu., 5/25 | V Softball | Lewis Mills (Scrim.) | Home - Holy Cross-Alumni Field [Directions] | 4:30 p.m. | ||
| Fri., 5/26 | V Boys Lacrosse | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 5:30 p.m. | ||
| Fri., 5/26 | V Boys Tennis | Killingly | Home - Wilby HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Fri., 5/26 | V Softball | Plainville (Scrim.) | Home - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | ||
| Fri., 5/26 | V Girls Tennis | Ansonia | Home - Woodland HS-Tennis Courts [Directions] | 12:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 5/27 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 10:00 a.m. | ||
| Tue., 5/30 | V Baseball | Jonathan Law | Home - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 2:30 p.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class M Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class S Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Softball | Wright Tech | Home - Holy Cross HS-Softball Diamond [Directions] | 4:00 p.m. | W 16-0 | |
| Tue., 5/30 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 5/31 | V Softball | Stafford | Home - Holy Cross HS-Softball Diamond [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 6/1 | V Boys Golf | NVL Boys' Golf Championship | Away - Watertown Golf Club | 7:30 a.m. | ||
| Fri., 6/2 | V Softball | Coventry | Away - Coventry HS-Softball Diamond [Directions] | 3:00 p.m. | ||
| Sat., 6/3 | V Softball | Coventry | Away - Coventry HS-Softball Diamond [Directions] | 2:30 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Golf | CIAC Division III Championship | Away - Stanley GC | 8:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Sat., 6/10 | V Boys Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||