| Crosby 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 358 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Wilby | Away - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Wilby | Home - Crosby HS [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | ||
| TBA | JV Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 10:00 a.m. | ||
| TBA | JV Football | Ansonia | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 11:00 a.m. | ||
| TBA | FR Football | Watertown | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | Cancelled | Cancelled | |
| TBA | V Boys Golf | Torrington, Wilby | Home - Western Hills [Directions] | 2:30 p.m. | ||
| TBA | V Boys Golf | Holy Cross | Home - Western Hills [Directions] | TBA | Kennedy 288 | |
| TBA | V Boys Golf | Wilby | Away - Western Hills [Directions] | TBA | Wilby 281 Kennedy 288 | |
| TBA | JV Boys Soccer | Ansonia | Home - Crosby HS - grass soccer field [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Torrington | Home - Crosby HS - grass soccer field [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | TBA | ||
| TBA | JV Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| TBA | JV Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Girls Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Basketball | WCA | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Sacred Heart | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | TBA | ||
| TBA | JV Girls Basketball | Seymour | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Wilby | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | TBA | ||
| TBA | JV Girls Basketball | Holy Cross | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Brookfield | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | TBA | ||
| TBA | JV Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Basketball | Kennedy | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Watertown | Home - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Softball | Oxford | Away - OHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Wolcott | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Holy Cross | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Kennedy | Away - Town Plot Park [Directions] | TBA | ||
| TBA | JV Softball | Wilby | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Sacred Heart | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Naugatuck | Away - Breen SS (JV & Fr.) [Directions] | TBA | ||
| TBA | JV Softball | WCA | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Wilby | Away - Bucks Hill Park [Directions] | TBA | ||
| TBA | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | TBA | ||
| TBA | JV Softball | Kennedy | Home - Crosby HS Field #2 [Directions] | TBA | ||
| TBA | JV Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | TBA | ||
| Fri., 9/7 | FR Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Fri., 9/7 | V Boys Soccer | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | W 2-1 | |
| Sat., 9/8 | V Football | Holy Cross | Away - Holy Cross HS [Directions] | 1:00 p.m. | L 0-58 | |
| Tue., 9/11 | V Boys Cross Country | Derby, Naugatuck, Holy Cross | Away - Breen S (middle school) [Directions] | 3:30 p.m. | Naugy home | |
| Tue., 9/11 | V Boys Soccer | Sacred Heart | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 9/11 | V Girls Cross Country | Derby, Naugatuck, Holy Cross | Away - Breen S (middle school) [Directions] | 3:30 p.m. | Naugy home | |
| Tue., 9/11 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 9/11 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | ||
| Wed., 9/12 | FR Football | Naugatuck | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Thu., 9/13 | JV Boys Soccer | Sacred Heart | Away - Waterville Park | 3:45 p.m. | ||
| Thu., 9/13 | V Girls Volleyball | Holy Cross | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/13 | JV Girls Volleyball | Holy Cross | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Fri., 9/14 | V Football | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 0-54 | |
| Fri., 9/14 | V Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | L 3-0 | |
| Fri., 9/14 | V Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/14 | JV Girls Volleyball | Seymour | Away - Seymour HS [Directions] | 4:45 p.m. | ||
| Sat., 9/15 | JV Football | Naugatuck | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | Cancelled | Cancelled | |
| Sat., 9/15 | JV Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 10:30 a.m. | ||
| Tue., 9/18 | V Boys Cross Country | St. Paul Catholic, Sacred Heart, Wolcott | Away - Montoe Park [Directions] | 3:30 p.m. | Wolcott home | |
| Tue., 9/18 | V Boys Soccer | Kennedy | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 6:00 p.m. | L 2-1 | |
| Tue., 9/18 | V Girls Volleyball | Wilby | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/18 | JV Girls Volleyball | Wilby | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Wed., 9/19 | FR Football | Wolcott | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Wed., 9/19 | JV Boys Soccer | Kennedy | Home - Crosby HS - grass soccer field [Directions] | 3:45 p.m. | ||
| Wed., 9/19 | V Girls Cross Country | St. Paul Catholic, Sacred Heart, Wolcott | Away - Montoe Park [Directions] | 3:30 p.m. | Wolcott home | |
| Thu., 9/20 | V Boys Soccer | Ansonia | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 9/21 | V Football | WCA | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 7:00 p.m. | L 12-52 | |
| Fri., 9/21 | V Boys Soccer | Bassick | Away - Went Field [Directions] | 3:45 p.m. | L 2-1 | |
| Fri., 9/21 | V Girls Volleyball | Woodland | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/21 | JV Girls Volleyball | Woodland | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Sat., 9/22 | JV Football | Wolcott | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | Cancelled | Cancelled | |
| Tue., 9/25 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/25 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:45 p.m. | ||
| Wed., 9/26 | V Boys Soccer | Torrington | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 6:30 p.m. | L 2-0 | |
| Thu., 9/27 | V Boys Cross Country | Kennedy, WCA | Home - Montoe Park [Directions] | 3:45 p.m. | ||
| Thu., 9/27 | V Girls Cross Country | Kennedy, WCA | Home - Montoe Park [Directions] | 3:45 p.m. | ||
| Thu., 9/27 | V Girls Volleyball | Torrington | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/27 | JV Girls Volleyball | Torrington | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Fri., 9/28 | V Football | Wilby | Away - Municipal Stadium [Directions] | 7:00 p.m. | L 14-46 | |
| Fri., 9/28 | V Boys Soccer | Holy Cross | Away - Crosby HS [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/28 | V Girls Volleyball | St. Paul Catholic | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/28 | JV Girls Volleyball | St. Paul Catholic | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Sat., 9/29 | JV Football | Wolcott | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 11:00 a.m. | ||
| Sat., 9/29 | JV Boys Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 11:00 a.m. | ||
| Tue., 10/2 | V Boys Cross Country | Watertown, Seymour, Wilby | Away - Seymour HS [Directions] | 3:45 p.m. | Seymour home | |
| Tue., 10/2 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 10/2 | V Girls Cross Country | Watertown, Seymour, Wilby | Away - Seymour HS [Directions] | 3:45 p.m. | Seymour home | |
| Tue., 10/2 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/2 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 4:45 p.m. | ||
| Wed., 10/3 | FR Football | Kennedy | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Fri., 10/5 | V Football | Sacred Heart | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 7:00 p.m. | L 12-44 | |
| Fri., 10/5 | V Boys Soccer | Seymour | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:45 p.m. | W 3-0 | out-of-league game |
| Fri., 10/5 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/5 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 4:30 p.m. | ||
| Sat., 10/6 | JV Boys Soccer | Seymour | Home - Crosby HS - grass soccer field [Directions] | 11:00 a.m. | out-of-league game | |
| Tue., 10/9 | V Boys Cross Country | Oxford, Torrington, Woodland | Away - Woodland HS Track [Directions] | 3:30 p.m. | Woodland home | |
| Tue., 10/9 | V Boys Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 10/9 | V Girls Cross Country | Oxford, Torrington, Woodland | Away - Woodland HS Track [Directions] | 3:30 p.m. | Woodland home | |
| Tue., 10/9 | V Girls Volleyball | WCA | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/9 | JV Girls Volleyball | WCA | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Wed., 10/10 | JV Boys Soccer | Wolcott | Away - Wolcott HS, Lower Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/11 | V Girls Volleyball | Wolcott | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 10/11 | JV Girls Volleyball | Wolcott | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Fri., 10/12 | V Boys Cross Country | City Championships | Away - Montoe Park | 3:45 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Naugatuck | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:45 p.m. | L 4-0 | |
| Fri., 10/12 | V Girls Cross Country | City Championships | Away - Montoe Park | 3:45 p.m. | ||
| Fri., 10/12 | V Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 4:30 p.m. | L 2-3 | |
| Fri., 10/12 | JV Girls Volleyball | Wilby | Away - Wilby H.S. [Directions] | 3:30 p.m. | ||
| Sat., 10/13 | JV Boys Soccer | Naugatuck | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 11:00 a.m. | ||
| Mon., 10/15 | V Girls Volleyball | Whitney Tech | Away - Whitney Tech School Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Mon., 10/15 | JV Girls Volleyball | Whitney Tech | Away - Whitney Tech School Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 10/16 | V Boys Soccer | Watertown | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 6:00 p.m. | T 2-2 | |
| Tue., 10/16 | V Girls Volleyball | Whitney Tech | Home - Augelli Court -- Crosby HS [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/16 | JV Girls Volleyball | Whitney Tech | Home - Augelli Court -- Crosby HS [Directions] | 3:45 p.m. | ||
| Wed., 10/17 | V Boys Cross Country | NVL Championships | Away - Veterans' Park | 3:45 p.m. | ||
| Wed., 10/17 | FR Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | ||
| Wed., 10/17 | JV Boys Soccer | Watertown | Home - Crosby HS - grass soccer field [Directions] | 3:45 p.m. | ||
| Wed., 10/17 | V Girls Cross Country | NVL Championships | Away - Veterans' Park | 3:45 p.m. | ||
| Wed., 10/17 | V Girls Volleyball | Watertown | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/17 | JV Girls Volleyball | Watertown | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 10/19 | V Football | St. Paul Catholic | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 7:00 p.m. | L 0-28 | |
| Fri., 10/19 | V Girls Volleyball | Kennedy | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/19 | JV Girls Volleyball | Kennedy | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Sat., 10/20 | JV Boys Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | 11:00 a.m. | ||
| Mon., 10/22 | V Boys Soccer | WCA | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/22 | JV Boys Soccer | WCA | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:45 p.m. | ||
| Mon., 10/22 | V Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 10/22 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 3:45 p.m. | ||
| Tue., 10/23 | V Girls Volleyball | Kaynor Tech | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/23 | JV Girls Volleyball | Kaynor Tech | Home - Augelli Court -- Crosby HS [Directions] | 4:45 p.m. | ||
| Thu., 10/25 | FR Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 5:00 p.m. | ||
| Thu., 10/25 | V Boys Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | W 2-1 | |
| Thu., 10/25 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/25 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 4:45 p.m. | ||
| Fri., 10/26 | V Football | Woodland | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 7:00 p.m. | L 0-40 | |
| Sat., 10/27 | V Boys Cross Country | Class Championships | Away | TBA | ||
| Sat., 10/27 | JV Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | Cancelled | Cancelled | |
| Sat., 10/27 | V Girls Cross Country | Class Championships | Away | TBA | ||
| Mon., 10/29 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | ||
| Wed., 10/31 | FR Football | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | ||
| Fri., 11/2 | V Football | Derby | Away - Oxford HS - Turf Field [Directions] | 5:30 p.m. | L 20-66 | |
| Sat., 11/3 | V Boys Cross Country | State Open Championships | Away | TBA | ||
| Sat., 11/3 | JV Football | Naugatuck | Away - Naugatuck HS [Directions] | Cancelled | Cancelled | |
| Sat., 11/3 | V Girls Cross Country | State Open Championships | Away | TBA | ||
| Thu., 11/8 | V Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | L 6-57 | |
| Sat., 11/10 | JV Football | Watertown | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | Cancelled | Cancelled | |
| Wed., 11/14 | FR Football | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | ||
| Sat., 11/17 | JV Football | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | Cancelled | Cancelled | |
| Wed., 11/21 | V Football | Kennedy | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 6:00 p.m. | L 0-36 | |
| Tue., 12/11 | V Girls Basketball | Oxford | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | W 45-38 | |
| Thu., 12/13 | FR Boys Basketball | Woodland | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Thu., 12/13 | V Girls Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 6:00 p.m. | W 35-31 | |
| Fri., 12/14 | V Boys Basketball | Woodland | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 106-59 | |
| Fri., 12/14 | JV Boys Basketball | Woodland | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 12/14 | V Boys Indoor Track | Hillhouse Invitational Day 1 | Away - Hillhouse | 4:00 p.m. | ||
| Fri., 12/14 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | ||
| Sat., 12/15 | V Boys Indoor Track | Hillhouse Invitational Day 2 | Away - Hillhouse | 9:00 a.m. | ||
| Mon., 12/17 | FR Boys Basketball | St. Paul Catholic | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Tue., 12/18 | V Boys Basketball | St. Paul Catholic | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 86-56 | |
| Tue., 12/18 | JV Boys Basketball | St. Paul Catholic | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Wed., 12/19 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 35-46 | |
| Thu., 12/20 | V Boys Basketball | East Hartford | Away - East Hartford HS [Directions] | 7:00 p.m. | L 79-84 | |
| Thu., 12/20 | JV Boys Basketball | East Hartford | Away - East Hartford HS [Directions] | 5:30 p.m. | ||
| Thu., 12/20 | V Girls Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 6:00 p.m. | W 45-20 | |
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away - Hillhouse | 11:30 a.m. | ||
| Thu., 12/27 | V Girls Basketball | WCA | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | L 35-47 | |
| Fri., 12/28 | V Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 7:00 p.m. | L 75-95 | |
| Fri., 12/28 | JV Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | ||
| Fri., 12/28 | FR Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 11:00 a.m. | ||
| Wed., 1/2 | V Boys Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | W 77-72 | |
| Wed., 1/2 | JV Boys Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Wed., 1/2 | V Girls Basketball | Torrington | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 44-35 | |
| Thu., 1/3 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | ||
| Fri., 1/4 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | L 54-82 | |
| Fri., 1/4 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Oxford | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Fri., 1/4 | V Girls Basketball | Sacred Heart | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 60-64 | |
| Sat., 1/5 | V Boys Indoor Track | Elm City Coaches' Invitational | Away - Hillhouse | 9:00 a.m. | ||
| Mon., 1/7 | FR Boys Basketball | Holy Cross | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Tue., 1/8 | V Boys Basketball | Holy Cross | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 86-70 | |
| Tue., 1/8 | JV Boys Basketball | Holy Cross | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Tue., 1/8 | V Boys Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/8 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 6:00 p.m. | L 28-60 | |
| Thu., 1/10 | FR Boys Basketball | Kennedy | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Fri., 1/11 | V Boys Basketball | Kennedy | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 86-70 | |
| Fri., 1/11 | JV Boys Basketball | Kennedy | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 1/11 | V Boys Indoor Track | Yale Invitational Day 1 | Away - Yale - Coxe Cage | TBA | ||
| Fri., 1/11 | V Boys Swimming and Diving | Seymour | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Fri., 1/11 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 6:00 p.m. | L 31-36 | |
| Sat., 1/12 | V Boys Indoor Track | Yale Invitational Day 2 | Away - Yale - Coxe Cage | TBA | ||
| Mon., 1/14 | V Boys Basketball | Seymour | Away - Seymour HS [Directions] | 7:00 p.m. | W 93-50 | |
| Mon., 1/14 | JV Boys Basketball | Seymour | Away - Seymour HS [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | V Girls Basketball | Seymour | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 40-52 | |
| Tue., 1/15 | FR Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 1/15 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Wed., 1/16 | V Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 7:00 p.m. | W 93-41 | |
| Wed., 1/16 | JV Boys Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/16 | V Girls Basketball | Wilby | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | W 73-27 | |
| Fri., 1/18 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 6:00 p.m. | W 55-51 | |
| Sat., 1/19 | V Boys Indoor Track | SCC Coaches' Meet | Away - Hillhouse | 9:00 a.m. | ||
| Wed., 1/23 | V Boys Basketball | Ansonia | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 103-54 | |
| Wed., 1/23 | JV Boys Basketball | Ansonia | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Wed., 1/23 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 5:00 p.m. | L 32-55 | |
| Thu., 1/24 | FR Boys Basketball | Sacred Heart | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Fri., 1/25 | V Boys Basketball | Sacred Heart | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 58-64 | |
| Fri., 1/25 | JV Boys Basketball | Sacred Heart | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 6:00 p.m. | L 50-59 | |
| Mon., 1/28 | V Boys Indoor Track | NVL Championships | Away - Hillhouse | 4:30 p.m. | ||
| Thu., 1/31 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 59-65 | |
| Thu., 1/31 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Boys Basketball | WCA | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Thu., 1/31 | V Girls Basketball | Brookfield | Home - Augelli Court -- Crosby HS [Directions] | 5:00 p.m. | L 37-48 | |
| Fri., 2/1 | V Boys Basketball | WCA | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 70-79 | |
| Fri., 2/1 | JV Boys Basketball | WCA | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | Kennedy | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Fri., 2/1 | V Girls Basketball | WCA | Away - Waterbury Career Academy [Directions] | 6:00 p.m. | L 42-45 | |
| Sat., 2/2 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Mon., 2/4 | V Boys Basketball | Wilby | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 107-63 | |
| Mon., 2/4 | JV Boys Basketball | Wilby | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Mon., 2/4 | V Girls Basketball | Wilby | Away - Reggie O'Brien Gymnasium [Directions] | 6:00 p.m. | W 73-19 | |
| Tue., 2/5 | FR Boys Basketball | Wilby | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Wed., 2/6 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | ||
| Thu., 2/7 | FR Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | ||
| Fri., 2/8 | V Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | W 109-70 | |
| Fri., 2/8 | JV Boys Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | V Boys Indoor Track | CIAC Boys' Class L Meet | Away - Hillhouse | 4:00 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Kennedy | Home - Augelli Court -- Crosby HS [Directions] | 6:00 p.m. | W 52-46 | |
| Sat., 2/9 | V Boys Indoor Track | CIAC Girls' Class M Meet | Away - Hillhouse | 10:00 a.m. | ||
| Mon., 2/11 | FR Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | ||
| Mon., 2/11 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | ||
| Thu., 2/14 | V Girls Basketball | Watertown | Home - Augelli Court -- Crosby HS [Directions] | 5:00 p.m. | L 32-61 | |
| Fri., 2/15 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 6:00 p.m. | W 92-47 | |
| Fri., 2/15 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 4:30 p.m. | ||
| Fri., 2/15 | V Girls Basketball | Holy Cross | Home - Augelli Court -- Crosby HS [Directions] | 10:00 a.m. | L 23-58 | |
| Sat., 2/16 | V Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:00 p.m. | W 90-73 | |
| Sat., 2/16 | JV Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 1:30 p.m. | ||
| Sat., 2/16 | FR Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 2/16 | V Boys Indoor Track | CIAC State Opens | Away - Hillhouse | TBA | ||
| Mon., 2/18 | FR Boys Basketball | Naugatuck | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | ||
| Tue., 2/19 | V Boys Basketball | Naugatuck | Home - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | L 66-75 | |
| Tue., 2/19 | JV Boys Basketball | Naugatuck | Home - Augelli Court -- Crosby HS [Directions] | 5:30 p.m. | ||
| Tue., 2/19 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:00 p.m. | ||
| Wed., 2/20 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Thu., 2/21 | V Boys Swimming and Diving | Nonnewaug | Home - Crosby HS [Directions] | 4:00 p.m. | ||
| Fri., 2/22 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 4:15 p.m. | W 99-59 | |
| Fri., 2/22 | V Boys Swimming and Diving | Wilby/Kaynor, Danbury | Away - Wilby HS [Directions] | 5:00 p.m. | ||
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Boston, MA | TBA | ||
| Sat., 3/30 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 12:00 p.m. | L 0-10 | |
| Mon., 4/1 | V Baseball | Kaynor Tech | Away - Kaynor Tech Baseball Field [Directions] | 3:45 p.m. | W 13-8 | |
| Mon., 4/1 | V Boys Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | L 0-5 | |
| Mon., 4/1 | V Softball | Kaynor Tech | Home - Municipal Stadium [Directions] | 3:45 p.m. | L 12-4 | |
| Mon., 4/1 | V Girls Tennis | St. Paul Catholic | Home - Crosby HS [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/2 | V Baseball | Derby | Away - Naugatuck HS [Directions] | 3:45 p.m. | L 1-22 | |
| Tue., 4/2 | V Boys Outdoor Track | Oxford, Woodland | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Girls Outdoor Track | Oxford, Woodland | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Softball | Derby | Home - Municipal Stadium [Directions] | 4:00 p.m. | L 21-2 | |
| Wed., 4/3 | V Boys Tennis | Watertown | Home - Crosby HS [Directions] | 3:30 p.m. | L 0-5 | |
| Thu., 4/4 | V Boys Tennis | Wolcott | Home - Crosby HS [Directions] | 3:45 p.m. | L 0-5 | |
| Thu., 4/4 | V Softball | Ansonia | Away - Ansonia HS [Directions] | 4:00 p.m. | L 15-5 | |
| Thu., 4/4 | V Girls Tennis | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/6 | V Baseball | Ansonia | Home - Washington Park [Directions] | 2:00 p.m. | L 0-12 | |
| Sat., 4/6 | V Girls Tennis | Kennedy | Home - Crosby HS [Directions] | 11:00 a.m. | L 2-5 | |
| Sat., 4/6 | V Girls Tennis | Kennedy | Away - Crosby HS [Directions] | 12:30 p.m. | L 3-4 | |
| Mon., 4/8 | V Baseball | Seymour | Home - Washington Park [Directions] | 4:00 p.m. | L 0-10 | |
| Mon., 4/8 | V Boys Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 1-4 | |
| Mon., 4/8 | V Softball | Wolcott | Home - Huntingdon Park [Directions] | 3:45 p.m. | L 19-0 | |
| Mon., 4/8 | V Girls Tennis | Holy Cross | Home - Crosby HS [Directions] | 3:30 p.m. | L 0-7 | |
| Tue., 4/9 | V Boys Outdoor Track | Torrington, Wilby | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 4/9 | V Girls Outdoor Track | Torrington, Wilby | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:45 p.m. | L 0-17 | |
| Wed., 4/10 | V Boys Tennis | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 4/10 | V Softball | Woodland | Away - Woodland Softball Field [Directions] | 4:00 p.m. | L 0-18 | |
| Wed., 4/10 | V Girls Tennis | Seymour | Home - Crosby HS [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/11 | JV Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Boys Outdoor Track | St. Paul Catholic, Sacred Heart | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Girls Outdoor Track | St. Paul Catholic, Sacred Heart | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | JV Softball | Woodland | Away - Woodland Softball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/12 | V Baseball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 0-12(5) | |
| Fri., 4/12 | V Softball | Holy Cross | Home - Crosby HS Field #1 [Directions] | 4:00 p.m. | L 21-0 | |
| Sun., 4/14 | V Baseball | WCA | Home - Washington Park [Directions] | 4:00 p.m. | L 3-5 | |
| Mon., 4/15 | V Softball | WCA | Away - Municipal Stadium [Directions] | 2:00 p.m. | L 4-19 | |
| Tue., 4/16 | JV Baseball | WCA | Home - Washington Park [Directions] | 11:00 a.m. | ||
| Tue., 4/16 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | 11:00 a.m. | W 2-1 | |
| Tue., 4/16 | V Boys Tennis | Wilby | Away - Wilby H.S. [Directions] | 12:00 p.m. | W 2-1 | |
| Tue., 4/16 | JV Softball | WCA | Away - Huntingdon Park [Directions] | 10:30 a.m. | ||
| Wed., 4/17 | V Baseball | Kennedy | Home - Crosby HS [Directions] | 11:00 a.m. | W 12-6 | |
| Wed., 4/17 | V Boys Tennis | Kennedy | Away - Crosby HS [Directions] | 10:00 a.m. | L 0-5 | |
| Wed., 4/17 | V Boys Tennis | Kennedy | Home - Crosby HS [Directions] | 11:30 a.m. | L 0-5 | |
| Wed., 4/17 | V Softball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 10:00 a.m. | L 0-23 | |
| Thu., 4/18 | V Baseball | Wilby | Away - Municipal Stadium [Directions] | 11:00 a.m. | W 14-13 | |
| Thu., 4/18 | V Boys Tennis | Sacred Heart | Home - Crosby HS [Directions] | 10:30 a.m. | L 2-3 | |
| Thu., 4/18 | V Boys Tennis | Sacred Heart | Away - Crosby HS | 12:00 p.m. | L 1-4 | |
| Thu., 4/18 | V Softball | Wilby | Home - Crosby HS Field #1 [Directions] | 3:45 p.m. | W 23-20 | |
| Mon., 4/22 | V Boys Golf | Wolcott | Home - Western Hills [Directions] | 2:30 p.m. | Wolcott 208 Kennedy 280 | |
| Tue., 4/23 | V Boys Outdoor Track | Wolcott, Seymour | Away - Wolcott HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Wolcott, Seymour | Away [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Baseball | Sacred Heart | Away - Crosby HS | 3:45 p.m. | L 4-14 | |
| Wed., 4/24 | V Boys Golf | St. Paul Catholic | Away [Directions] | 2:30 p.m. | 138 St. Paul Kennedy 237 Wilby 241 | |
| Wed., 4/24 | V Softball | Sacred Heart | Home - Crosby HS Field #1 [Directions] | 4:00 p.m. | L 20-2 | |
| Thu., 4/25 | JV Baseball | Sacred Heart | Away - Fulton Park | 3:45 p.m. | ||
| Thu., 4/25 | V Boys Golf | Seymour | Away - Oxford Greens [Directions] | 2:30 p.m. | Seymour 186 Wilby 270 Kennedy 280 | |
| Thu., 4/25 | V Softball | Oxford | Away - OHS Softball Field [Directions] | 4:00 p.m. | L 1-21 | |
| Thu., 4/25 | V Girls Tennis | Torrington | Home - Crosby HS [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Bethel HS | 9:00 a.m. | ||
| Mon., 4/29 | V Boys Golf | Watertown | Away [Directions] | 2:30 p.m. | forfeit | |
| Mon., 4/29 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | L 0-7 | |
| Tue., 4/30 | V Boys Outdoor Track | Kennedy, Watertown | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Kennedy, Watertown | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Watertown | Home - Crosby HS [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/1 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/1 | V Boys Golf | Naugatuck, Wilby | Home - Western Hills [Directions] | 2:30 p.m. | Naugatuck 221 Wilby 281 Kennedy 288 | |
| Wed., 5/1 | V Softball | Torrington | Home - Crosby HS Field #1 [Directions] | 4:00 p.m. | L 22-0 | |
| Wed., 5/1 | V Girls Tennis | Wilby | Home - Crosby HS [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/1 | V Girls Tennis | Wilby | Away - Crosby HS [Directions] | 4:15 p.m. | W 7-0 | |
| Thu., 5/2 | V Boys Tennis | Naugatuck | Home - Crosby HS [Directions] | 3:30 p.m. | L 0-5 | |
| Thu., 5/2 | V Girls Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | L 0-7 | |
| Sat., 5/4 | V Baseball | WCA | Away - Waterville Park [Directions] | 2:00 p.m. | L 0-7 | |
| Mon., 5/6 | V Baseball | Wilby | Home - Wilby HS [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 5/6 | V Boys Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 4:45 p.m. | L 1-4 | |
| Mon., 5/6 | V Softball | Wilby | Away - Bucks Hill Park [Directions] | 4:00 p.m. | W 30-11 | |
| Mon., 5/6 | V Softball | WCA | Home - Municipal Stadium [Directions] | 7:00 p.m. | L 23-6 | |
| Mon., 5/6 | V Girls Tennis | Sacred Heart | Home - Crosby HS [Directions] | 2:45 p.m. | L 0-7 | |
| Mon., 5/6 | V Girls Tennis | Sacred Heart | Away - Crosby HS | 3:45 p.m. | L 1-6 | |
| Tue., 5/7 | V Baseball | Naugatuck | Home - Naugatuck HS [Directions] | 3:30 p.m. | L 1-16 | |
| Tue., 5/7 | V Boys Outdoor Track | Holy Cross, WCA | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Holy Cross, WCA | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | L 0-15 | |
| Wed., 5/8 | V Baseball | Holy Cross | Home - Washington Park [Directions] | 4:00 p.m. | L 0-34 | |
| Wed., 5/8 | V Boys Tennis | Woodland | Home - Crosby HS [Directions] | 3:30 p.m. | L 0-5 | |
| Wed., 5/8 | V Boys Tennis | Watertown | Home - Crosby HS [Directions] | 4:00 p.m. | L 0-5 | |
| Wed., 5/8 | V Softball | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | 4:00 p.m. | L 0-23 | |
| Wed., 5/8 | V Girls Tennis | Woodland | Away - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 0-7 | |
| Thu., 5/9 | V Boys Golf | Woodland | Away [Directions] | 2:30 p.m. | Kennedy 285 | |
| Thu., 5/9 | V Softball | Kennedy | Home - Crosby HS Field #1 [Directions] | 3:45 p.m. | L 21-3 | |
| Thu., 5/9 | V Girls Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | L 0-7 | |
| Fri., 5/10 | V Baseball | Kennedy | Away - Municipal Stadium [Directions] | 7:00 p.m. | W 10-3 | |
| Fri., 5/10 | V Boys Outdoor Track | Torrington Invite | Away - Torrington HS | 4:00 p.m. | ||
| Sat., 5/11 | JV Baseball | WCA | Away - Washington Park [Directions] | 10:00 a.m. | ||
| Tue., 5/14 | V Baseball | Watertown | Home - Washington Park [Directions] | 7:00 p.m. | L 0-12 | |
| Tue., 5/14 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | 2:30 p.m. | Kennedy 285 | |
| Tue., 5/14 | V Boys Outdoor Track | City Championships | Home - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Softball | Watertown | Home - Municipal Stadium [Directions] | 4:00 p.m. | L 25-0 | |
| Wed., 5/15 | V Baseball | Sacred Heart | Home - Waterville Park [Directions] | 3:45 p.m. | L 0-13 | |
| Wed., 5/15 | V Softball | Terryville | Away - Terryville HS [Directions] | 4:00 p.m. | L 3-18 | |
| Thu., 5/16 | V Baseball | Harding | Away - Harding HS Field-Baseball [Directions] | 4:00 p.m. | W 13-10 | |
| Thu., 5/16 | V Boys Golf | Woodland | Home - Western Hills [Directions] | 2:30 p.m. | Kennedy 285 | |
| Thu., 5/16 | V Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | 5:30 p.m. | L 1-17 | |
| Fri., 5/17 | V Boys Outdoor Track | 17th Dream Invite | Away - Danbury HS | 7:30 p.m. | ||
| Mon., 5/20 | V Boys Golf | Holy Cross, Wilby | Away - Western Hills [Directions] | 2:30 p.m. | 288Kennedy | |
| Tue., 5/21 | V Boys Outdoor Track | NVL Championship | Away - Torrington HS | 1:30 p.m. | ||
| Wed., 5/22 | V Boys Golf | Sacred Heart | Home - Western Hills [Directions] | 2:30 p.m. | 288 Kennedy | |
| Wed., 5/22 | V Boys Outdoor Track | NVL JV Meet | Away | TBA | ||
| Tue., 5/28 | V Boys Outdoor Track | Class L Meet | Away - Middletown HS | 3:00 p.m. | ||
| Mon., 6/3 | V Boys Outdoor Track | State Open Meet | Away - Willowbrook Park | 1:30 p.m. | ||