| Wilby 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 380 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Naugatuck | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Wolcott | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Sacred Heart | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Holy Cross | Away - Holy Cross HS [Directions] | TBA | 9:30 am | |
| TBA | JV Baseball | Crosby | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | 2:15 pm | |
| TBA | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | TBA | 9:15 am | |
| TBA | JV Baseball | Torrington | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Watertown | Away - Veterans Park [Directions] | TBA | 2:15 pm | |
| TBA | JV Baseball | Holy Cross | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Crosby | Away - Crosby HS [Directions] | TBA | 2:15 pm | |
| TBA | JV Baseball | Sacred Heart | Away - Fulton Park | TBA | 2:15 pm | |
| TBA | JV Baseball | WCA | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | TBA | ||
| TBA | FR Boys Basketball | Woodland | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| TBA | FR Boys Basketball | Watertown | Home - Reggie O'Brien Gymnasium [Directions] | TBA | ||
| TBA | FM Football | Oxford (Scrim.) | Away - OHS Football Field - West [Directions] | TBA | 2:30 pm | |
| TBA | FM Football | Holy Cross | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | V Boys Golf | Torrington, Waterbury Coop | Away - Western Hills [Directions] | 2:30 p.m. | 1:30 pm | |
| TBA | V Boys Golf | Torrington, Wilby | Home - Western Hills [Directions] | 2:30 p.m. | 2:00pm | |
| TBA | V Boys Golf | Waterbury Coop | Home - Western Hills [Directions] | Kennedy 288 Wilby 281 Medalist Anthony Daloia 65 | 1:30 pm | |
| TBA | V Boys Golf | Holy Cross | Home - Western Hills [Directions] | Kennedy 288 | 2:00pm | |
| TBA | V Boys Golf | Wilby | Away - Western Hills [Directions] | Wilby 281 Kennedy 288 | 2:00pm | |
| TBA | JV Boys Soccer | Ansonia | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| TBA | JV Boys Soccer | Crosby | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 2:15 pm | |
| TBA | JV Boys Soccer | Torrington | Away - Torrington HS [Directions] | TBA | 8:30 am | |
| TBA | JV Boys Soccer | Wolcott | Away - Wolcott HS, Lower Soccer Field [Directions] | TBA | 2:15 pm | |
| TBA | JV Boys Soccer | Sacred Heart | Away - Waterville Park | TBA | 2:15 pm | |
| TBA | JV Boys Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | TBA | 2:15 pm | |
| TBA | JV Boys Soccer | Watertown | Home - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | 3:00 pm | |
| TBA | JV Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 5:15 p.m. | 4:00 pm | |
| TBA | JV Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | TBA | No Bus | |
| TBA | JV Girls Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | TBA | No bus | |
| TBA | JV Softball | Sacred Heart | Away - Municipal Stadium - South Field | TBA | 2:30 pm | |
| TBA | JV Softball | Holy Cross | Home - Bucks Hill Park [Directions] | TBA | 2:45 pm | |
| TBA | JV Softball | WCA | Home - Bucks Hill Park [Directions] | TBA | ||
| TBA | JV Softball | Crosby | Away - Crosby HS Field #2 [Directions] | TBA | 2:30 pm | |
| TBA | JV Softball | Watertown | Away - Watertown HS [Directions] | TBA | 2:30 pm | |
| TBA | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | TBA | 2:30 pm | |
| TBA | JV Softball | Crosby | Home - Bucks Hill Park [Directions] | TBA | 2:45 pm | |
| TBA | JV Softball | WCA | Away - Huntingdon Park [Directions] | TBA | ||
| TBA | JV Softball | Kennedy | Away - Town Plot Park [Directions] | TBA | 2:30 pm | |
| Fri., 9/7 | V Boys Soccer | Crosby | Home - Wilby H.S. [Directions] | L 1-2 [Detailed Results] | ||
| Sat., 9/8 | V Football | Oxford | Home - Municipal Stadium [Directions] | L 0-42 | 8:15 am | 2 buses |
| Tue., 9/11 | V Boys Cross Country | Woodland, Wolcott | Away - Woodland HS Track [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 9/11 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 1-7 | 3:30 pm | |
| Tue., 9/11 | V Girls Cross Country | Woodland, Wolcott | Away - Woodland HS Track [Directions] | 3:30 p.m. | ||
| Tue., 9/11 | V Girls Volleyball | Torrington | Away - Torrington HS [Directions] | L 0-3 | 3:30 pm | |
| Tue., 9/11 | JV Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 4:45 p.m. | ||
| Wed., 9/12 | FM Football | Woodland | Home - Wilby H.S. [Directions] | 3:45 p.m. | ||
| Thu., 9/13 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | L 0-3 | 3:30 pm | |
| Thu., 9/13 | JV Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 4:45 p.m. | ||
| Fri., 9/14 | V Football | Woodland | Away - Woodland Football Field [Directions] | L 0-49 | 4:30 pm | 2 buses |
| Fri., 9/14 | V Boys Soccer | WCA | Home - Wilby H.S. [Directions] | L 4-5 | ||
| Fri., 9/14 | V Girls Swimming and Diving | Kennedy | Home - Wilby H.S. [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Girls Volleyball | Ansonia | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Fri., 9/14 | JV Girls Volleyball | Ansonia | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Sat., 9/15 | JV Boys Soccer | WCA | Home - Wilby H.S. [Directions] | 11:00 a.m. | ||
| Tue., 9/18 | V Boys Soccer | Holy Cross | Home - Municipal Stadium [Directions] | L 2-5 | ||
| Tue., 9/18 | V Girls Swimming and Diving | Torrington | Home - Wilby H.S. [Directions] | 4:00 p.m. | ||
| Tue., 9/18 | V Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | L 0-3 | 3:45 pm | |
| Tue., 9/18 | JV Girls Volleyball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Wed., 9/19 | V Boys Cross Country | Holy Cross, Kennedy, Torrington | Away - Holy Cross HS [Directions] | 4:00 p.m. | 2:15 pm | |
| Wed., 9/19 | FM Football | St. Paul Catholic | Home - Wilby H.S. [Directions] | 3:45 p.m. | ||
| Wed., 9/19 | JV Boys Soccer | Holy Cross | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Wed., 9/19 | V Girls Cross Country | Holy Cross, Kennedy, Torrington | Away - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Wed., 9/19 | V Girls Volleyball | Wolcott | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Wed., 9/19 | JV Girls Volleyball | Wolcott | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Fri., 9/21 | V Boys Soccer | Torrington | Away - Torrington HS [Directions] | L 1-2 | 5:00 pm | |
| Fri., 9/21 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 4:00 p.m. | 2:45 pm | |
| Fri., 9/21 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | L 0-3 | 2:45 pm | |
| Fri., 9/21 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/22 | V Football | Kennedy | Away - Municipal Stadium [Directions] | L 0-34 | 8:15 am | 2 buses |
| Mon., 9/24 | V Boys Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | T 1-1 | 4:45 pm | |
| Tue., 9/25 | V Girls Swimming and Diving | Oxford | Home - Wilby H.S. [Directions] | 4:00 p.m. | ||
| Tue., 9/25 | V Girls Volleyball | Kennedy | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Tue., 9/25 | JV Girls Volleyball | Kennedy | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Wed., 9/26 | JV Boys Soccer | Seymour | Away - Seymour HS Turf Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Thu., 9/27 | V Boys Cross Country | Naugatuck, Oxford, Sacred Heart | Away - Breen S (middle school) [Directions] | 3:30 p.m. | 2:15 pm | |
| Thu., 9/27 | V Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | W 2-1 | 4:45 pm | |
| Thu., 9/27 | V Girls Cross Country | Naugatuck, Oxford, Sacred Heart | Away - Breen S (middle school) [Directions] | 3:30 p.m. | ||
| Thu., 9/27 | V Girls Volleyball | Holy Cross | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Thu., 9/27 | JV Girls Volleyball | Holy Cross | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Fri., 9/28 | V Football | Crosby | Home - Municipal Stadium [Directions] | W 46-14 | 5:15 pm | 2 buses |
| Fri., 9/28 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 9/28 | V Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | L 0-3 | 2:45 pm | |
| Fri., 9/28 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Boys Cross Country | Seymour, Crosby, Watertown | Away - Seymour HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 10/2 | V Girls Cross Country | Seymour, Crosby, Watertown | Away - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Girls Swimming and Diving | Seymour | Home - Wilby H.S. [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Volleyball | Watertown | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Tue., 10/2 | JV Girls Volleyball | Watertown | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Wed., 10/3 | FM Football | Derby | Away [Directions] | Cancelled | 2:30 pm | |
| Wed., 10/3 | V Girls Volleyball | Plainville | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Wed., 10/3 | JV Girls Volleyball | Plainville | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Thu., 10/4 | FM Football | Sacred Heart | Away - Municipal Stadium | 3:30 p.m. | ||
| Fri., 10/5 | V Football | Derby | Home - Municipal Stadium [Directions] | L 0-24 | 5:15 pm | 2 buses |
| Fri., 10/5 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Wilby H.S. [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | Woodland | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Fri., 10/5 | JV Girls Volleyball | Woodland | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Tue., 10/9 | V Boys Cross Country | Derby, St. Paul Catholic, WCA | Away [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 10/9 | V Boys Soccer | Ansonia | Home - Wilby H.S. [Directions] | W 4-3 | ||
| Tue., 10/9 | V Girls Cross Country | Derby, St. Paul Catholic, WCA | Away [Directions] | 3:30 p.m. | ||
| Tue., 10/9 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 0-3 | 3:45 pm | |
| Tue., 10/9 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:45 p.m. | ||
| Thu., 10/11 | V Girls Volleyball | Naugatuck | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Thu., 10/11 | JV Girls Volleyball | Naugatuck | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Fri., 10/12 | V Boys Cross Country | City Meet | Away | 3:30 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Wilcox Tech | Home - Wilby H.S. [Directions] | L 1-3 | ||
| Fri., 10/12 | V Girls Cross Country | City Meet | Away | 3:30 p.m. | ||
| Fri., 10/12 | V Girls Swimming and Diving | Woodland | Home - Wilby H.S. [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Girls Volleyball | Crosby | Home - Wilby H.S. [Directions] | W 3-2 | ||
| Fri., 10/12 | JV Girls Volleyball | Crosby | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Sat., 10/13 | JV Boys Soccer | Wilcox Tech | Home - Wilby H.S. [Directions] | 11:00 a.m. | ||
| Tue., 10/16 | V Boys Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | L 1-3 | 2:15 pm | |
| Tue., 10/16 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/16 | V Girls Volleyball | WCA | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Tue., 10/16 | JV Girls Volleyball | WCA | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Wed., 10/17 | V Boys Cross Country | NVL Championship | Away | TBA | tba | |
| Wed., 10/17 | V Boys Soccer | Kennedy | Home - Wilby H.S. [Directions] | L 1-2 | ||
| Wed., 10/17 | V Girls Cross Country | NVL Championship | Away | TBA | ||
| Thu., 10/18 | FM Football | Torrington | Away - Torrington [Directions] | 3:30 p.m. | 2:30 pm | |
| Thu., 10/18 | V Girls Volleyball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | L 1-3 | 2:45 pm | |
| Thu., 10/18 | JV Girls Volleyball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 10/19 | V Boys Soccer | Naugatuck | Home - Wilby H.S. [Directions] | L 0-3 | ||
| Fri., 10/19 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | L 0-3 | 2:30 pm | |
| Fri., 10/19 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Sat., 10/20 | V Football | Torrington | Home - Municipal Stadium [Directions] | L 0-46 | 8:15 am | 2 buses |
| Sat., 10/20 | JV Boys Soccer | Naugatuck | Home - Wilby H.S. [Directions] | 11:00 a.m. | ||
| Mon., 10/22 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | W 5-1 | 2:15 pm | |
| Tue., 10/23 | V Boys Soccer | Sacred Heart | Away - Crosby HS - turf field | L 1-2 | 2:30 pm | |
| Wed., 10/24 | V Boys Soccer | Watertown | Home - Municipal Stadium [Directions] | L 0-2 | ||
| Wed., 10/24 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 0-3 | 3:30 pm | |
| Wed., 10/24 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | ||
| Thu., 10/25 | V Boys Soccer | O'Brien Tech | Away - O'Brien Tech Athletic Complex [Directions] | L 2-6 | 2:15 pm | |
| Fri., 10/26 | V Football | Holy Cross | Away - Holy Cross HS [Directions] | L 6-44 | 11:15 am | 2 buses |
| Tue., 10/30 | V Girls Swimming and Diving | NVL Trials | Away - Kennedy HS | TBA | tba | |
| Wed., 10/31 | FM Football | Seymour | Away [Directions] | 3:45 p.m. | 2:30 pm | |
| Thu., 11/1 | V Girls Swimming and Diving | NVL Diving Championship | Away - Kennedy HS | TBA | tba | |
| Fri., 11/2 | V Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | L 12-14 | 5:00 pm | 2 buses |
| Fri., 11/2 | V Girls Swimming and Diving | NVL Swim Finals | Away - Kennedy HS | TBA | tba | |
| Thu., 11/8 | V Football | WCA | Home - Municipal Stadium [Directions] | L 13-34 | 4:15 pm | 2 buses |
| Wed., 11/21 | V Football | Sacred Heart | Away - Municipal Stadium | L 6-32 | 4:15 pm | 2 buses |
| Tue., 12/11 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | L 17-51 | 4:00 pm | |
| Tue., 12/11 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | 4:00 pm | |
| Fri., 12/14 | V Boys Indoor Track | 17th Annual Hillhouse Track and Field Invitational Day1 | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 pm | |
| Fri., 12/14 | V Girls Basketball | Kaynor Tech | Home - Reggie O'Brien Gymnasium [Directions] | W 41-40 | ||
| Fri., 12/14 | JV Girls Basketball | Kaynor Tech | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | V Girls Indoor Track | 17th Annual Hillhouse Track and Field Invitational Day 1 | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 pm | |
| Sat., 12/15 | V Boys Indoor Track | 17th Annual Hillhouse Track and Field Invitational Day 2 | Away - Flyod Little Athletic Center | 10:00 a.m. | 8:15 am | |
| Sat., 12/15 | V Girls Indoor Track | 17th Annual Hillhouse Track and Field Invitational Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:15 am | |
| Tue., 12/18 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | L 58-62 | 4:15 pm | |
| Tue., 12/18 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | ||
| Tue., 12/18 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 12/18 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:00 p.m. | 3:30 pm | |
| Tue., 12/18 | V Girls Basketball | Wolcott | Home - Reggie O'Brien Gymnasium [Directions] | L 20-49 | ||
| Tue., 12/18 | JV Girls Basketball | Wolcott | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/20 | V Boys Basketball | Ansonia | Home - Reggie O'Brien Gymnasium [Directions] | W 58-54 | ||
| Thu., 12/20 | JV Boys Basketball | Ansonia | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/20 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | L 22-56 | 4:45 pm | |
| Sat., 12/22 | V Boys Indoor Track | Hillhouse Qualifier | Away - Flyod Little Athletic Center | 10:00 a.m. | 8:15 am | |
| Sat., 12/22 | V Girls Indoor Track | Hillhouse Qualifier | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:15 am | |
| Wed., 12/26 | FR Boys Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 12/27 | V Boys Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | L 46-84 | ||
| Thu., 12/27 | JV Boys Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away - Floyd Little Athletic Center | 12:00 p.m. | 10:15 am | |
| Thu., 12/27 | V Girls Indoor Track | Jack Long Invitational | Away - Floyd Little Athletic Center | 12:00 p.m. | 10:15 am | |
| Wed., 1/2 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | L 47-63 | 4:15 pm | |
| Wed., 1/2 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | ||
| Wed., 1/2 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 1/2 | V Girls Basketball | Naugatuck | Home - Reggie O'Brien Gymnasium [Directions] | L 24-62 | ||
| Wed., 1/2 | JV Girls Basketball | Naugatuck | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/4 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | L 37-85 | No Bus | |
| Fri., 1/4 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 1/4 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 1/4 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 5:00 p.m. | 2:30 pm | |
| Fri., 1/4 | V Girls Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | L 19-66 | ||
| Fri., 1/4 | JV Girls Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 1/5 | V Boys Indoor Track | 5th Elm City Coaches Meet | Away - Floyd Little Athletc Center | 10:00 a.m. | 8:15 am | |
| Sat., 1/5 | V Girls Indoor Track | 5th Elm City Coaches Meet | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:15 am | |
| Mon., 1/7 | FR Boys Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 1/8 | V Boys Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | L 58-79 | ||
| Tue., 1/8 | JV Boys Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/8 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 24-51 | No Bus | |
| Tue., 1/8 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | No Bus | |
| Wed., 1/9 | V Boys Swimming and Diving | Torrington | Home - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 6:30 p.m. | No Bus | |
| Fri., 1/11 | V Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | L 42-82 | No Bus | |
| Fri., 1/11 | JV Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | ||
| Fri., 1/11 | V Boys Swimming and Diving | Naugatuck | Home - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Fri., 1/11 | V Girls Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | L 21-52 | ||
| Fri., 1/11 | JV Girls Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | V Boys Basketball | Nonnewaug | Home - Reggie O'Brien Gymnasium [Directions] | L 42=53(OT) | ||
| Mon., 1/14 | JV Boys Basketball | Nonnewaug | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | L 26-50 | 4:30 pm | |
| Tue., 1/15 | FR Boys Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 1/15 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 5:00 p.m. | 2:30 pm | |
| Wed., 1/16 | V Boys Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | L 41-93 | ||
| Wed., 1/16 | JV Boys Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/16 | V Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | L 27-73 | No Bus | |
| Fri., 1/18 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | L 43-70 | 3:15 pm | |
| Fri., 1/18 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/18 | V Girls Basketball | Oxford | Home - Reggie O'Brien Gymnasium [Directions] | L 32-62 | ||
| Sat., 1/19 | V Boys Indoor Track | SCC Coaches Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 7:30 am | |
| Sat., 1/19 | V Girls Indoor Track | SCC Coaches Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 7:30 am | |
| Wed., 1/23 | V Boys Basketball | Derby | Home - Reggie O'Brien Gymnasium [Directions] | L 49-79 | ||
| Wed., 1/23 | JV Boys Basketball | Derby | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/23 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | L 19-36 | 4:15 pm | |
| Wed., 1/23 | JV Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:30 p.m. | 4:15 pm | |
| Thu., 1/24 | FR Boys Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 1/25 | V Boys Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | L 34-76 | ||
| Fri., 1/25 | JV Boys Basketball | Holy Cross | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | V Boys Swimming and Diving | Woodland | Home - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | L 12-66 | No Bus | |
| Fri., 1/25 | JV Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | No Bus | |
| Mon., 1/28 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | No Bus | |
| Mon., 1/28 | V Boys Indoor Track | NVL Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 pm | |
| Mon., 1/28 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | L 17-71 | No Bus | |
| Mon., 1/28 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 4:30 p.m. | No Bus | |
| Mon., 1/28 | V Girls Indoor Track | NVL Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 pm | |
| Thu., 1/31 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 64-83 | No Bus | |
| Fri., 2/1 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | L 35-85 | No Bus | |
| Fri., 2/1 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Fri., 2/1 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 3:30 p.m. | 2:15 pm | |
| Fri., 2/1 | V Boys Swimming and Diving | Seymour | Home - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Sacred Heart | Home - Reggie O'Brien Gymnasium [Directions] | L 33-93 | ||
| Mon., 2/4 | V Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | L 63-107 | No Bus | |
| Mon., 2/4 | JV Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Mon., 2/4 | V Girls Basketball | Crosby | Home - Reggie O'Brien Gymnasium [Directions] | L 19-73 | ||
| Tue., 2/5 | FR Boys Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | No Bus | |
| Tue., 2/5 | V Boys Swimming and Diving | Oxford | Home - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Wed., 2/6 | V Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | L 58-68 | No Bus | |
| Wed., 2/6 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/6 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 4:00 p.m. | 3:00 pm | |
| Wed., 2/6 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | L 16-51 | 4:00 pm | |
| Wed., 2/6 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | Cancelled | 4:00 pm | |
| Thu., 2/7 | FR Boys Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 2/7 | V Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | L 13-71 | No bus | |
| Fri., 2/8 | V Boys Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | L 56-89 | ||
| Fri., 2/8 | JV Boys Basketball | WCA | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 2:15 pm | |
| Fri., 2/8 | V Boys Swimming and Diving | Enfield/Ellington/Suffield | Home - Wilby H.S. [Directions] | 5:00 p.m. | ||
| Fri., 2/8 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 2:15 pm | |
| Sat., 2/9 | V Girls Basketball | Kennedy | Home - Reggie O'Brien Gymnasium [Directions] | L 36-62 | ||
| Mon., 2/11 | V Boys Basketball | Woodland | Home - Reggie O'Brien Gymnasium [Directions] | L 65-71(OT) | ||
| Mon., 2/11 | JV Boys Basketball | Woodland | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | V Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | L 18-50 | 4:00 pm | |
| Thu., 2/14 | V Boys Basketball | Watertown | Home - Reggie O'Brien Gymnasium [Directions] | W 74-66 | ||
| Thu., 2/14 | JV Boys Basketball | Watertown | Home - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/14 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | 5:45 pm | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | TDA | |
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | TBA | |
| Tue., 2/19 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 40-74 | 4:00 pm | |
| Tue., 2/19 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Tue., 2/19 | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 2/22 | V Boys Swimming and Diving | Crosby/WCA, Danbury | Home - Wilby H.S. [Directions] | 5:00 p.m. | ||
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | TBA | |
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | TBA | |
| Mon., 3/25 | V Baseball | Nonnewaug (Scrim.) | Away - Nonnewaug Varsity Baseball Field [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 3/27 | V Baseball | WCA (Scrim.) | Home - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Baseball | Naugatuck | Home - Wilby H.S. [Directions] | L 0-29 | ||
| Tue., 4/2 | V Boys Outdoor Track | Seymour, WCA | Away - Seymour HS Turf Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 4/2 | V Girls Outdoor Track | Seymour, WCA | Away - Seymour HS Turf Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 4/2 | V Softball | Naugatuck | Home - Bucks Hill Park [Directions] | L 0-16 | 2:45 pm | |
| Wed., 4/3 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | L 0-5 | 2:15 pm | |
| Wed., 4/3 | JV Softball | Naugatuck | Home - Bucks Hill Park [Directions] | 3:45 p.m. | 2:45 pm | |
| Wed., 4/3 | V Girls Tennis | Naugatuck | Home - Wilby H.S. [Directions] | L 0-7 | ||
| Thu., 4/4 | V Boys Tennis | Woodland | Home - Wilby H.S. [Directions] | L 0-5 | ||
| Thu., 4/4 | V Girls Tennis | Woodland | Away - Woodland HS Tennis courts [Directions] | L 0-7 | 2:15 pm | |
| Fri., 4/5 | V Baseball | Seymour | Away - French Park [Directions] | L 0-10 | 2:15 pm | |
| Mon., 4/8 | V Baseball | Kaynor Tech | Home - Wilby H.S. [Directions] | W 7-6 | ||
| Mon., 4/8 | V Softball | Woodland | Home - Bucks Hill Park [Directions] | L 2-22 | 2:45 pm | |
| Tue., 4/9 | V Boys Outdoor Track | Torrington, Crosby | Away - Torrington HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 4/9 | V Girls Outdoor Track | Torrington, Crosby | Away - Torrington HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 4/9 | JV Softball | Woodland | Home - Bucks Hill Park [Directions] | 3:45 p.m. | 2:45 pm | |
| Wed., 4/10 | V Baseball | Wolcott | Home - Wilby H.S. [Directions] | L 0-22 | ||
| Wed., 4/10 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | Sacred Heart 204 Wilby 252 Medalist Shea Zaccagnini 39 | 1:30 pm | |
| Wed., 4/10 | V Boys Tennis | Holy Cross | Home - Wilby H.S. [Directions] | L 1-4 | ||
| Wed., 4/10 | V Softball | Wolcott | Away - George Babcock Field, Wolcott HS [Directions] | L 0-17 | 2:30 pm | |
| Wed., 4/10 | V Girls Tennis | Holy Cross | Away - Holy Cross HS [Directions] | L 0-7 | 2:15 pm | |
| Thu., 4/11 | V Boys Golf | Woodland | Home - Western Hills [Directions] | Woodland 247 Wilby 264 Medalist Tom Conroy 52 | 1:30 pm | |
| Fri., 4/12 | V Baseball | Sacred Heart | Home - Wilby H.S. [Directions] | L 4-16 | ||
| Fri., 4/12 | V Boys Outdoor Track | Naugatuck, Kennedy | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 4/12 | V Girls Outdoor Track | Naugatuck, Kennedy | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 4/12 | V Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | L 8-23 | 2:30 pm | |
| Tue., 4/16 | V Baseball | Holy Cross | Home - Wilby HS [Directions] | L 0-15 | 9:30 am | |
| Tue., 4/16 | V Boys Tennis | Crosby | Home - Wilby H.S. [Directions] | L 1-2 | 2:15 pm | |
| Tue., 4/16 | V Boys Tennis | Crosby | Home - Wilby H.S. [Directions] | L 1-2 | ||
| Tue., 4/16 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | L 0-7 | 2:15 pm | |
| Wed., 4/17 | V Baseball | WCA | Away - Washington Park [Directions] | L 0-10 | 8:45 am | |
| Wed., 4/17 | V Softball | WCA | Home - Bucks Hill Park [Directions] | L 22-25 | 2:45 pm | |
| Wed., 4/17 | V Girls Tennis | Seymour | Away - Seymour HS [Directions] | L 0-7 | 2:15 pm | |
| Thu., 4/18 | V Baseball | Crosby | Home - Municipal Stadium [Directions] | L 13-14 | ||
| Thu., 4/18 | V Boys Tennis | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 1-4 | 8:45 am | |
| Thu., 4/18 | V Softball | Crosby | Away - Crosby HS Field #1 [Directions] | L 20-23 | 2:30 pm | |
| Fri., 4/19 | V Boys Tennis | Torrington | Home - Wilby H.S. [Directions] | L 0-5 | ||
| Mon., 4/22 | V Boys Golf | Wolcott | Home - Western Hills [Directions] | Wolcott 208 Wilby 278 Medalist Jared Dunn 48 | 1:30 pm | |
| Mon., 4/22 | V Boys Golf | Wolcott | Home - Western Hills [Directions] | Wolcott 208 Kennedy 280 | 2:00pm | |
| Tue., 4/23 | V Boys Outdoor Track | Holy Cross, Watertown | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 4/23 | V Girls Outdoor Track | Holy Cross, Watertown | Away - Holy Cross HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 4/23 | JV Softball | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | 2:30 pm | |
| Tue., 4/23 | V Girls Tennis | Torrington | Away - Torrington HS [Directions] | L 0-7 | 2:15 pm | |
| Wed., 4/24 | V Baseball | Kennedy | Away - Waterville Park [Directions] | L 1-14 | 2:15 pm | |
| Wed., 4/24 | V Boys Golf | St. Paul Catholic | Away [Directions] | St Paul 138 Wilby 241 Medalist Michael Dolce 30 | 1:30 pm | |
| Wed., 4/24 | V Boys Golf | St. Paul Catholic | Away [Directions] | 138 St. Paul Kennedy 237 Wilby 241 | 2:00pm | |
| Wed., 4/24 | V Boys Tennis | Watertown | Away - Crestbrook Park [Directions] | L 0-5 | 2:15 pm | |
| Wed., 4/24 | V Softball | Kennedy | Home - Bucks Hill Park [Directions] | L 1-20 | 2:45 pm | |
| Wed., 4/24 | V Girls Tennis | Watertown | Home - Wilby H.S. [Directions] | L 0-7 | ||
| Thu., 4/25 | V Boys Golf | Seymour | Away - Oxford Greens [Directions] | Seymour 186 Wilby 270 Medalist Cody Guillette | 1:30 pm | |
| Thu., 4/25 | V Boys Golf | Seymour | Away - Oxford Greens [Directions] | Seymour 186 Wilby 270 Kennedy 280 | 2:00pm | |
| Thu., 4/25 | V Boys Tennis | Sacred Heart | Home - Wilby H.S. [Directions] | L 1-4 | ||
| Thu., 4/25 | V Boys Tennis | Sacred Heart | Home - Wilby H.S. [Directions] | L 1-4 | 2:15 pm | |
| Thu., 4/25 | V Softball | Ansonia | Away - Ansonia HS [Directions] | L 6-12 | 2:30 pm | |
| Thu., 4/25 | V Girls Tennis | Sacred Heart | Away - Fulton Park | L 0-7 | 2:15 pm | |
| Thu., 4/25 | V Girls Tennis | Sacred Heart | Away - Fulton Park | L 0-7 | ||
| Sat., 4/27 | V Baseball | Ansonia | Home - Waterville Park [Directions] | L 3-14 | ||
| Mon., 4/29 | V Baseball | Torrington | Home - Wilby H.S. [Directions] | L 1-16 | ||
| Mon., 4/29 | V Boys Golf | Watertown | Away [Directions] | 2:30 p.m. | 1:30 pm | |
| Mon., 4/29 | V Boys Golf | Watertown | Away [Directions] | forfeit | 2:00pm | |
| Mon., 4/29 | V Boys Tennis | Holy Cross | Away - Holy Cross HS [Directions] | L 1-4 | 2:15 pm | |
| Mon., 4/29 | V Softball | Torrington | Away - Torrington HS [Directions] | L 0-15 | 2:30 pm | |
| Mon., 4/29 | V Girls Tennis | Holy Cross | Home - Wilby H.S. [Directions] | L 0-7 | ||
| Tue., 4/30 | V Boys Outdoor Track | Wolcott, Sacred Heart | Away - Wolcott HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 4/30 | V Girls Outdoor Track | Wolcott, Sacred Heart | Away [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 5/1 | V Baseball | Watertown | Away - Deland Field [Directions] | L 2-12 | 2:15 pm | |
| Wed., 5/1 | V Boys Golf | Naugatuck, Waterbury Coop | Away - Western Hills [Directions] | Naugatuck 221 Kennedy 288 Wilby 281 Medalist Joe Macary 51 | 1:30 pm | |
| Wed., 5/1 | V Boys Golf | Naugatuck, Wilby | Home - Western Hills [Directions] | Naugatuck 221 Wilby 281 Kennedy 288 | 2:00pm | |
| Wed., 5/1 | V Softball | Watertown | Away - Watertown HS [Directions] | L 0-22 | 2:30 pm | |
| Wed., 5/1 | V Girls Tennis | Crosby | Away - Crosby HS [Directions] | L 0-7 | 2:15 pm | |
| Wed., 5/1 | V Girls Tennis | Crosby | Home - Crosby HS [Directions] | L 0-7 | ||
| Thu., 5/2 | V Softball | Derby | Home - Bucks Hill Park [Directions] | L 3-18 | 2:45 pm | |
| Fri., 5/3 | V Softball | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | L 0-23 | 2:30 pm | |
| Fri., 5/3 | V Softball | Holy Cross | Home - Municipal Stadium (Wtby) [Directions] | L 0-19 | 2:45 pm | |
| Sat., 5/4 | V Baseball | Derby | Away - Waterville Park, Waterbury [Directions] | L 0-18 | 2:15 pm | |
| Mon., 5/6 | V Baseball | Crosby | Away - Wilby HS [Directions] | L 3-4 | 2:15 pm | |
| Mon., 5/6 | V Boys Golf | Kaynor Tech | Home - Western Hills [Directions] | 2:30 p.m. | 1:30 pm | |
| Mon., 5/6 | V Boys Tennis | Kennedy | Home - Wilby H.S. [Directions] | L 1-4 | ||
| Mon., 5/6 | V Softball | Crosby | Home - Bucks Hill Park [Directions] | L 11-30 | 2:45 pm | |
| Mon., 5/6 | V Girls Tennis | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | L 1-6 | 2:15 pm | |
| Mon., 5/6 | V Girls Tennis | Kennedy | Away - Kennedy [Directions] | L 0-7 | ||
| Tue., 5/7 | V Baseball | Holy Cross | Away - Holy Cross HS [Directions] | L 0-18 | ||
| Tue., 5/7 | V Boys Golf | Holy Cross | Away - Western Hills [Directions] | Holy Cross 162 Wilby 267 Medalist Vin Craziano 39 | 1:30 pm | |
| Tue., 5/7 | V Boys Outdoor Track | Woodland, Derby | Away - Woodland HS Track [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 5/7 | V Girls Outdoor Track | Woodland, Derby | Away - Woodland HS Track [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 5/8 | V Baseball | Sacred Heart | Away - Municipal Stadium | L 1-11 | 4:30 pm | |
| Wed., 5/8 | V Boys Tennis | Torrington | Away - Torrington HS [Directions] | L 0-5 | 2:15 pm | |
| Wed., 5/8 | V Softball | Sacred Heart | Home - Bucks Hill Park [Directions] | L 1-14 | 2:45 pm | |
| Wed., 5/8 | V Girls Tennis | St. Paul Catholic | Home - Wilby H.S. [Directions] | L 0-7 | ||
| Thu., 5/9 | V Baseball | WCA | Home - Wilby H.S. [Directions] | L 2-14 | ||
| Thu., 5/9 | V Boys Golf | Woodland | Away [Directions] | Woodland 228 Wilby 265 Medalist Tom Conroy 48 | 1:30 pm | |
| Thu., 5/9 | V Boys Golf | Woodland | Away [Directions] | Kennedy 285 | 2:00pm | |
| Thu., 5/9 | V Boys Tennis | Wolcott | Away - Wolcott HS [Directions] | L 1-4 | ||
| Thu., 5/9 | V Boys Tennis | Wolcott | Away - Wolcott HS [Directions] | L 1-4 | 2:15 pm | |
| Thu., 5/9 | V Softball | WCA | Away - Huntingdon Park [Directions] | L 1-17 | 2:30 pm | |
| Thu., 5/9 | JV Softball | Sacred Heart | Home - Bucks Hill Park [Directions] | 3:45 p.m. | 2:45 pm | |
| Thu., 5/9 | V Girls Tennis | Wolcott | Home - Wilby H.S. [Directions] | L 0-7 | ||
| Tue., 5/14 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | Kennedy 285 | 2:00pm | |
| Tue., 5/14 | V Softball | Oxford | Home - Municipal Stadium [Directions] | L 2-20 | 2:45 pm | |
| Wed., 5/15 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | L 0-10 | 2:15 pm | |
| Wed., 5/15 | V Softball | Kaynor Tech | Away - Kaynor Tech Softball Field [Directions] | L 5-18 | 2:45 pm | |
| Wed., 5/15 | V Softball | Kennedy | Away - Municipal Stadium [Directions] | L 3-16 | 2:30 pm | |
| Thu., 5/16 | V Baseball | Platt Tech | Home - Municipal Stadium [Directions] | L 1-3 | ||
| Thu., 5/16 | V Boys Golf | Woodland | Home - Western Hills [Directions] | Kennedy 285 | 2:00pm | |
| Thu., 5/16 | JV Softball | Kennedy | Home - Bucks Hill Park [Directions] | 3:45 p.m. | 2:45 pm | |
| Fri., 5/17 | JV Baseball | Platt Tech | Home - Wilby H.S. [Directions] | Cancelled | ||
| Mon., 5/20 | V Baseball | Kennedy | Home - Waterville Park [Directions] | L 1-12 | ||
| Mon., 5/20 | V Boys Golf | Holy Cross, Waterbury Coop | Away - Western Hills [Directions] | Holy Cross 161 Wilby 284 Kennedy 288 Medalist HC Nate Gettleman | 1:30 pm | |
| Mon., 5/20 | V Boys Golf | Holy Cross, Wilby | Away - Western Hills [Directions] | 288Kennedy | 2:00pm | |
| Tue., 5/21 | V Boys Outdoor Track | NVL Championship | Away | TBA | ||
| Tue., 5/21 | V Girls Outdoor Track | NVL Championship | Away | TBA | 2:15 pm | |
| Wed., 5/22 | V Boys Golf | Sacred Heart | Home - Western Hills [Directions] | Sacred Heart 218 Wilby 270 Medalist Shea Zaccagnili 44 | 1:30 pm | |
| Wed., 5/22 | V Boys Golf | Sacred Heart | Home - Western Hills [Directions] | 288 Kennedy | 2:00pm | |
| Tue., 5/28 | V Boys Golf | City Championship | Away | 2:30 p.m. | TBA | |
| Thu., 5/30 | V Boys Golf | NVL Championship | Away - Watertown Golf Club | 8:30 a.m. | 7:30 am | |