| Wilby 2016-17 Athletic Events Schedule | |||||||
|---|---|---|---|---|---|---|---|
| 376 Events Listed || Go Back || | |||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Bus Time | Note |
| TBA | JV Baseball | Oxford | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Baseball | Watertown | Away - Veterans Park [Directions] | TBA | 9:30 am | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | |||
| TBA | JV Baseball | Crosby | Away - Crosby HS [Directions] | TBA | 2:15 pm | ||
| TBA | JV Baseball | Sacred Heart | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Baseball | WCA | Away - Washington Park [Directions] | TBA | 11:30 am | ||
| TBA | JV Baseball | St. Paul Catholic | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Baseball | Holy Cross | Away - Holy Cross HS [Directions] | TBA | 2:15 pm | ||
| TBA | JV Baseball | Kennedy | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Baseball | Sacred Heart | Away - Fulton Park | TBA | |||
| TBA | JV Baseball | Holy Cross | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Baseball | WCA | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | TBA | 2:15 pm | ||
| TBA | FR Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | TBA | No bus | ||
| TBA | FR Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | TBA | No bus | ||
| TBA | FR Boys Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | TBA | |||
| TBA | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | TBA | No bus | ||
| TBA | JV Football | Kennedy | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Football | Naugatuck | Away - Naugatuck HS [Directions] | TBA | |||
| TBA | FR Football | Watertown | Home - Wilby H.S. [Directions] | Cancelled | Cancelled | ||
| TBA | JV Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | TBA | 9:45 | ||
| TBA | JV Boys Soccer | Kennedy | Away - West Side MS [Directions] | TBA | |||
| TBA | JV Boys Soccer | Holy Cross | Away - Lower Murray Park [Directions] | TBA | 2:15 | ||
| TBA | JV Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | TBA | 2:30 | ||
| TBA | JV Boys Soccer | Seymour | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 2:15 | ||
| TBA | JV Boys Soccer | Torrington | Away - Torrington HS [Directions] | TBA | 2:15 | ||
| TBA | V Boys Swimming and Diving | Bristol Eastern | Home - Wilby H.S. [Directions] | TBA | |||
| TBA | JV Girls Basketball | Ansonia | Home - Reggie O'Brien Gymnasium [Directions] | TBA | |||
| TBA | JV Girls Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | TBA | |||
| TBA | JV Girls Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | TBA | |||
| TBA | JV Softball | Watertown | Away - Veteran's Park #1 [Directions] | 3:30 p.m. | 2:15 pm | ||
| TBA | JV Softball | WCA | Away - Huntingdon Park [Directions] | TBA | 2:15 pm | ||
| TBA | JV Softball | Holy Cross | Home - Bucks Hill Park [Directions] | TBA | 2:15 pm | ||
| TBA | JV Softball | Sacred Heart | Home - Bucks Hill Park [Directions] | TBA | 2:15 | ||
| TBA | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | TBA | 2:15 pm | ||
| TBA | JV Softball | Oxford | Away - Oxford HS [Directions] | TBA | 2:30 pm | ||
| TBA | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 2:30 pm | ||
| TBA | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | TBA | L 0-7 | 2:15 pm | |
| Fri., 9/9 | V Football | WCA | Home - Municipal Stadium [Directions] | 7:00 p.m. | L 13-58 | 5:15 | 2 buses |
| Fri., 9/9 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | L 0-7 | 2:15 | |
| Fri., 9/9 | V Girls Volleyball | Wolcott | Home - Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 0-3 | ||
| Fri., 9/9 | JV Girls Volleyball | Wolcott | Home - Reggie O'Brien Gymnasium [Directions] | 4:30 p.m. | |||
| Tue., 9/13 | V Boys Cross Country | Crosby, Derby, Watertown | Away - Derby- Ryan athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | 2:30 | @ Derby | |
| Tue., 9/13 | V Girls Cross Country | Derby, Crosby, Watertown | Away [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 9/13 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:00 p.m. | L 0-3 | 2:30 | |
| Tue., 9/13 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 3:30 p.m. | |||
| Wed., 9/14 | V Boys Soccer | Watertown | Home - Municipal Stadium [Directions] | 6:00 p.m. | L 0-7 | ||
| Thu., 9/15 | V Football | Torrington | Home - Municipal Stadium [Directions] | 6:00 p.m. | L 7-48 | 4:15 | 2 buses |
| Thu., 9/15 | JV Boys Soccer | Watertown | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Thu., 9/15 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 0-3 | 3:15 | |
| Thu., 9/15 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 4:30 p.m. | |||
| Fri., 9/16 | V Boys Soccer | Kennedy | Away - West Side MS [Directions] | 3:30 p.m. | L 3-10 | 2:15 | |
| Fri., 9/16 | V Girls Swimming and Diving | Holy Cross | Away - Wilby HS [Directions] | 4:00 p.m. | |||
| Fri., 9/16 | V Girls Volleyball | Seymour | Home - Wilby H.S. [Directions] | 4:30 p.m. | L 0-3 | ||
| Fri., 9/16 | JV Girls Volleyball | Seymour | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Sat., 9/17 | JV Football | Torrington | Away - Torrington HS [Directions] | 10:30 a.m. | 9:00 | ||
| Tue., 9/20 | V Boys Cross Country | St. Paul Catholic, Woodland, WCA | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 9/20 | V Boys Soccer | Ansonia | Home - Municipal Stadium [Directions] | 6:00 p.m. | L 1-6 | ||
| Tue., 9/20 | V Girls Cross Country | St. Paul Catholic, Woodland, WCA | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 9/20 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | L 0-3 | 3:15 | |
| Tue., 9/20 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | |||
| Wed., 9/21 | JV Boys Soccer | Ansonia | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Wed., 9/21 | V Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 5:00 p.m. | L 0-3 | 2:15 | |
| Wed., 9/21 | JV Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 3:30 p.m. | |||
| Thu., 9/22 | FM Football | Holy Cross | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Thu., 9/22 | JV Boys Soccer | Sacred Heart | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Fri., 9/23 | V Boys Soccer | Sacred Heart | Home - Municipal Stadium [Directions] | 3:30 p.m. | L 104 | 2:15 | |
| Fri., 9/23 | V Girls Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | 6:00 | ||
| Fri., 9/23 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 5:15 p.m. | L 0-3 | 2:30 | |
| Fri., 9/23 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:00 p.m. | |||
| Sat., 9/24 | V Football | Holy Cross | Away - Holy Cross Alumni Field [Directions] | 1:00 p.m. | L 12-42 | 11:15 | 2 buses |
| Tue., 9/27 | V Boys Cross Country | Oxford, Naugatuck, Sacred Heart | Away - OHS Track [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 9/27 | V Boys Soccer | WCA | Away - Municipal Stadium [Directions] | 6:00 p.m. | L 2-3 | ||
| Tue., 9/27 | V Girls Cross Country | Oxford, Naugatuck, Sacred Heart | Away [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 9/27 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Wilby H.S. [Directions] | 4:00 p.m. | |||
| Tue., 9/27 | V Girls Volleyball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | ||
| Tue., 9/27 | JV Girls Volleyball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Wed., 9/28 | JV Boys Soccer | WCA | Away - Hamilton Park [Directions] | 3:30 p.m. | 2:15 | ||
| Thu., 9/29 | JV Boys Soccer | Woodland | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Thu., 9/29 | V Girls Volleyball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | ||
| Thu., 9/29 | JV Girls Volleyball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Fri., 9/30 | V Football | Kennedy | Away - Municipal Stadium [Directions] | 7:00 p.m. | L 0-27 | 5:00 | 2 buses |
| Fri., 9/30 | V Boys Soccer | Woodland | Home - Municipal Stadium [Directions] | 3:30 p.m. | L 4-7 | 2:15 | |
| Fri., 9/30 | V Girls Swimming and Diving | Oxford | Home - Wilby H.S. [Directions] | 4:00 p.m. | |||
| Fri., 9/30 | V Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 5:00 p.m. | L 1-3 | 2:30 | |
| Fri., 9/30 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 3:45 p.m. | |||
| Tue., 10/4 | V Boys Cross Country | Holy Cross, Seymour, Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 10/4 | V Boys Soccer | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 1-4 | 2:15 | |
| Tue., 10/4 | V Girls Cross Country | Torrington, Holy Cross, Seymour | Away [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 10/4 | V Girls Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | 2:30 | ||
| Tue., 10/4 | V Girls Volleyball | Torrington | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | ||
| Tue., 10/4 | JV Girls Volleyball | Torrington | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Wed., 10/5 | FR Football | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:15 | ||
| Thu., 10/6 | V Football | Naugatuck | Home - Municipal Stadium [Directions] | 6:00 p.m. | L 0-47 | 4:15 | 2 buses |
| Fri., 10/7 | V Boys Soccer | Wolcott | Home - Wilby H.S. [Directions] | 3:45 p.m. | L 1-3 | ||
| Fri., 10/7 | V Girls Swimming and Diving | Woodland | Home - Wilby H.S. [Directions] | 4:00 p.m. | |||
| Fri., 10/7 | V Girls Volleyball | St. Paul Catholic | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | ||
| Fri., 10/7 | JV Girls Volleyball | St. Paul Catholic | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Tue., 10/11 | V Boys Cross Country | Ansonia, Wolcott, Kennedy | Away - Wolcott HS [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 10/11 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 4:00 p.m. | L 2-3 | 2:30 | |
| Tue., 10/11 | V Girls Cross Country | Wolcott, Ansonia, Kennedy | Away [Directions] | 3:45 p.m. | 2:30 | ||
| Tue., 10/11 | V Girls Swimming and Diving | Watertown | Home - Wilby H.S. [Directions] | 4:00 p.m. | |||
| Wed., 10/12 | V Boys Soccer | WCA | Home - Municipal Stadium [Directions] | 6:00 p.m. | W 4-0 | ||
| Thu., 10/13 | V Girls Volleyball | Naugatuck | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | ||
| Thu., 10/13 | JV Girls Volleyball | Naugatuck | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Fri., 10/14 | V Boys Cross Country | City Championship | Away - Montoe Park | 3:45 p.m. | 2:30 | ||
| Fri., 10/14 | V Football | Crosby | Home - Municipal Stadium [Directions] | 7:00 p.m. | L 14-68 | 5:15 | 2 buses |
| Fri., 10/14 | V Boys Soccer | Seymour | Home - Wilby H.S. [Directions] | 3:45 p.m. | L 1-3 | ||
| Fri., 10/14 | V Girls Cross Country | City Championship | Away - Montoe Park | 3:45 p.m. | 2:30 | ||
| Fri., 10/14 | V Girls Swimming and Diving | Seymour | Away - Seymour HS [Directions] | 4:00 p.m. | 2:30 | ||
| Fri., 10/14 | V Girls Volleyball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | ||
| Fri., 10/14 | JV Girls Volleyball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Sat., 10/15 | JV Football | Crosby | Away - Crosby HS [Directions] | 11:00 a.m. | 9:30 | ||
| Tue., 10/18 | V Girls Swimming and Diving | Sacred Heart | Home - Wilby H.S. [Directions] | 4:00 p.m. | |||
| Tue., 10/18 | V Girls Volleyball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | L 1-3 | ||
| Tue., 10/18 | JV Girls Volleyball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Wed., 10/19 | V Boys Cross Country | NVL Championship | Away | 3:45 p.m. | 2:15 | ||
| Wed., 10/19 | V Boys Soccer | Oxford | Home - Municipal Stadium [Directions] | 6:00 p.m. | L 0-2 | ||
| Wed., 10/19 | V Girls Cross Country | NVL Championship | Away - Veterens | 3:45 p.m. | 2:15 | ||
| Thu., 10/20 | JV Boys Soccer | Oxford | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Fri., 10/21 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | L 2-4 | 4:45 | |
| Fri., 10/21 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | 2:30 | ||
| Fri., 10/21 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 5:00 p.m. | L 0-3 | 2:30 | |
| Fri., 10/21 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | |||
| Mon., 10/24 | V Boys Soccer | Crosby | Home - Municipal Stadium [Directions] | 7:15 p.m. | W 4-2 | ||
| Tue., 10/25 | JV Boys Soccer | Crosby | Home - Wilby H.S. [Directions] | 3:30 p.m. | |||
| Wed., 10/26 | V Boys Soccer | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | L 2-5 | 4:45 | |
| Wed., 10/26 | V Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:00 p.m. | L 0-3 | 2:30 | |
| Wed., 10/26 | JV Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 3:30 p.m. | |||
| Fri., 10/28 | V Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 0-36 | 4:45 | 2 buses |
| Sat., 10/29 | V Boys Cross Country | Class Championship | Away | TBA | TBA | ||
| Sat., 10/29 | JV Football | Watertown | Home - Wilby H.S. [Directions] | 10:30 a.m. | |||
| Sat., 10/29 | V Girls Cross Country | Class Championship | Away | TBA | TBA | ||
| Thu., 11/3 | V Football | Oxford | Home - Municipal Stadium [Directions] | 6:00 p.m. | L 6-38 | 4:15 | 2 buses |
| Sat., 11/5 | FM Football | Oxford | Away - @Oxford [Directions] | 10:30 a.m. | |||
| Fri., 11/11 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | L 6-54 | 4:45 | 2 buses |
| Sat., 11/12 | FM Football | St. Paul Catholic | Home - Wilby H.S. [Directions] | 12:00 p.m. | |||
| Thu., 11/17 | JV Football | Amistad | Home - Wilby H.S. [Directions] | 3:00 p.m. | |||
| Wed., 11/23 | V Football | Sacred Heart | Away - Municipal Stadium | 6:00 p.m. | L 14-68 | 4:15 | 2 buses |
| Tue., 12/6 | V Boys Basketball | Pomperaug (Scrim.) | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | |||
| Tue., 12/13 | V Boys Basketball | Bassick (Scrim.) | Home - Reggie O'Brien Gymnasium [Directions] | 4:00 p.m. | |||
| Tue., 12/13 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | L 14-56 | 4:15 | |
| Tue., 12/13 | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | |||
| Thu., 12/15 | V Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 6:00 p.m. | L 11-49 | 2:45 | |
| Thu., 12/15 | JV Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 4:30 p.m. | |||
| Fri., 12/16 | V Boys Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 pm | ||
| Fri., 12/16 | V Girls Basketball | Seymour | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 11-62 | ||
| Fri., 12/16 | JV Girls Basketball | Seymour | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Sat., 12/17 | V Boys Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 7:15 am | ||
| Tue., 12/20 | V Boys Basketball | Derby | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 79-32 | ||
| Tue., 12/20 | JV Boys Basketball | Derby | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 12/20 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | L 23-63 | 3:45 | |
| Tue., 12/20 | JV Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:30 p.m. | |||
| Wed., 12/21 | V Boys Swimming and Diving | Torrington | Home - Wilby H.S. [Directions] | 6:00 p.m. | |||
| Wed., 12/21 | V Girls Basketball | Kaynor Tech | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 26-61 | ||
| Wed., 12/21 | JV Girls Basketball | Kaynor Tech | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Thu., 12/22 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 55-62 | 4:15 | From North End Rec |
| Thu., 12/22 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | |||
| Thu., 12/22 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | 2:15 | ||
| Thu., 12/22 | V Girls Basketball | Naugatuck | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 14-58 | ||
| Thu., 12/22 | JV Girls Basketball | Naugatuck | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away - Floyd Little Athletic Center | 9:30 a.m. | 7:30 am | ||
| Fri., 12/30 | V Boys Basketball | Kaynor Tech | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 64-54 | ||
| Fri., 12/30 | JV Boys Basketball | Kaynor Tech | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 12/30 | FR Boys Basketball | Kaynor Tech | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Mon., 1/2 | FR Boys Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 12:00 p.m. | |||
| Tue., 1/3 | V Boys Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 75-76 | ||
| Tue., 1/3 | JV Boys Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 1/3 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | 2:30 | ||
| Tue., 1/3 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | L 18-49 | ||
| Tue., 1/3 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | |||
| Thu., 1/5 | FR Boys Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | |||
| Fri., 1/6 | V Boys Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 65-74 | ||
| Fri., 1/6 | JV Boys Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 1/6 | V Boys Indoor Track | Elm City Relays | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 pm | ||
| Fri., 1/6 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 6:30 p.m. | 5:00 | ||
| Sat., 1/7 | V Boys Indoor Track | Elm City Relays | Away - Floyd Little Athletic Center | 9:00 a.m. | 7:15 am | ||
| Wed., 1/11 | V Boys Basketball | Woodland | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 75-22 | ||
| Wed., 1/11 | JV Boys Basketball | Woodland | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Wed., 1/11 | V Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 7:00 p.m. | L 22-67 | 4:15 | |
| Wed., 1/11 | JV Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 4:45 p.m. | |||
| Thu., 1/12 | FR Boys Basketball | Woodland | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | |||
| Thu., 1/12 | V Boys Swimming and Diving | Naugatuck | Home - Wilby H.S. [Directions] | 6:00 p.m. | |||
| Fri., 1/13 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | L 55-86 | No bus | |
| Fri., 1/13 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | |||
| Fri., 1/13 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 3:30 p.m. | 2:30 | ||
| Fri., 1/13 | V Girls Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 38-64 | ||
| Fri., 1/13 | JV Girls Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Mon., 1/16 | FR Boys Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 12:00 p.m. | |||
| Wed., 1/18 | V Boys Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 50-61 | ||
| Wed., 1/18 | JV Boys Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Wed., 1/18 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 27-79 | ||
| Wed., 1/18 | JV Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | |||
| Thu., 1/19 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | 5:30 | ||
| Thu., 1/19 | V Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 27-50 | ||
| Thu., 1/19 | JV Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:15 p.m. | |||
| Fri., 1/20 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 65-68 | 3:15 | From Wilby |
| Fri., 1/20 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | |||
| Fri., 1/20 | FR Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 3:00 p.m. | 2:15 | ||
| Fri., 1/20 | V Boys Swimming and Diving | Oxford | Home - Wilby H.S. [Directions] | 6:00 p.m. | |||
| Fri., 1/20 | V Girls Basketball | Ansonia | Home - Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 28-45 | ||
| Sat., 1/21 | V Boys Indoor Track | SCC Coaches Invitational | Away - Floyd Athletic Center | 9:00 a.m. | 7:15 am | ||
| Wed., 1/25 | V Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 7:00 p.m. | W 70-57 | No bus | |
| Wed., 1/25 | JV Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | |||
| Wed., 1/25 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS [Directions] | 5:30 p.m. | 4:30 | ||
| Thu., 1/26 | FR Boys Basketball | Torrington | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | |||
| Fri., 1/27 | V Boys Basketball | Torrington | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 86-71 | ||
| Fri., 1/27 | JV Boys Basketball | Torrington | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 1/27 | V Boys Swimming and Diving | Woodland | Home - Wilby H.S. [Directions] | 6:00 p.m. | |||
| Fri., 1/27 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | L 29-61 | 4:00 | |
| Fri., 1/27 | JV Girls Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | |||
| Mon., 1/30 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | W 83-47 | 2:45 | From Wilby |
| Mon., 1/30 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 4:30 p.m. | |||
| Mon., 1/30 | V Boys Indoor Track | NVL Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | 2:30 pm | ||
| Mon., 1/30 | V Girls Basketball | Oxford | Home - Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | L 20-50 | ||
| Mon., 1/30 | JV Girls Basketball | Oxford | Home - Reggie O'Brien Gymnasium [Directions] | Cancelled | Cancelled | ||
| Wed., 2/1 | V Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 72-80 | No bus | |
| Wed., 2/1 | JV Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | |||
| Wed., 2/1 | V Girls Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 26-49 | ||
| Wed., 2/1 | JV Girls Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 2/3 | V Boys Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 67-75(OT) | ||
| Fri., 2/3 | JV Boys Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 2/3 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | L 31-75 | ||
| Fri., 2/3 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | |||
| Wed., 2/8 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | L 65-76 | No bus | |
| Wed., 2/8 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | |||
| Wed., 2/8 | V Girls Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 34-61 | ||
| Wed., 2/8 | JV Girls Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Sat., 2/11 | V Boys Indoor Track | Class L Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:00 pm | ||
| Tue., 2/14 | V Boys Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 83-68 | ||
| Tue., 2/14 | JV Boys Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 2/14 | FR Boys Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | |||
| Tue., 2/14 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | 5:30 | ||
| Tue., 2/14 | V Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 7:00 p.m. | L 28-56 | ||
| Tue., 2/14 | JV Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | |||
| Wed., 2/15 | FR Boys Basketball | Wolcott | Home - Reggie O'Brien Gymnasium [Directions] | 5:00 p.m. | |||
| Wed., 2/15 | V Girls Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 31-58 | ||
| Thu., 2/16 | V Boys Basketball | Wolcott | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 80-59 | ||
| Thu., 2/16 | JV Boys Basketball | Wolcott | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Thu., 2/16 | V Girls Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 3:30 p.m. | L 26-64 | ||
| Fri., 2/17 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 61-72 | No bus | |
| Fri., 2/17 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | |||
| Fri., 2/17 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:15 | ||
| Fri., 2/17 | V Boys Swimming and Diving | Seymour | Home - Wilby H.S. [Directions] | 4:00 p.m. | |||
| Sat., 2/18 | V Boys Indoor Track | State Open Championships | Away - Floyd Little Athletic Center | TBA | TBA | ||
| Wed., 2/22 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | L 65-70 | 4:15 | From North End Rec |
| Wed., 2/22 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | |||
| Wed., 2/22 | FR Boys Basketball | Seymour | Away - Seymour HS [Directions] | 3:30 p.m. | 2:30 | ||
| Fri., 2/24 | V Boys Basketball | Hartford Public | Home - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | L 61-75(OT) | ||
| Fri., 2/24 | JV Boys Basketball | Hartford Public | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | |||
| Mon., 4/3 | V Baseball | Oxford | Home - Wilby H.S. [Directions] | 4:00 p.m. | L 2-21 | ||
| Mon., 4/3 | V Boys Tennis | Woodland | Away - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 2-7 | 2:15 pm | |
| Mon., 4/3 | V Girls Tennis | Woodland | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Wed., 4/5 | V Boys Outdoor Track | Holy Cross, WCA, Kaynor Tech | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Wed., 4/5 | V Girls Outdoor Track | Holy Cross, WCA, Kaynor Tech | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Wed., 4/5 | V Softball | Oxford | Away - OHS Softball Field [Directions] | 3:45 p.m. | L 0-20 | 2:15 pm | |
| Fri., 4/7 | V Boys Tennis | Kennedy | Home - Bucks Hill Park [Directions] | 3:30 p.m. | W 6-3 | 2:15 pm | |
| Sat., 4/8 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 1:00 p.m. | L 7-3 | 2:15 pm | |
| Sat., 4/8 | V Boys Outdoor Track | Crosby, Naugatuck | Away - Naugatuck HS [Directions] | 10:00 a.m. | 2:30 pm | ||
| Sat., 4/8 | V Girls Outdoor Track | Crosby, Naugatuck | Away - Naugatuck HS [Directions] | 10:00 a.m. | 2:30 pm | ||
| Sat., 4/8 | V Softball | Wolcott Tech | Away - Wolcott Tech Softball Field [Directions] | 11:30 a.m. | L 5-22 | 2:15 pm | |
| Mon., 4/10 | V Baseball | Ansonia | Home - Wilby H.S. [Directions] | 3:45 p.m. | L 27-2 | ||
| Mon., 4/10 | V Softball | Ansonia | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 3-11 | 2:15 pm | |
| Mon., 4/10 | V Girls Tennis | Ansonia | Home - Bucks Hill Park [Directions] | 10:00 a.m. | L 0-7 | 2:15 pm | |
| Tue., 4/11 | JV Baseball | Ansonia | Home - Wilby H.S. [Directions] | 2:00 p.m. | |||
| Wed., 4/12 | V Baseball | Kennedy | Away - Waterville Park [Directions] | 11:00 a.m. | L 6-5 | 9:30 am | |
| Wed., 4/12 | V Softball | Kennedy | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 5-23 | 2:15 pm | |
| Wed., 4/12 | JV Softball | Kennedy | Home - Bucks Hill Park [Directions] | 3:30 p.m. | 2:15 pm | ||
| Thu., 4/13 | V Baseball | Crosby | Away - Crosby HS [Directions] | 11:00 a.m. | L 13-7 | 2:15 pm | |
| Thu., 4/13 | V Boys Tennis | Crosby | Away - Crosby HS [Directions] | 11:00 a.m. | W 8-1 | 2:15 pm | |
| Thu., 4/13 | V Softball | Crosby | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 6-26 | 2:15 pm | |
| Thu., 4/13 | JV Softball | Crosby | Home - Bucks Hill Park [Directions] | 3:30 p.m. | 2:15 pm | ||
| Fri., 4/14 | V Boys Tennis | Torrington | Home - Bucks Hill Park [Directions] | 11:00 a.m. | L 0-9 | ||
| Mon., 4/17 | V Baseball | Sacred Heart | Home - Municipal Stadium [Directions] | 3:30 p.m. | L 1-18 | 2:15 pm | |
| Mon., 4/17 | V Boys Golf | Holy Cross | Home - Western Hills [Directions] | 2:30 p.m. | HC 178 Kennedy 272 | 1:45pm | |
| Mon., 4/17 | V Boys Golf | St. Paul Catholic | Away [Directions] | 3:45 p.m. | St. Paul: 182 Wilby: 256 | 2:15 pm | |
| Mon., 4/17 | V Boys Tennis | Sacred Heart | Home - Bucks Hill Park [Directions] | 3:30 p.m. | W 5-4 | 2:15 pm | |
| Mon., 4/17 | V Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | 3:45 p.m. | L 10-23 | 2:30 pm | |
| Mon., 4/17 | V Girls Tennis | Sacred Heart | Away - Fulton Park | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Tue., 4/18 | V Boys Outdoor Track | Seymour, Oxford | Away - Seymour HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Tue., 4/18 | V Boys Tennis | Watertown | Away - Crestbrook Park [Directions] | 3:30 p.m. | L 3-6 | 2:30 pm | |
| Tue., 4/18 | V Girls Outdoor Track | Seymour, Oxford | Away - Seymour HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Tue., 4/18 | JV Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | 3:45 p.m. | 2:30 pm | ||
| Wed., 4/19 | V Baseball | Torrington | Home - Municipal Stadium [Directions] | 3:45 p.m. | L 2-12 | 2:15 pm | |
| Wed., 4/19 | V Boys Golf | Crosby | Away - East Mountain [Directions] | 1:00 p.m. | Crosby253 Kennedy 265 | 1:45pm | |
| Wed., 4/19 | V Boys Golf | Holy Cross, Sacred Heart | Home - Western Hills [Directions] | 2:30 p.m. | Holy Cross: 185 Sacred Heart: 209 Wilby: 260 | 1:15 pm | |
| Wed., 4/19 | V Boys Tennis | Kennedy | Away - Chase Park [Directions] | 3:30 p.m. | W 9-0 | 2:15 pm | |
| Wed., 4/19 | V Girls Tennis | Kennedy | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Thu., 4/20 | JV Baseball | Torrington | Home - Wilby H.S. [Directions] | 3:45 p.m. | |||
| Thu., 4/20 | V Boys Golf | Wolcott | Home - Western Hills [Directions] | 2:30 p.m. | Wolcott 179 Kennedy 267 | 1:45pm | |
| Thu., 4/20 | V Softball | Watertown | Away - Swift MS [Directions] | 3:30 p.m. | L 0-19 | 2:15 pm | |
| Fri., 4/21 | V Boys Golf | Sacred Heart, Crosby | Away - East Mountain Golf Course | 2:30 p.m. | Sacred Heart: 173 Crosby: 244 Wilby: 260 | 2:15 pm | |
| Fri., 4/21 | V Softball | WCA | Away - Municipal Stadium [Directions] | 3:30 p.m. | L 0-15 | 2:15 pm | |
| Sat., 4/22 | V Baseball | WCA | Away - Washington Park [Directions] | 11:00 a.m. | L 16-6 | 9:30 am | |
| Mon., 4/24 | V Baseball | St. Paul Catholic | Home - Wilby H.S. [Directions] | 4:00 p.m. | L 3-21 | ||
| Mon., 4/24 | V Boys Golf | Naugatuck | Home - Western Hills [Directions] | 2:30 p.m. | Naugatuck 246 Kennedy 280 | 1:45pm | |
| Mon., 4/24 | V Boys Golf | Watertown | Away [Directions] | 3:45 p.m. | Watertown: 197 Wilby: 260 | 2:15 pm | |
| Mon., 4/24 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:45 p.m. | L 0-18 | 2:15 pm | |
| Mon., 4/24 | V Girls Tennis | St. Paul Catholic | Away - Peck Park, Bristol [Directions] | 3:45 p.m. | L 0-7 | 2:15 pm | |
| Wed., 4/26 | V Boys Golf | Holy Cross, Torrington | Home - Western Hills [Directions] | 2:30 p.m. | Holy Cross: 178 Torrington: 194 Wilby: 256 | 1:15 pm | |
| Wed., 4/26 | V Boys Golf | Seymour | Away - Oxford Greens [Directions] | 2:30 p.m. | SEYMOUR 213 KENNEDY 268 | 1:45pm | |
| Wed., 4/26 | V Boys Outdoor Track | Watertown, Kennedy | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Wed., 4/26 | V Girls Outdoor Track | Watertown, Kennedy | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Thu., 4/27 | V Boys Golf | St. Paul Catholic | Away - Chippanee G.C. [Directions] | 2:30 p.m. | St Paul 205 Kennedy 249 | 1:45pm | |
| Thu., 4/27 | V Softball | Holy Cross | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 0-22 | 2:15 pm | |
| Thu., 4/27 | V Girls Tennis | Naugatuck | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Fri., 4/28 | V Baseball | Platt Tech | Away - Platt Tech baseball field [Directions] | 3:45 p.m. | L 12-8 | 2:15 pm | |
| Fri., 4/28 | V Boys Tennis | Naugatuck | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 1-8 | 2:15 pm | |
| Fri., 4/28 | V Softball | Naugatuck | Home - Bucks Hill Park [Directions] | 3:45 p.m. | L 0-15 | 2:30 pm | |
| Fri., 4/28 | JV Softball | Naugatuck | Home - Bucks Hill Park [Directions] | 3:30 p.m. | 2:30 pm | ||
| Fri., 4/28 | V Girls Tennis | Torrington | Away - Torrington HS [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Sat., 4/29 | JV Baseball | Platt Tech | Home - Wilby H.S. [Directions] | Cancelled | Cancelled | ||
| Mon., 5/1 | V Boys Golf | Woodland | Away [Directions] | Cancelled | Cancelled | 2:15 pm | |
| Mon., 5/1 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | L 7-2 | 2:15 pm | |
| Mon., 5/1 | V Softball | Woodland | Away - Woodland Softball Field [Directions] | 3:30 p.m. | L 1-24 | 2:15 pm | |
| Mon., 5/1 | JV Softball | Woodland | Away - Woodland Softball Field [Directions] | 5:00 p.m. | 2:15 pm | ||
| Tue., 5/2 | V Baseball | Holy Cross | Home - Wilby HS [Directions] | 3:30 p.m. | L 2-24 | 2:15 pm | |
| Tue., 5/2 | V Boys Golf | Crosby, St. Paul Catholic | Away - East Mountain [Directions] | 2:30 p.m. | Wilby 250; Crosby n/s | 1:15 pm | |
| Tue., 5/2 | V Boys Golf | Watertown | Home - Western Hills [Directions] | 2:30 p.m. | Watertown 204 Kennedy 264 Watertown 204 Kennedy264 | 1:45pm | |
| Tue., 5/2 | V Boys Outdoor Track | Woodland, St. Paul Catholic | Away - Woodland HS Track [Directions] | 3:30 p.m. | 2:30 pm | ||
| Tue., 5/2 | V Boys Tennis | Wolcott | Away - Wolcott HS [Directions] | 3:30 p.m. | L 1-8 | 2:15 pm | |
| Tue., 5/2 | V Girls Outdoor Track | Woodland, St. Paul Catholic | Away - Woodland HS Track [Directions] | 3:30 p.m. | 2:30 pm | ||
| Tue., 5/2 | V Girls Tennis | Wolcott | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Wed., 5/3 | V Baseball | Derby | Away - Derby -Ryan Athletic Complex-baseball field [Directions] | 3:45 p.m. | W 10-3 | 2:15 pm | |
| Wed., 5/3 | V Softball | Derby | Away - Derby- Ryan Athletic Complex- softball field [Directions] | 4:00 p.m. | L 1-16 | 2:30 pm | |
| Wed., 5/3 | V Girls Tennis | Seymour | Away - Seymour HS [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Thu., 5/4 | V Baseball | Kennedy | Home - Municipal Stadium [Directions] | 6:30 p.m. | W 6-1 | ||
| Thu., 5/4 | V Boys Golf | Crosby | Home - Western Hills [Directions] | Cancelled | Cancelled | 1:15 pm | |
| Thu., 5/4 | V Boys Tennis | Watertown | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 7-2 | 2:15 pm | |
| Thu., 5/4 | V Softball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | L 0-15 | 2:15 pm | |
| Thu., 5/4 | JV Softball | Kennedy | Away - Town Plot Park [Directions] | 3:30 p.m. | 2:15 pm | ||
| Thu., 5/4 | V Girls Tennis | Watertown | Away - Crestbrook Park [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Mon., 5/8 | V Baseball | Sacred Heart | Away - Municipal Stadium | 3:45 p.m. | L 8-2 | 2:15 pm | |
| Mon., 5/8 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:45 p.m. | Woodland 173 Kennedy 273 | 1:45pm | |
| Mon., 5/8 | V Boys Golf | Torrington | Away [Directions] | 3:45 p.m. | Torrington 182; Wilby 245 | 2:15 pm | |
| Mon., 5/8 | V Boys Tennis | Sacred Heart | Away - Fulton Park | 3:30 p.m. | T 3-3 | 2:15 pm | |
| Mon., 5/8 | V Softball | Sacred Heart | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 0-21 | 2:15 pm | |
| Mon., 5/8 | V Girls Tennis | Sacred Heart | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 0-7 | 2:15 pm | |
| Tue., 5/9 | V Girls Tennis | Crosby | Away - Montoe Park [Directions] | 3:30 p.m. | L 1-5 | 2:15 pm | |
| Tue., 5/9 | V Girls Tennis | Crosby | Home - Montoe Park [Directions] | 4:30 p.m. | L 2-5 | ||
| Wed., 5/10 | V Baseball | Crosby | Home - Wilby H.S. [Directions] | 3:30 p.m. | L 7-10 | ||
| Wed., 5/10 | V Boys Outdoor Track | Torrington, Sacred Heart | Away - Torrington HS [Directions] | 3:45 p.m. | 2:30 pm | ||
| Wed., 5/10 | V Boys Tennis | Crosby | Home - Bucks Hill Park [Directions] | 3:30 p.m. | W 7-2 | 2:15 pm | |
| Wed., 5/10 | V Girls Outdoor Track | Torrington, Sacred Heart | Away - Torrington HS [Directions] | 3:45 p.m. | 2:30 pm | ||
| Wed., 5/10 | V Softball | Crosby | Away - Crosby HS Field #1 [Directions] | 4:00 p.m. | L 8-9 | 2:45 pm | |
| Wed., 5/10 | JV Softball | Crosby | Away - Crosby HS Field #2 [Directions] | 4:00 p.m. | 2:45 pm | ||
| Thu., 5/11 | V Boys Golf | Holy Cross | Away - Western Hills [Directions] | 2:30 p.m. | Holy Cross 188 Kennedy 264 | 1:45pm | |
| Thu., 5/11 | V Boys Golf | Seymour | Away [Directions] | 3:45 p.m. | Seymour 218; Wilby 256 | 2:15 pm | |
| Thu., 5/11 | V Boys Tennis | Holy Cross | Home - Bucks Hill Park [Directions] | 3:00 p.m. | L 5-1 | 2:15 pm | |
| Thu., 5/11 | V Boys Tennis | Holy Cross | Away - Bucks Hill Park [Directions] | 4:15 p.m. | L 3-6 | 2:15 pm | |
| Thu., 5/11 | V Girls Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 3:00 p.m. | L 0-7 | 2:15 pm | |
| Thu., 5/11 | V Girls Tennis | Holy Cross | Home - Holy Cross [Directions] | 4:15 p.m. | L 0-7 | 2:15 pm | |
| Fri., 5/12 | V Baseball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 11-0 | ||
| Fri., 5/12 | V Softball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 0-24 | 2:15 pm | |
| Sat., 5/13 | V Baseball | Watertown | Away - Deland Field [Directions] | 8:30 a.m. | L 2-12 | 2:30 pm | |
| Mon., 5/15 | V Baseball | WCA | Home - Wilby H.S. [Directions] | 3:30 p.m. | L 6-10 | ||
| Mon., 5/15 | V Boys Golf | Wolcott | Away [Directions] | 3:30 p.m. | Wolcott 163; Wilby 253 | 2:15 pm | |
| Mon., 5/15 | V Softball | WCA | Home - Bucks Hill Park [Directions] | 3:30 p.m. | L 2-20 | 2:15 pm | |
| Mon., 5/15 | JV Softball | WCA | Home - Bucks Hill Park [Directions] | 3:30 p.m. | 2:15 pm | ||
| Tue., 5/16 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | 4:00 p.m. | L 3-23 | 2:15 pm | |
| Tue., 5/16 | V Boys Golf | Waterbury Coop, Woodland | Home - Western Hills [Directions] | Cancelled | Cancelled | 1:15 pm | |
| Tue., 5/16 | V Boys Golf | Woodland, Wilby | Home - Western Hills [Directions] | 2:30 p.m. | Woodland 188 Wilby 240 Kennedy 264 | 1:45pm | |
| Tue., 5/16 | V Boys Golf | Crosby | Home - Western Hills [Directions] | 2:30 p.m. | Kennedy 264 Cosby 280 | 1:45pm | |
| Tue., 5/16 | V Boys Outdoor Track | Wolcott, Derby | Away - Wolcott HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Tue., 5/16 | V Girls Outdoor Track | Wolcott, Derby | Away - Wolcott HS [Directions] | 3:30 p.m. | 2:30 pm | ||
| Tue., 5/16 | V Softball | Wolcott | Home - Bucks Hill Park [Directions] | 4:00 p.m. | L 0-20 | 2:30 pm | |
| Tue., 5/16 | JV Softball | Wolcott | Home - Bucks Hill Park [Directions] | 4:00 p.m. | 2:30 pm | ||
| Thu., 5/18 | V Baseball | Platt Tech | Home - Municipal Stadium [Directions] | 6:30 p.m. | L 2-12 | ||
| Thu., 5/18 | V Boys Golf | Waterbury Coop, Torrington | Home - Western Hills [Directions] | 2:30 p.m. | Wilby 240; Kennedy 247 | 1:15 pm | |
| Thu., 5/18 | V Boys Golf | Torrington, Wilby | Home - Western Hills [Directions] | 2:30 p.m. | Torrington 184 Wilby 240 Kennedy 247 | 1:45pm | |
| Thu., 5/18 | V Softball | Wolcott Tech | Home - Bucks Hill Park [Directions] | 3:00 p.m. | L 7-15 | 2:30 pm | |
| Fri., 5/19 | JV Baseball | Platt Tech | Away - Platt Tech baseball field [Directions] | Cancelled | Cancelled | 2:15 pm | |
| Fri., 5/19 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | 2:30 p.m. | Sacred Heart164 Kennedy 280 | 1:45pm | |
| Wed., 5/24 | V Boys Golf | Sacred Heart | Home - Western Hills [Directions] | 2:30 p.m. | Sacred Heart 177 Kennedy 269 | 1:45pm | |
| Wed., 5/24 | V Boys Golf | Naugatuck | Away [Directions] | 3:45 p.m. | 2:15 pm | ||