| Seymour 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 539 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Baseball | East Haven (Scrim.) | Home - French Park [Directions] | TBA | ||
| TBA | JV Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| TBA | JV Baseball | Holy Cross | Home - French Park [Directions] | TBA | ||
| TBA | JV Baseball | Ansonia | Home - French Park [Directions] | TBA | ||
| TBA | JV Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Baseball | Sacred Heart | Away - Fulton Park | TBA | ||
| TBA | JV Baseball | Wolcott | Home - French Park [Directions] | TBA | ||
| TBA | JV Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | TBA | ||
| TBA | FR Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | ||
| TBA | JV Football | Naugatuck | Away - Naugatuck HS [Directions] | TBA | ||
| TBA | JV Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | TBA | ||
| TBA | JV Boys Soccer | Wilby | Home - Seymour High Lower Field [Directions] | TBA | ||
| TBA | JV Boys Soccer | Watertown | Away - Veterans Park [Directions] | TBA | ||
| TBA | V Girls Basketball | Shelton (Scrim.) | Home - Seymour HS [Directions] | TBA | ||
| TBA | FR Girls Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | TBA | ||
| TBA | FR Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | Cancelled | Cancelled | |
| TBA | JV Softball | Trumbull (Scrim.) | Home - Bungay School [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Watertown | Home - Bungay School [Directions] | TBA | Double Header | |
| TBA | JV Softball | Cheshire (Scrim.) | Home - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | WCA | Home - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | St. Paul Catholic | Home - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | Sacred Heart | Home - Seymour HS [Directions] | TBA | ||
| TBA | JV Softball | Woodland | Away - Woodland Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Wolcott | Home - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | Watertown | Home - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | Oxford | Home - Bungay School [Directions] | TBA | ||
| TBA | JV Softball | Naugatuck | Away - Naugatuck HS [Directions] | TBA | ||
| Sat., 8/26 | V Football | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 1:00 p.m. | ||
| Mon., 8/28 | V Football | Hamden (Scrim.) | Away - HHS Turf Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Shepaug Valley (Scrim.) | Home - Seymour HS Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 9/1 | V Football | Rocky Hill (Scrim.) | Away - Rocky Hill HS [Directions] | 7:00 p.m. | ||
| Fri., 9/1 | V Boys Soccer | Thomaston (Scrim.) | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 9/1 | V Girls Volleyball | Pomperaug (Scrim.) | Away - PHS Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 9/2 | V Girls Soccer | Shelton (Scrim.) | Away [Directions] | 8:00 a.m. | ||
| Tue., 9/5 | V Boys Soccer | Amity (Scrim.) | Away - Amity HS [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | V Girls Soccer | Wilbur Cross (Scrim.) | Home - Seymour HS Turf Field [Directions] | 2:45 p.m. | ||
| Wed., 9/6 | FR Football | Crosby (Scrim.) | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 3:30 p.m. | ||
| Wed., 9/6 | V Girls Volleyball | Newtown (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Wed., 9/6 | V Girls Volleyball | Newtown (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Fri., 9/8 | V Football | Torrington | Home - Seymour HS Turf Field [Directions] | 7:00 p.m. | W 49-8 | |
| Fri., 9/8 | V Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | W 1-0 | |
| Fri., 9/8 | V Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/8 | JV Girls Volleyball | WCA | Away - Waterbury Career Academy [Directions] | 3:30 p.m. | W 2-0 | |
| Sat., 9/9 | JV Football | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 11:00 a.m. | ||
| Sat., 9/9 | JV Boys Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 9/9 | V Girls Soccer | Woodland | Home - Seymour HS Turf Field [Directions] | 11:00 a.m. | L 1-4 | |
| Mon., 9/11 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | L 0-4 | |
| Tue., 9/12 | V Boys Cross Country | Naugatuck, Kennedy, Woodland | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Naugatuck, Kennedy, Woodland | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Soccer | Naugatuck | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | L 2-4 | |
| Tue., 9/12 | V Girls Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | Seymour 80 Holy Cross 52 | |
| Tue., 9/12 | V Girls Volleyball | Oxford | Home - Seymour HS [Directions] | 5:30 p.m. | W 3-2 | |
| Tue., 9/12 | JV Girls Volleyball | Oxford | Home - Seymour HS [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 9/13 | FR Football | Naugatuck | Home - Seymour High Lower Field [Directions] | 3:30 p.m. | ||
| Wed., 9/13 | JV Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Sacred Heart | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 1-0 | |
| Thu., 9/14 | V Girls Soccer | Sacred Heart | Away - Municipal Stadium | 6:30 p.m. | L 3-4 | |
| Thu., 9/14 | V Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:15 p.m. | W 3-2 | |
| Thu., 9/14 | JV Girls Volleyball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 9/15 | V Football | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 12-31 | |
| Fri., 9/15 | JV Boys Soccer | Sacred Heart | Home - Seymour HS Turf Field [Directions] | 3:30 p.m. | ||
| Fri., 9/15 | V Girls Swimming and Diving | Oxford | Home - Seymour HS [Directions] | 4:00 p.m. | Seymour 90 Oxford 78 | |
| Fri., 9/15 | V Girls Volleyball | Wilby | Home - Seymour HS [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/15 | JV Girls Volleyball | Wilby | Home - Seymour HS [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/16 | V Boys Cross Country | Wilton | Home [Directions] | 9:30 a.m. | ||
| Sat., 9/16 | JV Football | Naugatuck | Home - Seymour HS Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/16 | V Girls Cross Country | Wilton | Home [Directions] | 9:30 a.m. | ||
| Mon., 9/18 | V Girls Soccer | Oxford | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | L 2-4 | |
| Tue., 9/19 | V Boys Cross Country | Wolcott, Watertown, Sacred Heart | Away - Montoe Park [Directions] | 3:30 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Oxford | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 2-1 | |
| Tue., 9/19 | V Girls Cross Country | Wolcott, Watertown, Sacred Heart | Away - Montoe Park [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Girls Swimming and Diving | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | Seymour 77 Kennedy 57 | |
| Tue., 9/19 | V Girls Volleyball | Crosby | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/19 | JV Girls Volleyball | Crosby | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 9/20 | JV Boys Soccer | Oxford | Home - Seymour High Lower Field [Directions] | 3:45 p.m. | ||
| Wed., 9/20 | V Girls Soccer | Ansonia | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 9-0 | |
| Thu., 9/21 | V Girls Soccer | Torrington | Away - Torrington HS [Directions] | 6:30 p.m. | W 2-1 | |
| Fri., 9/22 | V Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | W 3-1 | |
| Fri., 9/22 | V Girls Swimming and Diving | Woodland | Home - Seymour HS [Directions] | 4:00 p.m. | Seymour 94 Woodland 71 | |
| Fri., 9/22 | V Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/22 | JV Girls Volleyball | Torrington | Away - Torrington HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 9/23 | JV Boys Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 10:30 a.m. | ||
| Tue., 9/26 | V Boys Cross Country | Derby, Ansonia, WCA | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Kennedy | Away - Municipal Stadium [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 9/26 | V Girls Cross Country | Derby, Ansonia, WCA | Away - Derby -Ryan Athletic Complex- Deflippo Field [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | JV Girls Soccer | Wolcott | Away - Wolcott HS, Lower Soccer Field [Directions] | 4:15 p.m. | ||
| Tue., 9/26 | V Girls Swimming and Diving | Watertown | Home - Seymour HS [Directions] | 5:00 p.m. | Seymour 83 Watertown 79 | |
| Tue., 9/26 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/26 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 9/27 | FR Football | Berlin | Away - Sage Park - Scalise Field [Directions] | 3:45 p.m. | ||
| Wed., 9/27 | FR Football | Naugatuck | Away - Naugatuck HS [Directions] | Cancelled | Cancelled | |
| Wed., 9/27 | JV Boys Soccer | Kennedy | Away - West Side MS [Directions] | 3:45 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Lauralton Hall | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/28 | V Football | Sacred Heart | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 49-6 | |
| Thu., 9/28 | V Girls Volleyball | East Haven | Home - Seymour HS [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/28 | JV Girls Volleyball | East Haven | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 9/29 | V Boys Soccer | St. Paul Catholic | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 7-1 | |
| Fri., 9/29 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | L 2-4 | |
| Fri., 9/29 | V Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/29 | JV Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 9/30 | JV Boys Soccer | St. Paul Catholic | Home - Seymour HS Turf Field [Directions] | 11:00 a.m. | ||
| Tue., 10/3 | V Boys Cross Country | Holy Cross, Torrington, Wilby | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Boys Soccer | Torrington | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 2-0 | |
| Tue., 10/3 | V Girls Cross Country | Holy Cross, Torrington, Wilby | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | JV Girls Soccer | Naugatuck | Home - Seymour HS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | Seymour 98 Sacred Heart 77 | |
| Tue., 10/3 | V Girls Volleyball | Ansonia | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-2 | |
| Tue., 10/3 | JV Girls Volleyball | Ansonia | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/4 | JV Boys Soccer | Torrington | Home - Seymour High Lower Field [Directions] | 3:45 p.m. | ||
| Wed., 10/4 | V Girls Soccer | Torrington | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 1-0 | |
| Thu., 10/5 | FR Football | Wolcott | Home - Seymour High Lower Field [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | V Football | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:30 p.m. | W 63-26 | |
| Fri., 10/6 | V Boys Soccer | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 10/6 | V Girls Soccer | Derby | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 7-0 | |
| Fri., 10/6 | V Girls Swimming and Diving | Naugatuck | Home - Seymour HS [Directions] | 4:00 p.m. | Seymour 83 Naugatuck 74 | |
| Fri., 10/6 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/6 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/7 | JV Football | Wolcott | Home - Seymour HS Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | JV Boys Soccer | Crosby | Away - Crosby HS - Jimmy Lee Stadium (turf) [Directions] | 11:00 a.m. | ||
| Sat., 10/7 | JV Girls Soccer | Derby | Away - Derby -Witek Park [Directions] | 1:30 p.m. | ||
| Tue., 10/10 | V Boys Cross Country | Crosby, Oxford, St. Paul Catholic | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | T 2-2 | |
| Tue., 10/10 | V Girls Cross Country | Crosby, Oxford, St. Paul Catholic | Home - Seymour H.S. [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Girls Soccer | Holy Cross | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | T 2-2 | |
| Tue., 10/10 | V Girls Volleyball | Watertown | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/10 | JV Girls Volleyball | Watertown | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Wed., 10/11 | JV Boys Soccer | Holy Cross | Away - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | JV Girls Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | 4:30 p.m. | ||
| Thu., 10/12 | V Girls Volleyball | Woodland | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/12 | JV Girls Volleyball | Woodland | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 10/13 | V Boys Soccer | Wilby | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 5-0 | |
| Fri., 10/13 | V Girls Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | T 3-3 | |
| Fri., 10/13 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby H.S. [Directions] | 4:00 p.m. | Seymour 86 Wilby/Kaynor Tech 58 | |
| Fri., 10/13 | V Girls Volleyball | Wolcott | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/13 | JV Girls Volleyball | Wolcott | Home - Seymour HS [Directions] | 4:45 p.m. | L 0-2 | |
| Tue., 10/17 | V Boys Soccer | Wolcott | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 6-0 | |
| Tue., 10/17 | V Girls Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 10/17 | V Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/17 | JV Girls Volleyball | Ansonia | Away - Ansonia HS [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 10/18 | V Boys Cross Country | NVL Championship | Away - Veterans Park | TBA | ||
| Wed., 10/18 | FR Football | Kennedy | Home - Seymour High Lower Field [Directions] | 3:30 p.m. | ||
| Wed., 10/18 | JV Boys Soccer | Wolcott | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | ||
| Wed., 10/18 | V Girls Cross Country | NVL Championship | Away - Veterans Park | TBA | ||
| Wed., 10/18 | V Girls Swimming and Diving | Torrington | Home - Seymour HS [Directions] | 4:00 p.m. | Seymour 84 Torrington 76 | |
| Thu., 10/19 | V Football | Kennedy | Away - Municipal Stadium [Directions] | 3:30 p.m. | W 49-14 | |
| Thu., 10/19 | V Girls Volleyball | Naugatuck | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/19 | JV Girls Volleyball | Naugatuck | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Fri., 10/20 | V Boys Soccer | Derby | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 9-0 | |
| Fri., 10/20 | V Girls Soccer | Derby | Away - Derby -Witek Park [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 10/20 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Seymour HS [Directions] | 6:30 p.m. | Seymour 88 St. Paul 70 | |
| Fri., 10/20 | V Girls Volleyball | St. Paul Catholic | Home - Seymour HS [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/20 | JV Girls Volleyball | St. Paul Catholic | Home - Seymour HS [Directions] | 4:45 p.m. | W 2-0 | |
| Sat., 10/21 | JV Boys Soccer | Derby | Home - Seymour HS Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/23 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | L 0-4 | |
| Mon., 10/23 | V Girls Soccer | Watertown | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | L 1-4 | |
| Wed., 10/25 | FR Football | Ansonia | Away - Nolan Field, Ansonia [Directions] | 6:00 p.m. | ||
| Wed., 10/25 | V Boys Soccer | WCA | Home - Seymour HS Turf Field [Directions] | 6:30 p.m. | W 6-0 | |
| Wed., 10/25 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Wed., 10/25 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 10/26 | V Football | Ansonia | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | L 6-61 | |
| Thu., 10/26 | JV Boys Soccer | WCA | Home - Seymour High Lower Field [Directions] | 3:45 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Ansonia | Away - Chargers Field on Prindle Avenue [Directions] | 3:30 p.m. | W 3-0 | |
| Fri., 10/27 | V Girls Swimming and Diving | St. Joseph | Home - Seymour HS [Directions] | 4:00 p.m. | Seymour 83 St. Joseph 72 | |
| Sat., 10/28 | JV Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Sat., 10/28 | V Boys Soccer | Sacred Heart | Home - Seymour HS Turf Field [Directions] | 1:00 p.m. | W 3-0 | |
| Sat., 10/28 | V Girls Soccer | Woodland | Away - Woodland Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/28 | V Girls Volleyball | Ansonia | Home - Seymour HS [Directions] | 11:00 a.m. | W 3-0 | |
| Mon., 10/30 | V Girls Volleyball | Wolcott | Away - Kennedy HS [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/31 | V Boys Soccer | Watertown | Away - Municipal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | NVL Trials | Away - Kennedy HS | 4:00 p.m. | ||
| Thu., 11/2 | V Girls Volleyball | Torrington | Away - Crosby HS [Directions] | 7:00 p.m. | ||
| Fri., 11/3 | V Football | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | W 49-12 | |
| Fri., 11/3 | V Girls Swimming and Diving | NVL Finals | Away - Kennedy HS | 4:30 p.m. | ||
| Sat., 11/4 | FM Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 10:00 a.m. | ||
| Mon., 11/6 | V Boys Soccer | Plainville | Home - Seymour HS Turf Field [Directions] | 2:00 p.m. | ||
| Tue., 11/7 | FM Football | Nonnewaug | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 11/7 | V Girls Soccer | North Branford/Hale Ray | Away [Directions] | 6:00 p.m. | ||
| Wed., 11/8 | V Girls Volleyball | Plainfield | Home - Seymour HS [Directions] | 5:00 p.m. | ||
| Fri., 11/10 | V Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | W 38-19 | |
| Fri., 11/10 | V Girls Volleyball | Nonnewaug | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Sat., 11/11 | JV Football | Ansonia | Home - Seymour HS Turf Field [Directions] | Cancelled | Cancelled | |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 2:00 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Tue., 11/14 | V Girls Volleyball | State Semi-Finals | Away - Jonathon Law HS | 7:00 p.m. | ||
| Wed., 11/15 | FR Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | ||
| Thu., 11/16 | V Football | Derby | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 63-14 | |
| Sat., 11/18 | JV Football | Woodland | Away - Woodland Football Field [Directions] | 11:00 a.m. | ||
| Sat., 11/18 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Wed., 11/22 | V Football | Woodland | Home - Seymour HS Turf Field [Directions] | 6:00 p.m. | W 56-8 | |
| Tue., 11/28 | V Football | Ansonia | Away [Directions] | 6:30 p.m. | ||
| Sat., 12/2 | V Girls Basketball | Amity Jamboree | Away - Amity HS | TBA | ||
| Tue., 12/5 | V Girls Basketball | Joel Barlow (Scrim.) | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 12/6 | V Boys Ice Hockey | Glastonbury (Scrim.) | Home - Bennett Rink [Directions] | 6:30 p.m. | ||
| Thu., 12/7 | V Girls Basketball | Masuk (Scrim.) | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | ||
| Fri., 12/8 | V Boys Basketball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 12/8 | V Boys Ice Hockey | St. Lukes (Scrim.) | Home - Bennett Rink [Directions] | 4:00 p.m. | ||
| Mon., 12/11 | V Boys Basketball | Amity (Scrim.) | Home - Seymour HS [Directions] | 3:30 p.m. | ||
| Tue., 12/12 | V Girls Basketball | Torrington | Away - Torrington HS [Directions] | 7:00 p.m. | W 50-19 | |
| Tue., 12/12 | JV Girls Basketball | Torrington | Away - Torrington HS [Directions] | 5:15 p.m. | ||
| Tue., 12/12 | FR Girls Basketball | Torrington | Away - Torrington HS [Directions] | 3:45 p.m. | ||
| Wed., 12/13 | V Boys Basketball | Bullard Havens Tech (Scrim.) | Away - BHT GYM [Directions] | 5:30 p.m. | ||
| Wed., 12/13 | V Boys Ice Hockey | Jamboree | Home - Bennett Rink [Directions] | 6:00 p.m. | ||
| Sat., 12/16 | V Wrestling | Derby Invitational | Home - Derby HS Gymnasium [Directions] | 9:00 a.m. | ||
| Mon., 12/18 | V Boys Indoor Track | Relay Rust Buster Invitational | Away - SCSU | 5:00 p.m. | ||
| Mon., 12/18 | V Girls Basketball | Wilby | Home - Seymour HS [Directions] | 7:00 p.m. | W 74-39 | |
| Mon., 12/18 | JV Girls Basketball | Wilby | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Mon., 12/18 | V Girls Indoor Track | Relay Rust Buster Invitational | Away - SCSU | 5:00 p.m. | ||
| Tue., 12/19 | V Boys Basketball | Holy Cross | Home - Seymour HS [Directions] | 7:00 p.m. | L 62-93 | |
| Tue., 12/19 | JV Boys Basketball | Holy Cross | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 12/19 | FR Boys Basketball | Holy Cross | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 12/19 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | Loss - Sacred Heart 91, Seymour 81 | |
| Tue., 12/19 | V Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 7:00 p.m. | L 43-58 | |
| Tue., 12/19 | JV Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 5:15 p.m. | ||
| Tue., 12/19 | FR Girls Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 3:45 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Greenwich | Home - Bennett Rink [Directions] | 6:30 p.m. | L 5-2 | |
| Wed., 12/20 | V Wrestling | Thomaston | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 12/21 | V Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 7:00 p.m. | W 62-53 | |
| Thu., 12/21 | JV Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/21 | FR Boys Basketball | Woodland | Away - Woodland HS Gym [Directions] | 3:30 p.m. | ||
| Thu., 12/21 | V Girls Basketball | Crosby | Home - Seymour HS [Directions] | 7:00 p.m. | L 43-47 | |
| Thu., 12/21 | JV Girls Basketball | Crosby | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Bennett Rink [Directions] | 1:00 p.m. | L 4-7 | |
| Wed., 12/27 | V Boys Basketball | WCA | Home - Seymour HS [Directions] | 7:00 p.m. | L 68-86 | |
| Wed., 12/27 | JV Boys Basketball | WCA | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 12/27 | FR Boys Basketball | WCA | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 12/27 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 5:30 p.m. | L 2-9 | |
| Wed., 12/27 | V Wrestling | Terryville-Thomaston | Away - New Terryville HS [Directions] | 6:00 p.m. | ||
| Wed., 12/27 | V Girls Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | W 52-43 | |
| Thu., 12/28 | V Boys Indoor Track | Wilton Wright Invitational | Away - SCSU | 12:00 p.m. | ||
| Thu., 12/28 | V Girls Indoor Track | Wilton Wright Invitational | Away - SCSU | 12:00 p.m. | ||
| Fri., 12/29 | V Girls Basketball | Platt Tech | Away - Derby HS [Directions] | 7:00 p.m. | W 46-23 | |
| Sat., 12/30 | V Boys Ice Hockey | St. Joseph | Home - Bennett Rink [Directions] | 1:00 p.m. | W 7-5 | |
| Sat., 12/30 | V Boys Indoor Track | Wintergreen Invitational | Away - SCSU | 9:00 a.m. | ||
| Sat., 12/30 | V Wrestling | Somers, Fairfield Prep | Away - Somers HS [Directions] | 10:00 a.m. | ||
| Sat., 12/30 | V Girls Indoor Track | Wintergreen Invitational | Away - SCSU | 9:00 a.m. | ||
| Wed., 1/3 | V Boys Basketball | Oxford | Home - Seymour HS [Directions] | 7:00 p.m. | W 102-39 | |
| Wed., 1/3 | JV Boys Basketball | Oxford | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Simsbury | Home - Bennett Rink [Directions] | 6:30 p.m. | W 6-3 | |
| Wed., 1/3 | V Wrestling | Northwestern | Away - Northwestern Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 7:00 p.m. | W 56-46 | |
| Sat., 1/6 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:00 p.m. | L 47-73 | |
| Sat., 1/6 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:30 p.m. | ||
| Sat., 1/6 | V Boys Ice Hockey | Guilford | Home - Bennett Rink [Directions] | 1:00 p.m. | L 3-8 | |
| Sat., 1/6 | V Wrestling | Lawless Tournament | Away - Nonnewaug HS | 9:00 a.m. | ||
| Sat., 1/6 | V Girls Gymnastics | Pomperaug Invitational | Away | 10:00 a.m. | 129.6 | |
| Sun., 1/7 | V Boys Indoor Track | James Barber Invitational | Away - SCSU | TBA | ||
| Sun., 1/7 | V Girls Indoor Track | James Barber Invitational | Away - SCSU | TBA | ||
| Tue., 1/9 | V Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 7:00 p.m. | L 59-69 | |
| Tue., 1/9 | JV Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | FR Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 1/9 | V Girls Gymnastics | New Milford, Joel Barlow, Newtown | Away [Directions] | 5:00 p.m. | 127.25 | |
| Wed., 1/10 | V Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 7:00 p.m. | L 70-76 (OT) | |
| Wed., 1/10 | JV Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 5:15 p.m. | ||
| Wed., 1/10 | FR Boys Basketball | Wolcott | Away - John H. Morris Gymnasium, Wolcott HS [Directions] | 3:45 p.m. | ||
| Wed., 1/10 | V Boys Ice Hockey | Amity | Home - Bennett Rink - West Haven [Directions] | 6:30 p.m. | L 1-3 | |
| Wed., 1/10 | V Girls Basketball | Wolcott | Home - Seymour HS [Directions] | 7:00 p.m. | W 60-57 | |
| Wed., 1/10 | JV Girls Basketball | Wolcott | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 1/10 | FR Girls Basketball | Wolcott | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Thu., 1/11 | V Wrestling | Oxford | Home - Derby HS Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | W 62-51 | |
| Fri., 1/12 | JV Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Ansonia | Away - Ansonia HS [Directions] | 3:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Ansonia | Home - Seymour HS [Directions] | 7:00 p.m. | W 64-30 | |
| Fri., 1/12 | JV Girls Basketball | Ansonia | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | East Haven Coop | Home - Bennett Rink [Directions] | 11:30 a.m. | L 1-2(OT) | |
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invitational | Away - Hillhouse HS | TBA | ||
| Sat., 1/13 | Winter Dance Team | Woodland HS | Away | 2:00 p.m. | ||
| Sat., 1/13 | V Girls Indoor Track | SCC Coaches Invitational | Away - Hillhouse HS | TBA | ||
| Mon., 1/15 | V Boys Ice Hockey | Harvey School (NY) | Home - Bennett Rink [Directions] | 4:00 p.m. | T 2-2 (OT) | |
| Tue., 1/16 | V Boys Basketball | Derby | Home - Seymour HS [Directions] | 5:00 p.m. | W 81-75 (OT) | |
| Tue., 1/16 | JV Boys Basketball | Derby | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 1/16 | V Boys Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/16 | V Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 4:00 p.m. | L 61-40 | |
| Wed., 1/17 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | 6:00 p.m. | L 0-8 | |
| Thu., 1/18 | V Wrestling | Gilbert/Torrington | Home - Derby HS Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 7:00 p.m. | L 52-62 | |
| Fri., 1/19 | JV Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Boys Indoor Track | Yale High School Invitational | Away | TBA | ||
| Fri., 1/19 | V Boys Swimming and Diving | Crosby/WCA | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | Holy Cross | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Naugatuck | Home - Seymour HS [Directions] | 7:00 p.m. | W 53-50 | |
| Fri., 1/19 | JV Girls Basketball | Naugatuck | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | Naugatuck | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Fri., 1/19 | V Girls Indoor Track | Yale High School Invitational | Away | TBA | ||
| Sat., 1/20 | V Wrestling | Eagle Classic | Away - East Catholic HS | 9:00 a.m. | ||
| Mon., 1/22 | V Girls Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 6:30 p.m. | W 53-33 | |
| Mon., 1/22 | JV Girls Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 5:00 p.m. | ||
| Mon., 1/22 | V Girls Gymnastics | Jonathan Law, Daniel Hand, Newtown | Away - Jonathan Law HS Old Gym [Directions] | 6:00 p.m. | 132.7 | |
| Tue., 1/23 | V Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 7:00 p.m. | W 72-49 | |
| Tue., 1/23 | JV Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 5:15 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Watertown | Away - Robert B. Cook Memorial Gymnasium @ Watertown HS [Directions] | 3:45 p.m. | ||
| Tue., 1/23 | V Boys Swimming and Diving | Kennedy | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Hamden | Home - Bennett Rink [Directions] | 6:15 p.m. | L 4-1 | |
| Wed., 1/24 | V Wrestling | Nonnewaug | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/24 | V Girls Basketball | Watertown | Home - Seymour HS [Directions] | 7:00 p.m. | W 53-39 | |
| Wed., 1/24 | JV Girls Basketball | Watertown | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Thu., 1/25 | V Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 7:00 p.m. | L 50-62 | |
| Thu., 1/25 | JV Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/25 | FR Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Shelton | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Sat., 1/27 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Bennett Rink [Directions] | 1:00 p.m. | L 2-1 (OT) | |
| Sat., 1/27 | V Wrestling | Doc Meyers Classic | Away - Rocky Hill HS | 9:00 a.m. | ||
| Sat., 1/27 | V Competitive Cheerleading | Quinnipiac | Away | TBA | ||
| Sat., 1/27 | Winter Dance Team | Quinnipiac University | Away | 5:00 p.m. | ||
| Mon., 1/29 | V Boys Indoor Track | NVL Championships | Away - Hillhouse HS | 4:30 p.m. | ||
| Mon., 1/29 | V Girls Indoor Track | NVL Championships | Away - Hillhouse HS | 4:30 p.m. | ||
| Tue., 1/30 | V Boys Basketball | Kennedy | Home - Seymour HS [Directions] | 7:00 p.m. | L 72-81 | |
| Tue., 1/30 | JV Boys Basketball | Kennedy | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Kennedy | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Oxford | Away - OHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 7:00 p.m. | W 58-29 | |
| Tue., 1/30 | JV Girls Basketball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:30 p.m. | ||
| Wed., 1/31 | V Wrestling | Notre Dame-West Haven | Away [Directions] | Cancelled | Cancelled | |
| Fri., 2/2 | V Boys Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 7:00 p.m. | W 59-52 | |
| Fri., 2/2 | JV Boys Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | St. Paul Catholic | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Wilby/Kaynor | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Fri., 2/2 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:15 p.m. | ||
| Fri., 2/2 | V Girls Gymnastics | Newtown, Joel Barlow | Away - Gymnastics & Cheer Academy [Directions] | 5:30 p.m. | 132.05 | |
| Sat., 2/3 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Bennett Rink [Directions] | 1:00 p.m. | L 1-4 | |
| Sat., 2/3 | V Wrestling | Morgan, Griswold/Wheeler, Granby Memorial, Canton | Away - Morgan HS [Directions] | 9:00 a.m. | ||
| Sat., 2/3 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 44-61 | |
| Sat., 2/3 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 2:30 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Ansonia | Home - Seymour HS [Directions] | 7:00 p.m. | W 83-65 | |
| Tue., 2/6 | JV Boys Basketball | Ansonia | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Ansonia | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 6:00 p.m. | L 48-53 | |
| Tue., 2/6 | JV Girls Basketball | Ansonia | Away - Ansonia HS [Directions] | 4:15 p.m. | ||
| Thu., 2/8 | V Wrestling | St. Paul Catholic | Home - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 2/8 | V Girls Gymnastics | SWC Championship | Away [Directions] | 5:00 p.m. | 135.7 | |
| Fri., 2/9 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | W 83-50 | |
| Fri., 2/9 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Watertown | Home - Seymour HS [Directions] | 6:00 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Oxford | Home - Seymour HS [Directions] | 7:00 p.m. | W 66-51 | |
| Sat., 2/10 | V Boys Ice Hockey | Xavier | Home - Bennett Rink [Directions] | 1:00 p.m. | L 0-6 | |
| Sat., 2/10 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 2/10 | V Wrestling | Berkshire/Valley Tournament | Away - Northwestern HS | 9:00 a.m. | ||
| Sat., 2/10 | V Competitive Cheerleading | Fairfield Warde | Away | TBA | ||
| Sat., 2/10 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Mon., 2/12 | V Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 7:00 p.m. | L 68-74 | |
| Mon., 2/12 | JV Boys Basketball | Derby | Away - Derby HS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/12 | V Boys Ice Hockey | North Rockland (NY) | Home - Bennett Rink [Directions] | 5:00 p.m. | L 10-5 | |
| Mon., 2/12 | V Girls Basketball | Derby | Home - Seymour HS [Directions] | 7:00 p.m. | W 67-27 | |
| Mon., 2/12 | JV Girls Basketball | Derby | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 2/13 | V Girls Gymnastics | New Milford, Newtown | Away [Directions] | 5:00 p.m. | 131.50 | |
| Wed., 2/14 | V Boys Basketball | Woodland | Home - Seymour HS [Directions] | 7:00 p.m. | W 79-72 | |
| Wed., 2/14 | JV Boys Basketball | Woodland | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Woodland | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | Milford Coop | Home - Bennett Rink [Directions] | 6:30 p.m. | W 6-2 | |
| Wed., 2/14 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | ||
| Wed., 2/14 | V Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 7:00 p.m. | W 65-31 | |
| Wed., 2/14 | JV Girls Basketball | Woodland | Away - Woodland HS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/16 | V Boys Basketball | Torrington | Home - Seymour HS [Directions] | 7:00 p.m. | W 77-73 | |
| Fri., 2/16 | JV Boys Basketball | Torrington | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Fri., 2/16 | FR Boys Basketball | Torrington | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Fri., 2/16 | V Wrestling | Class S State Championships | Away - Windham HS | 4:00 p.m. | ||
| Fri., 2/16 | V Girls Gymnastics | Newtown, Fairfield Ludlowe, Nonnewaug, Pomperaug | Away - Auxiliary Gym [Directions] | 6:00 p.m. | 130.45 | |
| Sat., 2/17 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | 4:00 p.m. | L 2-5 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/17 | V Wrestling | Class S State Championships | Away - Windham HS | 9:00 a.m. | ||
| Sat., 2/17 | V Competitive Cheerleading | NVL Championships | Away | TBA | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | 2:00 p.m. | W 4-1 | |
| Mon., 2/19 | V Girls Gymnastics | Pomperaug, Nonnewaug, Newtown | Away - Kinetic Kids [Directions] | 10:00 a.m.p.m. | 126.55 | |
| Tue., 2/20 | V Boys Basketball | Kaynor Tech | Home - Seymour HS [Directions] | 7:00 p.m. | W 86-52 | |
| Tue., 2/20 | JV Boys Basketball | Kaynor Tech | Home - Seymour HS [Directions] | 5:15 p.m. | ||
| Tue., 2/20 | FR Boys Basketball | Kaynor Tech | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Wed., 2/21 | Winter Dance Team | NVL Championships | Away - Woodland HS | 6:00 p.m. | ||
| Thu., 2/22 | FR Boys Basketball | Wilby | Away [Directions] | 3:45 p.m. | ||
| Fri., 2/23 | V Boys Basketball | Wilby | Away - Wilby H.S. [Directions] | 7:00 p.m. | W 64-59 | |
| Fri., 2/23 | JV Boys Basketball | Wilby | Away - Wilby H.S. [Directions] | 5:15 p.m. | ||
| Fri., 2/23 | V Wrestling | State Open Championships | Away - Floyd Little Athletic Center, NH | 3:30 p.m. | ||
| Sat., 2/24 | V Boys Ice Hockey | Glastonbury | Away - Trinity College [Directions] | 7:30 p.m. | L 1-2 | |
| Sat., 2/24 | V Boys Indoor Track | Dream Big Pentathalon Invitational | Away - The Armory | TBA | ||
| Sat., 2/24 | V Wrestling | State Open Championships | Away - Floyd Little Athletic Center, NH | 9:00 a.m. | ||
| Sat., 2/24 | V Girls Gymnastics | CIAC Class Meet | Away | TBA | ||
| Sat., 2/24 | V Girls Indoor Track | Dream Big Pentathalon Invitational | Away - The Armory | TBA | ||
| Mon., 2/26 | V Girls Basketball | Lewis Mills | Home - Seymour HS [Directions] | 7:00 p.m. | W 63-58 | |
| Tue., 2/27 | V Boys Swimming and Diving | NVL Trials | Away | 4:00 p.m. | ||
| Wed., 2/28 | V Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | 7:00 p.m. | L 3-4(OT) | |
| Thu., 3/1 | V Boys Swimming and Diving | NVL Finals | Away | 4:30 p.m. | ||
| Thu., 3/1 | V Girls Basketball | Rocky Hill | Away - Rocky Hill HS [Directions] | 7:00 p.m. | L 44-62 | |
| Sat., 3/3 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/3 | V Girls Gymnastics | CIAC Open | Away | TBA | ||
| Sat., 3/3 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 3/4 | V Competitive Cheerleading | State Championship | Away | TBA | ||
| Tue., 3/6 | V Boys Basketball | Creed | Home - Seymour MS [Directions] | 7:00 p.m. | W 53-50 (OT) | |
| Fri., 3/9 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:00 p.m. | L 52-69 | |
| Sat., 3/10 | V Boys Swimming and Diving | State Trials | Away - Plainville HS | 3:30 p.m. | ||
| Sat., 3/10 | V Girls Gymnastics | New Englands | Away | TBA | ||
| Wed., 3/14 | V Boys Swimming and Diving | State Finals | Away - Cornerstone Aquatic Center, West Hartford | 6:00 p.m. | ||
| Sat., 3/17 | V Boys Swimming and Diving | State Open | Away - Yale | 2:30 p.m. | ||
| Thu., 3/22 | V Softball | Trumbull (Scrim.) | Away - InSports [Directions] | 3:15 p.m. | ||
| Sat., 3/24 | V Baseball | New Milford (Scrim.) | Away - New Milford HS [Directions] | 12:00 p.m. | ||
| Sat., 3/24 | V Softball | Norwich Free Academy (Scrim.) | Home - Seymour HS [Directions] | 11:00 a.m. | ||
| Sat., 3/24 | V Softball | Amity (Scrim.) | Home - Seymour HS [Directions] | 1:30 p.m. | ||
| Mon., 3/26 | V Softball | Stamford (Scrim.) | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 3/27 | V Baseball | Trumbull (Scrim.) | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 3/27 | JV Baseball | Trumbull (Scrim.) | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/28 | V Baseball | Lewis Mills (Scrim.) | Home - French Park [Directions] | 3:45 p.m. | ||
| Wed., 3/28 | V Softball | Pomperaug (Scrim.) | Home - Seymour HS [Directions] | 3:45 p.m. | ||
| Sat., 3/31 | V Baseball | Immaculate | Away - Immaculate HS [Directions] | 12:00 p.m. | L 2-9 | |
| Sat., 3/31 | V Softball | Cheshire (Scrim.) | Home - Seymour HS [Directions] | 10:00 a.m. | ||
| Thu., 4/5 | V Baseball | Holy Cross | Home - French Park [Directions] | 3:30 p.m. | L 1-5 | |
| Thu., 4/5 | V Boys Outdoor Track | Derby, Kennedy | Home - Seymour HS Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 4/5 | V Girls Outdoor Track | Derby, Kennedy | Home - Seymour HS Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 4/5 | V Softball | WCA | Home - Seymour HS [Directions] | 3:45 p.m. | W 20-0 | |
| Thu., 4/5 | V Girls Tennis | Holy Cross | Away - Holy Cross HS [Directions] | 3:45 p.m. | L 5-2 | |
| Sat., 4/7 | JV Baseball | WCA | Away - Washington Park [Directions] | 10:30 a.m. | ||
| Mon., 4/9 | V Baseball | Kennedy | Home - French Park [Directions] | 3:30 p.m. | W 13-0 | |
| Mon., 4/9 | V Softball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 3:30 p.m. | W 23-0 | |
| Mon., 4/9 | JV Softball | Kennedy | Away - Town Plot Park [Directions] | 3:30 p.m. | W 22-1 | |
| Mon., 4/9 | V Girls Tennis | Kennedy | Away - Chase Park [Directions] | 3:45 p.m. | W 6-1 | |
| Tue., 4/10 | JV Baseball | Kennedy | Home - French Park [Directions] | 3:30 p.m. | ||
| Wed., 4/11 | V Baseball | Ansonia | Home - French Park [Directions] | 3:30 p.m. | W 13-3 | |
| Wed., 4/11 | V Boys Golf | Watertown | Home - Oxford Greens [Directions] | 3:00 p.m. | Seymour 239 Watertown 232 Cody Guillette 48,joe Sollami 62, Dibran Trepca 62, Ryan McCormick 67 | |
| Wed., 4/11 | V Boys Outdoor Track | WCA, Sacred Heart | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Wed., 4/11 | V Girls Outdoor Track | WCA, Sacred Heart | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Wed., 4/11 | V Softball | Ansonia | Away - Ansonia HS [Directions] | 3:30 p.m. | W 16-1 | |
| Wed., 4/11 | V Girls Tennis | Sacred Heart | Home - Seymour HS [Directions] | 3:30 p.m. | L 7-0 | |
| Thu., 4/12 | V Baseball | WCA | Away - Washington Park [Directions] | 3:30 p.m. | W 18-2 | |
| Thu., 4/12 | JV Baseball | St. Paul Catholic | Home - French Park [Directions] | 3:45 p.m. | ||
| Thu., 4/12 | V Boys Golf | Naugatuck | Away - Hop Brook [Directions] | 3:00 p.m. | seymour 215-naugatuck 248 guillette 46, Harmon 47, Trebca 59, Sollami 63 | |
| Thu., 4/12 | V Girls Tennis | Watertown | Home - Seymour HS [Directions] | 3:45 p.m. | L 4-3 | |
| Fri., 4/13 | V Baseball | Derby | Home - French Park [Directions] | 3:30 p.m. | W 10-0 | |
| Fri., 4/13 | V Softball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 4:00 p.m. | W 21-0 | |
| Fri., 4/13 | V Girls Tennis | St. Paul Catholic | Home - Seymour HS [Directions] | 3:45 p.m. | L 6-1 | |
| Sat., 4/14 | JV Baseball | Derby | Home - French Park [Directions] | 11:00 a.m. | ||
| Sat., 4/14 | V Boys Outdoor Track | Crosby, Woodland | Home - Seymour HS Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/14 | V Girls Outdoor Track | Crosby, Woodland | Home - Seymour HS Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/14 | JV Softball | Amity | Home - Seymour HS [Directions] | 10:00 a.m. | L 12-6 | |
| Tue., 4/17 | V Boys Golf | St. Paul Catholic | Home - Oxford Greens [Directions] | 2:45 p.m. | seymour 220- St. Paul Catholic 184 Guillette-47,Harmon 51, Scott 58, McCormick 64 | |
| Tue., 4/17 | V Softball | Torrington | Home - Seymour HS [Directions] | 2:00 p.m. | W 15-1 | |
| Tue., 4/17 | V Girls Tennis | Torrington | Home - Seymour HS [Directions] | 2:00 p.m. | W 4-3 | |
| Wed., 4/18 | V Baseball | Sacred Heart | Away - Municipal Stadium | 11:00 a.m. | W 6-2 | |
| Wed., 4/18 | V Softball | Sacred Heart | Home - Seymour HS [Directions] | 11:00 a.m. | W 16-1 | |
| Wed., 4/18 | V Girls Tennis | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:30 p.m. | W 5-2 | |
| Fri., 4/20 | V Softball | Woodland | Away - Woodland Softball Field [Directions] | 3:30 p.m. | W 13-1 | |
| Fri., 4/20 | V Girls Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 11:00 a.m. | L 6-1 | |
| Sat., 4/21 | V Baseball | Pomperaug | Home - French Park [Directions] | 11:00 a.m. | W 17-4 | |
| Sat., 4/21 | V Softball | Holy Cross | Away - Holy Cross HS [Directions] | 1:00 p.m. | W 15-9 | |
| Mon., 4/23 | V Baseball | Torrington | Home - French Park [Directions] | 4:00 p.m. | W 9-7 | |
| Mon., 4/23 | V Softball | Torrington | Away - Torrington HS [Directions] | 4:00 p.m. | W 18-0 | |
| Tue., 4/24 | V Baseball | Oxford | Home - French Park [Directions] | 3:30 p.m. | W 12-0 | |
| Tue., 4/24 | JV Baseball | Torrington | Home - Seymour HS [Directions] | 3:30 p.m. | ||
| Tue., 4/24 | V Boys Golf | Sacred Heart | Home - Oxford Greens [Directions] | 3:00 p.m. | Seymour 206, Sacred heart 205 Guillette 44,Harmon 48, Sollami 53, Scott 61 | |
| Tue., 4/24 | V Boys Outdoor Track | Holy Cross, Watertown | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 4/24 | V Girls Outdoor Track | Holy Cross, Watertown | Away - Holy Cross HS [Directions] | 3:30 p.m. | ||
| Tue., 4/24 | V Softball | Oxford | Away - OHS Softball Field [Directions] | 3:30 p.m. | W 8-6 | |
| Tue., 4/24 | V Girls Tennis | Woodland | Home - Seymour HS [Directions] | 3:30 p.m. | L 1-6 | |
| Thu., 4/26 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | 3:30 p.m. | W 8-7 | |
| Thu., 4/26 | JV Baseball | Oxford | Home - French Park [Directions] | 4:00 p.m. | ||
| Thu., 4/26 | V Boys Golf | Waterbury Coop, Wilby | Away [Directions] | 2:30 p.m. | Seymour 198-Wilby 252 Seymour 198- Kennedy 285 guillette 41 harmon 46 Sollami 55 DeJarnette 56 | |
| Thu., 4/26 | V Softball | Wolcott | Home - Seymour HS [Directions] | 3:30 p.m. | W 3-0 | |
| Thu., 4/26 | JV Softball | Oxford | Away - OHS Softball Field [Directions] | 3:30 p.m. | W 18-2 | |
| Sat., 4/28 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | TBA | ||
| Sat., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | TBA | ||
| Sat., 4/28 | V Girls Tennis | Wolcott | Home - Seymour HS [Directions] | 11:00 a.m. | L 1-6 | |
| Mon., 4/30 | V Baseball | Watertown | Away - Deland Field [Directions] | 3:45 p.m. | W 9-1 | |
| Mon., 4/30 | V Softball | Watertown | Home - Seymour HS [Directions] | 6:30 p.m. | W 8-0 | |
| Mon., 4/30 | JV Softball | Holy Cross | Away - Holy Cross HS [Directions] | 4:00 p.m. | W 16-0 | |
| Tue., 5/1 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 2-9 | |
| Tue., 5/1 | V Boys Outdoor Track | Oxford, St. Paul Catholic | Away - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 5/1 | V Girls Outdoor Track | Oxford, St. Paul Catholic | Away - OHS Track [Directions] | 3:45 p.m. | ||
| Tue., 5/1 | V Girls Tennis | Crosby | Home - Seymour HS [Directions] | 3:30 p.m. | W 7-0 | |
| Wed., 5/2 | V Baseball | Crosby | Home - French Park [Directions] | 3:30 p.m. | W 18-0 | |
| Wed., 5/2 | V Boys Golf | Woodland | Home - Oxford Greens [Directions] | 3:00 p.m. | woodland 181 Seymour 201 Guillette 40,Harmon 41, McCormick 59,Sollami 61 | |
| Wed., 5/2 | V Softball | Waterford | Away - Veterans Field [Directions] | 4:30 p.m. | W 12-0 | |
| Wed., 5/2 | V Girls Tennis | Wilby | Away - Wilby H.S. [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/3 | V Baseball | Ansonia | Away - Nolan Field, Ansonia [Directions] | 3:45 p.m. | W 12-1 | |
| Thu., 5/3 | JV Baseball | Woodland | Away [Directions] | 4:00 p.m. | ||
| Thu., 5/3 | V Boys Golf | Woodland Invitational | Away - Oxford Greens | TBA | ||
| Thu., 5/3 | V Softball | Ansonia | Home - Seymour HS [Directions] | 5:00 p.m. | W 24-0 | |
| Fri., 5/4 | JV Baseball | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Fri., 5/4 | V Girls Tennis | Woodland | Away - Woodland HS Tennis courts [Directions] | 3:30 p.m. | L 3-4 | |
| Mon., 5/7 | V Baseball | St. Paul Catholic | Home - French Park [Directions] | 4:00 p.m. | L 1-4 | |
| Mon., 5/7 | V Boys Golf | Wolcott | Away - Farmingbury Country Club [Directions] | 2:30 p.m. | Wolcott 206 Seymour 211 Guillette 45 Harmon 55 Thomas 54 Scott 57 | |
| Mon., 5/7 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 5/7 | V Girls Tennis | St. Paul Catholic | Away - Page Park, Bristol [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 5/8 | JV Baseball | St. Paul Catholic | Home - French Park [Directions] | 3:30 p.m. | ||
| Tue., 5/8 | V Boys Outdoor Track | Naugatuck, Wilby | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 5/8 | V Girls Outdoor Track | Naugatuck, Wilby | Home - Seymour HS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 5/8 | JV Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:00 p.m. | W 13-0 | |
| Wed., 5/9 | V Baseball | Derby | Away - French Park [Directions] | 3:30 p.m. | W 17-7 | |
| Wed., 5/9 | V Boys Golf | 36th Annual Stigberg Tournament | Away - Farmingbury Country Club | 10:00 a.m. | ||
| Wed., 5/9 | V Softball | Derby | Home - Seymour HS [Directions] | 6:30 p.m. | W 17-0 | |
| Wed., 5/9 | V Girls Tennis | Ansonia | Home - Seymour HS [Directions] | 3:30 p.m. | W 6-1 | |
| Thu., 5/10 | JV Baseball | Derby | Away - Derby -Amendola Field/Bradley School [Directions] | 3:30 p.m. | ||
| Thu., 5/10 | V Boys Golf | Naugatuck | Home - Oxford Greens [Directions] | 3:00 p.m. | Seymour 207- Naugatuck 239 Guillette 42 Harmon 51 sollami 56 Thomas 58 | |
| Fri., 5/11 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | 3:45 p.m. | L 0-4 | |
| Fri., 5/11 | JV Baseball | Oxford | Home - French Park [Directions] | 3:45 p.m. | ||
| Fri., 5/11 | V Softball | Oxford | Home - Seymour HS [Directions] | 7:00 p.m. | W 13-0 | |
| Sat., 5/12 | V Boys Outdoor Track | IRV Black High School Invitational | Away - New Britain HS | TBA | ||
| Sat., 5/12 | V Girls Outdoor Track | Irv Black High School Invitational | Away - New Britain HS | TBA | ||
| Mon., 5/14 | V Baseball | Naugatuck | Home - French Park [Directions] | 3:30 p.m. | W 9-2 | |
| Mon., 5/14 | V Boys Golf | Holy Cross | Away - W Hills [Directions] | 2:30 p.m. | seymour 210 holy cross 172 Guillette 44 Harmon 54 Sollami 55 scott 57 | |
| Mon., 5/14 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 5/14 | V Girls Tennis | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 5/15 | JV Baseball | Naugatuck | Away - Naugatuck [Directions] | Cancelled | Cancelled | |
| Wed., 5/16 | V Boys Outdoor Track | Wolcott, Torrington | Away - Wolcott HS [Directions] | 3:30 p.m. | ||
| Wed., 5/16 | V Girls Outdoor Track | Wolcott, Torrington | Away - Wolcott HS [Directions] | 3:30 p.m. | ||
| Fri., 5/18 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:30 p.m. | L 8-10 | |
| Fri., 5/18 | V Softball | St. Paul Catholic | Home - St. Paul Catholic H.S. [Directions] | 3:15 p.m. | W 10-2 | |
| Mon., 5/21 | V Boys Golf | Torrington | Home - Farminbury Country Club [Directions] | 2:30 p.m. | Seymour 198 Guillette 45 Harmon 42 sallomi 57 Thomas 54 | |
| Mon., 5/21 | V Boys Golf | Wolcott | Home - Farminbury Country Club [Directions] | 2:30 p.m. | Seymour 198 Wolcott 205 Guillette 45,Harmon 42,Thomas 54,Sollami 57 | |
| Mon., 5/21 | V Softball | Westhill | Home - Seymour HS [Directions] | 6:00 p.m. | W 7-0 | |
| Tue., 5/22 | V Boys Outdoor Track | NVL Championships | Home - Seymour HS [Directions] | 1:30 p.m. | ||
| Tue., 5/22 | V Girls Outdoor Track | NVL Championships | Home - Seymour HS [Directions] | 1:30 p.m. | ||
| Wed., 5/23 | V Baseball | Woodland | Away - Woodland HS Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/23 | V Boys Golf | Watertown | Away - Crestbrook Park Golf Course [Directions] | 3:00 p.m. | Watertown 194 Seymour 205. Guillette 46,Harmon 50,Sollami 52,Scott 57 | |
| Wed., 5/23 | V Softball | NVL Quarter Finals | Home - Seymour HS [Directions] | 4:30 p.m. | ||
| Thu., 5/24 | V Baseball | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | 2:00 p.m. | ||
| Thu., 5/24 | V Boys Golf | Chappa Invitational | Away - Long Shore Golf Course- Westport | 8:00 a.m. | ||
| Thu., 5/24 | V Boys Golf | St. Paul Catholic | Away - Chippanee Golf Club [Directions] | 3:00 p.m. | Seymour 231-st paul181 Sollami 52 scott57 Thomas63 Mccormick 59 | |
| Thu., 5/24 | V Softball | Wolcott | Home - Naugatuck HS [Directions] | 6:00 p.m. | ||
| Tue., 5/29 | V Boys Golf | Torrington, Naugatck, Wolcott | Away - Torrington Country Club [Directions] | 2:30 p.m. | ||
| Tue., 5/29 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/29 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Tue., 5/29 | V Softball | Platt Tech | Home - Seymour HS [Directions] | 4:00 p.m. | W 17-0 | |
| Wed., 5/30 | V Baseball | Ellington | Home - French Park [Directions] | 3:30 p.m. | ||
| Wed., 5/30 | V Softball | Notre Dame-Fairfield | Home - Higher Seed [Directions] | 3:30 p.m. | W 12-0 | |
| Thu., 5/31 | V Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:30 p.m. | ||
| Sat., 6/2 | V Baseball | Northwest Catholic | Home - French Park [Directions] | 3:45 p.m. | ||
| Sun., 6/3 | V Softball | Granby Memorial | Home - Seymour HS [Directions] | 2:00 p.m. | ||
| Mon., 6/4 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Mon., 6/4 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Tue., 6/5 | V Softball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Wed., 6/6 | V Baseball | St. Joseph | Home - Palmer Field [Directions] | 7:00 p.m. | ||
| Sat., 6/9 | V Baseball | Wolcott | Away - Palmer Field, Middletown [Directions] | 7:00 p.m. | ||
| Sat., 6/9 | V Boys Outdoor Track | New England Championship | Away - Univ. of New Hampshire [Directions] | TBA | ||
| Sat., 6/9 | V Girls Outdoor Track | New England Championship | Away - Univ. of New Hampshire [Directions] | TBA | ||
| Sat., 6/9 | V Softball | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Tue., 6/12 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away [Directions] | 11:00 a.m. | ||
| Tue., 6/12 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Wed., 6/13 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||