| Holy Cross 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 532 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 8/26 | V Football | Plainville, Watertown (Scrim.) | Away - Plainville HS-Plainville HS- Tinty Field and Track [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 8/28, Time to 10:00 a.m. | ||||||
| Wed., 9/1 | V Girls Soccer | Wilton (Scrim.) | Away - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | Cancelled | |
| Wed., 9/1 | JV Girls Soccer | Wilton (Scrim.) | Away - Allen's Meadow-2A [Directions] | Canceled | Cancelled | |
| Thu., 9/2 | V Boys Soccer | Seymour (Scrim.) | Away - Seymour HS-Seymour High Lower Field [Directions] | 4:00 p.m. | ||
| Thu., 9/2 | V Girls Soccer | St. Joseph (Scrim.) | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | ||
| Sat., 9/4 | V Boys Soccer | Kaynor Tech | Home - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 11:30 a.m. | ||
| Sat., 9/4 | V Girls Soccer | Granby Memorial, Avon, Coventry, Enfield, Notre Dame-Fairfield, Portland, Rocky Hill, Suffield, Wilton | Away - Granby Memorial HS-Stadium Field | 8:00 a.m. | ||
| Tue., 9/7 | V Girls Soccer | Brookfield (Scrim.) | Away - Brookfield HS-BHS Stadium Field [Directions] | 3:30 p.m. | ||
| Tue., 9/7 | JV Girls Soccer | Brookfield (Scrim.) | Away - Cadigan Field-Field #2 [Directions] | Canceled | Cancelled | |
| Wed., 9/8 | V Girls Volleyball | Pomperaug (Scrim.) | Away - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/8 | JV Girls Volleyball | Pomperaug | Away - Pomperaug HS-Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/9 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 3:30 p.m. | W 2-1 | |
| Fri., 9/10 | V Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 7:00 p.m. | W 34-18 | |
| Sat., 9/11 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:30 a.m. | ||
| Sat., 9/11 | V Boys Soccer | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 12:00 p.m. | T 0-0 | |
| Sat., 9/11 | JV Boys Soccer | Oxford | Away - Oxford HS-OHS Soccer Field-West [Directions] | 12:00 p.m. | ||
| Sat., 9/11 | V Girls Soccer | Oxford | Home - Holy Cross-Alumni Field [Directions] | 12:00 p.m. | W 7-3 | |
| Tue., 9/14 | V Boys Cross Country | Crosby, Derby, Kennedy | Home - Holy Cross [Directions] | 3:45 p.m. | Holy Cross 22 Derby 37 Holy Cross 15 Crosby 50 Derby 15 Crosby 50 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Tue., 9/14 | V Boys Soccer | St. Paul Catholic | Home - Holy Cross-Alumni Field [Directions] | 5:00 p.m. | W 6-1 | |
| Tue., 9/14 | JV Boys Soccer | St. Paul Catholic | Home - Upper Murray Park [Directions] | 5:00 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Crosby, Derby, Kennedy | Home - Holy Cross [Directions] | 3:45 p.m. | Holy Cross 15 Crosby 50 Derby 23 Holy Cross 33 Derby 15 Crosby 50 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Tue., 9/14 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/14 | V Girls Volleyball | Crosby | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 3-0 | |
| Tue., 9/14 | JV Girls Volleyball | Crosby | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 9/15 | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-Upper Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/16 | V Football | Kennedy | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:30 p.m. | W 35-14 | |
| Thu., 9/16 | V Girls Soccer | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/17 | V Boys Soccer | Wilby | Home - Holy Cross-Alumni Field [Directions] | 5:00 p.m. | W 7-0 | |
| Fri., 9/17 | V Girls Swimming and Diving | Kennedy | Away - John F. Kennedy HS-John Reardon Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/17 | V Girls Volleyball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 9/17 | JV Girls Volleyball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Sat., 9/18 | FM Football | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FR Girls Volleyball | Woodland, Naugatuck, Seymour | Away - Woodland HS-Gym [Directions] | 10:00 a.m. | ||
| Tue., 9/21 | V Boys Cross Country | Seymour, WCA, Wolcott | Away - Seymour HS-Seymour High Lower Field [Directions] | 3:30 p.m. | Holy Cross 19 Seymour 36 Holy Cross 15 Wolcott 50 Holy Cross 15 WCA 50 | |
| Tue., 9/21 | V Boys Soccer | Kennedy | Away - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 9-2 | |
| Tue., 9/21 | V Girls Cross Country | Seymour, WCA, Wolcott | Away - Seymour HS-Seymour High Lower Field [Directions] | 3:30 p.m. | Holy Cross 28 Wolcott 29 Holy Cross 24 Seymour 34 Holy Cross 19 WCA 44 | |
| Tue., 9/21 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/21 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/22 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:15 p.m. | ||||||
| Wed., 9/22 | JV Boys Soccer | Kennedy | Away - West Side MS-Waterbury-Soccer Field [Directions] | 3:30 p.m. | ||
| Wed., 9/22 | V Girls Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Wed., 9/22 | V Girls Soccer | Naugatuck | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 7-2 | |
| Thu., 9/23 | JV Girls Soccer | Wolcott | Away - Wolcott HS-Soccer Field [Directions] | 3:30 p.m. | ||
| Thu., 9/23 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 9/23 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | V Football | Ansonia | Away - Nolan Field-Ansonia-Football Field [Directions] | 7:00 p.m. | L 7-28 | |
| Fri., 9/24 | V Girls Volleyball | Oxford | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 3-1 | |
| Sat., 9/25 | JV Boys Soccer | Woodland | Home - Upper Murray Park [Directions] | 9:00 a.m. | ||
| Sat., 9/25 | V Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 9:30 a.m. | L 1-3 | |
| Sat., 9/25 | JV Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | Postponed | ||
| Sat., 9/25 | FR Girls Volleyball | Seymour, Torrington, Wolcott (Scrim.) | Away - Seymour HS-Gym [Directions] | 10:00 a.m. | ||
| Tue., 9/28 | V Boys Soccer | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 6:00 p.m. | W 9-0 | |
| Tue., 9/28 | V Girls Soccer | Watertown | Home - Municipal Stadium-Bethel HS Track & Field Training Center [Directions] | 7:15 p.m. | W 5-1 | |
| Tue., 9/28 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/28 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/29 | V Boys Cross Country | Naugatuck, Wilby, Woodland | Home - Holy Cross [Directions] | 3:45 p.m. | Woodland 19 Holy Cross 38 Holy Cross 24 Naugatuck 31 Holy Cross 15 Wilby 50 | |
| Wed., 9/29 | V Girls Cross Country | Naugatuck, Wilby, Woodland | Home - Holy Cross [Directions] | 3:45 p.m. | Woodland 21 Holy Cross 40 Holy Cross 24 Naugatuck 31 Holy Cross 15 Wilby 50 | |
| Thu., 9/30 | V Football | Crosby | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 2:30 p.m. | W 33-21 | |
| Thu., 9/30 | JV Boys Soccer | Seymour | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Thu., 9/30 | V Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 9/30 | JV Girls Volleyball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/1 | V Boys Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | 4:00 p.m. | ||
| Fri., 10/1 | V Boys Soccer | Seymour | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 6-2 | |
| Fri., 10/1 | V Girls Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 10/1 | V Girls Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/1 | V Girls Volleyball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/1 | JV Girls Volleyball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Sat., 10/2 | FM Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | V Boys Soccer | Immaculate | Home - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 6:30 p.m. | W 3-0 | |
| Sat., 10/2 | V Girls Soccer | Immaculate | Home - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 4:15 p.m. | L 3-4 | |
| Sat., 10/2 | FR Girls Volleyball | Naugatuck, Torrington, Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/4 | V Girls Volleyball | Housatonic Regional | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 10/4 | JV Girls Volleyball | Housatonic Regional | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:15 p.m. | ||
| Tue., 10/5 | V Boys Cross Country | Oxford, Torrington | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | Holy Cross 15 Oxford 50 Holy Cross19 Torrington 43 | |
| Tue., 10/5 | V Boys Soccer | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | W 5-0 | |
| Tue., 10/5 | JV Boys Soccer | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | Postponed | ||
| Tue., 10/5 | V Girls Cross Country | Oxford, Torrington | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | Holy Cross 15 Oxford 50 Holy Cross 15 Torrington 50 | |
| Tue., 10/5 | V Girls Volleyball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | L 2-3 | |
| Tue., 10/5 | JV Girls Volleyball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 10/6 | V Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | W 6-0 | |
| Thu., 10/7 | V Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 10/7 | V Girls Volleyball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 3:30 p.m. | L 1-3 | |
| Thu., 10/7 | JV Girls Volleyball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | Postponed | ||
| Fri., 10/8 | V Girls Soccer | Woodland | Home - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 5:15 p.m. | T 1-1 | |
| Fri., 10/8 | V Girls Volleyball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:15 p.m. | L 2-3 | |
| Fri., 10/8 | JV Girls Volleyball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 10/9 | V Football | Woodland | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 4:30 p.m. | W 40-28 | |
| Sat., 10/9 | JV Boys Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:30 a.m. | ||
| Tue., 10/12 | V Boys Cross Country | St. Paul Catholic, Watertown | Away - St. Paul Catholic HS-St. Paul Track [Directions] | 3:30 p.m. | Holy Cross 26 St. Paul 29 Holy Cross 25 Watertown 32 | |
| Tue., 10/12 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Ave [Directions] | 3:30 p.m. | W 7-0 | |
| Tue., 10/12 | V Girls Cross Country | St. Paul Catholic, Watertown | Away - St. Paul Catholic HS-St. Paul Track [Directions] | 3:30 p.m. | Holy Cross 20 St. Paul 39 Holy Cross 21 Watertown 40 | |
| Tue., 10/12 | V Girls Soccer | Ansonia | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 4-0 | |
| Tue., 10/12 | V Girls Volleyball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 10/12 | JV Girls Volleyball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 10/13 | V Boys Soccer | Woodland | Home - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | T 1-1 | |
| Thu., 10/14 | V Girls Soccer | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 6:00 p.m. | W 7-0 | |
| Thu., 10/14 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/14 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 10/15 | V Boys Soccer | Derby | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 6-1 | |
| Fri., 10/15 | V Girls Volleyball | Woodland | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | L 0-3 | |
| Fri., 10/15 | JV Girls Volleyball | Woodland | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 10/19 | JV Boys Soccer | Naugatuck | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Tue., 10/19 | V Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/19 | JV Girls Volleyball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 10/20 | V Girls Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:00 p.m. | W 4-2 | |
| Thu., 10/21 | V Football | Wilby | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:30 p.m. | W 46-12 | |
| Thu., 10/21 | JV Girls Soccer | Naugatuck | Away - Rotary Field-Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/21 | V Girls Volleyball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/21 | JV Girls Volleyball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Fri., 10/22 | FM Football | Wilby | Away - Wilby HS-Football Field [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 10/22 | V Girls Volleyball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/22 | JV Girls Volleyball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | ||
| Sat., 10/23 | V Boys Soccer | Brookfield | Home - Holy Cross-Alumni Field [Directions] | 12:00 p.m. | W 3-1 | |
| Mon., 10/25 | V Boys Soccer | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 6:00 p.m. | W 6-1 | |
| Mon., 10/25 | V Girls Soccer | Wolcott | Home - Municipal Stadium-Bethel HS Track & Field Training Center [Directions] | 7:15 p.m. | W 6-0 | |
| Mon., 10/25 | V Girls Volleyball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 0-3 | |
| Mon., 10/25 | JV Girls Volleyball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 10/26 | JV Boys Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | Rainout | ||
| Wed., 10/27 | V Boys Soccer | Watertown | Home - Municipal Stadium-Bethel HS Track & Field Training Center [Directions] | 6:30 p.m. | W 4-1 | |
| Wed., 10/27 | V Girls Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 5-0 | |
| Wed., 10/27 | V Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:00 p.m. | L 1-3 | |
| Wed., 10/27 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 10/28 | FM Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 5:30 p.m. | ||
| Thu., 10/28 | V Boys Soccer | Naugatuck | Home - Naugatuck HS-Veterans Field [Directions] | 3:00 p.m. | W 4-1 | |
| Thu., 10/28 | JV Boys Soccer | Watertown | Away - Watertown HS-Veteran's Park [Directions] | 3:30 p.m. | ||
| Fri., 10/29 | V Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 7:00 p.m. | L 14-24 | |
| Sat., 10/30 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 9:00 a.m. | L 0-3 | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class SS Championship | Away - Wickham Park | 3:10 p.m. | ||
| Mon., 11/1 | V Boys Soccer | Seymour | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class S Championship | Away - Wickham Park | 2:35 p.m. | ||
| Mon., 11/1 | V Girls Soccer | Wolcott | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 11/2 | V Boys Soccer | Naugatuck | Home - Torrington HS-Robert Frost Sports Complex [Directions] | 7:30 p.m. | ||
| Tue., 11/2 | JV Boys Soccer | Wolcott | Away - Wolcott HS-Wolcott High School, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 11/2 | V Girls Soccer | Watertown | Home - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 5:30 p.m. | W 2-1 | |
| Thu., 11/4 | V Boys Soccer | Watertown | Home - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 11/4 | V Girls Soccer | Woodland | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 7:30 p.m. | L 1-2 | |
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | W 42-12 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Seymour | Away - Seymour HS-turf field [Directions] | 10:00 a.m. | ||
| Mon., 11/8 | V Girls Soccer | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 11/8 | V Girls Volleyball | Weaver | Away - Weaver HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 11/10 | V Girls Soccer | East Granby | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 2:00 p.m. | W 2-0 | |
| Wed., 11/10 | V Girls Volleyball | Aerospace | Away - Academy of Aerospace and Engineering-Gym 1 [Directions] | 4:30 p.m. | ||
| Thu., 11/11 | V Boys Soccer | East Hampton | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 2:00 p.m. | ||
| Fri., 11/12 | V Girls Soccer | Thomaston | Home - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 4:00 p.m. | W 5-1 | |
| Fri., 11/12 | V Girls Volleyball | Griswold | Away - Griswold HS-GHS Gym [Directions] | 6:00 p.m. | ||
| Sat., 11/13 | FM Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 11/13 | FM Football | Ansonia | Home - Holy Cross [Directions] | Canceled | Cancelled | |
| Sat., 11/13 | V Boys Soccer | Canton | Home - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 2:00 p.m. | ||
| Tue., 11/16 | V Girls Soccer | Somers | Home - Veteran's Stadium-Willow Brook Park-New Britain HS [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 11/18 | V Football | Seymour | Home - Crosby HS-Jimmy Lee Stadium (turf) [Directions] | 6:30 p.m. | W 35-6 | |
| Sat., 11/20 | FM Football | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 11/20 | FM Football | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 10:00 a.m. | ||
| Sun., 11/21 | V Girls Soccer | Northwest Catholic | Home - Dillon Stadium [Directions] | 11:00 a.m. | W 3-2 | |
| Thu., 11/25 | V Football | Wolcott | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 10:00 a.m. | W 47-8 | |
| Tue., 11/30 | V Football | New Fairfield | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 6:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 10:00 a.m. | ||
| Sat., 12/4 | V Girls Ice Hockey | Masuk Coop (Scrim.) | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:30 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Sacred Heart Academy (Scrim.) | Away - Sacred Heart Academy-Gym [Directions] | 4:30 p.m. | Cancelled | |
| Wed., 12/8 | V Girls Ice Hockey | Guilford Coop (Scrim.) | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | ||
| Thu., 12/9 | V Boys Basketball | Pomperaug (Scrim.) | Home - Holy Cross-gym [Directions] | 5:00 p.m. | ||
| Thu., 12/9 | V Girls Basketball | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/10 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 4-3 | |
| Sat., 12/11 | V Boys Basketball | Windsor, Capital Prep, Cromwell, Crosby, Daniel Hand, East Hartford, Farmington, Fitch, New London, Norwich Free Academy, West Springfield (MA), Xavier | Away - Windsor HS-WHS Main Gym | 4:00 p.m. | ||
| Mon., 12/13 | V Boys Basketball | New Britain (Scrim.) | Home - Holy Cross-gym [Directions] | 4:00 p.m. | ||
| Mon., 12/13 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 12/14 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | W 60-6 | |
| Tue., 12/14 | JV Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/15 | V Girls Basketball | Mercy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 55-51 | |
| Wed., 12/15 | JV Girls Basketball | Mercy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/15 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | L 1-9 | |
| Thu., 12/16 | FR Boys Basketball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 12/17 | V Boys Basketball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 96-38 | |
| Fri., 12/17 | JV Boys Basketball | Torrington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 12/18 | FR Boys Basketball | Ansonia, Naugatuck, Oxford | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/18 | V Wrestling | Darien Invitational | Away - Darien HS-DHS Main Gym | Canceled | Cancelled | |
| Sat., 12/18 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 6:30 p.m. | W 9-3 | |
| Mon., 12/20 | FR Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Postponed | ||
| Tue., 12/21 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 7:00 p.m. | L 56-79 | |
| Tue., 12/21 | JV Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:30 p.m. | ||
| Tue., 12/21 | V Girls Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 76-18 | |
| Tue., 12/21 | JV Girls Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/22 | V Boys Basketball | Immaculate | Home - Holy Cross-gym [Directions] | 7:00 p.m. | W 75-64 | |
| Wed., 12/22 | JV Boys Basketball | Immaculate | Home - Holy Cross-gym [Directions] | 5:00 p.m. | ||
| Wed., 12/22 | FR Boys Basketball | Immaculate | Home - Holy Cross-gym [Directions] | 3:00 p.m. | ||
| Wed., 12/22 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena-Red Rink [Directions] | 5:00 p.m. | L 0-6 | |
| Thu., 12/23 | V Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 3:00 p.m. | W 81-69 | |
| Thu., 12/23 | JV Boys Basketball | Oxford | Away - Oxford HS-Main Gym [Directions] | 1:15 p.m. | ||
| Thu., 12/23 | JV Girls Basketball | Oxford | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 12/29 | V Girls Ice Hockey | Simsbury | Home - Hamden-Lou Astorino Ice Rink [Directions] | 10:00 a.m. | L 2-4 | |
| Thu., 12/30 | V Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:45 p.m. | W 65-57 | |
| Thu., 12/30 | JV Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/30 | FR Boys Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 3:15 p.m. | ||
| Thu., 12/30 | V Girls Basketball | Woodland | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 66-31 | |
| Thu., 12/30 | JV Girls Basketball | Woodland | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Tue., 1/4 | FR Boys Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Tue., 1/4 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:15 p.m. | L 2-3 | |
| Wed., 1/5 | V Boys Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 90-48 | |
| Wed., 1/5 | JV Boys Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/5 | V Wrestling | Gilbert/Torrington | Home - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | DOHC 30 Gilbert 12 | |
| Fri., 1/7 | JV Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 1/7 | FR Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 1/7 | JV Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 1/8 | V Boys Basketball | Newington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | W 95-55 | |
| Sat., 1/8 | JV Boys Basketball | Newington | Home - Holy Cross-gym [Directions] | 4:00 p.m. | ||
| Sat., 1/8 | FR Boys Basketball | Newington | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 2:00 p.m. | ||
| Sat., 1/8 | V Wrestling | TBA, Canton, East Lyme/Norwich Tech, TBA, Shelton, St. Joseph | Away - TBA | Postponed | ||
| Sat., 1/8 | V Girls Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 11:00 a.m. | W 69-24 | |
| Sat., 1/8 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 9:30 a.m. | ||
| Sat., 1/8 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Champions Skating Rink - Cromwell-Upper Rink [Directions] | 12:00 p.m. | L 2-5 | |
| Tue., 1/11 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 74-68 | |
| Tue., 1/11 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:15 p.m. | ||
| Tue., 1/11 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/11 | V Girls Basketball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 60-19 | |
| Tue., 1/11 | JV Girls Basketball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/12 | V Wrestling | Terryville-Thomaston | Home - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | DOHC 39 Terryville/Thomaston 18 | |
| Thu., 1/13 | V Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 89-59 | |
| Fri., 1/14 | FR Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 1/14 | V Girls Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 74-28 | |
| Fri., 1/14 | JV Girls Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 1/15 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 12:00 p.m. | L 68-89 | |
| Sat., 1/15 | JV Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 1/15 | V Wrestling | Darien, Bunnell, Weston | Away - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | DOHC 24 Darien 48 DOHC 18 Weston 60 DOHC 6 Bunnell 66 | |
| Sat., 1/15 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 1-5 | |
| Mon., 1/17 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 7:30 p.m. | L 2-5 | |
| Tue., 1/18 | V Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 7:00 p.m. | W 93-80 | |
| Tue., 1/18 | JV Boys Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | V Girls Basketball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 83-60 | |
| Tue., 1/18 | JV Girls Basketball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Girls Basketball | Seymour | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 1/19 | V Wrestling | Northwestern, St. Paul Catholic | Home - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | DOHC 36 Northwestern 12 DOHC 36 St.Paul 30 | |
| Wed., 1/19 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | W 7-5 | |
| Thu., 1/20 | V Girls Basketball | Windsor | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 81-54 | |
| Thu., 1/20 | JV Girls Basketball | Windsor | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:25 p.m. | ||
| Fri., 1/21 | V Boys Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 56-57 | |
| Fri., 1/21 | JV Boys Basketball | Kennedy | Home - Holy Cross-gym [Directions] | 5:15 p.m. | ||
| Sat., 1/22 | FR Boys Basketball | Kennedy | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/22 | V Wrestling | Morgan, Shelton | Home - Derby HS-DHS Vitello Gym [Directions] | 9:00 a.m. | DOHC 24 Shelton 48 DOHC 30 Morgan 42 | weigh in @ 8am |
| Sat., 1/22 | V Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 11:00 a.m. | W 79-23 | |
| Sat., 1/22 | JV Girls Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 1/22 | FR Girls Basketball | Seymour, St. Paul Catholic | Away - Seymour HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/22 | FR Girls Basketball | Seymour | Away - Seymour HS-Gym [Directions] | 11:30 a.m. | ||
| Sat., 1/22 | V Girls Ice Hockey | Conard | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:15 p.m. | L 1-6 | |
| Tue., 1/25 | V Boys Basketball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | L 53-69 | |
| Tue., 1/25 | JV Boys Basketball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/25 | FR Boys Basketball | Naugatuck | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:00 p.m. | W 80-44 | |
| Tue., 1/25 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/26 | V Girls Basketball | Wolcott | Away - Wolcott HS-John H. Morris Gymnasium [Directions] | 5:00 p.m. | W 72-47 | |
| Wed., 1/26 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | W 3-1 | |
| Thu., 1/27 | V Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | W 84-54 | |
| Thu., 1/27 | JV Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 1/27 | V Boys Swimming and Diving | Oxford | Home - Kennedy HS (Waterbury) [Directions] | 6:00 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Oxford | Home - Holy Cross-gym [Directions] | 6:00 p.m. | W 65-36 | |
| Fri., 1/28 | FR Boys Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Postponed | ||
| Fri., 1/28 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | Postponed | ||
| Sat., 1/29 | V Wrestling | Individuals Tourney | Away - Suffield HS | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 a.m. | ||||||
| Tue., 2/1 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 7:00 p.m. | W 79-67 | |
| Tue., 2/1 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic HS-Rev. Brian Monnerat Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Boys Swimming and Diving | Crosby/WCA | Home - Kennedy HS (Waterbury) [Directions] | 6:00 p.m. | ||
| Tue., 2/1 | V Girls Basketball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 73-53 | |
| Tue., 2/1 | JV Girls Basketball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/1 | FR Girls Basketball | St. Paul Catholic | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 2/2 | V Wrestling | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/2 | V Girls Ice Hockey | Suffield Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | L 0-3 | |
| Thu., 2/3 | V Girls Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:30 p.m. | W 72-18 | |
| Thu., 2/3 | JV Girls Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 2/3 | V Girls Ice Hockey | Guilford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:10 p.m. | L 1-7 | |
| Fri., 2/4 | JV Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | Postponed | ||
| Sat., 2/5 | FR Boys Basketball | Naugatuck, TBA | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 2/5 | V Wrestling | Stafford Wrestling Invitational | Away - Stafford HS-Gym | 9:15 a.m. | ||
| Sat., 2/5 | JV Girls Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | FR Girls Basketball | Wolcott | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 2/5 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 2/8 | V Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 7:00 p.m. | W 75-65 | |
| Tue., 2/8 | JV Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/8 | V Boys Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 4:00 p.m. | ||
| Tue., 2/8 | V Girls Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 79-31 | |
| Tue., 2/8 | JV Girls Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/9 | FR Boys Basketball | WCA | Away - Waterbury Career Academy-Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 2/9 | V Girls Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 5:00 p.m. | W 81-42 | |
| Wed., 2/9 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | L 3-4 | |
| Thu., 2/10 | V Boys Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 63-61 | |
| Thu., 2/10 | JV Boys Basketball | Crosby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 7:00 p.m. | W 63-61 | |
| Thu., 2/10 | JV Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | V Wrestling | Gilbert, Holy Cross, Berkshire League Tournament, Nonnewaug, Northwestern, Seymour, St. Paul Catholic, Terryville/Thomaston, Thomaston | Away - Gilbert School-Gym | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 2/12 | V Wrestling | Gilbert, Derby, Berkshire League Tournament, Nonnewaug, Northwestern, Seymour, St. Paul Catholic, Terryville/Thomaston, Thomaston | Away - Gilbert School-Gym | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 2/12 | FR Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | Postponed | ||
| Sat., 2/12 | V Girls Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 2-10 | |
| Sat., 2/12 | V Girls Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 80-49 | |
| Tue., 2/15 | JV Boys Basketball | Wilby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Watertown | Home - Kennedy HS (Waterbury) [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | V Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | W 66-20 | |
| Tue., 2/15 | JV Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Tue., 2/15 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Red Rink [Directions] | 4:25 p.m. | L 0-3 | |
| Wed., 2/16 | FR Boys Basketball | New Fairfield | Home - Holy Cross-gym [Directions] | 5:00 p.m. | ||
| Thu., 2/17 | FR Boys Basketball | WCA | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/17 | V Boys Swimming and Diving | Brookfield | Home - Kennedy HS (Waterbury) [Directions] | Postponed | ||
| Thu., 2/17 | V Girls Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 7:00 p.m. | W 76-52 | |
| Thu., 2/17 | JV Girls Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | V Boys Basketball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | W 91-58 | |
| Fri., 2/18 | JV Boys Basketball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/18 | V Wrestling | Class S Championship - Day 1 | Away - Killingly | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Boys Swimming and Diving | Kennedy, Seymour | Away - John F. Kennedy HS-JFK Pool [Directions] | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class S Championship - Day 2 | Away - Killingly | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Basketball | Ansonia | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:15 p.m. | ||
| Sat., 2/19 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-Red [Directions] | 2:30 p.m. | W 3-0 | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 2:00 p.m. | W 4-2 | |
| Tue., 2/22 | V Boys Basketball | Derby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | W 96-39 | |
| Tue., 2/22 | JV Boys Basketball | Derby | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | Canceled | Cancelled | |
| Tue., 2/22 | V Girls Basketball | Woodland | Home - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 7:30 p.m. | ||
| Wed., 2/23 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | ||
| Thu., 2/24 | FR Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 3:00 p.m. | ||
| Thu., 2/24 | V Girls Basketball | Seymour | Home - Kennedy HS (Waterbury) [Directions] | 7:00 p.m. | ||
| Thu., 2/24 | V Girls Basketball | Seymour | Home - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 7:00 p.m. | ||
| Sat., 2/26 | V Boys Basketball | WCA | Home - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 2:30 p.m. | ||
| Sat., 2/26 | V Boys Swimming and Diving | Woodland, Crosby/WCA, Kennedy, Naugatuck, Oxford, Seymour, Torrington, WCA, Watertown | Away - John F. Kennedy HS-John Reardon Pool | 12:00 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Wrestling | CIAC Girls Wrestling State Championship | Away - Floyd Little Athletic Center-Field House | TBA | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sun., 2/27 | V Wrestling | CIAC Girls Wrestling State Championship | Away - Floyd Little Athletic Center-Field House | 9:00 a.m. | ||
| Wed., 3/2 | V Girls Swimming and Diving | TBA, Crosby, Kennedy, TBA, Oxford, Seymour, Torrington, WCA, Watertown | Away - Watertown HS | 6:00 p.m. | ||
| Fri., 3/4 | V Girls Basketball | Watertown | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | ||
| Sat., 3/5 | V Boys Swimming and Diving | Woodland, Crosby/WCA, Kennedy, Naugatuck, Oxford, Seymour, Torrington, WCA, Watertown | Away - John F. Kennedy HS-John Reardon Pool | 11:00 a.m. | ||
| Tue., 3/8 | V Girls Basketball | New Fairfield | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 7:00 p.m. | ||
| Thu., 3/10 | V Boys Basketball | St. Joseph | Home - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 4:00 p.m. | ||
| Fri., 3/11 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:30 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Mon., 3/14 | V Girls Basketball | Valley Regional | Home - Maloney HS-Maloney Main Gym [Directions] | 7:45 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sun., 3/20 | V Girls Basketball | Bacon Academy | Home - Mohegan Sun Arena-Arena [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | V Baseball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Baseball Diamond [Directions] | 2:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Sat., 3/26 | V Softball | Norwalk (Scrim.) | Away - Norwalk HS-Ray Barry Field [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | JV Softball | Norwalk (Scrim.) | Away - Norwalk HS-Ray Barry Field [Directions] | 12:30 p.m. | ||
| Mon., 3/28 | V Baseball | Pomperaug (Scrim.) | Away - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Softball | Bethel (Scrim.) | Away - Bethel HS-Kisling Field [Directions] | 3:45 p.m. | ||
| Wed., 3/30 | V Baseball | Brookfield (Scrim.) | Home - Brookfield HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | New Fairfield (Scrim.) | Away - New Fairfield HS-Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Softball | Brookfield (Scrim.) | Away - Brookfield HS-BHS Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 4/2 | V Baseball | WCA | Away - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 12:00 p.m. | W 33-0 | |
| Sat., 4/2 | V Boys Lacrosse | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 4:30 p.m. | W 16-6 | |
| Sat., 4/2 | JV Boys Lacrosse | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 6:30 p.m. | ||
| Sat., 4/2 | V Boys Outdoor Track | Oxford, Wilby | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 11:00 a.m. | Holy Cross 123 Wilby 17 Holy Cross 96 Oxford 45 | |
| Sat., 4/2 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 10:00 a.m. | L 0-5 | |
| Sat., 4/2 | V Girls Outdoor Track | Oxford, Wilby | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 11:00 a.m. | HC 67 Oxford 54 HC 90 Wilby 14 | |
| Sat., 4/2 | V Softball | WCA | Away - Municipal Stadium-Joan Joyce Softball Diamond [Directions] | 12:00 p.m. | W 32-7 | |
| Sat., 4/2 | V Girls Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 10:00 a.m. | W 5-2 | |
| Mon., 4/4 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 3:00 p.m. | W 4-1 | |
| Mon., 4/4 | V Boys Tennis | Naugatuck | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 2-3 | |
| Mon., 4/4 | V Softball | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:30 p.m. | W 18-3 | |
| Tue., 4/5 | V Baseball | Crosby | Home - Bucks Hill (MONTOE) Park-Baseball Field [Directions] | 4:00 p.m. | W 14-2 | |
| Tue., 4/5 | V Girls Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Wed., 4/6 | V Boys Tennis | Crosby | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | Cancelled | |
| Thu., 4/7 | V Softball | Crosby | Away - Municipal Stadium (Waterbury, CT)-Joan Joyce Softball Diamond [Directions] | 3:45 p.m. | W 12-0 | |
| Fri., 4/8 | V Baseball | Derby | Away - Payden Park [Directions] | 5:30 p.m. | W 17-3 | |
| Fri., 4/8 | V Boys Lacrosse | St. Paul Catholic | Away - Bristol Central HS-BC Turf Field [Directions] | 6:00 p.m. | L 11-14 | |
| Fri., 4/8 | V Boys Tennis | Pomperaug | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Mon., 4/11 | V Baseball | Torrington | Home - Bucks Hill (MONTOE) Park-Baseball Field [Directions] | 3:30 p.m. | L 8-6 | |
| Mon., 4/11 | V Boys Tennis | Torrington | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 1-4 | |
| Mon., 4/11 | V Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-varsity field [Directions] | 3:45 p.m. | L 1-8 | |
| Mon., 4/11 | V Girls Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Tue., 4/12 | JV Baseball | Torrington | Home - Waterville Park-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Tue., 4/12 | V Boys Outdoor Track | Crosby, Naugatuck | Home - Naugatuck HS-Veterans Field [Directions] | 4:45 p.m. | Holy Cross 104 Crosby 37 Naugatuck 105 Holy Cross 44 | |
| Tue., 4/12 | V Girls Outdoor Track | Crosby, Naugatuck | Home - Naugatuck HS-Veterans Field [Directions] | 4:45 p.m. | HC 11 Naug 122 HC 69 Crosby 62 | |
| Tue., 4/12 | JV Softball | Torrington | Away - Torrington HS Varsity Ladies Softball-THS Varsity Ladies Softball [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Baseball | Kennedy | Away - John F. Kennedy HS-Waterville Park [Directions] | 3:45 p.m. | W 16-2 | |
| Wed., 4/13 | V Boys Golf | Torrington | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Brodeur-46,Schiavone-50,McGerrity-53,Petrokaitis-75 | |
| Wed., 4/13 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 4/13 | V Softball | Kennedy | Home - Kennedy HS (Waterbury)-softball field [Directions] | 3:30 p.m. | W 24-1 | |
| Wed., 4/13 | V Girls Tennis | Kennedy | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 4/14 | JV Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 12:00 p.m. | ||
| Thu., 4/14 | V Softball | Derby | Home - Municipal Stadium Complex-Joan Joyce Diamond [Directions] | 10:00 a.m. | W 18-4 | |
| Thu., 4/14 | V Girls Tennis | Ansonia | Away - Nolan Field-Ansonia-Nolan Field- Tennis Courts [Directions] | 3:00 p.m. | W 7-0 | |
| Sat., 4/16 | V Baseball | Oxford | Home - Holy Cross-Alumni Field [Directions] | 12:00 p.m. | L 3-7 | |
| Sat., 4/16 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 10:00 a.m. | L 2-15 | |
| Mon., 4/18 | V Baseball | Wilby | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 28-0 | |
| Mon., 4/18 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Monroe Field [Directions] | 4:00 p.m. | W 20-6 | |
| Mon., 4/18 | V Softball | Wilby | Away - Bucks Hill Park #1-Bucks Hill Park [Directions] | 3:45 p.m. | W 22-3 | |
| Tue., 4/19 | V Boys Outdoor Track | Watertown, Woodland | Away - Watertown HS [Directions] | 3:45 p.m. | Holy Cross 93 Watertown 57 Woodland 94.5 Holy Cross 55.5 | |
| Tue., 4/19 | V Girls Outdoor Track | Watertown, Woodland | Away - Watertown HS [Directions] | 3:45 p.m. | HC 41 Watertown 90 HC 12 Woodland 137 | |
| Wed., 4/20 | V Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 3:30 p.m. | W 13-0 | |
| Wed., 4/20 | V Boys Tennis | Crosby | Away - Crosby HS-CHS Tennis. Courts [Directions] | 3:30 p.m. | Cancelled | |
| Wed., 4/20 | V Softball | Crosby | Home - Municipal Stadium Complex-Joan Joyce Diamond [Directions] | 3:30 p.m. | W 17-0 | |
| Wed., 4/20 | V Girls Tennis | Crosby | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 4/21 | V Boys Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 10-13 | |
| Thu., 4/21 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 5-2 | |
| Fri., 4/22 | V Baseball | WCA | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 22-1 | |
| Fri., 4/22 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Fri., 4/22 | V Softball | WCA | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 14-2 | |
| Sat., 4/23 | V Boys Lacrosse | Capital Prep | Away - Quirk MS-Soccer Field [Directions] | 3:00 p.m. | W 18-7 | |
| Sat., 4/23 | JV Softball | WCA | Home - Holy Cross-Alumni Field [Directions] | 10:00 a.m. | ||
| Mon., 4/25 | V Baseball | Cheshire | Away - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 8-5 | |
| Mon., 4/25 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:00 p.m. | Schiavone-42, McGarrity-46, Palladino-49, Brodeur-52 | |
| Mon., 4/25 | V Boys Tennis | Woodland | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Wed., 4/27 | V Baseball | Wolcott | Home - Holy Cross-Alumni Field [Directions] | 4:00 p.m. | L 2-6 | |
| Wed., 4/27 | V Boys Golf | Seymour | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Palladino-44, Schiavone-47, Shaker-48, Mason-49 | |
| Wed., 4/27 | V Boys Lacrosse | Watertown | Home - Municipal Stadium Complex-Bethel HS Track & Field Training Center [Directions] | 4:00 p.m. | L 7-15 | |
| Wed., 4/27 | V Boys Outdoor Track | Torrington, St. Paul Catholic | Away - Torrington HS [Directions] | 4:15 p.m. | Holy Cross 107.5 Torrington 42.5; Holy Cross 98 St. Paul 51 | |
| Wed., 4/27 | V Boys Tennis | Wolcott | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | L 1-4 | |
| Wed., 4/27 | V Girls Outdoor Track | Torrington, St. Paul Catholic | Away - Torrington HS [Directions] | 4:15 p.m. | HC 103 SP 33 HC 75 Torrington 70 | |
| Wed., 4/27 | V Softball | Wolcott | Away - Wolcott HS-George Babcock Softball Field [Directions] | 3:45 p.m. | L 4-11 | |
| Wed., 4/27 | V Girls Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 3:30 p.m. | W 5-2 | |
| Thu., 4/28 | V Boys Golf | St. Paul Catholic | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Palladino-48, Shaker-48, Schiavone-50, McGarrity-56 | |
| Thu., 4/28 | JV Softball | Wolcott | Away - Wolcott HS-JV Softball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/29 | V Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 4/29 | V Boys Tennis | Woodland | Away - Woodland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/29 | V Softball | Woodland | Home - Holy Cross-Alumni Field [Directions] | 3:00 p.m. | L 0-15 | |
| Fri., 4/29 | V Girls Tennis | Woodland | Home - Holy Cross-Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Sat., 4/30 | JV Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 11:30 a.m. | ||
| Sat., 4/30 | FR Baseball | Woodland | Away - Woodland HS-Baseball Diamond [Directions] | 9:30 a.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Somers | Away - Somers HS-Somers High School Turf Field [Directions] | 12:00 p.m. | L 6-20 | |
| Sat., 4/30 | JV Boys Lacrosse | Somers | Away - Somers HS-Somers High School Turf Field [Directions] | 1:30 p.m. | ||
| Sat., 4/30 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 11:00 a.m. | ||
| Sat., 4/30 | JV Girls Tennis | JV Girls Tennis Tournament | Away - Nonnewaug HS-Tennis Courts | 9:00 a.m. | ||
| Mon., 5/2 | V Baseball | Nonnewaug | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 4-7 | |
| Mon., 5/2 | V Boys Golf | Watertown | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Schiavone-45, Shaker-46 McGarrity-50, Palladino-52 | |
| Mon., 5/2 | V Boys Lacrosse | Capital Prep | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 4:00 p.m. | W 24-1 | |
| Mon., 5/2 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 9-13 | |
| Tue., 5/3 | V Boys Golf | Wolcott | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Shaker-44, Palladino-48, Brodeur-48, Schiavone-49 | |
| Tue., 5/3 | JV Softball | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Girls Tennis | St. Paul Catholic | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Wed., 5/4 | FR Baseball | St. Paul Catholic | Away - Page Park-Baseball Diamond [Directions] | Postponed | ||
| Wed., 5/4 | V Boys Lacrosse | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | 6:00 p.m. | W 16-1 | |
| Wed., 5/4 | V Boys Outdoor Track | Seymour, Kennedy | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:45 p.m. | Holy Cross 90 Seymour 60 Holy Cross 91 Kennedy 55 | |
| Wed., 5/4 | V Girls Outdoor Track | Seymour, Kennedy | Away - Seymour HS-Seymour High School Turf Field [Directions] | 3:45 p.m. | HC 49 Seymour 104 HC 94 Kennedy 41 | |
| Wed., 5/4 | V Softball | St. Paul Catholic | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 6:30 p.m. | W 19-1 | |
| Thu., 5/5 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/5 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | Palladino-45, Shaker-45, Schiavone-46, McGarrity-54 | |
| Thu., 5/5 | V Boys Lacrosse | Wolcott | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 5:15 p.m. | W 17-5 | |
| Sat., 5/7 | V Boys Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Mon., 5/9 | V Boys Golf | Wolcott | Away - Farmingbury Golf Course [Directions] | 2:30 p.m. | Palladino-40, Schiavone-41, Shaker-43, Mason-49 | |
| Mon., 5/9 | V Boys Lacrosse | Bethel | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 3:45 p.m. | L 11-12(OT) | |
| Mon., 5/9 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 5/9 | V Boys Tennis | Wilby | Away - Wilby HS-Dave Krill Tennis Courts at WHS [Directions] | 4:30 p.m. | W 4-1 | |
| Mon., 5/9 | V Softball | Wilby | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 19-1 | |
| Mon., 5/9 | V Girls Tennis | Wilby | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Tue., 5/10 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 4:00 p.m. | L 1-11 | |
| Tue., 5/10 | V Boys Outdoor Track | Wolcott, Derby | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 3:30 p.m. | Holy Cross 98 Wolcott 51 Derby 83 Holy Cross 66 | |
| Tue., 5/10 | V Boys Tennis | Watertown | Home - Wilby HS [Directions] | 3:30 p.m. | L 0-5 | |
| Tue., 5/10 | V Girls Outdoor Track | Wolcott, Derby | Away - Wolcott HS-Monroe Field and Lower Field [Directions] | 3:30 p.m. | HC 86 Wolcott 47 HC 58 Derby 92 | |
| Tue., 5/10 | JV Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/11 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 6:00 p.m. | W 8-7 | |
| Wed., 5/11 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:45 p.m. | ||
| Wed., 5/11 | V Boys Golf | Naugatuck | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Palladino-43, Mason-47, Schiavone-50, Brodeur-50 | |
| Wed., 5/11 | V Boys Golf | Waterbury Coop | Away - John F. Kennedy HS-Western Hills Golf Course [Directions] | 2:30 p.m. | Palladino-43, Mason-47 Schiavone-50, Brodeur-50 | |
| Wed., 5/11 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Wed., 5/11 | V Softball | Naugatuck | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | L 5-19 | |
| Wed., 5/11 | V Girls Tennis | Naugatuck | Home - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 5-2 | |
| Thu., 5/12 | V Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | W 18-1 | |
| Thu., 5/12 | JV Baseball | Naugatuck | Home - Holy Cross-Alumni Field [Directions] | 3:45 p.m. | ||
| Thu., 5/12 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 8-15 | |
| Thu., 5/12 | V Boys Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 1:30 p.m. | L 2-3 | |
| Thu., 5/12 | V Softball | Kennedy | Away - J F Kennedy HS Turf-Kennedy Turf field [Directions] | 3:45 p.m. | W 14-0 | |
| Thu., 5/12 | V Girls Tennis | Kennedy | Away - John F. Kennedy HS-Tennis Courts [Directions] | 2:00 p.m. | W 5-2 | |
| Thu., 5/12 | V Girls Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 5/13 | V Baseball | Kennedy | Home - Holy Cross-Alumni Field [Directions] | 2:30 p.m. | W 13-4 | |
| Sat., 5/14 | V Boys Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 10:00 a.m. | W 16-8 | |
| Mon., 5/16 | V Baseball | Seymour | Home - Holy Cross-Alumni Field [Directions] | 3:00 p.m. | L 3-2 | |
| Mon., 5/16 | V Boys Golf | Woodland | Home - Western Hills Golf Course (Wtby) [Directions] | 2:30 p.m. | Schiavone-42, Palladino-46, Mason-49, Shaker-49 | |
| Mon., 5/16 | V Boys Lacrosse | St. Paul Catholic | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | L 5-14 | |
| Mon., 5/16 | V Boys Tennis | Torrington | Away - Torrington HS-Tennis Courts [Directions] | 3:30 p.m. | L 0-5 | |
| Mon., 5/16 | V Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | 3:00 p.m. | L 2-10 | |
| Mon., 5/16 | JV Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 5/16 | V Girls Tennis | Seymour | Away - Seymour HS-Tennis [Directions] | 3:30 p.m. | W 5-2 | |
| Tue., 5/17 | V Boys Golf | Seymour | Away - Seymour HS-Oxford Greens [Directions] | 2:00 p.m. | Schiavone-47, Palladino-51, Brodeur-53, Mason-56 | |
| Tue., 5/17 | V Boys Outdoor Track | WCA | Home - Naugatuck HS-Raymond Legenza Field [Directions] | 3:00 p.m. | Holy Cross 88 WCA 58 | |
| Tue., 5/17 | V Boys Tennis | Watertown | Home - Wilby HS [Directions] | 3:30 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | WCA | Home - Naugatuck HS-Raymond Legenza Field [Directions] | 3:00 p.m. | HC 85 WCA 56 | |
| Tue., 5/17 | V Softball | Watertown | Away - Watertown High-Softball Field [Directions] | 5:30 p.m. | L 6-9 | |
| Wed., 5/18 | V Baseball | Watertown | Home - Holy Cross-Alumni Field [Directions] | 3:30 p.m. | W 11-0 | |
| Wed., 5/18 | V Boys Golf | Watertown | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 2:30 p.m. | Palladino-41, Mason-48, McGarrity-50, Brodeur-54 | |
| Wed., 5/18 | V Girls Tennis | St. Paul Catholic | Home - Holy Cross-Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 5/19 | JV Baseball | Nonnewaug | Home - Holy Cross-Alumni Field [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | V Boys Golf | St. Paul Catholic | Away - Chippanee Country Club [Directions] | 2:45 p.m. | McGarrity-41, Mason-43, Palladino-48, Shaker-48 | |
| Thu., 5/19 | V Boys Lacrosse | Ellington | Away - Ellington HS-Main Field [Directions] | 3:00 p.m. | L 6-11 | |
| Thu., 5/19 | JV Boys Lacrosse | Ellington | Away - Ellington HS-Main Field [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | JV Softball | Seymour | Away - Seymour HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 5/20 | V Softball | Immaculate | Away - Immaculate HS-Softball Diamond [Directions] | 3:00 p.m. | L 0-12 | |
| Fri., 5/20 | V Girls Tennis | Woodland | Home - Holy Cross-Tennis Courts [Directions] | 2:00 p.m. | ||
| Sat., 5/21 | V Baseball | Torrington | Home - Municipal Stadium Complex-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 11:00 a.m. | W 3-1 | |
| Sat., 5/21 | JV Baseball | Cheshire | Home - Holy Cross-Alumni Field [Directions] | Canceled | Cancelled | |
| Sat., 5/21 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 11:00 a.m. | ||
| Mon., 5/23 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | Mcgarrity-41, Shaker-42. Palladino-45, Schiavone-47 | |
| Mon., 5/23 | V Boys Lacrosse | Avon | Away - Avon HS-Turf Field [Directions] | 4:30 p.m. | L 3-18 | |
| Mon., 5/23 | V Girls Tennis | NVL Girls Tennis Individual Tournament | Away - Woodland HS-Tennis Courts | 12:00 p.m. | ||
| Tue., 5/24 | V Baseball | Oxford | Home - Municipal stadium [Directions] | 7:00 p.m. | ||
| Wed., 5/25 | V Boys Golf | Waterbury Coop | Home - Western Hills Golf Course (Wtby) [Directions] | 1:30 p.m. | Schiavone-43, McGerrity-46, Mason 49, Palladino-50 | |
| Wed., 5/25 | JV Boys Lacrosse | Nonnewaug | Home - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Softball | Pomperaug (Scrim.) | Away - Pomperaug HS-Softball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/27 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:30 p.m. | ||
| Fri., 5/27 | V Softball | Watertown (Scrim.) | Away - Watertown High-Softball Field [Directions] | 5:00 p.m. | ||
| Tue., 5/31 | V Baseball | SMSA | Home - Municipal Stadium Complex-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Softball | East Windsor | Away - East Windsor Senior HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Tennis | St. Paul Catholic | Home - Holy Cross-Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 6/1 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Somers | Away - Somers HS-Somers High School Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 6/2 | V Girls Tennis | Granby Memorial | Home - Holy Cross [Directions] | 12:00 p.m. | ||
| Fri., 6/3 | V Girls Tennis | Westbrook | Home - Tennis Club of Trumbull-Gym 1 [Directions] | 11:30 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Golf | CIAC Division III Spring Championship | Away - Fairview Farms | 8:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||