| Seymour 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 541 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Baseball | West Haven (Scrim.) | Away - Whitey Piurek Field [Directions] | TBA | ||
| TBA | V Baseball | Thomaston (Scrim.) | Home - French Park [Directions] | TBA | ||
| TBA | JV Baseball | St. Paul Catholic | Home - French Park [Directions] | 10:00 a.m. | ||
| TBA | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 11:30 a.m. | ||
| TBA | JV Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Sacred Heart | Home - French Park [Directions] | TBA | ||
| TBA | JV Baseball | Wolcott | Away - Wolcott HS [Directions] | TBA | ||
| TBA | JV Baseball | Kennedy | Away - Waterville Park [Directions] | TBA | ||
| TBA | JV Boys Basketball | Ansonia | Home - Seymour HS [Directions] | TBA | ||
| TBA | FM Football | St. Paul Catholic | Home - Seymour HS Turf Field [Directions] | TBA | ||
| TBA | FM Football | Woodland | Home - Seymour HS Turf Field [Directions] | TBA | ||
| TBA | JV Boys Soccer | Ansonia | Home - Seymour High Lower Field [Directions] | TBA | ||
| TBA | JV Boys Soccer | Naugatuck | Away - Breen SS (JV & Fr.) [Directions] | TBA | ||
| TBA | JV Boys Soccer | Holy Cross | Away - Upper Murray Park [Directions] | TBA | ||
| TBA | JV Boys Soccer | Wolcott | Away [Directions] | Cancelled | Cancelled | |
| TBA | JV Boys Soccer | St. Paul Catholic | Home - Seymour HS Turf Field [Directions] | TBA | ||
| TBA | JV Boys Soccer | Woodland | Home - Seymour HS Turf Field [Directions] | TBA | ||
| TBA | JV Boys Soccer | Sacred Heart | Away - Waterville Park | TBA | ||
| TBA | JV Girls Basketball | Ansonia | Home - Seymour HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | TBA | ||
| TBA | JV Girls Basketball | WCA | Home - Seymour HS [Directions] | TBA | ||
| TBA | FR Girls Basketball | Woodland | Home - Seymour HS [Directions] | TBA | ||
| TBA | FR Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | TBA | ||
| TBA | V Softball | Masuk (Scrim.) | Away - Masuk HS Softball Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Woodland | Home - Seymour HS [Directions] | 3:30 p.m. | ||
| TBA | JV Softball | St. Paul Catholic | Home - Seymour HS [Directions] | 4:30 p.m. | ||
| TBA | JV Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | V Girls Volleyball | Trumbull (Scrim.) | Home - Seymour HS [Directions] | TBA | ||
| Tue., 8/28 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Seymour HS Turf Field [Directions] | 7:00 p.m. | ||
| Tue., 8/28 | V Girls Soccer | Shepaug Valley (Scrim.) | Home - Seymour HS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 8/28 | V Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Tue., 8/28 | JV Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Thu., 8/30 | V Football | Rocky Hill (Scrim.) | Home - Seymour HS Turf Field [Directions] | 7:00 p.m. | ||
| Thu., 8/30 | V Girls Volleyball | Newtown (Scrim.) | Away - Newtown HS Gymnasium [Directions] | 3:15 p.m. | ||
| Sat., 9/1 | V Boys Soccer | Amity (Scrim.) | Away [Directions] | TBA | ||
| Sat., 9/1 | V Girls Soccer | Shelton (Scrim.) | Away [Directions] | 7:30 a.m. | ||
| Fri., 9/7 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 4:00 p.m. | W 8-1 | |
| Fri., 9/7 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 9/7 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 9/8 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 1:30 p.m. | W 43-14 | |
| Sat., 9/8 | V Boys Soccer | Ansonia | Home - Seymour HS Turf Field [Directions] | 2:00 p.m. | W 4-2 | |
| Sat., 9/8 | V Girls Volleyball | Invitational CT Sports Center | Away | 8:00 a.m. | ||
| Tue., 9/11 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/11 | V Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | L 1-3 | |
| Tue., 9/11 | V Girls Volleyball | East Haven | Away - East Haven HS [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/11 | JV Girls Volleyball | East Haven | Away - East Haven HS [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 9/12 | V Boys Cross Country | Oxford, St. Paul Catholic, Kennedy | Away - OHS Wolverine Field (Turf) [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Girls Cross Country | Oxford, St. Paul Catholic, Kennedy | Away - OHS Wolverine Field (Turf) [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | Win - Seymour 94, Sacred Heart 83 | |
| Thu., 9/13 | V Girls Soccer | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | L 0-6 | |
| Thu., 9/13 | V Girls Volleyball | Wilby | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/13 | JV Girls Volleyball | Wilby | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 9/14 | V Football | Kennedy | Home - Seymour HS Turf Field [Directions] | 7:00 p.m. | W 48-12 | |
| Fri., 9/14 | V Boys Soccer | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | L 2-3 | |
| Fri., 9/14 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 9/14 | V Girls Volleyball | Crosby | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/14 | JV Girls Volleyball | Crosby | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 9/15 | V Boys Cross Country | Wilton Invitational | Away - Allen's Meadows Park | 9:00 a.m. | ||
| Sat., 9/15 | V Girls Cross Country | Wilton Invitational | Away - Allen's Meadows Park | 9:00 a.m. | ||
| Mon., 9/17 | V Girls Soccer | Derby | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 8-0 | |
| Tue., 9/18 | V Girls Swimming and Diving | Oxford | Away - OHS Pool [Directions] | 4:00 p.m. | Win - Seymour 83, Oxford 72 | |
| Tue., 9/18 | V Girls Volleyball | Oxford | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/18 | JV Girls Volleyball | Oxford | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 9/19 | V Boys Cross Country | Naugatuck, WCA, Woodland | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 9/19 | JV Boys Soccer | Derby | Away [Directions] | Cancelled | Cancelled | |
| Wed., 9/19 | V Girls Cross Country | Naugatuck, WCA, Woodland | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 9/19 | V Girls Soccer | Naugatuck | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 3-6 | |
| Wed., 9/19 | V Girls Volleyball | Bristol Central | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 9/19 | JV Girls Volleyball | Bristol Central | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-1 | |
| Fri., 9/21 | V Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 47-6 | |
| Fri., 9/21 | V Boys Soccer | Wolcott | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 4-0 | |
| Fri., 9/21 | V Girls Soccer | Wolcott | Home - Seymour HS Turf Field [Directions] | 4:00 p.m. | L 1-2 | |
| Fri., 9/21 | V Girls Swimming and Diving | Woodland | Home - Seymour HS [Directions] | 4:00 p.m. | Win - Seymour 91, Woodland 74 | |
| Fri., 9/21 | V Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 5:00 p.m. | W 3-0 | |
| Fri., 9/21 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 3:45 p.m. | W 2-0 | |
| Sat., 9/22 | FM Football | Holy Cross | Home - Seymour HS Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 9/22 | V Boys Soccer | Derby | Away - Derby -Witek Park [Directions] | 10:00 a.m. | W 7-0 | |
| Mon., 9/24 | V Boys Soccer | Wilby | Home - Seymour HS Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 9/25 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:00 p.m. | Win - Seymour 98, Watertown 83 | |
| Tue., 9/25 | V Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Tue., 9/25 | JV Girls Volleyball | Woodland | Away - Woodland HS Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 9/26 | V Boys Cross Country | Torrington, Derby, Wolcott | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Wed., 9/26 | JV Boys Soccer | Wilby | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | T 1-1 | |
| Wed., 9/26 | V Girls Cross Country | Torrington, Derby, Wolcott | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Thu., 9/27 | V Girls Soccer | Woodland | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 9/27 | V Girls Volleyball | Wolcott | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/27 | JV Girls Volleyball | Wolcott | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 9/28 | V Football | Holy Cross | Home - Seymour HS Turf Field [Directions] | 7:00 p.m. | W 14-13 | |
| Fri., 9/28 | V Boys Soccer | Kennedy | Away - Municipal Stadium [Directions] | 3:30 p.m. | W 2-1 | |
| Fri., 9/28 | V Girls Swimming and Diving | Kennedy | Home - Seymour HS [Directions] | 4:00 p.m. | Win - Seymour 77, Kennedy 61 | |
| Sat., 9/29 | JV Boys Soccer | Kennedy | Away - West Side MS [Directions] | 10:00 a.m. | L 4-1 | |
| Sat., 9/29 | V Girls Soccer | Sacred Heart | Away - Waterville Park | 10:30 a.m. | L Forfeit | |
| Tue., 10/2 | V Boys Cross Country | Crosby, Watertown, Wilby | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Girls Cross Country | Crosby, Watertown, Wilby | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | 4:00 p.m. | Win - Seymour 91, Wilby/Kaynor/WCA 69 | |
| Tue., 10/2 | V Girls Volleyball | Ansonia | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/2 | JV Girls Volleyball | Ansonia | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/3 | V Boys Soccer | WCA | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 7-0 | |
| Thu., 10/4 | JV Boys Soccer | WCA | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 10/4 | V Girls Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | L 1-0 | |
| Fri., 10/5 | V Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | L 27-34 | |
| Fri., 10/5 | V Boys Soccer | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:45 p.m. | L 0-3 | |
| Fri., 10/5 | V Girls Swimming and Diving | Naugatuck | Home - Seymour HS [Directions] | 4:00 p.m. | Win - Seymour 94, Naugatuck 74 | |
| Fri., 10/5 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/5 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/6 | FM Football | Torrington | Home - Seymour HS Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/6 | JV Boys Soccer | Crosby | Away - Crosby HS - grass soccer field [Directions] | 11:00 a.m. | W 2-1 | |
| Tue., 10/9 | V Boys Cross Country | Holy Cross, Sacred Heart | Away - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Soccer | Torrington | Home - Seymour HS Turf Field [Directions] | 4:00 p.m. | T 2-2 | |
| Tue., 10/9 | V Girls Cross Country | Holy Cross, Sacred Heart | Away - Holy Cross HS [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Soccer | Torrington | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L Forfeit | |
| Tue., 10/9 | V Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/9 | JV Girls Volleyball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/10 | V Girls Swimming and Diving | St. Joseph | Home - Seymour HS [Directions] | 6:00 p.m. | Win - Seymour 87, St. Joseph 69 | |
| Thu., 10/11 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/11 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 10/12 | V Boys Soccer | Oxford | Home - Seymour HS Turf Field [Directions] | 4:00 p.m. | W 5-3 | |
| Fri., 10/12 | V Girls Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | T 2-2 | |
| Fri., 10/12 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Seymour HS [Directions] | 4:00 p.m. | Win - Seymour 88, St. Paul 71 | |
| Fri., 10/12 | V Girls Volleyball | St. Paul Catholic | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/12 | JV Girls Volleyball | St. Paul Catholic | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/13 | JV Boys Soccer | Oxford | Home - Seymour HS Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/15 | JV Boys Soccer | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Tue., 10/16 | V Girls Soccer | St. Paul Catholic | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 1-2 | |
| Tue., 10/16 | V Girls Swimming and Diving | Torrington | Home - Seymour HS [Directions] | 6:30 p.m. | Win - Seymour 86, Torrington 76 | |
| Tue., 10/16 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/16 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 10/17 | V Boys Cross Country | NVL Championships | Away - Veterans Park | TBA | ||
| Wed., 10/17 | V Girls Cross Country | NVL Championships | Away - Veterans Park | TBA | ||
| Thu., 10/18 | V Boys Soccer | Watertown | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 1-2 | |
| Thu., 10/18 | V Girls Soccer | Watertown | Home - Seymour HS Turf Field [Directions] | 4:00 p.m. | L 2-7 | |
| Fri., 10/19 | V Football | Oxford | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 45-27 | |
| Fri., 10/19 | JV Boys Soccer | Watertown | Home - Seymour High Lower Field [Directions] | 3:45 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/19 | JV Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/20 | FM Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Mon., 10/22 | V Boys Soccer | Woodland | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/22 | V Girls Volleyball | Woodland | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/22 | JV Girls Volleyball | Woodland | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/24 | V Boys Soccer | St. Paul Catholic | Home - Seymour HS Turf Field [Directions] | 3:30 p.m. | W 5-2 | |
| Wed., 10/24 | V Girls Soccer | Sacred Heart | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 8-1 | |
| Wed., 10/24 | V Girls Volleyball | Naugatuck | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/24 | JV Girls Volleyball | Naugatuck | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Thu., 10/25 | V Boys Soccer | Sacred Heart | Away - Crosby HS - turf field | 6:30 p.m. | W 5-0 | |
| Fri., 10/26 | V Boys Cross Country | CIAC Class M Championship | Away - Wickham Park - East Hartford [Directions] | 2:35 p.m. | ||
| Fri., 10/26 | V Football | Derby | Home - Seymour HS Turf Field [Directions] | 7:00 p.m. | W 57-12 | |
| Fri., 10/26 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park - East Hartford [Directions] | 1:30 p.m. | ||
| Sat., 10/27 | FM Football | Derby | Away [Directions] | Cancelled | Cancelled | |
| Sat., 10/27 | V Girls Volleyball | Oxford | Home - Seymour HS [Directions] | 1:30 p.m. | W 3-0 | |
| Mon., 10/29 | V Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | L 1-0 | |
| Mon., 10/29 | V Girls Volleyball | St. Paul Catholic | Home - Seymour MS [Directions] | 7:00 p.m. | ||
| Thu., 11/1 | V Football | Naugatuck | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 26-28 | |
| Thu., 11/1 | V Girls Volleyball | Kennedy | Home - Kennedy HS [Directions] | 7:00 p.m. | ||
| Fri., 11/2 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ||
| Fri., 11/2 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Sat., 11/3 | FM Football | Wilby | Home - Seymour HS Turf Field [Directions] | Cancelled | Cancelled | |
| Sat., 11/3 | FM Football | Wolcott | Home - Seymour HS Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 11/5 | V Girls Volleyball | CIAC Tourney 1st Round | Away - Higher Seed | TBA | ||
| Tue., 11/6 | V Boys Soccer | Suffield | Away - Ted Beneski Turf Field [Directions] | 2:00 p.m. | W 3-1 | |
| Wed., 11/7 | V Girls Volleyball | Rockville | Home - Seymour HS [Directions] | 6:00 p.m. | CIAC Tourney 2nd Round | |
| Thu., 11/8 | V Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 6:00 p.m. | L 0-35 | |
| Thu., 11/8 | V Boys Soccer | Watertown | Away - Higher Seed [Directions] | 3:30 p.m. | L 3-0 | CIAC Tourney 2nd Round |
| Fri., 11/9 | V Girls Volleyball | St. Joseph | Home - Seymour HS [Directions] | 6:00 p.m. | CIAC Tourney Quarterfinals | |
| Sat., 11/10 | V Boys Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| Sat., 11/10 | FM Football | Sacred Heart | Away - Municipal Stadium | Cancelled | Cancelled | |
| Sat., 11/10 | FM Football | Holy Cross | Away - Seymour HS [Directions] | 10:00 a.m. | ||
| Sat., 11/10 | V Boys Soccer | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| Tue., 11/13 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Girls Volleyball | Woodland | Home - Pomperaug [Directions] | 6:00 p.m. | CIAC Tourney Semifinals | |
| Sat., 11/17 | V Boys Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | V Girls Volleyball | Weston | Home - East Haven [Directions] | 4:00 p.m. | CIAC Tourney Final | |
| Wed., 11/21 | V Football | Woodland | Away - Woodland Football Field [Directions] | 5:30 p.m. | L 12-14 | |
| Sat., 12/1 | V Boys Ice Hockey | Westfield (MA) (Scrim.) | Away | 2:00 p.m. | ||
| Sat., 12/1 | V Girls Basketball | Amity (Scrim.) | Away [Directions] | TBA | ||
| Sun., 12/2 | V Boys Ice Hockey | Longmeadow (MA) (Scrim.) | Away | 4:30 p.m. | ||
| Tue., 12/4 | V Boys Basketball | Platt Tech (Scrim.) | Home - Seymour HS [Directions] | 3:30 p.m. | ||
| Tue., 12/4 | V Girls Basketball | Fairfield Ludlowe (Scrim.) | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/6 | V Boys Basketball | Shelton (Scrim.) | Home - Seymour HS [Directions] | 3:30 p.m. | ||
| Thu., 12/6 | V Girls Basketball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/7 | V Boys Ice Hockey | Jamboree | Home - Bennett Rink [Directions] | 6:00 p.m. | ||
| Sat., 12/8 | V Boys Ice Hockey | Alumni Game | Home - Bennett Rink [Directions] | 7:00 p.m. | ||
| Sat., 12/8 | V Girls Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS Gym [Directions] | 11:00 a.m. | ||
| Mon., 12/10 | V Boys Basketball | Amity (Scrim.) | Away - Paul D. Mengold Gym at Amity HS [Directions] | 5:00 p.m. | ||
| Mon., 12/10 | FR Girls Basketball | Woodland | Away [Directions] | 3:45 p.m. | ||
| Tue., 12/11 | V Girls Basketball | Joel Barlow | Away - Masuk HS [Directions] | 5:15 p.m. | L 48-50 | |
| Wed., 12/12 | V Boys Ice Hockey | Guilford | Home - Bennett Rink [Directions] | 5:00 p.m. | L 7-8 | |
| Wed., 12/12 | V Wrestling | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/13 | V Girls Basketball | Bassick | Away - Masuk HS [Directions] | 5:15 p.m. | W 59-42 | |
| Fri., 12/14 | V Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 48-64 | |
| Fri., 12/14 | JV Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 12/14 | V Boys Indoor Track | Hillhouse Invitational | Away - Hillhouse HS | 4:00 p.m. | ||
| Fri., 12/14 | V Girls Basketball | Holy Cross | Home - Seymour HS [Directions] | 7:00 p.m. | W 51-42 | |
| Fri., 12/14 | JV Girls Basketball | Holy Cross | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | FR Girls Basketball | Holy Cross | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Fri., 12/14 | V Girls Indoor Track | Hillhouse Invitational | Away - Hillhouse HS | 4:00 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | W 5-3 | |
| Sat., 12/15 | V Wrestling | Oxford Invitational | Away - Oxford HS | 10:00 a.m. | ||
| Mon., 12/17 | V Boys Basketball | Brookfield | Home - Seymour HS [Directions] | 7:00 p.m. | L 36-60 | |
| Mon., 12/17 | JV Boys Basketball | Brookfield | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Mon., 12/17 | FR Boys Basketball | Brookfield | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Mon., 12/17 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 4:30 p.m. | W 5-2 | |
| Tue., 12/18 | V Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | L 36-82 | |
| Tue., 12/18 | JV Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Tue., 12/18 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 3:45 p.m. | ||
| Tue., 12/18 | V Girls Basketball | Sacred Heart | Home - Seymour HS [Directions] | 7:00 p.m. | L 43-47 | |
| Tue., 12/18 | JV Girls Basketball | Sacred Heart | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 12/18 | FR Girls Basketball | Sacred Heart | Home - Seymour HS [Directions] | Cancelled | Cancelled | |
| Wed., 12/19 | V Boys Ice Hockey | Westhill/Stamford | Home - Bennett Rink [Directions] | 6:30 p.m. | W 5-2 | |
| Wed., 12/19 | V Wrestling | Thomaston | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 12/21 | V Boys Basketball | Torrington | Home - Seymour HS [Directions] | 7:00 p.m. | L 44-85 | |
| Fri., 12/21 | JV Boys Basketball | Torrington | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Torrington | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Fri., 12/21 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | W 56-23 | |
| Sat., 12/22 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 2:00 p.m. | W 38-13 | |
| Sat., 12/22 | JV Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 12:30 p.m. | ||
| Wed., 12/26 | V Boys Ice Hockey | Branford | Home - Bennett Rink [Directions] | 6:30 p.m. | L 2-0 | |
| Wed., 12/26 | V Wrestling | Terryville-Thomaston | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Sat., 12/29 | V Boys Indoor Track | 3rd Annual Wilton Wright Invitational | Away | 3:00 p.m. | ||
| Sat., 12/29 | V Wrestling | Holy Cross, Somers, Stratford | Home - Derby HS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/29 | V Girls Indoor Track | 3rd Annual Wilton Wright Invitational | Away | 3:00 p.m. | ||
| Wed., 1/2 | V Boys Basketball | Kennedy | Home - Seymour HS [Directions] | 7:00 p.m. | W 66-64 | |
| Wed., 1/2 | JV Boys Basketball | Kennedy | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 1/2 | FR Boys Basketball | Kennedy | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 1/2 | V Boys Ice Hockey | Simsbury | Away - Westminster School [Directions] | 6:00 p.m. | W 3-2 (OT) | |
| Wed., 1/2 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | W 41-32 | |
| Wed., 1/2 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | ||
| Thu., 1/3 | V Boys Indoor Track | 5th Annual Wintergreen Invitational | Away | TBA | ||
| Thu., 1/3 | V Wrestling | Northwestern | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/3 | V Girls Gymnastics | Fairfield Ludlowe, Darien | Away - GCA [Directions] | 6:30 p.m. | 112.35 | |
| Thu., 1/3 | V Girls Indoor Track | 5th Annual Wintergreen Invitational | Away | TBA | ||
| Fri., 1/4 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | L 66-81 | |
| Fri., 1/4 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | ||
| Fri., 1/4 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 3:30 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown HS [Directions] | 4:30 p.m. | ||
| Fri., 1/4 | V Girls Basketball | Wolcott | Home - Seymour HS [Directions] | 7:00 p.m. | W 35-28 | |
| Fri., 1/4 | JV Girls Basketball | Wolcott | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 1/4 | FR Girls Basketball | Wolcott | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Sat., 1/5 | V Boys Ice Hockey | Guilford | Away - East Haven Ice Rink [Directions] | 1:00 p.m. | L 5-4 | |
| Sat., 1/5 | V Boys Indoor Track | 3rd Annual James Barber Invitational | Away | TBA | ||
| Sat., 1/5 | V Wrestling | Lawless Tournament | Away - Nonnewaug HS | 9:30 a.m. | ||
| Sat., 1/5 | V Girls Gymnastics | Pomperaugh Invitational | Away [Directions] | TBA | 132.65 | |
| Sat., 1/5 | V Girls Indoor Track | 3rd Annual James Barber Invitational | Away | TBA | ||
| Tue., 1/8 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 46-79 | |
| Tue., 1/8 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Tue., 1/8 | V Girls Basketball | Ansonia | Home - Seymour HS [Directions] | 7:00 p.m. | L 51-56 | |
| Tue., 1/8 | V Girls Gymnastics | New Milford, Joel Barlow, Newtown | Away - New Milford HS [Directions] | 5:00 p.m. | 118.65 | |
| Wed., 1/9 | V Boys Ice Hockey | Cheshire | Home - Bennett Rink [Directions] | 6:00 p.m. | W 2-1 (OT) | |
| Thu., 1/10 | V Boys Basketball | Woodland | Home - Seymour HS [Directions] | 7:00 p.m. | L 45-62 | |
| Thu., 1/10 | JV Boys Basketball | Woodland | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | Woodland | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Thu., 1/10 | V Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 7:00 p.m. | W 50-40 | |
| Thu., 1/10 | JV Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/11 | V Boys Swimming and Diving | Crosby/WCA | Away - Crosby HS [Directions] | 4:00 p.m. | ||
| Sat., 1/12 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 1:00 p.m. | W 7-3 | |
| Sat., 1/12 | V Wrestling | Darien, Weston, Bunnell | Away - DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/12 | V Competitive Cheerleading | Hatter Fest | Away - Danbury HS | TBA | ||
| Sat., 1/12 | Winter Dance Team | Dancin'In The Woods | Away - Woodland HS | 4:00 p.m. | ||
| Mon., 1/14 | V Boys Basketball | Crosby | Home - Seymour HS [Directions] | 7:00 p.m. | L 50-93 | |
| Mon., 1/14 | JV Boys Basketball | Crosby | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | FR Boys Basketball | Crosby | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Mon., 1/14 | V Girls Basketball | Crosby | Away - Augelli Court -- Crosby HS [Directions] | 7:00 p.m. | W 52-40 | |
| Tue., 1/15 | V Boys Swimming and Diving | Woodland | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Tue., 1/15 | V Girls Gymnastics | Pomperaug, Nonnewaug, Newtown | Away - Auxiliary Gym [Directions] | 5:00 p.m. | 122.15 | |
| Wed., 1/16 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | W 73-43 | |
| Wed., 1/16 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/16 | V Boys Ice Hockey | Fairfield Prep | Home - Bennett Rink [Directions] | 6:00 p.m. | L 4-1 | |
| Wed., 1/16 | V Wrestling | Gilbert/Torrington | Away - Gilbert [Directions] | 6:00 p.m. | ||
| Wed., 1/16 | V Girls Basketball | Oxford | Home - Seymour HS [Directions] | 7:00 p.m. | W 46-31 | |
| Wed., 1/16 | JV Girls Basketball | Oxford | Home - Seymour HS [Directions] | Cancelled | Cancelled | |
| Wed., 1/16 | FR Girls Basketball | Holy Cross | Home - Seymour HS [Directions] | 3:00 p.m. | ||
| Thu., 1/17 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 56-84 | |
| Thu., 1/17 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | ||
| Thu., 1/17 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 3:30 p.m. | ||
| Thu., 1/17 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 7:00 p.m. | ||
| Thu., 1/17 | V Girls Basketball | Naugatuck | Home - Seymour HS [Directions] | 7:00 p.m. | L 57-58 | |
| Thu., 1/17 | JV Girls Basketball | Naugatuck | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Thu., 1/17 | FR Girls Basketball | Naugatuck | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Fri., 1/18 | V Boys Indoor Track | HK Invitational | Away - Hillhouse HS | 5:00 p.m. | ||
| Fri., 1/18 | V Girls Indoor Track | HK Invitational | Away - Hillhouse HS | 5:00 p.m. | ||
| Sat., 1/19 | V Wrestling | Eagle Classic | Away - East Catholic HS | 10:00 a.m. | ||
| Sat., 1/19 | V Girls Gymnastics | Joel Barlow, New Milford, Newtown | Away - Gymnastics & Cheerleading Academy - Fairfield [Directions] | Cancelled | Cancelled | |
| Tue., 1/22 | V Boys Swimming and Diving | Shelton | Away - Shelton Community Center Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/23 | V Boys Basketball | Watertown | Home - Seymour HS [Directions] | 7:00 p.m. | W 73-63 | |
| Wed., 1/23 | JV Boys Basketball | Watertown | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 1/23 | FR Boys Basketball | Watertown | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 1/23 | V Boys Ice Hockey | Hamden | Home - Bennett Rink [Directions] | 6:30 p.m. | L 2-10 | |
| Wed., 1/23 | V Wrestling | Nonnewaug, St. Joseph | Away - Nonnewaug HS Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/23 | V Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | W 49-39 | |
| Wed., 1/23 | JV Girls Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Wed., 1/23 | V Girls Gymnastics | Daniel Hand, Newtown, Hamden | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 6:00 p.m. | 128.5 | |
| Fri., 1/25 | V Boys Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 7:00 p.m. | L 50-57 | |
| Fri., 1/25 | JV Boys Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Boys Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Fri., 1/25 | V Boys Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 46-63 | |
| Fri., 1/25 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Fri., 1/25 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | V Girls Gymnastics | Wilton | Away [Directions] | 5:00 p.m. | 129.9 | |
| Sat., 1/26 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton - Lower [Directions] | 8:30 p.m. | L 1-2 | |
| Sat., 1/26 | V Wrestling | Doc Meyers Tournament | Away - Rocky Hill HS | 9:30 a.m. | ||
| Sat., 1/26 | V Competitive Cheerleading | QU Cheer and Dance Challenge | Away - Quinnipiac University | TBA | ||
| Sat., 1/26 | Winter Dance Team | QU Cheer & Dance Challenge | Away - Quinnipiac University | 5:00 p.m. | ||
| Sat., 1/26 | V Girls Gymnastics | Joel Barlow, New Milford, Newtown | Away [Directions] | 5:00 p.m. | 117.250 | |
| Mon., 1/28 | V Boys Ice Hockey | East Catholic | Home - Bennett Rink [Directions] | 5:45 p.m. | W 3-1 | |
| Mon., 1/28 | V Boys Indoor Track | NVL Championships | Away | 4:30 p.m. | ||
| Mon., 1/28 | V Girls Indoor Track | NVL Championships | Away - Hillhouse HS | 4:30 p.m. | ||
| Thu., 1/31 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 2/1 | V Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | L 52-65 | |
| Fri., 2/1 | JV Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | Wilby/Kaynor | Away - Wilby H.S. [Directions] | 6:00 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Derby | Home - Seymour HS [Directions] | 7:00 p.m. | W 54-35 | |
| Fri., 2/1 | JV Girls Basketball | Derby | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 2/1 | V Girls Gymnastics | Joel Barlow, Foran | Away - Gymnastics & Cheerleading Academy - Fairfield [Directions] | 6:30 p.m. | 135.30 | |
| Sat., 2/2 | V Wrestling | Four Corners Duals | Away - Canton H.S. | 10:00 a.m. | ||
| Mon., 2/4 | V Boys Indoor Track | Last Chance Relays | Away - Hillhouse HS | 5:00 p.m. | ||
| Mon., 2/4 | V Girls Indoor Track | Last Chance Relays | Away - Hillhouse HS | 5:00 p.m. | ||
| Tue., 2/5 | V Boys Basketball | Oxford | Home - Seymour HS [Directions] | 7:00 p.m. | W 58-41 | |
| Tue., 2/5 | JV Boys Basketball | Oxford | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | V Boys Swimming and Diving | Naugatuck | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | W 56-37 | |
| Tue., 2/5 | JV Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | Cancelled | Cancelled | |
| Wed., 2/6 | V Boys Ice Hockey | North Haven | Home - Bennett Rink [Directions] | 6:00 p.m. | W 7-2 | |
| Wed., 2/6 | V Wrestling | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | ||
| Wed., 2/6 | Winter Dance Team | NVL Tournament | Away - Woodland HS | 6:00 p.m. | ||
| Thu., 2/7 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/7 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 42-49 | |
| Thu., 2/7 | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Thu., 2/7 | V Girls Gymnastics | SWC Championship | Away [Directions] | 5:00 p.m. | 130.8 | |
| Thu., 2/7 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 7:00 p.m. | L 58-68 | |
| Fri., 2/8 | JV Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/8 | V Boys Swimming and Diving | Sacred Heart | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Woodland | Home - Seymour HS [Directions] | 7:00 p.m. | W 52-43 | |
| Fri., 2/8 | JV Girls Basketball | Woodland | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Sat., 2/9 | V Boys Ice Hockey | Immaculate | Home - Bennett Rink [Directions] | 1:00 p.m. | W 5-4 (OT) | |
| Sat., 2/9 | V Wrestling | NVL/Berkshire Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 2/9 | V Competitive Cheerleading | Warde Winter Cheer Challenge | Away - Fairfield Warde | TBA | ||
| Mon., 2/11 | V Boys Basketball | Ansonia | Home - Seymour HS [Directions] | 5:00 p.m. | L 64-76 | |
| Mon., 2/11 | V Girls Basketball | WCA | Home - Seymour HS [Directions] | 7:00 p.m. | L 38-53 | |
| Wed., 2/13 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Bennett Rink [Directions] | 6:00 p.m. | L 4-0 | |
| Wed., 2/13 | V Boys Swimming and Diving | Torrington | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Thu., 2/14 | V Boys Basketball | Derby | Home - Seymour HS [Directions] | 7:00 p.m. | W 76-60 | |
| Thu., 2/14 | JV Boys Basketball | Derby | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Thu., 2/14 | V Girls Gymnastics | Jonathan Law, Hamden | Away - Jonathan Law HS Old Gym [Directions] | 6:00 p.m. | 124.65 | |
| Thu., 2/14 | V Girls Gymnastics | Jonathan Law, Hamden | Away [Directions] | Cancelled | Cancelled | |
| Fri., 2/15 | V Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 7:00 p.m. | L 63-95 | |
| Fri., 2/15 | JV Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 5:15 p.m. | ||
| Fri., 2/15 | FR Boys Basketball | WCA | Away - Waterbury Career Academy [Directions] | 1:30 p.m. | ||
| Fri., 2/15 | V Boys Swimming and Diving | Oxford | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Fri., 2/15 | V Wrestling | Class S Championship | Away - TBA | 5:30 p.m. | ||
| Sat., 2/16 | V Boys Ice Hockey | Glastonbury | Home - Bennett Rink [Directions] | 1:00 p.m. | L 1-5 | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | Class S Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 2/16 | V Competitive Cheerleading | NVL Championships | Away - Crosby HS | TBA | ||
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/18 | V Girls Gymnastics | Newtown, Nonnewaug, Pomperaug | Away - Kinetic Kids [Directions] | 1:00 p.m. | 134.2 | |
| Thu., 2/21 | V Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 7:00 p.m. | W 66-63 | |
| Thu., 2/21 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/21 | FR Boys Basketball | Kaynor Tech | Away - Kaynor Tech Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/22 | V Wrestling | State Open Championship | Away - TBA | 5:00 p.m. | ||
| Sat., 2/23 | V Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | 10:00 a.m. | L 3-4(OT) | |
| Sat., 2/23 | V Wrestling | State Open Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 2/23 | V Competitive Cheerleading | NECA | Away | TBA | ||
| Sat., 2/23 | Winter Dance Team | State Tournament | Away - Hamden HS | TBA | ||
| Mon., 2/25 | V Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 4-6 | |
| Tue., 2/26 | V Boys Swimming and Diving | NVL Trials | Away - Kennedy HS | 4:30 p.m. | ||
| Tue., 2/26 | V Girls Basketball | Jonathan Law | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | 7:00 p.m. | L 54-66 | |
| Fri., 3/1 | V Boys Swimming and Diving | NVL Finals | Away - Kennedy HS | 4:30 p.m. | ||
| Fri., 3/1 | V Wrestling | New England Championship | Away - TBA | 5:00 a.m. | ||
| Fri., 3/1 | V Competitive Cheerleading | State Championships | Away | TBA | ||
| Fri., 3/1 | V Girls Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/2 | V Wrestling | State Open Championship | Away - TBA | 10:00 a.m. | ||
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Thu., 3/7 | V Girls Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Cheshire Community Pool [Directions] | 3:00 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | ||
| Mon., 3/11 | V Girls Basketball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | ||
| Sat., 3/16 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sun., 3/17 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sun., 3/24 | V Softball | East Haven (Scrim.) | Away [Directions] | 2:00 p.m. | ||
| Tue., 3/26 | V Baseball | Lewis Mills (Scrim.) | Home - French Park [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Baseball | Trumbull (Scrim.) | Away - Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | JV Baseball | Trumbull (Scrim.) | Home - French Park [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Softball | Pomperaug (Scrim.) | Away - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 3/30 | V Softball | Cheshire (Scrim.) | Away - Cheshire High softball field [Directions] | 2:00 p.m. | ||
| Sat., 3/30 | JV Girls Tennis | Sacred Heart | Away | 11:00 a.m. | ||
| Mon., 4/1 | V Baseball | Pomperaug | Away - PHS Baseball Field [Directions] | 4:00 p.m. | W 9-4 | |
| Mon., 4/1 | V Softball | Trumbull | Home - Seymour HS [Directions] | 4:15 p.m. | L 4-5 | |
| Tue., 4/2 | V Boys Outdoor Track | WCA, Wilby | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | Seymour vs Wilby 80-66 Seymour Vs WCA 82-65 Wilby vs WCA | |
| Tue., 4/2 | V Girls Outdoor Track | WCA, Wilby | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | Seymour Vs Wilby 120-22 Seymour Vs WCA 106-41 Wilby Vs WCA TBA | |
| Tue., 4/2 | V Softball | WCA | Home - Seymour HS [Directions] | 3:45 p.m. | W 20-2 | |
| Wed., 4/3 | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:45 p.m. | ||
| Wed., 4/3 | JV Softball | WCA | Home - Seymour HS [Directions] | 4:30 p.m. | W 15-0 | |
| Wed., 4/3 | V Girls Tennis | Holy Cross | Home - Seymour HS [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 4/4 | V Softball | Waterford | Home - Seymour HS [Directions] | 4:30 p.m. | W 10-1 | |
| Thu., 4/4 | V Girls Tennis | St. Paul Catholic | Away - Page Park, Bristol [Directions] | 4:30 p.m. | L 2-5 | |
| Fri., 4/5 | V Baseball | Wilby | Home - French Park [Directions] | 3:45 p.m. | W 10-0 | |
| Sat., 4/6 | JV Baseball | Ansonia | Away [Directions] | Cancelled | Cancelled | |
| Mon., 4/8 | V Baseball | Crosby | Away - Washington Park [Directions] | 4:00 p.m. | W 10-0 | |
| Mon., 4/8 | V Softball | St. Paul Catholic | Home - Seymour HS [Directions] | 4:15 p.m. | W 10-9 | |
| Tue., 4/9 | V Boys Golf | Watertown | Away - Crestbrook Park [Directions] | 2:30 p.m. | watertown 197 seymour 211 Guillette 44 thomas 53 mcCormick 54 Cebik 65 | |
| Tue., 4/9 | V Girls Tennis | Ansonia | Home - Seymour HS [Directions] | 3:15 p.m. | W 6-0 | |
| Wed., 4/10 | V Baseball | Naugatuck | Home - French Park [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 4/10 | V Boys Outdoor Track | Derby, Sacred Heart | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Girls Outdoor Track | Derby, Sacred Heart | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/10 | V Girls Tennis | Crosby | Away - Crosby HS [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/11 | JV Baseball | Naugatuck | Home - French Park [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | 2:30 p.m. | Seymour 208 Naugatuck 245 Guillette 42 thomas 52 mccormick 55 Dejarnette 59 | |
| Thu., 4/11 | V Softball | Ansonia | Away - Ansonia HS [Directions] | 3:30 p.m. | W 19-1 | |
| Fri., 4/12 | V Baseball | Ansonia | Home - French Park [Directions] | 3:30 p.m. | L 4-7 | |
| Fri., 4/12 | V Boys Outdoor Track | Holy Cross, Oxford | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Fri., 4/12 | V Girls Outdoor Track | Holy Cross, Oxford | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Sat., 4/13 | JV Baseball | Ansonia | Home - French Park [Directions] | Cancelled | Cancelled | |
| Tue., 4/16 | V Boys Golf | St. Paul Catholic | Away - Chippanee Golf Club [Directions] | 3:00 p.m. | St paul 175- seymour 214 Guillette 47 Thomas 56 Mccormick 54 DeJarnette 57 | |
| Tue., 4/16 | V Softball | Derby | Home - Seymour HS [Directions] | 5:00 p.m. | W 17-0 | |
| Wed., 4/17 | V Baseball | Torrington | Away - Fuessenich Pk [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 4/17 | V Softball | Torrington | Away - Torrington HS [Directions] | 11:00 a.m. | W 19-5 | |
| Wed., 4/17 | V Girls Tennis | Wilby | Home - Seymour HS [Directions] | 11:00 a.m. | W 7-0 | |
| Thu., 4/18 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | 11:00 a.m. | L 2-12 | |
| Thu., 4/18 | JV Baseball | Torrington | Away - Torrington HS [Directions] | 10:00 a.m. | ||
| Thu., 4/18 | V Boys Golf | Torrington | Home - Oxford Greens [Directions] | 2:30 p.m. | Torrington 201 Seymour 206 Guillette 47 Thomas 53 Mccormick 53 DeJarnette 53 | |
| Thu., 4/18 | JV Softball | Amity | Away - Center Field - Woodbridge [Directions] | 10:00 a.m. | L 2-3 | |
| Thu., 4/18 | V Girls Tennis | Woodland | Away - Woodland HS Tennis courts [Directions] | 11:00 a.m. | L 5-2 | |
| Fri., 4/19 | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | 11:00 a.m. | ||
| Fri., 4/19 | JV Softball | Oxford | Home - Seymour HS [Directions] | 10:00 a.m. | W 11-3 | |
| Tue., 4/23 | V Baseball | Sacred Heart | Home - French Park [Directions] | 3:30 p.m. | W 6-2 | |
| Tue., 4/23 | V Boys Outdoor Track | Wolcott, Crosby | Away - Wolcott HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Wolcott, Crosby | Away [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Softball | Sacred Heart | Away - Municipal Stadium - Joan Joyce Field | 3:45 p.m. | W 21-3 | |
| Tue., 4/23 | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | 3:30 p.m. | W 7-0 | |
| Wed., 4/24 | V Baseball | Woodland | Home - French Park [Directions] | 3:30 p.m. | L 11-0 | |
| Wed., 4/24 | V Boys Golf | Sacred Heart | Away - East Mountain Golf Course | 2:30 p.m. | seymour 196 sacred heart 226 Guillette 39, thomas 52,DeJarnette 50, McCormick 55 | |
| Wed., 4/24 | V Softball | Woodland | Away - Beacon Falls Rec - Pent Field [Directions] | 3:30 p.m. | W 3-1 | |
| Thu., 4/25 | JV Baseball | Woodland | Home - French Park [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | V Boys Golf | Waterbury Coop | Home - Oxford Greens [Directions] | 2:30 p.m. | seymour 186 kennedy 285 Guillette 39,Thomas 43,McCormick 49, Scott 55 | |
| Thu., 4/25 | V Boys Golf | Wilby | Home - Oxford Greens [Directions] | 2:30 p.m. | seymour 186-wilby 270 Guillette 39 thomas,43,mccormick 49,scott 55. | |
| Thu., 4/25 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:15 p.m. | L 3-4 | |
| Thu., 4/25 | V Girls Tennis | St. Paul Catholic | Home - Seymour HS [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/27 | V Boys Outdoor Track | Bristol Invitational | Away | 10:00 a.m. | ||
| Sat., 4/27 | V Girls Outdoor Track | Bristol Central Invitational | Away | 10:00 a.m. | ||
| Sat., 4/27 | V Girls Tennis | Wolcott | Away - Wolcott HS [Directions] | 10:00 a.m. | L 3-4 | |
| Mon., 4/29 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | 3:45 p.m. | L 2-11 | |
| Mon., 4/29 | V Softball | Wolcott | Home - Seymour HS [Directions] | 6:30 p.m. | W 6-5 | |
| Mon., 4/29 | JV Softball | Wolcott | Home - Bungay School [Directions] | 3:30 p.m. | W 8-1 | |
| Tue., 4/30 | V Baseball | St. Paul Catholic | Home - French Park [Directions] | 4:00 p.m. | L 8-7 | |
| Tue., 4/30 | V Boys Outdoor Track | St. Paul Catholic, Woodland | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | St. Paul Catholic, Woodland | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Baseball | Kennedy | Away - Waterville Park [Directions] | 3:30 p.m. | W 9-3 | |
| Wed., 5/1 | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Boys Golf | Woodland | Away - Oxford Greens [Directions] | 2:30 p.m. | Seymour 200-Woodland 228 Guillette 47,Thomas 47,Scott 50,DeJarnette 56 | |
| Wed., 5/1 | V Softball | Kennedy | Home - Seymour HS [Directions] | 3:45 p.m. | W 17-0 | |
| Wed., 5/1 | V Girls Tennis | Sacred Heart | Home - Seymour HS [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 5/2 | V Boys Golf | Woodland Invitational | Away | 8:00 a.m. | ||
| Thu., 5/2 | V Softball | Oxford | Home - Seymour HS [Directions] | 6:00 p.m. | L 0-8 | |
| Thu., 5/2 | JV Softball | Kennedy | Home - Seymour HS [Directions] | 3:45 p.m. | W 21-0 | |
| Fri., 5/3 | V Baseball | Derby | Home - French Park [Directions] | 3:30 p.m. | W 14-4 | |
| Sat., 5/4 | V Boys Outdoor Track | Coginchaug Invitational | Away | 10:00 a.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Coginchaug Invitational | Away | 10:00 a.m. | ||
| Sat., 5/4 | JV Softball | Naugatuck | Away - Naugatuck HS [Directions] | 12:00 p.m. | W 11-0 | |
| Mon., 5/6 | V Baseball | Oxford | Home - French Park [Directions] | 3:30 p.m. | L 9-11 | |
| Mon., 5/6 | V Boys Golf | Wolcott | Home - Oxford Greens [Directions] | 2:30 p.m. | wolcott 221-seymour 248 Thomas 44, Cebik 63, DeJarnette 59, Adamo 82 | |
| Mon., 5/6 | V Softball | Oxford | Away - OHS Softball Field [Directions] | 3:45 p.m. | W 8-7 | |
| Mon., 5/6 | V Girls Tennis | Woodland | Home - Seymour HS [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 5/7 | V Baseball | Watertown | Away - Deland Field [Directions] | 3:45 p.m. | L 3-6 | |
| Tue., 5/7 | JV Baseball | Oxford | Home - French Park [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Watertown, Naugatuck | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Watertown, Naugatuck | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | JV Softball | Oxford | Away - OHS Softball Field [Directions] | 3:45 p.m. | W 11-4 | |
| Tue., 5/7 | V Girls Tennis | Watertown | Home - Seymour HS [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 5/8 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:45 p.m. | W 4-1 | |
| Wed., 5/8 | V Boys Golf | Stigbery | Away [Directions] | TBA | ||
| Wed., 5/8 | V Softball | Ansonia | Home - Seymour HS [Directions] | 3:30 p.m. | W 15-0 | |
| Wed., 5/8 | V Girls Tennis | Naugatuck | Home - Seymour HS [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 5/9 | JV Baseball | Ansonia | Away [Directions] | Cancelled | Cancelled | |
| Thu., 5/9 | V Boys Golf | Naugatuck | Away - Hop Brook Golf Course [Directions] | 2:30 p.m. | seymour 193- naugatuck 221 Guillette 39, Thomas 47, McCormick 53 DeJarnette 54 | |
| Thu., 5/9 | V Softball | Watertown | Home - Seymour HS [Directions] | 7:00 p.m. | W 12-1 | |
| Thu., 5/9 | JV Softball | Woodland | Away - Woodland Softball Field [Directions] | 3:30 p.m. | W 17-9 | |
| Thu., 5/9 | V Girls Tennis | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 5/10 | JV Softball | Watertown | Home - Seymour HS [Directions] | 3:30 p.m. | ||
| Sat., 5/11 | JV Baseball | Watertown | Away - Deland Field [Directions] | 3:30 p.m. | ||
| Sat., 5/11 | V Boys Outdoor Track | East Hartford Invitational | Away | 9:00 a.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | East Hartford Invitational | Away | 9:00 a.m. | ||
| Sat., 5/11 | JV Softball | Naugatuck | Away - Naugatuck HS [Directions] | 1:00 p.m. | W 8-1 | |
| Sat., 5/11 | JV Softball | Watertown | Home - Naugatuck HS [Directions] | 2:30 p.m. | W 9-3 | |
| Sat., 5/11 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | 11:00 a.m. | W 7-0 | |
| Tue., 5/14 | V Softball | Derby | Away - Seymour HS [Directions] | 5:00 p.m. | W 11-0 | |
| Wed., 5/15 | V Baseball | Newtown | Home - French Park [Directions] | 4:30 p.m. | W 8-5 | |
| Wed., 5/15 | V Boys Golf | Wolcott | Away - Farmingbury Country Club [Directions] | 2:30 p.m. | Seymour 194 - Wolcott 207 Guillette 43 Thomas44 Mccormick 53, DeJarnette 54 | |
| Wed., 5/15 | V Softball | Woodland | Home - Seymour HS [Directions] | 6:00 p.m. | W 5-2 | |
| Thu., 5/16 | V Baseball | Derby | Away - Naugatuck HS [Directions] | 6:30 p.m. | W 17-7 | |
| Thu., 5/16 | V Boys Golf | Torrington | Away - Torrington Country Club [Directions] | 2:30 p.m. | Torrington 177-Seymour 205. Guillette 40,Thomas 53,McCormick 54,DeJarnette 58 | |
| Thu., 5/16 | V Softball | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | L 2-3 | |
| Fri., 5/17 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:30 p.m. | L 0-8 | |
| Fri., 5/17 | JV Baseball | Holy Cross | Home - French Park [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | JV Softball | Holy Cross | Away - Lower Murray Park [Directions] | 3:45 p.m. | W 16-0 | |
| Sat., 5/18 | V Baseball | Holy Cross | Home - French Park [Directions] | 1:00 p.m. | L 9-4 | |
| Mon., 5/20 | V Boys Golf | St. Paul Catholic | Home - Oxford Greens [Directions] | 2:30 p.m. | st paul 185 seymour 210 Guillette 46, Thomas 46, McCormick 58, Scott 60. | |
| Mon., 5/20 | V Girls Tennis | NVL Individuals | Away [Directions] | 12:00 p.m. | ||
| Tue., 5/21 | V Boys Golf | Holy Cross | Home - Oxford Greens [Directions] | 2:30 p.m. | holy cross 175- seymour 235 Guillette 50, Thomas 58, McCormick 63, DeJarnette 64 | |
| Tue., 5/21 | V Boys Outdoor Track | NVL Tournament - Torrington | Away | 1:30 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | NVL Tournament - Torrington | Away | 1:30 p.m. | ||
| Tue., 5/21 | V Softball | Woodland | Home [Directions] | 6:00 p.m. | W 4-3 | |
| Wed., 5/22 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | 2:30 p.m. | watertown 194 Seymour 208 Guillette 40, Thomas 55, Scott 57, Cebik 56. | |
| Wed., 5/22 | V Boys Outdoor Track | JV NVL Tournament | Away [Directions] | 3:30 p.m. | ||
| Wed., 5/22 | V Softball | St. Paul Catholic | Away - Seymour HS [Directions] | 6:15 p.m. | ||
| Thu., 5/23 | V Softball | Oxford | Away [Directions] | 5:00 p.m. | ||
| Sat., 5/25 | V Baseball | CIAC Tourney Qualifying Round | Away - Higher Seed | TBA | ||
| Sat., 5/25 | V Softball | CIAC Tourney Qualifying Round | Away - Higher Seed | TBA | ||
| Tue., 5/28 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | V Boys Outdoor Track | State Meet | Away | 3:00 p.m. | ||
| Tue., 5/28 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | V Girls Outdoor Track | State Meet - New Britain | Away | 3:00 p.m. | ||
| Tue., 5/28 | V Softball | CIAC Tourney 1st Round | Home - Higher Seed [Directions] | 4:00 p.m. | ||
| Wed., 5/29 | V Baseball | Nonnewaug | Away - Nonnewaug HS [Directions] | 2:30 p.m. | ||
| Wed., 5/29 | V Softball | Montville | Home - Seymour HS [Directions] | 3:00 p.m. | W 5-4 | |
| Thu., 5/30 | V Baseball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | Cancelled | |
| Thu., 5/30 | V Boys Golf | NVL Tournament | Away [Directions] | 8:30 a.m. | ||
| Fri., 5/31 | V Softball | Jonathan Law | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Sat., 6/1 | V Baseball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | |
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | ||
| Tue., 6/4 | V Baseball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | |
| Tue., 6/4 | V Boys Golf | CIAC Div. III Championship | Away - Fairview Farms - Harwinton [Directions] | 8:30 a.m. | ||
| Tue., 6/4 | V Softball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Sat., 6/8 | V Baseball | CIAC Tourney Final | Away - Palmer Field, Middletown [Directions] | Cancelled | Cancelled | |
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Softball | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||