| Holy Cross 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 646 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Wolcott | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | Torrington | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | TBA | 9:15am | |
| TBA | JV Baseball | Crosby | Away - Crosby HS [Directions] | TBA | 2:30pm | |
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | ||
| TBA | JV Baseball | Seymour | Away - French Park [Directions] | TBA | 2:15pm | |
| TBA | JV Baseball | Naugatuck | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | St. Paul Catholic | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | Torrington | Away - Torrington High School [Directions] | TBA | 9:30am | |
| TBA | JV Baseball | Crosby | Home - HCHS [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Home - HCHS [Directions] | TBA | ||
| TBA | FR Baseball | Wilby | Home - Upper Murray Park [Directions] | TBA | ||
| TBA | FR Baseball | Torrington | Away - Torrington High School [Directions] | TBA | ||
| TBA | FR Baseball | Wilby | Home - Upper Murray Park [Directions] | TBA | ||
| TBA | FR Boys Basketball | Crosby | Away - Crosby HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Kennedy | Home - Holy Cross HS [Directions] | TBA | ||
| TBA | JV Boys Lacrosse | Watertown | Home - HCHS [Directions] | TBA | ||
| TBA | JV Boys Soccer | Ansonia | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | TBA | 2:30pm | |
| TBA | JV Boys Soccer | Wolcott | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Boys Soccer | Torrington | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | FR Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | TBA | 2:30pm | one way |
| TBA | JV Girls Lacrosse | Watertown | Home - Holy Cross HS [Directions] | TBA | ||
| TBA | JV Girls Lacrosse | Watertown | Home - Holy Cross HS [Directions] | TBA | ||
| TBA | JV Girls Lacrosse | Valley Regional | Away - Valley Regional High School [Directions] | Cancelled | ||
| TBA | JV Girls Soccer | Torrington | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Soccer | Sacred Heart | Home - Upper Murray Park [Directions] | TBA | ||
| TBA | JV Girls Soccer | Torrington | Away - Torrington High School [Directions] | TBA | 2:15pm | |
| TBA | JV Girls Soccer | Derby | 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 | Watertown | Away - Veterans Park [Directions] | TBA | ||
| TBA | JV Softball | Immaculate | Home - Holy Cross HS [Directions] | 11:00 a.m. | ||
| TBA | JV Softball | Derby | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Softball | Wilby | Away - Bucks Hill Park [Directions] | TBA | ||
| TBA | JV Softball | Ansonia | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Softball | Seymour | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 9:30am | |
| TBA | JV Softball | Wilby | Home - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Softball | Kennedy | Away - Town Plot Park [Directions] | TBA | ||
| TBA | FR Softball | Pomperaug | Home - Holy Cross HS [Directions] | TBA | ||
| TBA | FR Softball | Naugatuck | Away - Breen Field [Directions] | TBA | no bus | |
| TBA | FR Softball | New Milford | Home - Lower Murray Park [Directions] | TBA | ||
| Tue., 8/27 | V Girls Soccer | Brookfield (Scrim.) | Home - HCHS [Directions] | 3:45 p.m. | ||
| Thu., 8/29 | V Boys Soccer | Litchfield (Scrim.) | Home - Holy Cross HS [Directions] | 3:45 p.m. | ||
| Thu., 8/29 | V Girls Soccer | Housatonic Regional (Scrim.) | Home - HCHS [Directions] | 4:00 p.m. | ||
| Fri., 8/30 | V Girls Volleyball | Berlin (Scrim.) | Home - HCHS [Directions] | 3:30 p.m. | ||
| Tue., 9/3 | V Boys Soccer | Wamogo (Scrim.) | Home - HCHS [Directions] | 3:45 p.m. | ||
| Tue., 9/3 | V Girls Soccer | Wamogo (Scrim.) | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Fri., 9/6 | V Girls Swimming and Diving | NVL Indicational | Away - Kennedy HS | 4:00 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Mercy Invitational | Away - Mercy HS | 3:30 p.m. | 2:15pm | |
| Tue., 9/10 | V Boys Soccer | Seymour | Away - Seymour High Main Field [Directions] | L 1-0 | 4:30pm | |
| Tue., 9/10 | FR Boys Soccer | Naugatuck | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | Mercy Invitational | Away - Mercy HS | 3:30 p.m. | ||
| Tue., 9/10 | V Girls Soccer | Seymour | Home - Holy Cross HS [Directions] | W 1-0 | ||
| Tue., 9/10 | FR Girls Soccer | Naugatuck | Home - Upper Murray Park [Directions] | 3:45 p.m. | 2:30pm | |
| Tue., 9/10 | V Girls Volleyball | Crosby | Away - Crosby HS [Directions] | W 3-0 | 2:30pm | |
| Tue., 9/10 | JV Girls Volleyball | Crosby | Away - Crosby HS [Directions] | 4:30 p.m. | ||
| Wed., 9/11 | JV Boys Soccer | Seymour | Away - Bungay School [Directions] | 3:45 p.m. | 2:30pm | |
| Wed., 9/11 | JV Girls Soccer | Seymour | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Thu., 9/12 | FR Football | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 3:45 p.m. | 2:15pm | |
| Thu., 9/12 | V Boys Soccer | Watertown | Home - Holy Cross HS [Directions] | W 5-0 | ||
| Thu., 9/12 | JV Boys Soccer | Watertown | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Thu., 9/12 | JV Girls Soccer | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 2:30pm | |
| Thu., 9/12 | V Girls Volleyball | Naugatuck | Away - Naugatuck High School [Directions] | L 3-0 | 2:30pm | |
| Thu., 9/12 | JV Girls Volleyball | Naugatuck | Away - Naugatuck High School [Directions] | 6:00 p.m. | ||
| Fri., 9/13 | V Football | Watertown | Home - Municipal Stadium (Wtby) [Directions] | W 29-7 | 5:40pm | |
| Fri., 9/13 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | L 5-1 | 2:00pm | |
| Fri., 9/13 | V Girls Swimming and Diving | Woodland | Home - Kennedy HS [Directions] | Woodland 97 HC 82 | ||
| Sat., 9/14 | V Boys Cross Country | Windham Inv. | Away - Windham | TBA | tba | |
| Sat., 9/14 | JV Football | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 10:00 a.m. | 8:45am | |
| Sat., 9/14 | V Girls Cross Country | Windham Inv. | Away - Windham | TBA | ||
| Sat., 9/14 | JV Girls Volleyball | Immaculate | Home - HCHS [Directions] | 11:30 a.m. | ||
| Sat., 9/14 | FR Girls Volleyball | Immaculate | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Mon., 9/16 | V Boys Soccer | Jonathan Law | Away - Jonathan Law Turf Field [Directions] | W 5-2 | 4:00pm | |
| Tue., 9/17 | V Boys Cross Country | Naugatuck, Torrington, Crosby | Home - Holy Cross HS [Directions] | Naugy 17 HC 44 Torr 19 HC 36 HC 25 Cro 32 | ||
| Tue., 9/17 | FR Boys Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 3:45 p.m. | 2:30pm | |
| Tue., 9/17 | V Girls Cross Country | Naugatuck, Torrington, Crosby | Home - Holy Cross HS [Directions] | Naug 24 HC 35 HC 19 Tor 42 HC 17 Cro 46 | ||
| Tue., 9/17 | FR Girls Soccer | Masuk | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Girls Swimming and Diving | Berlin | Home - Kennedy HS [Directions] | Berlin 101 HC 77 | ||
| Tue., 9/17 | V Girls Volleyball | Torrington | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Tue., 9/17 | JV Girls Volleyball | Torrington | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 9/18 | V Boys Soccer | Ansonia | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Wed., 9/18 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | W 4-3 | 2:30pm | |
| Wed., 9/18 | V Girls Volleyball | Nonnewaug | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Wed., 9/18 | JV Girls Volleyball | Nonnewaug | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Thu., 9/19 | FR Football | Crosby | Away - Crosby HS [Directions] | 3:00 p.m. | ||
| Thu., 9/19 | JV Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:45 p.m. | 2:30pm | |
| Fri., 9/20 | V Football | Derby | Away - Ryan Athletic Complex-Deflippo Field [Directions] | L 14-19 | 5:15pm | |
| Fri., 9/20 | V Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | W 3-0 | 2:30pm | |
| Fri., 9/20 | V Girls Soccer | Woodland | Home - Holy Cross HS [Directions] | W 2-1 | ||
| Fri., 9/20 | V Girls Swimming and Diving | Seymour | Home - Kennedy HS [Directions] | Sey 94 HC 74 | ||
| Fri., 9/20 | V Girls Volleyball | Kennedy | Home - Holy Cross HS [Directions] | W 3-2 | ||
| Fri., 9/20 | JV Girls Volleyball | Kennedy | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Sat., 9/21 | JV Football | Derby | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 9/21 | JV Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 10:30 a.m. | 9:30am | |
| Sat., 9/21 | FR Boys Soccer | Newtown | Away - Newtown High School Practice Field [Directions] | 9:00 a.m. | 7:45am | |
| Sat., 9/21 | JV Girls Soccer | Woodland | Home - Upper Murray Park [Directions] | 12:00 p.m. | ||
| Sat., 9/21 | FR Girls Soccer | Newtown | Home - Upper Murray Park [Directions] | 9:00 a.m. | ||
| Mon., 9/23 | V Boys Soccer | Naugatuck | Home - Holy Cross HS [Directions] | L 4-0 | ||
| Mon., 9/23 | V Girls Soccer | Naugatuck | Away - Naugatuck High School [Directions] | L 8-0 | 4:35pm | |
| Mon., 9/23 | JV Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:30pm | |
| Tue., 9/24 | V Boys Cross Country | Woodland, Wolcott, St. Paul Catholic | Away - WRHS [Directions] | Wood 19 HC 41 HC 22 Wol 34 HC 27 SP 28 | 2:15pm | |
| Tue., 9/24 | JV Boys Soccer | Naugatuck | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Woodland, Wolcott, St. Paul Catholic | Away - WRHS [Directions] | Wood 15 HC 49 Wol 19 HC 36 SP 24 HC 32 | ||
| Tue., 9/24 | V Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | W 3-0 | 3:00pm | |
| Tue., 9/24 | JV Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Wed., 9/25 | FR Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | Cancelled | 4:30pm | |
| Wed., 9/25 | V Boys Soccer | Crosby | Away - Crosby HS [Directions] | W 3-0 | 2:30pm | |
| Wed., 9/25 | V Girls Soccer | Watertown | Home - Holy Cross HS [Directions] | L 4-1 | ||
| Wed., 9/25 | JV Girls Soccer | Watertown | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Wed., 9/25 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | L 3-1 | 2:30pm | |
| Wed., 9/25 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 4:45 p.m. | ||
| Thu., 9/26 | JV Boys Soccer | Crosby | Away - Crosby HS [Directions] | 3:30 p.m. | 2:30pm | |
| Fri., 9/27 | V Football | Ansonia | Home - Municipal Stadium (Wtby) [Directions] | L 13-62 | 5:40pm | |
| Fri., 9/27 | V Boys Soccer | Wilby | Away - Municipal Stadium [Directions] | W 1-0 | 1:45pm | |
| Fri., 9/27 | FR Boys Soccer | New Milford | Away - NMHS [Directions] | 3:45 p.m. | 2:30pm | |
| Fri., 9/27 | V Girls Swimming and Diving | Torrington | Away - Torrington Y [Directions] | Torrington 93 HC 76 | 6:15pm | |
| Fri., 9/27 | V Girls Volleyball | Seymour | Home - Holy Cross HS [Directions] | L 3-1 | ||
| Fri., 9/27 | JV Girls Volleyball | Seymour | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Sat., 9/28 | JV Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 10:00 a.m. | 8:30am | |
| Sat., 9/28 | JV Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | 10:00 a.m. | ||
| Sat., 9/28 | V Girls Soccer | Valley Regional | Home - Holy Cross HS [Directions] | L 5-0 | ||
| Mon., 9/30 | V Boys Soccer | Kennedy | Home - Municipal Stadium (Wtby) [Directions] | W 3-0 | ||
| Mon., 9/30 | JV Girls Soccer | Valley Regional | Away - Valley Regional High School [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 10/1 | V Boys Cross Country | Watertown, Kennedy | Away - Veterans Park [Directions] | Wat 17 HC 46 Ken 19 HC 36 Der 26 HC 29 | 2:15pm | |
| Tue., 10/1 | FR Boys Soccer | Pomperaug | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Watertown, Kennedy, Derby | Away - Veterans Park [Directions] | Wat 17 HC 45 Ken 21 HC 39 Der 25 HC 30 | ||
| Tue., 10/1 | V Girls Soccer | Sacred Heart | Away - Hamilton Park | W 7-5 | 2:30pm | |
| Tue., 10/1 | FR Girls Soccer | Pomperaug | Away - PHS Soccer Field [Directions] | 3:45 p.m. | 2:30pm | |
| Tue., 10/1 | V Girls Swimming and Diving | Suffield | Home - Kennedy HS [Directions] | Suffield 92 HC 78 | ||
| Tue., 10/1 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 3-0 | 2:15pm | |
| Tue., 10/1 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:45 p.m. | ||
| Wed., 10/2 | JV Boys Soccer | Kennedy | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Wed., 10/2 | JV Girls Soccer | Sacred Heart | Away - Hamilton Park | 3:45 p.m. | 2:30pm | |
| Thu., 10/3 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 2-0 | 2:15pm | |
| Thu., 10/3 | V Girls Volleyball | Northwestern | Home - Holy Cross HS [Directions] | W 3-1 | ||
| Thu., 10/3 | JV Girls Volleyball | Northwestern | Home - Holy Cross HS [Directions] | 5:45 p.m. | ||
| Fri., 10/4 | V Football | Sacred Heart | Away - Municipal Stadium | W 55-24 | 5:40pm | |
| Fri., 10/4 | V Boys Soccer | St. Paul Catholic | Home - Holy Cross HS [Directions] | L 2-1 | ||
| Fri., 10/4 | JV Boys Soccer | St. Paul Catholic | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Fri., 10/4 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Kennedy HS [Directions] | HC 98 SP 76 | ||
| Fri., 10/4 | V Girls Volleyball | Woodland | Home - Holy Cross HS [Directions] | L 3-1 | ||
| Fri., 10/4 | JV Girls Volleyball | Woodland | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Sat., 10/5 | V Boys Cross Country | Wickham Inv | Away - Wickham Park | TBA | tba | |
| Sat., 10/5 | FR Boys Soccer | Naugatuck | Away - Naugatuck High School [Directions] | 9:00 a.m. | ||
| Sat., 10/5 | V Girls Cross Country | Wickham Inv | Away - Wickham Park | TBA | ||
| Sat., 10/5 | V Girls Soccer | Morgan | Away - Indian River Complex [Directions] | L 3-1 | 12:00pm | |
| Sat., 10/5 | FR Girls Soccer | Naugatuck | Home - Upper Murray Park [Directions] | 9:00 a.m. | ||
| Mon., 10/7 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | W 6-0 | 2:30pm | |
| Mon., 10/7 | V Girls Soccer | Derby | Home - Holy Cross HS [Directions] | W 5-0 | ||
| Mon., 10/7 | FR Girls Volleyball | Pomperaug | Away - PHS Main Gym [Directions] | 4:30 p.m. | 3:30pm | |
| Tue., 10/8 | V Boys Cross Country | Wilby, Seymour, Sacred Heart | Away - Montoe Park [Directions] | HC 22 SH 37 HC 19 SEY 37 HC 15 WIL 50 | 2:15pm | |
| Tue., 10/8 | FR Boys Soccer | Masuk | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | Wilby, Seymour, Sacred Heart | Away - Montoe Park [Directions] | HC 23 SH 32 HC 24 SEY 35 HC 15 WIL 50 | ||
| Tue., 10/8 | FR Girls Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 10/8 | V Girls Volleyball | Ansonia | Home - Holy Cross HS [Directions] | L 3-1 | ||
| Tue., 10/8 | JV Girls Volleyball | Ansonia | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 10/9 | V Boys Soccer | Torrington | Away - Torrington High School [Directions] | L 3-1 | 4:30pm | |
| Wed., 10/9 | JV Boys Soccer | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | 2:15pm | |
| Wed., 10/9 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 3-0 | 2:30pm | |
| Wed., 10/9 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 4:45 p.m. | ||
| Thu., 10/10 | FR Football | Kennedy | Home - Holy Cross HS [Directions] | Cancelled | ||
| Thu., 10/10 | V Girls Volleyball | Crosby | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Thu., 10/10 | JV Girls Volleyball | Crosby | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Fri., 10/11 | V Football | Kennedy | Away - Municipal Stadium [Directions] | W 43-6 | 5:40pm | |
| Fri., 10/11 | V Boys Soccer | Wolcott | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Fri., 10/11 | V Girls Soccer | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | W 2-1 | 2:30pm | |
| Fri., 10/11 | V Girls Swimming and Diving | Watertown | Home - Kennedy HS [Directions] | Wat 92 HC 80 | ||
| Sat., 10/12 | JV Girls Soccer | Wolcott | Away - Wolcott High School, Lower Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | FR Girls Volleyball | Pomperaug | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Mon., 10/14 | JV Football | Kennedy | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Tue., 10/15 | V Boys Soccer | Sacred Heart | Away - Bucks Hill Park | W 3-1 | 2:30pm | |
| Tue., 10/15 | V Girls Soccer | Sacred Heart | Home - Municipal Stadium (Wtby) [Directions] | W 3-0 | ||
| Tue., 10/15 | V Girls Swimming and Diving | Kennedy | Home - Kennedy HS [Directions] | HC 98 Ken 82 | ||
| Tue., 10/15 | V Girls Volleyball | Bethel | Away - @ Bethel High School [Directions] | L 3-0 | 2:15pm | |
| Tue., 10/15 | JV Girls Volleyball | Bethel | Away - @ Bethel High School [Directions] | 3:30 p.m. | ||
| Wed., 10/16 | V Boys Cross Country | NVL Championships | Away - Veterans Park | 2:15 p.m. | 1:00pm | |
| Wed., 10/16 | JV Boys Soccer | Sacred Heart | Away - Bucks Hill Park | 3:45 p.m. | 2:30pm | |
| Wed., 10/16 | V Girls Cross Country | NVL Championships | Away - Veterans Park | 2:15 p.m. | ||
| Wed., 10/16 | V Girls Soccer | Torrington | Home - Holy Cross HS [Directions] | W 3-1 | ||
| Wed., 10/16 | V Girls Volleyball | Naugatuck | Home - Holy Cross HS [Directions] | L 3-1 | ||
| Wed., 10/16 | JV Girls Volleyball | Naugatuck | Home - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Thu., 10/17 | V Boys Soccer | Naugatuck | Away - Naugatuck High School [Directions] | L 2-0 | 4:45pm | |
| Fri., 10/18 | V Boys Cross Country | Woodland Novice | Away - WRHS | 3:30 p.m. | 2:15pm | |
| Fri., 10/18 | FR Boys Soccer | Newtown | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | V Girls Cross Country | Woodland Novice | Away - WRHS | 3:30 p.m. | ||
| Fri., 10/18 | FR Girls Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | 2:30pm | |
| Fri., 10/18 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy High School Pool | SH 95 HC 80 | ||
| Fri., 10/18 | V Girls Volleyball | Torrington | Away - Torrington High School [Directions] | L 0-3 | 2:30pm | |
| Fri., 10/18 | JV Girls Volleyball | Torrington | Away - Torrington High School [Directions] | 4:45 p.m. | ||
| Sat., 10/19 | V Football | Weston | Away - WHS Stadium Field [Directions] | W 37-7 | 10:30am | |
| Sat., 10/19 | FR Boys Soccer | Watertown | Home - Lower Murray Park [Directions] | 9:00 a.m. | ||
| Sat., 10/19 | V Girls Soccer | Naugatuck | Home - Municipal Stadium (Wtby) [Directions] | L 0-2 | ||
| Sat., 10/19 | JV Girls Soccer | Naugatuck | Home - Upper Murray Park [Directions] | 1:00 p.m. | ||
| Mon., 10/21 | V Boys Cross Country | City Meet | Away - Montoe | 3:30 p.m. | 2:15pm | |
| Mon., 10/21 | FR Football | Weston | Home - Holy Cross HS [Directions] | 4:15 p.m. | ||
| Mon., 10/21 | V Girls Cross Country | City Meet | Away - Montoe | 3:30 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Torrington | Away - Torrington High School [Directions] | W 5-3 | 4:30pm | |
| Mon., 10/21 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 1-3 | 2:30pm | |
| Mon., 10/21 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | ||
| Tue., 10/22 | V Boys Soccer | Torrington | Home - Municipal Stadium (Wtby) [Directions] | L 0-3 | ||
| Tue., 10/22 | FR Boys Soccer | New Milford | Home - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 10/22 | FR Girls Soccer | New Milford | Away - NMHS [Directions] | 3:45 p.m. | 2:30pm | |
| Wed., 10/23 | FR Football | Torrington | Away - Torrington High School [Directions] | Cancelled | 2:15pm | |
| Wed., 10/23 | JV Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 a.m. | 2:30pm | |
| Wed., 10/23 | V Girls Volleyball | Wilby | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Wed., 10/23 | JV Girls Volleyball | Wilby | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Thu., 10/24 | V Football | Torrington | Home - Municipal Stadium (Wtby) [Directions] | W 41-21 | 4:40pm | |
| Thu., 10/24 | FR Boys Soccer | Pomperaug | Away - PHS Soccer Field [Directions] | 3:45 p.m. | 2:30pm | |
| Thu., 10/24 | FR Girls Soccer | Pomperaug | Home - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Thu., 10/24 | V Girls Swimming and Diving | Naugatuck, Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:00pm | |
| Thu., 10/24 | V Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | W 3-1 | 2:15pm | |
| Thu., 10/24 | JV Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/25 | JV Football | Torrington | Away - Torrington High School [Directions] | 3:45 p.m. | 2:00pm | |
| Sat., 10/26 | FR Boys Soccer | Torrington | Home - Lower Murray Park [Directions] | 10:00 a.m. | ||
| Mon., 10/28 | FR Boys Soccer | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | 2:30pm | |
| Mon., 10/28 | FR Girls Soccer | Watertown | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Tue., 10/29 | V Girls Swimming and Diving | NVL Trials | Away - Kennedy HS | 4:00 p.m. | ||
| Wed., 10/30 | V Girls Swimming and Diving | NVL Diving | Away - Kennedy HS | 6:00 p.m. | ||
| Fri., 11/1 | V Football | Woodland | Home - Municipal Stadium (Wtby) [Directions] | W 37-18 | 5:40pm | |
| Sat., 11/2 | JV Football | Woodland | Away - Woodland Football Field [Directions] | 10:00 a.m. | 8:30am | |
| Sat., 11/2 | V Girls Swimming and Diving | NVL Finals | Away - Kennedy HS | 4:00 p.m. | ||
| Mon., 11/4 | V Girls Soccer | Seymour | Home - Holy Cross HS [Directions] | W 3-0 | ||
| Mon., 11/4 | V Girls Volleyball | Coginchaug | Away - CHS [Directions] | L 3-2 | 3:30pm | |
| Tue., 11/5 | V Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | L 3-1(ot) | 4:00pm | |
| Wed., 11/6 | V Girls Soccer | Waterford | Away - Alumni Turf Field [Directions] | L 0-4 | 2:30pm | |
| Thu., 11/7 | V Football | Naugatuck | Home - Municipal Stadium (Wtby) [Directions] | L 20-56 | 4:40pm | |
| Thu., 11/7 | FR Football | Naugatuck | Away - Naugatuck High School [Directions] | Cancelled | 2:15pm | |
| Sat., 11/9 | JV Football | Naugatuck | Away - Naugatuck High School [Directions] | 10:00 a.m. | 8:45am | |
| Sat., 11/16 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 49-46 | 11:30am | |
| Mon., 11/18 | FR Football | St. Paul Catholic | Home - Holy Cross HS [Directions] | 3:15 p.m. | ||
| Thu., 11/21 | FR Football | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | Cancelled | TBA | |
| Sat., 11/23 | JV Football | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | 10:00 a.m. | 8:30am | |
| Thu., 11/28 | V Football | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | W 39-38 | 8:00am | |
| Sat., 12/7 | V Boys Basketball | Guilford (Scrim.) | Home - Holy Cross HS [Directions] | 2:00 p.m. | ||
| Sat., 12/7 | V Boys Basketball | Maloney (Scrim.) | Home - Holy Cross HS [Directions] | 2:00 p.m. | ||
| Sat., 12/7 | V Wrestling | Xavier (Scrim.) | Away [Directions] | 9:00 a.m. | 7:30 a.m. | |
| Sat., 12/7 | V Girls Ice Hockey | Daniel Hand Coop | Home - Lou Astorino Ice Rink [Directions] | W 8-0 | ||
| Mon., 12/9 | V Girls Basketball | Mercy (Scrim.) | Away - Mercy HS [Directions] | 3:30 p.m. | 2:00pm | |
| Wed., 12/11 | V Girls Basketball | Naugatuck | Home - Holy Cross HS [Directions] | W 59-29 | ||
| Wed., 12/11 | JV Girls Basketball | Naugatuck | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Wed., 12/11 | FR Girls Basketball | Naugatuck | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 12/13 | V Boys Swimming and Diving | NVL Preseason Indicational | Away - Kennedy HS | 4:00 p.m. | ||
| Sat., 12/14 | V Wrestling | New Milford (Scrim.) | Away - NMHS [Directions] | 9:00 a.m. | 7:15am | |
| Sat., 12/14 | JV Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Rink [Directions] | Cancelled | Yes | |
| Mon., 12/16 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | W 52-39 | ||
| Mon., 12/16 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:30 p.m. | ||
| Wed., 12/18 | V Boys Swimming and Diving | Avon | Home - Kennedy HS [Directions] | Avon 103 HC 66 | ||
| Wed., 12/18 | V Wrestling | Holy Cross | Away - Holy Cross HS [Directions] | W 66-18 [Detailed Results] | 2:15 p.m. | |
| Wed., 12/18 | V Wrestling | Derby/Oxford/Holy Cross | Home - Holy Cross HS [Directions] | Derby 60 HC 16 | ||
| Wed., 12/18 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 56-32 | 4:15pm | one way |
| Wed., 12/18 | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 3:30 p.m. | 2:15pm | |
| Thu., 12/19 | V Boys Basketball | Wolcott | Home - Holy Cross HS [Directions] | W 70-50 | ||
| Thu., 12/19 | JV Boys Basketball | Wolcott | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | V Boys Basketball | Derby | Away - Derby High -A. Vitello Gymnasium [Directions] | W 76-69 | 4:15pm | |
| Fri., 12/20 | JV Boys Basketball | Derby | Away - Derby High -A. Vitello Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Wolcott | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 12/20 | V Girls Basketball | Derby | Home - Holy Cross HS [Directions] | W 57-35 | ||
| Fri., 12/20 | JV Girls Basketball | Derby | Home - Holy Cross HS [Directions] | 7:00 p.m. | ||
| Sat., 12/21 | FR Boys Basketball | Pomperaug | Home - Holy Cross HS [Directions] | 11:00 a.m. | ||
| Sat., 12/21 | V Boys Indoor Track | New Haven Invitational | Away - New Haven Athletic | 9:00 a.m. | 7:15am | |
| Sat., 12/21 | V Wrestling | Derby Invitational | Home - Derby High- A. Vitello Gymnasium [Directions] | 2nd Place [Detailed Results] | ||
| Sat., 12/21 | V Wrestling | Pomperaug Tournament | Away - PHS | 9:30 a.m. | 7:45am | |
| Sat., 12/21 | FR Girls Basketball | Sacred Heart | Away - SHHS Alumni Hall | 12:00 p.m. | ||
| Sat., 12/21 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - SoNo Ice House, South Norwalk [Directions] | W 6-0 | 9:30 am | |
| Sat., 12/21 | V Girls Indoor Track | NH Invite | Away - NH Athletic | 9:00 a.m. | ||
| Mon., 12/23 | V Boys Basketball | Torrington | Home - Holy Cross HS [Directions] | L 55-69 | ||
| Mon., 12/23 | JV Boys Basketball | Torrington | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Mon., 12/23 | FR Boys Basketball | Torrington | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Mon., 12/23 | V Wrestling | Platt Tech | Home - Derby High- A. Vitello Gymnasium [Directions] | W 54-21 [Detailed Results] | ||
| Mon., 12/23 | V Wrestling | Nonnewaug JV Tournament | Away - NHS | TBA | tba | |
| Mon., 12/23 | JV Wrestling | Nonnewaug JV Tournament | Away | Cancelled | 7:30 a.m. | |
| Mon., 12/23 | V Girls Basketball | Torrington | Away - Torrington High School [Directions] | W 52-43 | 4:15pm | |
| Mon., 12/23 | JV Girls Basketball | Torrington | Away - Torrington High School [Directions] | 5:15 p.m. | ||
| Mon., 12/23 | FR Girls Basketball | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | 2:30pm | |
| Fri., 12/27 | V Boys Basketball | Wilby | Home - Holy Cross HS [Directions] | L 44-74 | ||
| Fri., 12/27 | JV Boys Basketball | Wilby | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 12/27 | FR Boys Basketball | Wilby | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 12/27 | V Wrestling | Glastonbury JV Tournament | Away - GHS | TBA | tba | |
| Fri., 12/27 | V Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | W 62-19 | ||
| Fri., 12/27 | JV Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 2:15 p.m. | ||
| Sat., 12/28 | V Wrestling | Glastonbury Duals | Away | 3rd Place
Derby 44 Glastonbury 33
Derby 49 Terryville 28
Derby 38 Middletown 36
Berlin 40 Derby 35 [Detailed Results] | 7:30 a.m. | |
| Sat., 12/28 | JV Wrestling | Glastonbury JV Tournament | Away | 10:00 a.m. | JV tournament same time and date as Varsity | |
| Sat., 12/28 | FR Girls Basketball | Pomperaug | Home - Holy Cross HS [Directions] | 9:30 a.m. | ||
| Sat., 12/28 | V Girls Ice Hockey | New Canaan | Home - Lou Astorino Ice Rink [Directions] | L 0-1 | ||
| Tue., 12/31 | V Wrestling | Canton | Home - Derby High- A. Vitello Gymnasium [Directions] | Cancelled | ||
| Thu., 1/2 | JV Girls Ice Hockey | Simsbury | Home - Lou Astorino Ice Rink [Directions] | Cancelled | ||
| Sat., 1/4 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | HC 96 Gilbert 76 | 2:45pm | |
| Sat., 1/4 | V Wrestling | Somers, Brookfield/Shepaug, St. Paul Catholic | Home - Derby High- A. Vitello Gymnasium [Directions] | Derby 84. St. Paul 0
Derby 84. Brookfield 0 [Detailed Results] | ||
| Sat., 1/4 | V Wrestling | Shelton Duals | Away - SHS | 9:00 a.m. | 7:15am | |
| Sat., 1/4 | FR Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 12:00 p.m. | ||
| Sat., 1/4 | V Girls Ice Hockey | Lauralton Hall | Away - Wonderland of Ice, Bridgeport [Directions] | W 9-0 | 11:15 am | |
| Tue., 1/7 | V Boys Basketball | Woodland | Home - Holy Cross HS [Directions] | W 51-45 | ||
| Tue., 1/7 | JV Boys Basketball | Woodland | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 1/7 | FR Boys Basketball | Woodland | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 1/7 | V Girls Basketball | Woodland | Away - Woodland High School Gym [Directions] | W 50-33 | 4:15pm | |
| Tue., 1/7 | JV Girls Basketball | Woodland | Away - Woodland High School Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/8 | V Wrestling | Haddam-Killingworth | Home - Derby High- A. Vitello Gymnasium [Directions] | W 39-27 [Detailed Results] | ||
| Wed., 1/8 | V Wrestling | Northwestern | Away - Northwestern Gym [Directions] | HC 30 NW 12 | 4:45pm | |
| Wed., 1/8 | V Girls Basketball | Ansonia | Home - Holy Cross HS [Directions] | W 68-39 | ||
| Wed., 1/8 | JV Girls Basketball | Ansonia | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Thu., 1/9 | V Boys Basketball | Ansonia | Away - Ansonia High School [Directions] | W 48-23 | 4:15pm | |
| Thu., 1/9 | JV Boys Basketball | Ansonia | Away - Ansonia High School [Directions] | 4:00 p.m. | ||
| Thu., 1/9 | V Boys Swimming and Diving | Naugatuck | Home - Kennedy HS [Directions] | Naugy 91 HC 89 | 4:45pm | |
| Fri., 1/10 | V Boys Basketball | Crosby | Away - Crosby HS [Directions] | L 58-84 | ||
| Fri., 1/10 | JV Boys Basketball | Crosby | Away - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Indoor Track | McGreavy Invitational | Away - Wesleyan U | 4:00 p.m. | 2:15pm | |
| Fri., 1/10 | V Girls Basketball | Crosby | Home - Holy Cross HS [Directions] | W 71-35 | ||
| Fri., 1/10 | JV Girls Basketball | Crosby | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | V Girls Ice Hockey | West Haven/SHA | Home - Lou Astorino Ice Rink [Directions] | W 9-3 | ||
| Fri., 1/10 | V Girls Indoor Track | McGreavy Inv | Away - NH Athletic | 4:00 p.m. | ||
| Sat., 1/11 | V Wrestling | Lawless Tournament | Away | 3rd Place [Detailed Results] | 8:00 a.m. | |
| Sat., 1/11 | V Wrestling | Somers Duals | Away - SHS | 10:00 a.m. | 8:00am | |
| Sat., 1/11 | FR Girls Basketball | Immaculate | Home - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sat., 1/11 | V Girls Ice Hockey | Hall/Conard | Home - Lou Astorino Ice Rink [Directions] | L 1-0 | Conard/Hall | |
| Tue., 1/14 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 25-39 | ||
| Tue., 1/14 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | 2:30pm | |
| Tue., 1/14 | V Boys Swimming and Diving | Watertown | Home - Kennedy HS [Directions] | Watertown 92 HC 88 | ||
| Tue., 1/14 | V Girls Basketball | Kennedy | Home - Holy Cross HS [Directions] | W 77-47 | ||
| Tue., 1/14 | JV Girls Basketball | Kennedy | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | FR Girls Basketball | Kennedy | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 1/14 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | L 3-1 | 3:30 pm | |
| Wed., 1/15 | V Wrestling | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | L 31-30 [Detailed Results] | 4:15 p.m. | |
| Wed., 1/15 | V Wrestling | Seymour | Home - Holy Cross HS [Directions] | 6:30 p.m. | ||
| Fri., 1/17 | V Boys Basketball | Watertown | Home - Holy Cross HS [Directions] | W 53-46 | ||
| Fri., 1/17 | JV Boys Basketball | Watertown | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Watertown | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 1/17 | V Boys Indoor Track | NVL Developmental | Away - Wesleyan University | 4:30 p.m. | 3:30pm | |
| Fri., 1/17 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | Torrington 95 HC 73 | 6:00pm | |
| Fri., 1/17 | JV Wrestling | Pomperaug JV tournament | Away | Cancelled | 7:30 a.m. | |
| Fri., 1/17 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 36-28 | 4:15pm | one way |
| Fri., 1/17 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 3:45 p.m. | 2:30pm | one way |
| Fri., 1/17 | V Girls Indoor Track | NVL Developmental | Away - Wesleyan University | 4:30 p.m. | ||
| Sat., 1/18 | V Boys Swimming and Diving | Northwestern | Home - Kennedy HS [Directions] | NW 100 HC 78 | ||
| Sat., 1/18 | V Wrestling | Gilbert/Torrington, Weston, Seymour | Away - at Gilbert [Directions] | Derby 67 Gilbert 9
Derby 58 Seymour 21 [Detailed Results] | 8:00 a.m. | |
| Sat., 1/18 | V Wrestling | New Milford Tournament | Away - NMHS | 9:30 a.m. | 7:15am | |
| Sat., 1/18 | V Girls Ice Hockey | Simsbury | Away - ISCC, Simbury [Directions] | L 5-2 | 3:30 pm | |
| Wed., 1/22 | V Wrestling | Wolcott Tech | Away - OWTS Gym [Directions] | W 66-6 [Detailed Results] | 4:30 p.m. | |
| Thu., 1/23 | V Boys Basketball | Naugatuck | Home - Holy Cross HS [Directions] | W 41-28 | ||
| Thu., 1/23 | JV Boys Basketball | Naugatuck | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Thu., 1/23 | FR Boys Basketball | Naugatuck | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 1/24 | V Boys Swimming and Diving | HK-Valley | Away - Haddam Killingworth HS [Directions] | HC 89 H-K 79 | 2:15pm | |
| Fri., 1/24 | V Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | W 79-32 | 4:30pm | one way |
| Fri., 1/24 | JV Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | ||
| Fri., 1/24 | FR Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:30pm | one way |
| Fri., 1/24 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks of Shelton [Directions] | W 5-0 | 2:45 pm | |
| Sat., 1/25 | V Boys Basketball | Notre Dame-West Haven | Home - Holy Cross HS [Directions] | L 39-55 | ||
| Sat., 1/25 | JV Boys Basketball | Notre Dame-West Haven | Home - Holy Cross HS [Directions] | 4:15 p.m. | ||
| Sat., 1/25 | FR Boys Basketball | Notre Dame-West Haven | Home - Holy Cross HS [Directions] | 2:30 p.m. | ||
| Sat., 1/25 | V Wrestling | Oxford Tournament | Away - OHS | 8:00 a.m. | tba | |
| Sat., 1/25 | V Wrestling | Valley of Champions Tournament | Away - Oxford HS | 1st Place [Detailed Results] | 8:30 a.m. | |
| Sat., 1/25 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Lou Astorino Ice Rink [Directions] | L 5-4 | ||
| Mon., 1/27 | JV Girls Ice Hockey | Daniel Hand Coop | Home - Lou Astorino Ice Rink [Directions] | 4:15 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | L 41-63 | ||
| Tue., 1/28 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Tue., 1/28 | V Boys Indoor Track | NVL Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | 3:00pm | |
| Tue., 1/28 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 1/28 | V Girls Basketball | Sacred Heart | Home - Holy Cross HS [Directions] | W 50-41 | ||
| Tue., 1/28 | JV Girls Basketball | Sacred Heart | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Girls Basketball | Sacred Heart | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 1/28 | V Girls Ice Hockey | East Catholic Coop | Home - Lou Astorino Ice Rink [Directions] | L 4-2 | ||
| Tue., 1/28 | V Girls Indoor Track | NVL Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Wed., 1/29 | V Wrestling | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | Cancelled | 4:00 p.m. | |
| Wed., 1/29 | V Wrestling | Housatonic Regional | Home - Holy Cross HS [Directions] | 6:30 p.m. | ||
| Wed., 1/29 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | W 11-3 | 6:30 pm | |
| Wed., 1/29 | JV Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | 3:45 p.m. | 2:15 pm | |
| Thu., 1/30 | JV Girls Ice Hockey | West Haven/SHA | Home - Lou Astorino Ice Rink [Directions] | 4:05 p.m. | ||
| Fri., 1/31 | V Boys Basketball | St. Paul Catholic | Home - Holy Cross HS [Directions] | L 50-52 | ||
| Fri., 1/31 | JV Boys Basketball | St. Paul Catholic | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | St. Paul Catholic | Home - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Woodland | Away - Woodland High School Pool [Directions] | HC 90 Woodland 79 | 2:30pm | |
| Fri., 1/31 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 46-38 | 4:00pm | |
| Fri., 1/31 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Fri., 1/31 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 2/1 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 12:00 p.m. | ||
| Sat., 2/1 | V Wrestling | Jonathan Law, Fitch | Away - Jonathan Law New Gym [Directions] | Derby 53 Jonathan Law 20
Derby 84 Housatonic 0
Derby 31 Maloney 39
Derby 75 Vinal Tech 6
Derby 66 Fitch 11 [Detailed Results] | 8:00 a.m. | |
| Sat., 2/1 | V Wrestling | Manchester, Terryville-Thomaston | Away - MHS [Directions] | 10:00 a.m. | 8:00am | |
| Sat., 2/1 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Lou Astorino Ice Rink [Directions] | W 6-1 | ||
| Tue., 2/4 | V Boys Basketball | Torrington | Away - Torrington High School [Directions] | L 70-72 | 4:15pm | |
| Tue., 2/4 | JV Boys Basketball | Torrington | Away - Torrington High School [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Boys Basketball | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | 2:30pm | |
| Tue., 2/4 | V Boys Swimming and Diving | Kennedy | Home - Kennedy HS [Directions] | HC 93 Kennedy 85 | ||
| Tue., 2/4 | V Girls Basketball | Torrington | Home - Holy Cross HS [Directions] | W 50-41 | ||
| Tue., 2/4 | JV Girls Basketball | Torrington | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Girls Basketball | Torrington | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Thu., 2/6 | V Wrestling | Westbrook | Home - Derby High- A. Vitello Gymnasium [Directions] | W 67-11 [Detailed Results] | ||
| Fri., 2/7 | V Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | L 47-49 | ||
| Fri., 2/7 | JV Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | Cancelled | ||
| Fri., 2/7 | V Girls Basketball | Wilby | Home - Holy Cross HS [Directions] | W 74-36 | ||
| Fri., 2/7 | JV Girls Basketball | Wilby | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Lou Astorino Ice Rink [Directions] | W 8-1 | ||
| Sat., 2/8 | V Wrestling | Morgan, Griswold/Wheeler, Granby Memorial | Away - Morgan HS [Directions] | Derby 59 Granby 18
Derby 66 Griswold 15
Derby 42 Morgan 36 [Detailed Results] | 8:00 a.m. | |
| Sat., 2/8 | V Wrestling | EnricoFermi, New Britain, Wethersfield | Home - Holy Cross HS [Directions] | 9:00 a.m. | ||
| Sat., 2/8 | FR Girls Basketball | Immaculate | Away - Mustang Valley [Directions] | Cancelled | 8:45am | |
| Sat., 2/8 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Skating Center [Directions] | W 3-2 | 6:30 pm | |
| Mon., 2/10 | FR Boys Basketball | Crosby | Home - Holy Cross HS [Directions] | 6:30 p.m. | ||
| Mon., 2/10 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Rink [Directions] | W 9-0 | 2:15 pm | |
| Mon., 2/10 | JV Girls Ice Hockey | West Haven/SHA | Away [Directions] | Cancelled | 2:00 pm | |
| Tue., 2/11 | V Boys Basketball | Crosby | Home - Holy Cross HS [Directions] | L 52-80 | ||
| Tue., 2/11 | JV Boys Basketball | Crosby | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | V Boys Swimming and Diving | Seymour | Home - Kennedy HS [Directions] | HC 92 Sey 73 | ||
| Tue., 2/11 | V Girls Basketball | Crosby | Away - Crosby HS [Directions] | W 46-39 | ||
| Tue., 2/11 | JV Girls Basketball | Crosby | Away - Crosby HS [Directions] | 5:30 p.m. | ||
| Wed., 2/12 | V Wrestling | Canton | Home - Derby High Al Vitello Gymnasium [Directions] | W 66-15 [Detailed Results] | ||
| Wed., 2/12 | V Wrestling | Gilbert/Torrington | Away - Gilbert Gym [Directions] | Cancelled | 4:45pm | |
| Wed., 2/12 | V Girls Ice Hockey | Guilford Coop | Home - Lou Astorino Ice Rink [Directions] | W 2-1 | ||
| Fri., 2/14 | V Boys Basketball | Kennedy | Home - Holy Cross HS [Directions] | L 40-41 | ||
| Fri., 2/14 | JV Boys Basketball | Kennedy | Home - Holy Cross HS [Directions] | 5:00 p.m. | ||
| Fri., 2/14 | V Boys Swimming and Diving | Sacred Heart | Home - Kennedy HS [Directions] | 7:00 p.m. | ||
| Fri., 2/14 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 55-50 (OT) | ||
| Fri., 2/14 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | ||
| Mon., 2/17 | JV Wrestling | Class S JV Wrestling Tournament | Away | 9:00 a.m. | 7:30 a.m. | @ Pomperaug HS |
| Mon., 2/17 | V Girls Basketball | Seymour | Home - Holy Cross HS [Directions] | W 68-37 | ||
| Mon., 2/17 | JV Girls Basketball | Seymour | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Mon., 2/17 | FR Girls Basketball | Seymour | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Mon., 2/17 | V Girls Ice Hockey | Hall/Conard | Away - Veterans' Memorial, West Hartford, CT [Directions] | L 2-0 | 5:00 pm | |
| Tue., 2/18 | V Boys Swimming and Diving | Suffield | Away - Windsor Locks High School [Directions] | Cancelled | 2:45pm | |
| Tue., 2/18 | V Girls Ice Hockey | Lauralton Hall | Home - Lou Astorino Ice Rink [Directions] | Cancelled | ||
| Tue., 2/18 | JV Girls Ice Hockey | Branford | Away [Directions] | Cancelled | ||
| Thu., 2/20 | V Girls Basketball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | L 29-55 | 4:00pm | |
| Thu., 2/20 | JV Girls Basketball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/20 | FR Girls Basketball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 3:30 p.m. | 2:15pm | |
| Thu., 2/20 | V Girls Ice Hockey | Simsbury | Home - Lou Astorino Ice Rink [Directions] | L 6-1 | ||
| Fri., 2/21 | V Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | L 41-48 | ||
| Fri., 2/21 | JV Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | ||
| Fri., 2/21 | FR Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:30pm | |
| Fri., 2/21 | V Wrestling | Class S State Championships | Away | 3:30 p.m. | 12:00 p.m. | |
| Sat., 2/22 | V Boys Basketball | Seymour | Away - Seymour High School [Directions] | W 61-35 | 12:30pm | |
| Sat., 2/22 | JV Boys Basketball | Seymour | Away - Seymour High School [Directions] | 1:30 p.m. | ||
| Sat., 2/22 | FR Boys Basketball | Seymour | Away - Seymour High School [Directions] | 12:00 p.m. | 10:45pm | |
| Sat., 2/22 | V Wrestling | Class S State Championships | Away | 9:00 a.m. | 7:00 a.m. | |
| Mon., 2/24 | FR Boys Basketball | Sacred Heart | Home - Holy Cross HS [Directions] | 4:15 p.m. | ||
| Mon., 2/24 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 2/25 | V Boys Basketball | Sacred Heart | Home - Holy Cross HS [Directions] | L 52-69 | ||
| Tue., 2/25 | JV Boys Basketball | Sacred Heart | Home - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 2/25 | JV Girls Ice Hockey | Branford | Home - Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Fri., 2/28 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | 3:00pm | |
| Fri., 2/28 | V Wrestling | State Open Championships | Away - Hillhouse Fieldhouse | 3:30 p.m. | TBA | |
| Sat., 3/1 | V Wrestling | State Open Championships | Away - Hillhouse Fieldhouse | 9:00 a.m. | TBA | |
| Tue., 3/4 | V Girls Ice Hockey | Quarter-Finals | Away - Darien Ice Rink Old Kings Hwy | 7:40 p.m. | 5:00 pm | |
| Wed., 3/5 | V Girls Ice Hockey | Semi-Finals | Away | TBA | Yes | |
| Fri., 3/7 | V Wrestling | New England Championships | Away | 3:30 p.m. | TBA | |
| Sat., 3/8 | V Wrestling | New England Championships | Away | 9:00 a.m. | TBA p.m. | |
| Sat., 3/8 | V Girls Ice Hockey | Championship | Away - Engalls Rink Yale University | TBA | Yes | May 8th or 9th |
| Sat., 3/29 | V Softball | Pomperaug (Scrim.) | Away - Community Softball Field [Directions] | 1:00 p.m. | ||
| Wed., 4/2 | V Baseball | Oxford (Scrim.) | Home - Bucks Hill Park - Waterbury [Directions] | 3:45 p.m. | ||
| Sat., 4/5 | V Baseball | Maloney (Scrim.) | Home - HCHS [Directions] | 11:00 p.m. | ||
| Sat., 4/5 | V Boys Lacrosse | Nonnewaug (Scrim.) | Home - Post U [Directions] | 11:30 a.m. | ||
| Sat., 4/5 | V Girls Lacrosse | Nonnewaug (Scrim.) | Home - Post U [Directions] | 10:00 a.m. | ||
| Mon., 4/7 | V Baseball | New Milford (Scrim.) | Away - New Milford High School [Directions] | 3:45 p.m. | 2:00pm | |
| Wed., 4/9 | V Boys Tennis | Wolcott | Home - HCHS [Directions] | L 7-2 | ||
| Wed., 4/9 | V Softball | Wolcott | Away - George Babcock Field, Wolcott High School [Directions] | W 6-1 | 2:30pm | |
| Wed., 4/9 | JV Softball | Wolcott | Away - Wolcott 2 [Directions] | 4:15 p.m. | ||
| Wed., 4/9 | V Girls Tennis | Wolcott | Away - Wolcott High School [Directions] | L 0-7 | w/softball | |
| Thu., 4/10 | V Baseball | Wolcott | Home - HCHS [Directions] | W 5-4 | ||
| Thu., 4/10 | FR Baseball | Wolcott | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Thu., 4/10 | V Boys Lacrosse | Lewis Mills | Home - Holy Cross HS [Directions] | L 2-18 | ||
| Thu., 4/10 | JV Boys Lacrosse | Lewis Mills | Home - HCHS [Directions] | 5:30 p.m. | ||
| Thu., 4/10 | V Girls Lacrosse | Watertown | Away - WHS Mills Complex [Directions] | W 9-8 | 2:15pm | |
| Thu., 4/10 | V Girls Tennis | Naugatuck | Home - HCHS [Directions] | L 1-6 | ||
| Fri., 4/11 | V Baseball | Derby | Away - Derby -Ryan Athletic Complex-baseball field [Directions] | W 3-1 | 2:15pm | |
| Fri., 4/11 | V Softball | Derby | Home - Huntingdon Field [Directions] | W 15-0 | ||
| Sat., 4/12 | V Baseball | Pomperaug | Away - PHS Baseball Field [Directions] | L 4-5 | tba | |
| Sat., 4/12 | JV Baseball | Derby | Away - Derby -Ryan Athletic Complex-baseball field [Directions] | 10:30 a.m. | 9:30am | |
| Sat., 4/12 | V Softball | Immaculate | Away - Immaculate High School [Directions] | W 2-0 | 9:15am | |
| Mon., 4/14 | V Baseball | Torrington | Home - HCHS [Directions] | W 15-8 | ||
| Mon., 4/14 | FR Baseball | Torrington | Home - Upper Murray Park [Directions] | 11:00 a.m. | ||
| Mon., 4/14 | V Boys Tennis | Torrington | Home - HCHS [Directions] | L 2-7 | ||
| Mon., 4/14 | V Softball | Torrington | Away - Torrington High School [Directions] | L 0-15(5) | 2:15pm | |
| Mon., 4/14 | JV Softball | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | ||
| Mon., 4/14 | V Girls Tennis | Torrington | Away - Torrington High School [Directions] | W 5-2 | w/softball | |
| Wed., 4/16 | V Baseball | Wilby | Away - Waterville park [Directions] | W 4-2 | ||
| Wed., 4/16 | V Softball | Wilby | Away - Huntington Park [Directions] | W 23-5 | ||
| Thu., 4/17 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | L 1-2 | 2:15pm | |
| Thu., 4/17 | JV Baseball | Wilby | Home - HCHS [Directions] | 11:00 a.m. | ||
| Thu., 4/17 | FR Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | ||
| Thu., 4/17 | V Boys Lacrosse | Berlin | Away - Scalise Field - Sage Park [Directions] | L 8-19 | 2:15pm | |
| Thu., 4/17 | JV Boys Lacrosse | Berlin | Away - Scalise Field - Sage Park [Directions] | 4:00 p.m. | ||
| Thu., 4/17 | V Boys Tennis | Sacred Heart | Home - HCHS [Directions] | L 3-6 | ||
| Thu., 4/17 | V Softball | Ansonia | Home - HCHS [Directions] | W 4-3 | ||
| Sat., 4/19 | V Boys Lacrosse | Immaculate | Away - Mustang Valley [Directions] | L 7-13 | 11:00am | |
| Sat., 4/19 | V Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | L 1-14 | 9:30am | |
| Mon., 4/21 | V Baseball | Woodland | Home - HCHS [Directions] | W 6-3 | ||
| Mon., 4/21 | FR Baseball | Woodland | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Mon., 4/21 | V Boys Golf | Woodland | Home - Western Hills [Directions] | HC 191 Wood 202 KEN 257 | ||
| Mon., 4/21 | V Boys Lacrosse | Housatonic Regional | Home - Holy Cross HS [Directions] | W 10-5 | ||
| Mon., 4/21 | V Boys Tennis | Woodland | Home - HCHS [Directions] | W 6-3 | ||
| Mon., 4/21 | V Softball | Woodland | Away - Woodland Softball Field [Directions] | W 6-3 | 2:30pm | |
| Mon., 4/21 | JV Softball | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:30 p.m. | ||
| Mon., 4/21 | V Girls Tennis | Sacred Heart | Away - Fulton Park | W 7-0 | 2:30pm | |
| Tue., 4/22 | JV Baseball | Woodland | Home - HCHS [Directions] | 3:30 p.m. | ||
| Tue., 4/22 | V Boys Golf | Watertown | Away - Crestbrook Park Golf Course [Directions] | HC 189 Wat 193 | ||
| Tue., 4/22 | V Boys Outdoor Track | Kennedy, Watertown, Crosby | Home - HCHS [Directions] | HC 94 Crosby 55 HC 100 Kenn 48 HC 78 Watertown 72 | ||
| Tue., 4/22 | V Girls Lacrosse | Housatonic Regional | Away - Housatonic Field [Directions] | L 7-13 | 2:00pm | |
| Tue., 4/22 | V Girls Outdoor Track | Kennedy, Watertown, Crosby | Home - HCHS [Directions] | HC 88 Kennedy 43 HC 92 Crosby 40 HC 61 Watertown 87 | ||
| Tue., 4/22 | FR Softball | Woodland | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Tue., 4/22 | V Girls Tennis | Crosby | Home - HCHS [Directions] | W 5-1 | ||
| Wed., 4/23 | V Baseball | Crosby | Away - Washington Park [Directions] | W 13-2 | 2:30pm | |
| Wed., 4/23 | V Boys Golf | Wolcott | Away - Farmingbury Country Club [Directions] | HC 170 Wolcott 175 | ||
| Wed., 4/23 | V Boys Tennis | Crosby | Away - Holy Cross HS [Directions] | W 5-4 | w/ baseball | |
| Wed., 4/23 | V Girls Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | L 3-15 | 2:15pm | |
| Wed., 4/23 | JV Girls Lacrosse | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 5:30 p.m. | ||
| Wed., 4/23 | V Softball | Crosby | Home - HCHS [Directions] | W 14-0 | ||
| Wed., 4/23 | JV Softball | Crosby | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Thu., 4/24 | V Boys Outdoor Track | Sacred Heart | Home - HCHS [Directions] | HC 96 SH 52 | ||
| Thu., 4/24 | V Girls Outdoor Track | Sacred Heart | Home - HCHS [Directions] | HC 91 SH 52 | ||
| Fri., 4/25 | V Baseball | Kennedy | Away - Waterville Park [Directions] | L 10-11 | 2:30pm | |
| Fri., 4/25 | FR Baseball | Kennedy | Away - Bucks Hill Park [Directions] | 3:30 p.m. | ||
| Fri., 4/25 | V Boys Tennis | Kennedy | Away - Chase Park [Directions] | W 6-3 | ||
| Fri., 4/25 | V Softball | Kennedy | Home - HCHS [Directions] | W 11-0 | ||
| Fri., 4/25 | JV Softball | Kennedy | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 4/25 | V Girls Tennis | Kennedy | Home - HCHS [Directions] | W 4-3 | ||
| Sat., 4/26 | V Boys Lacrosse | Wamogo | Away - Wamogo MS Soccer Field (Lower Field) [Directions] | W 14-5 | 11:15am | |
| Sat., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | 8:00am | |
| Sat., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | ||
| Mon., 4/28 | V Baseball | Watertown | Home - HCHS [Directions] | L 6-0 | ||
| Mon., 4/28 | FR Baseball | Watertown | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Mon., 4/28 | V Boys Tennis | Watertown | Home - HCHS [Directions] | W 7-2 | ||
| Mon., 4/28 | V Boys Tennis | Watertown | Away - Holy Cross HS [Directions] | W 8-0 | ||
| Mon., 4/28 | V Girls Lacrosse | Capital Prep | Home - Holy Cross HS [Directions] | W 17-0 | ||
| Mon., 4/28 | V Softball | Watertown | Away - Watertown High School [Directions] | W 8-6 | 2:30pm | |
| Mon., 4/28 | JV Softball | Watertown | Away - Veteran's Park #1 [Directions] | 3:45 p.m. | ||
| Mon., 4/28 | V Girls Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | W 4-3 | w/ softball | |
| Tue., 4/29 | V Baseball | Naugatuck | Home - HCHS [Directions] | W 2-0 | ||
| Tue., 4/29 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:30 p.m. | ||
| Tue., 4/29 | V Boys Golf | St. Paul Catholic | Away - Chippanee Golf Club [Directions] | Holy Cross-167 St Paul-179 | ||
| Tue., 4/29 | V Boys Lacrosse | Amistad | Away - Clinton Avenue School [Directions] | W 15-8 | 2:45pm | |
| Tue., 4/29 | V Boys Outdoor Track | Wilby, Torrington | Home - HCHS [Directions] | HC 116 Wilby 34 HC 93 Torrington 57 | ||
| Tue., 4/29 | V Girls Lacrosse | Amistad | Home - Post University [Directions] | W 16-4 | ||
| Tue., 4/29 | V Girls Outdoor Track | Wilby, Torrington | Home - HCHS [Directions] | HC 74 Torrington 76 HC 109 Wilby 32 | ||
| Tue., 4/29 | V Girls Tennis | Woodland | Home - HCHS [Directions] | L 1-5 | ||
| Thu., 5/1 | V Boys Golf | Woodland Hawk Inv | Away - Oxford Greens | Cancelled | ||
| Thu., 5/1 | V Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | L 9-11 | 3:30pm | |
| Thu., 5/1 | JV Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 4:30 p.m. | ||
| Thu., 5/1 | V Boys Tennis | Wilby | Home - HCHS [Directions] | W 6-3 | ||
| Fri., 5/2 | FR Baseball | Naugatuck | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Fri., 5/2 | JV Boys Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 3:45 p.m. | ||
| Fri., 5/2 | V Boys Tennis | Naugatuck | Home - HCHS [Directions] | L 0-9 | ||
| Fri., 5/2 | V Girls Tennis | Naugatuck | Away - Naugatuck High School [Directions] | L 4-3 | w/ jv softball | |
| Sat., 5/3 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Sacred Heart University [Directions] | L 10-14 | 1:30pm | |
| Sat., 5/3 | V Softball | Seymour | Home - HCHS [Directions] | L 0-8 | ||
| Sat., 5/3 | FR Softball | Naugatuck | Home - Lower Murray Park [Directions] | 11:00 a.m. | ||
| Mon., 5/5 | V Baseball | Sacred Heart | Away - Fulton Park | L 4-3 | 2:30pm | |
| Mon., 5/5 | V Boys Golf | Sacred Heart, Waterbury Coop | Home - Western Hills [Directions] | HC 178 SHHS 199 Kennedy 261 | ||
| Mon., 5/5 | V Boys Lacrosse | St. Paul Catholic | Home - Post University [Directions] | L 7-4 | ||
| Mon., 5/5 | V Boys Tennis | Sacred Heart | Away - Fulton Park | L 4-5 | w/ baseball | |
| Mon., 5/5 | V Girls Lacrosse | Capital Prep | Away - Colt Park [Directions] | W 16-3 | 2:15pm | |
| Mon., 5/5 | V Softball | Sacred Heart | Home - HCHS [Directions] | W 3-0 | ||
| Mon., 5/5 | V Girls Tennis | Sacred Heart | Home - HCHS [Directions] | W 7-0 | ||
| Tue., 5/6 | JV Baseball | Sacred Heart | Away - Fulton Park | 3:30 p.m. | 2:30pm | |
| Tue., 5/6 | V Boys Golf | Naugatuck, Crosby | Away - Hop Brook [Directions] | Holy Cross-187 Naugatuck-201 | ||
| Tue., 5/6 | V Boys Outdoor Track | Seymour, Naugatuck, Wolcott | Away - Naugatuck High School [Directions] | HC 99 Naugatuck 51 HC 83 Seymour 67 HC 99 Wolcott 51 | 2:15pm | |
| Tue., 5/6 | V Girls Outdoor Track | Seymour, Naugatuck, Wolcott | Away - Naugatuck High School [Directions] | HC 71 Naugy 79 HC 61 Seymour 89 HC 83 Wolcott 66 | 2:15pm | |
| Tue., 5/6 | JV Softball | Sacred Heart | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Wed., 5/7 | V Baseball | St. Paul Catholic | Home - HCHS [Directions] | W 10-9 | ||
| Wed., 5/7 | FR Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | ||
| Wed., 5/7 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | W 9-0 | ||
| Wed., 5/7 | V Girls Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | L 6-17 | 2:15pm | |
| Wed., 5/7 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 6-13 | 2:15pm | |
| Wed., 5/7 | V Girls Tennis | St. Paul Catholic | Away - Peck Park, Bristol [Directions] | L 5-2 | w/ softball | |
| Thu., 5/8 | V Boys Lacrosse | Immaculate | Home - Post University [Directions] | L 5-18 | ||
| Thu., 5/8 | JV Boys Lacrosse | Immaculate | Home - HCHS [Directions] | 5:15 p.m. | ||
| Thu., 5/8 | JV Girls Lacrosse | Wolcott | Away - Wolcott Sports Complex | 6:00 p.m. | 4:45pm | |
| Sat., 5/10 | V Boys Lacrosse | Housatonic Regional | Away - Hotchkiss [Directions] | L 8-9(OT) | 11:00am | |
| Sat., 5/10 | V Boys Outdoor Track | Spartan Invitational | Away - Shepaug HS | 10:00 a.m. | 8:30am | |
| Sat., 5/10 | V Girls Lacrosse | Housatonic Regional | Home - Holy Cross HS [Directions] | L 7-17 | ||
| Sat., 5/10 | V Girls Outdoor Track | Spartan Invitational | Away - Shepaug HS | 10:00 a.m. | 8:30am | |
| Sat., 5/10 | FR Softball | Woodland | Away - Woodland Softball Field [Directions] | 11:00 a.m. | no bus | |
| Mon., 5/12 | V Baseball | Wilby | Home - Holy Cross HS [Directions] | W 14-7 | 2:30m | |
| Mon., 5/12 | V Boys Golf | Wolcott | Home - Western Hills [Directions] | HC 180 Wolcott 187 Wilby 268 | ||
| Mon., 5/12 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 7-14 | 2:30pm | |
| Mon., 5/12 | V Softball | Wilby | Home - HCHS [Directions] | W 20-0 | ||
| Mon., 5/12 | V Girls Tennis | Wilby | Home - HCHS [Directions] | W 7-0 | ||
| Mon., 5/12 | V Girls Tennis | Wilby | Home - Holy Cross HS [Directions] | W 7-0 | ||
| Tue., 5/13 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | W 7-1 | 2:15pm | |
| Tue., 5/13 | JV Baseball | Wilby | Home - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/13 | V Boys Golf | Woodland | Away - Western Hills [Directions] | Holy Cross-176 Woodland-182 | ||
| Tue., 5/13 | V Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | L 5-17 | 2:15pm | |
| Tue., 5/13 | JV Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | 5:30 p.m. | ||
| Tue., 5/13 | V Boys Outdoor Track | Woodland, St. Paul Catholic, Derby | Away - Woodland High School Track [Directions] | Woodland 79 HC 71 HC 130 SP 15 HC 90 Derby 60 | 2:00pm | |
| Tue., 5/13 | V Boys Tennis | Torrington | Away - Torrington High School [Directions] | L 4-5 | ||
| Tue., 5/13 | V Girls Lacrosse | Lewis Mills | Home - Post University [Directions] | L 7-19 | ||
| Tue., 5/13 | JV Girls Lacrosse | Lewis Mills | Home - Holy Cross HS [Directions] | Cancelled | ||
| Tue., 5/13 | V Girls Outdoor Track | Woodland, St. Paul Catholic, Derby | Away - Woodland High School Track [Directions] | Woodland 94 HC 56 HC 98 SP 47 HC 119 Derby 26 | 2:00pm | |
| Tue., 5/13 | V Softball | Naugatuck | Away - Breen Field [Directions] | L 0-1 | 2:00pm | |
| Tue., 5/13 | JV Softball | Naugatuck | Away - Breen Field [Directions] | 4:00 p.m. | ||
| Tue., 5/13 | V Girls Tennis | Torrington | Home - HCHS [Directions] | W 4-3 | ||
| Wed., 5/14 | V Baseball | Crosby | Home - HCHS [Directions] | W 12-5 | ||
| Wed., 5/14 | V Boys Tennis | Crosby | Home - HCHS [Directions] | L 2-7 | ||
| Wed., 5/14 | V Softball | Crosby | Away - Crosby HS Field #1 [Directions] | W 16-0(6) | 2:30pm | |
| Wed., 5/14 | JV Softball | Crosby | Away - Crosby HS Field #2 [Directions] | 3:30 p.m. | ||
| Wed., 5/14 | V Girls Tennis | Crosby | Away - Crosby HS [Directions] | W 7-0 | w/ softball | |
| Thu., 5/15 | V Baseball | Kennedy | Home - HCHS [Directions] | W 10-6 | ||
| Thu., 5/15 | FR Baseball | Kennedy | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Thu., 5/15 | V Boys Golf | Watertown | Home - Western Hills [Directions] | Holy Cross-176 Watertown-174 | ||
| Thu., 5/15 | V Boys Lacrosse | Wamogo | Home - Post University [Directions] | W 14-5 | ||
| Thu., 5/15 | V Softball | Torrington | Home - HCHS [Directions] | L 5-0 | ||
| Thu., 5/15 | JV Softball | Torrington | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Thu., 5/15 | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | L 4-3 | w/ softball | |
| Fri., 5/16 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Post University [Directions] | W 16-11 | ||
| Sat., 5/17 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | L 6-16 | 11:15am | |
| Sat., 5/17 | V Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | L 6-22 | 9:15am | |
| Sat., 5/17 | V Softball | Kennedy | Away - Municipal Stadium [Directions] | W 8-3 | ||
| Mon., 5/19 | V Baseball | Seymour | Away - French Park [Directions] | W 6-0 | 2:15pm | |
| Mon., 5/19 | FR Baseball | Seymour | Away - Seymour High School [Directions] | 3:45 p.m. | ||
| Mon., 5/19 | V Boys Golf | Torrington | Home - Western Hills [Directions] | Holy Cross-179 Torrington-191 | ||
| Mon., 5/19 | V Boys Lacrosse | Amistad | Home - Post University [Directions] | W 18-1 | ||
| Mon., 5/19 | V Boys Tennis | Woodland | Away - Woodland High School Tennis courts [Directions] | W 6-3 | 2:30pm | |
| Mon., 5/19 | V Girls Lacrosse | Amistad | Away - Clinton Avenue School [Directions] | W 15-8 | 2:15pm | |
| Mon., 5/19 | FR Softball | New Milford | Away - New Milford High School [Directions] | 3:45 p.m. | 2:15pm | |
| Mon., 5/19 | V Girls Tennis | Ansonia | Home - Holy Cross HS [Directions] | W 7-0 | ||
| Tue., 5/20 | V Baseball | Naugatuck | Away - Rotary Field [Directions] | L 3-4 | 2:15pm | |
| Tue., 5/20 | FR Baseball | Naugatuck | Home - Upper Murray Park [Directions] | 3:30 p.m. | ||
| Tue., 5/20 | V Boys Golf | St. Paul Catholic, Wilby | Home - Western Hills [Directions] | Holy Cross-174 St Paul-182 Wilby-266 | ||
| Tue., 5/20 | V Boys Lacrosse | Watertown | Home - Post University [Directions] | L 11-13 | ||
| Tue., 5/20 | V Boys Outdoor Track | City Invitational | Home - HCHS [Directions] | 3:30 p.m. | ||
| Tue., 5/20 | V Girls Outdoor Track | City Invitational | Home - HCHS [Directions] | 3:30 p.m. | ||
| Tue., 5/20 | V Softball | Naugatuck | Home - HCHS [Directions] | W 3-2(8) | ||
| Tue., 5/20 | JV Softball | Naugatuck | Home - Lower Murray Park [Directions] | 3:30 p.m. | ||
| Tue., 5/20 | V Girls Tennis | Seymour | Home - HCHS [Directions] | W 4-3 | ||
| Wed., 5/21 | V Baseball | Sacred Heart | Home - HCHS [Directions] | W 7-3 | ||
| Wed., 5/21 | JV Baseball | Naugatuck | Away - Rotary Field [Directions] | 3:30 p.m. | 2:15pm | |
| Wed., 5/21 | FR Baseball | Sacred Heart | Home - Upper Murray Park [Directions] | Cancelled | ||
| Wed., 5/21 | V Boys Tennis | Kennedy | Home - HCHS [Directions] | W 8-1 | ||
| Wed., 5/21 | V Girls Lacrosse | Watertown | Home - Post University [Directions] | L 8-14 | ||
| Wed., 5/21 | V Softball | Sacred Heart | Away - Municipal Stadium | W 13-2 | 2:30pm | |
| Fri., 5/23 | JV Baseball | Sacred Heart | Home - HCHS [Directions] | 3:30 p.m. | ||
| Fri., 5/23 | V Boys Tennis | Naugatuck | Away - Naugatuck High School [Directions] | L 3-6 | ||
| Fri., 5/23 | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | 3:30 p.m. | 2:15pm | |
| Sat., 5/24 | V Boys Tennis | Wolcott | Away - Wolcott High School [Directions] | L 0-9 | 2:30pm | |
| Sat., 5/24 | V Softball | Naugatuck | Home - Holy Cross HS [Directions] | 12:00 p.m. | ||
| Tue., 5/27 | V Girls Lacrosse | Housatonic Regional | Away - Hotchkiss [Directions] | 3:30 p.m. | 1:45pm | |
| Wed., 5/28 | V Boys Golf | Sacred Heart, Crosby | Away - East Mountain | Holy Cross-179 | ||
| Wed., 5/28 | V Boys Golf | Sacred Heart | Away - WCC | Holy Cross-170 | ||
| Wed., 5/28 | V Boys Outdoor Track | NVL Invitational | Away - TBA | 1:30 p.m. | 12:00pm | |
| Wed., 5/28 | V Girls Outdoor Track | NVL Invitational | Away - TBA | 1:30 p.m. | ||
| Thu., 5/29 | V Boys Golf | Torrington, Wilby | Home - Western Hills [Directions] | Holy Cross-178 Torrington-198 | ||
| Thu., 5/29 | V Boys Outdoor Track | NVL JV Invitational | Away - TBA | 3:30 p.m. | 2:15pm | |
| Thu., 5/29 | V Girls Outdoor Track | NVL JV Invitational | Away - TBA | 3:30 p.m. | ||
| Mon., 6/2 | V Boys Golf | Notre Dame-West Haven | Home - WCC [Directions] | Cancelled | ||
| Tue., 6/3 | V Boys Golf | Naugatuck, Waterbury Coop | Home - Western Hills [Directions] | 164 | ||
| Thu., 6/5 | V Boys Golf | NVL Championships | Away - Watertown Golf Club | TBA | ||