| Holy Cross 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 634 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:15pm | |
| TBA | JV Baseball | Seymour | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | Wolcott | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | Wilby | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | ||
| TBA | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | Cancelled | 2:15pm | |
| TBA | FR Baseball | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | ||
| TBA | FR Baseball | Seymour | Home - Upper Murray Park [Directions] | TBA | ||
| TBA | FR Baseball | Kennedy | Home - Upper Murray Park [Directions] | TBA | ||
| TBA | FR Boys Basketball | Wilby | Home - Tim McDonald Gymnasium [Directions] | TBA | ||
| TBA | V Boys Golf | Notre Dame-West Haven | Home - Waterbury CC [Directions] | Cancelled | ||
| TBA | JV Boys Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | TBA | ||
| TBA | JV Boys Soccer | Crosby | Home - Lower Murray Park [Directions] | Cancelled | ||
| TBA | JV Boys Soccer | Ansonia | Home - Lower Murray Park [Directions] | Cancelled | ||
| TBA | JV Boys Soccer | Wilby | Home - Lower Murray Park [Directions] | Cancelled | ||
| TBA | JV Boys Soccer | Seymour | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Boys Soccer | Kennedy | Away - West Side Middle School [Directions] | TBA | ||
| TBA | JV Boys Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | TBA | 2:30pm | |
| TBA | FR Boys Soccer | Masuk | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | TBA | no bus | |
| TBA | FR Girls Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 3:30 p.m. | 2:30pm | |
| TBA | FR Girls Basketball | Brookfield | Home - Holy Cross HS [Directions] | TBA | ||
| TBA | FR Girls Basketball | Torrington | Away - Torrington High School [Directions] | TBA | 2:15pm | |
| TBA | JV Girls Ice Hockey | Daniel Hand Coop | Away [Directions] | Cancelled | ||
| TBA | JV Girls Soccer | Wolcott | Away - Wolcott High School, Lower Soccer Field [Directions] | 3:30 p.m. | 2:30pm | |
| TBA | JV Girls Soccer | Seymour | Away - Seymour High Lower Field [Directions] | 3:45 p.m. | 2:30pm | |
| TBA | JV Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Girls Soccer | Watertown | Away - Veterans Park [Directions] | TBA | 2:30pm | |
| TBA | JV Girls Soccer | Oxford | Home - Upper Murray Park [Directions] | TBA | ||
| TBA | FR Girls Soccer | New Milford | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| TBA | FR Girls Soccer | Masuk | Away - Masuk Middle Field [Directions] | 4:00 p.m. | 2:30pm | |
| TBA | FR Girls Soccer | New Milford | Away - New Milford High School [Directions] | TBA | 2:15pm | |
| TBA | JV Softball | Torrington | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| TBA | JV Softball | Seymour | Away - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | Kennedy | Away - Huntington Park [Directions] | TBA | ||
| TBA | JV Softball | Sacred Heart | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Softball | Kennedy | Home - Lower Murray Park [Directions] | TBA | ||
| Tue., 9/9 | V Boys Cross Country | Mercy Invitational | Away - Mercy HS | 3:30 p.m. | 2:15pm | |
| Tue., 9/9 | V Girls Cross Country | Mercy Invitational | Away - Mercy HS | 3:30 p.m. | ||
| Tue., 9/9 | V Girls Soccer | Sacred Heart | Away - Hamilton Park | W 7-1 | 2:30pm | |
| Tue., 9/9 | V Girls Swimming and Diving | Berlin | Home - Kennedy HS [Directions] | Berlin 90 HC 87 | ||
| Tue., 9/9 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 3-1 | 2:30pm | |
| Tue., 9/9 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 4:45 p.m. | ||
| Wed., 9/10 | FR Football | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:15pm | |
| Thu., 9/11 | V Football | Wilby | Home - Municipal Stadium (Wtby) [Directions] | W 34-6 | 4:30pm | 2 buses- One Way |
| Thu., 9/11 | V Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | W 6-1 | 2:30pm | |
| Thu., 9/11 | V Girls Soccer | Woodland | Home - Holy Cross HS [Directions] | W 1-0 | ||
| Fri., 9/12 | JV Boys Soccer | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | 2:30pm | |
| Fri., 9/12 | JV Girls Soccer | Woodland | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 9/12 | V Girls Volleyball | Naugatuck | Home - Holy Cross HS [Directions] | L 0-3 | ||
| Fri., 9/12 | JV Girls Volleyball | Naugatuck | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Sat., 9/13 | JV Football | Wilby | Away - Wilby H.S. [Directions] | 10:00 a.m. | 8:30am | |
| Sat., 9/13 | JV Girls Soccer | Sacred Heart | Home - Upper Murray Park [Directions] | 10:00 a.m. | 2:30pm | |
| Tue., 9/16 | V Boys Cross Country | Woodland, Kennedy, Wolcott, Oxford | Away - WRHS [Directions] | Wood 22 HC 43 Wol 28 HC 29 HC 27 Kenn 29 HC 26 Ox 29 | 2:15pm | |
| Tue., 9/16 | V Boys Soccer | Wilby | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Tue., 9/16 | V Girls Cross Country | Woodland, Kennedy, Wolcott, Oxford | Away - WRHS [Directions] | Wood 15 HC 45 Ox 23 HC 32 HC 17 Wol 45 HC 15 Ken 45 | ||
| Tue., 9/16 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 6-1 | 2:15pm | |
| Tue., 9/16 | V Girls Swimming and Diving | Woodland | Away - Woodland High School Pool [Directions] | Woodland 96 HC 78 | 2:30pm | |
| Tue., 9/16 | V Girls Volleyball | Seymour | Home - Holy Cross HS [Directions] | L 0-3 | ||
| Tue., 9/16 | JV Girls Volleyball | Seymour | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 9/17 | JV Boys Soccer | Wilby | Home - Upper Murray Park [Directions] | Cancelled | ||
| Wed., 9/17 | FR Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:30pm | |
| Wed., 9/17 | V Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | L 2-3 | 2:30pm | |
| Wed., 9/17 | JV Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | 4:30 p.m. | ||
| Thu., 9/18 | FR Football | Sacred Heart | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Thu., 9/18 | FR Boys Soccer | Naugatuck | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Thu., 9/18 | V Girls Volleyball | Lewis Mills | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Thu., 9/18 | JV Girls Volleyball | Lewis Mills | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Fri., 9/19 | V Football | Sacred Heart | Away - Municipal Stadium | W 47-6 | 5:40pm | 2 buses- One Way |
| Fri., 9/19 | V Boys Soccer | Crosby | Home - Holy Cross HS [Directions] | W 4-1 | ||
| Sat., 9/20 | JV Football | Sacred Heart | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 9/20 | FR Boys Soccer | Masuk | Away - Masuk Middle Field [Directions] | 9:00 a.m. | 7:45am | |
| Sat., 9/20 | V Girls Soccer | East Hampton | Home - Holy Cross HS [Directions] | W 2-0 | ||
| Sat., 9/20 | FR Girls Soccer | Masuk | Home - Upper Murray Park [Directions] | 9:00 a.m. | ||
| Mon., 9/22 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | L 5-3 (OT) | 4:30pm | |
| Mon., 9/22 | V Girls Soccer | Watertown | Home - Municipal Stadium (Wtby) [Directions] | W 4-2 | ||
| Mon., 9/22 | V Girls Swimming and Diving | Seymour | Away - Seymour High School [Directions] | Seymour 89 HC 66 | 2:30pm | |
| Tue., 9/23 | V Boys Cross Country | Watertown, Derby, Kennedy | Away - Veterans Park [Directions] | Watertown 25 HC 34 HC 25 Derby 30 | 2:15pm | |
| Tue., 9/23 | JV Boys Soccer | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 2:30pm | |
| Tue., 9/23 | V Girls Cross Country | Watertown, Derby, Kennedy | Away - Veterans Park [Directions] | Watertown 15 HC 47 Derby 17 HC 39 | ||
| Tue., 9/23 | JV Girls Soccer | Watertown | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Tue., 9/23 | V Girls Volleyball | St. Paul Catholic | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Tue., 9/23 | JV Girls Volleyball | St. Paul Catholic | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 9/24 | V Boys Soccer | Sacred Heart | Away - Bucks Hill Park | W 2-1 | 2:30pm | |
| Wed., 9/24 | V Girls Soccer | Sacred Heart | Home - Holy Cross HS [Directions] | W 8-1 | ||
| Thu., 9/25 | FR Football | Naugatuck | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Thu., 9/25 | JV Boys Soccer | Sacred Heart | Away - Bucks Hill Park | 3:45 p.m. | 2:30pm | |
| Thu., 9/25 | JV Girls Soccer | Sacred Heart | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Thu., 9/25 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 0-3 | 2:30pm | |
| Thu., 9/25 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | ||
| Fri., 9/26 | V Football | Naugatuck | Away - Naugatuck High School [Directions] | L 7-42 | 5:30pm | 2 buses |
| Fri., 9/26 | V Boys Soccer | Ansonia | Home - Holy Cross HS [Directions] | W 1-0 | ||
| Fri., 9/26 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | W 7-1 | 2:30pm | |
| Fri., 9/26 | V Girls Swimming and Diving | Torrington | Home - Kennedy HS [Directions] | Torr 98 HC 89 | ||
| Fri., 9/26 | V Girls Volleyball | Wilby | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Fri., 9/26 | JV Girls Volleyball | Wilby | Home - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Sat., 9/27 | JV Football | Naugatuck | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 9/27 | FR Boys Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 9:00 a.m. | 7:45am | |
| Sat., 9/27 | FR Girls Soccer | Newtown | Home - Upper Murray Park [Directions] | 9:00 a.m. | ||
| Mon., 9/29 | V Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | W 2-0 | 2:30pm | |
| Mon., 9/29 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | T 1-1 | 4:45pm | |
| Tue., 9/30 | V Boys Cross Country | St. Paul Catholic, Naugatuck, Wilby, Kennedy | Home - Holy Cross HS [Directions] | Naugatuck 16 HC 44 HC 22 St Paul 34 HC 18 Wilby 45 | ||
| Tue., 9/30 | FR Boys Soccer | New Milford | Away - New Milford High School [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 9/30 | V Girls Cross Country | St. Paul Catholic, Naugatuck, Wilby, Kennedy | Home - Holy Cross HS [Directions] | Naugatuck 25 HC 30 HC 28 St Paul 29 HC 20 Wilby 37 | ||
| Tue., 9/30 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | H-K 91 HC 79 | 2:15pm | |
| Tue., 9/30 | V Girls Volleyball | Woodland | Home - Holy Cross HS [Directions] | L 2-3 | ||
| Tue., 9/30 | JV Girls Volleyball | Woodland | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 10/1 | FR Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 3:45 p.m. | 2:30pm | |
| Thu., 10/2 | V Boys Soccer | Seymour | Home - Holy Cross HS [Directions] | L 2-1 | ||
| Thu., 10/2 | V Girls Soccer | Seymour | Away - Seymour High Main Field [Directions] | W 3-0 | 4:45pm | |
| Thu., 10/2 | V Girls Volleyball | Seymour | Away - Seymour High School [Directions] | L 0-3 | 2:30pm | |
| Thu., 10/2 | JV Girls Volleyball | Seymour | Away - Seymour High School [Directions] | 4:45 p.m. | ||
| Fri., 10/3 | V Boys Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS | 3:45 p.m. | ||
| Fri., 10/3 | V Football | Oxford | Home - Municipal Stadium (Wtby) [Directions] | W 28-6 | 5:40pm | 2 buses- One Way |
| Fri., 10/3 | V Girls Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS | 3:45 p.m. | 2:00pm | |
| Fri., 10/3 | V Girls Soccer | Wolcott | Home - Holy Cross HS [Directions] | W 6-2 | ||
| Fri., 10/3 | V Girls Swimming and Diving | Suffield | Away - Windsor Locks High School [Directions] | Suffield 91 HC 83 | 2:15pm | |
| Fri., 10/3 | V Girls Volleyball | Crosby | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Fri., 10/3 | JV Girls Volleyball | Crosby | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Sat., 10/4 | JV Girls Soccer | Wolcott | Home - Upper Murray Park [Directions] | 10:00 a.m. | ||
| Mon., 10/6 | V Boys Soccer | Sacred Heart | Home - Municipal Stadium (Wtby) [Directions] | W 4-1 | ||
| Mon., 10/6 | JV Boys Soccer | Sacred Heart | Home - Lower Murray Park [Directions] | Cancelled | ||
| Tue., 10/7 | V Boys Cross Country | Sacred Heart, Torrington, Seymour, Crosby | Away - Montoe Park | HC 20 Torrington 41 HC 17 Seymour 39 HC 15 SHHS 48 HC 18 Crosby 42 | 2:15pm | |
| Tue., 10/7 | V Boys Soccer | Derby | Home - Holy Cross HS [Directions] | W 6-0 | ||
| Tue., 10/7 | FR Boys Soccer | Pomperaug | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 10/7 | V Girls Cross Country | Sacred Heart, Torrington, Seymour, Crosby | Away - Montoe Park | HC 28 Torrington 30 HC 26 Seymour 33 HC 15 Crosby 50 HC 25 SHHS 33 | ||
| Tue., 10/7 | V Girls Soccer | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | W 8-0 | 2:30pm | |
| Tue., 10/7 | FR Girls Soccer | Pomperaug | Away - PHS Soccer Field [Directions] | 3:45 p.m. | 2:30pm | |
| Tue., 10/7 | V Girls Volleyball | Naugatuck | Home - Holy Cross HS [Directions] | L 1-3 | ||
| Tue., 10/7 | JV Girls Volleyball | Naugatuck | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 10/8 | FR Football | Kennedy | Away - Hamilton Park [Directions] | 3:30 p.m. | 2:15pm | |
| Wed., 10/8 | JV Boys Soccer | Derby | Home - Lower Murray Park [Directions] | Cancelled | ||
| Wed., 10/8 | JV Girls Soccer | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:30 p.m. | ||
| Wed., 10/8 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Kennedy HS [Directions] | HC 92 SP 71 | ||
| Wed., 10/8 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | W 3-0 | 2:30pm | |
| Wed., 10/8 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/9 | V Football | Kennedy | Home - Municipal Stadium (Wtby) [Directions] | W 34-13 | 4:30pm | 2 buses- One Way |
| Thu., 10/9 | FR Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:30pm | |
| Thu., 10/9 | FR Girls Soccer | Naugatuck | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Fri., 10/10 | V Boys Soccer | Naugatuck | Away - Naugatuck High School [Directions] | L 2-1 | 4:45pm | |
| Fri., 10/10 | JV Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:30pm | |
| Fri., 10/10 | JV Girls Soccer | Naugatuck | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 10/10 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | Watertown 98 HC 82 | 4:30pm | |
| Fri., 10/10 | V Girls Volleyball | Wolcott | Home - Holy Cross HS [Directions] | L 1-3 | ||
| Fri., 10/10 | JV Girls Volleyball | Wolcott | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Sat., 10/11 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | TBA | tba | |
| Sat., 10/11 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | TBA | ||
| Sat., 10/11 | V Girls Soccer | Naugatuck | Home - Municipal Stadium (Wtby) [Directions] | W 4-1 | ||
| Mon., 10/13 | JV Football | Kennedy | Away - Hamilton Park [Directions] | 2:30 p.m. | 1:15pm | |
| Tue., 10/14 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 2-0 | 2:30pm | |
| Tue., 10/14 | V Girls Soccer | St. Paul Catholic | Home - Holy Cross HS [Directions] | W 4-0 | ||
| Tue., 10/14 | JV Girls Soccer | St. Paul Catholic | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 10/14 | V Girls Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | HC 90 Kennedy 75 | ||
| Tue., 10/14 | V Girls Volleyball | Torrington | Away - Torrington High School [Directions] | L 0-3 | 2:30pm | |
| Tue., 10/14 | JV Girls Volleyball | Torrington | Away - Torrington High School [Directions] | 4:45 p.m. | ||
| Wed., 10/15 | V Boys Cross Country | NVL Championships | Away - Veterans Park | 2:15 p.m. | 12:45pm | |
| Wed., 10/15 | FR Football | Pomperaug | Away - Sports Complex & Track [Directions] | 7:00 p.m. | 5:45pm | |
| Wed., 10/15 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:15pm | |
| Wed., 10/15 | V Girls Cross Country | NVL Championships | Away - Veterans Park | 2:15 p.m. | ||
| Wed., 10/15 | V Girls Volleyball | Northwestern | Away - NWR-7 Gym [Directions] | W 3-0 | 2:30pm | |
| Wed., 10/15 | JV Girls Volleyball | Northwestern | Away - NWR-7 Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/17 | V Football | Pomperaug | Home - Municipal Stadium (Wtby) [Directions] | L 28-29 | 5:40pm | 2 buses- One Way |
| Fri., 10/17 | JV Boys Soccer | Torrington | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 10/17 | V Girls Soccer | Torrington | Away - Torrington High School [Directions] | W 3-1 | 4:30pm | |
| Fri., 10/17 | JV Girls Soccer | Torrington | Away - Torrington High School [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/17 | V Girls Swimming and Diving | Sacred Heart | Home - Kennedy HS [Directions] | SH 95 HC 76 | ||
| Fri., 10/17 | V Girls Volleyball | Crosby | Away - Crosby HS [Directions] | W 3-0 | 2:30pm | |
| Fri., 10/17 | JV Girls Volleyball | Crosby | Away - Crosby HS [Directions] | 4:45 p.m. | ||
| Sat., 10/18 | JV Football | Pomperaug | Away - Sports Complex & Track [Directions] | 10:00 a.m. | 8:30am | |
| Sat., 10/18 | V Boys Soccer | Torrington | Home - Municipal Stadium (Wtby) [Directions] | L 3-0 | ||
| Sat., 10/18 | FR Boys Soccer | Newtown | Home - Lower Murray Park [Directions] | 9:00 a.m. | ||
| Sat., 10/18 | FR Girls Soccer | Newtown | Away - Newtown High School Practice Field [Directions] | 9:00 a.m. | 7:45am | |
| Mon., 10/20 | V Boys Cross Country | City Championships | Away - Montoe Park | 3:30 p.m. | 2:30pm | |
| Mon., 10/20 | V Boys Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | L 2-1 | 3:30pm | |
| Mon., 10/20 | V Girls Cross Country | City Championships | Away - Montoe Park | 3:30 p.m. | ||
| Mon., 10/20 | V Girls Swimming and Diving | Oxford | Home - Kennedy HS [Directions] | Ox 85 HC 83 | ||
| Mon., 10/20 | V Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | W 3-0 | 2:30pm | |
| Mon., 10/20 | JV Girls Volleyball | Wilby | Away - Wilby HS [Directions] | 3:30 p.m. | ||
| Tue., 10/21 | V Boys Soccer | Kennedy | Away - Holy Cross H.S. [Directions] | W 7-1 | ||
| Tue., 10/21 | V Girls Soccer | Oxford | Home - Municipal Stadium (Wtby) [Directions] | W 2-5 | ||
| Wed., 10/22 | V Boys Soccer | Wolcott | Home - Municipal Stadium (Wtby) [Directions] | W 1-0 | ||
| Wed., 10/22 | V Girls Soccer | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | W 1-0 | 2:45pm | |
| Wed., 10/22 | V Girls Volleyball | Kennedy | Home - Holy Cross HS [Directions] | W 3-2 | ||
| Wed., 10/22 | JV Girls Volleyball | Kennedy | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Thu., 10/23 | JV Boys Soccer | Wolcott | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Thu., 10/23 | V Girls Volleyball | Northwestern | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Thu., 10/23 | JV Girls Volleyball | Northwestern | Home - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Fri., 10/24 | V Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | L 6-42 | 5:15pm | |
| Fri., 10/24 | FR Football | Ansonia | Home - Holy Cross HS [Directions] | 3:00 p.m. | ||
| Fri., 10/24 | FR Boys Soccer | New Milford | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 10/24 | V Girls Swimming and Diving | Naugatuck, Wilby/Kaynor Tech/WCA | Away - Naugatuck High School [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 10/25 | V Boys Cross Country | CIAC Class Championships | Away - Wickham Park | TBA | tba | |
| Sat., 10/25 | JV Football | Ansonia | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 10/25 | FR Boys Soccer | Pomperaug | Away - PHS Soccer Field [Directions] | 9:00 a.m. | 7:45am | |
| Sat., 10/25 | V Girls Cross Country | CIAC Class Championships | Away - Wickham Park | TBA | ||
| Sat., 10/25 | FR Girls Soccer | Pomperaug | Home - Upper Murray Park [Directions] | 9:00 a.m. | ||
| Wed., 10/29 | V Girls Swimming and Diving | NVL Trials | Away - Kennedy HS | 4:00 p.m. | 2:30pm | |
| Thu., 10/30 | V Football | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | W 41-0 | 5:30pm | 2 buses |
| Thu., 10/30 | FR Football | Watertown | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Thu., 10/30 | V Girls Swimming and Diving | NVL Diving | Away - Kennedy HS | 6:00 p.m. | ||
| Sat., 11/1 | JV Football | Watertown | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 11/1 | V Girls Swimming and Diving | NVL Finals | Away - Kennedy HS | 4:00 p.m. | tba | |
| Mon., 11/3 | V Boys Soccer | Westbrook | Home - Municipal Stadium (Wtby) [Directions] | W 2-1 | ||
| Wed., 11/5 | FR Football | Crosby | Away - Crosby HS [Directions] | 3:30 p.m. | 2:15pm | |
| Wed., 11/5 | V Boys Soccer | Windsor Locks | Home - Holy Cross HS [Directions] | L 2-0 | ||
| Thu., 11/6 | V Football | Crosby | Home - Municipal Stadium (Wtby) [Directions] | W 41-32 | 4:30pm | 2 buses- One Way |
| Thu., 11/6 | V Girls Soccer | St. Bernard | Home - Holy Cross HS [Directions] | W 4-1 | ||
| Sat., 11/8 | JV Football | Crosby | Away - Crosby HS [Directions] | 11:00 a.m. | 9:30am | |
| Sat., 11/8 | V Girls Soccer | Notre Dame-Fairfield | Home - Municipal Stadium (Wtby) [Directions] | 3:00 p.m. | ||
| Wed., 11/12 | FR Football | Woodland | Home - Holy Cross HS [Directions] | 3:15 p.m. | ||
| Fri., 11/14 | V Football | Woodland | Away - Woodland Football Field [Directions] | W 14-7 | 4:00pm | 2 buses |
| Sat., 11/15 | JV Football | Woodland | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Mon., 11/24 | FR Football | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | Cancelled | 2:15pm | |
| Sat., 11/29 | V Football | Wolcott | Home - Municipal Stadium (Wtby) [Directions] | L 21-28 | 8:15am | 2 buses |
| Tue., 12/2 | V Girls Ice Hockey | Daniel Hand Coop (Scrim.) | Home - Lou Astorino Ice Rink [Directions] | Cancelled | ||
| Sat., 12/6 | V Wrestling | Xavier (Scrim.) | Away [Directions] | 9:00 a.m. | 8:00 a.m. | |
| Sat., 12/6 | V Girls Ice Hockey | West Haven/SHA | Home - Lou Astorino Ice Rink [Directions] | W 9-0 | ||
| Wed., 12/10 | V Girls Basketball | Seymour | Home - Tim McDonald Gymnasium [Directions] | W 65-24 | ||
| Wed., 12/10 | JV Girls Basketball | Seymour | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/10 | FR Girls Basketball | Seymour | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 12/10 | V Girls Ice Hockey | East Catholic Coop | Home - Lou Astorino Ice Rink [Directions] | L 1-6 | ||
| Fri., 12/12 | V Boys Swimming and Diving | NVL Indicational | Away - Kennedy HS | 4:00 p.m. | ||
| Fri., 12/12 | V Girls Basketball | Ansonia | Away - Ansonia High School [Directions] | W 52-11 | 3:15pm | |
| Fri., 12/12 | JV Girls Basketball | Ansonia | Away - Ansonia High School [Directions] | 4:15 p.m. | ||
| Sat., 12/13 | V Wrestling | Berlin Scrimmage | Away - Berlin HS | 9:00 a.m. | 7:30am | |
| Sat., 12/13 | V Competitive Cheerleading | UCA Cheer | Away - Hofstra University | TBA | ||
| Sat., 12/13 | V Girls Ice Hockey | Simsbury | Away [Directions] | L 0-5 | 3:30 pm | |
| Mon., 12/15 | FR Girls Basketball | Kennedy | Home - Tim McDonald Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 12/16 | V Girls Basketball | Kennedy | Home - Tim McDonald Gymnasium [Directions] | W 76-53 | ||
| Tue., 12/16 | JV Girls Basketball | Kennedy | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/17 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 48-58 | no bus | |
| Wed., 12/17 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | no bus | |
| Wed., 12/17 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | 2:30pm | |
| Wed., 12/17 | V Boys Swimming and Diving | Woodland | Home - Kennedy HS [Directions] | HC 96 Woodland 79 | ||
| Wed., 12/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Lou Astorino Ice Rink [Directions] | W 3-2 | ||
| Thu., 12/18 | V Wrestling | Holy Cross | Home - Derby High School Gymnasium [Directions] | W 75-0 [Detailed Results] | ||
| Thu., 12/18 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby High School Gymnasium [Directions] | Derby 75 HC 0 | 4:30pm | |
| Fri., 12/19 | V Boys Basketball | Torrington | Home - Tim McDonald Gymnasium [Directions] | W 58-43 | ||
| Fri., 12/19 | JV Boys Basketball | Torrington | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/19 | FR Boys Basketball | Torrington | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 12/19 | V Girls Basketball | Torrington | Away - Torrington High School [Directions] | W 69-66(OT) | 4:15pm | |
| Fri., 12/19 | JV Girls Basketball | Torrington | Away - Torrington High School [Directions] | 5:15 p.m. | ||
| Fri., 12/19 | FR Girls Basketball | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | 2:15pm | |
| Sat., 12/20 | V Wrestling | Derby Invitational | Home - Derby High School Gymnasium [Directions] | 2nd Place [Detailed Results] | ||
| Sat., 12/20 | V Wrestling | Pomperaug Coop | Away - Pomperaug HS [Directions] | 9:30 a.m. | 8:15am | |
| Sat., 12/20 | JV Girls Ice Hockey | Simsbury | Away [Directions] | W 3-2 (shootout) | ||
| Mon., 12/22 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | W 76-59 | 4:15pm | |
| Mon., 12/22 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/22 | V Wrestling | Platt Tech | Away - Platt Tech Gymnasium [Directions] | W 57-24 [Detailed Results] | 4:15 p.m. | |
| Mon., 12/22 | V Girls Basketball | Oxford | Home - Tim McDonald Gymnasium [Directions] | W 57-36 | ||
| Mon., 12/22 | JV Girls Basketball | Oxford | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 12/22 | FR Girls Basketball | Newtown | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Mon., 12/22 | V Girls Ice Hockey | Hall/Conard | Away - West Hartford [Directions] | W 2-1 | 4:45 pm | |
| Tue., 12/23 | V Boys Swimming and Diving | Avon | Home - Kennedy HS [Directions] | HC 98 Avon 85 | ||
| Sat., 12/27 | V Wrestling | Glastonbury Duals | Away - Glastonbury HS | Derby 39 Hall 32
Derby 45 Glastonbury 33
Ludlowe 40 Derby 39
Derby 46 Middletown 27
Fairfield Warde 69 Derby 3 [Detailed Results] | 7:00 a.m. | |
| Sat., 12/27 | V Girls Basketball | Career Magnet | Away - Mercy HS [Directions] | L 52-53 | tba | |
| Sat., 12/27 | V Girls Ice Hockey | Guilford Coop | Away [Directions] | W 5-1 | 3:45 pm | |
| Mon., 12/29 | V Wrestling | Oxford | Home - HCHS [Directions] | Ox 42 HC 28 | ||
| Mon., 12/29 | V Girls Basketball | Lauralton Hall | Away - Mercy HS [Directions] | W 47-32 | tba | |
| Mon., 12/29 | FR Girls Basketball | St. Paul Catholic | Home - Holy Cross HS [Directions] | 1:00 p.m. | ||
| Tue., 12/30 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 57-41 | ||
| Tue., 12/30 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 5:15 p.m. | ||
| Sat., 1/3 | V Boys Basketball | Notre Dame-West Haven | Away - Notre Dame High School [Directions] | L 54-60(OT) | 12:45pm | |
| Sat., 1/3 | JV Boys Basketball | Notre Dame-West Haven | Away - Notre Dame High School [Directions] | 2:30 p.m. | ||
| Sat., 1/3 | FR Boys Basketball | Notre Dame-West Haven | Away - Notre Dame High School [Directions] | 1:00 p.m. | 11:15am | |
| Sat., 1/3 | V Boys Swimming and Diving | Gilbert | Home - Wilby HS [Directions] | HC 97 Gilbert 75 | ||
| Sat., 1/3 | V Wrestling | Somers, Manchester, RHAM | Away - Somers HS [Directions] | Derby 66 RHAM 12
Derby 52 Manchester 22
Derby 54 Somers 25 [Detailed Results] | 7:30 a.m. | |
| Sat., 1/3 | V Wrestling | Shelton Duals | Away - SHS | NH 30 HC 9 Shelt 72 HC 9 Mor 54 HC 17 WT 39 HC 24 | 7:30am | |
| Sat., 1/3 | V Girls Basketball | Watertown | Home - Tim McDonald Gymnasium [Directions] | W 57-49 | ||
| Sat., 1/3 | JV Girls Basketball | Watertown | Home - Tim McDonald Gymnasium [Directions] | 2:15 p.m. | ||
| Sat., 1/3 | FR Girls Basketball | WCA | Home - Holy Cross HS [Directions] | 11:00 a.m. | ||
| Mon., 1/5 | JV Girls Ice Hockey | Simsbury | Home - Lou Astorino Ice Rink [Directions] | W 5-1 | ||
| Tue., 1/6 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 61-43 | 4:15pm | |
| Tue., 1/6 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 5:30 p.m. | ||
| Tue., 1/6 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 1/6 | V Girls Basketball | Wolcott | Home - Tim McDonald Gymnasium [Directions] | W 61-30 | ||
| Tue., 1/6 | JV Girls Basketball | Wolcott | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/6 | FR Girls Basketball | Wolcott | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 1/7 | V Wrestling | Ellis Tech | Home - Derby High School Gymnasium [Directions] | L 39-30 | ||
| Wed., 1/7 | V Wrestling | Northwestern | Home - HCHS [Directions] | NWR 30 HC 30 | ||
| Sat., 1/10 | FR Boys Basketball | Crosby | Home - Tim McDonald Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/10 | V Wrestling | Somers Duals | Away - SHS | Somers 48 HC 21 Gris 66 HC 12 Wood 66 HC 15 SMSA 36 HC 30 Con 60 HC 12 | 7:45am | |
| Sat., 1/10 | V Wrestling | Nonnewaug Tournament | Away - Nonnewaug HS | 2nd Place | 6:45 a.m. | |
| Sat., 1/10 | FR Girls Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | 9:00 a.m. | 7:45am | |
| Sat., 1/10 | JV Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Rink [Directions] | Cancelled | 7:45 pm | |
| Tue., 1/13 | V Boys Basketball | Crosby | Home - Tim McDonald Gymnasium [Directions] | L 69-73 | ||
| Tue., 1/13 | JV Boys Basketball | Crosby | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/13 | FR Boys Basketball | WCA | Home - HCHS [Directions] | 3:30 p.m. | ||
| Tue., 1/13 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | HC 100 Kennedy 76 | ||
| Tue., 1/13 | V Girls Basketball | Crosby | Away - Crosby HS [Directions] | W 54-44 | no bus | |
| Tue., 1/13 | JV Girls Basketball | Crosby | Away - Crosby HS [Directions] | 5:30 p.m. | no bus | |
| Wed., 1/14 | V Wrestling | St. Paul Catholic | Home - Derby High School Gymnasium [Directions] | W 65-18 | ||
| Wed., 1/14 | V Wrestling | Seymour | Away - Seymour High School [Directions] | SEY 63 HC 18 | 4:30pm | |
| Wed., 1/14 | V Girls Ice Hockey | Guilford Coop | Home - Lou Astorino Ice Rink [Directions] | W 8-5 | ||
| Thu., 1/15 | V Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | L 61-66 | no bus | |
| Thu., 1/15 | JV Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | no bus | |
| Thu., 1/15 | FR Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 3:15 p.m. | 2:30pm | no bus |
| Thu., 1/15 | V Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | W 57-11 | 4:30pm | |
| Thu., 1/15 | JV Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | ||
| Thu., 1/15 | FR Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:30pm | |
| Thu., 1/15 | JV Girls Ice Hockey | Daniel Hand Coop | Home - Lou Astorino Ice Rink [Directions] | W 10-0 | ||
| Fri., 1/16 | V Boys Indoor Track | NVL Developmental | Away - Wesleyan University | TBA | tba | |
| Fri., 1/16 | V Boys Swimming and Diving | Crosby/WCA | Home - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Fri., 1/16 | V Girls Basketball | Wilby | Home - Tim McDonald Gymnasium [Directions] | W 57-11 | ||
| Fri., 1/16 | JV Girls Basketball | Wilby | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/16 | V Girls Indoor Track | NVL Developmental | Away - Wesleyan University | TBA | ||
| Sat., 1/17 | V Wrestling | Seymour, Gilbert/Torrington | Home - Derby High School Gymnasium [Directions] | Derby 55. Seymour 21 Derby 58 Gilbert 18 | ||
| Sat., 1/17 | V Wrestling | New Milford Tournament | Away | 9:30 a.m. | 7:30am | |
| Sat., 1/17 | JV Wrestling | Xavier JV Tournament | Away | 9:00 a.m. | 7:00a.m. | @ Xavier HS in Middletown |
| Sat., 1/17 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Rink [Directions] | W 11-0 | 5:00 pm | |
| Tue., 1/20 | V Boys Basketball | Woodland | Home - Tim McDonald Gymnasium [Directions] | W 92-44 | ||
| Tue., 1/20 | JV Boys Basketball | Woodland | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/20 | FR Boys Basketball | Woodland | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/20 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Kennedy HS [Directions] | 4:00 p.m. | ||
| Tue., 1/20 | V Boys Swimming and Diving | Naugatuck | Home - Kennedy HS [Directions] | 4:00 p.m. | ||
| Tue., 1/20 | V Girls Basketball | Woodland | Away - Woodland High School Gym [Directions] | W 72-47 | 4:15pm | |
| Tue., 1/20 | JV Girls Basketball | Woodland | Away - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/21 | V Boys Basketball | Naugatuck | Home - Tim McDonald Gymnasium [Directions] | L 82-88(OT) | ||
| Wed., 1/21 | JV Boys Basketball | Naugatuck | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/21 | FR Boys Basketball | Naugatuck | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 1/21 | V Wrestling | Wolcott Tech | Home - Derby High School Gymnasium [Directions] | W 51-18 | ||
| Wed., 1/21 | V Wrestling | St. Paul Catholic | Away - ST Paul Catholic HS [Directions] | SP 54 HC 18 | 5:15pm | |
| Wed., 1/21 | V Girls Ice Hockey | East Catholic Coop | Away - Newington [Directions] | L 0-4 | 2:00 pm | |
| Fri., 1/23 | FR Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 3:30 p.m. | 2:30pm | |
| Fri., 1/23 | V Boys Swimming and Diving | HK-Valley | Away - HK [Directions] | Cancelled | 2:15pm | |
| Fri., 1/23 | FR Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 6:00 p.m. | ||
| Fri., 1/23 | V Girls Ice Hockey | West Haven/SHA | Away [Directions] | W 8-0 | 3:15 pm | |
| Sat., 1/24 | V Wrestling | Oxford Tournament | Away - Oxford HS | Cancelled | 7:30 a.m. | |
| Sat., 1/24 | V Wrestling | Oxford Tournament | Away - Oxford HS | 8:00 a.m. | 6:30am | |
| Wed., 1/28 | V Boys Basketball | Derby | Away - Derby HS Vitello Gymnasium [Directions] | W 80-56 | 4:15pm | |
| Wed., 1/28 | JV Boys Basketball | Derby | Away - Derby HS Vitello Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/28 | V Wrestling | Housatonic Regional | Away - Housatonic [Directions] | Cancelled | 4:30pm | |
| Wed., 1/28 | V Girls Basketball | Derby | Home - Tim McDonald Gymnasium [Directions] | W 73-43 | ||
| Wed., 1/28 | JV Girls Basketball | Derby | Home - Tim McDonald Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 1/28 | V Girls Ice Hockey | Branford | Home - Lou Astorino Ice Rink [Directions] | W 7-2 | ||
| Thu., 1/29 | V Wrestling | Oxford | Away - OHS-Main Gym [Directions] | W 68-6 | 5:30 p.m. | |
| Thu., 1/29 | JV Girls Ice Hockey | Branford | Home - Lou Astorino Ice Rink [Directions] | W 4-1 | ||
| Fri., 1/30 | V Boys Basketball | Sacred Heart | Home - Tim McDonald Gymnasium [Directions] | L 43-67 | ||
| Fri., 1/30 | JV Boys Basketball | Sacred Heart | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/30 | FR Boys Basketball | Sacred Heart | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/30 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | W 42-33 | no bus | |
| Fri., 1/30 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | no bus | |
| Fri., 1/30 | FR Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 3:30 p.m. | ||
| Sat., 1/31 | V Wrestling | Jonathan Law, Enfield, New Haven Wrestling, Platt Tech | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | Derby 39 New Haven 30 Law 40 Derby 39 Shelton 49 Derby 28 Derby 42 Enfield 38 | 8:15 a.m. | |
| Sat., 1/31 | V Wrestling | Manchester, Terryville-Thomaston | Home - HCHS [Directions] | Terryville 51 HC 12 Manchester 30 HC 18 | ||
| Sat., 1/31 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavillion [Directions] | W 9-1 | 3:15 pm | |
| Wed., 2/4 | V Boys Basketball | St. Paul Catholic | Home - Tim McDonald Gymnasium [Directions] | W 56-54 | ||
| Wed., 2/4 | JV Boys Basketball | St. Paul Catholic | Home - Tim McDonald Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/4 | V Boys Swimming and Diving | Oxford | Home - Kennedy HS [Directions] | HC 89 Ox 63 | ||
| Wed., 2/4 | V Wrestling | Wolcott Tech | Home - HCHS [Directions] | WT 37 HC 12 | ||
| Wed., 2/4 | V Wrestling | Old Saybrook | Away [Directions] | Cancelled | 4:00 p.m. | |
| Wed., 2/4 | V Girls Ice Hockey | Daniel Hand Coop | Home - Lou Astorino Ice Rink [Directions] | W 8-0 | ||
| Thu., 2/5 | FR Boys Basketball | Crosby | Away - Crosby HS [Directions] | 7:00 p.m. | no bus | |
| Thu., 2/5 | V Competitive Cheerleading | UCA Nationals | Away - Disney World | TBA | ||
| Thu., 2/5 | V Girls Ice Hockey | Lauralton Hall | Home - Lou Astorino Ice Rink [Directions] | W 7-0 | ||
| Fri., 2/6 | V Boys Basketball | Crosby | Away - Crosby HS [Directions] | L 61-93 | no bus | |
| Fri., 2/6 | JV Boys Basketball | Crosby | Away - Crosby HS [Directions] | 5:30 p.m. | no bus | |
| Fri., 2/6 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | HC 93.5 TOR 76.5 | 5:45pm | |
| Fri., 2/6 | V Girls Basketball | Crosby | Home - Tim McDonald Gymnasium [Directions] | W 42-30 | ||
| Fri., 2/6 | JV Girls Basketball | Crosby | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 2/7 | FR Boys Basketball | St. Paul Catholic | Home - Tim McDonald Gymnasium [Directions] | 9:30 a.m. | ||
| Sat., 2/7 | V Wrestling | Granby Memorial, Morgan, Griswold/Wheeler, Canton | Away - Granby Memorial High School [Directions] | Derby 47 Griswold 24 Derby 60. Canton 9 Derby 42 Morgan 33 Derby 52 Granby 21 | 6:30 a.m. | |
| Sat., 2/7 | V Wrestling | EnricoFermi, New Britain, Wethersfield | Away - Fermi HS | TBA | tba | |
| Sat., 2/7 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 64-43 | 12:15pm | |
| Sat., 2/7 | JV Girls Basketball | Pomperaug | Home - Holy Cross HS [Directions] | Cancelled | ||
| Sat., 2/7 | FR Girls Basketball | Pomperaug | Home - Holy Cross HS [Directions] | 11:00 a.m. | ||
| Sat., 2/7 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Shelton [Directions] | W 5-0 | 12:30 pm | |
| Sun., 2/8 | V Boys Indoor Track | NVL Championships | Away - New Haven Athletic | 9:30 p.m. | 7:30am | |
| Sun., 2/8 | V Girls Indoor Track | NVL Championships | Away - New Haven Athletic | 9:30 a.m. | ||
| Tue., 2/10 | V Boys Basketball | Kennedy | Home - Tim McDonald Gymnasium [Directions] | W 74-67 | ||
| Tue., 2/10 | JV Boys Basketball | Kennedy | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/10 | FR Boys Basketball | Kennedy | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 2/10 | V Boys Swimming and Diving | Watertown | Away - Watertown HS [Directions] | HC 102 Wat 82 | 4:45pm | |
| Tue., 2/10 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 47-37 | no bus | |
| Tue., 2/10 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | no bus | |
| Tue., 2/10 | FR Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | 2:30pm | |
| Tue., 2/10 | V Girls Ice Hockey | Simsbury | Home - Lou Astorino Ice Rink [Directions] | L 2-4 | ||
| Wed., 2/11 | V Wrestling | Gilbert/Torrington | Home - Holy Cross HS [Directions] | 6:30 p.m. | ||
| Wed., 2/11 | V Girls Basketball | Wilby | Away - Wilby H.S. [Directions] | W 60-22 | no bus | |
| Wed., 2/11 | Winter Dance Team | NVL Dance Championships | Away - Woodland HS | TBA | tba | |
| Wed., 2/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Lou Astorino Ice Rink [Directions] | W 7-1 | ||
| Wed., 2/11 | JV Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | W 6-0 | 6:30 pm | |
| Thu., 2/12 | V Boys Basketball | Kaynor Tech | Home - Tim McDonald Gymnasium [Directions] | W 57-55 | ||
| Thu., 2/12 | JV Boys Basketball | Kaynor Tech | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/12 | FR Boys Basketball | Kaynor Tech | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Thu., 2/12 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/12 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 2/14 | V Boys Basketball | Wilby | Home - Tim McDonald Gymnasium [Directions] | W 78-53 | ||
| Sat., 2/14 | JV Boys Basketball | Wilby | Home - Tim McDonald Gymnasium [Directions] | 1:45 p.m. | ||
| Sat., 2/14 | V Wrestling | Berkshire Valley Tournament | Away | 9:00 a.m. | 7:00 a.m. | @ Nonnewaug HS - Woodbury CT |
| Sat., 2/14 | JV Girls Basketball | St. Paul Catholic | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 2/14 | FR Girls Basketball | St. Paul Catholic | Home - Holy Cross HS [Directions] | 8:15 a.m. | 2:15pm | |
| Sat., 2/14 | V Girls Ice Hockey | Hall/Conard | Home - Lou Astorino Ice Rink [Directions] | W 5-1 | ||
| Mon., 2/16 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy High School Pool | HC 104 SH 82 | ||
| Mon., 2/16 | V Girls Ice Hockey | New Canaan | Away - Darien [Directions] | W 2-0 | 2:00 pm | |
| Tue., 2/17 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | L 56-98 | no bus | |
| Tue., 2/17 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | no bus | |
| Tue., 2/17 | V Boys Swimming and Diving | Seymour | Away - Seymour High School [Directions] | HC 89 Sey 73 | 4:30pm | |
| Tue., 2/17 | V Girls Basketball | Sacred Heart | Home - Tim McDonald Gymnasium [Directions] | W 64-43 | ||
| Tue., 2/17 | JV Girls Basketball | Sacred Heart | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/17 | FR Girls Basketball | Sacred Heart | Home - Tim McDonald Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 2/18 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away [Directions] | W 4-0 | 4:30 pm | |
| Fri., 2/20 | V Boys Basketball | Seymour | Away - Seymour High School [Directions] | W 70-29 | 4:15pm | |
| Fri., 2/20 | JV Boys Basketball | Seymour | Away - Seymour High School [Directions] | 5:15 p.m. | ||
| Fri., 2/20 | FR Boys Basketball | Seymour | Away - Seymour High School [Directions] | 3:30 p.m. | 2:30pm | |
| Fri., 2/20 | V Boys Swimming and Diving | Suffield | Home - Kennedy HS [Directions] | 4:30 p.m. | ||
| Fri., 2/20 | V Wrestling | Class S State Championships | Away | 3:30 p.m. | 1:30 p.m. | @ HK high school Higganum CT |
| Fri., 2/20 | V Wrestling | CIAC Class S Meet | Away | TBA | ||
| Sat., 2/21 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 12:00 p.m. | ||
| Sat., 2/21 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/21 | V Wrestling | Class S State Championships | Away | 9:00 a.m. | 7:00 a.m. | |
| Sat., 2/21 | V Competitive Cheerleading | NVL Championships | Away - Crosby HS | 11:00 a.m. | tba | |
| Sat., 2/21 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Tue., 2/24 | V Boys Basketball | Ansonia | Home - Tim McDonald Gymnasium [Directions] | W 67-55 | ||
| Tue., 2/24 | JV Boys Basketball | Ansonia | Home - Tim McDonald Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/24 | V Boys Swimming and Diving | Northwestern | Home - Kennedy HS [Directions] | HC 98 NW 85 | ||
| Tue., 2/24 | V Girls Ice Hockey | Simsbury | Away - Simsbury [Directions] | L 1-4 (SCC Tournament) | Yes | |
| Wed., 2/25 | FR Boys Basketball | WCA | Home - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Wed., 2/25 | FR Boys Basketball | WCA | Home - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Fri., 2/27 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | ||
| Fri., 2/27 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | 2:45pm | |
| Fri., 2/27 | V Wrestling | State Open Championships | Away - Hillhouse Athletic Center | 3:30 p.m. | TBA | |
| Fri., 2/27 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | ||
| Sat., 2/28 | V Wrestling | State Open Championships | Away - Hillhouse Athletic Center | 9:00 a.m. | TBA | |
| Mon., 3/2 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Lou Astorino Ice Rink [Directions] | W 5-1 (State Tournament Quarterfinals) | vs Stamford/Westhill/Staples | |
| Tue., 3/3 | V Boys Swimming and Diving | NVL Trials | Away - Kennedy HS | 4:00 p.m. | ||
| Wed., 3/4 | V Boys Swimming and Diving | NVL Diving | Away - Kennedy HS | 6:00 p.m. | ||
| Wed., 3/4 | V Girls Basketball | Haddam-Killingworth | Home - Holy Cross HS [Directions] | 6:00 p.m. | ||
| Wed., 3/4 | V Girls Ice Hockey | East Catholic Coop | Away - Sports Center of CT, 784 River Rd. Shelton [Directions] | L 1-5 (State Tournament Semifinals) | 5:15 pm | |
| Fri., 3/6 | V Boys Swimming and Diving | NVL Finals | Away - Kennedy HS | 6:00 p.m. | ||
| Fri., 3/6 | V Wrestling | New England Championships | Away | 3:30 p.m. | ||
| Fri., 3/6 | V Girls Basketball | Granby Memorial | Home - Holy Cross HS [Directions] | 7:00 p.m. | ||
| Sat., 3/7 | V Wrestling | New England Championships | Away | 9:00 a.m. | ||
| Tue., 3/10 | V Boys Basketball | Somers | Home - Holy Cross HS [Directions] | 6:00 p.m. | ||
| Tue., 3/10 | V Girls Basketball | Enfield | Home - Holy Cross HS [Directions] | 7:45 p.m. | ||
| Thu., 3/12 | V Boys Basketball | Haddam-Killingworth | Home - Holy Cross HS [Directions] | 7:00 p.m. | ||
| Tue., 3/31 | V Baseball | Maloney (Scrim.) | Away - Maloney High School [Directions] | Cancelled | 2:15pm | |
| Tue., 3/31 | V Baseball | Maloney (Scrim.) | Away - Maloney High School [Directions] | Cancelled | 2:15pm | |
| Wed., 4/1 | V Girls Lacrosse | Foran (Scrim.) | Away - Foran High School - Turf Field [Directions] | 4:30 p.m. | 2:45pm | |
| Thu., 4/2 | V Softball | Pomperaug (Scrim.) | Away - PHS Softball Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 4/6 | V Baseball | New Milford (Scrim.) | Away - New Milford High School [Directions] | 3:30 p.m. | 2:15pm | |
| Mon., 4/6 | V Baseball | New Milford (Scrim.) | Away - New Milford High School [Directions] | Cancelled | 2:15pm | |
| Mon., 4/6 | V Baseball | New Milford (Scrim.) | Away - New Milford High School [Directions] | Cancelled | 2:15pm | |
| Wed., 4/8 | V Baseball | Seymour | Home - Waterville Park [Directions] | W 10-5 | ||
| Wed., 4/8 | V Boys Tennis | Kennedy | Home - Holy Cross HS [Directions] | W 8-1 | ||
| Wed., 4/8 | V Softball | Seymour | Away - Seymour High School [Directions] | W 3-2 | 2:15pm | |
| Thu., 4/9 | V Girls Tennis | Ansonia | Home - Holy Cross HS [Directions] | W 7-0 | ||
| Fri., 4/10 | V Boys Tennis | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | L 1-8 | ||
| Fri., 4/10 | V Softball | Kennedy | Away - Municipal Stadium [Directions] | W 20-0 | ||
| Sat., 4/11 | V Baseball | Kennedy | Home - Waterville Park [Directions] | W 5-4 | ||
| Sat., 4/11 | JV Baseball | Kennedy | Home - Waterville Park [Directions] | 1:30 p.m. | ||
| Sat., 4/11 | V Boys Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | L 1-19 | 2:45pm | |
| Sat., 4/11 | V Girls Lacrosse | Rocky Hill | Away - Rocky Hill High School [Directions] | L 4-11 | 9:15am | |
| Mon., 4/13 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | L 12-8 | 2:15pm | |
| Mon., 4/13 | V Boys Lacrosse | St. Paul Catholic | Home - Holy Cross HS [Directions] | W 7-4 | ||
| Mon., 4/13 | V Boys Tennis | Torrington | Away - Torrington High School [Directions] | W 6-3 | ||
| Mon., 4/13 | V Softball | Torrington | Home - Huntingdon 3 [Directions] | L 5-1 | ||
| Mon., 4/13 | V Girls Tennis | Torrington | Home - Holy Cross HS [Directions] | W 4-3 | ||
| Tue., 4/14 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | L 3-4 | 2:15pm | |
| Tue., 4/14 | FR Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:45 p.m. | ||
| Tue., 4/14 | V Boys Tennis | Wolcott | Home - Holy Cross HS [Directions] | L 4-5 | ||
| Tue., 4/14 | V Girls Lacrosse | Capital Prep | Home - Holy cross [Directions] | W 14-2 | ||
| Tue., 4/14 | V Softball | Ansonia | Home - HCHS [Directions] | W 9-0 | ||
| A request to make the following change(s) to the above event has been submitted by one of the schools involved, but has not yet been accepted by the other -- Change facility to Huntingdon 3 | ||||||
| Tue., 4/14 | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | L 1-6 | ||
| Wed., 4/15 | JV Baseball | Oxford | Away - Oxford HS [Directions] | 3:30 p.m. | ||
| Wed., 4/15 | V Boys Outdoor Track | Derby, Sacred Heart, Wilby | Home - Holy Cross HS [Directions] | Derby 83 HC 63 HC 108 SH 33 HC 100 WIlby 46 | ||
| Wed., 4/15 | V Girls Outdoor Track | Derby, Sacred Heart, Wilby | Home - Holy Cross HS [Directions] | HC 75 SH 66 HC 97 Derby 44 HC 109 Wilby 32 | ||
| Wed., 4/15 | V Softball | Oxford | Away - OHS Softball Field [Directions] | L 0-4 | 2:15pm | |
| Thu., 4/16 | V Baseball | Oxford | Home - HCHS [Directions] | W 5-4 | ||
| Thu., 4/16 | JV Softball | Oxford | Away - OHS Softball Field [Directions] | 3:30 p.m. | ||
| Fri., 4/17 | V Baseball | Watertown | Home - HCHS [Directions] | L 9-6 | ||
| Fri., 4/17 | FR Baseball | Naugatuck | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 4/17 | V Boys Tennis | Watertown | Home - Holy Cross HS [Directions] | W 8-1 | ||
| Fri., 4/17 | V Softball | Watertown | Away - Watertown High School [Directions] | L 4-0 | 2:15pm | |
| Fri., 4/17 | V Girls Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | L 5-2 | ||
| Sat., 4/18 | JV Baseball | Watertown | Home - HCHS [Directions] | 1:00 p.m. | ||
| Sat., 4/18 | V Boys Lacrosse | Immaculate | Away - Mustang Valley [Directions] | L 5-16 | 1:30pm | |
| Sat., 4/18 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | L 9-12 | 9:15am | |
| Mon., 4/20 | V Boys Lacrosse | Housatonic Regional | Away - HVRHS Field [Directions] | L 9-5 | 2:15pm | |
| Tue., 4/21 | V Boys Golf | Naugatuck | Home - Western Hills [Directions] | HC 171 Naugy 244 | ||
| Tue., 4/21 | V Boys Outdoor Track | Kennedy, Oxford, St. Paul Catholic | Home - Holy Cross HS [Directions] | HC 109 OX 36 HC 98 KEN 47 HC 120 SP 25 | ||
| Tue., 4/21 | V Girls Outdoor Track | Kennedy, Oxford, St. Paul Catholic | Home - Holy Cross HS [Directions] | HC 107 STP 41 HC 119 KEN 26 HC 80.5 OX 67.5 | ||
| Tue., 4/21 | V Girls Tennis | Seymour | Away - Seymour High School [Directions] | L 3-4 | ||
| Wed., 4/22 | FR Baseball | Naugatuck | Away - Rotary Field [Directions] | 3:30 p.m. | ||
| Wed., 4/22 | JV Softball | Naugatuck | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Thu., 4/23 | V Baseball | Wolcott | Home - HCHS [Directions] | W 1-0 | ||
| Thu., 4/23 | JV Baseball | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:15pm | |
| Thu., 4/23 | V Boys Golf | Sacred Heart, Wilby | Home - Western Hills [Directions] | HC 164 SH 211 WIL 268 | ||
| Thu., 4/23 | V Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | L 10-14 | 2:15pm | |
| Thu., 4/23 | JV Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | 5:15 p.m. | ||
| Thu., 4/23 | V Softball | Wolcott | Away - George Babcock Field, Wolcott High School [Directions] | W 9-4 | 2:30pm | |
| Thu., 4/23 | JV Softball | Wolcott | Away - George Babcock Field, Wolcott High School [Directions] | 4:00 p.m. | ||
| Fri., 4/24 | V Baseball | Crosby | Away - Washington Park [Directions] | W 10-2 | 2:15pm | |
| Fri., 4/24 | V Boys Tennis | Crosby | Away - Crosby HS [Directions] | W 8-1 | ||
| Fri., 4/24 | V Softball | Crosby | Home - HCHS [Directions] | W 20-3 | ||
| Fri., 4/24 | JV Softball | Crosby | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 4/24 | V Girls Tennis | Crosby | Home - Holy Cross HS [Directions] | L 3-4 | ||
| Sat., 4/25 | JV Baseball | Crosby | Away - Washington Park [Directions] | 12:00 p.m. | ||
| Sat., 4/25 | V Boys Lacrosse | Wamogo | Home - Holy Cross HS [Directions] | W 16-4 | ||
| Sat., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | 7:30am | |
| Sat., 4/25 | V Girls Lacrosse | Immaculate | Home - Holy Cross HS [Directions] | L 6-22 | ||
| Sat., 4/25 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | 7:30am | |
| Sat., 4/25 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | 7:30am | |
| Mon., 4/27 | V Baseball | Wilby | Home - HCHS [Directions] | W 20-4 | ||
| Mon., 4/27 | FR Baseball | Wilby | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Mon., 4/27 | V Boys Golf | Crosby | Home - Western Hills [Directions] | Holy Cross-181 Crosby-277 | ||
| Mon., 4/27 | V Boys Lacrosse | Amistad | Home - Post University [Directions] | W 17-3 | ||
| Mon., 4/27 | V Boys Tennis | Wilby | Home - Holy Cross HS [Directions] | W 7-2 | ||
| Mon., 4/27 | V Girls Lacrosse | Amistad | Away - AF Amistad High School [Directions] | W 17-9 | 2:15pm | |
| Mon., 4/27 | V Softball | Wilby | Away - Bucks Hill Park [Directions] | W 27-0 | 2:30pm | |
| Mon., 4/27 | JV Softball | Wilby | Away - Bucks Hill Park [Directions] | 3:30 p.m. | ||
| Mon., 4/27 | V Girls Tennis | Wilby | Away - Wilby HS [Directions] | W 7-0 | ||
| Tue., 4/28 | V Baseball | Naugatuck | Away - Naugatuck High School [Directions] | L 4-5 | 2:15pm | |
| Tue., 4/28 | V Boys Golf | Watertown | Away - Crestbrook Park Golf Course [Directions] | WAT 163 HC 174 | ||
| Tue., 4/28 | V Boys Outdoor Track | Naugatuck, Crosby | Away - Naugatuck High School [Directions] | NAUGY 94 HC 58 HC 86 CROSBY 64 | 2:15pm | |
| Tue., 4/28 | V Girls Outdoor Track | Naugatuck, Crosby | Away - Naugatuck High School [Directions] | NAUGY 82 HC 64 HC 102 CROSBY 38 | ||
| Tue., 4/28 | V Girls Tennis | Wolcott | Away - Wolcott High School [Directions] | L 1-6 | ||
| Wed., 4/29 | V Baseball | Woodland | Away - Woodland High School Baseball Field [Directions] | W 6-0 | 2:15pm | |
| Wed., 4/29 | FR Baseball | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Wed., 4/29 | V Boys Lacrosse | Watertown | Home - Holy Cross HS [Directions] | L 10-15 | ||
| Wed., 4/29 | JV Boys Lacrosse | Watertown | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Wed., 4/29 | V Boys Tennis | Woodland | Away - Woodland High School Tennis courts [Directions] | W 9-0 | ||
| Wed., 4/29 | V Girls Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | L 15-8 | 2:15pm | |
| Wed., 4/29 | V Softball | Woodland | Home - HCHS [Directions] | W 6-0 | ||
| Wed., 4/29 | JV Softball | Woodland | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 4/29 | V Girls Tennis | Woodland | Home - Holy Cross HS [Directions] | L 5-2 | ||
| Thu., 4/30 | JV Baseball | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | 2:30pm | |
| Thu., 4/30 | V Boys Golf | St. Paul Catholic, Wilby | Home - Western Hills [Directions] | Holy Cross-174 St Paul -197 | ||
| Fri., 5/1 | FR Baseball | WCA | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 5/1 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 14-10 | 4:15pm | |
| Fri., 5/1 | V Boys Tennis | Sacred Heart | Home - Holy Cross HS [Directions] | W 6-3 | ||
| Fri., 5/1 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | L 2-3 | 2:30pm | |
| Fri., 5/1 | JV Softball | WCA | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 5/1 | V Girls Tennis | Sacred Heart | Away - Fulton Park | W 4-3 | 2:30pm | |
| Sat., 5/2 | JV Baseball | Ansonia | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 5/2 | V Boys Outdoor Track | Torrington Invite | Away - Torrington HS | 3:30 p.m. | 2:00pm | |
| Sat., 5/2 | V Girls Outdoor Track | Torrington Invite | Away - Torrington HS | 3:30 p.m. | 2:00pm | |
| Mon., 5/4 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 2-1 | 2:15pm | |
| Mon., 5/4 | FR Baseball | St. Paul Catholic | Away - Paige Park, Bristol [Directions] | 3:00 p.m. | 1:45pm | |
| Mon., 5/4 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | Woodland-179 Holy Cross-186 | ||
| Mon., 5/4 | V Softball | St. Paul Catholic | Home - HCHS [Directions] | L 1-2 | ||
| Mon., 5/4 | JV Softball | St. Paul Catholic | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Mon., 5/4 | V Girls Tennis | St. Paul Catholic | Home - Holy Cross HS [Directions] | L 2-5 | ||
| Tue., 5/5 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 5/5 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | Torrington-178 Holy Cross-185 | ||
| Tue., 5/5 | V Boys Outdoor Track | Watertown, Seymour | Away - John J. Mills Complex @ Watertown High School [Directions] | HC 92 Wat57 HC 78 Sey 72 | 2:15pm | |
| Tue., 5/5 | V Boys Tennis | Kennedy | Away - Chase Park [Directions] | W 9-0 | ||
| Tue., 5/5 | V Girls Lacrosse | Housatonic Regional | Home - Holy Cross HS [Directions] | W 7-5 | ||
| Tue., 5/5 | V Girls Outdoor Track | Watertown, Seymour | Away - John J. Mills Complex @ Watertown High School [Directions] | HC 84 Wat 66 Sey 79 HC 70 | ||
| Tue., 5/5 | V Softball | Naugatuck | Home - HCHS [Directions] | W 4-2 | ||
| Tue., 5/5 | V Girls Tennis | Naugatuck | Home - Holy Cross HS [Directions] | L 5-2 | ||
| Wed., 5/6 | V Baseball | Derby | Home - HCHS [Directions] | W 17-9 | ||
| Wed., 5/6 | FR Baseball | Naugatuck | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 5/6 | V Boys Lacrosse | Housatonic Regional | Home - Holy Cross HS [Directions] | W 11-9 | ||
| Wed., 5/6 | V Girls Lacrosse | Housatonic Regional | Away - HRHS [Directions] | W 7-0 | 2:15pm | |
| Wed., 5/6 | V Softball | Derby | Away - Derby- Ryan Athletic Complex- softball field [Directions] | W 17-0 | 2:30pm | |
| Thu., 5/7 | JV Baseball | Derby | Home - HCHS [Directions] | 3:45 p.m. | ||
| Thu., 5/7 | V Boys Tennis | Naugatuck | Home - Holy Cross HS [Directions] | W 6-0 | ||
| Thu., 5/7 | V Boys Tennis | Naugatuck | Away - Naugatuck High School [Directions] | W 6-3 | ||
| Thu., 5/7 | V Girls Lacrosse | Lewis Mills | Home - Holy Cross HS [Directions] | L 16-21 | ||
| Thu., 5/7 | JV Softball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Fri., 5/8 | V Baseball | Sacred Heart | Away - Municipal Stadium | L 5-11 | 2:15pm | |
| Fri., 5/8 | FR Baseball | Sacred Heart | Away - Fulton Park | 3:45 p.m. | ||
| Fri., 5/8 | V Boys Tennis | Sacred Heart | Away - Fulton Park | W 6-3 | ||
| Fri., 5/8 | V Softball | Sacred Heart | Home - HCHS [Directions] | W 17-1 | ||
| Fri., 5/8 | V Girls Tennis | Sacred Heart | Home - Holy Cross HS [Directions] | W 4-3 | ||
| Sat., 5/9 | JV Baseball | Sacred Heart | Away - Fulton Park | 10:30 a.m. | ||
| Sat., 5/9 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | L 14-4 | 11:00am | |
| Sat., 5/9 | V Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | L 22-11 | 9:15am | |
| Mon., 5/11 | V Baseball | Wilby | Away - Municipal Stadium [Directions] | W 13-6 | 2:15pm | |
| Mon., 5/11 | FR Baseball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Mon., 5/11 | V Boys Golf | Waterbury Coop | Away - Western Hills [Directions] | Holy Cross-173 Kennedy-237 | ||
| Mon., 5/11 | V Boys Lacrosse | Lewis Mills | Home - Post University [Directions] | L 5-9 | ||
| Mon., 5/11 | JV Boys Lacrosse | Lewis Mills | Home - Holy Cross HS [Directions] | Cancelled | ||
| Mon., 5/11 | V Boys Tennis | Wilby | Away - Wilby HS [Directions] | W 7-2 | ||
| Mon., 5/11 | V Girls Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | L 5-17 | 2:15pm | |
| Mon., 5/11 | V Softball | Wilby | Home - HCHS [Directions] | W 15-0 | ||
| Mon., 5/11 | JV Softball | Wilby | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Mon., 5/11 | V Girls Tennis | Wilby | Home - Holy Cross HS [Directions] | W 7-0 | ||
| Tue., 5/12 | JV Baseball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 5/12 | V Boys Golf | Wolcott | Away - Farmingbury Country Club [Directions] | Holy Cross-165 Wolcott-188 | ||
| Tue., 5/12 | V Boys Outdoor Track | Torrington, Wolcott, Woodland | Away - Torrington HS [Directions] | WOOD 109 HC 41 HC 76 TORR 74 HC 78 WOL 72 | 1:45pm | |
| Tue., 5/12 | V Girls Lacrosse | Masuk | Away - Masuk Stadium Field [Directions] | L 7-15 | 4:00pm | |
| Tue., 5/12 | V Girls Outdoor Track | Torrington, Wolcott, Woodland | Away - Torrington HS [Directions] | WOOD 137 HC 23 TORR 82 HC 64 HC 91 WOL 55 | ||
| Wed., 5/13 | V Baseball | Crosby | Home - HCHS [Directions] | W 6-1 | ||
| Wed., 5/13 | FR Baseball | Wolcott | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 5/13 | V Boys Lacrosse | Wamogo | Away - Wamogo MS Soccer Field (Lower Field) [Directions] | W 16-7 | 2:15pm | |
| Wed., 5/13 | V Boys Tennis | Crosby | Home - Holy Cross HS [Directions] | W 9-0 | ||
| Wed., 5/13 | V Girls Lacrosse | Capital Prep | Home - Holy Cross HS [Directions] | W 1-0 | ||
| Wed., 5/13 | V Softball | Crosby | Away - Crosby HS Field #1 [Directions] | W 18-1 | 2:30pm | |
| Wed., 5/13 | JV Softball | Crosby | Away - Crosby HS Field #2 [Directions] | 3:30 p.m. | ||
| Wed., 5/13 | V Girls Tennis | Crosby | Away - Crosby HS [Directions] | W 4-3 | ||
| Thu., 5/14 | V Baseball | Kennedy | Away - Waterville Park [Directions] | W 10-5 | 2:15pm | |
| Thu., 5/14 | JV Baseball | Crosby | Home - HCHS [Directions] | 3:30 p.m. | ||
| Thu., 5/14 | FR Baseball | Kennedy | Away - Bucks Hill Park [Directions] | 3:30 p.m. | ||
| Thu., 5/14 | V Softball | Kennedy | Home - HCHS [Directions] | W 23-1 | ||
| Thu., 5/14 | V Girls Tennis | Kennedy | Home - Holy Cross HS [Directions] | W 4-3 | ||
| Sat., 5/16 | V Boys Lacrosse | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | W 15-7 | 9:30am | |
| Sat., 5/16 | JV Boys Lacrosse | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | 12:30 p.m. | ||
| Sat., 5/16 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Holy Cross HS [Directions] | L 7-8 | ||
| Mon., 5/18 | V Baseball | Bethel | Away - Hunt Field at Bethel High School [Directions] | L 2-20 | 2:15pm | |
| Mon., 5/18 | JV Baseball | Bethel | Away - Parloa Field [Directions] | 3:45 p.m. | ||
| Mon., 5/18 | V Boys Golf | Woodland | Home - Western Hills [Directions] | Holy Cross-172 Woodland-174 | ||
| Mon., 5/18 | V Boys Lacrosse | Amistad | Away - AF Amistad High School [Directions] | W 17-7 | 2:15pm | |
| Mon., 5/18 | V Girls Lacrosse | Amistad | Home - Post University [Directions] | W 17-9 | ||
| Tue., 5/19 | V Baseball | Sacred Heart | Home - HCHS [Directions] | W 4-3 | ||
| Tue., 5/19 | FR Baseball | Sacred Heart | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Tue., 5/19 | V Boys Golf | Waterbury Coop | Home - Western Hills [Directions] | Holy Cross-168 Kennedy-242 | ||
| Tue., 5/19 | V Boys Outdoor Track | City Meet | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/19 | V Girls Outdoor Track | City Meet | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/19 | V Softball | Sacred Heart | Away - Municipal Stadium | W 13-5 | 2:30pm | |
| Tue., 5/19 | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | 3:45 p.m. | ||
| Wed., 5/20 | V Baseball | Kaynor Tech | Home - HCHS [Directions] | W 17-1 | ||
| Wed., 5/20 | V Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | L 6-9 | 2:15pm | |
| Wed., 5/20 | JV Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | Cancelled | ||
| Wed., 5/20 | V Girls Lacrosse | Watertown | Home - Post University [Directions] | L 15-12 | ||
| Wed., 5/20 | V Softball | Coginchaug | Away - Varsity Softball Field @ CRHS [Directions] | W 5-0 | 2:15pm | |
| Wed., 5/20 | JV Softball | Coginchaug | Away - JV Softball Field @ CRHS [Directions] | 4:00 p.m. | ||
| Tue., 5/26 | V Boys Golf | Sacred Heart | Away - Waterbury CC | Holy Cross-174 | ||
| Wed., 5/27 | V Boys Golf | Sacred Heart | Away - East Mountain | Holy Cross-175 Sacred Heart-186 | ||
| Wed., 5/27 | V Boys Outdoor Track | NVL Championships | Away - Naugatuck High School | 1:30 p.m. | 12:00pm | |
| Wed., 5/27 | V Girls Outdoor Track | NVL Championships | Away - Naugatuck High School | 1:30 p.m. | ||
| Thu., 5/28 | V Boys Outdoor Track | NVL JV Meet | Away - TBA | 3:30 p.m. | 2:15pm | |
| Thu., 5/28 | V Girls Outdoor Track | NVL JV Meet | Away - TBA | 3:30 p.m. | ||
| Sat., 5/30 | V Boys Lacrosse | Tolland | Home - Holy Cross HS [Directions] | L 6-14 | ||
| Mon., 6/1 | V Boys Golf | Crosby | Away - East Mountain [Directions] | Holy Cross-174 | ||
| Wed., 6/3 | V Baseball | Litchfield | Home - Holy Cross HS [Directions] | W 2-1 | ||
| Wed., 6/3 | V Boys Golf | Notre Dame-West Haven | Home - Waterbury CC [Directions] | Cancelled | ||
| Wed., 6/3 | V Softball | Housatonic Regional | Home - Holy Cross HS [Directions] | W 6-0 | ||
| Thu., 6/4 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 2:30 p.m. | 1:15pm | |
| Thu., 6/4 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 2:30 p.m. | 1:15pm | |
| Thu., 6/4 | V Boys Golf | NVL Championships | Away - Watertown CC | TBA | ||
| Thu., 6/4 | V Softball | St. Paul Catholic | Home - Holy Cross HS [Directions] | W 10-2 | ||
| Thu., 6/4 | V Softball | St. Paul Catholic | Home - Holy Cross HS [Directions] | 3:00 p.m. | ||