| Simsbury 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1080 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Avon | Home - Simsbury HS [Directions] | Cancelled | ||
| TBA | JV Baseball | Farmington | Away - Farmington HS [Directions] | Cancelled | w/Varsity | |
| TBA | FR Baseball | Maloney | Home - Simsbury HS [Directions] | 4:30 p.m. | ||
| TBA | FR Baseball | Newington | Away - Alumni VAR Baseball Fld on Alumni Rd. [Directions] | 4:45 p.m. | 3:00 pm | |
| TBA | FR Baseball | Farmington | Away - Farmington HS [Directions] | TBA | 2:45 pm | |
| TBA | FR Football | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 3:00 p.m. | 2:20 pm | |
| TBA | JV Boys Ice Hockey | Westminster | Away | 6:15 p.m. | no bus | |
| TBA | JV Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | TBA | 4:30 pm | |
| TBA | FR Boys Lacrosse | Avon | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| TBA | FR Boys Lacrosse | Southington | Away - SubVarsity Lacrosse/Soccer [Directions] | TBA | 2:45 pm | |
| TBA | V Boys Outdoor Track | Tournament Game - Opponent Not Known | Away | Cancelled | ||
| TBA | JV Boys Soccer | Enfield | Away - Enfield H.S. [Directions] | 3:45 p.m. | w/Varsity | |
| TBA | FR Boys Soccer | Farmington | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| TBA | FR Boys Soccer | Granby Memorial | Home - Henry James MS [Directions] | TBA | ||
| TBA | FR Boys Soccer | Southington | Away - SubVarsity Lacrosse/Soccer [Directions] | TBA | 2:20 pm | |
| TBA | JV Boys Volleyball | Tournament Game - Opponent Not Known | Home [Directions] | TBA | ||
| TBA | FR Field Hockey | Hall-0-ween Field Hockey Jamboree | Away - Hall HS | 9:00 a.m. | 8:00 am | |
| TBA | FR Field Hockey | Avon | Away - Avon HS [Directions] | 3:45 p.m. | 2:20 pm | |
| TBA | FR Field Hockey | Enfield | Home - Simsbury HS - Grass Field [Directions] | TBA | ||
| TBA | FR Girls Lacrosse | Avon | Away - Fisher Meadow [Directions] | TBA | 2:45 pm | |
| TBA | V Girls Outdoor Track | Tournament Game - Opponent Not Known | Away | Cancelled | ||
| TBA | V Girls Soccer | South Windsor (Scrim.) | Away - SWHS Multi-Purpose Grass Field [Directions] | TBA | 2:20 pm | |
| TBA | V Girls Soccer | Granby Memorial (Scrim.) | Away - Granby Memorial HS [Directions] | TBA | 3:00 pm | |
| TBA | JV Girls Soccer | New Britain | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Soccer | Bristol Central | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Soccer | South Windsor (Scrim.) | Away - Nevers Road Park - South Windsor [Directions] | TBA | w/Varsity | |
| TBA | FR Girls Soccer | Suffield | Away - Suffield HS [Directions] | 3:45 p.m. | 2:20 pm | |
| TBA | FR Girls Soccer | Enfield | Away - Enfield HS [Directions] | 3:45 p.m. | 2:20 pm | |
| TBA | JV Softball | Northwest Catholic | Home - Memorial Park Softball Field [Directions] | TBA | ||
| TBA | V Girls Tennis | Newington | Home - Simsbury HS [Directions] | Cancelled | ||
| TBA | Unified Sports Basketball | Unified Basketball Level 2 v NFA | Home - Simsbury HS [Directions] | 3:00 p.m. | ||
| TBA | Unified Sports Basketball | CIAC Tournament | Home - Simsbury HS [Directions] | 3:00 p.m. | ||
| TBA | Unified Sports Track | Newington | Away [Directions] | 3:00 p.m. | 2:00 pm | |
| Wed., 8/22 | V Football | Gilbert/NWC/Bacon Academy | Home - Simsbury HS - Holden Field (turf) [Directions] | 9:00 a.m. | ||
| Sat., 8/25 | V Football | Wethersfield (Scrim.) | Home - Simsbury HS - Holden Field (turf) [Directions] | 1:30 p.m. | ||
| Thu., 8/30 | V Boys Soccer | Avon Old Farms (Scrim.) | Home - Simsbury HS - Holden Field (turf) [Directions] | 6:00 p.m. | ||
| Fri., 8/31 | V Boys Cross Country | Cheshire (Scrim.) | Home - Stratton Brook [Directions] | 3:45 p.m. | ||
| Fri., 8/31 | V Football | Platt (Scrim.) | Away [Directions] | 5:30 p.m. | 3 busses at 3:30 pm | |
| Fri., 8/31 | V Girls Cross Country | Cheshire (Scrim.) | Home - Stratton Brook [Directions] | 3:45 p.m. | ||
| Fri., 8/31 | V Field Hockey | Longmeadow (MA) (Scrim.) | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:30 p.m. | ||
| Sat., 9/1 | V Boys Soccer | Berlin Jamboree | Away - Berlin HS | 8:40 a.m. | 7:30 am | |
| Sat., 9/1 | V Girls Volleyball | Avon (Scrim.) | Away [Directions] | 9:00 a.m. | 8:00 am | |
| Wed., 9/5 | V Field Hockey | Ethel Walker School (Scrim.) | Away | 4:00 p.m. | 3:00 pm | |
| Fri., 9/7 | V Football | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | L 26-31 | ||
| Fri., 9/7 | V Boys Soccer | Farmington | Away - Tunxis Mead Park [Directions] | L 0-2 | 3:30 pm | |
| Fri., 9/7 | JV Boys Soccer | Farmington | Home - Simsbury HS - Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Sideline Cheerleading | Varsity Football vs Hall HS | Home - Simsbury HS - Holden Field (turf) [Directions] | 7:00 p.m. | ||
| Fri., 9/7 | V Field Hockey | Hotchkiss (Scrim.) | Away | 4:00 p.m. | 2:20 pm | |
| Fri., 9/7 | V Girls Soccer | Farmington | Away - Tunxis Mead Park [Directions] | T 4-4 | 5:15 pm | |
| Fri., 9/7 | JV Girls Soccer | Farmington | Away - Tunxis Mead Park [Directions] | 4:30 p.m. | 3:15 pm | |
| Fri., 9/7 | V Girls Volleyball | Farmington | Home - Simsbury HS [Directions] | L 0-3 | ||
| Fri., 9/7 | JV Girls Volleyball | Farmington | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | FR Girls Volleyball | Farmington | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Sat., 9/8 | JV Football | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | 10:00 a.m. | ||
| Sat., 9/8 | FR Football | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | 12:30 p.m. | ||
| Tue., 9/11 | V Boys Cross Country | Farmington, Conard | Home - Stratton Brook [Directions] | 3:45 p.m. | ||
| Tue., 9/11 | V Boys Soccer | Avon | Home - Simsbury HS [Directions] | T 1-1(OT) | ||
| Tue., 9/11 | V Girls Cross Country | Farmington, Conard | Home - Stratton Brook [Directions] | 3:45 p.m. | ||
| Tue., 9/11 | V Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | L 2-5 | 2:20 pm | |
| Tue., 9/11 | JV Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 6:00 p.m. | w/Varsity | |
| Tue., 9/11 | V Girls Soccer | Avon | Home - Simsbury HS - Holden Field (turf) [Directions] | W 3-0 | ||
| Tue., 9/11 | JV Girls Soccer | Avon | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Tue., 9/11 | V Girls Volleyball | Avon | Away - Avon HS [Directions] | L 0-3 | 2:45 pm | |
| Tue., 9/11 | JV Girls Volleyball | Avon | Away - Avon HS [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 9/11 | FR Girls Volleyball | Avon | Away - Avon HS--Gym Two [Directions] | 4:00 p.m. | w/Varsity | |
| Thu., 9/13 | FR Football | Southington | Home - Weatogue Field [Directions] | 3:45 p.m. | 3 PM Shuttle to Weatogue Park | |
| Thu., 9/13 | V Boys Soccer | Platt | Home - Simsbury HS - Holden Field (turf) [Directions] | W 2-0 | ||
| Thu., 9/13 | JV Boys Soccer | Platt | Home - Simsbury HS - Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 9/13 | FR Boys Soccer | Enfield | Away - ANNEX (OLD FERMI HIGH SCHOOL) [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 9/13 | FR Field Hockey | Hall | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Plainville | Away [Directions] | W 3-0 | 2:20 pm | |
| Thu., 9/13 | V Girls Volleyball | Berlin | Home - Simsbury HS [Directions] | W 3-0 | ||
| Thu., 9/13 | JV Girls Volleyball | Berlin | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | FR Girls Volleyball | Berlin | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Football | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | L 7-21 | ||
| Fri., 9/14 | V Sideline Cheerleading | Varsity Football vs Southington HS | Home - Simsbury HS - Holden Field (turf) [Directions] | 7:00 p.m. | ||
| Fri., 9/14 | V Field Hockey | Cheshire | Away - Cheshire High Main Game field [Directions] | L 0-6 | 2:20 pm | |
| Fri., 9/14 | JV Field Hockey | Cheshire | Away - Cheshire High Field Hockey field [Directions] | 5:30 p.m. | w/Varsity | |
| Fri., 9/14 | FR Field Hockey | Enfield | Away - Enfield HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Sat., 9/15 | V Boys Cross Country | Stratton Brook Park XC Invitational | Home - Stratton Brook [Directions] | 9:00 a.m. | ||
| Sat., 9/15 | JV Football | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | V Girls Cross Country | Stratton Brook Park XC Invitational | Home - Stratton Brook [Directions] | 9:00 a.m. | ||
| Mon., 9/17 | V Boys Cross Country | East Catholic | Home - Stratton Brook [Directions] | 3:45 p.m. | ||
| Mon., 9/17 | V Girls Cross Country | East Catholic | Home - Stratton Brook [Directions] | 3:45 p.m. | ||
| Mon., 9/17 | V Field Hockey | Conard | Away - Conard HS Stadium [Directions] | L 0-4 | 3:15 pm | |
| Mon., 9/17 | JV Field Hockey | Conard | Away - Conard HS [Directions] | 4:30 p.m. | w/Varsity | |
| Mon., 9/17 | V Girls Soccer | E.O. Smith | Home - Simsbury HS - Holden Field (turf) [Directions] | L 0-2 | ||
| Mon., 9/17 | JV Girls Soccer | E.O. Smith | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 9/17 | FR Girls Soccer | Conard | Away - Duffy Elementary School [Directions] | 3:45 p.m. | 2:20 pm | |
| Mon., 9/17 | V Girls Volleyball | East Catholic | Away - Rev. Robert Saunders Gymnasium [Directions] | W 3-2 | 2:45 pm | |
| Mon., 9/17 | JV Girls Volleyball | East Catholic | Away - Rev. Robert Saunders Gymnasium [Directions] | 4:00 p.m. | w/Varsity | |
| Mon., 9/17 | FR Girls Volleyball | East Catholic | Away - Rev. Robert Saunders Gymnasium [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 9/18 | V Boys Soccer | Enfield | Away - Enfield H.S. [Directions] | W 2-0 | 2:20 pm | |
| Thu., 9/20 | FR Football | East Hartford | Away - East Hartford HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Fri., 9/21 | V Boys Cross Country | Sloper Relays | Away - Southington HS | Cancelled | 2:20 pm | |
| Fri., 9/21 | V Football | East Hartford | Away - East Hartford HS [Directions] | L 27-28 | 3 busses at 3:30 pm | |
| Fri., 9/21 | V Boys Soccer | Northwest Catholic | Away - Northwest Catholic HS [Directions] | W 2-1 | 2:20 pm | |
| Fri., 9/21 | JV Boys Soccer | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 3:45 p.m. | w/Varsity | |
| Fri., 9/21 | V Sideline Cheerleading | Varsity Football at East Hartford HS | Away - East Hartford HS | 6:30 p.m. | 4:30 pm | |
| Fri., 9/21 | V Girls Cross Country | Sloper Relay | Away - Southington HS | Cancelled | w/Boys | |
| Fri., 9/21 | V Field Hockey | Granby Memorial | Home - Simsbury HS - Holden Field (turf) [Directions] | L 0-1 | ||
| Fri., 9/21 | JV Field Hockey | Granby Memorial | Home - Simsbury HS - Grass Field [Directions] | 5:15 p.m. | ||
| Fri., 9/21 | V Girls Soccer | Northwest Catholic | Home - Simsbury HS - Holden Field (turf) [Directions] | W 2-1 | ||
| Fri., 9/21 | JV Girls Soccer | Northwest Catholic | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Fri., 9/21 | V Girls Volleyball | Wethersfield | Home - Simsbury HS [Directions] | W 3-1 | ||
| Fri., 9/21 | JV Girls Volleyball | Wethersfield | Home - Simsbury HS [Directions] | 5:00 p.m. | ||
| Fri., 9/21 | FR Girls Volleyball | Wethersfield | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Sat., 9/22 | JV Football | East Hartford | Away - East Hartford HS [Directions] | 10:00 a.m. | 7:30 am | |
| Mon., 9/24 | FR Boys Soccer | Bristol Central | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 9/24 | V Field Hockey | E.O. Smith | Home - Simsbury HS - Holden Field (turf) [Directions] | W 4-1 | ||
| Mon., 9/24 | JV Field Hockey | E.O. Smith | Home - Simsbury HS - Holden Field (turf) [Directions] | 5:15 p.m. | ||
| Mon., 9/24 | FR Field Hockey | Wethersfield | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 9/24 | V Girls Volleyball | Northwest Catholic | Away - Northwest Catholic HS [Directions] | W 3-0 | 2:45 pm | |
| Mon., 9/24 | JV Girls Volleyball | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 4:00 p.m. | w/Varsity | |
| Mon., 9/24 | FR Girls Volleyball | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 9/25 | V Boys Soccer | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | L 0-2 | ||
| Tue., 9/25 | V Girls Volleyball | New Britain | Away - New Britain HS [Directions] | W 3-1 | 2:45 pm | |
| Tue., 9/25 | JV Girls Volleyball | New Britain | Away - New Britain HS [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 9/25 | FR Girls Volleyball | New Britain | Away - New Britain HS [Directions] | 4:00 p.m. | w/Varsity | |
| Wed., 9/26 | V Boys Cross Country | Avon, Northwest Catholic, International | Away - Fisher Meadow [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 9/26 | FR Boys Soccer | Newington | Home - Simsbury HS - Grass Field [Directions] | 4:15 p.m. | ||
| Wed., 9/26 | V Girls Cross Country | Avon, Northwest Catholic, International | Away - Fisher Meadow [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 9/26 | V Field Hockey | Hamden | Home - Simsbury HS - Holden Field (turf) [Directions] | L 0-3 | Senior Night | |
| Wed., 9/26 | JV Field Hockey | Hamden | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:30 p.m. | ||
| Thu., 9/27 | FR Football | New Britain | Away - Veteran's Stadium in Willow Brook Park [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 9/27 | V Field Hockey | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | W 3-2 | ||
| Thu., 9/27 | JV Field Hockey | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | 5:30 p.m. | ||
| Fri., 9/28 | V Football | New Britain | Away - Veteran's Stadium in Willow Brook Park [Directions] | L 7-30 | 3 busses at 3:30 pm | |
| Fri., 9/28 | V Sideline Cheerleading | Varsity Football at New Britain HS | Away - New Britain HS | 6:30 p.m. | 4:30 pm | |
| Fri., 9/28 | V Field Hockey | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | L 0-4 | 4:45 pm | |
| Fri., 9/28 | JV Field Hockey | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 7:30 p.m. | w/Varsity | |
| Fri., 9/28 | V Girls Soccer | New Britain | Home - Simsbury HS - Holden Field (turf) [Directions] | W 5-0 | ||
| Sat., 9/29 | V Boys Crew | Riverfront Regatta | Away - Riverfront Boathouse, Hartford CT | TBA | 2 buses at 7:45 am | |
| Sat., 9/29 | JV Football | New Britain | Away - Veteran's Stadium in Willow Brook Park [Directions] | 10:00 a.m. | 7:30 am | |
| Sat., 9/29 | V Girls Crew | Riverfront Regatta | Away - Riverfront Boathouse, Hartford CT | TBA | w/Boys | |
| Mon., 10/1 | FR Boys Soccer | Glastonbury | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 10/1 | FR Field Hockey | Glastonbury | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 10/1 | V Girls Volleyball | Plainville | Away [Directions] | W 3-0 | 2:45 pm | |
| Mon., 10/1 | JV Girls Volleyball | Plainville | Away [Directions] | 5:00 p.m. | w/Varsity | |
| Mon., 10/1 | FR Girls Volleyball | Plainville | Away [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 10/2 | V Boys Cross Country | Southington, Hall | Away - SLOPER [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 10/2 | V Girls Cross Country | Southington, Hall | Away - SLOPER [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 10/2 | JV Girls Soccer | Glastonbury | Away - GHS Field #12 [Directions] | 3:45 p.m. | w/Freshman | |
| Tue., 10/2 | FR Girls Soccer | Glastonbury | Away - GHS Field #13 [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 10/3 | V Girls Volleyball | Glastonbury | Home - Simsbury HS [Directions] | L 0-3 | ||
| Wed., 10/3 | JV Girls Volleyball | Glastonbury | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | FR Girls Volleyball | Glastonbury | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | FR Football | Conard | Away - Conard HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 10/4 | FR Field Hockey | Southington | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | 2:50 PM shuttle to HJMS | |
| Thu., 10/4 | FR Girls Soccer | Hall | Home - Henry James MS [Directions] | 3:45 p.m. | 2:50 PM shuttle to HJMS | |
| Fri., 10/5 | V Football | Conard | Away - Conard HS Stadium [Directions] | L 28-41 | 3 busses at 5:00 pm | |
| Fri., 10/5 | V Boys Soccer | Southington | Away - Turf Field SHS [Directions] | W 1-0 | 2:20 pm | |
| Fri., 10/5 | JV Boys Soccer | Southington | Away - Soccer/Girls Lacrosse [Directions] | 3:45 p.m. | w/Varsity | |
| Fri., 10/5 | V Sideline Cheerleading | Varsity Football at Conard HS | Away - Conard HS | 7:00 p.m. | 5:00 pm | |
| Fri., 10/5 | V Field Hockey | Windsor | Away - O'Brien Stadium Turf Field [Directions] | W 0-6 | 2:20 pm | |
| Fri., 10/5 | JV Field Hockey | Windsor | Away - O'Brien Stadium Turf Field [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 10/5 | V Girls Soccer | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | L 1-2 | ||
| Fri., 10/5 | JV Girls Soccer | Southington | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | East Hartford | Home - Simsbury HS [Directions] | W 3-0 | ||
| Fri., 10/5 | JV Girls Volleyball | East Hartford | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | FR Girls Volleyball | East Hartford | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Sat., 10/6 | V Boys Cross Country | Wickham Park XC Invitational | Away - Wickham Park, Manchester CT | TBA | 10:15 am | |
| Sat., 10/6 | JV Football | Conard | Away - Conard HS [Directions] | 9:30 a.m. | 7:00 am | |
| Sat., 10/6 | V Girls Cross Country | Wickham Park XC Invitational | Away - Wickham Park, Manchester CT | TBA | 9:20 am | |
| Sun., 10/7 | V Boys Crew | NE Regional Fall Race | Away - Lake Quinsigamond, Worcester MA | TBA | 1 bus at 5:30 am; 2 buses at 9:15 am | |
| Sun., 10/7 | V Girls Crew | NE Regional Fall Race | Away - Lake Quinsigamond, Worcester MA | TBA | w/Boys | |
| Mon., 10/8 | V Girls Volleyball | IVHF/Spalding Girls VolleyHall Classic Tournament | Away - American International College, MA | Cancelled | 6:30 AM | |
| Tue., 10/9 | V Boys Cross Country | Glastonbury | Away - JB Williams Park [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 10/9 | V Boys Soccer | Middletown | Away - Middletown HS [Directions] | W 3-1 | 4:15 pm | |
| Tue., 10/9 | JV Boys Soccer | Middletown | Away - Middletown HS [Directions] | 4:00 p.m. | 2:45 pm | |
| Tue., 10/9 | V Girls Cross Country | Glastonbury | Away - JB Williams Park [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 10/9 | FR Field Hockey | Conard | Away - Conard HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 10/9 | V Girls Soccer | Bristol Central | Home - Simsbury HS - Holden Field (turf) [Directions] | W 2-0 | Senior Night | |
| Wed., 10/10 | JV Boys Soccer | Hall | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Wed., 10/10 | JV Girls Soccer | Hall | Away - Hall HS JV Soccer Field [Directions] | 3:45 p.m. | 2:20 PM | |
| Wed., 10/10 | FR Girls Soccer | Hall | Away - Eisenhower Park (right next to Hall HS) [Directions] | 3:45 p.m. | w/JV | |
| Wed., 10/10 | V Girls Volleyball | Hall | Home - Simsbury HS [Directions] | L 1-3 | ||
| Wed., 10/10 | JV Girls Volleyball | Hall | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | FR Girls Volleyball | Hall | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Thu., 10/11 | V Girls Volleyball | Southington | Away - West Gym [Directions] | L 0-3 | 2:45 pm | |
| Thu., 10/11 | JV Girls Volleyball | Southington | Away - West Gym [Directions] | 5:00 p.m. | w/Varsity | |
| Thu., 10/11 | FR Girls Volleyball | Southington | Away - East Gym [Directions] | 5:00 p.m. | w/Varsity | |
| Fri., 10/12 | V Boys Soccer | East Catholic | Home - Simsbury HS - Holden Field (turf) [Directions] | W 4-0 | Senior Night | |
| Fri., 10/12 | JV Boys Soccer | East Catholic | Home - Simsbury HS - Holden Field (turf) [Directions] | 3:45 p.m. | ||
| Fri., 10/12 | FR Boys Soccer | Canton | Away - Bowdoin Field [Directions] | 4:00 p.m. | 3:00 pm | |
| Fri., 10/12 | V Field Hockey | South Windsor | Away - SWHS Stadium Turf Field [Directions] | L 1-2 | 2:20 pm | |
| Fri., 10/12 | JV Field Hockey | South Windsor | Away - SWHS Stadium Turf Field [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 10/12 | V Girls Soccer | Enfield | Away - Enfield HS [Directions] | W 5-1 | 2:20 pm | |
| Fri., 10/12 | JV Girls Soccer | Enfield | Away - Enfield HS [Directions] | 3:45 p.m. | w/Varsity | |
| Fri., 10/12 | V Girls Volleyball | Conard | Home - Simsbury HS [Directions] | L 1-3 | ||
| Fri., 10/12 | JV Girls Volleyball | Conard | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | FR Girls Volleyball | Conard | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Sat., 10/13 | FR Girls Soccer | RHAM | Home - Simsbury HS - Holden Field (turf) [Directions] | 10:00 a.m. | ||
| Sun., 10/14 | V Boys Crew | Scrimmage | Away - Northfield Mount Hermon, Gill MA 01354 | TBA | TBA | |
| Sun., 10/14 | V Girls Crew | Scrimmage | Away - Northfield Mount Hermon, Gill MA 01354 | TBA | w/Boys | |
| Mon., 10/15 | FR Boys Soccer | Hall | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | V Field Hockey | Conard | Home - Simsbury HS - Holden Field (turf) [Directions] | L 0-3 | ||
| Mon., 10/15 | JV Field Hockey | Conard | Home - Simsbury HS - Holden Field (turf) [Directions] | 5:15 p.m. | ||
| Mon., 10/15 | V Girls Soccer | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | L 2-3 | 4:30 pm | |
| Mon., 10/15 | V Girls Volleyball | Hartford Public | Home - Simsbury HS [Directions] | W 3-1 | ||
| Mon., 10/15 | JV Girls Volleyball | Hartford Public | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | FR Girls Volleyball | Hartford Public | Home - Simsbury HS [Directions] | Cancelled | ||
| Tue., 10/16 | V Boys Cross Country | CCC Cross Country Championship | Away - Wickham Park, Manchester CT | 3:00 p.m. | 12:45 pm | |
| Tue., 10/16 | V Boys Soccer | Conard | Home - Simsbury HS - Holden Field (turf) [Directions] | L 1-2 | ||
| Tue., 10/16 | JV Boys Soccer | Conard | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Tue., 10/16 | FR Boys Soccer | Avon | Away - Fisher Meadow [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 10/16 | V Girls Cross Country | CCC Cross Country Championship | Away - Wickham Park, Manchester CT | TBA | 12:45 pm | |
| Tue., 10/16 | FR Girls Soccer | Avon | Home - Henry James MS [Directions] | 3:45 p.m. | ||
| Wed., 10/17 | V Field Hockey | Newington | Home - Simsbury HS - Holden Field (turf) [Directions] | W 4-0 | ||
| Wed., 10/17 | JV Field Hockey | Newington | Home - Simsbury HS - Holden Field (turf) [Directions] | 3:45 p.m. | ||
| Wed., 10/17 | FR Field Hockey | Glastonbury | Away - GHS Field #14 [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 10/17 | V Girls Soccer | Conard | Away - Conard HS Stadium [Directions] | W 2-1 | 4:30 pm | |
| Wed., 10/17 | JV Girls Soccer | Conard | Away - Conard HS North Field [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 10/17 | FR Girls Soccer | Southington | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Thu., 10/18 | FR Football | South Windsor | Home [Directions] | 3:45 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Hartford Public | Home - Simsbury HS - Holden Field (turf) [Directions] | W 3-0 | ||
| Thu., 10/18 | JV Boys Soccer | Hartford Public | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Thu., 10/18 | FR Boys Soccer | Manchester | Away - JV Soccer Field at Manchester HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 10/18 | FR Field Hockey | Hall | Away - Hall HS Field Hockey Practice Field [Directions] | 3:45 p.m. | 2:20 pm | |
| Fri., 10/19 | V Football | South Windsor | Home - Simsbury HS - Holden Field (turf) [Directions] | W 42-0 | ||
| Fri., 10/19 | V Sideline Cheerleading | Varsity Football vs South Windsor | Home - Simsbury HS - Holden Field (turf) [Directions] | 7:00 p.m. | ||
| Fri., 10/19 | V Girls Soccer | Bulkeley | Away - Bulkeley HS Field [Directions] | W Forfeit | 2:20 pm | |
| Fri., 10/19 | JV Girls Soccer | Wethersfield | Away - Cottone Field at WHS [Directions] | 4:00 p.m. | 2:50 pm | |
| Fri., 10/19 | V Girls Volleyball | Avon | Home - Simsbury HS [Directions] | L 1-3 | ||
| Fri., 10/19 | JV Girls Volleyball | Avon | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | FR Girls Volleyball | Avon | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Sat., 10/20 | JV Football | South Windsor | Home - Simsbury HS - Holden Field (turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | V Boys Soccer | Glastonbury | Home - Simsbury HS - Holden Field (turf) [Directions] | L 1-3 | ||
| Sat., 10/20 | JV Boys Soccer | Glastonbury | Home - Simsbury HS - Grass Field [Directions] | 1:00 p.m. | ||
| Sat., 10/20 | V Girls Soccer | Glastonbury | Away - GHS Field #4 [Directions] | L 0-3 | 9:15 am | |
| Mon., 10/22 | V Boys Soccer | Avon | Away - Fisher Meadow [Directions] | L 0-4 | 2:20 pm | |
| Mon., 10/22 | JV Boys Soccer | Avon | Away - Fisher Meadow [Directions] | 3:45 p.m. | w/Varsity | |
| Mon., 10/22 | FR Boys Soccer | Farmington | Away - Tunxis Mead Park [Directions] | 3:45 p.m. | 2:20 pm | |
| Mon., 10/22 | FR Field Hockey | Conard | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 10/22 | FR Girls Soccer | Farmington | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 10/22 | V Girls Volleyball | Farmington | Away - Farmington HS [Directions] | L 0-3 | 2:45 pm | |
| Mon., 10/22 | JV Girls Volleyball | Farmington | Away - Farmington HS [Directions] | 4:00 p.m. | w/Varsity | |
| Mon., 10/22 | FR Girls Volleyball | Farmington | Away - Farmington HS [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 10/23 | V Boys Cross Country | CCC Freshman XC Championship | Away - West Hartford Reservoir, West Hartford CT | TBA | 2:20 pm | |
| Tue., 10/23 | V Field Hockey | Glastonbury | Away - GHS Turf Field [Directions] | L 0-4 | 2:20 pm | |
| Tue., 10/23 | JV Field Hockey | Glastonbury | Away - GHS Field #14 [Directions] | 5:15 p.m. | w/Varsity | |
| Tue., 10/23 | V Girls Soccer | Avon | Away - Fisher Meadow [Directions] | W 3-1 | 2:20 pm | |
| Tue., 10/23 | JV Girls Soccer | Avon | Away - Fisher Meadow [Directions] | 3:45 p.m. | w/Varsity | |
| Wed., 10/24 | V Boys Soccer | Bulkeley | Away - Bulkeley HS Field [Directions] | T 0-0 | 2:20 pm from Henry James | Bus will leave from Henry James |
| Wed., 10/24 | JV Boys Soccer | Bulkeley | Away - Colts Park [Directions] | 3:45 p.m. | w/Varsity from Henry James | Bus will leave from Henry James |
| Wed., 10/24 | FR Boys Soccer | Granby Memorial | Away - Granby Memorial HS [Directions] | 3:45 p.m. | 2:20 pm from Henry James | Bus will leave from Henry James |
| Wed., 10/24 | FR Girls Soccer | Avon | Away - Fisher Meadow [Directions] | 3:45 p.m. | 2:20 pm from Henry James | Bus will leave from Henry James |
| Thu., 10/25 | FR Football | Enfield | Away - Enfield HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 10/25 | JV Boys Soccer | Avon | Away - Fisher Meadow [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 10/25 | FR Boys Soccer | Avon | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Thu., 10/25 | V Field Hockey | Enfield | Home - Simsbury HS - Holden Field (turf) [Directions] | L 1-4 | ||
| Thu., 10/25 | JV Field Hockey | Enfield | Home - Simsbury HS - Holden Field (turf) [Directions] | 5:15 p.m. | ||
| Thu., 10/25 | FR Field Hockey | Wethersfield | Away - Cove Park [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 10/25 | FR Girls Soccer | Farmington | Away - Tunxis Mead Park [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 10/25 | V Girls Volleyball | Glastonbury | Away - Glastonbury HS [Directions] | L 0-3 | 2:45 pm | |
| Thu., 10/25 | JV Girls Volleyball | Glastonbury | Away - Glastonbury HS [Directions] | 4:00 p.m. | w/Varsity | |
| Thu., 10/25 | FR Girls Volleyball | Glastonbury | Away - Glastonbury HS [Directions] | 4:00 p.m. | w/Varsity | |
| Fri., 10/26 | V Boys Cross Country | CIAC Class LL Cross Country Championship | Away - Wickham Park, Manchester CT | 10:20 a.m. | 7:30 am(w/Girls) | |
| Fri., 10/26 | V Football | Enfield | Away - Enfield HS [Directions] | W 36-12 | 3 busses at 4:00 pm | |
| Fri., 10/26 | V Boys Soccer | Farmington | Home - Simsbury HS [Directions] | L 0-2 | ||
| Fri., 10/26 | JV Boys Soccer | Farmington | Away - Tunxis Mead Park [Directions] | 4:00 p.m. | 2:45 PM | |
| Fri., 10/26 | V Sideline Cheerleading | Varsity Football vs Enfield HS | Away - Enfield HS | 7:00 p.m. | 5:00 pm | |
| Fri., 10/26 | V Girls Cross Country | CIAC Class L Cross Country Championship | Away - Wickham Park, Manchester CT | 9:45 a.m. | 7:30 am (w/Boys) | |
| Fri., 10/26 | V Girls Soccer | Farmington | Home - Simsbury HS - Holden Field (turf) [Directions] | L 0-3 | Pink Out Game | |
| Fri., 10/26 | JV Girls Soccer | Farmington | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Fri., 10/26 | V Girls Volleyball | Newington | Home - Simsbury HS [Directions] | L 0-3 | Senior Night | |
| Fri., 10/26 | JV Girls Volleyball | Newington | Home - Simsbury HS [Directions] | 5:00 p.m. | ||
| Fri., 10/26 | FR Girls Volleyball | Newington | Home - Simsbury HS [Directions] | 5:00 p.m. | ||
| Sat., 10/27 | JV Football | Enfield | Away - Enfield HS [Directions] | Cancelled | 7:30 am | |
| Sat., 10/27 | FR Girls Volleyball | Southington High School Freshmen Play Day | Away | 9:00 a.m. | 7:30 am | |
| Sun., 10/28 | V Boys Crew | Head of the Fish Regatta | Away - Saratoga Springs NY | TBA | 1 bus at 4:00 am and 1 bus at 7:45 am | |
| Sun., 10/28 | V Girls Crew | Head of the Fish Regatta | Away - Saratoga Springs NY | TBA | w/Boys | |
| Mon., 10/29 | V Boys Soccer | Glastonbury | Away - GHS Turf Field [Directions] | L 0-3 | 2:20 pm | |
| Mon., 10/29 | JV Boys Soccer | Glastonbury | Away - GHS Field #12 [Directions] | 3:45 p.m. | w/Varsity | |
| Mon., 10/29 | V Field Hockey | Avon | Home - Simsbury HS - Holden Field (turf) [Directions] | L 1-5 | ||
| Mon., 10/29 | JV Field Hockey | Avon | Home - Simsbury HS - Grass Field [Directions] | 3:30 p.m. | ||
| Mon., 10/29 | V Girls Soccer | Glastonbury | Home - Simsbury HS - Holden Field (turf) [Directions] | L 1-4 | ||
| Mon., 10/29 | JV Girls Soccer | Glastonbury | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Mon., 10/29 | V Girls Volleyball | CCC First Round | Away | Cancelled | ||
| Tue., 10/30 | FR Boys Soccer | Glastonbury | Away - GHS Field #13 [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 10/30 | V Field Hockey | Farmington | Home - Simsbury HS - Holden Field (turf) [Directions] | W 3-1 | ||
| Tue., 10/30 | JV Field Hockey | Farmington | Home - Simsbury HS - Holden Field (turf) [Directions] | 5:15 p.m. | ||
| Tue., 10/30 | FR Girls Soccer | Glastonbury | Home - Simsbury HS - Grass Field [Directions] | 3:45 p.m. | ||
| Tue., 10/30 | Unified Sports Soccer | Enfield | Home - Simsbury HS - Grass Field [Directions] | 3:00 p.m. | Unified Flag Football | |
| Thu., 11/1 | V Boys Cross Country | CIAC Open Cross Country Championship | Away - Wickham Park, Manchester CT | 2:00 p.m. | no bus | |
| Thu., 11/1 | FR Football | Manchester | Home [Directions] | 3:45 p.m. | ||
| Thu., 11/1 | V Boys Soccer | Suffield (Scrim.) | Away - Ted Beneski Turf Field [Directions] | W 1-0 | 2:45 pm | |
| Thu., 11/1 | V Girls Cross Country | CIAC Open Cross Country Championship | Away | 11:45 a.m. | no bus | |
| Fri., 11/2 | V Girls Soccer | Granby Memorial (Scrim.) | Away [Directions] | 4:00 p.m. | 3:00 pm | |
| Fri., 11/2 | V Girls Volleyball | Miss Porters School (Scrim.) | Away | 4:00 p.m. | 3:00 pm | |
| Sat., 11/3 | V Football | Manchester | Home - Simsbury HS - Holden Field (turf) [Directions] | W 34-13 | ||
| Sat., 11/3 | V Sideline Cheerleading | Varsity Football vs Manchester HS | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:00 p.m. | ||
| Sun., 11/4 | V Boys Crew | Farmington Regatta | Away - Farmington Boathouse | TBA | 3 buses at 12:15 pm | |
| Sun., 11/4 | V Girls Crew | Farmington Regatta | Away - Farmington Boathouse | TBA | w/Boys | |
| Mon., 11/5 | JV Football | Manchester | Away - MEMORIAL FIELD AT MHS [Directions] | 3:45 p.m. | 2:20 pm | |
| Mon., 11/5 | V Girls Soccer | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | W 1-0 | 4:15 pm | CIAC Tourney 1st Round |
| Mon., 11/5 | V Girls Volleyball | Conard | Away - Conard HS [Directions] | L 1-3 | 3:45 pm | CIAC Tourney 1st Round |
| Tue., 11/6 | V Boys Soccer | Farmington | Away - Farmington Sports Arena; Farmington CT [Directions] | L 0-2 | 3:30 pm | CIAC Tourney 1st Round |
| Wed., 11/7 | V Girls Soccer | Southington | Away - Turf Field SHS [Directions] | W 1-0 | 12:15 pm | CIAC Tournament 2nd Round |
| Thu., 11/8 | FR Football | Glastonbury | Home [Directions] | 3:45 p.m. | ||
| Thu., 11/8 | V Girls Volleyball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | ||
| Fri., 11/9 | V Football | Glastonbury | Home - Simsbury HS - Holden Field (turf) [Directions] | W 30-7 | ||
| Fri., 11/9 | V Sideline Cheerleading | Varsity Football vs Glastonbury HS | Home - Simsbury HS - Holden Field (turf) [Directions] | 7:00 p.m. | ||
| Fri., 11/9 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | W 1-0 | 12:00 pm | CIAC Quarterfinal |
| Sat., 11/10 | JV Football | Glastonbury | Home - Simsbury HS - Holden Field (turf) [Directions] | 10:00 a.m. | ||
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Derryfield Park; Manchester NH | TBA | no bus | |
| Sat., 11/10 | V Girls Volleyball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Mon., 11/12 | V Girls Soccer | Ridgefield | Away - Waterbury Municipal Stadium [Directions] | 6:30 p.m. | 4:30 pm | CIAC Semifinal |
| Tue., 11/13 | Unified Sports Soccer | Unified Soccer Tournament | Away - New Britain HS | 3:00 p.m. | 2:00 pm | |
| Wed., 11/14 | V Girls Volleyball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | ||
| Sat., 11/17 | JV Football | Avon | Away [Directions] | Cancelled | 7:30 am | |
| Sat., 11/17 | JV Football | Wethersfield | Home - Simsbury HS - Holden Field (turf) [Directions] | Cancelled | ||
| Sat., 11/17 | V Girls Volleyball | CIAC Tourney Final | Away - East Haven [Directions] | Cancelled | ||
| Sat., 11/17 | Unified Sports Soccer | New England Flag Football Championship | Away | 8:00 a.m. | 6:15 am | Unified Flag Football |
| Tue., 11/20 | V Football | Avon | Home - Simsbury HS [Directions] | W 42-6 | ||
| Tue., 11/20 | V Sideline Cheerleading | Varsity Football vs Avon HS | Home - Simsbury HS - Holden Field (turf) [Directions] | 6:00 p.m. | ||
| Fri., 11/30 | V Girls Ice Hockey | Jamboree | Home - ISCC [Directions] | 7:10 p.m. | ||
| Mon., 12/3 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown HS Gymnasium [Directions] | 4:00 p.m. | 2:20 pm | |
| Mon., 12/3 | JV Girls Ice Hockey | Westminster | Away | 5:00 p.m. | no bus | |
| Thu., 12/6 | V Boys Basketball | Bristol Eastern (Scrim.) | Away - Bristol Eastern HS [Directions] | 5:00 p.m. | 3:30 pm | |
| Thu., 12/6 | V Girls Basketball | E.O. Smith (Scrim.) | Away - E.O. Smith HS [Directions] | 6:00 p.m. | 4:00 pm | |
| Fri., 12/7 | V Boys Ice Hockey | Avon Old Farms (Scrim.) | Away | 8:30 p.m. | ||
| Fri., 12/7 | JV Girls Ice Hockey | Northwest Catholic | Home - Simsbury Farms CC [Directions] | 4:30 p.m. | ||
| Sat., 12/8 | V Boys Basketball | Rockville (Scrim.) | Home - Simsbury HS [Directions] | 10:00 a.m. | ||
| Sat., 12/8 | V Boys Ice Hockey | Westminster (Scrim.) | Away | 1:15 p.m. | no bus | |
| Sat., 12/8 | V Boys Indoor Track | Hillhouse Developmental Meet | Away - Floyd Little Athletic Center, New Haven CT | 10:00 a.m. | 1 bus @ 7:30 am | |
| Sat., 12/8 | V Wrestling | Bristol Eastern (Scrim.) | Away [Directions] | 10:00 a.m. | 8:15 am | |
| Sat., 12/8 | V Girls Basketball | Granby Memorial (Scrim.) | Away - Granby Memorial HS [Directions] | 5:30 p.m. | 4:30 pm | |
| Sat., 12/8 | JV Girls Basketball | Granby Memorial (Scrim.) | Away - Granby Memorial HS [Directions] | 5:30 p.m. | w/Varsity | |
| Sat., 12/8 | V Girls Ice Hockey | Hamden Coop | Home - ISCC [Directions] | W 5-3 | ||
| Sat., 12/8 | V Girls Indoor Track | Hillhouse Developmental Meet | Away - Floyd Little Athletic Center, New Haven, CT | 10:00 a.m. | w/Boys | |
| Mon., 12/10 | V Girls Basketball | Bristol Central | Away - Bristol Central HS [Directions] | W 42-16 | 4:00 pm | |
| Mon., 12/10 | JV Girls Basketball | Bristol Central | Away - Bristol Central HS [Directions] | 5:15 p.m. | w/Varsity | |
| Tue., 12/11 | V Boys Ice Hockey | South Windsor | Home - ISCC [Directions] | W 4-1 | ||
| Tue., 12/11 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 1-3 | 2:20 pm | |
| Wed., 12/12 | V Boys Basketball | Canton (Scrim.) | Away - Canton H.S. [Directions] | 5:00 p.m. | 4:00 pm | |
| Wed., 12/12 | JV Boys Basketball | Canton (Scrim.) | Away - Canton H.S. [Directions] | 5:00 p.m. | w/Varsity | |
| Wed., 12/12 | V Wrestling | Middletown | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 12/12 | JV Wrestling | Middletown | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 12/12 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Center, Cromwell [Directions] | W 4-1 | 5:45 pm | |
| Fri., 12/14 | V Boys Swimming and Diving | Bulkeley Relays | Away | 3:30 p.m. | 2:20 pm | |
| Fri., 12/14 | V Girls Basketball | Farmington | Home - Simsbury HS [Directions] | W 39-27 | ||
| Fri., 12/14 | JV Girls Basketball | Farmington | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | FR Girls Basketball | Farmington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Sat., 12/15 | V Boys Basketball | Newington | Home - Simsbury HS [Directions] | L 45-48 | ||
| Sat., 12/15 | JV Boys Basketball | Newington | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Sat., 12/15 | FR Boys Basketball | Newington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | W 4-3 | 1:15 pm | |
| Sat., 12/15 | V Boys Indoor Track | Hillhouse Invitational Meet | Away - Floyd Little Athletic Center, New Haven CT | 10:00 a.m. | 1 bus @ 7:30 am | |
| Sat., 12/15 | V Wrestling | Wethersfield Tournament | Away - Wethersfield HS | 9:00 a.m. | 6:30 am | |
| Sat., 12/15 | V Girls Ice Hockey | Hall/Conard | Home - ISCC [Directions] | L 0-1 | ||
| Sat., 12/15 | V Girls Indoor Track | Hillhouse Invitational Meet | Away - Floyd Little Athletic Center, New Haven, CT | 10:00 a.m. | w/Boys | |
| Tue., 12/18 | V Boys Basketball | Northwest Catholic | Away - Northwest Catholic HS [Directions] | W 57-42 | 4:00 pm | |
| Tue., 12/18 | JV Boys Basketball | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 5:15 p.m. | w/Varsity | |
| Tue., 12/18 | FR Boys Basketball | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 12/18 | V Boys Swimming and Diving | Plainville Boys Swimming | Away - Plainville HS Pool [Directions] | Simsbury 82 Plainville 92 | 2:20 pm | |
| Tue., 12/18 | V Girls Basketball | Northwest Catholic | Home - Simsbury HS [Directions] | W 54-25 | ||
| Tue., 12/18 | JV Girls Basketball | Northwest Catholic | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Tue., 12/18 | V Girls Ice Hockey | Suffield Coop | Home - ISCC [Directions] | W 4-1 | ||
| Wed., 12/19 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | L 1-4 | 6:15 pm | |
| Wed., 12/19 | JV Boys Ice Hockey | Carrano Cup | Away - Shelton | 8:00 p.m. | 5:45 pm | |
| Wed., 12/19 | V Boys Indoor Track | Glastonbury | Away [Directions] | 4:30 p.m. | 1 bus @ 3:00 pm | |
| Wed., 12/19 | V Wrestling | New Britain | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 12/19 | JV Wrestling | New Britain | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 12/19 | V Girls Indoor Track | Glastonbury | Away [Directions] | 4:30 p.m. | w/Boys | |
| Wed., 12/19 | Unified Sports Basketball | Unified Basketball Level 2-3 | Away - Enfield H.S. | 3:00 p.m. | 2:00 pm | |
| Thu., 12/20 | JV Girls Ice Hockey | Tournament Game - Opponent Not Known | Away | Cancelled | ||
| Fri., 12/21 | V Boys Basketball | Hall | Home - Simsbury HS [Directions] | W 76-57 | ||
| Fri., 12/21 | JV Boys Basketball | Hall | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Hall | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Fri., 12/21 | JV Boys Ice Hockey | Carrano Cup | Away - Shelton | Cancelled | ||
| Fri., 12/21 | V Girls Basketball | Hall | Away - Hall HS - Gym A [Directions] | W 29-27 | 4:00 pm | |
| Fri., 12/21 | JV Girls Basketball | Hall | Away - Hall HS - Gym A [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 12/21 | FR Girls Basketball | Hall | Away - Hall HS - Gym A [Directions] | 3:45 p.m. | 2:20 pm | |
| Sat., 12/22 | V Boys Ice Hockey | Northwest Catholic | Away - International Skating Center of Connecticut [Directions] | L 1-7 | no bus | |
| Sat., 12/22 | V Boys Indoor Track | Hartford Public | Away [Directions] | TBA | 1 bus @ 7:00 AM | |
| Sat., 12/22 | V Wrestling | Chaves Holiday Invitational | Home - Simsbury HS [Directions] | 9:00 a.m. | ||
| Sat., 12/22 | V Girls Basketball | Bulkeley | Away - Bulkeley HS Field House [Directions] | W 44-14 | 9:00 am | |
| Sat., 12/22 | JV Girls Basketball | Bulkeley | Away - Bulkeley HS Field House [Directions] | Cancelled | w/Varsity | |
| Sat., 12/22 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | W 8-0 | 2:45 p.m. | |
| Sat., 12/22 | JV Girls Ice Hockey | Longmeadow (MA) | Home - Simsbury Farms CC [Directions] | 12:30 p.m. | ||
| Sat., 12/22 | V Girls Indoor Track | Hartford Public | Away [Directions] | TBA | w/Boys | |
| Mon., 12/24 | JV Boys Ice Hockey | Carrano Cup | Away - Shelton | 9:00 a.m. | 7:15 am | |
| Thu., 12/27 | V Boys Basketball | E.O. Smith | Home - Simsbury HS [Directions] | W 55-36 | ||
| Thu., 12/27 | JV Boys Basketball | E.O. Smith | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Thu., 12/27 | FR Boys Basketball | E.O. Smith | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away - Floyd Little Athletic Center in New Haven, CT | Cancelled | 1 bus @ 10:00 am | |
| Thu., 12/27 | V Wrestling | Lowell Holiday Tournament | Away - Lowell HS, Lowell MA | 10:00 a.m. | TBA | |
| Thu., 12/27 | JV Wrestling | Glastonbury Tournament | Away - Glastonbury | TBA | 7:15 am | |
| Thu., 12/27 | V Girls Basketball | Sunlake (FL) | Away | W 34-14 | ||
| Thu., 12/27 | V Girls Indoor Track | Jack Long Invitational | Away - Floyd Little Athletic Center in New Haven, CT | Cancelled | w/Boys | |
| Fri., 12/28 | V Wrestling | Lowell Holiday Tournament | Away - Lowell HS, Lowell MA | 8:30 a.m. | TBA | |
| Fri., 12/28 | V Girls Basketball | Boone (FL) | Away | L 33-42 | ||
| Sat., 12/29 | V Boys Basketball | Granby Memorial | Home - Simsbury HS [Directions] | W 61-50 | ||
| Sat., 12/29 | JV Boys Basketball | Granby Memorial | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Sat., 12/29 | FR Boys Basketball | Granby Memorial | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Sat., 12/29 | V Boys Ice Hockey | Glastonbury | Away - Trinity College [Directions] | T 2-2(OT) | 6:45 pm | |
| Sat., 12/29 | JV Boys Ice Hockey | Carrano Cup | Away - Shelton | 5:15 p.m. | 3:15 pm | |
| Sat., 12/29 | V Boys Indoor Track | 3rd Wilton Wright Invitational | Away - Southern Connecticut State University, New Haven CT | 3:00 p.m. | 1 bus @ 12:30 PM | |
| Sat., 12/29 | V Girls Basketball | Bartlesville (OK) | Away | L 23-44 | ||
| Sat., 12/29 | V Girls Indoor Track | 3rd Wilton Wright Invitational | Away - Southern Connecticut State University, New Haven CT | 3:00 p.m. | w/Boys | |
| Mon., 12/31 | V Co-ed Cross Country Skiing | Nordic Ski Race - Lennox | Away - Prospect Mountain VT | 9:30 a.m. | 4:45 am | |
| Wed., 1/2 | V Boys Ice Hockey | West Haven Coop | Home - Westminster School [Directions] | L 2-3(OT) | ||
| Wed., 1/2 | V Girls Ice Hockey | Avon | Home - Simsbury Farms CC [Directions] | W 6-1 | ||
| Thu., 1/3 | V Boys Indoor Track | 5th Wintergreen Invitational | Away - Southern Connecticut State University, New Haven CT | 3:00 p.m. | 1 bus @ 12:30 pm | |
| Thu., 1/3 | V Wrestling | Hall | Away - Hall HS - Gym A [Directions] | 6:00 p.m. | 4:00 pm | |
| Thu., 1/3 | JV Wrestling | Hall | Away - Hall HS - Gym A [Directions] | 6:00 p.m. | w/Varsity | |
| Thu., 1/3 | V Girls Indoor Track | 5th Wintergreen Invitational | Away - Southern Connecticut State University, New Haven CT | 3:00 p.m. | w/Boys | |
| Fri., 1/4 | V Boys Basketball | Farmington | Home - Simsbury HS [Directions] | L 52-56(OT) | ||
| Fri., 1/4 | JV Boys Basketball | Farmington | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Fri., 1/4 | FR Boys Basketball | Farmington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Fri., 1/4 | V Girls Basketball | Farmington | Away - Farmington HS [Directions] | W 30-28 | 4:00 pm | |
| Fri., 1/4 | JV Girls Basketball | Farmington | Away - Farmington HS [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 1/4 | FR Girls Basketball | Farmington | Away - Farmington HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Fri., 1/4 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | W 6-1 | 7:00 pm | |
| Sat., 1/5 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms [Directions] | L 3-5 | 6:45 pm | |
| Sat., 1/5 | JV Boys Ice Hockey | Longmeadow (MA) | Away - Fitzpatrick Arena, Holyoke MA | 11:30 a.m. | 9:30 am | |
| Sat., 1/5 | V Boys Indoor Track | Hillhouse Relay | Away - Floyd Little Athletic Center, New Haven CT | 9:00 a.m. | 1 bus @ 6:30 am | |
| Sat., 1/5 | V Wrestling | Falcon Invitational Dual Meet | Away - Minnechaug Regional HS, 621 Main St. Wilbraham, MA | 9:30 a.m. | 7:00 am | |
| Sat., 1/5 | JV Wrestling | Falcon Invitational Dual Meet | Away - Minnechaug Regional HS, 621 Main St. Wilbraham, MA | 9:30 a.m. | w/Varsity | |
| Sat., 1/5 | V Co-ed Cross Country Skiing | Nordic Ski Race - Prospect | Away | 1:30 p.m. | 9:15 am | |
| Sat., 1/5 | V Girls Ice Hockey | Darien | Home - Simsbury Farms CC [Directions] | W 3-2 | ||
| Sat., 1/5 | JV Girls Ice Hockey | Longmeadow (MA) | Away - Fitzpatrick Arena, Holyoke MA | 2:30 p.m. | 12:30 pm | |
| Sat., 1/5 | V Girls Indoor Track | Hillhouse Relay | Away - Floyd Little Athletic Center, New Haven CT | 10:00 a.m. | w/Boys | |
| Mon., 1/7 | V Boys Basketball | Avon | Away - Avon HS [Directions] | W 60-36 | 4:00 pm | |
| Mon., 1/7 | JV Boys Basketball | Avon | Away - Avon HS [Directions] | 5:15 p.m. | w/Varsity | |
| Mon., 1/7 | FR Boys Basketball | Avon | Away - Avon HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Mon., 1/7 | JV Wrestling | Xavier, Fairfield Warde | Away - Xavier [Directions] | TBA | 2:30 pm | |
| Mon., 1/7 | V Girls Basketball | Avon | Home - Simsbury HS [Directions] | W 32-30 | ||
| Mon., 1/7 | JV Girls Basketball | Avon | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Mon., 1/7 | FR Girls Basketball | Avon | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Mon., 1/7 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | W 5-3 | 2:20 pm | |
| Mon., 1/7 | Unified Sports Basketball | Unified Basketball Level 2 | Away - Newington HS | 3:00 p.m. | 2:00 pm | |
| Tue., 1/8 | V Boys Swimming and Diving | Rocky Hill | Home - Westminster School [Directions] | Simsbury 96 Rockyhill 90 | ||
| Wed., 1/9 | V Boys Indoor Track | GHS Meet | Away - Glastonbury HS | 4:30 p.m. | 2:20 pm | |
| Wed., 1/9 | V Wrestling | Manchester | Away - MAIN GYM AT MHS [Directions] | 6:00 p.m. | 3:45 pm | |
| Wed., 1/9 | JV Wrestling | Manchester | Away [Directions] | 6:00 p.m. | w/Varsity | |
| Wed., 1/9 | V Girls Indoor Track | GHS Meet | Away - Glastonbury HS | 4:30 p.m. | w/Boys | |
| Wed., 1/9 | Unified Sports Basketball | Unified Basketball Level 2&3 v Enfield | Home - Simsbury HS [Directions] | 2:30 p.m. | ||
| Thu., 1/10 | V Boys Basketball | Windsor | Away - Windsor HS [Directions] | L 68-70 | 4:00 pm | |
| Thu., 1/10 | JV Boys Basketball | Windsor | Away - Windsor HS [Directions] | 5:15 p.m. | w/Varsity | |
| Thu., 1/10 | FR Boys Basketball | Windsor | Away - Windsor HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 1/10 | V Girls Basketball | Hartford Public | Home - Simsbury HS [Directions] | W 49-26 | ||
| Fri., 1/11 | V Boys Ice Hockey | Hamden | Home - ISCC [Directions] | W 4-3 | ||
| Fri., 1/11 | JV Boys Ice Hockey | Avon Old Farms | Away | 4:45 p.m. | no bus | |
| Fri., 1/11 | V Boys Swimming and Diving | Newington | Home - Westminster School [Directions] | Simsbury 90 Newington 94 | ||
| Sat., 1/12 | V Boys Ice Hockey | Immaculate | Home - ISCC [Directions] | L 1-5 | ||
| Sat., 1/12 | V Boys Indoor Track | Yale Track Classic | Away - Yale University | TBA | 1 bus @ 9:00 am | |
| Sat., 1/12 | V Wrestling | Cumberland Tournament | Away - Cumberland HS 2600 Mendon Road, Cumberland, RI | 9:00 a.m. | 5:30 am | |
| Sat., 1/12 | JV Wrestling | Trumbull | Away [Directions] | 9:15 a.m. | 6:15 am | |
| Sat., 1/12 | V Co-ed Cross Country Skiing | Nordic Ski Race - Amherst | Away - Prospect Mountain VT | 9:30 a.m. | 4:45 am | |
| Sat., 1/12 | V Girls Basketball | Weaver | Home - Simsbury HS [Directions] | W 45-34 | ||
| Sat., 1/12 | JV Girls Ice Hockey | Kent School | Home - Simsbury Farms CC [Directions] | Cancelled | ||
| Sat., 1/12 | V Girls Indoor Track | Yale Track Classic | Away - Yale University | TBA | w/Boys | |
| Mon., 1/14 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | L 1-2 | 6:15 pm | |
| Tue., 1/15 | V Boys Basketball | Enfield | Away - Enfield HS [Directions] | W 69-64 | 4:00 pm | |
| Tue., 1/15 | JV Boys Basketball | Enfield | Away - Enfield HS [Directions] | 5:15 p.m. | w/Varsity | |
| Tue., 1/15 | FR Boys Basketball | Enfield | Away - Enfield HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 1/15 | JV Boys Ice Hockey | Northwest Catholic | Home - Simsbury Farms CC [Directions] | 5:30 p.m. | ||
| Tue., 1/15 | V Boys Swimming and Diving | East Catholic | Home - Westminster School [Directions] | Simsbury 94 East Catholic 89 | ||
| Wed., 1/16 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton - Lower [Directions] | L 4-5(OT) | 2:20 pm | |
| Wed., 1/16 | V Wrestling | Conard | Away - Conard HS [Directions] | 6:00 p.m. | 4:00 pm | |
| Wed., 1/16 | JV Wrestling | Conard | Away [Directions] | 6:00 p.m. | w/Varsity | |
| Fri., 1/18 | V Boys Basketball | Glastonbury | Home - Simsbury HS [Directions] | W 70-62 | ||
| Fri., 1/18 | JV Boys Basketball | Glastonbury | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Fri., 1/18 | FR Boys Basketball | Glastonbury | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Fri., 1/18 | V Boys Swimming and Diving | Granby Memorial | Away - FVYMCA [Directions] | Simsbury 97 Granby 83 | 2:20 pm | |
| Fri., 1/18 | V Girls Basketball | Glastonbury | Away - Glastonbury HS [Directions] | L 36-43 | 4:00 pm | |
| Fri., 1/18 | JV Girls Basketball | Glastonbury | Away - Glastonbury HS [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 1/18 | FR Girls Basketball | Glastonbury | Away - Glastonbury HS [Directions] | 4:00 p.m. | 2:35 pm | |
| Sat., 1/19 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena - Rt 5 [Directions] | L 3-4(OT) | 1:30 pm | |
| Sat., 1/19 | V Boys Indoor Track | SCC Coaches Invitational | Away - Floyd Little Athletic Center, New Haven CT | 9:00 a.m. | 1 bus @ 6:45 am | |
| Sat., 1/19 | V Wrestling | The Colter Abely Mid-Season Classic | Away - Mercy HS | 9:00 a.m. | 6:00 am | |
| Sat., 1/19 | V Girls Ice Hockey | Daniel Hand Coop | Home - ISCC [Directions] | W 6-0 | ||
| Sat., 1/19 | JV Girls Ice Hockey | Woodstock Academy Coop | Home - Simsbury Farms CC [Directions] | 12:30 p.m. | ||
| Sat., 1/19 | V Girls Indoor Track | SCC Coaches Invitational | Away - Floyd Little Athletic Center, New Haven CT | 9:00 a.m. | w/Boys | |
| Mon., 1/21 | JV Boys Ice Hockey | Westminster | Away | 6:15 p.m. | no bus | |
| Mon., 1/21 | V Boys Indoor Track | Freshman Sophomore Meet | Away - Floyd Little Athletic Center, New Haven CT | 9:00 a.m. | 1 bus @ 6:45 am | |
| Mon., 1/21 | JV Wrestling | Bristol Eastern Duals | Away - Bristol Eastern | TBA | 7:15 am | |
| Mon., 1/21 | V Girls Basketball | Maloney | Home - Simsbury HS [Directions] | W 38-14 | ||
| Mon., 1/21 | JV Girls Basketball | Maloney | Home - Simsbury HS [Directions] | 12:30 p.m. | ||
| Mon., 1/21 | FR Girls Basketball | Maloney | Home - Simsbury HS [Directions] | 11:00 a.m. | ||
| Mon., 1/21 | V Girls Indoor Track | Freshman Sophomore Meet | Away - Floyd Little Athletic Center, New Haven CT | 9:00 a.m. | w/Boys | |
| Tue., 1/22 | V Boys Basketball | Middletown | Away - Middletown HS [Directions] | W 78-77(2OT) | 4:00 pm | |
| Tue., 1/22 | JV Boys Basketball | Middletown | Away - Middletown HS [Directions] | 5:15 p.m. | w/Varsity | |
| Tue., 1/22 | FR Boys Basketball | Middletown | Away - Middletown HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 1/22 | V Boys Swimming and Diving | Conard | Away - Cornerstone Aquatic Center [Directions] | Conard 91 Simsbury 85 | 2:20 pm | |
| Wed., 1/23 | V Boys Ice Hockey | Conard | Away - Veteran's Memorial Rink [Directions] | W 3-2(OT) | 6:00 pm | |
| Wed., 1/23 | JV Boys Ice Hockey | Avon Old Farms | Away | 4:45 p.m. | no bus | |
| Wed., 1/23 | V Wrestling | Newington | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 1/23 | JV Wrestling | Newington | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 1/23 | JV Girls Ice Hockey | Taft | Away | 5:30 p.m. | 3:15 pm | |
| Wed., 1/23 | Unified Sports Basketball | Unified Basketball Level 2 | Away - East Hartford H.S. | 3:00 p.m. | 1:45 pm | |
| Fri., 1/25 | V Boys Basketball | East Catholic | Home - Simsbury HS [Directions] | L 40-76 | ||
| Fri., 1/25 | JV Boys Basketball | East Catholic | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Boys Basketball | East Catholic | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Fri., 1/25 | V Boys Ice Hockey | East Catholic | Home - Simsbury Farms CC [Directions] | L 2-4 | ||
| Fri., 1/25 | V Boys Swimming and Diving | Farmington | Away - Farmington-Miss Porters Pool [Directions] | Farmington 96 Simsbury 82 | 5:30 pm | |
| Fri., 1/25 | V Girls Basketball | Manchester | Away - MAIN GYM AT MHS [Directions] | L 36-41 | 4:00 pm | |
| Fri., 1/25 | JV Girls Basketball | Manchester | Away - MAIN GYM AT MHS [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 1/25 | FR Girls Basketball | Manchester | Away - MAIN GYM AT MHS [Directions] | 3:45 p.m. | 2:20 pm | |
| Sat., 1/26 | V Boys Indoor Track | CCC Championships | Away - Floyd Little Athletic Center, New Haven CT | 9:00 a.m. | 1 bus @ 6:30 am | |
| Sat., 1/26 | V Wrestling | Southington Challenge | Away - Southington HS | 9:30 a.m. | 6:30 am | |
| Sat., 1/26 | JV Wrestling | Bristol Eastern Tournament | Away - Bristol Eastern | TBA | 7:15 am | |
| Sat., 1/26 | V Co-ed Cross Country Skiing | Nordic Ski Race | Away - Prospect Mountain, VT | 9:00 a.m. | 4:45 am | |
| Sat., 1/26 | V Girls Ice Hockey | Northern Lights | Home - Simsbury Farms CC [Directions] | 12:30 p.m. | ||
| Sat., 1/26 | JV Girls Ice Hockey | Loomis Chaffee School | Away | Cancelled | ||
| Sat., 1/26 | V Girls Indoor Track | CCC Championships | Away - Floyd Little Athletic Center, New Haven CT | 9:00 a.m. | w/Boys | |
| Thu., 1/31 | V Wrestling | Southington | Away - West Gym [Directions] | 6:00 p.m. | 4:00 pm | |
| Thu., 1/31 | JV Wrestling | Southington | Away [Directions] | 6:00 p.m. | w/Varsity | |
| Fri., 2/1 | V Boys Basketball | Conard | Home - Simsbury HS [Directions] | W 53-40 | ||
| Fri., 2/1 | JV Boys Basketball | Conard | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Fri., 2/1 | FR Boys Basketball | Conard | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Fri., 2/1 | JV Boys Ice Hockey | Northwest Catholic | Away - International Skating Center of Connecticut [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Conard | Away - Conard HS [Directions] | W 42-31 | 4:00 pm | |
| Fri., 2/1 | JV Girls Basketball | Conard | Away - Conard HS [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 2/1 | FR Girls Basketball | Conard | Away - Conard HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Sat., 2/2 | V Boys Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | W 70-49 | 12:15 pm | |
| Sat., 2/2 | JV Boys Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 2:30 p.m. | w/Varsity | |
| Sat., 2/2 | V Boys Ice Hockey | Northwest Catholic | Home - ISCC [Directions] | L 1-2 | ||
| Sat., 2/2 | V Wrestling | New Fairfield Duals | Away - New Fairfield HS | 9:30 a.m. | 6:00 am | |
| Sat., 2/2 | V Co-ed Cross Country Skiing | Nordic Ski Race - Mohawk/Simsbury | Away - Mohawk Trail Regional H.S., Buckland MA | 10:00 a.m. | 6:45 am | |
| Sat., 2/2 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks [Directions] | W 2-1 | 4:15 pm | |
| Sat., 2/2 | JV Girls Ice Hockey | Northwest Catholic | Home - Simsbury Farms CC [Directions] | 12:30 p.m. | ||
| Mon., 2/4 | V Boys Indoor Track | Capital Prep Meet | Away - Floyd Little Athletic Center-New Haven | 4:00 p.m. | 1:45 pm | |
| Mon., 2/4 | V Girls Ice Hockey | Greenwich | Home - Simsbury Farms CC [Directions] | L 1-5 | ||
| Mon., 2/4 | V Girls Indoor Track | Capital Prep Meet | Away - Floyd Little Athletic Center-New Haven | 4:00 p.m. | w/Boys | |
| Tue., 2/5 | V Boys Basketball | East Hartford | Away - East Hartford HS [Directions] | W 61-57 | 4:00 pm | |
| Tue., 2/5 | JV Boys Basketball | East Hartford | Away - East Hartford HS [Directions] | 5:15 p.m. | w/Varsity | |
| Tue., 2/5 | FR Boys Basketball | East Hartford | Away - East Hartford HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 2/5 | JV Boys Ice Hockey | Westfield (MA) | Home - Simsbury Farms CC [Directions] | 4:15 p.m. | ||
| Tue., 2/5 | V Boys Swimming and Diving | Hall | Away - Cornerstone Aquatics Center [Directions] | Hall 100 Simsbury 81 | 2:20 pm | |
| Tue., 2/5 | V Girls Basketball | East Catholic | Home - Simsbury HS [Directions] | L 23-35 | ||
| Tue., 2/5 | JV Girls Basketball | East Catholic | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Girls Basketball | East Catholic | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Wed., 2/6 | V Boys Basketball | Southington | Away - West Gym [Directions] | L 43-49 | 4:00 pm | |
| Wed., 2/6 | JV Boys Basketball | Southington | Away - West Gym [Directions] | 5:15 p.m. | w/Varsity | |
| Wed., 2/6 | FR Boys Basketball | Southington | Away - West Gym [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 2/6 | V Boys Ice Hockey | Conard | Home - ISCC [Directions] | W 4-2 | ||
| Wed., 2/6 | V Wrestling | Farmington | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 2/6 | JV Wrestling | Farmington | Home - Simsbury HS [Directions] | 6:00 p.m. | ||
| Wed., 2/6 | V Girls Basketball | Southington | Home - Simsbury HS [Directions] | W 56-34 | ||
| Wed., 2/6 | JV Girls Basketball | Southington | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Wed., 2/6 | FR Girls Basketball | Southington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Wed., 2/6 | JV Girls Ice Hockey | Westminster | Away | 5:00 p.m. | no bus | |
| Wed., 2/6 | Unified Sports Basketball | Unified Basketball Level 2&3 v East Hartford | Home - Simsbury HS [Directions] | 3:00 p.m. | ||
| Fri., 2/8 | V Boys Basketball | Avon | Home - Simsbury HS [Directions] | W 55-37 | ||
| Fri., 2/8 | JV Boys Basketball | Avon | Home - Simsbury HS [Directions] | 5:30 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Avon | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | JV Boys Ice Hockey | Westfield (MA) | Away - Amelia Park Westfield, MA | 7:00 p.m. | 5:30 pm | |
| Fri., 2/8 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1 bus @ 12:45 pm | |
| Fri., 2/8 | V Girls Basketball | Avon | Away - Avon HS [Directions] | W 34-17 | 4:00 pm | |
| Fri., 2/8 | JV Girls Basketball | Avon | Away - Avon HS [Directions] | 5:15 p.m. | w/Varsity | |
| Fri., 2/8 | FR Girls Basketball | Avon | Away - Avon HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Fri., 2/8 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena [Directions] | W 4-2 | 7:30 pm | |
| Fri., 2/8 | JV Girls Ice Hockey | Loomis Chaffee School | Away | 7:15 p.m. | 6:00 PM | |
| Fri., 2/8 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | w/Boys | |
| Sat., 2/9 | V Boys Ice Hockey | Ridgefield | Home - ISCC [Directions] | L 3-5 | Senior Night | |
| Sat., 2/9 | V Competitive Cheerleading | 16th Annual Windsor Warrior Challenge | Away - Windsor HS | TBA | 9:00 am | |
| Sat., 2/9 | V Co-ed Cross Country Skiing | Nordic Ski Race - Greylock/BCD/NMH | Away - Prospect Mountain, VT | 10:00 a.m. | 6:45 am | |
| Sat., 2/9 | JV Girls Ice Hockey | Kent School | Away | 2:00 p.m. | 12:00 pm | |
| Mon., 2/11 | V Boys Ice Hockey | Glastonbury | Home - Simsbury Farms CC [Directions] | W 5-1 | ||
| Mon., 2/11 | V Girls Basketball | Glastonbury | Home - Simsbury HS [Directions] | L 29-38 | Senior Night | |
| Mon., 2/11 | JV Girls Basketball | Glastonbury | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Girls Basketball | Glastonbury | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Mon., 2/11 | JV Girls Ice Hockey | Canterbury | Away | 5:00 p.m. | 3:00 pm | |
| Tue., 2/12 | JV Boys Ice Hockey | Wethersfield | Home - Simsbury Farms CC [Directions] | Cancelled | ||
| Wed., 2/13 | V Boys Basketball | Farmington | Away - Farmington HS [Directions] | L 57-68 | 4:00 pm | |
| Wed., 2/13 | JV Boys Basketball | Farmington | Away - Farmington HS [Directions] | 5:15 p.m. | w/Varsity | |
| Wed., 2/13 | FR Boys Basketball | Farmington | Away - Farmington HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 2/13 | V Boys Ice Hockey | Farmington Valley Generals | Home - ISCC [Directions] | W 6-4 | ||
| Wed., 2/13 | V Boys Swimming and Diving | Northwest Catholic | Home - Westminster School [Directions] | Northwest 82 Simsbury 90 | Senior Night | |
| Wed., 2/13 | V Girls Ice Hockey | East Catholic Coop | Home - ISCC [Directions] | W 4-3(OT) | Senior Night | |
| Wed., 2/13 | JV Girls Ice Hockey | Taft | Away | 4:45 p.m. | 3:00 pm | |
| Thu., 2/14 | V Girls Basketball | Hall | Home - Simsbury HS [Directions] | L 29-33 | ||
| Thu., 2/14 | V Girls Ice Hockey | Northwest Catholic | Home - Simsbury Farms CC [Directions] | W 4-0 | ||
| Thu., 2/14 | Unified Sports Basketball | Unified Basketball Level 3 | Away - Berlin H.S. | 3:00 p.m. | 2:00 pm | |
| Fri., 2/15 | V Boys Basketball | Berlin | Home - Simsbury HS [Directions] | W 53-47 | ||
| Fri., 2/15 | JV Boys Basketball | Berlin | Home - Simsbury HS [Directions] | 5:15 p.m. | ||
| Fri., 2/15 | FR Boys Basketball | Berlin | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Fri., 2/15 | V Boys Swimming and Diving | Southington | Away - Southington YMCA [Directions] | Southington 89 Simsbury 75 | 2:20 pm | |
| Fri., 2/15 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 4:45 p.m. | 1:00 pm | |
| Fri., 2/15 | V Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | W 4-0 | 3:00 pm | |
| Fri., 2/15 | Unified Sports Basketball | Unified Basketball Level 2 vs. Newington | Home - Simsbury HS [Directions] | 3:00 p.m. | ||
| Sat., 2/16 | V Boys Ice Hockey | East Catholic | Away - Champions Skating Center, Cromwell [Directions] | L 1-2 | 2:15 pm | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 1 bus @ 8:45 am | |
| Sat., 2/16 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 9:00 a.m. | 6:15 am | |
| Sat., 2/16 | V Competitive Cheerleading | 2019 CCC Cheerleading Championships | Away - Glastonbury HS | 5:00 p.m. | 2:15 pm | |
| Sat., 2/16 | V Co-ed Cross Country Skiing | Nordic Ski Race - Berkshire School/Hoosac | Away - Mohawk Trail Regional H.S., Buckland MA | 10:00 a.m. | 5:45 am | |
| Sat., 2/16 | V Girls Basketball | CCC Quarterfinals @ Higher Seed | Away | Cancelled | ||
| Sat., 2/16 | V Girls Ice Hockey | New Canaan | Home - ISCC [Directions] | T 1-1 | ||
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | w/Boys | |
| Mon., 2/18 | V Girls Ice Hockey | East Catholic Coop | Home - ISCC [Directions] | W 2-0 | ||
| Tue., 2/19 | V Boys Basketball | Glastonbury | Away - Glastonbury HS [Directions] | W 52-42 | 4:00 pm | |
| Tue., 2/19 | JV Boys Basketball | Glastonbury | Away - Glastonbury HS [Directions] | 5:15 p.m. | w/Varsity | |
| Tue., 2/19 | FR Boys Basketball | Glastonbury | Away - Glastonbury HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 2/19 | JV Wrestling | JV Tournament | Home - Simsbury HS [Directions] | 9:00 a.m. | ||
| Wed., 2/20 | JV Girls Ice Hockey | Kent School | Away | Cancelled | ||
| Thu., 2/21 | V Boys Basketball | East Hartford | Away - East Hartford HS [Directions] | W 63-52 | 4:15 pm | |
| Thu., 2/21 | Unified Sports Basketball | Unified Basketball Level 2 | Away - Windsor H.S. | 3:00 p.m. | 2:00 pm | |
| Fri., 2/22 | V Boys Swimming and Diving | Suffield | Away - Windsor Locks HS Pool (No Diving Board) [Directions] | 6:00 p.m. | 4:30 pm | |
| Fri., 2/22 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | TBA | Overnight, return 2/23/19 | |
| Fri., 2/22 | V Girls Ice Hockey | SCC North Final vs Conard | Away - Trinity College | 7:00 p.m. | 5:15 pm | |
| Fri., 2/22 | JV Girls Ice Hockey | East Catholic Coop | Home - Simsbury Farms CC [Directions] | 4:30 p.m. | ||
| Sat., 2/23 | V Boys Basketball | Glastonbury | Away - Bulkeley HS [Directions] | L 40-51 | 9:15 am | |
| Sat., 2/23 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | T 4-4 | 2:30 pm | |
| Sat., 2/23 | V Boys Swimming and Diving | 2019 Splash Classic | Away - Cornerstone Aquatic Center | 4:00 p.m. | 3:00 pm | |
| Sat., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | Overnight, return 2/23/19 | |
| Sat., 2/23 | V Competitive Cheerleading | NE Open Cheer & Dance Championship | Away - East Haven H.S. | 11:15 a.m. | 9:45 am | |
| Tue., 2/26 | V Boys Swimming and Diving | CCC West Diving Championship | Away - Westminster School | 7:30 p.m. | ||
| Tue., 2/26 | V Co-ed Cross Country Skiing | State Championship | Away - Notchview, Windsor MA | Cancelled | 6:30 am | |
| Tue., 2/26 | V Girls Basketball | Amity | Home - Simsbury HS [Directions] | L 33-41 | ||
| Tue., 2/26 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - ISCC [Directions] | W 3-2 | ||
| Tue., 2/26 | Unified Sports Basketball | Unified Basketball Level 2 | Away - NFA | 3:00 p.m. | 2:00 pm | |
| Wed., 2/27 | V Boys Swimming and Diving | CCC West Swimming Championship | Away - Cornerstone Aquatics Center | 3:30 p.m. | 2:20 pm | |
| Fri., 3/1 | V Boys Basketball | Scrimmage | Away | TBA | 2:30 pm | |
| Fri., 3/1 | V Wrestling | New England Championships | Away - Providence RI | TBA | TBA | Overnight, return 3/2/19 |
| Fri., 3/1 | V Girls Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | ||
| Fri., 3/1 | Unified Sports Basketball | Unified Basketball Tournament | Away - Windsor | 3:00 p.m. | 1:45 pm | |
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | Cancelled | ||
| Sat., 3/2 | V Wrestling | New England Championships | Away - Providence RI | TBA | TBA | Overnight, return 3/2/19 |
| Sat., 3/2 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | W 5-1 | 11:40 am | |
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Mon., 3/4 | V Boys Basketball | CIAC Tourney 1st Round | Away - Higher Seed | Cancelled | Simsbury BYE | |
| Tue., 3/5 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | L 1-7 | 4:00 pm | |
| Tue., 3/5 | Unified Sports Basketball | Unified Basketball Level 3 | Away - Rockville H.S. | 3:00 p.m. | 2:00 pm | |
| Wed., 3/6 | V Boys Basketball | Danbury | Away - Wilby HS, Waterbury CT [Directions] | W 68-54 | 4:45 pm | |
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Wed., 3/6 | V Competitive Cheerleading | V Boys Basketball CIAC First Round Game vs Danbury | Away - Wilby HS, Waterbury CT | 7:00 p.m. | 5:00 pm | |
| Wed., 3/6 | V Girls Ice Hockey | New Canaan | Away - Shelton Rinks [Directions] | L 1-3 | 3:15 pm | |
| Wed., 3/6 | Unified Sports Basketball | Unified Basketball Level 2 | Away - East Hartford HS | 3:30 p.m. | 2:20 pm | |
| Thu., 3/7 | V Girls Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - East Hartford HS [Directions] | 11:30 a.m. | 9:00 am | |
| Mon., 3/11 | V Boys Basketball | East Catholic | Away - Bulkeley H.S. [Directions] | L 53-77 | TBA | |
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class L Finals | Away - SCSU [Directions] | 6:30 p.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming Championship | Away - Yale University | Cancelled | ||
| Fri., 3/15 | V Boys Rugby | TBA | Home - Simsbury HS - Holden Field (turf) [Directions] | 6:00 p.m. | ||
| Thu., 3/21 | V Boys Lacrosse | East Lyme (Scrim.) | Away - ELHS Dick North Field [Directions] | 4:30 p.m. | 2:20 pm pm | |
| Thu., 3/21 | V Girls Lacrosse | Granby Memorial (Scrim.) | Away - Granby Memorial HS [Directions] | 3:30 p.m. | 2:30 pm | |
| Fri., 3/22 | V Boys Rugby | Cheshire | Away - Falcon Field, Meriden CT [Directions] | 5:30 p.m. | 3:15 pm | |
| Fri., 3/22 | V Girls Tennis | International Tennis Hall of Fame | Away - Newport RI | 10:45 a.m. | 8:30 am | |
| Sat., 3/23 | V Boys Rugby | Bishop Hendricken (RI) | Home - Simsbury HS - Holden Field (turf) [Directions] | 12:00 p.m. | ||
| Sat., 3/23 | FR Boys Rugby | Bishop Hendricken (RI) | Home - Simsbury HS - Holden Field (turf) [Directions] | 2:00 p.m. | ||
| Sat., 3/23 | V Girls Lacrosse | Berkshire School, MA | Away | 2:00 p.m. | 11:00 am | |
| Tue., 3/26 | V Baseball | Wethersfield (Scrim.) | Away - Esposito Field at WHS [Directions] | 4:00 p.m. | 2:20 pm | |
| Tue., 3/26 | V Boys Volleyball | Wethersfield (Scrim.) | Away - Wethersfield HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 3/27 | V Baseball | Granby Memorial (Scrim.) | Home - Memorial Park Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 3/27 | V Softball | Northwestern (Scrim.) | Home - Memorial Park Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | JV Softball | Northwestern (Scrim.) | Home - Memorial Park Softball Field [Directions] | 3:45 p.m. | ||
| Thu., 3/28 | V Baseball | Northwest Catholic (Scrim.) | Home - Memorial Park Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 3/28 | V Boys Lacrosse | Avon Old Farms (Scrim.) | Away | 3:45 p.m. | 2:30 pm | |
| Thu., 3/28 | V Girls Lacrosse | Ethel Walker School (Scrim.) | Away | 4:30 p.m. | ||
| Fri., 3/29 | V Wrestling | NHSCA Nationals | Away - Virginia Beach | TBA | Overnight, return 3/31/19 | |
| Sat., 3/30 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | L 4-6 | 9:30 am | |
| Sat., 3/30 | V Boys Lacrosse | New Milford | Away - New Milford HS [Directions] | W 19-3 | 8:45 am | |
| Sat., 3/30 | JV Boys Lacrosse | New Milford (Scrim.) | Away - New Milford HS [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 3/30 | V Boys Rugby | Greenwich | Away [Directions] | TBA | 2 buses @ 12:15 pm | |
| Sat., 3/30 | JV Boys Rugby | Greenwich | Away [Directions] | TBA | w/Varsity | |
| Sat., 3/30 | FR Boys Rugby | Greenwich | Away [Directions] | TBA | w/Varsity | |
| Sat., 3/30 | V Boys Volleyball | Farmington | Away - Farmington HS [Directions] | L 0-3 | 11:30 am | |
| Sat., 3/30 | JV Boys Volleyball | Farmington | Away - Farmington HS [Directions] | 1:00 p.m. | w/Varsity | |
| Sat., 3/30 | V Wrestling | NHSCA Nationals | Away - Virginia Beach | TBA | Overnight, return 3/31/19 | |
| Sat., 3/30 | V Girls Rugby | Rugby Clinic | Away - Fairfield University | TBA | 7:00 am | |
| Sun., 3/31 | V Wrestling | NHSCA Nationals | Away | TBA | Overnight, return 3/31/19 | |
| Mon., 4/1 | FR Baseball | Avon | Home - Simsbury HS [Directions] | 4:30 p.m. | ||
| Mon., 4/1 | V Softball | Enfield | Home - Memorial Park Softball Field [Directions] | L 17-1 | ||
| Mon., 4/1 | JV Softball | Enfield | Home - Memorial Park Softball Field [Directions] | W 17-10 | ||
| Tue., 4/2 | V Boys Golf | Avon | Away - Blue Fox Run [Directions] | Simsbury 164 Avon 158 | 2:00 pm | |
| Tue., 4/2 | JV Boys Golf | Avon | Away - Blue Fox Run [Directions] | 3:00 p.m. | w/Varsity | |
| Tue., 4/2 | V Boys Outdoor Track | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 3:45 p.m. | 2 buses @ 2:20 pm | |
| Tue., 4/2 | V Girls Outdoor Track | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 3:45 p.m. | 2 buses @ 2:20 pm | |
| Wed., 4/3 | V Baseball | Avon | Away - Buckingham Field [Directions] | W 16-7 | 3:15 pm | |
| Wed., 4/3 | JV Baseball | Avon | Away - Avon HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 4/3 | FR Baseball | Farmington | Home - Simsbury HS [Directions] | 4:30 p.m. | ||
| Wed., 4/3 | FR Boys Lacrosse | Hall | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | JV Boys Rugby | Darien | Away [Directions] | TBA | 2:30 pm | |
| Wed., 4/3 | V Boys Volleyball | Southington | Home - Simsbury HS [Directions] | L 0-3 | ||
| Wed., 4/3 | JV Boys Volleyball | Southington | Home - Simsbury HS [Directions] | 5:00 p.m. | ||
| Wed., 4/3 | FR Girls Lacrosse | Hall | Away - Hall HS Field Hockey Stadium [Directions] | 4:00 p.m. | 2:45 pm | |
| Wed., 4/3 | V Softball | Avon | Home - Memorial Park Softball Field [Directions] | L 4-0 | ||
| Thu., 4/4 | V Boys Golf | Northwest Catholic | Home - Simsbury Farms CC [Directions] | Simsbury 160 Northwest 164 | ||
| Thu., 4/4 | V Boys Tennis | Platt/Maloney Coop | Away - Platt high school [Directions] | L 3-4 | 2:45 pm | |
| Thu., 4/4 | V Girls Lacrosse | Northwest Catholic | Away - Northwest Catholic HS [Directions] | W 14-5 | 2:45 pm | |
| Thu., 4/4 | JV Girls Lacrosse | Northwest Catholic | Away - Northwest Catholic HS [Directions] | 5:15 p.m. | w/Varsity | |
| Thu., 4/4 | V Girls Rugby | North Haven | Away [Directions] | TBA | 3:30 pm | |
| Thu., 4/4 | V Girls Tennis | Berlin | Home - Simsbury HS [Directions] | W 4-3 | ||
| Fri., 4/5 | V Boys Lacrosse | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | L 10-13 | 4:30 pm | |
| Fri., 4/5 | JV Boys Lacrosse | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | 4:30 p.m. | 3:00 pm | |
| Fri., 4/5 | V Boys Volleyball | Lewis Mills | Home - Simsbury HS [Directions] | W 3-0 | ||
| Fri., 4/5 | JV Boys Volleyball | Lewis Mills | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Sat., 4/6 | FR Boys Rugby | Fordham Prep (NY) | Home - Simsbury HS - Holden Field (turf) [Directions] | 12:30 p.m. | ||
| Mon., 4/8 | V Girls Lacrosse | Ellington | Home - Simsbury HS - Holden Field (turf) [Directions] | W 17-5 | ||
| Mon., 4/8 | JV Girls Lacrosse | Ellington | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Tue., 4/9 | JV Baseball | Maloney | Away - Ceppa Field [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 4/9 | FR Boys Lacrosse | Southington | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | FR Girls Lacrosse | Windsor | Away - Windsor H.S. [Directions] | 4:00 p.m. | 2:45 pm | |
| Wed., 4/10 | V Baseball | Manchester | Away - MORIARTY FIELD AT MT. NEBO (SPRING ST) [Directions] | W 1-0 | 3:00 pm | |
| Wed., 4/10 | JV Baseball | Manchester | Away - KELLEY FIELD AT MANCHESTER HIGH [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 4/10 | V Boys Spring Crew | Kent Scrimmage | Away - Lake Waramaug, New Preston CT | TBA | 1 bus at 10:15 am | |
| Wed., 4/10 | V Boys Lacrosse | South Windsor | Home - Simsbury HS - Holden Field (turf) [Directions] | W 24-2 | ||
| Wed., 4/10 | JV Boys Lacrosse | South Windsor | Home - Simsbury HS - Grass Field [Directions] | Cancelled | ||
| Wed., 4/10 | V Boys Volleyball | Maloney | Home - Simsbury HS [Directions] | W 3-1 | ||
| Wed., 4/10 | JV Boys Volleyball | Maloney | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Spring Crew | Kent Scrimmage | Away - Lake Waramaug, New Preston CT | TBA | w/Boys | |
| Wed., 4/10 | V Girls Lacrosse | Southington | Away - Turf Field SHS [Directions] | W 16-8 | 2:45 pm | |
| Wed., 4/10 | JV Girls Lacrosse | Southington | Away - SubVarsity Lacrosse/Soccer [Directions] | 4:00 p.m. | w/Varsity | |
| Fri., 4/12 | V Baseball | Suffield | Home - Memorial Park Baseball Field [Directions] | W 9-5 | ||
| Fri., 4/12 | FR Boys Lacrosse | Conard | Away - Conard HS North Field [Directions] | 4:00 p.m. | 2:45 pm | |
| Fri., 4/12 | JV Boys Volleyball | New Britain | Away [Directions] | 4:00 p.m. | w/Varsity | |
| Fri., 4/12 | V Girls Lacrosse | Middletown/Coginchaug | Away - Wilson Middle 370 Hunting Hill Ave. [Directions] | W 21-1 | 3:15 pm | |
| Fri., 4/12 | V Softball | East Hartford | Home - Memorial Park Softball Field [Directions] | W 9-7 | ||
| Fri., 4/12 | JV Softball | East Hartford | Home - Memorial Park Softball Field [Directions] | W 22-7(5) | ||
| Sat., 4/13 | V Boys Spring Crew | Simsbury/Tabor Invitational | Away - Lake Quinsigamond, Worcester MA | TBA | 2 buses at 10:15 am | |
| Sat., 4/13 | V Boys Lacrosse | Hingham (MA) | Away | L 6-15 | ||
| Sat., 4/13 | V Girls Spring Crew | Simsbury/Tabor Invitational | Away - Lake Quinsigamond, Worcester MA | TBA | w/Boys | |
| Mon., 4/15 | V Boys Lacrosse | East Catholic | Home - Simsbury HS - Holden Field (turf) [Directions] | W 15-14 | ||
| Mon., 4/15 | JV Boys Lacrosse | East Catholic | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Mon., 4/15 | V Boys Volleyball | Hall | Away - Hall HS - Gym A [Directions] | W 3-1 | 2:45 pm | |
| Mon., 4/15 | JV Boys Volleyball | Hall | Away - Hall HS - Gym A [Directions] | 4:00 p.m. | w/Varsity | |
| Mon., 4/15 | FR Girls Lacrosse | Southington | Away - SubVarsity Lacrosse/Soccer [Directions] | Cancelled | ||
| Tue., 4/16 | V Baseball | Northwest Catholic | Away - Northwest Catholic HS [Directions] | W 8-2 | 2:20 pm | |
| Tue., 4/16 | JV Baseball | Northwest Catholic | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Tue., 4/16 | FR Baseball | Wethersfield | Home - Town Forest [Directions] | 4:30 p.m. | 3:45 pm | |
| Tue., 4/16 | V Boys Golf | Glastonbury | Home - Simsbury Farms CC [Directions] | Cancelled | ||
| Tue., 4/16 | V Boys Outdoor Track | Conard | Away - Conard HS Stadium [Directions] | 3:45 p.m. | 2 buses @ 2:20 pm | |
| Tue., 4/16 | V Boys Tennis | Northwest Catholic | Home - Simsbury HS [Directions] | W 6-1 [Detailed Results] | ||
| Tue., 4/16 | V Boys Volleyball | Newington | Away - Richard Rogalski Gymnasium @ Newington HS [Directions] | L 0-3 | 2:45 pm | |
| Tue., 4/16 | JV Boys Volleyball | Newington | Away - Richard Rogalski Gymnasium @ Newington HS [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 4/16 | V Girls Golf | Berlin | Away - Timberlin GC [Directions] | Berlin 231 Simsbury 246 | 1:30 pm | |
| Tue., 4/16 | V Girls Outdoor Track | Conard | Away - Conard HS Stadium [Directions] | 3:45 p.m. | 2 buses @ 2:20 pm | |
| Tue., 4/16 | V Softball | Northwest Catholic | Home - Memorial Park Softball Field [Directions] | W 7-0 | ||
| Tue., 4/16 | JV Girls Tennis | Conard | Home - Simsbury HS [Directions] | Cancelled | ||
| Wed., 4/17 | V Baseball | Hall | Home - Memorial Park Baseball Field [Directions] | L 3-5 | ||
| Wed., 4/17 | JV Baseball | Hall | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Wed., 4/17 | FR Baseball | Hall | Away - Hall HS JV Baseball Field [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 4/17 | JV Boys Rugby | Ridgefield | Away [Directions] | 5:30 p.m. | 2:45 pm | |
| Wed., 4/17 | V Boys Volleyball | Conard | Home - Simsbury HS [Directions] | L 0-3 | ||
| Wed., 4/17 | JV Boys Volleyball | Conard | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Softball | Hall | Away - Hall HS Varsity Softball Field [Directions] | W 10-7 | 2:20 pm | |
| Wed., 4/17 | JV Softball | Hall | Away - Hall HS JV Softball Field [Directions] | W 33-12 (5) | w/Varsity | |
| Wed., 4/17 | V Girls Tennis | Northwest Catholic | Away - St. Joseph's College, West Hartford [Directions] | W 5-2 | 2:45 pm | |
| Thu., 4/18 | V Boys Lacrosse | Granby Memorial | Away - Granby Memorial HS [Directions] | W 17-7 | 2:45 pm | |
| Thu., 4/18 | JV Boys Lacrosse | Granby Memorial | Away - Granby Memorial HS [Directions] | 5:30 p.m. | 4:30 pm | |
| Thu., 4/18 | V Boys Outdoor Track | Farmington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Thu., 4/18 | V Girls Outdoor Track | Farmington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Thu., 4/18 | V Girls Rugby | Midstate Rugby | Away - Cheshire CT | TBA | 2:30 pm | |
| Sat., 4/20 | V Boys Spring Crew | Exeter Invitational | Away - Lake Quinsigamond, Worcester MA | TBA | 2 buses at 12:00 pm | |
| Sat., 4/20 | V Boys Outdoor Track | Hillhouse Invite | Away | Cancelled | ||
| Sat., 4/20 | V Boys Rugby | Fairfield Prep | Home - Simsbury HS - Holden Field (turf) [Directions] | 12:00 p.m. | ||
| Sat., 4/20 | JV Boys Rugby | Fairfield Prep | Home [Directions] | 2:00 p.m. | ||
| Sat., 4/20 | FR Boys Rugby | Fairfield Prep | Home - Simsbury HS - Holden Field (turf) [Directions] | 3:30 p.m. | ||
| Sat., 4/20 | V Girls Spring Crew | Exeter Invitational | Away - Lake Quinsigamond, Worcester MA | TBA | w/Boys | |
| Sat., 4/20 | V Girls Lacrosse | Amsterdam (NY) | Away | W 17-2 | 7:00 am | |
| Sat., 4/20 | JV Girls Lacrosse | Amsterdam (NY) | Away | 2:00 p.m. | w/Varsity | |
| Sat., 4/20 | V Girls Outdoor Track | Hillhouse Invite | Away | Cancelled | ||
| Mon., 4/22 | FR Boys Lacrosse | Wethersfield | Away - Cottone Field at WHS [Directions] | 5:00 p.m. | ||
| Mon., 4/22 | V Girls Lacrosse | Middletown/Coginchaug | Home - Simsbury HS - Holden Field (turf) [Directions] | W 20-3 | ||
| Mon., 4/22 | FR Girls Lacrosse | Wethersfield | Away - Cottone Field at WHS [Directions] | 4:00 p.m. | 2:45 pm | |
| Mon., 4/22 | V Girls Tennis | Wethersfield | Away - Wethersfield HS [Directions] | W 4-3 | 2:45 pm | |
| Tue., 4/23 | JV Baseball | Rocky Hill | Home - Memorial Park Baseball Field [Directions] | 3:45 p.m. | w/Freshman | |
| Tue., 4/23 | FR Baseball | South Windsor | Away - Duprey Field - Ayers Road [Directions] | 4:00 p.m. | 2:45 pm | |
| Tue., 4/23 | JV Boys Golf | Hall | Away - Rockledge GC [Directions] | 3:00 p.m. | w/Varsity | |
| Tue., 4/23 | V Boys Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | W 12-10 | 4:05 pm | |
| Tue., 4/23 | JV Boys Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | Cancelled | 3:00 pm | |
| Tue., 4/23 | V Boys Outdoor Track | Northwest Catholic | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Manchester | Home - Simsbury HS [Directions] | L 1-6 [Detailed Results] | ||
| Tue., 4/23 | V Boys Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | W 3-0 | 2:45 pm | |
| Tue., 4/23 | JV Boys Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 4:00 p.m. | w/Varsity | |
| Tue., 4/23 | V Girls Outdoor Track | Northwest Catholic | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Softball | Wethersfield | Home - Memorial Park Softball Field [Directions] | W 9-3 | ||
| Tue., 4/23 | JV Softball | Wethersfield | Home - Memorial Park Softball Field [Directions] | W 23-2(5) | ||
| Wed., 4/24 | V Baseball | Plainville | Away - Plainville HS - Varsity Baseball Field [Directions] | L 3-5 | 4:15 pm at Memorial | |
| Wed., 4/24 | JV Baseball | Plainville | Away - Plainville HS- JV/Freshman Baseball Field [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 4/24 | FR Baseball | Plainville | Home - Town Forest [Directions] | 4:30 p.m. | 3:45 pm | |
| Wed., 4/24 | JV Boys Rugby | Southington | Home - Henry James MS [Directions] | 6:00 p.m. | ||
| Wed., 4/24 | FR Boys Rugby | Xavier | Home - Henry James MS [Directions] | 3:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Hall | Away - Hall HS Tennis Courts [Directions] | L 0-7 | 2:45 pm | |
| Wed., 4/24 | V Boys Volleyball | Newington | Home - Simsbury HS [Directions] | L 0-3 | ||
| Wed., 4/24 | JV Boys Volleyball | Newington | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Golf | Newington | Home - Simsbury Farms CC [Directions] | Newington 228 Simsbury 242 | ||
| Wed., 4/24 | V Girls Lacrosse | Avon | Home - Simsbury HS - Holden Field (turf) [Directions] | W 20-6 | ||
| Wed., 4/24 | JV Girls Lacrosse | Avon | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Wed., 4/24 | V Softball | Bristol Central | Away - Bristol Central HS [Directions] | L 12-10 | 2:20 pm | |
| Wed., 4/24 | JV Softball | Bristol Central | Away - South Side School [Directions] | L 9-13 | w/Varsity | |
| Wed., 4/24 | V Girls Tennis | Hall | Home - Simsbury HS [Directions] | W 4-3 | ||
| Thu., 4/25 | V Boys Golf | Conard | Away - Rockledge Golf Course [Directions] | Simsbury 153 Conard 166 | 2:00 pm | |
| Thu., 4/25 | JV Boys Golf | Conard | Away - Rockledge Golf Course [Directions] | 3:00 p.m. | w/Varsity | |
| Thu., 4/25 | V Boys Lacrosse | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | W 10-5 | ||
| Thu., 4/25 | JV Boys Lacrosse | Hall | Home - Simsbury HS - Grass Field [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | V Boys Tennis | East Hartford | Home - Simsbury HS [Directions] | L 1-6 [Detailed Results] | ||
| Thu., 4/25 | V Girls Golf | Northwest Catholic | Home - Simsbury Farms CC [Directions] | Northwest Catholic 213 Simsbury 235 | ||
| Thu., 4/25 | V Girls Rugby | Southington | Home - Simsbury HS [Directions] | 6:30 p.m. | ||
| Thu., 4/25 | V Softball | Maloney | Away - Dunn Sports Complex - Thorpe Ave. [Directions] | L 5-1 | 2:20 pm | |
| Thu., 4/25 | JV Softball | Maloney | Away - Dunn Sports Complex - Thorpe Ave. [Directions] | L 6-11 | w/Varsity | |
| Sat., 4/27 | V Boys Spring Crew | Quinsigamond Cup | Away - Lake Quinsigamond, Worcester MA | TBA | 2 buses at 9:15 am | |
| Sat., 4/27 | V Boys Lacrosse | Cheshire | Home - Simsbury HS - Holden Field (turf) [Directions] | W 8-5 | ||
| Sat., 4/27 | JV Boys Lacrosse | Cheshire | Home - Simsbury HS - Grass Field [Directions] | 1:00 p.m.. | ||
| Sat., 4/27 | V Boys Rugby | Aspetuck | Away - Shelton H.S. | 1:30 p.m. | 2 buses @ 11:00 am | |
| Sat., 4/27 | JV Boys Rugby | Aspetuck | Away - Shelton H.S. | 3:30 p.m. | w/Varsity | |
| Sat., 4/27 | V Girls Spring Crew | Quinsigamond CUp | Away - Lake Quinsigamond, Worcester MA | TBA | w/Boys | |
| Mon., 4/29 | V Baseball | Hartford Public | Home - Memorial Park Baseball Field [Directions] | W 10-0 | ||
| Mon., 4/29 | FR Baseball | Conard | Home - Town Forest [Directions] | 5:00 p.m. | 4:00 pm | |
| Mon., 4/29 | V Boys Golf | Farmington | Away - Farmington Country Club [Directions] | Simsbury 163 Farmington 156 | 2:00 pm | |
| Mon., 4/29 | JV Boys Golf | Farmington | Away - Tunxis Plantation CC [Directions] | 3:00 p.m. | w/Varsity | |
| Mon., 4/29 | V Boys Tennis | Bristol Central | Home - Simsbury HS [Directions] | L 1-6 [Detailed Results] | ||
| Mon., 4/29 | V Girls Golf | Hall | Away - Rockledge GC [Directions] | Hall 199 Simsbury 234 | 2:00 pm | |
| Mon., 4/29 | V Girls Lacrosse | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | W 9-8 | ||
| Mon., 4/29 | JV Girls Lacrosse | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | 5:00 p.m. | ||
| Mon., 4/29 | V Softball | Bloomfield | Away - Bloomfield HS [Directions] | W 22-0 | 2:20 pm | |
| Tue., 4/30 | FR Baseball | E.O. Smith | Away - E.O. Smith HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Tue., 4/30 | V Boys Golf | Southington | Home - Simsbury Farms CC [Directions] | Simsbury 149 Southington 161 | ||
| Tue., 4/30 | V Boys Outdoor Track | Avon | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Boys Volleyball | Southington | Away - West Gym [Directions] | L 0-3 | 2:45 pm | |
| Tue., 4/30 | JV Boys Volleyball | Southington | Away - West Gym [Directions] | 5:00 p.m. | w/Varsity | |
| Tue., 4/30 | V Girls Outdoor Track | Avon | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Baseball | Glastonbury | Home - Memorial Park Baseball Field [Directions] | L 0-3 | ||
| Wed., 5/1 | JV Baseball | Glastonbury | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | FR Baseball | Glastonbury | Away - Glastonbury HS [Directions] | 4:30 p.m. | 2:45 pm | |
| Wed., 5/1 | V Boys Lacrosse | Daniel Hand | Home - Simsbury HS - Holden Field (turf) [Directions] | W 8-7 | ||
| Wed., 5/1 | JV Boys Lacrosse | Daniel Hand | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Wed., 5/1 | V Boys Volleyball | Bulkeley | Away - Bulkeley HS Field House [Directions] | W 3-0 | 2:45 pm | |
| Wed., 5/1 | JV Boys Volleyball | Bulkeley | Away - Bulkeley HS Field House [Directions] | Cancelled | ||
| Wed., 5/1 | V Girls Golf | Farmington, Berlin | Home - Simsbury Farms CC [Directions] | Farmington 220 Berlin 229 Simsbury 239 | ||
| Wed., 5/1 | V Softball | Glastonbury | Away - Glastonbury HS [Directions] | L 19-4 | 2:20 pm | |
| Wed., 5/1 | JV Softball | Glastonbury | Away - Glastonbury HS [Directions] | W 5-1 | w/Varsity | |
| Wed., 5/1 | JV Girls Tennis | Hall | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | V Boys Golf | Avon | Home - Simsbury Farms CC [Directions] | Simsbury 154 Avon 157 | ||
| Thu., 5/2 | JV Boys Golf | Avon | Home - Simsbury Farms CC [Directions] | 3:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Middletown | Away - Middletown Tennis Courts - Newtown Street [Directions] | L 2-5 | 2:45 pm | |
| Thu., 5/2 | V Girls Golf | Conard | Away - Rockledge Golf Course [Directions] | Conard 219 Simsbury 233 | 2:00 pm | |
| Thu., 5/2 | V Softball | Canton | Home - Memorial Park Softball Field [Directions] | W 9-2 | ||
| Fri., 5/3 | V Baseball | Farmington | Away - Tunxis Mead Park [Directions] | L 3-4 | 2:20 pm | |
| Fri., 5/3 | V Boys Lacrosse | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | W 13-7 | ||
| Fri., 5/3 | JV Boys Lacrosse | Southington | Home - Simsbury HS - Grass Field [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | V Boys Outdoor Track | Middletown Outdoor Track & Field Invitational Frosh-Soph Meet | Away - Middletown H.S. | 3:30 p.m. | 1 bus @ 1:30 pm | |
| Fri., 5/3 | V Boys Outdoor Track | E.O. Smith Twilight Invite | Away - E.O. Smith H.S. | 4:30 p.m. | ||
| Fri., 5/3 | V Boys Rugby | Staples | Home - Simsbury HS - Holden Field (turf) [Directions] | 6:15 p.m. | ||
| Fri., 5/3 | JV Boys Rugby | Staples | Home - Simsbury HS - Holden Field (turf) [Directions] | 7:05 p.m. | ||
| Fri., 5/3 | V Boys Volleyball | Conard | Away - Conard HS [Directions] | L 2-3 | 3:00 pm (w/Fr Girls Lacrosse) | |
| Fri., 5/3 | JV Boys Volleyball | Conard | Away - Conard HS [Directions] | 4:00 p.m. | w/Varsity | |
| Fri., 5/3 | V Girls Golf | Avon | Home - Simsbury Farms CC [Directions] | Avon 208 Simsbury 230 | ||
| Fri., 5/3 | V Girls Lacrosse | Conard | Away - Conard HS Stadium [Directions] | L 10-17 | 2:45 pm | |
| Fri., 5/3 | JV Girls Lacrosse | Conard | Away - Conard HS Stadium [Directions] | 5:30 p.m. | w/Varsity | |
| Fri., 5/3 | FR Girls Lacrosse | Conard | Away - Conard HS North Field [Directions] | 4:00 p.m. | 3:00 pm (w/Boys Volleyball) | |
| Fri., 5/3 | V Girls Outdoor Track | Middletown Outdoor Track & Field Invitational Frosh-Soph Meet | Away - Middletown H.S | 3:30 p.m. | w/Boys | |
| Fri., 5/3 | V Softball | Farmington | Away - Tunxis Mead Park [Directions] | L 7-2 | 2:45 pm | |
| Fri., 5/3 | JV Softball | Farmington | Away - Tunxis Mead Park [Directions] | W 12-5 | w/Varsity | |
| Sat., 5/4 | V Boys Outdoor Track | Middletown Outdoor Track & Field Invitational Varsity Meet | Away - Middletown H.S. | 1:00 p.m. | 1 bus @ 10:45 am | |
| Sat., 5/4 | FR Boys Rugby | Staples | Home - Simsbury HS - Holden Field (turf) [Directions] | 11:30 a.m. | ||
| Sat., 5/4 | V Boys Tennis | Enfield/Somers/AAE Coop | Away - Enfield HS [Directions] | L 2-5 | 10:00 am | |
| Sat., 5/4 | V Girls Outdoor Track | Middletown Outdoor Track & Field Invitational Varsity Meet | Away - Middletown H.S. | 1:00 p.m. | 1 bus @ 10:45 am | |
| Sat., 5/4 | V Girls Rugby | Greenwich | Home - Simsbury HS - Holden Field (turf) [Directions] | 1:30 p.m. | ||
| Mon., 5/6 | V Baseball | Southington | Away - Baseball Varsity Field [Directions] | L 2-12 | 4:15 pm | |
| Mon., 5/6 | JV Baseball | Southington | Away - Baseball JV Field [Directions] | 3:45 p.m. | 2:20 pm | |
| Mon., 5/6 | FR Baseball | Southington | Home - Town Forest [Directions] | 4:30 p.m. | 3:45 pm | |
| Mon., 5/6 | V Boys Lacrosse | Northwest Catholic | Home - Simsbury HS - Holden Field (turf) [Directions] | W 19-3 | ||
| Mon., 5/6 | JV Boys Lacrosse | Northwest Catholic | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Glastonbury | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Southington | Home - Simsbury HS [Directions] | L 0-7 [Detailed Results] | ||
| Mon., 5/6 | V Boys Volleyball | Wolcott Tech | Home - Simsbury HS [Directions] | W 3-0 | ||
| Mon., 5/6 | JV Boys Volleyball | Wolcott Tech | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Golf | Avon | Away - Blue Fox Run [Directions] | Avon 215 Simsbury 233 | 2:00 pm | |
| Mon., 5/6 | FR Girls Lacrosse | Hall | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Southington | Home - Memorial Park Softball Field [Directions] | L 16-1 | ||
| Mon., 5/6 | JV Softball | Southington | Home - Memorial Park Softball Field [Directions] | L 28-0(6) | ||
| Mon., 5/6 | V Girls Tennis | Southington | Away - Tennis Courts [Directions] | L 3-4 | 2:45 pm | |
| Tue., 5/7 | V Boys Golf | Hall | Home - Simsbury Farms CC [Directions] | Simsbury 156 Hall 150 | ||
| Tue., 5/7 | JV Boys Golf | Hall | Home - Simsbury Farms CC [Directions] | 3:00 p.m. | ||
| Tue., 5/7 | FR Boys Lacrosse | Conard | Home - Henry James MS [Directions] | 5:00 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Southington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Boys Tennis | E.O. Smith | Away - E.O. Smith HS [Directions] | L 0-7 | 2:45 pm | |
| Tue., 5/7 | V Girls Lacrosse | Glastonbury | Away - GHS Field #12 [Directions] | L 11-9 | 2:45 pm | |
| Tue., 5/7 | V Girls Outdoor Track | Southington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | JV Girls Tennis | Conard | Home - Simsbury HS [Directions] | Cancelled | ||
| Tue., 5/7 | Unified Sports Track | Yard Goats Baseball Game | Away - Dunkin Donuts Park, Hartford CT | TBA | 8:15 am | Return to SHS at 2 pm |
| Wed., 5/8 | V Baseball | Conard | Home - Memorial Park Baseball Field [Directions] | W 8-1 | ||
| Wed., 5/8 | JV Baseball | Conard | Home - Memorial Park Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | FR Baseball | Conard | Away - Conard HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Wed., 5/8 | V Boys Tennis | Conard | Away - Conard HS [Directions] | L 1-6 | 2:45 pm | |
| Wed., 5/8 | V Boys Volleyball | Hall | Home - Simsbury HS [Directions] | W 3-0 | ||
| Wed., 5/8 | JV Boys Volleyball | Hall | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Girls Golf | Conard | Home - Simsbury Farms CC [Directions] | Simsbury 221 Conard 229 | ||
| Wed., 5/8 | V Girls Lacrosse | South Windsor | Home - Simsbury HS - Holden Field (turf) [Directions] | W 8-7 | ||
| Wed., 5/8 | JV Girls Lacrosse | South Windsor | Home - Simsbury HS - Holden Field (turf) [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | FR Girls Lacrosse | Conard | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Conard | Away - Sterling Field [Directions] | W 4-1 | 2:20 pm | |
| Wed., 5/8 | JV Softball | Conard | Away - Sterling Field [Directions] | W 9-1(6) | w/Varsity | |
| Wed., 5/8 | V Girls Tennis | Conard | Home - Simsbury HS [Directions] | W 6-1 | ||
| Thu., 5/9 | V Baseball | E.O. Smith | Home - Memorial Park Baseball Field [Directions] | W 4-0 | ||
| Thu., 5/9 | JV Baseball | E.O. Smith | Home - Simsbury HS [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | FR Baseball | Manchester | Home - Town Forest Park [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | V Boys Golf | Northwest Catholic | Away - Wampanoag Country Club, West Hartford, CT. [Directions] | Simsbury 163 NWC 165 | 2:00 pm | |
| Thu., 5/9 | V Boys Lacrosse | Conard | Away - Conard HS Stadium [Directions] | W 12-3 | 2:45 pm | |
| Thu., 5/9 | JV Boys Lacrosse | Conard | Away - Conard HS North Field [Directions] | 4:00 p.m. | 2:45 pm | |
| Thu., 5/9 | V Boys Tennis | Windsor | Away - Sage Park MS Tennis Courts [Directions] | W 4-2 | w/JV Boys Lacrosse at 2:45 pm | |
| Thu., 5/9 | V Girls Golf | Suffield | Away - Copper Hill [Directions] | Suffield 219 Simsbury 249 | 1:30 pm | |
| Thu., 5/9 | FR Girls Lacrosse | Wethersfield | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Girls Rugby | Fairfield Rugby | Home - Simsbury HS [Directions] | 6:30 p.m. | ||
| Thu., 5/9 | V Girls Tennis | South Windsor | Away - South Windsor HS [Directions] | L 1-6 | w/Boys Golf at 2:00 pm | |
| Fri., 5/10 | V Boys Golf | Avon Invitational | Away - Blue Fox Run, Avon CT | Simsbury 299 2nd place White 9-151 | ||
| Fri., 5/10 | V Boys Outdoor Track | 5th Torrington Varsity Alumni Club Track and Field Challenge | Away - Torrington H.S. | 3:45 p.m. | 1 bus @ 2:20 pm | |
| Fri., 5/10 | V Boys Volleyball | Bloomfield | Home - Simsbury HS [Directions] | L 1-3 | Senior Night | |
| Fri., 5/10 | JV Boys Volleyball | Bloomfield | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Girls Outdoor Track | 5th Torrington Varsity Alumni Club Track and Field Challenge | Away - Torrington H.S. | 3:45 p.m. | 1 bus @ 2:20 pm | |
| Fri., 5/10 | V Softball | Manchester | Away - MARTIN FIELD AT MANCHESTER HIGH [Directions] | W 12-4 | 2:20 pm | |
| Fri., 5/10 | JV Softball | Manchester | Away - Charter Oak Field [Directions] | L 17-13 | w/Varsity | |
| Sat., 5/11 | V Boys Spring Crew | Kent Invitational | Away - Lake Waramaug, New Preston CT | TBA | 2 buses at 10:15 am | |
| Sat., 5/11 | V Boys Rugby | Fairfield | Home - Simsbury HS - Holden Field (turf) [Directions] | 12:30 p.m. | Senior Game | |
| Sat., 5/11 | JV Boys Rugby | Fairfield | Home - Simsbury HS - Holden Field (turf) [Directions] | 2:00 p.m. | ||
| Sat., 5/11 | FR Boys Rugby | Harvey School (NY) | Home - Henry James MS [Directions] | TBA | ||
| Sat., 5/11 | V Girls Spring Crew | Kent Invitational | Away - Lake Waramaug, New Preston CT | TBA | w/Boys | |
| Sun., 5/12 | V Boys Spring Crew | Novice Regatta | Away - Harbor Park, Middletown CT | TBA | 1 bus at 5:30 am | |
| Sun., 5/12 | V Girls Spring Crew | Novice Regatta | Away - Harbor Park, Middletown CT | TBA | w/Boys | |
| Mon., 5/13 | V Boys Golf | Glastonbury | Home - Hop Meadow CC [Directions] | Simsbury 161 Glastonbury 167 | ||
| Mon., 5/13 | V Boys Lacrosse | Avon | Home - Simsbury HS - Holden Field (turf) [Directions] | W 16-9 | Senior Night | |
| Mon., 5/13 | JV Boys Lacrosse | Avon | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Mon., 5/13 | FR Boys Lacrosse | Avon | Away - Buckingham Field [Directions] | Cancelled | ||
| Mon., 5/13 | V Boys Volleyball | Maloney | Away - Maloney HS [Directions] | W 3-0 | 2:45 pm | |
| Mon., 5/13 | JV Boys Volleyball | Maloney | Away - Maloney HS [Directions] | 3:45 p.m. | w/Varsity | |
| Mon., 5/13 | V Girls Golf | Northwest Catholic, Canton | Away - Tunxis Country Club [Directions] | Northwest Catholic 213 Simsbury 238 Canton 242 | 1:45 pm | |
| Mon., 5/13 | V Girls Lacrosse | Canton | Away - Canton H.S. Turf [Directions] | L 7-15 | 2:30 pm | |
| Mon., 5/13 | JV Girls Lacrosse | Canton | Away - Canton H.S. Turf [Directions] | Cancelled | w/Varsity | |
| Tue., 5/14 | V Baseball | Maloney | Home - Memorial Park Baseball Field [Directions] | W 13-2 | ||
| Tue., 5/14 | V Boys Outdoor Track | Glastonbury | Home - Simsbury HS [Directions] | 3:45 p.m. | Senior Night | |
| Tue., 5/14 | V Boys Tennis | Farmington | Home - Simsbury HS [Directions] | L 0-7 | ||
| Tue., 5/14 | V Girls Golf | Suffield | Home - Simsbury Farms CC [Directions] | Simsbury 233 Suffield 257 | ||
| Tue., 5/14 | V Girls Lacrosse | South Windsor | Away - SWHS Multi-Purpose Grass Field [Directions] | W 8-7 | 2:45 pm | |
| Tue., 5/14 | JV Girls Lacrosse | South Windsor | Away - SWHS Multi-Purpose Grass Field [Directions] | 5:30 p.m. | w/Varsity | |
| Tue., 5/14 | FR Girls Lacrosse | Windsor | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Outdoor Track | Glastonbury | Home - Simsbury HS [Directions] | 3:45 p.m. | Senior Night | |
| Tue., 5/14 | V Girls Tennis | Rocky Hill | Away - Rocky Hill HS [Directions] | W 5-2 | 2:45 pm | |
| Wed., 5/15 | V Baseball | Farmington | Home - Memorial Park Baseball Field [Directions] | W 6-5 | ||
| Wed., 5/15 | JV Baseball | Farmington | Home - Simsbury HS [Directions] | 3:45 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | Wethersfield | Away - Cottone Field at WHS [Directions] | 4:00 p.m. | 2:45 pm | |
| Wed., 5/15 | V Boys Rugby | Harvey School (NY) | Home - Simsbury HS - Holden Field (turf) [Directions] | 6:00 p.m. | ||
| Wed., 5/15 | V Boys Tennis | Avon | Away - Avon MS [Directions] | L 0-7 | w/G Lacrosse at 2:20 pm | |
| Wed., 5/15 | V Girls Golf | Hall | Home - Simsbury Farms CC [Directions] | Hall 197 Simsbury 227 | ||
| Wed., 5/15 | V Girls Lacrosse | Avon | Away - Fisher Meadow [Directions] | W 16-9 | 2:20 pm | |
| Wed., 5/15 | JV Girls Lacrosse | Avon | Away - Fisher Meadow [Directions] | 5:45 p.m. | w/Varsity | |
| Wed., 5/15 | FR Girls Lacrosse | Glastonbury | Away - GHS Field #13 [Directions] | 4:00 p.m. | 2:45 pm | |
| Wed., 5/15 | V Softball | New Britain | Away - Chesley Park [Directions] | L 4-2 | 2:20 pm | |
| Wed., 5/15 | JV Softball | New Britain | Away - Chesley Park [Directions] | L 16-15 | w/Varsity | |
| Wed., 5/15 | V Girls Tennis | Avon | Home - Simsbury HS [Directions] | W 4-3 | ||
| Thu., 5/16 | V Baseball | South Windsor | Home - Memorial Park Baseball Field [Directions] | L 6-7 | ||
| Thu., 5/16 | JV Baseball | South Windsor | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | FR Baseball | Avon | Away - Avon HS [Directions] | 3:45 p.m. | 2:20 pm | |
| Thu., 5/16 | V Boys Golf | Farmington, Southington | Home - Simsbury Farms CC [Directions] | Simsbury 149 Southington 156 Farmington 158 | ||
| Thu., 5/16 | V Boys Lacrosse | Glastonbury | Away - GHS Turf Field [Directions] | L 4-8 | 4:15 pm | |
| Thu., 5/16 | JV Boys Lacrosse | Glastonbury | Away - GHS Field #11 [Directions] | 4:00 p.m. | 2:45 pm | |
| Thu., 5/16 | V Boys Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | W 3-1 | 3:45 pm | |
| Thu., 5/16 | JV Boys Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:00 p.m. | w/Varsity | |
| Thu., 5/16 | FR Girls Lacrosse | Avon | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Rugby | Semi-finals | Home - Simsbury HS - Holden Field (turf) [Directions] | 6:00 p.m. | ||
| Thu., 5/16 | V Softball | Farmington | Home - Memorial Park Baseball Field [Directions] | L 4-0 | ||
| Thu., 5/16 | JV Softball | Farmington | Home - Memorial Park Softball Field [Directions] | W 19-5(5) | ||
| Thu., 5/16 | V Girls Tennis | Farmington | Away - Farmington HS [Directions] | L 3-4 | 2:45 pm | |
| Fri., 5/17 | FR Boys Lacrosse | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 4:00 p.m. | 2:45 pm | |
| Fri., 5/17 | JV Boys Rugby | West Hartford | Away - Duffy Elementary School | 6:00 p.m. | 4:30 pm | |
| Fri., 5/17 | V Boys Volleyball | Farmington | Home - Simsbury HS [Directions] | L 2-3 | ||
| Fri., 5/17 | JV Boys Volleyball | Farmington | Home - Simsbury HS [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | V Girls Lacrosse | Farmington | Home - Simsbury HS - Holden Field (turf) [Directions] | W 13-3 | Senior Night | |
| Fri., 5/17 | JV Girls Lacrosse | Farmington | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Fri., 5/17 | V Softball | Avon | Away - Fisher Meadow [Directions] | L 2-0 | 2:20 pm | |
| Fri., 5/17 | JV Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | W 12-5 | 2:20 pm | |
| Fri., 5/17 | V Girls Tennis | Glastonbury | Away - East Hartford Tennis Club [Directions] | L 2-5 | 2:45 pm | East Hartford Tennis Club |
| Sat., 5/18 | V Baseball | Avon | Home - Memorial Park Baseball Field [Directions] | W 6-3 | Senior Night | |
| Sat., 5/18 | V Boys Lacrosse | Guilford | Home - Simsbury HS - Holden Field (turf) [Directions] | W 8-7 | ||
| Sat., 5/18 | JV Boys Lacrosse | Guilford | Home - Simsbury HS - Grass Field [Directions] | 11:00 a.m. | ||
| Sat., 5/18 | V Boys Rugby | Amoskeag | Away - Highland-Goffes Falls, Manchester NH | 12:00 p.m. | 1 bus @ 9:15 am | |
| Sat., 5/18 | FR Boys Rugby | Amoskeag | Away - Highland-Goffes Falls, Manchester NH | TBA | w/Varsity | |
| Sun., 5/19 | V Boys Spring Crew | Connecticut Public School Rowing Championships | Away - Lake Waramaug, New Preston CT | TBA | 1 bus at 5:45 am, 1 bus at 7:00 am | |
| Sun., 5/19 | V Girls Spring Crew | Connectictut Public School Rowing Championships | Away - Lake Waramaug, New Preston CT | TBA | w/Boys | |
| Mon., 5/20 | JV Baseball | Glastonbury | Away - Glastonbury HS [Directions] | 3:45 p.m. | w/Varsity | |
| Mon., 5/20 | FR Baseball | Glastonbury | Home - Town Forest [Directions] | 4:30 p.m. | 3:45 pm | |
| Mon., 5/20 | V Boys Golf | Hall | Away - Rockledge GC [Directions] | Simsbury 147 Hall 152 | 2:00 pm | |
| Mon., 5/20 | FR Boys Lacrosse | Glastonbury | Away - GHS Field #13 [Directions] | 4:00 p.m. | 2:45 pm | |
| Mon., 5/20 | V Boys Tennis | Glastonbury | Home - Simsbury HS [Directions] | L 0-6 | ||
| Mon., 5/20 | V Boys Volleyball | New Britain | Away - New Britain HS [Directions] | W 3-0 | 2:45 pm | |
| Mon., 5/20 | JV Boys Volleyball | New Britain | Away - New Britain HS [Directions] | 4:00 p.m. | w/Varsity | |
| Mon., 5/20 | V Girls Golf | Glastonbury | Home - Simsbury Farms CC [Directions] | Glastonbury 185 Simsbury 220 | ||
| Mon., 5/20 | V Girls Lacrosse | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | W 15-12 | ||
| Mon., 5/20 | JV Girls Lacrosse | Southington | Home - Simsbury HS - Holden Field (turf) [Directions] | 4:45 p.m. | ||
| Mon., 5/20 | FR Girls Lacrosse | Glastonbury | Home - Henry James MS [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Softball | Glastonbury | Home - Memorial Park Softball Field [Directions] | L 13-3 | ||
| Mon., 5/20 | JV Softball | Glastonbury | Home - Memorial Park Softball Field [Directions] | L 13-0 | ||
| Mon., 5/20 | V Girls Tennis | East Catholic | Away - Wickham Park, Manchester [Directions] | W Forfeit | 2:20 pm | |
| Tue., 5/21 | V Baseball | Rocky Hill | Away - Rocky Hill HS [Directions] | W 13-11 | 2:20 pm | |
| Tue., 5/21 | V Boys Golf | Conard | Home - Simsbury Farms CC [Directions] | Simsbury 153 Conard 168 | ||
| Tue., 5/21 | JV Boys Golf | Conard | Home - Simsbury Farms CC [Directions] | 3:00 p.m. | w/Varsity | |
| Tue., 5/21 | V Boys Outdoor Track | CCC West Division Outdoor Track and Field Championship | Away - Hall H.S. | 1:00 p.m. | 11:00 am | |
| Tue., 5/21 | JV Girls Lacrosse | Glastonbury | Away - GHS Field #12 [Directions] | 5:15 p.m. | 4:00 pm | |
| Tue., 5/21 | V Girls Outdoor Track | CCC West Division Outdoor Track and Field Championship | Away - Hall H.S. | 1:00 p.m. | 11:00 am | |
| Tue., 5/21 | V Softball | Windsor | Home - Memorial Park Softball Field [Directions] | L 4-9 | Senior Night | |
| Tue., 5/21 | JV Softball | Windsor | Home - Memorial Park Softball Field [Directions] | L 2-1(8) | ||
| Tue., 5/21 | V Girls Tennis | E.O. Smith | Away - E.O. Smith HS [Directions] | W 7-0 | 2:45 pm | |
| Wed., 5/22 | V Baseball | Glastonbury | Home - Memorial Park Baseball Field [Directions] | L 2-3(12) | ||
| Wed., 5/22 | V Baseball | New Britain | Home - Memorial Park Baseball Field [Directions] | L 2-3 | ||
| Wed., 5/22 | JV Baseball | New Britain | Home - Town Forest [Directions] | Cancelled | ||
| Wed., 5/22 | V Boys Golf | Southington | Away - Hawks Landing [Directions] | Simsbury 146 Southington 142 | 2:00 pm | |
| Wed., 5/22 | V Girls Golf | Farmington | Away - Tunxis Plantation CC [Directions] | Farmington 197 Simsbury 218 | 2:00 pm | |
| Wed., 5/22 | V Girls Tennis | RHAM | Home - Simsbury HS [Directions] | W 4-3 | ||
| Thu., 5/23 | V Boys Golf | 2019 CHAPPA Invitational Golf Tournament | Away | TBA | ||
| Thu., 5/23 | V Boys Lacrosse | Glastonbury | Away [Directions] | L 7-13 | 3:00 pm | |
| Thu., 5/23 | V Boys Rugby | Semi Finals | Away - Wilton HS | TBA | 3:15 pm | |
| Thu., 5/23 | V Girls Golf | East Catholic | Away - Minnechaug [Directions] | Simsbury 207 East Catholic 209 | 1:00 pm | |
| Thu., 5/23 | JV Girls Tennis | Hall | Away - Hall HS Tennis Courts [Directions] | 3:45 p.m. | 2:20 pm | |
| Fri., 5/24 | V Boys Spring Crew | New England Interscholastic Championship | Away - Lake Quinsigamond, Worcester MA | TBA | 2 buses at 10:30 am | Overnight |
| Fri., 5/24 | V Boys Tennis | Hamden | Away - Hall HS [Directions] | W 6-0 6-1 | ||
| Fri., 5/24 | V Girls Spring Crew | New England Interscholastic Championship | Away - Lake Quinsigamond, Worcester MA | TBA | w/Boys | Overnight |
| Fri., 5/24 | V Girls Tennis | Norwich Free Academy | Home - Simsbury HS [Directions] | W 7-0 | ||
| Sat., 5/25 | V Baseball | East Catholic (Scrim.) | Home - Memorial Park Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/25 | V Baseball | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | ||
| Sat., 5/25 | V Boys Spring Crew | New England Interscholastic Championship | Away - Lake Quinsigamond, Worcester MA | TBA | 2 buses | Return |
| Sat., 5/25 | V Boys Lacrosse | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | ||
| Sat., 5/25 | V Boys Tennis | Staples | Away - Hall HS [Directions] | L 1-6 0-6 | ||
| Sat., 5/25 | V Girls Spring Crew | New England Interscholastic Championship | Away - Lake Quinsigamond, Worcester MA | TBA | w/Boys | Return |
| Sat., 5/25 | V Girls Lacrosse | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | ||
| Sat., 5/25 | V Softball | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | ||
| Sat., 5/25 | V Girls Tennis | Darien | Away - Darien H.S. [Directions] | L 1-6 | 8:00 am | |
| Sun., 5/26 | V Boys Rugby | State Finals | Away - Ridgefield H.S. | Cancelled | ||
| Sun., 5/26 | V Girls Rugby | State Championship | Away - Ridgefield H.S. | 3:30 p.m. | 11:15 am | |
| Tue., 5/28 | V Boys Tennis | CIAC Tourney Quarterfinals | Away - Wesleyan University [Directions] | Cancelled | ||
| Tue., 5/28 | JV Girls Golf | Avon | Away - Blue Fox Run [Directions] | Cancelled | 2:00 pm | |
| Tue., 5/28 | V Girls Lacrosse | Hall | Home - Simsbury HS - Holden Field (turf) [Directions] | L 6-10 | ||
| Tue., 5/28 | V Girls Tennis | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Wed., 5/29 | V Baseball | East Hartford | Away - Higher Seed [Directions] | W 5-2 | 1:15 pm | |
| Wed., 5/29 | V Boys Spring Crew | Novice Regatta | Away - Farmington Boathouse, Farmington CT | TBA | 2:20 PM | |
| Wed., 5/29 | V Boys Lacrosse | Fairfield Ludlowe | Home - Simsbury HS - Holden Field (turf) [Directions] | L 7-18 | ||
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Semifinals | Away - Wesleyan University [Directions] | Cancelled | ||
| Wed., 5/29 | V Boys Volleyball | Farmington | Away - Farmington HS [Directions] | L 1-3 | 4:15 pm | |
| Wed., 5/29 | V Girls Spring Crew | Novice Regatta | Away - Farmington Boathouse | TBA | w/Boys | |
| Wed., 5/29 | V Girls Golf | CCC Tournament | Away - Tunxis Plantation | 8:00 a.m. | 7:30 am | |
| Wed., 5/29 | V Softball | E.O. Smith | Away [Directions] | L 1-6 | 1:15 pm | |
| Wed., 5/29 | V Girls Tennis | CIAC Tourney Semifinals | Away - Higher Seed | Cancelled | ||
| Thu., 5/30 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | L 2-8 | 12:30 pm | |
| Thu., 5/30 | V Boys Golf | CCC Boys Golf Tournament | Away - Stanley Golf Course | 9:00 a.m. | ||
| Thu., 5/30 | V Boys Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 3:00 p.m. | 1 bus @ 11:30 am | |
| Thu., 5/30 | V Boys Tennis | CIAC Tourney Finals | Away - Wesleyan University [Directions] | Cancelled | ||
| Thu., 5/30 | JV Girls Golf | Avon | Home - Simsbury Farms CC [Directions] | Cancelled | ||
| Thu., 5/30 | V Girls Lacrosse | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Thu., 5/30 | V Girls Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 3:00 p.m. | w/Boys | |
| Thu., 5/30 | V Softball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | ||
| Thu., 5/30 | V Girls Tennis | CIAC Tourney Final | Away - Site TBA | Cancelled | ||
| Fri., 5/31 | V Boys Volleyball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Fri., 5/31 | V Softball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Sat., 6/1 | V Baseball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Sat., 6/1 | V Boys Lacrosse | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | ||
| Sat., 6/1 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Wesleyan [Directions] | Cancelled | ||
| Sat., 6/1 | V Girls Tennis | State Open Qualifying, 1st and 2nd Rounds | Away - Singles @ Conard/Doubles @ Hall | Cancelled | ||
| Mon., 6/3 | V Boys Golf | CIAC Div. I Championship | Away - Timberlin GC - Kensington [Directions] | 8:00 a.m. | ||
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | 1 bus @ 11:15 am | |
| Mon., 6/3 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Wesleyan University [Directions] | Cancelled | ||
| Mon., 6/3 | V Girls Lacrosse | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | ||
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | w/Boys | |
| Mon., 6/3 | V Girls Tennis | State Open Round of 16/Quarterfinals | Away - Yale University [Directions] | Cancelled | ||
| Tue., 6/4 | V Baseball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | ||
| Tue., 6/4 | V Boys Tennis | State Open Singles Semifinals | Away - Wesleyan University [Directions] | Cancelled | ||
| Tue., 6/4 | V Boys Volleyball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | ||
| Tue., 6/4 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | ||
| Tue., 6/4 | V Softball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | ||
| Tue., 6/4 | V Girls Tennis | State Open Semifinals | Away - Yale University [Directions] | Cancelled | ||
| Wed., 6/5 | V Boys Lacrosse | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | ||
| Wed., 6/5 | V Boys Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | Cancelled | ||
| Wed., 6/5 | V Girls Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | Cancelled | ||
| Thu., 6/6 | V Boys Volleyball | CIAC Tourney Final | Away - Site TBA | Cancelled | ||
| Sat., 6/8 | V Baseball | CIAC Tourney Final | Away - Palmer Field, Middletown [Directions] | Cancelled | ||
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Boys Lacrosse | CIAC Tourney Final | Away - Brien McMahon HS [Directions] | Cancelled | ||
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | June 7 at 2:30 pm | Overnight |
| Sat., 6/8 | V Girls Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Girls Lacrosse | CIAC Tourney Final | Away - Site TBA | Cancelled | ||
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | w/Boys; June 7 at 2:30 pm | Overnight |
| Sat., 6/8 | V Softball | CIAC Tourney Final | Away - Site TBA | Cancelled | ||
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | Cancelled | ||
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | Cancelled | ||
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | Cancelled | ||
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | Cancelled | ||
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||
| Wed., 6/19 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||