| Northwestern 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 550 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Thomaston | Home - Northwestern Varsity Field [Directions] | 10:00 a.m. | ||
| TBA | JV Baseball | Thomaston | Home - Northwestern Varsity Field [Directions] | 10:30 a.m. | ||
| TBA | JV Baseball | Gilbert | Home - Northwestern Varsity Field [Directions] | 12:15 p.m. | ||
| TBA | JV Baseball | St. Paul Catholic | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Litchfield | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Gilbert | Away - Walker Field [Directions] | TBA | ||
| TBA | JV Baseball | Litchfield | Away - Litchfield HS Baseball Field [Directions] | TBA | ||
| TBA | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| TBA | V Boys Tennis | Granby Memorial | Home - NWR-7 Tennis Courts [Directions] | Cancelled | Cancelled | |
| TBA | V Boys Tennis | Gilbert | Away - Gilbert [Directions] | TBA | W 5-0 | |
| TBA | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | TBA | ||
| TBA | V Girls Soccer | Canton (Scrim.) | Away - Canton H.S. Turf [Directions] | TBA | ||
| TBA | JV Girls Soccer | Litchfield | Home - Northwestern JV field [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Soccer | Terryville | Away - Upper Fisher Field [Directions] | TBA | ||
| TBA | JV Softball | Nonnewaug | Home - Northwestern JV field [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Canton | Home - Northwestern JV field [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Litchfield | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Terryville | Home - Northwestern Varsity Field [Directions] | TBA | ||
| TBA | JV Softball | Terryville | Away - Terryville HS [Directions] | TBA | ||
| Wed., 8/22 | V Football | Simsbury (Scrim.) | Away [Directions] | 9:00 a.m. | Legeyt bus company 7:45 am 1 bus | |
| Fri., 8/31 | V Football | Torrington (Scrim.) | Away - Torrington HS [Directions] | 7:00 p.m. | Students are responsable for their own transportation to and from the game | |
| Fri., 9/7 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS Varsity Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 9/7 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS Varsity Field [Directions] | 5:00 p.m. | W 1-0 | |
| Fri., 9/7 | V Girls Soccer | Housatonic Regional | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-4 | |
| Fri., 9/7 | JV Girls Soccer | Housatonic Regional | Home - Northwestern JV field [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 9/7 | V Girls Volleyball | Gilbert | Home - Northwestern Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/7 | JV Girls Volleyball | Gilbert | Home - Northwestern Gym [Directions] | Cancelled | Cancelled | |
| Sat., 9/8 | V Boys Cross Country | Windham Invite | Away - Windham HS | TBA | Bus 6:30am | |
| Sat., 9/8 | V Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 2:00 p.m. | W 20-7 | Legeyt Bus Compan 10:30am pickup Two busses |
| Sat., 9/8 | V Boys Soccer | Housatonic Regional | Away - Housatonic [Directions] | 10:30 a.m. | W 3-1 | |
| Sat., 9/8 | JV Boys Soccer | Housatonic Regional | Away - Housatonic [Directions] | 10:30 a.m. | W 5-0 | |
| Sat., 9/8 | V Girls Cross Country | Windham Invite | Away - Windham HS | TBA | Bus 6:30am | |
| Mon., 9/10 | JV Football | Old Saybrook | Home - Gilbert [Directions] | Cancelled | Cancelled | |
| Mon., 9/10 | V Girls Volleyball | North Branford | Home - Northwestern Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 9/10 | JV Girls Volleyball | North Branford | Home - Northwestern Gym [Directions] | 4:30 p.m. | W 2-1 | |
| Tue., 9/11 | V Boys Cross Country | Gilbert, Litchfield | Home - Northwestern [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Boys Soccer | Wamogo | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 5-1 | |
| Tue., 9/11 | JV Boys Soccer | Wamogo | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 7-1 | |
| Tue., 9/11 | V Girls Cross Country | Litchfield, Gilbert | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 9/11 | JV Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 5:00 p.m. | L 0-2 | |
| Fri., 9/14 | V Football | Rockville | Away - RHS football field [Directions] | 6:30 p.m. | L 7-48 | Legeyt bus company pickup at 3:15pm - Two busses |
| Fri., 9/14 | V Boys Soccer | Terryville | Away - Terryville HS [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 9/14 | JV Boys Soccer | Terryville | Away - Upper Fisher Field [Directions] | 3:45 p.m. | W 4-1 | |
| Fri., 9/14 | V Girls Soccer | Terryville | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 9/14 | V Girls Volleyball | Nonnewaug | Home - Northwestern Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Fri., 9/14 | JV Girls Volleyball | Nonnewaug | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/15 | V Boys Cross Country | Stratton Brook | Away - Stratton Brook | TBA | bus 7:30 am | |
| Sat., 9/15 | JV Football | Rockville | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | V Girls Cross Country | Stratton Brook | Away - Stratton Brook | TBA | Bus 7:30am | |
| Sat., 9/15 | V Girls Soccer | Wamogo | Home - NWR Varsity Field [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 9/15 | JV Girls Soccer | Terryville | Home - Northwestern JV field [Directions] | 9:00 a.m. | W 7-0 | |
| Tue., 9/18 | V Girls Volleyball | Lewis Mills | Home - NWR [Directions] | 5:15 p.m. | L 2-3 | |
| Tue., 9/18 | JV Girls Volleyball | Lewis Mills | Home - NWR [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 9/19 | V Field Hockey | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 6:15 p.m. | L 1-4 | |
| Wed., 9/19 | JV Field Hockey | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 4:30 p.m. | L 0-2 | |
| Wed., 9/19 | V Girls Volleyball | Northwest Catholic | Home - Northwestern Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/19 | JV Girls Volleyball | Northwest Catholic | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/20 | V Boys Cross Country | Shepaug Valley | Away - Shepaug Valley School [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Boys Soccer | Thomaston | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 9/20 | V Girls Cross Country | Shepaug Valley | Away - Shepaug Valley School [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Field Hockey | Shepaug Valley | Away - Joan Gauthey Field [Directions] | 3:45 p.m. | W 4-0 | |
| Thu., 9/20 | JV Field Hockey | Shepaug Valley | Away - Joan Gauthey Field [Directions] | 5:00 p.m. | T 0-0 | |
| Thu., 9/20 | V Girls Soccer | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 9/21 | V Football | Stafford/East Windsor/Somers | Away - Stafford High, Lighted field behind school [Directions] | 6:30 p.m. | L 12-35 | Legeyt Bus Company - Pickup at 3:15pm - Two busses |
| Fri., 9/21 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | T 2-2 | |
| Fri., 9/21 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 9/21 | V Girls Soccer | Shepaug Valley | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/21 | JV Girls Soccer | Shepaug Valley | Home - Northwestern JV field [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 9/21 | V Girls Volleyball | Housatonic Regional | Away - Housatonic [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 9/21 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/22 | V Boys Cross Country | Winding Trails | Away - Winding Trail | TBA | ||
| Sat., 9/22 | JV Football | Stafford/East Windsor/Somers | Home - Gilbert [Directions] | 10:30 a.m. | ||
| Sat., 9/22 | V Girls Cross Country | Winding Trails | Away - Winding Trail | TBA | ||
| Sat., 9/22 | JV Girls Soccer | Canton | Away - Canton H.S. Turf [Directions] | 10:00 a.m. | L 0-1 | |
| Mon., 9/24 | V Field Hockey | New Milford | Home - Northwestern HS [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 9/24 | JV Field Hockey | New Milford | Home - Northwestern HS [Directions] | 5:30 p.m. | L 0-4 | |
| Tue., 9/25 | V Girls Volleyball | Suffield | Home - Northwestern Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/25 | JV Girls Volleyball | Suffield | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 9/26 | V Boys Cross Country | Nonnewaug, Thomaston | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | V Girls Cross Country | Nonnewaug, Thomaston | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 9/27 | V Girls Volleyball | Terryville | Home - Northwestern Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 9/27 | JV Girls Volleyball | Terryville | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 9/28 | JV Girls Soccer | Gilbert | Home - Northwestern Varsity Field [Directions] | Cancelled | Cancelled | |
| Sat., 9/29 | V Football | Canton | Home - Gilbert [Directions] | 1:00 p.m. | W 45-14 | |
| Mon., 10/1 | JV Football | Canton | Away - Canton H.S. Grass [Directions] | 3:45 p.m. | Legeyt bus company - 1 bus for JV game | |
| Mon., 10/1 | V Boys Soccer | Gilbert | Home - Northwestern Varsity Field [Directions] | 7:30 p.m. | W 4-1 | |
| Mon., 10/1 | JV Boys Soccer | Gilbert | Home - Northwestern Varsity Field [Directions] | 4:30 p.m. | W 6-1 | |
| Mon., 10/1 | V Field Hockey | Wamogo | Home - Wamogo Regional HS [Directions] | 3:45 p.m. | L 1-2 | |
| Mon., 10/1 | JV Field Hockey | Wamogo | Home - Wamogo Regional HS [Directions] | 5:00 p.m. | W 1-0 | |
| Mon., 10/1 | V Girls Soccer | Litchfield | Home - Northwestern Varsity Field [Directions] | 5:45 p.m. | T 0-0 | |
| Mon., 10/1 | JV Girls Soccer | Litchfield | Home - Northwestern Field [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/2 | JV Boys Soccer | Lewis Mills | Away - Lewis Mills Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-1 | |
| Tue., 10/2 | JV Field Hockey | Housatonic Regional | Home - Northwestern Field [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Girls Volleyball | Gilbert | Away - Gilbert Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/2 | JV Girls Volleyball | Gilbert | Away - Gilbert Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/4 | V Boys Cross Country | Litchfield, Shepaug Valley | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Thu., 10/4 | V Girls Cross Country | Litchfield, Shepaug Valley | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Thu., 10/4 | V Field Hockey | Litchfield | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 10/4 | JV Field Hockey | Litchfield | Home - Northwestern Varsity Field [Directions] | 5:00 p.m. | W 1-0 | |
| Thu., 10/4 | V Girls Volleyball | Holy Cross | Home - Northwestern Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Thu., 10/4 | JV Girls Volleyball | Holy Cross | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 10/5 | V Boys Soccer | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-3 | |
| Fri., 10/5 | JV Boys Soccer | Nonnewaug | Home - Northwestern JV field [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 10/5 | V Field Hockey | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 10/5 | JV Field Hockey | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 5:00 p.m. | ||
| Fri., 10/5 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS [Directions] | 3:45 p.m. | W 1-0 | |
| Sat., 10/6 | V Boys Cross Country | Wickham | Away - Wickham | TBA | ||
| Sat., 10/6 | V Football | Windsor Locks/Suffield/East Granby | Home - Gilbert [Directions] | 3:00 p.m. | L 14-27 | |
| Sat., 10/6 | JV Boys Soccer | Thomaston | Home - Northwestern Varsity Field [Directions] | 10:00 a.m. | W 6-0 | |
| Sat., 10/6 | V Girls Cross Country | Wickham | Away - Wickham | TBA | ||
| Sat., 10/6 | JV Girls Soccer | Thomaston | Home - Northwestern HS [Directions] | Cancelled | Cancelled | |
| Sat., 10/6 | JV Girls Soccer | Thomaston | Home - Northwestern HS [Directions] | 10:00 a.m. | T 1-0 | |
| Mon., 10/8 | JV Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks HS [Directions] | 11:00 a.m. | Legeyt bus company - 9:00am pickup - 1 bus | |
| Mon., 10/8 | V Boys Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | 3:45 p.m. | L 5-1 | |
| Tue., 10/9 | V Boys Cross Country | Wamogo, Terryville | Away - White Memorial (HS XC Course) [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Soccer | Housatonic Regional | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-1 | |
| Tue., 10/9 | JV Boys Soccer | Housatonic Regional | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 10/9 | V Girls Cross Country | Wamogo, Terryville | Away - White Memorial (HS XC Course) [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Field Hockey | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/9 | JV Field Hockey | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 5:00 p.m. | ||
| Tue., 10/9 | V Girls Soccer | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | L 0-2 | |
| Tue., 10/9 | JV Girls Soccer | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | W 3-0 | |
| Thu., 10/11 | V Girls Volleyball | Ellington | Home - Northwestern Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/11 | JV Girls Volleyball | Ellington | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/13 | V Girls Soccer | Lewis Mills | Home - Northwestern Field [Directions] | 10:00 a.m. | L 0-5 | |
| Sat., 10/13 | JV Girls Soccer | Lewis Mills | Home - Northwestern JV field [Directions] | 10:00 a.m. | L 0-4 | |
| Mon., 10/15 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 5:30 p.m. | L 0-5 | |
| Mon., 10/15 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 4:15 p.m. | L 0-2 | |
| Tue., 10/16 | V Boys Cross Country | Lewis Mills, Housatonic Regional | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Boys Soccer | Terryville | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 10/16 | JV Boys Soccer | Terryville | Home - Northwestern Varsity Field [Directions] | Cancelled | Cancelled | |
| Tue., 10/16 | V Girls Cross Country | Lewis Mills, Housatonic Regional | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Girls Soccer | Terryville | Away - Terryville HS [Directions] | 3:45 p.m. | W 4-3 ot | |
| Tue., 10/16 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Tue., 10/16 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/17 | V Girls Volleyball | Tolland | Home - Northwestern Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/17 | JV Girls Volleyball | Tolland | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 10/18 | V Girls Soccer | Gilbert | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/19 | V Boys Cross Country | BL Championships | Away - Black Rock | TBA | Boys JV 2:45 Girls 3:30 Boys 4:15 | |
| Fri., 10/19 | V Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS [Directions] | 7:00 p.m. | W 42-24 | Legeyt bus company - 3:45pm pickup - 2 busses |
| Fri., 10/19 | V Boys Soccer | Litchfield | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 10/19 | JV Boys Soccer | Litchfield | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 10/19 | V Girls Cross Country | BL Championships | Away - Black Rock | 4:15 p.m. | Boys JV 2:45 Girls 3:30 Boys 4:15 | |
| Fri., 10/19 | V Field Hockey | Thomaston | Home - Northwestern Regional Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/19 | JV Field Hockey | Thomaston | Home - Northwestern Field [Directions] | 5:00 p.m. | ||
| Fri., 10/19 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | W 2-1 OT | |
| Fri., 10/19 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | W 5-1 | |
| Fri., 10/19 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 10/19 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 4:00 p.m. | W 2-1 | |
| Sat., 10/20 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 9:00 a.m. | L 2-1 | |
| Sat., 10/20 | JV Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 9:00 a.m. | W 6-0 | |
| Mon., 10/22 | V Boys Soccer | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-4 | |
| Mon., 10/22 | JV Boys Soccer | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 2-0 | |
| Mon., 10/22 | V Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | 3:45 p.m. | L 0-1 | |
| Mon., 10/22 | JV Field Hockey | Thomaston | Away - Thomaston HS [Directions] | 5:00 p.m. | T 3-3 | |
| Mon., 10/22 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 4-0 | |
| Tue., 10/23 | V Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 10/23 | JV Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/23 | V Girls Soccer | Lewis Mills | Away - Lewis Mills Track [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 10/23 | JV Girls Soccer | Lewis Mills | Away - Lewis Mills JV Soccer Field [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 10/23 | V Girls Volleyball | Housatonic Regional | Home - Northwestern Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/23 | JV Girls Volleyball | Housatonic Regional | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/25 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | L 0-1 | |
| Thu., 10/25 | V Girls Volleyball | Canton | Away - Canton H.S. [Directions] | 5:15 p.m. | W 3-1 | |
| Thu., 10/25 | JV Girls Volleyball | Canton | Away - Canton H.S. [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 10/26 | V Boys Cross Country | CIAC STATES | Away | TBA | ||
| Fri., 10/26 | V Football | Ellington | Home - Torrington HS Turf Football Field [Directions] | 7:00 p.m. | W 23-0 | Homecoming |
| Fri., 10/26 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS Varsity Field [Directions] | 3:45 p.m. | T 2-2 | |
| Fri., 10/26 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | Cancelled | Cancelled | |
| Fri., 10/26 | V Girls Cross Country | CIAC STATES | Away | TBA | ||
| Fri., 10/26 | V Field Hockey | Shepaug Valley | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 1-0 OT | |
| Fri., 10/26 | JV Field Hockey | Shepaug Valley | Home - Northwestern Varsity Field [Directions] | 5:00 p.m. | ||
| Fri., 10/26 | V Girls Soccer | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 10/26 | V Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/26 | JV Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | L 1-2 | |
| Mon., 10/29 | JV Football | Ellington | Away - Ellington HS [Directions] | 3:45 p.m. | Legeyt - Pickup at Regional for 2:15pm and then go to Gilbert to pick up players and coaches. | |
| Mon., 10/29 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 7:15 p.m. | W 6-0 | |
| Mon., 10/29 | JV Girls Soccer | Gilbert | Away - Walker Field [Directions] | Cancelled | Cancelled | |
| Mon., 10/29 | V Girls Volleyball | Terryville | Away - Terryville HS [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 10/29 | JV Girls Volleyball | Terryville | Away - Terryville HS [Directions] | 4:00 p.m. | W 1-2 | |
| Tue., 10/30 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 7:15 p.m. | W 3-1 | |
| Tue., 10/30 | JV Boys Soccer | Gilbert | Away - Rowley Field [Directions] | 3:45 p.m. | W 6-2 | |
| Wed., 10/31 | V Field Hockey | Canton | Home - Northwestern Varsity Field [Directions] | 3:15 p.m. | W 2-1 | |
| Wed., 10/31 | JV Field Hockey | Canton | Home - Northwestern Varsity Field [Directions] | 4:30 p.m. | ||
| Fri., 11/2 | V Boys Cross Country | State Opens | Away | Cancelled | Cancelled | |
| Fri., 11/2 | V Football | Granby/Canton | Away - Granby Memorial HS [Directions] | 6:00 p.m. | L 0-39 | Legeyt bus company - 4:30pm pickup - 2 busses |
| Fri., 11/2 | V Girls Cross Country | State Opens | Away | Cancelled | Cancelled | |
| Fri., 11/2 | V Girls Volleyball | Tournament Game - Opponent Not Known | Away - Lewis Mills | 5:00 p.m. | ||
| Sat., 11/3 | JV Football | Granby/Canton | Away - Granby Memorial HS [Directions] | 10:00 a.m. | ||
| Mon., 11/5 | V Girls Soccer | Woodland | Home - Walker Field Winsted Rowley Street [Directions] | 2:00 p.m. | W 2-1 | |
| Mon., 11/5 | V Girls Volleyball | Lewis Mills | Home - Northwestern Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 11/6 | V Boys Soccer | Bullard Havens Tech | Away - Luis Marin Elementary School located at 479 Helen Street in Bridgeport [Directions] | 2:00 p.m. | W 1-0 | Luis Marin Elementary School located at 479 Helen Street in Bridgeport |
| Wed., 11/7 | V Field Hockey | Stonington | Away - Palmer Field (Turf) [Directions] | 2:00 p.m. | L 0-6 | |
| Wed., 11/7 | V Girls Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | 5:00 p.m. | L 0-6 | |
| Thu., 11/8 | V Boys Soccer | Plainville | Away - Plainville HS - Tinty Field and Track [Directions] | 6:00 p.m. | L 1-3 | |
| Sat., 11/10 | V Football | SMSA Coop | Home - Gilbert [Directions] | 1:00 p.m. | L 0-20 | |
| Mon., 11/12 | JV Football | SMSA Coop | Home - Gilbert [Directions] | 3:00 p.m. | ||
| Fri., 11/23 | V Football | WCA | Home - Gilbert [Directions] | 1:00 p.m. | L 21-62 | |
| Fri., 11/30 | V Girls Ice Hockey | SCC North Jamboree | Away - ISCC | TBA | ||
| Tue., 12/4 | V Boys Ice Hockey | Pawling (NY) (Scrim.) | Home - Hotchkiss [Directions] | 8:00 p.m. | ||
| Wed., 12/5 | V Boys Ice Hockey | Mt. Everett (MA) (Scrim.) | Home - Hotchkiss [Directions] | 8:00 p.m. | ||
| Wed., 12/5 | V Girls Ice Hockey | East Catholic Coop | Home - Enfield Twin Rinks [Directions] | 4:20 p.m. | L 2-3 | |
| Sat., 12/8 | V Boys Ice Hockey | Shepaug Jamboree | Away - The Gunnery | 7:00 p.m. | ||
| Sat., 12/8 | V Girls Ice Hockey | West Haven/SHA | Home - Enfield Twin Rinks [Directions] | 8:10 p.m. | W 3-2 (OT) | |
| Tue., 12/11 | V Boys Basketball | SMSA (Scrim.) | Away - SMSA [Directions] | 4:00 p.m. | ||
| Tue., 12/11 | V Girls Basketball | Litchfield | Home - NWR-7 Gym [Directions] | 7:00 p.m. | W 38-25 | |
| Tue., 12/11 | JV Girls Basketball | Litchfield | Home - NWR-7 Gym [Directions] | 5:30 p.m. | W 33-16 | |
| Wed., 12/12 | V Wrestling | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/14 | V Boys Basketball | Shepaug Valley | Home - Northwestern Gym [Directions] | 7:00 p.m. | L 37-58 | |
| Fri., 12/14 | JV Boys Basketball | Shepaug Valley | Home - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/14 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 43-37 | |
| Fri., 12/14 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | L 19-30 | |
| Sat., 12/15 | V Wrestling | Skip Arden | Away - Manchester HS | 9:00 a.m. | ||
| Sat., 12/15 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena [Directions] | 8:50 p.m. | W 3-1 | |
| Tue., 12/18 | V Boys Basketball | Lewis Mills | Home - Northwestern Gym [Directions] | 7:00 p.m. | L 46-53 | |
| Tue., 12/18 | V Girls Basketball | Lewis Mills | Home - Northwestern Gym [Directions] | 5:30 p.m. | W 38-24 | |
| Tue., 12/18 | V Girls Ice Hockey | Simsbury | Away - ISCC [Directions] | 7:50 p.m. | L 1-4 | |
| Wed., 12/19 | JV Boys Basketball | Lewis Mills | Home - Northwestern Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/19 | V Boys Ice Hockey | Norwich Free Academy | Away - RoseGarden Ice Arena [Directions] | 5:00 p.m. | W 4-0 | |
| Wed., 12/19 | V Wrestling | Oxford | Away - OHS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/19 | JV Girls Basketball | Lewis Mills | Home - Northwestern Gym [Directions] | 5:30 p.m. | W 26-20 | |
| Thu., 12/20 | V Boys Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 4:30 p.m. | ||
| Fri., 12/21 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 6:00 p.m. | W 57-43 | |
| Fri., 12/21 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/21 | V Boys Ice Hockey | Tri-Town | Home - Hotchkiss [Directions] | 8:15 p.m. | L 2-4 | |
| Fri., 12/21 | V Girls Basketball | Nonnewaug | Home - NWR-7 Gym [Directions] | 6:00 p.m. | W 49-26 | |
| Fri., 12/21 | JV Girls Basketball | Nonnewaug | Home - NWR-7 Gym [Directions] | 4:30 p.m. | W 29-24 | |
| Fri., 12/21 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Enfield Twin Rinks [Directions] | 8:20 p.m. | L 1-5 | |
| Sat., 12/22 | V Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 3:00 p.m. | W 57-53 | |
| Sat., 12/22 | JV Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 12/22 | V Wrestling | Bristol Eastern Quad | Away - Bristol Eastern | 9:00 a.m. | ||
| Sat., 12/22 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden Ice Rink [Directions] | 3:00 p.m. | W 4-0 | |
| Wed., 12/26 | V Wrestling | Gilbert/Torrington | Home - NWR-7 Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/27 | V Wrestling | Monument Mt Tourney | Away - Monument MT HS | 9:00 a.m. | ||
| Thu., 12/27 | V Girls Basketball | Wolcott Tech | Home - Northwestern Gym [Directions] | 5:30 p.m. | W 61-12 | |
| Thu., 12/27 | JV Girls Basketball | Wolcott Tech | Home - Northwestern Gym [Directions] | 4:00 p.m. | W 48-22 | |
| Thu., 12/27 | FR Girls Basketball | Wolcott Tech | Home - Northwestern [Directions] | 2:30 p.m. | W 41-15 | |
| Thu., 12/27 | V Girls Ice Hockey | Daniel Hand Coop | Home - Enfield Twin Rinks [Directions] | 2:10 p.m. | W 9-0 | |
| Fri., 12/28 | V Boys Ice Hockey | Norwich Free Academy | Home - Hotchkiss [Directions] | 8:15 p.m. | T 2-2(OT) | |
| Fri., 12/28 | V Girls Basketball | Wilcox Tech | Home - Northwestern Gym [Directions] | 3:30 p.m. | W 41-11 | |
| Fri., 12/28 | JV Girls Basketball | Wilcox Tech | Home - Northwestern Gym [Directions] | Cancelled | Cancelled | |
| Sat., 12/29 | V Boys Basketball | New Fairfield | Home - Northwestern Gym [Directions] | 6:00 p.m. | L 49-52 | |
| Sat., 12/29 | JV Boys Basketball | New Fairfield | Home - Northwestern Gym [Directions] | 4:15 p.m. | ||
| Sat., 12/29 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 12/29 | V Girls Ice Hockey | Longmeadow (MA) (Scrim.) | Away - Olympia Ice Center | 1:20 p.m. | In West Springfield MA | |
| Wed., 1/2 | V Boys Basketball | Housatonic Regional | Home - Northwestern Gym [Directions] | 7:00 p.m. | W 60-46 | |
| Wed., 1/2 | JV Boys Basketball | Housatonic Regional | Home - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/2 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | 8:20 p.m. | L 4-8 | |
| Wed., 1/2 | V Girls Basketball | Housatonic Regional | Away - Housatonic [Directions] | 7:00 p.m. | L 32-37 | |
| Wed., 1/2 | JV Girls Basketball | Housatonic Regional | Away - Housatonic [Directions] | 5:30 p.m. | W 39-17 | |
| Wed., 1/2 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Center, Cromwell [Directions] | 7:30 p.m. | W 6-3 | |
| Thu., 1/3 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby HS Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 1/4 | V Boys Basketball | Thomaston | Home - Northwestern Gym [Directions] | 7:00 p.m. | W 68-50 | |
| Fri., 1/4 | JV Boys Basketball | Thomaston | Home - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/4 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | W 51-24 | |
| Fri., 1/4 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | W 31-30 | |
| Sat., 1/5 | V Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | 7:00 p.m. | L 3-6 | |
| Sat., 1/5 | V Boys Indoor Track | James Barber Invite | Away - Southern CT | 10:00 a.m. | ||
| Sat., 1/5 | V Wrestling | Tournament Game - Opponent Not Known | Away - Fairfield Warde | 9:00 a.m. | ||
| Sat., 1/5 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | 1:10 p.m. | L 0-2 | |
| Sat., 1/5 | V Girls Indoor Track | James Barber Invite | Away - Southern | 10:00 a.m. | ||
| Mon., 1/7 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Tue., 1/8 | V Boys Basketball | Terryville | Away - Terryville HS [Directions] | 7:00 p.m. | W 51-43 | |
| Tue., 1/8 | JV Boys Basketball | Terryville | Away - Terryville HS [Directions] | 5:30 p.m. | ||
| Tue., 1/8 | V Wrestling | East Haven | Away - East Haven HS [Directions] | 5:30 p.m. | ||
| Tue., 1/8 | V Girls Basketball | Terryville | Home - NWR-7 Gym [Directions] | 6:00 p.m. | W 68-25 | |
| Tue., 1/8 | JV Girls Basketball | Terryville | Home - NWR-7 Gym [Directions] | Cancelled | Cancelled | |
| Wed., 1/9 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | 6:30 p.m. | L 1-2 | |
| Wed., 1/9 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | 4:20 p.m. | L 2-5 | |
| Thu., 1/10 | JV Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/10 | JV Girls Basketball | Gilbert | Away - Gilbert [Directions] | 5:30 p.m. | W 34-15 | |
| Fri., 1/11 | V Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 7:00 p.m. | L 61-66 | |
| Fri., 1/11 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Hotchkiss [Directions] | 8:15 p.m. | W 5-1 | |
| Fri., 1/11 | V Boys Indoor Track | Yale Invite | Away - Cox Cage | TBA | ||
| Fri., 1/11 | V Girls Basketball | Gilbert | Away - Gilbert [Directions] | 5:30 p.m. | W 52-30 | |
| Fri., 1/11 | V Girls Indoor Track | Yale Invite | Away - Cox Cage | TBA | ||
| Sat., 1/12 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 1/12 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | 1:00 p.m. | L 4-8 | |
| Sat., 1/12 | V Boys Indoor Track | Shoreline Coaches Invite | Away - Hill House | TBA | ||
| Sat., 1/12 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/12 | V Wrestling | Tournament Game - Opponent Not Known | Away - Canton | 9:00 a.m. | ||
| Sat., 1/12 | FR Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/12 | V Girls Indoor Track | Shoreline Coaches Invite | Away - Hill House | TBA | ||
| Tue., 1/15 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | L 39-73 | |
| Tue., 1/15 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Tue., 1/15 | V Girls Basketball | Wamogo | Home - NWR-7 Gym [Directions] | 5:30 p.m. | W 56-25 | |
| Tue., 1/15 | JV Girls Basketball | Wamogo | Home - NWR-7 Gym [Directions] | Cancelled | Cancelled | |
| Wed., 1/16 | V Boys Ice Hockey | Newington Coop | Away - Newington Ice Arena - 300 Alumni Rd. in Newington [Directions] | 8:00 p.m. | L 0-6 | |
| Wed., 1/16 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Fri., 1/18 | V Boys Basketball | Litchfield | Home - Northwestern Gym [Directions] | 7:00 p.m. | L 51-66 | |
| Fri., 1/18 | JV Boys Basketball | Litchfield | Home - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/18 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - Hotchkiss [Directions] | 8:15 p.m. | L 3-4 | |
| Fri., 1/18 | V Boys Indoor Track | HK Invite | Away - Hill House | 5:30 p.m. | ||
| Fri., 1/18 | V Girls Indoor Track | HK Invite | Away - Hill House | 5:30 p.m. | ||
| Sat., 1/19 | FR Boys Basketball | Gilbert | Away - Gilbert HS [Directions] | 11:30 p.m. | ||
| Sat., 1/19 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 2:30 p.m. | ||
| Sat., 1/19 | V Wrestling | Tournament Game - Opponent Not Known | Away - East Catholic | 9:00 a.m. | ||
| Sat., 1/19 | FR Girls Basketball | Gilbert | Away - Gilbert HS [Directions] | 10:00 a.m. | ||
| Sat., 1/19 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Enfield Twin Rinks [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 1/22 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 51-59 | |
| Tue., 1/22 | JV Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/22 | V Girls Basketball | Shepaug Valley | Home - NWR-7 Gym [Directions] | 7:00 p.m. | W 49-41 | |
| Tue., 1/22 | JV Girls Basketball | Shepaug Valley | Home - NWR-7 Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/23 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks [Directions] | 3:50 p.m. | L 1-2 | |
| Wed., 1/23 | V Wrestling | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/24 | V Boys Swimming and Diving | Nonnewaug | Away - Crosby HS [Directions] | 5:00 p.m. | ||
| Fri., 1/25 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | W 53-47 | |
| Fri., 1/25 | JV Boys Basketball | Lewis Mills | Away - Har-Bur Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/25 | V Boys Ice Hockey | New Milford | Home - Hotchkiss [Directions] | 8:15 p.m. | L 1-5 | |
| Fri., 1/25 | V Girls Basketball | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 7:15 p.m. | W 43-38 | |
| Fri., 1/25 | JV Girls Basketball | Lewis Mills | Away - Har-Bur Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/25 | V Girls Ice Hockey | Hall/Conard | Home - Enfield Twin Rinks [Directions] | 8:20 p.m. | L 2-3 | |
| Sat., 1/26 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/26 | V Wrestling | Rodney Smith | Away - East Windsor | 9:00 a.m. | ||
| Sat., 1/26 | V Girls Ice Hockey | Avon | Home - Enfield Twin Rinks [Directions] | 8:20 p.m. | W 6-2 | |
| Mon., 1/28 | V Boys Basketball | Nonnewaug | Home - Northwestern Gym [Directions] | 7:00 p.m. | L 41-61 | |
| Mon., 1/28 | JV Boys Basketball | Nonnewaug | Home - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/28 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Mon., 1/28 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 7:00 p.m. | W 53-34 | |
| Mon., 1/28 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/31 | V Wrestling | St. Paul Catholic | Home - NWR-7 Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/31 | V Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 7:00 p.m. | W 49-17 | |
| Thu., 1/31 | JV Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | W 54-27 | |
| Fri., 2/1 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Boys Ice Hockey | Eastern CT Eagles | Home - Hotchkiss [Directions] | 8:15 p.m. | L 3-5 | |
| Fri., 2/1 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Thomaston | Home - NWR-7 Gym [Directions] | 7:00 p.m. | W 40-37 | |
| Fri., 2/1 | JV Girls Basketball | Thomaston | Home - NWR-7 Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/2 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 2/2 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/2 | V Wrestling | Law | Away - Jonathan Law | 9:00 a.m. | ||
| Sat., 2/2 | FR Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/2 | V Girls Ice Hockey | Simsbury | Home - Enfield Twin Rinks [Directions] | 6:10 p.m. | L 1-2 | |
| Mon., 2/4 | V Boys Indoor Track | Last Chance | Away - Hill House | TBA | ||
| Mon., 2/4 | V Girls Indoor Track | Last Chance Invite | Away - Hill House | TBA | ||
| Tue., 2/5 | V Boys Basketball | Terryville | Home - Northwestern Gym [Directions] | 7:00 p.m. | W 38-31 | |
| Tue., 2/5 | JV Boys Basketball | Terryville | Home - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/5 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Terryville | Away - Terryville HS [Directions] | 6:45 p.m. | W 58-34 | |
| Tue., 2/5 | JV Girls Basketball | Terryville | Away - Terryville HS [Directions] | 5:30 p.m. | ||
| Wed., 2/6 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena [Directions] | 5:30 p.m. | W 6-4 | |
| Wed., 2/6 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss [Directions] | 4:30 p.m. | ||
| Wed., 2/6 | V Wrestling | Terryville-Thomaston | Home - NWR-7 Gym [Directions] | 6:00 p.m. | ||
| Fri., 2/8 | V Boys Basketball | Gilbert | Home - Northwestern Home [Directions] | 7:30 p.m. | L 51-67 | |
| Fri., 2/8 | JV Boys Basketball | Gilbert | Home - Northwestern Home [Directions] | 4:30 p.m. | ||
| Fri., 2/8 | V Boys Ice Hockey | Masuk | Home - Hotchkiss [Directions] | 8:15 p.m. | W 4-0 | |
| Fri., 2/8 | V Boys Swimming and Diving | Torrington | Home - Winsted YMCA [Directions] | 7:00 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Gilbert | Home - NWR-7 Gym [Directions] | 6:00 p.m. | W 50-41 | |
| Fri., 2/8 | JV Girls Basketball | Gilbert | Home - NWR-7 Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/8 | V Girls Ice Hockey | Longmeadow (MA) (Scrim.) | Home - Enfield Twin Rinks [Directions] | 9:20 p.m. | L 2-4 | |
| Sat., 2/9 | V Wrestling | BL/NV Tournament | Away | 9:00 a.m. | ||
| Sat., 2/9 | V Girls Ice Hockey | Northwest Catholic | Home - Enfield Twin Rinks [Directions] | 4:00 p.m. | W 3-1 | Senior Night!! |
| Mon., 2/11 | V Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | 7:00 p.m. | L 58-65 | |
| Mon., 2/11 | JV Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | 5:30 p.m. | ||
| Mon., 2/11 | V Girls Basketball | Housatonic Regional | Home - NWR-7 Gym [Directions] | 7:00 p.m. | L 20-41 | |
| Mon., 2/11 | JV Girls Basketball | Housatonic Regional | Home - NWR-7 Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/11 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | 4:10 p.m. | W 7-1 | |
| Wed., 2/13 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Thu., 2/14 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 6:00 p.m. | W 49-35 | |
| Thu., 2/14 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | Cancelled | Cancelled | |
| Fri., 2/15 | V Boys Basketball | Wamogo | Home - Northwestern Gym [Directions] | 7:00 p.m. | L 50-95 | |
| Fri., 2/15 | JV Boys Basketball | Wamogo | Home - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/15 | V Boys Ice Hockey | JBWA | Home - Hotchkiss [Directions] | 8:15 p.m. | L 2-6 | |
| Sat., 2/16 | V Boys Swimming and Diving | Gilbert | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/16 | V Girls Basketball | Shepaug Valley | Home - Northwestern Gym [Directions] | 5:00 p.m. | W 35-22 | |
| Sat., 2/16 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | 6:00 p.m. | L 3-5 | |
| Mon., 2/18 | V Boys Ice Hockey | Woodstock Academy | Home - Hotchkiss [Directions] | 1:30 p.m. | T 1-1 | |
| Tue., 2/19 | V Girls Basketball | Gilbert | Home - Northwestern Gym [Directions] | 5:30 p.m. | W 35-33 | |
| Tue., 2/19 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | 8:00 p.m. | L 0-1 | |
| Thu., 2/21 | V Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 7:00 p.m. | L 56-68 | |
| Thu., 2/21 | JV Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Fri., 2/22 | V Girls Basketball | Housatonic Regional | Home - Northwestern Gym [Directions] | 7:00 p.m. | L 37-45 | |
| Sat., 2/23 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 11:00 a.m. | L 54-79 | |
| Sat., 2/23 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - Gunnery Rink [Directions] | 7:00 p.m. | W 3-1 | |
| Sat., 2/23 | V Boys Swimming and Diving | Splash Classic | Away | TBA | ||
| Mon., 2/25 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | 8:00 p.m. | L 2-6 | |
| Mon., 2/25 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Enfield Twin Rinks [Directions] | 8:10 p.m. | W 5-0 | State Tournament |
| Tue., 2/26 | V Girls Basketball | Amistad | Home - Northwestern Gym [Directions] | 6:00 p.m. | W 55-41 | |
| Thu., 2/28 | V Boys Ice Hockey | Brookfield | Home - Hotchkiss [Directions] | 8:00 p.m. | W 7-3 | |
| Fri., 3/1 | V Boys Swimming and Diving | BL Diving | Away | TBA | ||
| Fri., 3/1 | V Wrestling | New England's | Away | TBA | ||
| Fri., 3/1 | V Girls Basketball | Jonathan Law | Home - Northwestern Gym [Directions] | 7:00 p.m. | L 48-79 | |
| Sat., 3/2 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 6:00 p.m. | L 0-3 | QF Game |
| Sun., 3/3 | V Boys Swimming and Diving | BL Swim Championships | Away - Hotchkiss | 1:00 p.m. | ||
| Mon., 3/4 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena [Directions] | 5:30 p.m. | ||
| Tue., 3/5 | V Boys Basketball | Stonington | Away - SHS Main Gymnasium [Directions] | 6:00 p.m. | L 52-76 | |
| Thu., 3/7 | V Boys Ice Hockey | CIAC Tourney Quarterfinals | Away - Site TBA | Cancelled | Cancelled | |
| Thu., 3/7 | V Boys Swimming and Diving | State Diving | Away | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | State Trials | Away | TBA | ||
| Mon., 3/11 | V Boys Ice Hockey | CIAC Tourney Semifinals | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Mon., 3/11 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away | 5:00 p.m. | ||
| Thu., 3/14 | V Boys Ice Hockey | CIAC Tourney Final | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Thu., 3/14 | V Boys Swimming and Diving | Opens | Away - Yale | 7:00 p.m. | ||
| Mon., 4/1 | V Baseball | Nonnewaug | Away - Nonnewaug HS [Directions] | 3:45 p.m. | W 11-10 | |
| Mon., 4/1 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | 3:45 p.m. | W 23-2 | |
| Mon., 4/1 | V Boys Tennis | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 4/1 | V Softball | Nonnewaug | Away - Nonnewaug Varsity Softball Field [Directions] | 3:45 p.m. | W 8-5 | |
| Mon., 4/1 | V Girls Tennis | Litchfield | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/2 | V Boys Outdoor Track | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Girls Outdoor Track | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Baseball | Terryville | Away - Terryville HS [Directions] | 3:45 p.m. | W 23-18 | |
| Wed., 4/3 | JV Baseball | Terryville | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 11-1 | |
| Wed., 4/3 | V Boys Tennis | Nonnewaug | Away - Edgewood Tennis & Bath [Directions] | 3:45 p.m. | L 2-3 | |
| Wed., 4/3 | V Softball | Terryville | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 20-5 | |
| Wed., 4/3 | V Girls Tennis | Nonnewaug | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 4/4 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 4/4 | V Girls Tennis | Wamogo | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Sat., 4/6 | V Baseball | Gilbert | Away - Walker Field [Directions] | 2:00 p.m. | W 4-2 | |
| Tue., 4/9 | V Baseball | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | W 11-1 | |
| Tue., 4/9 | JV Baseball | Housatonic Regional | Away - Housatonic HS [Directions] | 3:45 p.m. | W 6-2 | |
| Tue., 4/9 | V Boys Golf | Lewis Mills | Away - Fairview Farms Golf Course - Harwinton [Directions] | 3:00 p.m. | Northwestern 215 Lewis Mills 159 | |
| Wed., 4/10 | V Baseball | Lewis Mills | Away - Lewis Mills HS [Directions] | 3:45 p.m. | W 5-3 | |
| Wed., 4/10 | V Boys Golf | Gilbert | Away - Greenwood Country Club [Directions] | 3:00 p.m. | Northwestern 213 Gilbert 188 | |
| Wed., 4/10 | V Boys Outdoor Track | Lewis Mills | Away - Lewis Mills Track [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Outdoor Track | Lewis Mills | Away - Lewis Mills Track [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 4/10 | JV Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/11 | JV Baseball | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 2-13 | |
| Thu., 4/11 | V Boys Golf | Litchfield, Lewis Mills | Away - Litchfield Country club [Directions] | 3:00 p.m. | Northwestern 204 Lewis Mills 167 Litchfield 231 | |
| Thu., 4/11 | V Boys Tennis | Thomaston | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 4/11 | V Softball | Gilbert | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 16-0 | |
| Thu., 4/11 | JV Softball | Gilbert | Home - Northwestern Field [Directions] | 3:45 p.m. | ||
| Fri., 4/12 | V Baseball | Litchfield | Away - Litchfield HS Baseball Field [Directions] | 3:45 p.m. | W 17-0 | |
| Fri., 4/12 | V Softball | Litchfield | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 16-0 | |
| Sat., 4/13 | JV Softball | Thomaston | Home - NWR Varsity Field [Directions] | Cancelled | Cancelled | |
| Tue., 4/16 | V Baseball | Thomaston | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 3-2 | |
| Wed., 4/17 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | 1:30 p.m. | W 7-1 | |
| Wed., 4/17 | JV Softball | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 10:00 a.m. | W 10-4 | |
| Wed., 4/17 | JV Softball | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 11:30 a.m. | W 3-0 | |
| Wed., 4/17 | V Girls Tennis | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/18 | V Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | 1:00 p.m. | L 1-2 | |
| Thu., 4/18 | JV Baseball | Shepaug Valley | Home - Northwestern Varsity Field [Directions] | 1:00 p.m. | ||
| Thu., 4/18 | V Softball | Shepaug Valley | Home - Northwestern Varsity Field [Directions] | 1:00 p.m. | W 19-9 | |
| Fri., 4/19 | JV Softball | Wolcott Tech | Home - Northwestern Varsity Field [Directions] | 10:00 a.m. | W 24-0 | |
| Fri., 4/19 | JV Softball | Wilcox Tech | Home - Northwestern Varsity Field [Directions] | 11:30 a.m. | W 18-4 | |
| Tue., 4/23 | V Boys Golf | Wamogo, Nonnewaug | Away [Directions] | 3:00 p.m. | Northwestern 219 Wamogo 233 | |
| Tue., 4/23 | V Boys Outdoor Track | Shepaug Valley, Nonnewaug | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Tue., 4/23 | V Girls Outdoor Track | Shepaug Valley, Nonnewaug | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Shepaug Valley | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 4/24 | V Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | 3:45 p.m. | W 11-2 | |
| Wed., 4/24 | V Boys Tennis | Litchfield | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 4/24 | V Softball | Wamogo/Litchfield | Away - Wamogo Varsity Softball Field [Directions] | 3:45 p.m. | W 9-5 | |
| Wed., 4/24 | V Girls Tennis | Litchfield | Away - Litchfield HS [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 4/25 | V Boys Golf | Housatonic Regional, Shepaug Valley | Away - Sharon CC [Directions] | 3:00 p.m. | Northwestern 202 Housatonic 191 Shepaug 233 | |
| Thu., 4/25 | V Boys Tennis | Housatonic Regional | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 4/25 | V Softball | Housatonic Regional | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 15-0 | |
| Thu., 4/25 | V Girls Tennis | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/27 | JV Softball | Lewis Mills | Home - Northwestern Varsity Field [Directions] | Cancelled | Cancelled | |
| Mon., 4/29 | V Baseball | Terryville | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 15-0 | |
| Mon., 4/29 | JV Baseball | Terryville | Away - Terryville HS [Directions] | 3:45 p.m. | W 16-1 | |
| Mon., 4/29 | V Boys Golf | Litchfield, Wamogo | Away - Stonybrook GC [Directions] | 3:00 p.m. | Northwestern 215 Litchfield 224 Wamogo 232 | |
| Mon., 4/29 | V Boys Tennis | Wamogo | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Mon., 4/29 | V Softball | Terryville | Away - Terryville HS [Directions] | 3:45 p.m. | W 19-0 | |
| Mon., 4/29 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 4/30 | V Boys Golf | Lewis Mills, Terryville | Away - Fairview Farms Golf Course - Harwinton [Directions] | 3:00 p.m. | Northwestern 213 Lewis Mills 165 Terryville/Thomaston 228 | |
| Tue., 4/30 | V Boys Outdoor Track | Terryville | Away [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Terryville | Away [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | Housatonic Regional | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 17-5 | |
| Wed., 5/1 | JV Baseball | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | W 14-3 | |
| Wed., 5/1 | V Boys Golf | Shepaug Valley | Home - Norfolk CC [Directions] | 3:00 p.m. | Northwestern 198 Shepaug 232 | |
| Wed., 5/1 | V Boys Tennis | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | L 2-3 | |
| Wed., 5/1 | V Softball | Housatonic Regional | Away - Housatonic [Directions] | 3:45 p.m. | W 16-1 | |
| Wed., 5/1 | V Girls Tennis | Housatonic Regional | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/2 | V Boys Golf | Tournament Game - Opponent Not Known | Away - Oxford Greens CC | 8:00 a.m. | Northwestern (f) 211 | |
| Thu., 5/2 | V Boys Outdoor Track | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Outdoor Track | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | ||
| Sat., 5/4 | V Softball | Nonnewaug | Home - Riverton Field 400 West River Rd., Barkhamsted [Directions] | 3:30 p.m. | W 10-7 | |
| Mon., 5/6 | V Baseball | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 6-3 | |
| Mon., 5/6 | JV Baseball | Lewis Mills | Away - Lewis Mills HS [Directions] | 3:45 p.m. | L 4-9 | |
| Mon., 5/6 | V Boys Golf | Lewis Mills, Housatonic Regional | Home - Norfolk CC [Directions] | 3:45 p.m. | Northwestern 212 Lewis Mills 170 Housatonic 198 | |
| Mon., 5/6 | V Boys Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 5/6 | V Softball | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 5/6 | JV Softball | Lewis Mills | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 14-1 | |
| Mon., 5/6 | V Girls Tennis | Lewis Mills | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 5/7 | V Baseball | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 8-0 | |
| Tue., 5/7 | JV Baseball | Nonnewaug | Home - Riverton [Directions] | 3:45 p.m. | L 7-8 | |
| Tue., 5/7 | V Boys Outdoor Track | Wamogo, Wolcott Tech | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Wamogo, Wolcott Tech | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Nonnewaug | Away - Woodbury MS [Directions] | 3:45 p.m. | L 3-4 | |
| Wed., 5/8 | V Baseball | Litchfield | Home - Northwestern Varsity Field [Directions] | 4:15 p.m. | W 12-1 | |
| Wed., 5/8 | V Boys Tennis | Shepaug Valley | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Wed., 5/8 | V Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | W 15-0 | |
| Wed., 5/8 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/9 | V Boys Tennis | Nonnewaug | Home - NWR-7 Tennis Courts [Directions] | 4:30 p.m. | W 3-2 | |
| Thu., 5/9 | JV Softball | Granby Memorial | Home - Northwestern JV field [Directions] | 4:00 p.m. | W 17-2 | |
| Fri., 5/10 | V Baseball | Granby Memorial | Home - Northwestern Varsity Field [Directions] | 4:00 p.m. | L 6-7 | |
| Fri., 5/10 | JV Baseball | Granby Memorial | Away - Granby Memorial HS [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Boys Golf | Tournament Game - Opponent Not Known | Away - Blue Fox Run | TBA | Northwestern 201 | bus 11:35am |
| Fri., 5/10 | V Softball | Granby Memorial | Away - Granby Memorial HS [Directions] | 4:00 p.m. | W 5-1 | |
| Sat., 5/11 | JV Softball | Wolcott Tech | Home - Northwestern Varsity Field [Directions] | 10:00 a.m. | W 14-0 | Thomaston 18 NW 3, NW 19-OWTS 0 |
| Mon., 5/13 | V Boys Tennis | Gilbert | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 5/13 | V Girls Tennis | Gilbert | Away - Gilbert [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/14 | V Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 5/14 | V Boys Outdoor Track | Thomaston, Wamogo, Gilbert | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Outdoor Track | Thomaston, Wamogo, Gilbert | Home - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Tennis | Granby Memorial | Away - Granby Memorial HS [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/15 | JV Baseball | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 5/15 | V Boys Golf | Gilbert, Litchfield, Terryville | Home - Norfolk CC [Directions] | 3:45 p.m. | Northwestern 194 Gilbert 182 Litchfield 233 Terryville 199 | |
| Wed., 5/15 | V Boys Tennis | Lewis Mills | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Wed., 5/15 | V Softball | Gilbert | Away - Rowley Field [Directions] | 3:45 p.m. | W 15-4 | |
| Wed., 5/15 | JV Softball | Gilbert | Away - Rowley Field [Directions] | 3:45 p.m. | W 19-2 | |
| Wed., 5/15 | V Girls Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 5/16 | V Baseball | Gilbert | Home - Northwestern Varsity Field [Directions] | 4:30 p.m. | W 10-1 | |
| Thu., 5/16 | V Boys Golf | Gilbert | Away - Greenwood Country Club [Directions] | 3:00 p.m. | Northwestern 210 Gilbert 180 (played at Norfolk Country Club) | |
| Thu., 5/16 | V Boys Tennis | Thomaston | Away - Nystroms Park [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 5/16 | V Softball | Canton | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 15-0 | |
| Thu., 5/16 | V Girls Tennis | Gilbert | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 5/17 | V Boys Tennis | Berkshire League Championships | Away - Hotchkiss | |||
| Sat., 5/18 | JV Baseball | Wamogo | Home - Northwestern Varsity Field [Directions] | 10:00 a.m. | W 6-4 | |
| Sat., 5/18 | V Boys Outdoor Track | BL Tournament | Away - Litchfield HS | 9:00 a.m. | ||
| Sat., 5/18 | V Girls Outdoor Track | BL Tournament | Away - Litchfield HS | 9:00 a.m. | ||
| Sat., 5/18 | JV Softball | Nonnewaug | Home - Northwestern Varsity Field [Directions] | 10:00 a.m. | W 6-4 won 7-1 | |
| Mon., 5/20 | V Baseball | Wamogo | Home - Northwestern's Field [Directions] | 3:45 p.m. | L 1-3 | |
| Mon., 5/20 | V Boys Golf | Housatonic Regional, Nonnewaug | Home - Norfolk CC [Directions] | 3:45 p.m. | Northwestern 198 Housatonic 182 Nonnewaug 238 | |
| Mon., 5/20 | V Softball | Wamogo/Litchfield | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 16-1 5 innings | |
| Mon., 5/20 | V Girls Tennis | BL Championships | Away - Hotchkiss | 7:30 a.m. | ||
| Tue., 5/21 | V Baseball | Shepaug Valley | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | W 4-2 | |
| Tue., 5/21 | JV Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | 3:45 p.m. | W 14-1 | |
| Tue., 5/21 | V Boys Outdoor Track | BL Festival | Away - Housatonic | 4:00 p.m. | ||
| Tue., 5/21 | V Boys Tennis | Berkshire League | Away - Nystrom Park | |||
| Tue., 5/21 | V Girls Outdoor Track | BL Festival | Away - Housatonic | 4:00 p.m. | ||
| Tue., 5/21 | V Softball | Thomaston | Home - Northwestern Varsity Field [Directions] | 4:00 p.m. | W 18-3 | |
| Tue., 5/21 | JV Softball | St. Paul Catholic | Home - Northwestern JV field [Directions] | 3:45 p.m. | W 17-1 | |
| Tue., 5/21 | V Girls Tennis | Thomaston | Home - NWR-7 Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/22 | V Baseball | Avon | Away - Buckingham Field [Directions] | 3:45 p.m. | W 8-2 | |
| Wed., 5/22 | JV Baseball | Avon | Away - Avon HS [Directions] | 3:45 p.m. | W 13-2 | |
| Wed., 5/22 | V Boys Golf | Nonnewaug | Away - Heritage Village CC [Directions] | 3:00 p.m. | Northwestern 201 Nonnewaug 236 | |
| Wed., 5/22 | V Softball | Shepaug Valley | Away - Dick Ayer Field [Directions] | 3:45 p.m. | W 16-3 | |
| Wed., 5/22 | V Girls Tennis | BL Tournament | Away - Nystrom Psrk | |||
| Thu., 5/23 | JV Baseball | Wamogo | Home - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 5/24 | V Boys Tennis | State Individual | Away - Conard HS | 8:30 a.m. | ||
| Fri., 5/24 | V Girls Tennis | Jonathan Law | Home - NWR-7 Tennis Courts [Directions] | 3:00 p.m. | ||
| Sat., 5/25 | JV Baseball | Tournament Game - Opponent Not Known | Away | 11:00 a.m. | ||
| Sat., 5/25 | V Girls Tennis | States | Away | |||
| Wed., 5/29 | V Baseball | Ansonia | Home - Northwestern Varsity Field [Directions] | 2:30 p.m. | W 3-2 in 9 | |
| Wed., 5/29 | V Boys Outdoor Track | States Class M | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 5/29 | V Girls Outdoor Track | State Class M | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 5/29 | V Softball | Bethel | Home - Northwestern Varsity Field [Directions] | 2:00 p.m. | W 15-0 in 5 | |
| Thu., 5/30 | V Baseball | Ellington | Home - Northwestern Varsity Field [Directions] | 3:30 p.m. | W 5-1 | |
| Thu., 5/30 | V Softball | Granby Memorial | Home - Northwestern Varsity Field [Directions] | 4:00 p.m. | L 3-5 | |
| Sat., 6/1 | V Baseball | St. Joseph | Home - Northwestern Varsity Field [Directions] | 4:00 p.m. | L 1-14 | |
| Sat., 6/1 | JV Softball | Gilbert | Home - Northwestern Varsity Field [Directions] | Cancelled | Cancelled | |
| Mon., 6/3 | V Boys Outdoor Track | State Opens | Away - Willow Brook PArk | 1:30 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | State Opens | Away - Willos Brook Park | 1:30 p.m. | ||