| Shepaug Valley 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 535 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Nonnewaug | Home - Shepaug Valley HS JV Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | TBA | ||
| TBA | JV Football | Cheney Tech | Away - Cheney Tech [Directions] | 6:00 p.m. | ||
| TBA | JV Girls Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| TBA | Unified Sports Volleyball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 2:45 p.m. | ||
| Fri., 7/3 | School Holidays and Closings | Independence Day observed | ||||
| Sat., 7/4 | School Holidays and Closings | Independence Day | ||||
| Sat., 8/29 | JV Football | Platt Tech (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Mon., 8/31 | V Girls Soccer | Sacred Heart (Scrim.) | Away - Bucks Hill Park | Cancelled | Cancelled | |
| Thu., 9/3 | V Boys Soccer | Danbury (Scrim.) | Away - Danbury HS Stadium [Directions] | 7:00 p.m. | ||
| Thu., 9/3 | V Field Hockey | New Milford (Scrim.) | Away - New Milford HS [Directions] | Cancelled | Cancelled | |
| Thu., 9/3 | V Girls Soccer | Brookfield (Scrim.) | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 9/5 | V Field Hockey | Brookfield Play Day | Away | Cancelled | Cancelled | |
| Sat., 9/5 | JV Field Hockey | Brookfield Play Day | Away | 9:00 a.m. | ||
| Mon., 9/7 | School Holidays and Closings | Labor Day | ||||
| Thu., 9/10 | V Boys Cross Country | Berkshire League Scrimmage | Away - Black Rock Park | 4:15 p.m. | ||
| Thu., 9/10 | V Girls Cross Country | Berkshire League Scrimmage | Away - Black Rock Park | 4:15 p.m. | ||
| Fri., 9/11 | V Boys Soccer | Housatonic Regional | Away - Housatonic Field [Directions] | 3:45 p.m. | L 0-1 | 1:50 PM Dismissal |
| Fri., 9/11 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Field [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Fri., 9/11 | V Field Hockey | Thomaston | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 9/11 | JV Field Hockey | Thomaston | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Fri., 9/11 | V Girls Soccer | Housatonic Regional | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 9/11 | JV Girls Soccer | Housatonic Regional | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 9/12 | School Holidays and Closings | ACT Testing Date | ||||
| Mon., 9/14 | JV Football | Capital/Achievement | Home - Torrington Pop Warner Field [Directions] | 4:00 p.m. | W 22-20 | |
| Tue., 9/15 | V Boys Cross Country | Gilbert, Lewis Mills | Away - Gilbert [Directions] | 4:15 p.m. | 1:50 PM | |
| Tue., 9/15 | V Boys Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-1 | 1:50 PM Dismissal |
| Tue., 9/15 | JV Boys Soccer | Northwestern | Away - Northwestern JV field [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Tue., 9/15 | V Girls Cross Country | Gilbert, Lewis Mills | Away - Gilbert [Directions] | 4:15 p.m. | 1:50 PM Dismissal | |
| Tue., 9/15 | V Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 3:45 p.m. | W 1-0(OT) | 1:50 PM Dismissal |
| Tue., 9/15 | JV Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 5:00 p.m. | 1:50 PM Dismissal | |
| Tue., 9/15 | V Girls Soccer | Northwestern | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 9/15 | JV Girls Soccer | Northwestern | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/17 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 4:00 p.m. | L 0-1 | 1:50 PM Dismissal |
| Thu., 9/17 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 5:30 p.m. | 1:50 PM Dismissal | |
| Fri., 9/18 | V Boys Soccer | Lewis Mills | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 5-0 | |
| Fri., 9/18 | JV Boys Soccer | Lewis Mills | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/18 | V Field Hockey | Housatonic Regional | Away - Housatonic Field [Directions] | 3:45 p.m. | W 6-0 | 1:50 PM Dismissal |
| Fri., 9/18 | V Girls Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | 6:00 p.m. | L 0-8 | 2:05 PM Dismissal |
| Fri., 9/18 | JV Girls Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | 4:00 p.m. | 2:05 PM Dismissal | |
| Sat., 9/19 | V Boys Cross Country | Wilton Invitational | Away | 9:30 a.m. | ||
| Sat., 9/19 | V Girls Cross Country | Wilton Invitational | Away - Allens Meadows Park, Wilton | 9:30 a.m. | ||
| Mon., 9/21 | JV Football | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 4:00 p.m. | L 0-20 | |
| Mon., 9/21 | V Boys Soccer | Litchfield | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 3-2 | |
| Mon., 9/21 | JV Boys Soccer | Litchfield | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/21 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | L 1-2 | |
| Mon., 9/21 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| Tue., 9/22 | V Boys Cross Country | Litchfield, Gilbert, Terryville | Away - Plumb Hill Field Complex [Directions] | 4:00 p.m. | 1:50 PM | |
| Tue., 9/22 | V Girls Cross Country | Litchfield, Gilbert, Terryville | Away - Plumb Hill Field Complex [Directions] | 4:00 p.m. | ||
| Tue., 9/22 | V Field Hockey | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | W 2-1 | 1:50 PM Dismissal |
| Tue., 9/22 | JV Field Hockey | Northwestern | Away - Northwestern Field [Directions] | 5:00 p.m. | 1:50 PM Dismissal | |
| Thu., 9/24 | V Boys Soccer | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | L 1-2 | 2:05 PM Dismissal |
| Thu., 9/24 | JV Boys Soccer | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | 2:05 PM Dismissal | |
| Thu., 9/24 | V Field Hockey | Nonnewaug | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | W 1-0 | |
| Thu., 9/24 | JV Field Hockey | Nonnewaug | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Thu., 9/24 | V Girls Soccer | Terryville | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-2 | |
| Thu., 9/24 | JV Girls Soccer | Terryville | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 9/26 | V Boys Cross Country | Winding Trails Invitational | Away - Winding Trails Center, Farmington | 9:00 a.m. | ||
| Sat., 9/26 | V Girls Cross Country | Winding Trails Invitational | Away - Winding Trails Center, Farmington | 9:00 a.m. | ||
| Mon., 9/28 | JV Football | Bassick | Home - Torrington Pop Warner Field [Directions] | 4:00 p.m. | L 18-24 | |
| Tue., 9/29 | V Boys Cross Country | Thomaston, Housatonic Regional | Home - Shepaug Valley HS [Directions] | 4:15 p.m. | ||
| Tue., 9/29 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | L 3-2 | 1:50 PM Dismissal |
| Tue., 9/29 | JV Boys Soccer | Gilbert | Away - Rowley Field [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Tue., 9/29 | V Girls Cross Country | Thomaston, Housatonic Regional | Home - Shepaug Valley HS [Directions] | 4:15 p.m. | ||
| Tue., 9/29 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 9/29 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | Cancelled | Cancelled | |
| Tue., 9/29 | V Girls Soccer | Gilbert | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 10/1 | V Girls Soccer | Nonnewaug | Away [Directions] | 3:45 p.m. | L 4-0 | |
| Thu., 10/1 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Boys Cross Country | Nonnewaug Invitational | Away [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Boys Soccer | Nonnewaug | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 3-0 | |
| Fri., 10/2 | JV Boys Soccer | Nonnewaug | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Girls Cross Country | Nonnewaug Invitational | Away [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 10/2 | JV Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | Cancelled | Cancelled | |
| Sat., 10/3 | School Holidays and Closings | SAT Testing Date | ||||
| Tue., 10/6 | V Boys Cross Country | Terryville, Wamogo, Housatonic Regional | Home - Shepaug Valley HS [Directions] | 4:15 p.m. | ||
| Tue., 10/6 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 10/6 | JV Boys Soccer | Wamogo | Away - Wamogo Regional HS [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Terryville, Wamogo, Housatonic Regional | Home - Shepaug Valley HS [Directions] | 4:15 p.m. | ||
| Tue., 10/6 | V Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 10/6 | JV Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | 5:00 p.m. | ||
| Tue., 10/6 | V Girls Soccer | Wamogo | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | T 2-2 | |
| Tue., 10/6 | JV Girls Soccer | Wamogo | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/7 | JV Football | Connecticut Junior Republic (Scrim.) | Away | 3:45 p.m. | L 30-38 | |
| Fri., 10/9 | JV Boys Soccer | Thomaston | Home - Shepaug Valley HS JV Soccer Field [Directions] | TBA | ||
| Fri., 10/9 | School Holidays and Closings | No School, Professional Development | ||||
| Sat., 10/10 | V Boys Cross Country | Wickham Invitational | Away | 11:30 a.m. | ||
| Sat., 10/10 | V Boys Soccer | Thomaston | Home - Shepaug Valley Varsity Soccer Field [Directions] | 7:00 p.m. | W 1-0 | |
| Sat., 10/10 | V Girls Cross Country | Wickham Invitational | Away | 11:30 a.m. | ||
| Sat., 10/10 | V Girls Soccer | Thomaston | Home - Shepaug Valley Varsity Soccer Field [Directions] | 5:00 p.m. | W 4-0 | |
| Sun., 10/11 | School Holidays and Closings | SAT Testing Date | ||||
| Mon., 10/12 | JV Football | Creed | Home - Wolcott Tech Football Field [Directions] | 1:00 p.m. | W 26-14 | |
| Mon., 10/12 | JV Football | Platt Tech | Home - Wolcott Tech Football Field [Directions] | Cancelled | Cancelled | |
| Mon., 10/12 | School Holidays and Closings | Columbus Day | ||||
| Tue., 10/13 | V Boys Soccer | Housatonic Regional | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 10/13 | JV Boys Soccer | Housatonic Regional | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/13 | V Field Hockey | Housatonic Regional | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 10/13 | V Girls Soccer | Housatonic Regional | Away - HS Field [Directions] | 6:30 p.m. | L 6-0 | |
| Tue., 10/13 | JV Girls Soccer | Housatonic Regional | Away - HS Field [Directions] | 4:30 p.m. | ||
| Wed., 10/14 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 10/15 | V Boys Cross Country | Nonnewaug, Northwestern | Away - Nonnewaug HS Field [Directions] | 4:15 p.m. | 1:50 PM | |
| Thu., 10/15 | V Boys Soccer | Northwestern | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | T 0-0 | |
| Thu., 10/15 | JV Boys Soccer | Northwestern | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | V Girls Cross Country | Nonnewaug, Northwestern | Away - Nonnewaug HS [Directions] | 4:15 p.m. | ||
| Thu., 10/15 | V Girls Soccer | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | W 2-1 | 1:50 PM Dismissal |
| Thu., 10/15 | JV Girls Soccer | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Fri., 10/16 | JV Field Hockey | Rumsey Hall | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | ||
| Mon., 10/19 | JV Football | Lewis Mills | Home - Torrington Pop Warner Field [Directions] | 3:45 p.m. | W 48-28 | |
| Mon., 10/19 | JV Field Hockey | Brookfield | Away - BHS Field Hockey Field [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Boys Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | 6:00 p.m. | L 0-7 | 2:05 PM Dismissal |
| Tue., 10/20 | JV Boys Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | 4:00 p.m. | 2:05 PM Dismissal | |
| Tue., 10/20 | V Field Hockey | Northwestern | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/20 | JV Field Hockey | Northwestern | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Lewis Mills | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 5-0 | |
| Tue., 10/20 | JV Girls Soccer | Lewis Mills | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/21 | V Field Hockey | Lewis Mills | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | L 1-2 | |
| Wed., 10/21 | JV Field Hockey | Lewis Mills | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Wed., 10/21 | School Holidays and Closings | Early Release, Parent/Teacher Conferences | ||||
| Thu., 10/22 | V Boys Cross Country | Berkshire League Championship | Away | 3:30 p.m. | JV Meet 2:30 PM, 12:30 Dismissal | |
| Thu., 10/22 | V Girls Cross Country | Berkshire League Championship | Away - Black Rock State Park, Thomaston | 4:15 p.m. | 12:30 PM Dismissal | |
| Thu., 10/22 | School Holidays and Closings | Early Release, Parent/Teacher Conferences | ||||
| Fri., 10/23 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 10/23 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| Fri., 10/23 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS [Directions] | 3:45 p.m. | L 2-3 | |
| Fri., 10/23 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS Field [Directions] | 5:15 p.m. | ||
| Fri., 10/23 | V Girls Soccer | Litchfield | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/23 | JV Girls Soccer | Litchfield | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/23 | School Holidays and Closings | Early Release, Parent/Teacher Conferences | ||||
| Mon., 10/26 | JV Football | VGW Techs | Away - Vinal Tech Field [Directions] | Cancelled | Cancelled | |
| Tue., 10/27 | V Boys Soccer | Terryville | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 10/27 | JV Boys Soccer | Terryville | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/27 | V Field Hockey | Litchfield | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 10/27 | JV Field Hockey | Litchfield | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/27 | V Girls Soccer | Terryville | Away [Directions] | 3:45 p.m. | L 3-0 | 2:05 PM Dismissal |
| Tue., 10/27 | JV Girls Soccer | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | 2:05 PM Dismissal | |
| Fri., 10/30 | V Boys Soccer | Wamogo | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-3 | |
| Fri., 10/30 | JV Boys Soccer | Wamogo | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/30 | V Field Hockey | Wamogo | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | W 4-0 | |
| Fri., 10/30 | JV Field Hockey | Wamogo | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Fri., 10/30 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/30 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS [Directions] | 3:15 p.m. | ||
| Sat., 10/31 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park - East Hartford [Directions] | 12:00 p.m. | ||
| Sat., 10/31 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park - East Hartford [Directions] | 11:25 a.m. | ||
| Sat., 10/31 | School Holidays and Closings | Halloween | ||||
| Mon., 11/2 | JV Football | Bullard/Kolbe | Away - Bullard Havens [Directions] | 2:30 p.m. | L 8-28 | |
| Tue., 11/3 | V Boys Soccer | Nonnewaug | Away - NHS - Varsity Soccer Field [Directions] | 3:15 p.m. | L 7-0 | 2:05 PM Dismissal |
| Tue., 11/3 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | 3:15 p.m. | 2:05 PM Dismissal | |
| Tue., 11/3 | V Girls Soccer | Nonnewaug | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:15 p.m. | L 3-0 | 2:05 PM Dismissal |
| Tue., 11/3 | JV Girls Soccer | Nonnewaug | Home - Shepaug Valley HS JV Soccer Field [Directions] | 3:15 p.m. | 2:05 PM Dismissal | |
| Thu., 11/5 | V Field Hockey | New Milford (Scrim.) | Home - Joan Gauthey Field [Directions] | 3:15 p.m. | ||
| Fri., 11/6 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | 10:50 AM Dismissal | |
| Fri., 11/6 | JV Football | O'Brien Tech | Home - Wolcott Tech Football Field [Directions] | 3:00 p.m. | W 36-16 | |
| Fri., 11/6 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | 10:50 AM Dismissal | |
| Sat., 11/7 | School Holidays and Closings | SAT Testing Date | ||||
| Sun., 11/8 | School Holidays and Closings | SAT Testing Date | ||||
| Tue., 11/10 | V Field Hockey | Granby Memorial | Away - Granby Memorial HS [Directions] | 3:30 p.m. | 12:50 PM Dismissal | |
| Wed., 11/11 | School Holidays and Closings | Veterans Day | ||||
| Sat., 11/14 | V Boys Cross Country | New England Championship | Away - Thetford Academy (VT) [Directions] | TBA | ||
| Sat., 11/14 | JV Football | Gilbert/Northwestern/Housy | Away - Gilbert [Directions] | 9:00 a.m. | W 34-14 | |
| Sat., 11/14 | V Girls Cross Country | New England Championship | Away - Thetford Academy (VT) [Directions] | TBA | ||
| Mon., 11/16 | JV Football | Norwich Tech | Away - tba [Directions] | Cancelled | Cancelled | |
| Sat., 11/21 | JV Football | ATI | Home - Wolcott Tech Football Field [Directions] | 11:00 a.m. | L 28-47 | |
| Wed., 11/25 | School Holidays and Closings | Thanksgiving Recess | ||||
| Thu., 11/26 | JV Football | Housatonic Regional | Away - HS Field [Directions] | 10:00 a.m. | W 38-28 | |
| Thu., 11/26 | School Holidays and Closings | Thanksgiving Day | ||||
| Fri., 11/27 | School Holidays and Closings | Thanksgiving Recess | ||||
| Sat., 12/5 | V Girls Basketball | Woodland (Scrim.) | Away - Woodland HS Gym [Directions] | 1:30 p.m. | ||
| Sat., 12/5 | School Holidays and Closings | SAT Testing Date | ||||
| Sun., 12/6 | School Holidays and Closings | SAT Testing Date | ||||
| Tue., 12/8 | V Girls Basketball | Immaculate (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/9 | V Boys Ice Hockey | Forman School (Scrim.) | Home - Rumsey Hall Rink [Directions] | 7:15 p.m. | L 2-8 | |
| Sat., 12/12 | V Boys Basketball | Plainville Jamboree | Away | 3:30 p.m. | ||
| Sat., 12/12 | V Boys Ice Hockey | Hall (Scrim.) | Away - Veteran's Memorial Rink [Directions] | 1:00 p.m. | L 1-6 | |
| Mon., 12/14 | V Boys Basketball | New Fairfield (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/14 | V Boys Ice Hockey | Wethersfield (Scrim.) | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 2-5 | |
| Tue., 12/15 | V Boys Basketball | Brookfield (Scrim.) | Away - BHS Big Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/15 | V Competitive Cheerleading | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Tue., 12/15 | V Girls Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 40-48 | |
| Tue., 12/15 | JV Girls Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/18 | V Boys Swimming and Diving | Berkshire League Relays | Home [Directions] | 4:00 p.m. | ||
| Fri., 12/18 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | W 23-21 | |
| Fri., 12/18 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/19 | V Boys Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 480 Sherman Parkway, New Haven, CT 06511 | |
| Sat., 12/19 | V Girls Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 480 Sherman Parkway, New Haven, CT 06511 | |
| Mon., 12/21 | V Boys Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 57-71 | |
| Mon., 12/21 | JV Boys Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/21 | V Boys Ice Hockey | Mt. Everett (MA) | Home - Gunnery Rink [Directions] | 6:00 p.m. | L 2-5 | |
| Mon., 12/21 | V Competitive Cheerleading | Northwestern | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Mon., 12/21 | V Girls Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 7:00 p.m. | W 42-40 | |
| Mon., 12/21 | JV Girls Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/22 | V Boys Swimming and Diving | Lewis Mills | Home - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Wed., 12/23 | V Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 73-54 | ALUMNI NIGHT |
| Wed., 12/23 | JV Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/23 | FR Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 12/23 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 6:40 p.m. | L 0-9 | |
| Wed., 12/23 | V Competitive Cheerleading | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Wed., 12/23 | V Girls Basketball | Gilbert | Away - Gilbert Gym [Directions] | 5:30 p.m. | L 52-58 | |
| Wed., 12/23 | School Holidays and Closings | Early Dismissal | ||||
| Thu., 12/24 | School Holidays and Closings | Christmas Eve | ||||
| Fri., 12/25 | School Holidays and Closings | Christmas Day | ||||
| Mon., 12/28 | V Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 51-45 | Shepaug Holiday Tournament Opening Round |
| Mon., 12/28 | JV Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 2:30 p.m. | ||
| Mon., 12/28 | FR Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 1:00 p.m. | ||
| Mon., 12/28 | V Competitive Cheerleading | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game - Shepaug Holiday Tournament Opening Round | |
| Tue., 12/29 | V Girls Basketball | Bullard Havens Tech | Away - Fairchild Wheeler Interdistrict Magnet School [Directions] | 1:00 p.m. | W 46-37 | Bridgeport Christmas Tourney at Fairchild Wheeler, 840 Old Town Road Bridgeport, CT. 06606 |
| Wed., 12/30 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavillion [Directions] | 5:00 p.m. | L 1-2 | Bus departs from Washington Primary School |
| Wed., 12/30 | V Girls Basketball | Bridgeport Central | Away - Fairchild Wheeler Interdistrict Magnet School [Directions] | 1:00 p.m. | W 56-23 | Bridgeport Christmas Tourney at Fairchild Wheeler, 840 Old Town Road Bridgeport, CT. 06606 |
| Thu., 12/31 | V Boys Basketball | O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | 1:00 p.m. | W 57-55 | Consolation Game 11:00 am, Championship Game 1:00 pm |
| Thu., 12/31 | V Competitive Cheerleading | Shepaug Holiday Tournament Championship vs O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | 1:00 p.m. | Boys Basketball Game | |
| Thu., 12/31 | School Holidays and Closings | New Years Eve | ||||
| Fri., 1/1 | School Holidays and Closings | New Years Day | ||||
| Sat., 1/2 | V Boys Indoor Track | Wintergreen Invitational | Away - Moore Field House, SCSU | 9:00 a.m. | 125 Wintergreen Ave, New Haven, 06515 | |
| Sat., 1/2 | V Girls Indoor Track | Wintergreen Invitational | Away - Moore Field House, SCSU | 9:00 a.m. | 125 Wintergreen Ave, New Haven, 06515 | |
| Mon., 1/4 | V Boys Ice Hockey | JBWA | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 1-2 | |
| Mon., 1/4 | JV Wrestling | Joel Barlow | Home [Directions] | 3:45 p.m.p.m. | ||
| Tue., 1/5 | V Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 6:00 p.m. | W 59-53 | |
| Tue., 1/5 | JV Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 1/5 | FR Boys Basketball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 3:15 p.m. | 1:50 PM Dismissal | |
| Tue., 1/5 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/5 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | L 49-58 | |
| Tue., 1/5 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Thu., 1/7 | V Boys Swimming and Diving | Housatonic Regional | Home - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Fri., 1/8 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | L 55-70 | |
| Fri., 1/8 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/8 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/8 | V Boys Ice Hockey | Pawling (NY) | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 0-5 | |
| Fri., 1/8 | V Boys Indoor Track | Alpha Owl Invitational | Away - Moore Field House, SCSU | 6:00 p.m. | 125 Wintergreen Ave, New Haven, 06515 | |
| Fri., 1/8 | V Competitive Cheerleading | Thomaston | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Fri., 1/8 | V Girls Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 15-46 | |
| Fri., 1/8 | JV Girls Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/8 | V Girls Indoor Track | Alpha Owl Invitational | Away - Moore Field House, SCSU | 6:00 p.m. | 125 Wintergreen Ave, New Haven, 06515 | |
| Wed., 1/13 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | 5:00 p.m. | L 0-3 | |
| Wed., 1/13 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 5:00 p.m. | ||
| Thu., 1/14 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS [Directions] | 7:00 p.m. | ||
| Thu., 1/14 | V Boys Swimming and Diving | Wamogo | Home - Shepaug Valley HS Pool [Directions] | 7:00 p.m. | ||
| Fri., 1/15 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS [Directions] | 7:00 p.m. | L 59-66 | |
| Fri., 1/15 | V Boys Ice Hockey | Housatonic Coop | Away - Hotchkiss [Directions] | 8:30 p.m. | L 0-5 | |
| Fri., 1/15 | V Boys Indoor Track | Yale Interscholastic Track Classic | Away - Coxe Cage, Yale University | TBA | 257 Derby Avenue, New Haven, CT 06515 | |
| Fri., 1/15 | JV Wrestling | Pomperaug Coop | Away [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 5:30 p.m. | L 29-36 | |
| Fri., 1/15 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/15 | V Girls Indoor Track | Yale Interscholastic Track Classic | Away - Coxe Cage, Yale University | TBA | 257 Derby Avenue, New Haven, CT 06515 | |
| Sat., 1/16 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Mon., 1/18 | School Holidays and Closings | Martin Luther King Day | ||||
| Tue., 1/19 | V Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 7:00 p.m. | L 60-77 | |
| Tue., 1/19 | JV Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | ||
| Tue., 1/19 | V Boys Swimming and Diving | Watertown | Home - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/19 | V Competitive Cheerleading | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Tue., 1/19 | V Girls Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 42-26 | |
| Tue., 1/19 | JV Girls Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/19 | School Holidays and Closings | No School, Professional Development | ||||
| Wed., 1/20 | V Boys Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 77-56 | |
| Wed., 1/20 | JV Boys Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/20 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 2-10 | |
| Wed., 1/20 | V Competitive Cheerleading | Terryville | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Wed., 1/20 | V Girls Basketball | Terryville | Away - New Terryville HS [Directions] | 7:00 p.m. | W 53-48 | |
| Wed., 1/20 | JV Girls Basketball | Terryville | Away - New Terryville HS [Directions] | 5:30 p.m. | ||
| Fri., 1/22 | V Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 88-70 | |
| Fri., 1/22 | JV Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/22 | FR Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/22 | V Boys Ice Hockey | Eastern CT Eagles | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 2-3 | |
| Fri., 1/22 | V Boys Swimming and Diving | Gilbert | Home - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Fri., 1/22 | JV Wrestling | Pomperaug Coop | Away [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | V Competitive Cheerleading | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 1/22 | V Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 41-50 | |
| Fri., 1/22 | JV Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/23 | School Holidays and Closings | SAT Testing Date | ||||
| Sun., 1/24 | School Holidays and Closings | SAT Testing Date | ||||
| Tue., 1/26 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | L 41-57 | |
| Tue., 1/26 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/26 | FR Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Tue., 1/26 | V Boys Ice Hockey | Pawling (NY) | Away - Trinity Pawling Rink | 7:30 p.m. | L 3-4 (OT) | |
| Tue., 1/26 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/26 | V Competitive Cheerleading | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Tue., 1/26 | V Girls Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 24-41 | |
| Tue., 1/26 | JV Girls Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/27 | JV Wrestling | Pomperaug Coop | Away [Directions] | 4:00 p.m. | ||
| Fri., 1/29 | V Boys Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 7:00 p.m. | L 56-78 | |
| Fri., 1/29 | JV Boys Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/29 | V Boys Ice Hockey | Masuk | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 0-2 | |
| Fri., 1/29 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Fri., 1/29 | V Competitive Cheerleading | Northwestern | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Fri., 1/29 | V Girls Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 48-43 | |
| Fri., 1/29 | JV Girls Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/1 | V Boys Ice Hockey | Hall | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 0-5 | |
| Mon., 2/1 | JV Wrestling | Joel Barlow | Home [Directions] | 3:45 p.m. | ||
| Tue., 2/2 | V Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 7:00 p.m. | L 56-64 | |
| Tue., 2/2 | JV Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/2 | FR Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Tue., 2/2 | V Competitive Cheerleading | Nonnewaug | Away - Nonnewaug HS [Directions] | 2:30 p.m. | 1:50 PM Dismissal for Unified Sports Basketball | |
| Tue., 2/2 | V Competitive Cheerleading | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Tue., 2/2 | V Girls Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 43-49 | |
| Tue., 2/2 | JV Girls Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | Cancelled | Cancelled | |
| Tue., 2/2 | Miscellaneous Events | Unified at Nonnewaug | Away | 2:30 p.m. | ||
| Tue., 2/2 | Unified Sports Basketball | Nonnewaug | Away [Directions] | 2:30 p.m. | 1:50 PM Dismissal | |
| Wed., 2/3 | V Boys Ice Hockey | Danbury | Away - Danbury Ice Arena [Directions] | 8:50 p.m. | L 0-2 | |
| Fri., 2/5 | Miscellaneous Events | MS Social | Home - Shepaug Gym and Pool [Directions] | 2:30 p.m. | ||
| Sat., 2/6 | V Competitive Cheerleading | Wamogo | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Girls Basketball Game | |
| Sat., 2/6 | V Girls Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | L 28-35 | |
| Sat., 2/6 | JV Girls Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 2/6 | School Holidays and Closings | ACT Testing Date | ||||
| Tue., 2/9 | V Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 60-63 | |
| Tue., 2/9 | JV Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/9 | FR Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 2/9 | V Boys Swimming and Diving | Lewis Mills | Home - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/9 | JV Wrestling | Pomperaug Coop | Away [Directions] | Cancelled | Cancelled | |
| Tue., 2/9 | V Competitive Cheerleading | Thomaston | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Tue., 2/9 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | L 29-63 | |
| Tue., 2/9 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/10 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena [Directions] | 4:00 p.m. | L 3-9 | |
| Fri., 2/12 | V Boys Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 49-61 | |
| Fri., 2/12 | JV Boys Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 2/12 | V Boys Ice Hockey | Kennedy Catholic-Somers (NY) | Home - Gunnery Rink [Directions] | Cancelled | Cancelled | |
| Fri., 2/12 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Competitive Cheerleading | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 5:00 p.m. | Girls Basketball Game | |
| Fri., 2/12 | V Competitive Cheerleading | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 2/12 | V Girls Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | L 24-44 | |
| Fri., 2/12 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 2/13 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 2:30 p.m. | L 43-50 | |
| Sat., 2/13 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 1:00 p.m. | ||
| Sat., 2/13 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 11:30 a.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | 7:30 p.m. | L 1-4 | |
| Mon., 2/15 | JV Wrestling | (9th Annual President's Day JV Tournament) | Away | 8:00 a.m. | @ Pomperaug | |
| Mon., 2/15 | School Holidays and Closings | Washingtons Birthday | ||||
| Tue., 2/16 | School Holidays and Closings | No School, Professional Development | ||||
| Wed., 2/17 | V Boys Basketball | Terryville | Away - New Terryville HS [Directions] | 7:00 p.m. | W 55-54 | |
| Wed., 2/17 | JV Boys Basketball | Terryville | Away - New Terryville HS [Directions] | 5:30 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | 8:20 p.m. | L 0-2 | |
| Wed., 2/17 | V Boys Swimming and Diving | Northwestern | Home - Shepaug Valley HS Pool [Directions] | 5:00 p.m. | ||
| Wed., 2/17 | V Competitive Cheerleading | Terryville | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Wed., 2/17 | V Girls Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 60-43 | |
| Wed., 2/17 | JV Girls Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/18 | FR Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/18 | V Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 7:00 p.m. | W 40-39 | |
| Thu., 2/18 | JV Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Fri., 2/19 | V Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 59-73 | |
| Fri., 2/19 | JV Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/19 | V Boys Ice Hockey | Forman School (Scrim.) | Home - Rumsey Hall Rink [Directions] | 6:15 p.m. | ||
| Fri., 2/19 | V Competitive Cheerleading | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Sat., 2/20 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/20 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/20 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 2:30 p.m. | Admission Cost: $6 Adults, $3 Students, no passes accepted | |
| Sat., 2/20 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/22 | V Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 7:00 p.m. | L 74-81 | |
| Mon., 2/22 | JV Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/22 | FR Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Tue., 2/23 | V Boys Swimming and Diving | Avon | Away - CCSU [Directions] | Cancelled | Cancelled | 1:50 PM Dismissal |
| Thu., 2/25 | V Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 46-64 | |
| Thu., 2/25 | JV Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/25 | FR Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 2/25 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School | 6:30 p.m. | L 2-3 | Bus Leaves from Washington Primary School |
| Thu., 2/25 | V Competitive Cheerleading | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 2/26 | V Boys Ice Hockey | Sheehan | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 0-2 | |
| Sat., 2/27 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:00 p.m. | BL Tourney Admission $6.00 | |
| Sat., 2/27 | V Boys Swimming and Diving | SPLASH Classic | Away - Plainville HS | 2:00 p.m. | ||
| Sun., 2/28 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 2/28 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Mon., 2/29 | V Boys Ice Hockey | Housatonic Coop | Home - Gunnery Rink [Directions] | 8:00 p.m. | L 0-6 | |
| Mon., 2/29 | V Girls Basketball | Windsor Locks | Away - Windsor Locks HS, 58 South Elm St, Windsor Locks [Directions] | 7:00 p.m. | Admission Cost $8 Adults, $5 Students | |
| Sat., 3/5 | V Boys Swimming and Diving | Berkshire League Championships | Away - Hotchkiss School | 1:00 p.m. | ||
| Sat., 3/5 | School Holidays and Closings | SAT Testing Date | ||||
| Sun., 3/6 | School Holidays and Closings | SAT Testing Date | ||||
| Wed., 3/9 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 3:30 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Wed., 3/23 | School Holidays and Closings | Early Release, Professional Development | ||||
| Thu., 3/24 | School Holidays and Closings | Early Release, Professional Development | ||||
| Fri., 3/25 | School Holidays and Closings | Good Friday | ||||
| Sat., 3/26 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS [Directions] | 10:30 a.m. | ||
| Sun., 3/27 | School Holidays and Closings | Easter Sunday | ||||
| Tue., 3/29 | V Baseball | Torrington (Scrim.) | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Tue., 3/29 | V Softball | Bethel (Scrim.) | Home - Dick Ayer Field [Directions] | 3:45 p.m. | ||
| Wed., 3/30 | V Softball | New Milford (Scrim.) | Away - New Milford HS [Directions] | 3:45 p.m. | ||
| Thu., 3/31 | V Baseball | New Milford (Scrim.) | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 3/31 | V Softball | Canterbury (Scrim.) | Away | 4:30 p.m. | ||
| Wed., 4/6 | V Baseball | Nonnewaug | Away - Nonnewaug HS Field [Directions] | 3:45 p.m. | W 4-2 | |
| Wed., 4/6 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | 3:45 p.m. | ||
| Wed., 4/6 | V Softball | Nonnewaug | Home - Dick Ayer Field [Directions] | 3:45 p.m. | L 11-0 | |
| Wed., 4/6 | V Girls Tennis | Litchfield | Home - Shepaug Valley HS Courts [Directions] | 4:30 p.m. | L 1-5 | |
| Fri., 4/8 | V Baseball | Thomaston | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 13-6 | |
| Fri., 4/8 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | 3:45 p.m. | L 0-10 | |
| Fri., 4/8 | V Girls Tennis | Nonnewaug | Home - Shepaug HS [Directions] | 3:45 p.m. | W 5-2 | |
| Sat., 4/9 | V Boys Tennis | Litchfield | Away - Litchfield HS [Directions] | 10:00 a.m. | L 1-4 | |
| Sat., 4/9 | School Holidays and Closings | ACT Testing Date | ||||
| Mon., 4/11 | V Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 4/11 | JV Baseball | Wamogo | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Wamogo | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Mon., 4/11 | V Softball | Wamogo/Litchfield | Home - Dick Ayer Field [Directions] | 3:45 p.m. | W 3-2 | |
| Mon., 4/11 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/12 | V Baseball | Housatonic Regional | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 4/12 | V Boys Outdoor Track | Nonnewaug | Home - Shepaug Valley HS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Boys Tennis | Nonnewaug | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 4/12 | V Girls Outdoor Track | Nonnewaug | Home - Shepaug Valley HS Track [Directions] | 4:00 p.m. | 59-87 (Nonnewaug) | |
| Wed., 4/13 | V Baseball | Litchfield | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 9-3 | |
| Wed., 4/13 | V Softball | Litchfield | Away - Plumb Hill Complex [Directions] | 3:45 p.m. | W 19-11 | |
| Wed., 4/13 | V Girls Tennis | Northwestern | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/14 | V Girls Tennis | Gilbert | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/14 | School Holidays and Closings | Junior Field Trip | Returns 3:30 PM | |||
| Fri., 4/15 | V Baseball | Platt | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 7-4 | |
| Fri., 4/15 | JV Baseball | Thomaston | Home - Shepaug Valley HS JV Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/15 | V Boys Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | 1:50 PM Dismissal |
| Mon., 4/18 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | 3:45 p.m. | L 7-4 | Bus Departs from Ted Alex Field |
| Mon., 4/18 | JV Baseball | Lewis Mills | Away - Lewis Mills JV Baseball Field [Directions] | 3:45 p.m. | Bus Departs from Ted Alex Field | |
| Mon., 4/18 | V Boys Tennis | Lewis Mills | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 4/18 | V Softball | Lewis Mills | Home - Dick Ayer Field [Directions] | 3:45 p.m. | L 15-0 | |
| Mon., 4/18 | V Girls Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | 1:50 PM Dismissal |
| Tue., 4/19 | V Softball | Wamogo/Litchfield | Away - Wamogo Varsity Softball Field [Directions] | 3:45 p.m. | L 6-8 | Bus Departs from Washington Primary School |
| Wed., 4/20 | V Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 6-3 | Bus Departs from Ted Alex Field |
| Wed., 4/20 | JV Baseball | Northwestern | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Boys Tennis | Gilbert | Away - Gilbert [Directions] | 3:45 p.m. | W 3-2 | |
| Wed., 4/20 | V Softball | Northwestern | Home - Dick Ayer Field [Directions] | 3:45 p.m. | L 2-7 | |
| Thu., 4/21 | JV Baseball | Housatonic Regional | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 4/21 | V Softball | Housatonic Regional | Home - Dick Ayer Field [Directions] | 3:45 p.m. | W 17-0 | |
| Mon., 4/25 | V Baseball | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 1-0 | 1:50 PM Dismissal |
| Mon., 4/25 | JV Baseball | Gilbert | Away - Gilbert [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Mon., 4/25 | V Boys Tennis | Housatonic Regional | Away - HS Courts [Directions] | 3:45 p.m. | L 1-4 | 1:50 PM Dismissal |
| Mon., 4/25 | V Softball | Gilbert | Home - Dick Ayer Field [Directions] | 3:45 p.m. | W 8-7 | |
| Mon., 4/25 | V Girls Tennis | Housatonic Regional | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/26 | V Boys Golf | Terryville | Home - Lake Waramaug Country Club [Directions] | 3:15 p.m. | Terryville 212, Shepaug 231 | |
| Tue., 4/26 | V Boys Outdoor Track | Thomaston, Northwestern | Home - Shepaug Valley HS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Outdoor Track | Thomaston, Northwestern | Home - Shepaug Valley HS Track [Directions] | 4:00 p.m. | 104-38 (Thomaston) 92-58 (Northwestern) | |
| Tue., 4/26 | School Holidays and Closings | Finance Field Trip | Returns at 3:00 PM | |||
| Tue., 4/26 | Unified Sports Volleyball | Nonnewaug | Away [Directions] | 2:30 p.m. | ||
| Wed., 4/27 | V Baseball | Terryville | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 10-3 | |
| Wed., 4/27 | V Boys Tennis | Thomaston | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | W 4-1 | |
| Wed., 4/27 | V Softball | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | W 22-7 | 1:50 PM Dismissal |
| Wed., 4/27 | V Girls Tennis | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/28 | V Baseball | Housatonic Regional | Away - HS Field [Directions] | 3:45 p.m. | W 3-0 | 1:50 PM Dismissal |
| Thu., 4/28 | JV Baseball | Housatonic Regional | Away - HS JV Field [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Thu., 4/28 | V Boys Golf | Litchfield, Lewis Mills | Away [Directions] | 3:00 p.m. | Lewis Mills 164, Litchfield 166, Shepaug 238 | 1:50 PM Dismissal |
| Thu., 4/28 | V Boys Outdoor Track | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | 2:05 PM Dismissal | |
| Thu., 4/28 | V Boys Tennis | Gilbert | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 4/28 | V Girls Outdoor Track | Terryville | Away - New Terryville HS [Directions] | 4:00 p.m. | 90-46 | 2:05 PM Dismissal |
| Thu., 4/28 | V Softball | Housatonic Regional | Away - Housatonic Field [Directions] | 3:45 p.m. | W 15-3 | 1:50 PM Dismissal |
| Thu., 4/28 | V Girls Tennis | Gilbert | Away - Gilbert [Directions] | 3:45 p.m. | W 7-0 | 1:50 PM Dismissal |
| Sat., 4/30 | V Boys Outdoor Track | 8th Fermi Coed Relays | Away - Enrico Fermi HS, Enfield, CT | 10:00 a.m. | ||
| Sat., 4/30 | V Girls Outdoor Track | 8th Fermi Coed Relays | Away - Enrico Fermi HS, Enfield, CT | 10:00 a.m. | ||
| Mon., 5/2 | V Boys Golf | Northwestern, Lewis Mills | Away [Directions] | 3:45 p.m. | Lewis Mills 166, Northwestern 172, Shepaug 236 | 1:30 PM Dismissal |
| Tue., 5/3 | V Baseball | Nonnewaug | Home - Ted Alex Field [Directions] | 4:15 p.m. | W 6-1 | |
| Tue., 5/3 | V Boys Golf | Wamogo, Housatonic Regional | Away [Directions] | 3:45 p.m. | Housatonic 209, Wamogo 211, Shepaug 228 | 1:40 PM Dismissal |
| Tue., 5/3 | V Boys Outdoor Track | Litchfield, Gilbert | Away - Plumb Hill Complex [Directions] | 4:15 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Litchfield, Gilbert | Away - Plumb Hill Complex [Directions] | 4:15 p.m. | S-L 108-42 S-G 115-22 | |
| Wed., 5/4 | V Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | 3:45 p.m. | L 11-1 | |
| Wed., 5/4 | JV Baseball | Terryville | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Boys Tennis | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | W 4-1 | |
| Thu., 5/5 | V Softball | Nonnewaug | Away - Nonnewaug Varsity Softball Field [Directions] | 3:45 p.m. | L 1-10 | |
| Thu., 5/5 | V Girls Tennis | Thomaston | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 5/6 | V Boys Outdoor Track | Irv Black Invitational | Away - Willowbrook Park, New Britain [Directions] | 3:30 p.m. | 1:50 PM Dismissal | |
| Fri., 5/6 | V Girls Outdoor Track | Irv Black Invitational | Away - Willowbrook Park, New Britain [Directions] | 3:30 p.m. | 1:50 PM Dismissal | |
| Sat., 5/7 | V Boys Outdoor Track | Irv Black Invitational | Away - Willowbrook Park, New Britain [Directions] | 10:00 a.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Irv Black Invitational | Away - Willowbrook Park, New Britain [Directions] | 10:00 a.m. | ||
| Sat., 5/7 | School Holidays and Closings | SAT Testing Date | ||||
| Sun., 5/8 | School Holidays and Closings | SAT Testing Date | ||||
| Mon., 5/9 | V Baseball | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | W 12-0 | |
| Mon., 5/9 | JV Baseball | Terryville | Away - Lower Fisher Elementary [Directions] | 3:45 p.m. | 2:05 PM Dismissal | |
| Mon., 5/9 | V Boys Tennis | Northwestern | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Mon., 5/9 | V Softball | Litchfield | Home - Dick Ayer Field [Directions] | 3:45 p.m. | W 8-1 | |
| Mon., 5/9 | V Girls Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | 1:50 PM Dismissal |
| Tue., 5/10 | V Baseball | Wamogo | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 10-2 | |
| Tue., 5/10 | JV Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Boys Golf | Gilbert, Wamogo | Home - Lake Waramaug Country Club [Directions] | 3:15 p.m. | Gilbert 224, Shepaug 227, Wamogo 233 | |
| Tue., 5/10 | V Boys Outdoor Track | Wamogo | Home - Shepaug Valley HS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Nonnewaug | Away - Edgewood Tennis and Bath [Directions] | 3:45 p.m. | L 0-5 | l |
| Tue., 5/10 | V Girls Outdoor Track | Wamogo | Home - Shepaug Valley HS Track [Directions] | 4:00 p.m. | 116-33 (Shepaug-wamogo) | |
| Tue., 5/10 | V Girls Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | 1:50 PM Dismissal |
| Wed., 5/11 | V Softball | Thomaston | Home - Dick Ayer Field [Directions] | 3:45 p.m. | L 18-9 | |
| Thu., 5/12 | V Boys Golf | Terryville, Nonnewaug | Away [Directions] | 3:00 p.m. | Nonnewaug 169, Terryville 196, Shepaug 210 | 1:40 PM Dismissal |
| Thu., 5/12 | V Boys Tennis | Abbott Tech | Home - Shepaug Valley HS Courts [Directions] | 3:30 p.m. | L 2-5 | |
| Thu., 5/12 | V Girls Tennis | Nonnewaug | Away - Edgewood Tennis and Bath [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 5/13 | V Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | 3:45 p.m. | L 5-9 | 1:50 PM Dismissal |
| Sat., 5/14 | V Boys Outdoor Track | Torrington Varsity Alumni Club Track and Field Challenge | Away - Torrington HS | 10:30 a.m. | ||
| Sat., 5/14 | V Girls Outdoor Track | Torrington Varsity Alumni Club Track and Field Challenge | Away - Torrington HS | 10:30 a.m. | ||
| Sat., 5/14 | V Softball | Wolcott | Home - Joe Martin Field [Directions] | 10:00 a.m. | L 11-3 | |
| Sat., 5/14 | V Girls Tennis | Wamogo | Home - Shepaug Valley HS Courts [Directions] | 12:00 p.m. | W 7-0 | |
| Sun., 5/15 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 12:30 p.m. | L 2-3 | |
| Mon., 5/16 | V Baseball | Northwestern | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 8-3 | |
| Mon., 5/16 | JV Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | 1:50 PM Dismissal | |
| Mon., 5/16 | V Boys Golf | Litchfield, Northwestern | Home - Lake Waramaug Country Club [Directions] | 3:15 p.m. | Litchfield 175, Northwestern 215, Shepaug 232 | |
| Mon., 5/16 | V Boys Outdoor Track | Terryville, Housatonic Regional, Lewis Mills | Away - New Terryville HS [Directions] | 4:00 p.m. | 2:05 PM Dismissal | |
| Mon., 5/16 | V Boys Tennis | Housatonic Regional | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 5/16 | V Girls Outdoor Track | Terryville, Housatonic Regional, Lewis Mills | Away - New Terryville HS [Directions] | 4:00 p.m. | 2:05 PM Dismissal | |
| Mon., 5/16 | V Softball | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 5-20 | 1:50 PM Dismissal |
| Mon., 5/16 | V Girls Tennis | Housatonic Regional | Away - HS Courts [Directions] | 3:45 p.m. | W 6-1 | 1:50 PM Dismissal |
| Tue., 5/17 | V Baseball | Lewis Mills | Home - Ted Alex Field [Directions] | 3:45 p.m. | W 6-2 | |
| Tue., 5/17 | JV Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/17 | V Boys Golf | New Milford | Home - Lake Waramaug Country Club [Directions] | 3:15 p.m. | New Milford 150, Shepaug 205 | |
| Tue., 5/17 | V Boys Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | 1:50 PM Dismissal |
| Wed., 5/18 | V Baseball | Brookfield | Away - BHS Baseball Field [Directions] | 4:00 p.m. | L 6-4 | 1:50 PM Dismissal |
| Wed., 5/18 | FR Baseball | Brookfield | Away - Huckleberry Hill Elementary School Baseball Field [Directions] | 4:00 p.m. | 1:50 PM Dismissal | |
| Wed., 5/18 | V Boys Golf | Nonnewaug | Away [Directions] | 3:45 p.m. | Nonnewaug 170, Shepaug 206 | 1:40 PM Dismissal |
| Wed., 5/18 | V Boys Tennis | Litchfield | Home - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 5/18 | V Girls Tennis | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/19 | V Baseball | Gilbert | Home - Ted Alex Field [Directions] | 4:00 p.m. | L 5-1 | |
| Thu., 5/19 | JV Baseball | Gilbert | Home - Shepaug Valley HS JV Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Girls Tennis | Berkshire League All-Star Tourney | Away - Hotchkiss School | 8:30 a.m. | ||
| Thu., 5/19 | Miscellaneous Events | High School Concert | Home [Directions] | 7:00 p.m. | ||
| Fri., 5/20 | V Boys Tennis | Berkshire League All Star Tournament | Away - Hotchkiss School | 8:30 p.m. | ||
| Fri., 5/20 | V Softball | Gilbert | Away - Rowley Field [Directions] | 3:45 p.m. | W 16-5 | 1:50 PM Dismissal |
| Sat., 5/21 | V Boys Outdoor Track | Berkshire League Championships | Away - Litchfield HS Track | 9:00 a.m. | ||
| Sat., 5/21 | V Girls Outdoor Track | Berkshire League Championship | Away | 9:00 a.m. | ||
| Mon., 5/23 | V Baseball | Terryville | Away - New Terryville HS [Directions] | 3:45 p.m. | L 4-2 | 2:05 PM Dismissal |
| Mon., 5/23 | V Boys Golf | Housatonic Regional, Gilbert | Away - Sharon Country Club [Directions] | 3:15 p.m. | Gilbert 205, Shepaug 228, Housatonic 255 | 1:30 PM Dismissal |
| Mon., 5/23 | V Softball | Terryville | Home - Dick Ayer Field [Directions] | 3:45 p.m. | W 14-0 | |
| Tue., 5/24 | V Boys Outdoor Track | BL Festival | Away - Housatonic Valley Regional HS | 4:00 p.m. | ||
| Tue., 5/24 | V Girls Outdoor Track | BL Festival | Away - Housatonic Valley Regional HS | 4:00 p.m. | ||
| Wed., 5/25 | V Boys Outdoor Track | BL Festival | Away - Housatonic Valley Regional HS | 4:00 p.m. | ||
| Wed., 5/25 | V Girls Outdoor Track | BL Festival | Away - Housatonic Valley Regional HS | 4:00 p.m. | ||
| Thu., 5/26 | V Baseball | Torrington (Scrim.) | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 5/26 | V Girls Tennis | Lewis Mills | Home - Shepaug Valley HS Courts [Directions] | 3:15 p.m. | W 5-2 | |
| Fri., 5/27 | School Holidays and Closings | Early Release, Professional Development | ||||
| Mon., 5/30 | School Holidays and Closings | Memorial Day | ||||
| Tue., 5/31 | V Baseball | St. Bernard | Home - Ted Alex Field [Directions] | 3:30 p.m. | 2:05 PM Dismissal | |
| Tue., 5/31 | V Boys Golf | Berkshire League All-Star Tourney | Away - Fairview Farm Golf Course | 7:00 a.m. | 8:00 AM Dismissal | |
| Tue., 5/31 | V Softball | Wheeler | Away - 297 Norwich-Westerly Rd, North Stonington, CT [Directions] | 4:00 p.m. | 12:00 PM Dismissal | |
| Tue., 5/31 | V Girls Tennis | Cromwell | Home - Shepaug Valley HS Courts [Directions] | 3:00 p.m. | 1:30 pm Dismissal | |
| Wed., 6/1 | V Girls Tennis | Northwest Catholic | Home - Shepaug Valley HS Courts [Directions] | 3:00 p.m. | 1:30 PM Dismissal | |
| Thu., 6/2 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park [Directions] | 2:30 p.m. | 12:30 PM Dismissal | |
| Thu., 6/2 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park [Directions] | 2:30 p.m. | 12:30 PM Dismissal | |
| Sat., 6/4 | School Holidays and Closings | SAT Testing Date | ||||
| Sun., 6/5 | School Holidays and Closings | SAT Testing Date | ||||
| Mon., 6/6 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 11:05 PM Dismissal | |
| Wed., 6/8 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 11:05 AM Dismissal | |
| Sat., 6/11 | V Boys Outdoor Track | New England Championship | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Sat., 6/11 | V Girls Outdoor Track | New England Championship | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Sat., 6/11 | School Holidays and Closings | ACT Testing Date | ||||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park | 11:30 a.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Sun., 6/19 | School Holidays and Closings | Fathers Day | ||||