| Shepaug Valley 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 466 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Terryville | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| TBA | V Boys Ice Hockey | Forman School (Scrim.) | Away - Rumsey Hall Rink | 7:15 p.m. | ||
| TBA | JV Boys Soccer | Lewis Mills | Away - Lewis Mills JV Soccer Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| TBA | JV Girls Basketball | Litchfield | Away - Litchfield High School [Directions] | Cancelled | 5:30 PM | |
| TBA | JV Girls Soccer | Lewis Mills | Away - Lewis Mills Varsity Soccer Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| TBA | V Softball | New Milford (Scrim.) | Home - Dick Ayer Field [Directions] | 3:45 p.m. | ||
| Thu., 8/28 | V Field Hockey | New Milford (Scrim.) | Away - New Milford High School [Directions] | 3:15 p.m. | 2:25 PM | |
| Thu., 8/28 | V Girls Soccer | Holy Cross (Scrim.) | Away [Directions] | 4:00 p.m. | 2:25 PM | |
| Fri., 8/29 | V Boys Soccer | Danbury (Scrim.) | Away - Danbury High School Stadium [Directions] | 4:30 p.m. | 3:15 PM | |
| Sat., 8/30 | V Field Hockey | Brookfield Play Day | Away | 3:45 p.m. | No Bus | |
| Tue., 9/2 | V Boys Soccer | Sacred Heart (Scrim.) | Away - Bucks Hill Park (Montoe Park) | 3:45 p.m. | 2:25 | |
| Tue., 9/2 | V Girls Soccer | Sacred Heart (Scrim.) | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/4 | V Boys Cross Country | Berkshire League Scrimmage | Away - Black Rock State Park | 4:15 p.m. | 2:25 PM | |
| Thu., 9/4 | V Girls Cross Country | Berkshire League Scrimmage | Away - Black Rock State Park | 4:15 p.m. | 2:25 PM | |
| Sat., 9/6 | V Field Hockey | New Fairfield Play Day | Away | 9:30 a.m. | 7:45 AM | |
| Tue., 9/9 | V Boys Cross Country | Lewis Mills, Gilbert | Away - Lewis Mills H.S. [Directions] | 4:15 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/9 | V Boys Soccer | Terryville | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 1-0 | ||
| Tue., 9/9 | JV Boys Soccer | Terryville | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/9 | V Girls Cross Country | Lewis Mills, Gilbert | Away - Lewis Mills H.S. [Directions] | 4:15 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/9 | V Field Hockey | Northwestern | Away - Northwestern Field [Directions] | W 4-2 | 2:00 | 1:50 PM Dismissal |
| Tue., 9/9 | V Girls Soccer | Terryville | Away [Directions] | W 3-1 | 2:25 PM | 2:15 PM Dismissal |
| Tue., 9/9 | JV Girls Soccer | Terryville | Away - New Terryville High School [Directions] | Cancelled | 2:15 PM | 2:05 Dismissal |
| Wed., 9/10 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | L 0-3 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 9/10 | JV Field Hockey | New Fairfield | Away - Rebel Stadium [Directions] | 5:00 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Wed., 9/10 | JV Girls Soccer | Litchfield | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/11 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | W 3-1 | 2:25 PM | |
| Thu., 9/11 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 9/11 | V Girls Soccer | Litchfield | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 1-0 | ||
| Sat., 9/13 | V Boys Cross Country | Wilton Invitational | Away - Allen's Meadow Park, Wilton CT | 10:00 a.m. | 7:45 AM | |
| Sat., 9/13 | V Football | Wilcox/Kaynor | Home - OWTS School Field [Directions] | L 22-29 | ||
| Sat., 9/13 | V Girls Cross Country | Wilton Invitational | Away - Allen's Meadow Park, Wilton CT | 10:00 a.m. | 7:45 AM | |
| Mon., 9/15 | V Field Hockey | Litchfield | Home - Joan Gauthey Field [Directions] | W 4-0 | ||
| Mon., 9/15 | JV Field Hockey | Litchfield | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 9/16 | V Boys Cross Country | Housatonic Regional, Litchfield | Away [Directions] | 4:15 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/16 | V Boys Soccer | Housatonic Regional | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 1-0 | ||
| Tue., 9/16 | V Girls Cross Country | Housatonic Regional, Litchfield | Away - Housatonic [Directions] | 4:15 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/16 | V Field Hockey | Thomaston | Home - Joan Gauthey Field [Directions] | L 1-2 | ||
| Tue., 9/16 | JV Field Hockey | Thomaston | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 9/16 | V Girls Soccer | Housatonic Regional | Away - High School Field [Directions] | L 4-0 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 9/19 | V Boys Soccer | Thomaston | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 4-1 | ||
| Fri., 9/19 | V Field Hockey | Nonnewaug | Away - Nonnewaug High School Field [Directions] | L 2-4 | 2:25 PM | |
| Fri., 9/19 | JV Field Hockey | Nonnewaug | Away - Nonnewaug High School [Directions] | 5:00 p.m. | 2:25 PM | |
| Fri., 9/19 | V Girls Soccer | Thomaston | Away - Highwood Farms Field [Directions] | W 3-1 | 2:25 PM | |
| Sat., 9/20 | V Boys Cross Country | Stratton Brook Invitational | Away - Stratton Brook Park, Simsbury | TBA | TBA | |
| Sat., 9/20 | V Football | VGW Techs | Home - OWTS School Field [Directions] | L 0-44 | ||
| Sat., 9/20 | V Girls Cross Country | Stratton Brook Invitational | Away - Stratton Brook Park, Simsbury | TBA | TBA | |
| Sat., 9/20 | JV Girls Soccer | Wamogo | Away - Wamogo JV Soccer Field [Directions] | 10:00 a.m. | 8:30 AM | |
| Mon., 9/22 | JV Football | VGW Techs | Away - Vinal Tech Field [Directions] | 3:45 p.m. | ||
| Tue., 9/23 | V Boys Cross Country | Northwestern, Thomaston, Wamogo | Home - Shepaug Valley High School [Directions] | 4:15 p.m. | ||
| Tue., 9/23 | V Girls Cross Country | Northwestern, Thomaston, Wamogo | Home - Shepaug Valley High School [Directions] | 4:15 p.m. | ||
| Tue., 9/23 | V Field Hockey | Wamogo | Home - Joan Gauthey Field [Directions] | W 2-0 | ||
| Tue., 9/23 | JV Field Hockey | Wamogo | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 9/23 | V Girls Soccer | Lewis Mills | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 2-3 | ||
| Wed., 9/24 | V Boys Soccer | Lewis Mills | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 6-1 | ||
| Wed., 9/24 | JV Boys Soccer | Lewis Mills | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 9/24 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | L 1-4 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 9/24 | JV Field Hockey | Brookfield | Away - BHS Back Turf [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 9/26 | V Football | Prince Tech-Innovation | Away - Prince Tech/Moriarty Field [Directions] | L 7-49 | ||
| Fri., 9/26 | V Boys Soccer | Nonnewaug | Away [Directions] | L 0-3 | 2:25 PM | |
| Fri., 9/26 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug High School Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 9/26 | V Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | L 1-5 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 9/26 | JV Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 5:00 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 9/26 | V Girls Soccer | Nonnewaug | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 3-1 | ||
| Sat., 9/27 | V Boys Cross Country | Winding Trails Invitational | Away | 9:00 a.m. | 6:45 AM | |
| Sat., 9/27 | JV Football | Prince Tech-Innovation | Home - Pop Warner Field [Directions] | Cancelled | ||
| Sat., 9/27 | V Girls Cross Country | Winding Trails Invitational | Away | 9:00 a.m. | 6:45 AM | |
| Tue., 9/30 | V Boys Cross Country | Nonnewaug, Terryville | Away - Nonnewaug High School [Directions] | 4:15 p.m. | 2:25 PM | |
| Tue., 9/30 | V Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | L 3-0 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/30 | JV Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/30 | V Girls Cross Country | Nonnewaug, Terryville | Away - Nonnewaug High School [Directions] | 4:15 p.m. | 2:25 PM | |
| Tue., 9/30 | V Field Hockey | Housatonic Regional | Away - High School Field [Directions] | W 3-0 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/30 | V Girls Soccer | Northwestern | Home - Shepaug Valley Varsity Soccer Field [Directions] | T 0-0 | ||
| Thu., 10/2 | V Football | Putnam | Home - OWTS School Field [Directions] | L 17-31 | ||
| Fri., 10/3 | V Boys Cross Country | Nonnewaug Invitational | Away - Nonnewaug High School | 4:15 p.m. | 2:30 PM | |
| Fri., 10/3 | V Boys Soccer | Gilbert | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 5-0 | ||
| Fri., 10/3 | JV Boys Soccer | New Milford | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/3 | JV Boys Soccer | Gilbert | Home - Shepaug Valley High School JV Soccer Field [Directions] | Cancelled | ||
| Fri., 10/3 | V Girls Cross Country | Nonnewaug Invitational | Away - Nonnewaug High School | 4:45 p.m. | 2:30 PM | |
| Fri., 10/3 | V Field Hockey | Northwestern | Home - Joan Gauthey Field [Directions] | T 3-3 [Detailed Results] | ||
| Fri., 10/3 | JV Field Hockey | Northwestern | Home - Joan Gauthey Field [Directions] | Cancelled | ||
| Fri., 10/3 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | W 2-0 | 2:00 PM | 1:50 PM Dismissal |
| Sat., 10/4 | JV Boys Soccer | Northwestern | Home - Shepaug Valley High School JV Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/4 | JV Girls Soccer | Northwestern | Home - Shepaug Valley Varsity Soccer Field [Directions] | 9:00 a.m. | ||
| Mon., 10/6 | JV Football | Putnam | Away - St. Marie Greenhalgh Sports Complex [Directions] | Cancelled | ||
| Tue., 10/7 | V Boys Cross Country | Nonnewaug | Home - Shepaug Valley High School [Directions] | 4:15 p.m. | ||
| Tue., 10/7 | V Boys Soccer | Wamogo | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 5-2 | ||
| Tue., 10/7 | JV Boys Soccer | Wamogo | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/7 | V Girls Cross Country | Nonnewaug | Home - Shepaug Valley High School [Directions] | 4:15 p.m. | ||
| Tue., 10/7 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | W 5-1 | 2:25 PM | |
| Tue., 10/7 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 5:00 p.m. | 2:25 PM | |
| Tue., 10/7 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | W 2-1 | 2:25 PM | |
| Wed., 10/8 | JV Field Hockey | New Milford | Away [Directions] | 4:30 p.m. | 3:15 PM | |
| Thu., 10/9 | V Boys Soccer | Terryville | Away [Directions] | L 1-2 | 2:15 PM | 2:05 PM Dismissal |
| Thu., 10/9 | JV Boys Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | 2:15 PM | 2:05 PM Dismissal |
| Thu., 10/9 | V Girls Soccer | Terryville | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 3-1 | ||
| Thu., 10/9 | JV Girls Soccer | Terryville | Home - Shepaug Valley Varsity Soccer Field [Directions] | Cancelled | ||
| Fri., 10/10 | V Football | Cheney Tech | Away - Cheney Tech [Directions] | L 13-36 | ||
| Sat., 10/11 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park, Manchester CT | 11:25 a.m. | 9:30 AM | |
| Sat., 10/11 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park, Manchester CT | 1:15 p.m. | 9:30 AM | |
| Mon., 10/13 | JV Football | Cheney Tech | Home - Pop Warner Field [Directions] | 11:00 a.m. | ||
| Tue., 10/14 | V Boys Soccer | Litchfield | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 2-1 | ||
| Tue., 10/14 | JV Boys Soccer | Litchfield | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/14 | V Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | L 0-3 | 2:25 PM | |
| Tue., 10/14 | JV Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | 5:00 p.m. | 2:25 PM | |
| Tue., 10/14 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | T 1-1 | 2:25 PM | |
| Fri., 10/17 | V Boys Cross Country | Berkshire League Championship | Away - Black Rock State Park | 4:15 p.m. | 12:45 PM | JV 2:45; Varsity 4:15 PM |
| Fri., 10/17 | V Football | St. Bernard | Away - Delaporta Field [Directions] | L 46-64 | ||
| Fri., 10/17 | V Boys Soccer | Housatonic Regional | Away - Housatonic Field [Directions] | L 2-3 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 10/17 | JV Boys Soccer | Housatonic Regional | Away - Trotta Field Lakeville [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 10/17 | V Girls Cross Country | Berkshire League Championship | Away - Black Rock State Park | 3:30 p.m. | 12:45 PM | |
| Fri., 10/17 | V Field Hockey | Nonnewaug | Home - Joan Gauthey Field [Directions] | L 0-1 | ||
| Fri., 10/17 | JV Field Hockey | Nonnewaug | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Fri., 10/17 | V Girls Soccer | Housatonic Regional | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 4-3 | ||
| Sat., 10/18 | JV Boys Soccer | Housatonic Regional | Home - Shepaug Valley Varsity Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/18 | JV Girls Soccer | Housatonic Regional | Home - Shepaug [Directions] | 10:00 a.m. | ||
| Mon., 10/20 | JV Football | Whitney Tech | Home - Torrington Pop Warner Field [Directions] | 3:30 p.m. | ||
| Tue., 10/21 | V Boys Soccer | Thomaston | Away - Highwood Farms Field [Directions] | T 2-2 | 2:25 PM | |
| Tue., 10/21 | V Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | W 2-1 | 2:25 PM | |
| Tue., 10/21 | JV Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | 2:25 PM | |
| Tue., 10/21 | V Girls Soccer | Thomaston | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 5-0 | ||
| Fri., 10/24 | V Football | Capital/Achievement | Away - Dillon Stadium [Directions] | L 0-41 | ||
| Fri., 10/24 | V Boys Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | L 1-2 | 3:00 PM | |
| Fri., 10/24 | V Girls Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | L 3-0 | 3:00 PM | |
| Sat., 10/25 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park, Manchester CT | 2:40 p.m. | 11:00 AM | |
| Sat., 10/25 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park, Manchester CT | 2:05 p.m. | 11:00 AM | |
| Sat., 10/25 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 10:00 a.m. | 8:30 AM | |
| Mon., 10/27 | JV Football | Lewis Mills | Home - Torrington Pop Warner Field [Directions] | 3:45 p.m. | ||
| Mon., 10/27 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | T 1-1 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 10/27 | JV Boys Soccer | Gilbert | Away - Rowley Field [Directions] | Cancelled | 2:00 PM | 1:50 PM Dismissal |
| Mon., 10/27 | V Field Hockey | Lewis Mills | Home - Joan Gauthey Field [Directions] | L 1-3 | ||
| Mon., 10/27 | JV Field Hockey | Lewis Mills | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Mon., 10/27 | V Girls Soccer | Gilbert | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 2-0 | ||
| Tue., 10/28 | V Field Hockey | Housatonic Regional | Home - Joan Gauthey Field [Directions] | W 3-1 | ||
| Wed., 10/29 | V Boys Soccer | Nonnewaug | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 1-3 | ||
| Wed., 10/29 | JV Boys Soccer | Nonnewaug | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/29 | V Girls Soccer | Nonnewaug | Away - Nonnewaug High School Field [Directions] | L 1-0 | 2:25 PM | |
| Fri., 10/31 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park, Manchester CT | 2:45 p.m. | 11:00 AM | 10:50 AM Dismissal |
| Fri., 10/31 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park, Manchester CT | 2:00 p.m. | 11:00 AM | 10:50 AM Dismissal |
| Fri., 10/31 | JV Field Hockey | Rumsey Hall | Away - Gunnery Turf | 3:00 p.m. | 2:25 PM | |
| Sat., 11/1 | V Football | Bullard/Kolbe | Away - Bullard-Havens Football Field [Directions] | L 6-44 | ||
| Mon., 11/3 | JV Football | Bullard/Kolbe | Home - Pop Warner Field [Directions] | 2:45 p.m. | ||
| Mon., 11/3 | V Field Hockey | Northwestern | Home - Joan Gauthey Field [Directions] | 2:00 p.m. | 12:25 PM Dismissal | |
| Tue., 11/4 | V Field Hockey | Stonington | Away - Palmer Field (Turf) [Directions] | 5:00 p.m. | 1:30 PM | 1:20 PM Dismissal |
| Tue., 11/4 | V Girls Soccer | Capital Prep | Away - Global Communications Academy, 85 Edwards St., Hartford [Directions] | W 8-0 | 11:30 AM | 11:20 AM Dismissal |
| Thu., 11/6 | V Girls Soccer | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | L 2-0 | 3:30 PM | Admission:$5 Adults & $3 Seniors/Students |
| Sat., 11/8 | V Football | Platt Tech | Home - OWTS School Field [Directions] | L 8-28 | ||
| Mon., 11/10 | JV Football | Platt Tech | Away - Platt Tech baseball field [Directions] | Cancelled | ||
| Sat., 11/15 | V Football | O'Brien Tech | Away - O'Brien Tech Athletic Complex [Directions] | W 42-28 | ||
| Mon., 11/17 | JV Football | O'Brien Tech | Home - Torrington HS Turf Field [Directions] | Cancelled | ||
| Sat., 11/29 | V Football | ATI | Home - Municipal Stadium Waterbury [Directions] | L 38-68 | ||
| Sat., 11/29 | V Girls Basketball | Staples (Scrim.) | Away - Staples H.S. Gym [Directions] | 11:00 a.m. | 9:30 AM | |
| Wed., 12/3 | V Girls Basketball | Woodland (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 12/5 | V Boys Ice Hockey | South Kent (Scrim.) | Home - Gunnery Rink [Directions] | 8:00 p.m. | ||
| Sat., 12/6 | V Boys Basketball | Plainville (Scrim.) | Away - Wood Gymnasium [Directions] | 3:00 p.m. | 1:15 PM | |
| Mon., 12/8 | V Girls Basketball | Wolcott Tech (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 12/9 | V Boys Basketball | Brookfield (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 12/9 | JV Boys Basketball | Brookfield (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/10 | V Boys Ice Hockey | Shepaug Jamboree | Home - Gunnery Rink [Directions] | 7:00 p.m. | ||
| Thu., 12/11 | V Competitive Cheerleading | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Thu., 12/11 | V Girls Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | W 34-27 | ||
| Fri., 12/12 | V Boys Basketball | Wolcott Tech (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 4:15 p.m. | ||
| Fri., 12/12 | V Boys Ice Hockey | South Kent (Scrim.) | Away | 7:30 p.m. | 6:00 PM | |
| Fri., 12/12 | V Boys Swimming and Diving | Berkshire League Relays | Home - Shepaug Valley High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 12/12 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 24-36 | 4:00 PM | |
| Tue., 12/16 | V Competitive Cheerleading | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Tue., 12/16 | V Girls Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | W 35-26 | ||
| Wed., 12/17 | V Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | W 78-53 | 4:00 PM | |
| Wed., 12/17 | JV Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | 4:00 PM | |
| Wed., 12/17 | FR Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Wed., 12/17 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | L 2-9 | 5:45 PM | |
| Fri., 12/19 | V Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | L 40-63 | 4:30 PM | |
| Fri., 12/19 | JV Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 5:30 p.m. | 4:30 PM | |
| Fri., 12/19 | FR Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 12/19 | V Boys Swimming and Diving | Lewis Mills | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 12/19 | V Competitive Cheerleading | Litchfield | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Fri., 12/19 | V Girls Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | W 51-35 | ||
| Sat., 12/20 | V Boys Ice Hockey | Housatonic Coop | Away - Hotchkiss [Directions] | W 3-2 | 6:15 PM | |
| Mon., 12/22 | V Boys Ice Hockey | Mt. Everett (MA) | Home - Gunnery Rink [Directions] | L 4-5 OT | ||
| Mon., 12/22 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 12/23 | V Boys Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | L 48-75 | Alumni Night | |
| Tue., 12/23 | JV Boys Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/23 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | L 4-5 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 12/23 | V Competitive Cheerleading | Terryville | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Tue., 12/23 | V Girls Basketball | Terryville | Away - New Terryville High School [Directions] | W 49-38 | 4:15 PM | |
| Sat., 12/27 | V Boys Basketball | O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | W 79-60 | ||
| Sat., 12/27 | JV Boys Basketball | O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | 1:30 p.m. | ||
| Sat., 12/27 | V Competitive Cheerleading | O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | 3:00 p.m. | Boys Basketball Game | |
| Mon., 12/29 | V Competitive Cheerleading | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | 12:30 p.m. | Girls Basketball Game | |
| Mon., 12/29 | V Girls Basketball | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | W 53-11 | ||
| Fri., 1/2 | V Boys Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | L 77-94 | ||
| Fri., 1/2 | JV Boys Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/2 | V Boys Ice Hockey | E.O. Smith-Tolland | Home - Gunnery Rink [Directions] | L 0-7 | ||
| Fri., 1/2 | V Competitive Cheerleading | Northwestern | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 1/2 | V Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | W 40-38 | 4:00 PM | |
| Sat., 1/3 | FR Boys Basketball | O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | 10:00 a.m. | ||
| Tue., 1/6 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | L 42-59 | 4:30 PM | |
| Tue., 1/6 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | 4:30 PM | |
| Tue., 1/6 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/6 | V Competitive Cheerleading | Thomaston | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Tue., 1/6 | V Girls Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | L 37-69 | ||
| Wed., 1/7 | JV Girls Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 1/9 | V Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | L 40-71 | ||
| Fri., 1/9 | JV Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/9 | FR Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/9 | V Competitive Cheerleading | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 1/9 | V Girls Basketball | Gilbert | Away - Gilbert Gym [Directions] | W 50-32 | 4:00 PM | |
| Tue., 1/13 | V Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | W 60-53 | ||
| Tue., 1/13 | JV Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/13 | FR Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 1/13 | V Boys Swimming and Diving | Wamogo | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/13 | V Competitive Cheerleading | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Tue., 1/13 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | W 42-40 | 4:30 PM | |
| Wed., 1/14 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | L 2-4 | 1:15 PM | |
| Wed., 1/14 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 5:00 p.m. | 3:15 PM | |
| Fri., 1/16 | V Boys Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | L 42-67 | ||
| Fri., 1/16 | JV Boys Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/16 | V Competitive Cheerleading | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Fri., 1/16 | V Competitive Cheerleading | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 1/16 | V Girls Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | L 23-43 | ||
| Sat., 1/17 | V Boys Swimming and Diving | Lewis Mills | Away - Giamatti Center - Bristol [Directions] | 6:45 p.m. | 5:15 PM | |
| Tue., 1/20 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 35-67 | 4:00 PM | |
| Tue., 1/20 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Tue., 1/20 | FR Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 1/20 | V Competitive Cheerleading | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Tue., 1/20 | V Girls Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | L 36-46 | ||
| Wed., 1/21 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | W 7-5 | 3:45 PM | |
| Wed., 1/21 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 2 (Small Gym) [Directions] | 5:15 p.m. | 4:15 PM | |
| Thu., 1/22 | V Boys Swimming and Diving | Gilbert | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 1/23 | V Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | W 62-53 | ||
| Fri., 1/23 | JV Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/23 | FR Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/23 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | L 0-3 | 6:30 PM | |
| Fri., 1/23 | V Competitive Cheerleading | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball | |
| Fri., 1/23 | V Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | L 28-43 | 4:00 PM | |
| Mon., 1/26 | FR Boys Basketball | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | Cancelled | ||
| Wed., 1/28 | JV Girls Basketball | Housatonic Regional | Away - Housatonic [Directions] | 5:30 p.m. | 4:00 PM | |
| Thu., 1/29 | V Boys Basketball | Terryville | Away - eli terry middle school [Directions] | L 52-86 | 4:15 PM | |
| Thu., 1/29 | JV Boys Basketball | Terryville | Away - Eli terry Middle school [Directions] | 5:30 p.m. | 4:15 PM | |
| Thu., 1/29 | V Girls Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | W 34-21 | 3:00 PM | |
| Fri., 1/30 | V Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | W 63-41 | 3:00 PM | |
| Fri., 1/30 | JV Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 4:30 p.m. | 3:00 PM | |
| Fri., 1/30 | FR Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 1/30 | V Boys Ice Hockey | New Fairfield | Home - Gunnery Rink [Directions] | L 0-3 | ||
| Fri., 1/30 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/3 | V Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | L 48-65 | ||
| Tue., 2/3 | JV Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/3 | FR Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 2/3 | V Boys Swimming and Diving | Housatonic Regional | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/3 | V Competitive Cheerleading | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Tue., 2/3 | V Girls Basketball | Litchfield | Away - Litchfield High School [Directions] | W 49-40 | 4:30 PM | |
| Wed., 2/4 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School | W 5-1 | 5:30 PM | |
| Fri., 2/6 | V Boys Ice Hockey | Lyman Hall | Home - Gunnery Rink [Directions] | W 4-3(OT) | ||
| Fri., 2/6 | V Competitive Cheerleading | Terryville | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Fri., 2/6 | V Girls Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | W 34-13 | ||
| Sat., 2/7 | V Boys Ice Hockey | Eastern CT Eagles | Home - Gunnery Rink [Directions] | W 6-3 | ||
| Sat., 2/7 | V Boys Swimming and Diving | SPLISH | Home - Shepaug Valley High School Pool [Directions] | 11:00 a.m. | ||
| Sat., 2/7 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 4:30 p.m. | 2:45 PM | |
| Tue., 2/10 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | L 39-67 | 4:00 PM | |
| Tue., 2/10 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Tue., 2/10 | V Boys Swimming and Diving | Avon | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/10 | V Competitive Cheerleading | Northwestern | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Tue., 2/10 | V Girls Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | W 40-31 | ||
| Wed., 2/11 | V Boys Ice Hockey | Hall | Away - Veteran's Memorial Rink [Directions] | W 3-2 OT | 5:00 PM | |
| Wed., 2/11 | JV Girls Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 2/13 | V Boys Basketball | Nonnewaug | Away - Nonnewaug High School [Directions] | L 41-70 | 4:15 PM | |
| Fri., 2/13 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug High School [Directions] | 4:00 p.m. | 2:45 PM | |
| Fri., 2/13 | V Boys Ice Hockey | Sheehan | Home - Gunnery Rink [Directions] | W 7-3 | ||
| Fri., 2/13 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 7:30 p.m. | 5:45 PM | |
| Fri., 2/13 | V Girls Basketball | Nonnewaug | Away - Nonnewaug High School [Directions] | L 24-47 | 4:15 PM | |
| Tue., 2/17 | V Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | W 59-52 | 4:00 PM | |
| Tue., 2/17 | JV Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Tue., 2/17 | FR Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 2/17 | V Competitive Cheerleading | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Tue., 2/17 | V Girls Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | W 62-58 | ||
| Wed., 2/18 | FR Boys Basketball | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/18 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena [Directions] | W 4-3 | 3:45 PM | |
| Wed., 2/18 | V Boys Swimming and Diving | Northwestern | Home - Shepaug Valley High School Pool [Directions] | 5:00 p.m. | ||
| Thu., 2/19 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | L 24-53 | 5:45 PM | |
| Fri., 2/20 | V Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | W 64-59 | ||
| Fri., 2/20 | JV Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 5:45 p.m. | ||
| Fri., 2/20 | FR Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 4:15 p.m. | ||
| Fri., 2/20 | V Boys Ice Hockey | Danbury | Home - Gunnery Rink [Directions] | W 4-2 | ||
| Fri., 2/20 | V Competitive Cheerleading | Thomaston | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Sat., 2/21 | V Girls Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 12:00 p.m. | BL Tourney - No Passes accepted | |
| Mon., 2/23 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | W 58-50 | 4:30 PM | |
| Mon., 2/23 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | 4:30 PM | |
| Mon., 2/23 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | Cancelled | 2:25 PM | |
| Mon., 2/23 | V Boys Ice Hockey | JBWA | Home - Gunnery Rink [Directions] | L 2-5 | ||
| Mon., 2/23 | V Boys Swimming and Diving | Wamogo | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/24 | JV Boys Ice Hockey | JBWA | Away - Danbury Ice Arena [Directions] | W 4-2 | 6:00 PM | |
| Wed., 2/25 | V Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | L 43-61 | ||
| Wed., 2/25 | JV Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/25 | FR Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 2/25 | V Boys Ice Hockey | New Milford | Home - Gunnery Rink [Directions] | L 3-5 | ||
| Wed., 2/25 | V Competitive Cheerleading | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 2/27 | V Boys Swimming and Diving | Holy Cross | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Sat., 2/28 | V Boys Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 6:00 p.m. | 4:15 PM | |
| Sat., 2/28 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | W 5-3 | 4:45 PM | |
| Sat., 2/28 | V Boys Swimming and Diving | SPLASH Classic | Away - Plainville High School | 2:00 p.m. | 11:00 AM | |
| Sun., 3/1 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Gunnery Rink [Directions] | 1:45 p.m. | ||
| Mon., 3/2 | V Boys Ice Hockey | Housatonic Coop | Home - Gunnery Rink [Directions] | L 3-4(OT) | ||
| Mon., 3/2 | V Girls Basketball | St. Bernard | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | CIAC Tournament Game | |
| Wed., 3/4 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | L 3-5 | 2:45 PM | |
| Sat., 3/7 | V Boys Basketball | East Hampton | Away - East Hampton High School [Directions] | 7:00 p.m. | 3:45 PM | |
| Sat., 3/7 | V Boys Swimming and Diving | Berkshire League Championships | Away - Hotchkiss School | 1:00 p.m. | 9:45 AM | |
| Mon., 3/9 | V Boys Ice Hockey | Danbury | Away - Danbury Ice Arena [Directions] | W 4-2 | 2:45 PM | |
| Thu., 3/12 | V Boys Ice Hockey | Woodstock Academy | Away - Northford Rink, North Haven [Directions] | W 7-5 | 2:45 PM | |
| Thu., 3/12 | V Boys Swimming and Diving | Class S Diving | Away - Plainville High School | 5:30 p.m. | ||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Class S Trials | Away - Plainville High School | 3:30 p.m. | 11:30 AM | |
| Tue., 3/17 | V Boys Ice Hockey | E.O. Smith-Tolland | Away - Ingalls Rink - Yale University [Directions] | 5:30 p.m. | 2:30 PM | |
| Wed., 3/18 | V Boys Swimming and Diving | Class S Finals | Away - Wesleyan University | 1:30 p.m. | 10:15 AM | 9:00 AM Dismissal |
| Thu., 3/19 | V Boys Swimming and Diving | Open Diving Championships | Away - Middletown High School | 5:30 p.m. | TBA | |
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Open Swimming | Away | 2:30 p.m. | TBA | |
| Wed., 4/1 | V Baseball | Torrington (Scrim.) | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 4/2 | V Baseball | New Milford (Scrim.) | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 4/2 | V Boys Tennis | Canton/East Granby Coop (Scrim.) | Home - Shepaug Valley High School Courts [Directions] | L 1-4 | ||
| Thu., 4/2 | V Girls Tennis | Canton (Scrim.) | Away - Mills Pond Park [Directions] | W 7-0 | 2:25 PM | |
| Sat., 4/4 | V Softball | Gunnery (Scrim.) | Home - Dick Ayer Field [Directions] | 1:00 p.m. | ||
| Mon., 4/6 | V Baseball | Torrington (Scrim.) | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Mon., 4/6 | V Girls Tennis | Gunnery (Scrim.) | Away | 4:30 p.m. | TBA | |
| Mon., 4/6 | V Girls Tennis | Gunnery (Scrim.) | Away | W 4-2 | ||
| Wed., 4/8 | V Baseball | Terryville | Home - Ted Alex Field [Directions] | L 1-4 | ||
| Wed., 4/8 | V Boys Tennis | Thomaston | Home - Shepaug Valley High School Courts [Directions] | W 3-2 | ||
| Wed., 4/8 | V Softball | Terryville | Home - Dick Ayer Field [Directions] | W 24-9 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 4/8 | V Girls Tennis | Thomaston | Away - Thomaston Center School [Directions] | W 4-0 | 2:25 PM | |
| Mon., 4/13 | V Baseball | Thomaston | Home - Ted Alex Field [Directions] | L 4-0 | ||
| Mon., 4/13 | V Boys Tennis | Litchfield | Home - Shepaug Valley High School Courts [Directions] | W 3-2 | ||
| Mon., 4/13 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | L 1-10 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 4/13 | V Girls Tennis | Litchfield | Away - Litchfield High School [Directions] | W 4-3 | 2:25 PM | |
| Tue., 4/14 | JV Baseball | Thomaston | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/14 | V Boys Tennis | Nonnewaug | Away - Edgewood Bath & Tennis Club [Directions] | L 1-4 | 2:30 PM | |
| Tue., 4/14 | V Girls Tennis | Nonnewaug | Home - Shepaug Valley High School Courts [Directions] | W 5-2 | ||
| Wed., 4/15 | V Baseball | Gilbert | Away - Walker Field [Directions] | L 6-7 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 4/15 | JV Baseball | Gilbert | Away - Gilbert [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Wed., 4/15 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | W 5-0 | 11:00 AM | |
| Wed., 4/15 | V Girls Tennis | Wamogo | Home - Shepaug Valley High School Courts [Directions] | W 5-2 | ||
| Fri., 4/17 | V Baseball | Litchfield | Home - Ted Alex Field [Directions] | L 4-10 | ||
| Fri., 4/17 | V Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | W 25-0 | 2:25 PM | |
| Tue., 4/21 | V Baseball | Kennedy | Away - Waterville Park [Directions] | W 5-4 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 4/21 | V Boys Outdoor Track | Nonnewaug, Gilbert | Home - Shepaug Valley High School Track [Directions] | 3:45 p.m. | ||
| Tue., 4/21 | V Boys Tennis | Brookfield | Home - Shepaug Valley High School Courts [Directions] | L 1-4 | ||
| Tue., 4/21 | V Girls Outdoor Track | Nonnewaug, Gilbert | Home - Shepaug Valley High School Track [Directions] | 3:45 p.m. | ||
| Tue., 4/21 | V Softball | Gilbert | Home - Dick Ayer Field [Directions] | W 12-2 | ||
| Thu., 4/23 | V Boys Outdoor Track | Northwestern | Away - Northwestern HS [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Thu., 4/23 | V Boys Tennis | Northwestern | Home - Shepaug Valley High School Courts [Directions] | L 2-3 | ||
| Thu., 4/23 | V Girls Outdoor Track | Northwestern | Away - Northwestern HS [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Thu., 4/23 | V Softball | Housatonic Regional | Home - Dick Ayer Field [Directions] | W 8-2 | ||
| Thu., 4/23 | V Girls Tennis | Northwestern | Away - Northwestern HS [Directions] | W 4-0 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 4/24 | V Baseball | Northwestern | Away - Northwestern Gym [Directions] | L 1-15 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 4/24 | JV Baseball | Northwestern | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 4/24 | V Boys Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | W 3-2 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 4/24 | V Softball | Northwestern | Home - Dick Ayer Field [Directions] | L 6-11 | ||
| Fri., 4/24 | V Girls Tennis | Lewis Mills | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Mon., 4/27 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | W 5-0 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 4/27 | JV Baseball | Lewis Mills | Away - Lewis Mills JV Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/27 | V Boys Golf | New Milford | Home - Washington Club [Directions] | New Milford 165 Shepaug 178 | ||
| Mon., 4/27 | V Boys Tennis | Housatonic Regional | Home - Shepaug Valley High School Courts [Directions] | L 2-3 | ||
| Mon., 4/27 | V Girls Tennis | Housatonic Regional | Away - High School Courts [Directions] | W 7-0 | 2:25 PM | 1:50 PM Dismissal |
| Mon., 4/27 | Unified Sports Volleyball | Nonnewaug | Away [Directions] | 2:30 p.m. | 2:00 PM | |
| Tue., 4/28 | V Baseball | Housatonic Regional | Away - HVRHS Field [Directions] | W 4-3 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 4/28 | JV Baseball | Housatonic Regional | Away - High School JV Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 4/28 | V Boys Golf | Northwestern, Lewis Mills | Home - Washington Club [Directions] | Lewis Mills 177, Northwestern 180, Shepaug 182 | ||
| Tue., 4/28 | V Boys Outdoor Track | Housatonic Regional, Thomaston | Away - Housatonic Track [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 4/28 | V Boys Tennis | Gilbert | Home - Shepaug Valley High School Courts [Directions] | W 4-1 | ||
| Tue., 4/28 | V Girls Outdoor Track | Housatonic Regional, Thomaston | Away - Housatonic Track [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 4/28 | JV Softball | Nonnewaug | Home - Dick Ayer Field [Directions] | 3:45 p.m. | ||
| Tue., 4/28 | V Girls Tennis | Gilbert | Away - Gilbert [Directions] | W 7-0 | 2:25 PM | 1:50 PM Dismissal |
| Wed., 4/29 | V Baseball | Nonnewaug | Away - Nonnewaug Varsity Baseball Field [Directions] | W 16-5 | 2:25 PM | |
| Wed., 4/29 | JV Baseball | Nonnewaug | Away - Woodbury Middle School [Directions] | 3:45 p.m. | 2:25 PM | |
| Wed., 4/29 | V Boys Tennis | Thomaston | Away - Thomaston Center School [Directions] | L 2-3 | 2:25 PM | |
| Wed., 4/29 | V Softball | Nonnewaug | Home - Dick Ayer Field [Directions] | L 10-7 | ||
| Wed., 4/29 | V Girls Tennis | Thomaston | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Thu., 4/30 | V Baseball | Wamogo | Home - Ted Alex Field [Directions] | W 5-4 | 2:25 PM | |
| Thu., 4/30 | JV Baseball | Wamogo | Away - Wamogo [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 4/30 | V Boys Golf | Housatonic Regional | Away - Canaan Country Club [Directions] | Shepaug 175, Housatonic 180 | 1:40 PM | 1:30 PM Dismissal |
| Thu., 4/30 | V Boys Tennis | Gilbert | Away - Gilbert [Directions] | W 3-2 | 2:25 PM | |
| Thu., 4/30 | V Softball | Wamogo/Litchfield | Away - Wamogo Varsity Softball Field [Directions] | L 1-10 | 2:25 PM | |
| Thu., 4/30 | V Girls Tennis | Gilbert | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Sat., 5/2 | V Boys Outdoor Track | Torrington Track and Field Challenge | Away | 3:30 p.m. | 1:00 pm | |
| Sat., 5/2 | V Girls Outdoor Track | Torrington Track and Field Challenge | Away - Torrington High School | 3:30 p.m. | 1:00 PM | |
| Mon., 5/4 | V Baseball | Terryville | Away - New Terryville High School [Directions] | L 21-6 | 2:15 PM | 2:05 PM Dismissal |
| Mon., 5/4 | JV Baseball | Terryville | Away - Lower Fisher Elementary [Directions] | 3:45 p.m. | 2:15 PM | 2:05 PM Dismissal |
| Mon., 5/4 | V Boys Golf | Nonnewaug, Terryville | Away - Heritage Village CC [Directions] | Nonnewaug 183, Shepaug 188, Terryville 240 | 2:45 PM | |
| Mon., 5/4 | V Boys Tennis | Litchfield | Away - Litchfield High School [Directions] | W 3-2 | 2:25 PM | |
| Mon., 5/4 | V Softball | Terryville | Away - New Terryville High School [Directions] | W 18-3 | ||
| Mon., 5/4 | V Girls Tennis | Litchfield | Home - Shepaug Valley High School Courts [Directions] | W 4-3 | ||
| Tue., 5/5 | V Boys Golf | Northwestern, Wamogo | Away - Norfolk CC [Directions] | Shepaug 170, Northwestern 176, Wamogo 185 | 1:45 PM | 1:35 PM Dismissal |
| Tue., 5/5 | V Boys Outdoor Track | Litchfield, Northwestern, Terryville | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 5/5 | V Girls Outdoor Track | Litchfield, Northwestern, Terryville | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | 2:25 PM | |
| Wed., 5/6 | V Baseball | Lewis Mills | Home - Ted Alex Field [Directions] | W 6-0 | ||
| Wed., 5/6 | JV Baseball | Lewis Mills | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/6 | V Boys Golf | Gilbert, Housatonic Regional | Away - Greenwood Country Club [Directions] | Cancelled | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/6 | V Boys Tennis | Nonnewaug | Home - Shepaug Valley High School Courts [Directions] | L 1-4 | ||
| Wed., 5/6 | V Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | W 19-5 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/6 | V Girls Tennis | Nonnewaug | Away - Edgewood Bath & Tennis Club [Directions] | W 7-0 | 2:25 PM | |
| Thu., 5/7 | V Boys Golf | Woodland Invitational | Away - Oxford Greens | Shepaug 185 | ||
| Thu., 5/7 | JV Softball | Northwestern | Away - Northwestern JV field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 5/8 | V Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | L 8-7 | 2:25 PM | |
| Fri., 5/8 | JV Baseball | Thomaston | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 5/8 | V Boys Outdoor Track | Irv Black Invitational | Away - Willowbrook Park, New Britain | 3:30 p.m. | 1:30 PM Dismissal | |
| Fri., 5/8 | V Boys Tennis | Wamogo | Home - Shepaug Valley High School Courts [Directions] | W 3-2 | ||
| Fri., 5/8 | V Girls Outdoor Track | Irv Black Invitational | Away - Willowbrook Park, New Britain | 3:30 p.m. | 1:30 PM Dismissal | |
| Fri., 5/8 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | W 7-0 | 2:25 PM | |
| Sat., 5/9 | V Boys Outdoor Track | Irv Black Invitational | Away - Willowbrook Park, New Britain | 10:00 a.m. | 8:00 AM | |
| Sat., 5/9 | V Girls Outdoor Track | Irv Black Invitational | Home - Willowbrook Park, New Britain [Directions] | 10:00 a.m. | 8:00 AM | |
| Mon., 5/11 | V Baseball | Gilbert | Home - Ted Alex Field [Directions] | W 9-1 | ||
| Mon., 5/11 | JV Baseball | Litchfield | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/11 | V Boys Golf | Gilbert, Housatonic Regional, Northwestern | Away - Greenwood Country Club [Directions] | Shepaug 183, Housatonic 200, Gilbert 263 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 5/11 | V Boys Outdoor Track | Wamogo, Lewis Mills | Home - Shepaug Valley High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/11 | V Boys Tennis | Northwestern | Away - Northwestern HS [Directions] | L 2-3 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 5/11 | V Girls Outdoor Track | Wamogo, Lewis Mills | Home - Shepaug Valley High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/11 | V Softball | Gilbert | Away - Walker Field [Directions] | W 20-5 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 5/11 | V Girls Tennis | Northwestern | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Tue., 5/12 | JV Baseball | Litchfield | Away - Community Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Tue., 5/12 | V Boys Tennis | Abbott Tech | Away - Abbott Technical HS Tennis Complex [Directions] | W 6-1 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/13 | V Baseball | Litchfield | Away - Litchfield HS Baseball Field [Directions] | L 6-7(8) | 2:25 PM | |
| Wed., 5/13 | V Softball | Litchfield | Home - Dick Ayer Field [Directions] | W 27-4 | ||
| Thu., 5/14 | V Boys Golf | Litchfield, Nonnewaug | Home - Lake Waramaug Country Club [Directions] | Litchfield 180, Nonnewaug 183, Shepaug 185 | ||
| Fri., 5/15 | V Boys Tennis | Lewis Mills | Home - Shepaug Valley High School Courts [Directions] | L 2-3 | ||
| Fri., 5/15 | V Softball | Thomaston | Home - Dick Ayer Field [Directions] | L 6-2 | ||
| Fri., 5/15 | V Girls Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | W 5-2 | 2:00 PM | 1:50 PM Dismissal |
| Sat., 5/16 | V Boys Outdoor Track | Berkshire League Championship | Away - Litchfield High School | 9:00 a.m. | 7:15 AM | |
| Sat., 5/16 | V Girls Outdoor Track | Berkshire League Championship | Away - Litchfield High School | 9:00 a.m. | 7:15 AM | |
| Sat., 5/16 | V Softball | Lewis Mills | Home - Dick Ayer Field [Directions] | W 12-3 | ||
| Sat., 5/16 | JV Softball | Lewis Mills | Home - Dick Ayer Field [Directions] | 2:45 p.m. | ||
| Mon., 5/18 | V Baseball | Housatonic Regional | Home - Ted Alex Field [Directions] | L 2-0 | ||
| Mon., 5/18 | JV Baseball | Housatonic Regional | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/18 | V Boys Golf | Litchfield, Wamogo | Away - Litchfield Country Club [Directions] | Litchfield 170, Shepaug 184, Wamogo 194 | 2:30 PM | 2:20 PM Dismissal |
| Mon., 5/18 | V Boys Tennis | Housatonic Regional | Away - High School Courts [Directions] | L 1-4 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 5/18 | V Softball | Housatonic Regional | Away - HVRHS Field [Directions] | L 1-8 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 5/18 | V Girls Tennis | Housatonic Regional | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Tue., 5/19 | V Boys Golf | Terryville, Gilbert | Home - Lake Waramaug Country Club [Directions] | Shepaug 189, Terryville 223, Gilbert (forfeit) | ||
| Tue., 5/19 | V Boys Outdoor Track | Berkshire League Festival | Away - Housatonic Valley Regional | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 5/19 | V Girls Outdoor Track | Berkshire League Festival | Away - Housatonic Valley Regional | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 5/19 | V Girls Tennis | Berkshire League All-Star Tournament | Away | 11:00 a.m. | 9:15 am | 9:05 AM Dismissal |
| Wed., 5/20 | V Baseball | Northwestern | Home - Ted Alex Field [Directions] | W 8-2 | ||
| Wed., 5/20 | JV Baseball | Northwestern | Away - Northwestern HS [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/20 | V Boys Golf | Lewis Mills | Away - Fairview Farms Golf Course - Harwinton [Directions] | Lewis Mills 173, Shepaug 196 | 1:50 PM | 1:40 PM Dismissal |
| Wed., 5/20 | V Boys Outdoor Track | Berkshire League Festival | Away - Housatonic Valley Regional | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/20 | V Girls Outdoor Track | Berkshire League Festival | Away - Housatonic Valley Regional | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/20 | V Softball | Northwestern | Away - Northwestern Varsity Field [Directions] | L 0-15 | 2:00 PM | 1:50 PM Dismissal |
| Thu., 5/21 | V Baseball | Kennedy | Home - Ted Alex Field [Directions] | W 6-1 | ||
| Thu., 5/21 | JV Baseball | Gilbert | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/21 | V Boys Tennis | Berkshire League All-Star Tournament | Away | 11:00 a.m. | 9:15 AM | 9:05 AM Dismissal |
| Thu., 5/21 | V Softball | O'Brien Tech | Home - Dick Ayer Field [Directions] | W 16-1 | 1:45 PM Dismissal | |
| Thu., 5/21 | V Softball | O'Brien Tech | Home - Dick Ayer Field [Directions] | W 19-4 | 1:45 PM Dismissal | |
| Mon., 5/25 | V Baseball | Nonnewaug | Home - Ted Alex Field [Directions] | W 5-3 | ||
| Tue., 5/26 | JV Baseball | Nonnewaug | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/26 | V Boys Golf | Berkshire League All-Star | Away - Fairview Farm Golf Course | 8:00 a.m. | ||
| Tue., 5/26 | V Boys Tennis | BL All-Star Tournament | Away - Hotchkiss School Indoor Courts | 3:00 p.m. | 1:30 PM | 1:20 PM Dismissal |
| Tue., 5/26 | V Softball | Nonnewaug | Away - Nonnewaug Varsity Softball Field [Directions] | L 6-3 | 2:25 PM | |
| Wed., 5/27 | V Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | L 7-5 | 2:25 PM | |
| Wed., 5/27 | V Softball | Wamogo/Litchfield | Home - Dick Ayer Field [Directions] | L 2-6 | ||
| Thu., 5/28 | JV Baseball | Wamogo | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 5/28 | V Girls Tennis | Brookfield | Home - Shepaug Valley High School Courts [Directions] | W 4-3 | ||
| Sat., 5/30 | V Boys Tennis | CIAC Class S Championship | Away - Conard High School, West Hartford | 8:30 a.m. | ||
| Mon., 6/1 | V Girls Tennis | Old Lyme | Home - Rumsey Hall Indoor Courts [Directions] | 3:00 p.m. | 1:30 PM Dismissal | |
| Wed., 6/3 | V Baseball | Old Lyme | Away - Old Lyme High School [Directions] | 3:30 p.m. | 12:30 PM | 12:25 PM Dismissal |
| Wed., 6/3 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willowbrook Park | 12:00 p.m. | 10:00 AM | 9:50 AM Dismissal |
| Wed., 6/3 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willowbrook Park | 12:00 p.m. | 10:00 AM | 9:50 AM Dismissal |
| Wed., 6/3 | V Softball | Stafford | Away - Stafford High [Directions] | 3:00 p.m. | 12:00 PM | 11:50 PM Dismissal |
| Sat., 6/6 | V Girls Tennis | CIAC Individual Tournament | Away | TBA | TBA | |
| Mon., 6/8 | V Boys Golf | CIAC Div. IV Championship | Away - Tallwood CC - Hebron [Directions] | TBA | ||
| Mon., 6/8 | V Boys Outdoor Track | CIAC State Open | Away - Willowbrook Park | 1:30 p.m. | 11:15 AM | 11:05 AM Dismissal |
| Mon., 6/8 | V Girls Outdoor Track | CIAC State Open | Away - Willowbrook Park | 1:30 p.m. | 11:15 AM | 11:05 AM Dismissal |
| Mon., 6/22 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||