| Crosby 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 389 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Wolcott | Away - Wolcott High School [Directions] | 3:30 p.m. | 2:15pm | |
| TBA | JV Baseball | Sacred Heart | Away - Fulton Park | TBA | ||
| TBA | JV Baseball | Watertown | Away - Veterans Park [Directions] | TBA | 9:30am | |
| TBA | JV Baseball | Holy Cross | Home - Crosby HS [Directions] | TBA | ||
| TBA | JV Baseball | Wilby | Away - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Seymour | Home - Crosby HS [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | 2:15pm | |
| TBA | JV Baseball | Derby | Home - Crosby HS [Directions] | TBA | ||
| TBA | JV Baseball | Sacred Heart | Home - Washington Park [Directions] | TBA | ||
| TBA | JV Baseball | Holy Cross | Away - HCHS [Directions] | TBA | 2:15pm | |
| TBA | JV Baseball | Wilby | Home - Crosby HS [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Home - Crosby HS [Directions] | TBA | ||
| TBA | JV Baseball | Naugatuck | Home - Crosby HS [Directions] | TBA | ||
| TBA | FR Baseball | Ansonia | Home - Crosby HS [Directions] | TBA | ||
| TBA | FR Baseball | Wilby | Away - Wilby H.S. [Directions] | TBA | 2:15pm | |
| TBA | FR Baseball | Sacred Heart | Home - Crosby HS [Directions] | TBA | ||
| TBA | FR Baseball | Wilby | Home - Crosby HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | TBA | 5:30pm | |
| TBA | FR Boys Basketball | Holy Cross | Home - Crosby HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | TBA | ||
| TBA | FR Boys Basketball | Sacred Heart | Home - Crosby HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Wilby | Home - Crosby HS [Directions] | TBA | ||
| TBA | JV Football | Naugatuck | Away - Naugatuck High School [Directions] | TBA | ||
| TBA | JV Boys Soccer | Wolcott | Away - Wolcott High School, Lower Soccer Field [Directions] | TBA | 9:30am | |
| TBA | JV Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | TBA | 4:15pm | |
| TBA | FR Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | TBA | ||
| TBA | JV Softball | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | 2:15pm | |
| TBA | JV Softball | Sacred Heart | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Torrington | Away - Torrington High School [Directions] | TBA | 2:15pm | |
| TBA | JV Softball | Watertown | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Wilby | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Wilby | Away - Bucks Hill Park [Directions] | TBA | 2:15pm | |
| Tue., 9/10 | V Boys Soccer | Woodland | Home - Crosby HS [Directions] | T 2-2 | ||
| Tue., 9/10 | V Girls Volleyball | Holy Cross | Home - Crosby HS [Directions] | L 0-3 | game starts 22 min after JV | |
| Tue., 9/10 | JV Girls Volleyball | Holy Cross | Home - Crosby HS [Directions] | 4:30 p.m. | ||
| Wed., 9/11 | JV Boys Soccer | Woodland | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Thu., 9/12 | V Boys Soccer | Sacred Heart | Away - Bucks Hill Park | W 4-3 | 2:15pm | |
| Thu., 9/12 | V Girls Volleyball | Kennedy | Home - Crosby HS [Directions] | L 0-3 | game starts 22 min after JV | |
| Thu., 9/12 | JV Girls Volleyball | Kennedy | Home - Crosby HS [Directions] | 4:30 p.m. | ||
| Fri., 9/13 | V Football | Naugatuck | Home - Crosby HS [Directions] | L 8-39 | ||
| Fri., 9/13 | JV Boys Soccer | Sacred Heart | Away - Bucks Hill Park | 3:45 p.m. | 2:15pm | |
| Sat., 9/14 | FR Football | Naugatuck | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Tue., 9/17 | V Boys Cross Country | Holy Cross, Naugatuck, Torrington | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 9/17 | V Girls Cross Country | Holy Cross, Naugatuck, Torrington | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 9/17 | V Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | W 3-0 | 2:15pm | game starts 22 min after JV |
| Tue., 9/17 | JV Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:15pm | |
| Wed., 9/18 | FR Football | Woodland | Home - Crosby HS [Directions] | Cancelled | ||
| Wed., 9/18 | V Boys Soccer | Naugatuck | Away - Naugatuck High School [Directions] | L 6-0 | 4:30pm | |
| Wed., 9/18 | V Girls Volleyball | Ansonia | Home - Crosby HS [Directions] | L 3-2 | game starts 22 min after JV | |
| Wed., 9/18 | JV Girls Volleyball | Ansonia | Home - Crosby HS [Directions] | 4:45 p.m. | ||
| Thu., 9/19 | JV Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:30 p.m. | 2:15pm | |
| Fri., 9/20 | V Football | Woodland | Away - Woodland Football Field [Directions] | L 6-40 | 5:00pm (2) | cheer bus 5:30pm |
| Fri., 9/20 | V Boys Soccer | Kennedy | Away - West Side Middle School [Directions] | L 3-2 | 4:30pm | |
| Sat., 9/21 | JV Football | Woodland | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Sat., 9/21 | JV Boys Soccer | Kennedy | Away - West Side Middle School [Directions] | 10:00 a.m. | 8:30am | |
| Mon., 9/23 | V Boys Soccer | Derby | Home - Crosby HS [Directions] | W 1-0 | ||
| Tue., 9/24 | V Boys Cross Country | Kennedy, Naugatuck, Wilby, Sacred Heart | Away - Bucks Hill Park [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 9/24 | V Girls Cross Country | Kennedy, Naugatuck, Wilby, Sacred Heart | Away - Bucks Hill Park [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 9/24 | V Girls Volleyball | Naugatuck | Home - Crosby HS [Directions] | L 3-0 | game starts 22 min after JV | |
| Tue., 9/24 | JV Girls Volleyball | Naugatuck | Home - Crosby HS [Directions] | 4:30 p.m. | ||
| Wed., 9/25 | FR Football | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 3:45 p.m. | 2:15pm | |
| Wed., 9/25 | V Boys Soccer | Holy Cross | Home - Crosby HS [Directions] | L 3-0 | ||
| Wed., 9/25 | V Girls Volleyball | Seymour | Away - Seymour High School [Directions] | L 3-0 | 2:15pm | game starts 22 min after JV |
| Wed., 9/25 | JV Girls Volleyball | Seymour | Away - Seymour High School [Directions] | 4:45 p.m. | 2:15pm | |
| Thu., 9/26 | JV Boys Soccer | Holy Cross | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Fri., 9/27 | V Football | Watertown | Home - Crosby HS [Directions] | L 30-36 | ||
| Fri., 9/27 | V Boys Soccer | Seymour | Away - Seymour High Main Field [Directions] | L 4-1 | 4:30pm | |
| Fri., 9/27 | V Girls Volleyball | St. Paul Catholic | Home - Crosby HS [Directions] | W 3-1 | game starts 22 min after JV | |
| Fri., 9/27 | JV Girls Volleyball | St. Paul Catholic | Home - Crosby HS [Directions] | 4:30 p.m. | ||
| Sat., 9/28 | JV Football | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 10:00 a.m. | 8:30am | |
| Sat., 9/28 | JV Boys Soccer | Seymour | Away - Bungay School [Directions] | 10:00 a.m. | 8:30am | |
| Tue., 10/1 | V Boys Cross Country | Seymour, Naugatuck, Woodland | Away - Seymour High Lower Field [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 10/1 | V Boys Soccer | Ansonia | Home - Crosby HS [Directions] | T 3-3 | ||
| Tue., 10/1 | V Girls Cross Country | Seymour, Naugatuck, Woodland | Away - Seymour High Lower Field [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 10/1 | V Girls Volleyball | Woodland | Away - Woodland High School Gym [Directions] | L 0-3 | 2:15pm | game starts 22 min after JV |
| Tue., 10/1 | JV Girls Volleyball | Woodland | Away - Woodland High School Gym [Directions] | 4:45 p.m. | 2:15pm | |
| Wed., 10/2 | JV Boys Soccer | Ansonia | Home - Crosby HS [Directions] | Cancelled | ||
| Thu., 10/3 | V Girls Volleyball | Torrington | Away - Torrington High School [Directions] | L 0-3 | 2:15pm | game starts 22 min after JV |
| Thu., 10/3 | JV Girls Volleyball | Torrington | Away - Torrington High School [Directions] | 4:45 p.m. | 2:15pm | |
| Fri., 10/4 | V Football | Derby | Home - Crosby HS [Directions] | L 7-34 | ||
| Fri., 10/4 | V Boys Soccer | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | L 2-0 | 4:30pm | |
| Fri., 10/4 | V Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | L 1-3 | 2:15pm | game starts 22 min after JV |
| Fri., 10/4 | JV Girls Volleyball | Ansonia | Away - Ansonia High School [Directions] | 4:45 p.m. | 2:15pm | |
| Sat., 10/5 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | TBA | TBA | |
| Sat., 10/5 | JV Football | Derby | Away - Ryan Athletic Complex-Deflippo Field [Directions] | 10:00 a.m. | 8:30am | |
| Sat., 10/5 | JV Boys Soccer | Derby | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Sat., 10/5 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | TBA | TBA | |
| Mon., 10/7 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 3-0 | 2:15pm | |
| Tue., 10/8 | V Boys Cross Country | Watertown, Naugatuck, Wolcott, St. Paul Catholic | Away - Veterans Park [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 10/8 | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 10/8 | V Girls Cross Country | Watertown, Naugatuck, Wolcott, St. Paul Catholic | Away - Veterans Park [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 10/8 | V Girls Volleyball | Watertown | Home - Crosby HS [Directions] | W 3-2 | game starts 22 min after JV | |
| Tue., 10/8 | JV Girls Volleyball | Watertown | Home - Crosby HS [Directions] | 4:30 p.m. | ||
| Wed., 10/9 | FR Football | Wolcott | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Wed., 10/9 | V Boys Soccer | Wilby | Away - Municipal Stadium [Directions] | L 4-0 | 5:30pm | |
| Wed., 10/9 | V Girls Volleyball | Wolcott | Home - Crosby HS [Directions] | L 0-3 | game starts 22 min after JV | |
| Wed., 10/9 | JV Girls Volleyball | Wolcott | Home - Crosby HS [Directions] | 4:30 p.m. | ||
| Thu., 10/10 | JV Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | 2:15pm | |
| Thu., 10/10 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | L 0-3 | 2:15pm | game starts 22 min after JV |
| Thu., 10/10 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 4:45 p.m. | 2:15pm | |
| Fri., 10/11 | V Football | Wolcott | Away - Wolcott High School, Monroe Field [Directions] | L 0-45 | 5:30pm (2) | |
| Fri., 10/11 | V Boys Soccer | Watertown | Home - Crosby HS [Directions] | T 2-2 | ||
| Sat., 10/12 | JV Football | Wolcott | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Sat., 10/12 | JV Boys Soccer | Watertown | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Tue., 10/15 | V Boys Cross Country | NVL Championships | Away - Veterans' Park | 3:30 p.m. | 2:15pm | |
| Tue., 10/15 | V Boys Soccer | Torrington | Away - Torrington High School [Directions] | L 7-0 | 5:00pm | |
| Tue., 10/15 | V Girls Cross Country | NVL Championships | Away - Veterans' Park | 3:30 p.m. | 2:15pm | |
| Wed., 10/16 | JV Boys Soccer | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | 2:15pm | |
| Wed., 10/16 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 2-3 | 2:15pm | game starts 22 min after JV |
| Wed., 10/16 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | 2:15pm | |
| Fri., 10/18 | V Boys Cross Country | NVL Novice Race | Away - Woodland HS | 3:30 p.m. | 2:15pm | |
| Fri., 10/18 | V Football | Immaculate | Home - Crosby HS [Directions] | W 43-20 | ||
| Fri., 10/18 | V Boys Soccer | Wilby | Home - Crosby HS [Directions] | L 6-1 | ||
| Fri., 10/18 | V Girls Cross Country | NVL Novice Race | Away - Woodland HS | 3:30 p.m. | 2:15pm | |
| Fri., 10/18 | V Girls Volleyball | Wilby | Home - Crosby HS [Directions] | W 3-0 | game starts 22 min after JV | |
| Fri., 10/18 | JV Girls Volleyball | Wilby | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Sat., 10/19 | JV Boys Soccer | Wilby | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Mon., 10/21 | JV Football | Immaculate | Home - Crosby [Directions] | 4:00 p.m. | 8:30am | |
| Mon., 10/21 | V Boys Soccer | Sacred Heart | Home - Crosby HS [Directions] | L 3-2 | ||
| Mon., 10/21 | V Girls Volleyball | Torrington | Home - Crosby HS [Directions] | L 0-3 | game starts 22 min after JV | |
| Mon., 10/21 | JV Girls Volleyball | Torrington | Home - Crosby HS [Directions] | 4:30 p.m. | ||
| Tue., 10/22 | JV Boys Soccer | Sacred Heart | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Wed., 10/23 | FR Football | Wilby | Away - Wilby H.S. [Directions] | 2:30 p.m. | 2:15pm | |
| Wed., 10/23 | V Boys Soccer | Kaynor Tech | Away - Kaynor Tech Soccer Field [Directions] | L 2-1 | 2:15pm | |
| Wed., 10/23 | V Girls Volleyball | Naugatuck | Away - Naugatuck High School [Directions] | L 1-3 | 2:15pm | game starts 22 min after JV |
| Wed., 10/23 | JV Girls Volleyball | Naugatuck | Away - Naugatuck High School [Directions] | 4:45 p.m. | 2:15pm | |
| Thu., 10/24 | V Girls Volleyball | Kaynor Tech | Home - Crosby HS [Directions] | W 3-0 | ||
| Thu., 10/24 | JV Girls Volleyball | Kaynor Tech | Home - Crosby HS [Directions] | 3:45 p.m. | ||
| Fri., 10/25 | V Football | Wilby | Home - Crosby HS [Directions] | L 22-32 | ||
| Sat., 10/26 | V Boys Cross Country | CIAC Class Meet | Away - Wickham Park | TBA | TBA | |
| Sat., 10/26 | JV Football | Wilby | Away - Wilby H.S. [Directions] | 10:00 a.m. | 8:30am | |
| Sat., 10/26 | V Girls Cross Country | CIAC Class Meet | Away - Wickham Park | TBA | TBA | |
| Mon., 10/28 | V Girls Volleyball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | W 3-0 | 3:45pm | |
| Mon., 10/28 | JV Girls Volleyball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 3:45 p.m. | 2:15pm | |
| Wed., 10/30 | FR Football | Seymour | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Fri., 11/1 | V Boys Cross Country | CIAC State Open | Away | TBA | TBA | |
| Fri., 11/1 | V Football | Seymour | Away - Seymour High Main Field [Directions] | L 26-62 | 5:30pm (2) | cheer bus 5:45pm |
| Fri., 11/1 | V Girls Cross Country | CIAC State Open | Away | TBA | TBA | |
| Sat., 11/2 | JV Football | Seymour | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Thu., 11/7 | FR Football | St. Paul Catholic | Home - Crosby HS [Directions] | 5:00 p.m. | 2:15pm | |
| Fri., 11/8 | V Football | St. Paul Catholic | Home - Crosby HS [Directions] | L 24-52 | ||
| Wed., 11/13 | FR Football | Ansonia | Home - Crosby HS [Directions] | 5:00 p.m. | ||
| Thu., 11/14 | V Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | L 8-50 | 5:30pm (2) | cheer bus 5:45pm |
| Sat., 11/16 | JV Football | Ansonia | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Wed., 11/20 | FR Football | Kennedy | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Fri., 11/22 | JV Football | Kennedy | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Thu., 11/28 | V Football | Kennedy | Away - Municipal Stadium [Directions] | L 28-30 | 8:30am (2) | |
| Fri., 12/13 | V Boys Swimming and Diving | NVL Indicational | Away - Kennedy HS | 4:00 p.m. | 2:15pm | |
| Fri., 12/13 | V Girls Basketball | Naugatuck | Home - Crosby HS [Directions] | W 56-38 | ||
| Fri., 12/13 | JV Girls Basketball | Naugatuck | Home - Crosby HS [Directions] | W 38-27 | ||
| Wed., 12/18 | V Boys Basketball | Ansonia | Home - Crosby HS [Directions] | W 99-41 | ||
| Wed., 12/18 | JV Boys Basketball | Ansonia | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Wed., 12/18 | V Girls Basketball | Ansonia | Away - Ansonia High School [Directions] | W 63-10 | 4:00pm | |
| Wed., 12/18 | JV Girls Basketball | Ansonia | Away - Ansonia High School [Directions] | W 42-14 | 4:00pm | |
| Thu., 12/19 | FR Boys Basketball | Woodland | Away - Woodland High School Gym [Directions] | 7:00 p.m. | 5:30pm | |
| Fri., 12/20 | V Boys Basketball | Woodland | Away - Woodland High School Gym [Directions] | W 97-42 | 4:00pm | |
| Fri., 12/20 | JV Boys Basketball | Woodland | Away - Woodland High School Gym [Directions] | 5:15 p.m. | 4:00pm | |
| Fri., 12/20 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | 4:00 p.m. | 2:15pm | |
| Fri., 12/20 | V Girls Basketball | Woodland | Home - Crosby HS [Directions] | W 61-43 | ||
| Fri., 12/20 | JV Girls Basketball | Woodland | Home - Crosby HS [Directions] | W 55-36 | ||
| Mon., 12/23 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | W 79-76 | ||
| Mon., 12/23 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Mon., 12/23 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 12:00 p.m. | ||
| Mon., 12/23 | V Girls Basketball | Sacred Heart | Home - Crosby HS [Directions] | L 30-38 | ||
| Mon., 12/23 | JV Girls Basketball | Sacred Heart | Home - Crosby HS [Directions] | L 18-33 | ||
| Fri., 12/27 | V Boys Basketball | Torrington | Home - Crosby HS [Directions] | W 93-59 | ||
| Fri., 12/27 | JV Boys Basketball | Torrington | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 12/27 | FR Boys Basketball | Torrington | Home - Crosby HS [Directions] | 11:00 a.m. | ||
| Fri., 12/27 | V Girls Basketball | Torrington | Away - Torrington High School [Directions] | L 39-51 | 4:00pm | |
| Fri., 12/27 | JV Girls Basketball | Torrington | Away - Torrington High School [Directions] | L 27-54 | 4:00pm | |
| Tue., 1/7 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 80-55 | 4:00pm | |
| Tue., 1/7 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | 4:00pm | |
| Tue., 1/7 | V Girls Basketball | St. Paul Catholic | Home - Crosby HS [Directions] | L 25-55 | ||
| Tue., 1/7 | JV Girls Basketball | St. Paul Catholic | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Wed., 1/8 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | 6:00pm | |
| Fri., 1/10 | V Boys Basketball | Holy Cross | Home - Crosby HS [Directions] | W 84-58 | ||
| Fri., 1/10 | JV Boys Basketball | Holy Cross | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | L 35-71 | 4:15pm | |
| Fri., 1/10 | JV Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | 4:15pm | |
| Sat., 1/11 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 1:00 p.m. | 11:30am | |
| Mon., 1/13 | FR Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 1/14 | V Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | W 99-69 | ||
| Tue., 1/14 | JV Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | V Boys Swimming and Diving | Woodland | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | V Girls Basketball | Wilby | Home - Crosby HS [Directions] | W 60-15 | ||
| Tue., 1/14 | JV Girls Basketball | Wilby | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | W 77-49 | 4:00pm | |
| Wed., 1/15 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown High School [Directions] | 5:15 p.m. | 4:00pm | |
| Wed., 1/15 | FR Boys Basketball | Notre Dame-West Haven | Home - Crosby HS [Directions] | 3:30 p.m. | ||
| Wed., 1/15 | V Girls Basketball | Watertown | Home - Crosby HS [Directions] | L 27-32 | ||
| Wed., 1/15 | JV Girls Basketball | Watertown | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Thu., 1/16 | FR Boys Basketball | Seymour | Home - Crosby HS [Directions] | 7:00 p.m. | ||
| Thu., 1/16 | V Boys Swimming and Diving | Sacred Heart | Home - Crosby HS [Directions] | 7:00 p.m. | ||
| Fri., 1/17 | V Boys Basketball | Seymour | Home - Crosby HS [Directions] | W 96-31 | ||
| Fri., 1/17 | JV Boys Basketball | Seymour | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 1/17 | V Girls Basketball | Seymour | Away - Seymour High School [Directions] | W 46-33 | 4:00pm | |
| Fri., 1/17 | JV Girls Basketball | Seymour | Away - Seymour High School [Directions] | 5:15 p.m. | 4:00pm | |
| Wed., 1/22 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | W 82-43 | ||
| Wed., 1/22 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | ||
| Wed., 1/22 | V Girls Basketball | Kennedy | Home - Crosby HS [Directions] | L 43-48 | ||
| Wed., 1/22 | JV Girls Basketball | Kennedy | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 1/24 | V Boys Basketball | Derby | Home - Crosby HS [Directions] | W 90-47 | ||
| Fri., 1/24 | JV Boys Basketball | Derby | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 1/24 | V Boys Swimming and Diving | Seymour | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | V Girls Basketball | Derby | Away - Derby High- A. Vitello Gymnasium [Directions] | W 65-51 | 4:00pm | |
| Fri., 1/24 | JV Girls Basketball | Derby | Away - Derby High- A. Vitello Gymnasium [Directions] | 7:00 p.m. | 4:00pm | |
| Mon., 1/27 | FR Boys Basketball | Naugatuck | Home - Crosby HS [Directions] | 7:00 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Naugatuck | Home - Crosby HS [Directions] | W 92-63 | ||
| Tue., 1/28 | JV Boys Basketball | Naugatuck | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Tue., 1/28 | V Boys Swimming and Diving | Holy Cross | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | L 29-37 | 4:15pm | |
| Tue., 1/28 | JV Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | 4:15pm | |
| Thu., 1/30 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 3:30 p.m. | 2:15pm | |
| Fri., 1/31 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 97-53 | 4:00pm | |
| Fri., 1/31 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | 5:15 p.m. | 4:00pm | |
| Fri., 1/31 | V Girls Basketball | Wolcott | Home - Crosby HS [Directions] | L 46-50 | ||
| Fri., 1/31 | JV Girls Basketball | Wolcott | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Sat., 2/1 | FR Boys Basketball | Notre Dame-West Haven | Away - Notre Dame High School [Directions] | 10:00 a.m. | 8:30am | |
| Tue., 2/4 | V Boys Basketball | Sacred Heart | Home - Crosby HS [Directions] | L 82-90 | ||
| Tue., 2/4 | JV Boys Basketball | Sacred Heart | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Tue., 2/4 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | L 36-42 | 4:15pm | |
| Tue., 2/4 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:30 p.m. | 4:15pm | |
| Thu., 2/6 | FR Boys Basketball | Torrington | Away - Torrington High School [Directions] | 7:15 p.m. | 5:30pm | |
| Thu., 2/6 | V Girls Basketball | Kaynor Tech | Home - Crosby HS [Directions] | W 57-34 | ||
| Thu., 2/6 | JV Girls Basketball | Kaynor Tech | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Torrington | Away - Torrington High School [Directions] | W 96-75 | 4:00pm | |
| Fri., 2/7 | JV Boys Basketball | Torrington | Away - Torrington High School [Directions] | 5:15 p.m. | 4:00pm | |
| Fri., 2/7 | V Girls Basketball | Torrington | Home - Crosby HS [Directions] | L 41-60 | ||
| Fri., 2/7 | JV Girls Basketball | Torrington | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Mon., 2/10 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 6:30 p.m. | ||
| Tue., 2/11 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | W 80-52 | ||
| Tue., 2/11 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | 2:15pm | |
| Tue., 2/11 | V Girls Basketball | Holy Cross | Home - Crosby HS [Directions] | L 39-46 | ||
| Tue., 2/11 | JV Girls Basketball | Holy Cross | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 2/14 | V Boys Basketball | Wilby | Home - Crosby HS [Directions] | W 87-58 | ||
| Fri., 2/14 | JV Boys Basketball | Wilby | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Mon., 2/17 | FR Boys Basketball | Kennedy | Home - Crosby HS [Directions] | 7:00 p.m. | ||
| Thu., 2/20 | V Boys Basketball | Kennedy | Home - Crosby HS [Directions] | W 92-77 | ||
| Thu., 2/20 | JV Boys Basketball | Kennedy | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Thu., 2/20 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 30-58 | 4:15pm | |
| Thu., 2/20 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | 4:15pm | |
| Fri., 2/21 | V Boys Basketball | Bunnell | Home - Crosby HS [Directions] | W 88-76 | ||
| Fri., 2/21 | JV Boys Basketball | Bunnell | Home - Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 2/21 | V Boys Swimming and Diving | Naugatuck | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Fri., 2/21 | V Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | W 64-37 | 4:15pm | |
| Tue., 2/25 | V Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | W 87-65 | 4:15pm | |
| Tue., 2/25 | JV Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 5:30 p.m. | 4:15pm | |
| Tue., 2/25 | FR Boys Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 3/4 | V Boys Swimming and Diving | NVL Trials | Away - Kennedy HS | 4:00 p.m. | 2:15pm | |
| Wed., 3/5 | V Boys Swimming and Diving | NVL Diving | Away - Kennedy HS | 7:00 p.m. | TBA | |
| Fri., 3/7 | V Boys Swimming and Diving | NVL Finals | Away - Kennedy HS | 6:00 p.m. | TBA | |
| Wed., 4/9 | V Baseball | Ansonia | Home - Washington Park [Directions] | L 8-1 | 2:15pm | |
| Wed., 4/9 | V Softball | Ansonia | Away - Ansonia High School [Directions] | L 0-4 | 2:15pm | |
| Wed., 4/9 | V Girls Tennis | Naugatuck | Away - Naugatuck High School [Directions] | L 0-7 | 2:15pm | |
| Thu., 4/10 | JV Baseball | Ansonia | Home - Washington Park [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | V Girls Tennis | Woodland | Away - Woodland High School Tennis courts [Directions] | L 0-7 | 2:15pm | |
| Fri., 4/11 | V Baseball | Woodland | Away - Woodland High School Baseball Field [Directions] | L 7-1 | 2:15pm | |
| Fri., 4/11 | V Softball | Woodland | Home - Huntington Park [Directions] | L 2-18 | ||
| Fri., 4/11 | JV Softball | Woodland | Home - Huntington Park [Directions] | 3:30 p.m. | ||
| Sat., 4/12 | JV Baseball | Woodland | Away - Woodland High School Baseball Field [Directions] | 10:00 a.m. | 9:30am | |
| Mon., 4/14 | V Baseball | Sacred Heart | Away - Fulton Park | L 7-3 | ||
| Mon., 4/14 | V Softball | Sacred Heart | Home - Crosby HS Field #1 [Directions] | L 5-6(10) | ||
| Mon., 4/14 | V Girls Tennis | Sacred Heart | Home - Fulton Park [Directions] | L 3-4 | ||
| Wed., 4/16 | V Boys Tennis | Torrington | Home - Fulton Park [Directions] | L 6-3 | ||
| Thu., 4/17 | V Baseball | Watertown | Away - Deland Field [Directions] | L 4-2 | 2:15pm | |
| Thu., 4/17 | V Boys Tennis | Watertown | Away - Tennis Courts at Crestbrook Park [Directions] | W 7-2 | 2:15pm | |
| Thu., 4/17 | V Softball | Watertown | Home - Huntingdon Park [Directions] | L 4-20 | ||
| Thu., 4/17 | V Girls Tennis | Watertown | Home - Fulton Park [Directions] | L 2-5 | ||
| Fri., 4/18 | V Softball | Torrington | Away - Torrington High School [Directions] | L 1-16 | 2:15pm | |
| Fri., 4/18 | V Girls Tennis | Torrington | Away - Torrington High School [Directions] | L 1-6 | 8:30am | |
| Sat., 4/19 | V Baseball | Torrington | Home - Washington Park [Directions] | L 7-0 | 2:15pm | |
| Mon., 4/21 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 8-3 | 2:15pm | |
| Mon., 4/21 | V Boys Golf | Watertown, Sacred Heart | Home - East Mountain [Directions] | Crosby 279 Sacred Heart 192 Watertown 175 | 1:50pm | |
| Mon., 4/21 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | W 8-1 | 2:15pm | |
| Mon., 4/21 | V Softball | St. Paul Catholic | Home - Crosby HS Field #1 [Directions] | L 5-13 | ||
| Mon., 4/21 | JV Softball | St. Paul Catholic | Home - Crosby HS Field #2 [Directions] | 3:45 p.m. | ||
| Mon., 4/21 | V Girls Tennis | St. Paul Catholic | Home - Peck Park [Directions] | L 3-4 | ||
| Tue., 4/22 | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:15pm | |
| Tue., 4/22 | V Boys Golf | Naugatuck, Sacred Heart | Away - Hop Brook [Directions] | 3:00 p.m. | 1:45pm | |
| Tue., 4/22 | V Boys Golf | St. Paul Catholic | Away [Directions] | st. paul 180 Crosby 269 | 1:50pm | also w/ Woodland |
| Tue., 4/22 | V Boys Outdoor Track | Holy Cross, Kennedy, Watertown | Away - HCHS [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 4/22 | V Boys Tennis | Woodland | Home - Woodland HS [Directions] | W 7-2 | ||
| Tue., 4/22 | V Girls Outdoor Track | Holy Cross, Kennedy, Watertown | Away - HCHS [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 4/22 | V Girls Tennis | Holy Cross | Away - HCHS [Directions] | L 1-5 | 2:15pm | |
| Wed., 4/23 | V Baseball | Holy Cross | Home - Washington Park [Directions] | L 2-13 | 2:15pm | |
| Wed., 4/23 | V Boys Tennis | Holy Cross | Home - Holy Cross HS [Directions] | L 5-4 | ||
| Wed., 4/23 | V Softball | Holy Cross | Away - HCHS [Directions] | L 0-14 | 2:15pm | |
| Wed., 4/23 | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | 3:30 p.m. | 2:15pm | |
| Thu., 4/24 | V Boys Golf | Crosby, Wilby | Home - Western Hills [Directions] | 2:30 p.m. | 1:45pm | |
| Thu., 4/24 | V Boys Golf | Wilby, Waterbury Coop | Away - Western Hills [Directions] | wilby 271 kennedy 241 Crosby 272 | 1:50pm | |
| Thu., 4/24 | V Girls Tennis | Wilby | Away - Wilby H.S. [Directions] | W 7-0 | ||
| Fri., 4/25 | V Baseball | Wilby | Away - Bucks Hill Park [Directions] | L 3-11 | 2:15pm | |
| Fri., 4/25 | V Boys Tennis | Woodland | Away - Woodland High School Tennis courts [Directions] | W 8-1 | 2:15pm | |
| Fri., 4/25 | V Softball | Wilby | Home - Crosby HS Field #1 [Directions] | W 20-5 | ||
| Mon., 4/28 | V Baseball | Seymour | Home - Washington Park [Directions] | L 11-0 | 2:15pm | |
| Mon., 4/28 | V Boys Golf | Watertown, St. Paul Catholic | Away - Crestbrook Park Golf Course [Directions] | 2:30 p.m. | 1:45pm | |
| Mon., 4/28 | V Boys Golf | Wolcott | Home - East Mountain [Directions] | Wolcott 183 Crosby 273 | 1:50pm | also w/ Sacred Heart |
| Mon., 4/28 | V Boys Tennis | Kennedy | Away - Chase Park [Directions] | L 5-4 | 2:15pm | |
| Mon., 4/28 | V Softball | Seymour | Away - Seymour High School [Directions] | L 0-14 | 2:30pm | |
| Mon., 4/28 | JV Softball | Seymour | Away - Bungay School [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 4/28 | V Girls Tennis | Seymour | Away - Seymour High School [Directions] | L 2-5 | 2:15pm | |
| Tue., 4/29 | V Baseball | Kennedy | Away - Waterville Park [Directions] | L 4-6 | 2:15pm | |
| Tue., 4/29 | FR Baseball | Kennedy | Away - Bucks Hill Park [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 4/29 | V Boys Outdoor Track | Seymour, Derby | Away - Seymour High School [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 4/29 | V Girls Outdoor Track | Seymour, Derby | Away - Seymour High School [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 4/29 | V Softball | Kennedy | Home - Municipal Stadium [Directions] | L 0-26(5) | ||
| Tue., 4/29 | JV Softball | Kennedy | Home - Municipal Stadium [Directions] | 3:30 p.m. | ||
| Tue., 4/29 | V Girls Tennis | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 3-4 | ||
| Thu., 5/1 | V Boys Tennis | Wolcott | Home - Wolcott HS [Directions] | L 9-0 | ||
| Fri., 5/2 | JV Softball | Derby | Away - Derby- Ryan Athletic Complex- softball field [Directions] | 3:30 p.m. | 2:30pm | |
| Sat., 5/3 | V Baseball | Derby | Home - Washington Park [Directions] | L 0-11 | 2:15pm | |
| Mon., 5/5 | V Baseball | Naugatuck | Home - Washington Park [Directions] | L 0-9 | 2:15pm | |
| Mon., 5/5 | V Boys Golf | Sacred Heart, Holy Cross | Home - Western Hills [Directions] | 2:30 p.m. | 1:45pm | |
| Mon., 5/5 | V Boys Golf | Woodland | Away [Directions] | woodland 179 Crosby 259 | 1:50pm | also w/ Torrington |
| Mon., 5/5 | V Boys Tennis | Naugatuck | Away - Naugatuck High School [Directions] | L 6-3 | 2:15pm | |
| Mon., 5/5 | V Softball | Naugatuck | Away - Breen Field [Directions] | L 1-9 | 4:30pm | |
| Mon., 5/5 | JV Softball | Naugatuck | Away - Breen Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 5/5 | V Girls Tennis | Naugatuck | Home - Montoe Park [Directions] | L 0-7 | ||
| Tue., 5/6 | JV Baseball | Naugatuck | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Golf | Torrington, Watertown | Away - Torrington Country Club [Directions] | 2:30 p.m. | 1:45pm | |
| Tue., 5/6 | V Boys Golf | Naugatuck | Away [Directions] | Naugatuck 201 Crosby 275 | 1:50pm | also w/ Holy Cross |
| Tue., 5/6 | V Boys Outdoor Track | Woodland, Torrington, Sacred Heart | Away - Woodland High School Track [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 5/6 | V Girls Outdoor Track | Woodland, Torrington, Sacred Heart | Away - Woodland High School Track [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 5/6 | V Girls Tennis | Wolcott | Home - Montoe Park [Directions] | L 1-6 | ||
| Wed., 5/7 | V Baseball | Wolcott | Away - Wolcott High School [Directions] | L 4-15 | 2:15pm | |
| Wed., 5/7 | V Softball | Wolcott | Home - Crosby HS Field #1 [Directions] | L 0-12 | ||
| Wed., 5/7 | JV Softball | Wolcott | Home - Crosby HS Field #2 [Directions] | 4:00 p.m. | ||
| Thu., 5/8 | V Softball | Derby | Away - Derby- Ryan Athletic Complex- softball field [Directions] | W 7-2 | 2:30pm | |
| Fri., 5/9 | V Baseball | Sacred Heart | Home - Washington Park [Directions] | W Forfeit | 2:15pm | |
| Fri., 5/9 | V Boys Outdoor Track | Wolcott, St. Paul Catholic | Away - Wolcott High School [Directions] | 3:30 p.m. | 9:30am | |
| Fri., 5/9 | V Boys Tennis | Sacred Heart | Home - Wilby HS [Directions] | W 8-1 | ||
| Fri., 5/9 | V Girls Outdoor Track | Wolcott, St. Paul Catholic | Away - Wolcott High School [Directions] | 3:30 p.m. | 9:30am | |
| Fri., 5/9 | V Softball | Sacred Heart | Away - Municipal Stadium | L 6-9 | 2:15pm | |
| Fri., 5/9 | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | 3:30 p.m. | 2:15pm | |
| Mon., 5/12 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | L 1-16 | 2:15pm | |
| Mon., 5/12 | V Boys Golf | St. Paul Catholic, Holy Cross | Home - East Mountain [Directions] | 2:30 p.m. | 1:50pm | |
| Mon., 5/12 | V Boys Tennis | Torrington | Away - Torrington High School [Directions] | L 5-4 | 2:15pm | |
| Mon., 5/12 | V Softball | Torrington | Home - Huntingdon Park [Directions] | L 0-22 | ||
| Mon., 5/12 | JV Softball | Torrington | Home - Huntingdon Park [Directions] | 3:30 p.m. | ||
| Mon., 5/12 | V Girls Tennis | Torrington | Home - Crosby HS [Directions] | W 4-3 | ||
| Tue., 5/13 | JV Baseball | Torrington | Away - Torrington High School [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 5/13 | V Boys Golf | St. Paul Catholic, Torrington | Away - Chippanee Golf Club [Directions] | 3:00 p.m. | 1:45pm | |
| Tue., 5/13 | V Boys Outdoor Track | Naugatuck, Wilby | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:15pm | |
| Tue., 5/13 | V Boys Tennis | Naugatuck | Home - Crosby HS [Directions] | L 5-4 | ||
| Tue., 5/13 | V Girls Outdoor Track | Naugatuck, Wilby | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:15pm | |
| Wed., 5/14 | V Baseball | Holy Cross | Away - HCHS [Directions] | L 5-12 | 2:15pm | |
| Wed., 5/14 | V Boys Tennis | Holy Cross | Away - HCHS [Directions] | W 7-2 | 2:15pm | |
| Wed., 5/14 | V Softball | Holy Cross | Home - Crosby HS Field #1 [Directions] | L 0-16(6) | ||
| Wed., 5/14 | JV Softball | Holy Cross | Home - Crosby HS Field #2 [Directions] | 3:30 p.m. | ||
| Wed., 5/14 | V Girls Tennis | Holy Cross | Home - Crosby HS [Directions] | L 0-7 | ||
| Thu., 5/15 | V Baseball | Wilby | Home - Washington Park [Directions] | L 1-6 | 2:15pm | |
| Thu., 5/15 | V Boys Golf | Torrington | Away [Directions] | Torrington 182 Crosby 268 | 1:30pm | also w/ Wolcott |
| Thu., 5/15 | V Boys Tennis | Wilby | Home - Crosby HS [Directions] | W 8-1 | ||
| Thu., 5/15 | V Softball | Wilby | Away - Bucks Hill Park [Directions] | W 18-1(5) | 2:15pm | |
| Thu., 5/15 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | W 7-0 | 2:15pm | |
| Mon., 5/19 | V Baseball | Kennedy | Home - Washington Park [Directions] | L 1-6 | 2:15pm | |
| Mon., 5/19 | V Boys Golf | Crosby, Wilby | Away - East Mountain [Directions] | 2:30 p.m. | 1:45pm | |
| Mon., 5/19 | V Boys Golf | Wilby, Waterbury Coop | Home - East Mountain [Directions] | wilby 235 kennedy239 Crosby 274 | 1:50pm | |
| Mon., 5/19 | V Boys Tennis | Wolcott | Away - Wolcott High School [Directions] | L 8-1 | 2:15pm | |
| Mon., 5/19 | V Softball | Kennedy | Away - Huntingdon Park [Directions] | W 8-7 | 5:30pm | |
| Mon., 5/19 | JV Softball | Kennedy | Away - Town Plot Park [Directions] | 3:30 p.m. | 2:15pm | |
| Mon., 5/19 | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | L 0-7 | 2:15pm | |
| Tue., 5/20 | V Boys Golf | Watertown | Away [Directions] | watertown 176 Crosby 284 | 1:50pm | also w/ Naugatuck |
| Tue., 5/20 | V Boys Outdoor Track | City Championships | Away - Holy Cross HS | 3:30 p.m. | 2:15pm | |
| Tue., 5/20 | V Boys Tennis | Watertown | Home - Crosby HS [Directions] | W 8-1 | ||
| Tue., 5/20 | V Girls Outdoor Track | City Championships | Away - Holy Cross HS | 3:30 p.m. | 2:15pm | |
| Tue., 5/20 | V Softball | Hamden | Away - HHS Softball Field [Directions] | L 1-7 | 2:15pm | |
| Tue., 5/20 | JV Softball | Hamden | Away - Bassett Field [Directions] | 3:45 p.m. | 2:15pm | |
| Wed., 5/21 | V Baseball | Naugatuck | Away - Rotary Field [Directions] | L 1-9 | 4:30pm | |
| Wed., 5/21 | V Boys Tennis | Sacred Heart | Home - Crosby HS [Directions] | L 6-3 | 2:15pm | |
| Wed., 5/21 | V Softball | Naugatuck | Home - Crosby HS Field #1 [Directions] | L 2-5 | ||
| Wed., 5/21 | JV Softball | Naugatuck | Home - Crosby HS Field #2 [Directions] | 3:45 p.m. | ||
| Wed., 5/21 | V Girls Tennis | Sacred Heart | Away - Fulton Park | W 4-3 | 2:15pm | |
| Wed., 5/21 | V Girls Tennis | Wilby | Away - Fulton Park [Directions] | W 6-1 | 2:15pm | |
| Fri., 5/23 | FR Baseball | Kennedy | Home - Waterville Park [Directions] | 3:45 p.m. | ||
| Fri., 5/23 | V Boys Golf | Woodland, Wolcott | Away - Oxford Greens [Directions] | 2:30 p.m. | 1:45pm | |
| Fri., 5/23 | V Boys Tennis | Kennedy | Home - Crosby HS [Directions] | W 7-2 | ||
| Tue., 5/27 | V Boys Golf | Holy Cross | Home - East Mountain [Directions] | 2:30 p.m. | 1:50pm | also w/ Sacred Heart |
| Wed., 5/28 | V Baseball | Kaynor Tech | Home - Kaynor Tech [Directions] | L 9-10(10) | 2:15pm | |
| Wed., 5/28 | V Boys Golf | City Championships | Away - Waterbury CC | TBA | TBA | |
| Wed., 5/28 | V Boys Outdoor Track | NVL Championships | Away | TBA | TBA | |
| Wed., 5/28 | V Girls Outdoor Track | NVL Championships | Away | TBA | 2:15pm | |
| Thu., 5/29 | V Boys Outdoor Track | NVL JV Meet | Away | TBA | TBA | |
| Thu., 5/29 | V Girls Outdoor Track | NVL JV Meet | Away | TBA | 2:15pm | |
| Tue., 6/3 | V Boys Golf | Naugatuck, Holy Cross | Home - Western Hills [Directions] | 2:30 p.m. | 1:45pm | |
| Thu., 6/5 | V Boys Golf | NVL Tournament | Away - Watertown C.C. | 9:00 a.m. | ||
| Thu., 6/5 | V Boys Golf | NVL Championships | Away - Watertown CC | TBA | TBA | |