| O'Brien Tech 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 304 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 9/2 | V Football | Oxford (Scrim.) | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 5:00 p.m. | ||
| Tue., 9/7 | V Boys Soccer | Bassick (Scrim.) | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 9/9 | V Boys Soccer | Abbott Tech | Away - Broadview MS-Stephen A. Kaplanis Turf Field [Directions] | 3:30 p.m. | L 0-4 | |
| Thu., 9/9 | V Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 9/9 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 3:45 p.m. | ||
| Fri., 9/10 | V Boys Soccer | Wright Tech | Away - Scalzi Park [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 9/10 | V Girls Swimming and Diving | Jonathan Law | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 102-82 | |
| Fri., 9/10 | V Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/10 | JV Girls Volleyball | Ansonia | Away - Ansonia HS-Gym [Directions] | 4:15 p.m. | ||
| Sat., 9/11 | V Football | Norwich Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 11:00 a.m. | L 6-36 | |
| Mon., 9/13 | V Girls Volleyball | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | L 0-3 | CTC |
| Mon., 9/13 | JV Girls Volleyball | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Wed., 9/15 | V Boys Soccer | Wright Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 4-1 | CTC |
| Wed., 9/15 | V Girls Volleyball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | W 3-0 | CTC |
| Wed., 9/15 | JV Girls Volleyball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Fri., 9/17 | V Football | VGW Techs | Away - Pat Kidney Field-Pat Kidney 1 [Directions] | 6:00 p.m. | W 38-8 | |
| Fri., 9/17 | V Boys Soccer | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | T 1-1 | CTC |
| Fri., 9/17 | V Girls Swimming and Diving | Wilby/Kaynor Tech/WCA | Away - Wilby HS-Gil Cyr Natatorium [Directions] | 4:00 p.m. | Win 76-45 | |
| Fri., 9/17 | V Girls Volleyball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 5:15 p.m. | W 3-0 | CTC |
| Fri., 9/17 | JV Girls Volleyball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 3:45 p.m. | ||
| Mon., 9/20 | JV Football | VGW Techs | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | Canceled | Cancelled | |
| Mon., 9/20 | JV Boys Soccer | Platt Tech | Away - ORANGE AVE ATHLETIC COMPLEX [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 9/20 | V Girls Volleyball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | L 0-3 | CTC |
| Mon., 9/20 | JV Girls Volleyball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | V Boys Soccer | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 1-0 | CTC |
| Tue., 9/21 | V Girls Swimming and Diving | St. Paul/Lewis Mills | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 95-82 | |
| Wed., 9/22 | JV Boys Soccer | Abbott Tech | Away - Stephen A. Kaplanis Field, Broadview MS [Directions] | 3:30 p.m. | L 3-5 | |
| Wed., 9/22 | V Girls Volleyball | Abbott Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Wed., 9/22 | JV Girls Volleyball | Abbott Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Thu., 9/23 | V Boys Soccer | Bullard Havens Tech | Away - Bullard Havens Tech-Soccer Field [Directions] | 4:00 p.m. | L 1-5 | |
| Thu., 9/23 | V Girls Volleyball | Ansonia | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 9/23 | JV Girls Volleyball | Ansonia | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Fri., 9/24 | V Girls Swimming and Diving | Seymour | Away - Seymour HS-pool [Directions] | 3:00 p.m. | Win 93-70 | |
| Sat., 9/25 | V Football | Cheney Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 11:00 a.m. | L 12-34 | |
| Mon., 9/27 | V Girls Volleyball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:15 p.m. | L 1-3 | CTC |
| Mon., 9/27 | JV Girls Volleyball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 9/28 | V Girls Swimming and Diving | Pomperaug | Home - Woodland HS-pool [Directions] | Postponed | Cacelled | |
| Wed., 9/29 | V Girls Volleyball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 5:15 p.m. | W 3-1 | CTC |
| Wed., 9/29 | JV Girls Volleyball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 9/30 | V Boys Soccer | Cheney Tech | Away - Cheney Tech.-Soccer Field [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 9/30 | V Girls Volleyball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | W 3-1 | CTC |
| Thu., 9/30 | JV Girls Volleyball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/1 | JV Boys Soccer | Abbott Tech | Away - Broadview MS-Stephen A. Kaplanis Turf Field [Directions] | 3:30 p.m. | L 1-3 | |
| Fri., 10/1 | V Girls Swimming and Diving | Kennedy | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 73-43 | |
| Sat., 10/2 | V Football | Wilcox/Kaynor | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 11:00 a.m. | W 42-14 | |
| Mon., 10/4 | V Girls Volleyball | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | L 0-3 | |
| Mon., 10/4 | JV Girls Volleyball | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | Canceled | Cancelled | |
| Tue., 10/5 | V Boys Soccer | Whitney Tech | Away - Carusone Field [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 10/5 | V Girls Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 3:00 p.m. | Win 99-78 | |
| Wed., 10/6 | JV Boys Soccer | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | L 2-4 | |
| Wed., 10/6 | V Girls Volleyball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | 4:00 p.m. | L 1-3 | CTC |
| Wed., 10/6 | JV Girls Volleyball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | Canceled | Cancelled | |
| Thu., 10/7 | V Boys Soccer | Abbott Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | L 0-3 | CTC |
| Thu., 10/7 | V Girls Volleyball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | W 3-1 | CTC |
| Thu., 10/7 | JV Girls Volleyball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | Canceled | Cancelled | |
| Fri., 10/8 | V Girls Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | Win 94-81 | |
| Tue., 10/12 | V Boys Soccer | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/12 | V Girls Swimming and Diving | Suffield | Home - Woodland HS-pool [Directions] | 5:00 p.m. | Win 89-762 | |
| Wed., 10/13 | V Boys Soccer | Platt Tech | Away - ORANGE AVE ATHLETIC COMPLEX [Directions] | 3:45 p.m. | L 0-2 | CTC |
| Wed., 10/13 | V Girls Volleyball | Whitney Tech | Away - Eli Whitney RVTS-Gym [Directions] | 5:15 p.m. | W 3-2 | CTC |
| Wed., 10/13 | JV Girls Volleyball | Whitney Tech | Away - Eli Whitney RVTS-Gym [Directions] | 3:45 p.m. | ||
| Thu., 10/14 | V Football | Northwest United | Away - Nonnewaug HS-Turf Field [Directions] | 7:00 p.m. | L 8-44 | |
| Thu., 10/14 | V Girls Volleyball | Bassick | Away - Bassick HS-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/14 | JV Girls Volleyball | Bassick | Away - Bassick HS-Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/15 | V Boys Soccer | Kaynor Tech | Away - Kaynor Technical School-Kaynor Soccer Field [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 10/15 | V Girls Swimming and Diving | Torrington | Home - Woodland HS-pool [Directions] | 4:00 p.m. | Win 85-79 | |
| Mon., 10/18 | JV Boys Soccer | Platt Tech | Away - ORANGE AVE ATHLETIC COMPLEX [Directions] | 3:45 p.m. | L 0-3 | |
| Mon., 10/18 | V Girls Volleyball | Windham Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/18 | JV Girls Volleyball | Windham Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 10/19 | V Girls Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 6:00 p.m. | Win 96-76 | |
| Tue., 10/19 | V Girls Volleyball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 5:15 p.m. | W 3-2 | |
| Tue., 10/19 | JV Girls Volleyball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 10/21 | V Boys Soccer | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 10/21 | V Girls Volleyball | Bullard Havens Tech | Away - Bullard Havens Tech-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/21 | JV Girls Volleyball | Bullard Havens Tech | Away - Bullard Havens Tech-Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/22 | V Boys Soccer | Ansonia | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:00 p.m. | W 3-1 | |
| Fri., 10/22 | V Girls Swimming and Diving | Waterford | Home - Woodland HS-pool [Directions] | 5:00 p.m. | win 94-86 | |
| Sat., 10/23 | V Football | Prince Tech-Innovation | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 11:00 a.m. | L 0-28 | |
| Mon., 10/25 | V Boys Soccer | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 1-0 | |
| Mon., 10/25 | V Girls Volleyball | Wright Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/25 | JV Girls Volleyball | Wright Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 3:45 p.m. | ||
| Thu., 10/28 | JV Boys Soccer | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | Canceled | Cancelled | |
| Sat., 10/30 | V Football | ATI | Away - Immaculate HS-Mustang Valley [Directions] | 2:00 p.m. | L 6-40 | |
| Mon., 11/1 | JV Football | ATI | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | Canceled | Cancelled | |
| Mon., 11/1 | V Boys Soccer | Abbott Tech | Away - Broadview MS-Stephen A. Kaplanis Turf Field [Directions] | 2:00 p.m. | L 1-6 | |
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class SS Championship | Away - Wickham Park | 3:40 p.m. | ||
| Mon., 11/1 | V Girls Volleyball | Goodwin Tech | Away - Goodwin Tech-Goodwin Tech Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | V Football | Quinebaug Valley | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 11:00 a.m. | L 12-48 | |
| Mon., 11/8 | JV Football | Quinebaug Valley | Away - Ellis R V Tech School-Football Field [Directions] | Canceled | Cancelled | |
| Mon., 11/8 | V Girls Volleyball | Sheehan | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 11/9 | V Boys Soccer | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/20 | V Football | Bullard/Kolbe | Away - Kennedy Stadium (Bridgeport) [Directions] | 12:00 p.m. | L 8-42 | |
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Thu., 11/25 | V Football | Platt Tech | Away - Lawmen Stadium-LAWMEN STADIUM [Directions] | 10:00 a.m. | L 6-54 | |
| Fri., 12/10 | V Boys Basketball | North Haven (Scrim.) | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 12/13 | V Boys Basketball | Bridgeport Central (Scrim.) | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 3:15 p.m. | ||
| Mon., 12/13 | V Girls Basketball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 6:00 p.m. | L 43-47 | CTC |
| Mon., 12/13 | JV Girls Basketball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/15 | V Girls Basketball | Grasso Tech | Away - Grasso Tech-Grasso Gymnasium [Directions] | 4:30 p.m. | W 26-17 | |
| Thu., 12/16 | V Girls Basketball | Abbott Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 5:30 p.m. | L 58-23 | CTC |
| Thu., 12/16 | JV Girls Basketball | Abbott Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 12/20 | V Boys Basketball | Bullard Havens Tech | Away - Bullard Havens Tech-Gym [Directions] | 6:00 p.m. | W 51-44 | |
| Mon., 12/20 | JV Boys Basketball | Bullard Havens Tech | Away - Bullard Havens Tech-Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/22 | V Boys Basketball | Vinal Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 6:00 p.m. | W 65-44 | |
| Wed., 12/22 | JV Boys Basketball | Vinal Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/22 | V Girls Basketball | Vinal Tech | Away - Vinal Tech-Gym [Directions] | 5:30 p.m. | W 56-20 | |
| Wed., 12/22 | JV Girls Basketball | Vinal Tech | Away - Vinal Tech-Gym [Directions] | 4:00 p.m. | ||
| Tue., 12/28 | V Boys Basketball | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 7:00 p.m. | L 58-44 | |
| Thu., 12/30 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 1:00 p.m. | L 43-76 | |
| Thu., 12/30 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | Postponed | ||
| Tue., 1/4 | V Boys Basketball | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 6:00 p.m. | L 50-63 | CTC |
| Tue., 1/4 | JV Boys Basketball | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/4 | V Girls Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Gym [Directions] | 3:00 p.m. | L 20-44 | CTC |
| Thu., 1/6 | V Girls Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | 5:00 p.m. | W 40-36 | CTC |
| Thu., 1/6 | JV Girls Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | 3:30 p.m. | ||
| Mon., 1/10 | V Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 7:00 p.m. | W 47-12 | |
| Mon., 1/10 | JV Girls Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/11 | V Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 7:00 p.m. | L 50-72 | CTC |
| Tue., 1/11 | JV Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/13 | V Girls Basketball | Whitney Tech | Away - Eli Whitney RVTS-Gym [Directions] | 4:30 p.m. | W 48-14 | CTC |
| Fri., 1/14 | V Boys Basketball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 6:00 p.m. | L 61-35 | CTC |
| Fri., 1/14 | JV Boys Basketball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/15 | FR Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 12:00 p.m. | ||
| Tue., 1/18 | FR Boys Basketball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 1/19 | V Girls Basketball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 6:00 p.m. | L 43-44 | |
| Wed., 1/19 | JV Girls Basketball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 1/21 | V Boys Basketball | Thomaston | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 6:00 p.m. | W 54-35 | |
| Fri., 1/21 | JV Boys Basketball | Thomaston | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 1/24 | V Boys Basketball | Somers | Away - Somers HS-Somers High School Gymnasium [Directions] | 6:45 p.m. | L 39-57 | |
| Mon., 1/24 | JV Boys Basketball | Somers | Away - Somers HS-Somers High School Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/24 | V Girls Basketball | Goodwin Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:00 p.m. | L 40-35 | |
| Tue., 1/25 | V Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:30 p.m. | L 38-61 | CTC |
| Tue., 1/25 | JV Boys Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 6:00 p.m. | W 47-32 | CTC |
| Tue., 1/25 | JV Girls Basketball | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 1/27 | V Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 6:00 p.m. | W 53-37 | CTC |
| Thu., 1/27 | JV Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Wright Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | W 70-27 | CTC |
| Sat., 1/29 | FR Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | Postponed | ||
| Tue., 2/1 | V Boys Basketball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 6:00 p.m. | L 42-44 | CTC |
| Tue., 2/1 | JV Boys Basketball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Bullard Havens Tech | Away - Bullard Havens Tech-Gym [Directions] | 6:00 p.m. | W 48-39 | CTC |
| Tue., 2/1 | JV Girls Basketball | Bullard Havens Tech | Away - Bullard Havens Tech-Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/2 | V Girls Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 6:00 p.m. | L 23-57 | |
| Wed., 2/2 | JV Girls Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 2/3 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:00 p.m. | W 69-58 | |
| Thu., 2/3 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/3 | V Girls Basketball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 6:00 p.m. | W 49-32 | CTC |
| Thu., 2/3 | JV Girls Basketball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 2/5 | FR Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 11:00 a.m. | ||
| Mon., 2/7 | V Boys Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | 7:00 p.m. | W 61-35 | |
| Mon., 2/7 | JV Boys Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/7 | FR Boys Basketball | Wilcox Tech | Away - Wilcox Tech-Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 3:45 p.m. | W 35-29 | |
| Tue., 2/8 | V Boys Basketball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 7:00 p.m. | W 54-47 | CTC |
| Tue., 2/8 | JV Boys Basketball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | FR Boys Basketball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 6:00 p.m. | L 43-38 | |
| Tue., 2/8 | JV Girls Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/9 | V Girls Basketball | Grasso Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | W 49-27 | |
| Thu., 2/10 | V Boys Basketball | Whitney Tech | Away - Eli Whitney RVTS-Gym [Directions] | 6:45 p.m. | L 34-55 | |
| Thu., 2/10 | JV Boys Basketball | Whitney Tech | Away - Eli Whitney RVTS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | FR Boys Basketball | Whitney Tech | Away - Eli Whitney Reg Vo-tech School-Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/10 | FR Boys Basketball | Boys Basketball Game | Away - TBA | 3:45 p.m. | ||
| Thu., 2/10 | V Boys Indoor Track | Class M Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Thu., 2/10 | V Girls Basketball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 5:00 p.m. | W 48-15 | CTC |
| Thu., 2/10 | JV Girls Basketball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 2/12 | FR Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/12 | V Girls Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 7:00 p.m. | W 56-33 | |
| Mon., 2/14 | JV Boys Basketball | Derby | Away - Derby HS-DHS Vitello Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/14 | V Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:30 p.m. | W 52-40 | |
| Mon., 2/14 | JV Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 6:00 p.m. | W 62-31 | |
| Tue., 2/15 | JV Boys Basketball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/15 | FR Boys Basketball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 2/18 | V Boys Basketball | Vinal Tech | Away - Vinal Tech-Gym [Directions] | 5:30 p.m. | W 49-45 | |
| Fri., 2/18 | JV Boys Basketball | Vinal Tech | Away - Vinal Tech-Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/18 | V Wrestling | Class M Championship - Day 1 | Away - East Haven | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class M Championship - Day 2 | Away - East Haven | 11:00 a.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Girls Basketball | Goodwin Tech | Away - Goodwin Tech-Goodwin Tech Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/22 | V Boys Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 6:00 p.m. | L 49-82 | CTC |
| Tue., 2/22 | JV Boys Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Tue., 3/1 | V Girls Basketball | Stonington | Home - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 6:30 p.m. | L 64-21 | |
| Tue., 3/8 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 4:00 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sat., 4/2 | V Baseball | Derby | Away - Payden Park-Payden Field [Directions] | 1:30 p.m. | L 16-15 | |
| Mon., 4/4 | V Softball | Abbott Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 18-0 | |
| Tue., 4/5 | V Boys Golf | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-Orange Hills [Directions] | 2:00 p.m. | O'Brien 232 Wilcox 235 | CTC |
| Tue., 4/5 | V Boys Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Tue., 4/5 | V Girls Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Wed., 4/6 | V Softball | Bullard Havens Tech | Away - Bullard Havens Tech-Beardsley Park [Directions] | 3:45 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 4/21, Time to 3:00 p.m. | ||||||
| Thu., 4/7 | JV Baseball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | Canceled | Cancelled | |
| Thu., 4/7 | V Boys Golf | Vinal Tech | Away - Indian Springs Golf Course-Indian Springs CC [Directions] | 2:00 p.m. | O'Brien 244 Vinal 246 | CTC |
| Mon., 4/11 | V Baseball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | L 10-2 | CTC |
| Mon., 4/11 | V Softball | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 9-3 | CTC |
| Tue., 4/12 | JV Baseball | Wamogo | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Tue., 4/12 | V Boys Golf | Kaynor Tech | Away - East Mountain Golf Course [Directions] | 2:00 p.m. | O'Brien 249 Kaynor 273 | CTC |
| Tue., 4/12 | V Boys Outdoor Track | Woodland, Platt Tech, Torrington | Away - Woodland HS-Track [Directions] | 3:30 p.m. | ||
| Wed., 4/13 | V Baseball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 10:30 a.m. | L 14-4 | CTC |
| Wed., 4/13 | V Softball | Wilcox Tech | Away - Wilcox Tech-Softball Diamond [Directions] | 10:30 a.m. | W 15-3 | CTC |
| Thu., 4/14 | V Baseball | Platt Tech | Away - Milford Academy Field/McCann Natatorium-Milford Academy Field [Directions] | 3:45 p.m. | W 16-3 | CTC |
| Thu., 4/14 | V Boys Golf | University | Home - Emmett O' Brien Reg Voc Tech School-Orange Hills [Directions] | 2:00 p.m. | O'Brien 238 University 314 | |
| Thu., 4/14 | V Softball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 1:30 p.m. | W 11-0 | CTC |
| Sat., 4/16 | JV Softball | Ansonia | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 11:00 a.m. | ||
| Mon., 4/18 | V Baseball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | L 8-4 | CTC |
| Mon., 4/18 | V Softball | Whitney Tech | Away - Eli Whitney RVTS-Softball Field [Directions] | 3:45 p.m. | W 20-0 | CTC |
| Tue., 4/19 | V Boys Golf | Norwich Tech | Home - Emmett O' Brien Reg Voc Tech School-Orange Hills [Directions] | 2:00 p.m. | O'Brien 231 Norwich 229 | CTC |
| Tue., 4/19 | V Boys Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Tue., 4/19 | V Girls Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Baseball | West Haven | Away - West Haven HS-Whitey Piurek Field [Directions] | 3:45 p.m. | L 11-1 | |
| Wed., 4/20 | V Softball | Goodwin Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 17-2 | |
| Thu., 4/21 | V Baseball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 11-6 | |
| Thu., 4/21 | V Boys Golf | Goodwin Tech | Home - Emmett O' Brien Reg Voc Tech School-Orange Hills [Directions] | 2:00 p.m. | O'Brien 233 Goodwin 245 | CTC |
| Thu., 4/21 | V Softball | Bullard Havens Tech | Away - Bullard Havens Tech-Beardsley Park [Directions] | 3:00 p.m. | W 21-0 | |
| Fri., 4/22 | V Baseball | Kaynor Tech | Away - Kaynor Technical School- Kaynor Baseball Diamond [Directions] | 3:45 p.m. | W 11-5 | |
| Fri., 4/22 | V Boys Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Fri., 4/22 | V Girls Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Mon., 4/25 | V Baseball | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 23-5 | CTC |
| Mon., 4/25 | V Boys Golf | University | Away - Keney Park [Directions] | 2:00 p.m. | O'Brien 232 University 297 | |
| Mon., 4/25 | V Softball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Softball Diamond [Directions] | 3:45 p.m. | W 12-3 | CTC |
| Tue., 4/26 | JV Baseball | Platt Tech | Away - Milford Academy Field/McCann Natatorium-Milford Academy Field [Directions] | Canceled | Cancelled | |
| Tue., 4/26 | V Boys Golf | Wolcott Tech | Away - Torrington Country Club [Directions] | 2:00 p.m. | O'Brien 220 Wolcott 232 | CTC |
| Wed., 4/27 | V Baseball | Wright Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 14-4 | CTC |
| Wed., 4/27 | V Softball | Wright Tech | Away - Scalzi Park-Scalzi #3 [Directions] | 3:45 p.m. | W 17-2 | CTC |
| Thu., 4/28 | JV Baseball | Wilcox Tech | Away - Wilcox Tech-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Thu., 4/28 | V Boys Golf | Grasso Tech | Away - Pequot Golf Course [Directions] | 2:15 p.m. | O'Brien 200 Grasso 227 | CTC |
| Thu., 4/28 | V Boys Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Thu., 4/28 | V Girls Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Fri., 4/29 | V Baseball | Bullard Havens Tech | Away - Bullard Havens Tech-Beardsley Park [Directions] | 3:45 p.m. | W 16-2 | CTC |
| Fri., 4/29 | V Softball | Bullard Havens Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 18-2 | CTC |
| Sat., 4/30 | JV Softball | Oxford | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 11:00 a.m. | ||
| Mon., 5/2 | V Baseball | Wilcox Tech | Away - Wilcox Tech-Baseball Diamond [Directions] | 3:45 p.m. | W 11-4 | CTC |
| Mon., 5/2 | V Boys Golf | Wilcox Tech | Away - Hunter Golf Club [Directions] | 2:00 p.m. | O'Brien 215 Wilcox 212 | CTC |
| Wed., 5/4 | V Boys Outdoor Track | West Haven, Hamden | Away - West Haven HS-Ken Strong Stadium [Directions] | 3:45 p.m. | ||
| Wed., 5/4 | V Girls Outdoor Track | West Haven, Hamden | Away - West Haven HS-Ken Strong Stadium [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Boys Golf | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-Orange Hills [Directions] | 2:00 p.m. | O'Brien 221 Kaynor 255 | CTC |
| Fri., 5/6 | V Boys Outdoor Track | Foran, Platt Tech | Away - Foran HS -Foran High School Track [Directions] | Postponed | ||
| Fri., 5/6 | V Girls Outdoor Track | Foran, Platt Tech | Away - Foran HS -Foran High School Track [Directions] | Postponed | ||
| Mon., 5/9 | V Baseball | Platt Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 11-1 | CTC |
| Mon., 5/9 | V Softball | Platt Tech | Away - Foote Field [Directions] | 3:00 p.m. | W 5-3 | CTC |
| Tue., 5/10 | V Baseball | Whitney Tech | Away - Eli Whitney RVTS-Baseball Diamond [Directions] | 3:45 p.m. | W 16-1 | |
| Tue., 5/10 | V Boys Golf | Ellis Tech | Away - Harrisville Golf Course [Directions] | 2:15 p.m. | O'Brien 201 Ellis 185 | CTC |
| Tue., 5/10 | V Softball | Wilcox Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 1:00 p.m. | W 11-7 | CTC |
| Wed., 5/11 | V Boys Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 1:00 p.m. | ||
| Wed., 5/11 | V Girls Outdoor Track | Bullard Havens Tech, Wolcott Tech, Platt Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 1:00 p.m. | ||
| Thu., 5/12 | V Baseball | Ansonia | Away - Nolan Field-Ansonia-Baseball Field [Directions] | 3:00 p.m. | L 6-3 | |
| Thu., 5/12 | V Boys Golf | Vinal Tech | Home - Emmett O' Brien Reg Voc Tech School-Orange Hills [Directions] | 2:00 p.m. | OBrien 228 Vinal 232 | |
| Thu., 5/12 | V Softball | Ansonia | Away - Ansonia HS-Charger Field [Directions] | 3:00 p.m. | W 16-7 | |
| Fri., 5/13 | V Baseball | Wright Tech | Away - Scalzi Park-Cubeta Stadium [Directions] | 3:45 p.m. | W 10-2 | |
| Fri., 5/13 | V Softball | Wright Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 18-1 | |
| Mon., 5/16 | V Baseball | Abbott Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | L 18-5 | CTC |
| Mon., 5/16 | V Softball | Abbott Tech | Away - Hatters Park-Hatters #1 [Directions] | 2:30 p.m. | W 14-1 | CTC |
| Tue., 5/17 | V Boys Golf | Goodwin Tech | Away - Stanley Golf Course [Directions] | 2:00 p.m. | O'Brien 220 Goodwin 252 | CTC |
| Tue., 5/17 | V Boys Outdoor Track | Grasso Tech, Wolcott Tech, Vinal Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Grasso Tech, Wolcott Tech, Vinal Tech, Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Softball | Ansonia | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 2:00 p.m. | L 6-7 | |
| Tue., 5/17 | V Softball | Whitney Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 4:00 p.m. | W 11-5 | CTC |
| Wed., 5/18 | V Baseball | Goodwin Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 12-2 | |
| Thu., 5/19 | V Boys Golf | Prince Tech | Away - Keney Park Golf Course [Directions] | 2:00 p.m. | O'Brien 224 Prince 281 | CTC |
| Thu., 5/19 | V Softball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 4:00 p.m. | W 6-2 | |
| Fri., 5/20 | V Baseball | Ansonia | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | L 3-1 | |
| Sat., 5/21 | V Baseball | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 4:00 p.m. | L 10-7 | |
| Sat., 5/21 | V Softball | WCA | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 10:00 a.m. | W 12-0 | |
| Sat., 5/21 | V Softball | Bassick | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 1:30 p.m. | W Forfeit | |
| Mon., 5/23 | V Baseball | Wilcox Tech | Away - Wilcox Tech-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 5/23 | V Boys Golf | Wolcott Tech | Home - Emmett O' Brien Reg Voc Tech School-Orange Hills [Directions] | 2:00 p.m. | O'Brien 208 Wolcott 240 | CTC |
| Mon., 5/23 | V Softball | Kaynor Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 12-0 | |
| Tue., 5/24 | V Baseball | Ellis Tech | Away - Ellis R V Tech School-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | CTC Outdoor Championship | Away - A I Prince Reg Voc Tech School-Lawrence Stub Track | 12:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/23, Time to 1:00 p.m. | ||||||
| Tue., 5/24 | V Girls Outdoor Track | CTC Outdoor Championship | Away - A I Prince Reg Voc Tech School-Lawrence Stub Track | 12:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/23, Time to 1:00 p.m. | ||||||
| Tue., 5/24 | V Softball | Ellis Tech | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | W 22-2 | |
| Thu., 5/26 | V Softball | Wolcott Tech | Home - Albertus Magnus College-Shea Softball Complex [Directions] | 3:45 p.m. | ||
| Tue., 5/31 | V Baseball | Killingly | Away - Owen Bell Park -Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 6/1 | V Softball | Seymour | Home - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:00 p.m. | L 14-3 | |
| Thu., 6/2 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Thu., 6/2 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Mon., 6/6 | V Boys Golf | CIAC Division II Spring Championship | Away - Tallwood CC | 7:30 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||