| Haddam-Killingworth 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 630 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | V Baseball | Shepaug Valley (Scrim.) | Home - Haddam Killingworth HS [Directions] | TBA | ||
| TBA | JV Baseball | Coventry | Home - Coventry [Directions] | 10:30 a.m. | ||
| TBA | JV Baseball | Morgan | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| TBA | JV Baseball | Coginchaug | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| TBA | FR Boys Basketball | Portland | Away - Portland HS [Directions] | Cancelled | Yes | |
| TBA | FR Boys Basketball | East Hampton | Home - Haddam Killingworth HS [Directions] | TBA | ||
| TBA | V Boys Lacrosse | Rocky Hill (Scrim.) | Away - Rocky Hill HS [Directions] | TBA | 10:30am | |
| TBA | JV Boys Lacrosse | Valley Regional | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Lacrosse | Old Saybrook | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| TBA | JV Boys Soccer | Hale Ray | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Valley Regional | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Old Saybrook | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Westbrook | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Portland | Home - Haddam Killingworth HS [Directions] | TBA | ||
| TBA | V Wrestling | Killingly | Away [Directions] | TBA | 3:45pm | |
| TBA | FR Field Hockey | Daniel Hand | Away - Polson Front Field/DHHS Campus [Directions] | Cancelled | yes | |
| TBA | V Girls Lacrosse | Northwest Catholic (Scrim.) | Away - Northwest Catholic HS [Directions] | TBA | 2:30pm | |
| TBA | JV Girls Soccer | East Hampton | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Soccer | North Branford/Hale Ray | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Soccer | Valley Regional | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | Non-conference | |
| TBA | JV Girls Soccer | Westbrook | Home - Haddam Killingworth HS [Directions] | Cancelled | Non-conference | |
| TBA | JV Girls Soccer | Cromwell | Away - Cromwell HS [Directions] | TBA | ||
| Wed., 8/22 | V Football | Ellington (Scrim.) | Home - Haddam Killingworth HS [Directions] | 5:00 p.m. | ||
| Sat., 8/25 | V Football | Canton (Scrim.) | Away - Canton [Directions] | 10:00 a.m. | 8:30am | |
| Thu., 8/30 | V Girls Volleyball | Avon (Scrim.) | Away - Avon HS [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 9/1 | V Football | Windham (Scrim.) | Home - Haddam Killingworth HS [Directions] | 10:00 a.m. | ||
| Sat., 9/1 | V Girls Soccer | Wilbur Cross (Scrim.) | Home - Haddam Killingworth HS [Directions] | 10:00 a.m. | ||
| Sat., 9/1 | V Girls Volleyball | East Haven (Scrim.) | Away - East Haven [Directions] | 8:30 a.m. | 7:45am | |
| Wed., 9/5 | V Boys Soccer | Daniel Hand (Scrim.) | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Wed., 9/5 | V Field Hockey | Northwest Catholic (Scrim.) | Away - St. Thomas Seminary, Bloomfield [Directions] | 3:45 p.m. | 2:30pm | |
| Wed., 9/5 | V Girls Swimming and Diving | Suffield Relays | Away - Suffield HS | 4:00 p.m. | 2:30PM | |
| Wed., 9/5 | V Girls Volleyball | Mercy (Scrim.) | Home - Mercy [Directions] | 4:00 p.m. | ||
| Thu., 9/6 | V Girls Volleyball | East Hampton | Home - Haddam-Killingworth HS [Directions] | L 2-3 | 2:30pm | |
| Thu., 9/6 | JV Girls Volleyball | East Hampton | Home - Haddam-Killingworth HS [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 9/7 | V Football | SMSA Coop | Away - Annie Fisher - Turf field Mark Twain Dr. [Directions] | W 35-8 | 4:00PM | |
| Sat., 9/8 | V Boys Cross Country | Somers Big Red Inv. | Away - Somers, NY | 8:30 a.m. | 6:05AM | |
| Sat., 9/8 | JV Football | SMSA Coop | Home - Haddam Killingworth HS [Directions] | W 14-6 | ||
| Sat., 9/8 | V Girls Cross Country | Somers Big Red Inv. | Away - Somers, NY | 8:30 a.m. | 6:05am | |
| Sat., 9/8 | V Girls Soccer | Weston | Away - WHS Turf Field [Directions] | L 0-6 | 2:30pm | |
| Sat., 9/8 | JV Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 4:00 p.m. | 2:30PM | |
| Sat., 9/8 | V Girls Volleyball | 21 South Bradley Road - Woodbridge, CT | Away - Connecticut Sports Center | 9:00 a.m. | TBA | |
| Tue., 9/11 | V Girls Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | W 3-0 | 2:30pm | Non-conference |
| Tue., 9/11 | V Girls Swimming and Diving | Suffield | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Volleyball | Hale Ray | Home - Haddam Killingworth HS [Directions] | W 3-1 | ||
| Tue., 9/11 | JV Girls Volleyball | Hale Ray | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS [Directions] | L 1-2 | 2:30pm | |
| Thu., 9/13 | V Boys Soccer | North Branford | Away - North Branford HS [Directions] | W 8-0 | ||
| Thu., 9/13 | V Girls Volleyball | Morgan | Away - Morgan HS [Directions] | W 3-0 | 2:30pm | |
| Thu., 9/13 | JV Girls Volleyball | Morgan | Away - Morgan HS [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 9/14 | V Boys Soccer | Portland | Away - Portland HS [Directions] | L 0-1 | 2:30pm | |
| Fri., 9/14 | V Field Hockey | Morgan | Away - Indian River Complex [Directions] | L 3-2 | ||
| Fri., 9/14 | JV Field Hockey | Morgan | Away - Indian River Complex [Directions] | 5:15 p.m. | ||
| Fri., 9/14 | V Girls Soccer | Portland | Home - Haddam Killingworth HS [Directions] | L 0-3 | ||
| Sat., 9/15 | V Boys Cross Country | Suffern Inv. (Varsity) | Away - Bear Mountain, NY | 10:30 a.m. | 6:30am | |
| Sat., 9/15 | V Boys Cross Country | CT River Valley Inv. (JV) | Away - Cromwell | 10:30 a.m. | 7:30am | |
| Sat., 9/15 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Haddam Killingworth HS [Directions] | W 30-6 | ||
| Sat., 9/15 | V Girls Cross Country | Suffern Inv. (Varsity) | Away - Bear Mountain, NY | 10:30 a.m. | 6:30AM | |
| Sat., 9/15 | V Girls Cross Country | CT River Inv. (JV) | Away - Cromwell HS | 10:30 a.m. | 7:30am | |
| Sat., 9/15 | V Girls Volleyball | Daniel Hand | Home - Haddam Killingworth HS [Directions] | W 3-0 | ||
| Sat., 9/15 | JV Girls Volleyball | Daniel Hand | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Haddam Killingworth HS [Directions] | L 12-22 | 9:00am | |
| Mon., 9/17 | V Boys Soccer | Valley Regional | Away - VRHS Football Field [Directions] | T 1-1 | 2:30pm | |
| Mon., 9/17 | V Field Hockey | Canton | Home - Haddam Killingworth HS [Directions] | L 4-1 | ||
| Mon., 9/17 | JV Field Hockey | Canton | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | JV Girls Soccer | Portland | Away - Portland HS [Directions] | 3:45 p.m. | 2:30PM | |
| Mon., 9/17 | V Girls Volleyball | Coginchaug | Home - Haddam Killingworth HS [Directions] | L 3-1 | ||
| Mon., 9/17 | JV Girls Volleyball | Coginchaug | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Field Hockey | Lyman Hall | Home - Haddam Killingworth HS [Directions] | T 1-1 | ||
| Thu., 9/20 | JV Field Hockey | Lyman Hall | Home - Haddam Killingworth HS [Directions] | 5:15 p.m. | ||
| Thu., 9/20 | V Girls Soccer | Valley Regional | Home - Haddam Killingworth HS [Directions] | T 2-2 | ||
| Thu., 9/20 | V Girls Volleyball | Cromwell | Home - Haddam Killingworth HS [Directions] | W 3-1 | ||
| Thu., 9/20 | JV Girls Volleyball | Cromwell | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | Yes | |
| Fri., 9/21 | V Football | MSW | Home - Haddam Killingworth HS [Directions] | W 37-22 | ||
| Fri., 9/21 | V Boys Soccer | Coginchaug | Home - Haddam Killingworth HS [Directions] | W 1-0 | ||
| Fri., 9/21 | V Field Hockey | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 7-1 | 2:30pm | |
| Fri., 9/21 | JV Field Hockey | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 9/21 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | 2:30pm | |
| Sat., 9/22 | V Boys Cross Country | Ocean State Inv. | Away - Warwick, RI | 9:00 a.m. | 6:05AM | |
| Sat., 9/22 | JV Football | MSW | Away - Peters Complex [Directions] | 10:30 a.m. | ||
| Sat., 9/22 | JV Boys Soccer | Coginchaug | Away - Field #3 - Game Field (Grass) [Directions] | 11:00 a.m. | 9:00am | |
| Sat., 9/22 | V Girls Cross Country | Ocean State Inv. | Away | 9:00 a.m. | 6:05am | |
| Sat., 9/22 | V Girls Soccer | Coginchaug | Away - Field #2 - Middle Field @ CRHS [Directions] | T 3-3 | 9:30AM | |
| Sat., 9/22 | JV Girls Soccer | Coginchaug | Away - Field #2 - Middle Field @ CRHS [Directions] | 12:30 p.m. | ||
| Mon., 9/24 | V Boys Soccer | East Hampton | Home - Haddam Killingworth HS [Directions] | W 2-0 | ||
| Mon., 9/24 | V Girls Swimming and Diving | Suffield | Away - Windsor Locks HS Pool (No Diving Board) [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 9/24 | V Girls Volleyball | Old Lyme | Away - Old Lyme HS [Directions] | W 3-0 | 2:30pm | |
| Mon., 9/24 | JV Girls Volleyball | Old Lyme | Away - Old Lyme HS [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 9/26 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | T 0-0 | 2:30pm | Non-conference |
| Wed., 9/26 | V Girls Volleyball | North Branford | Away - North Branford HS [Directions] | W 3-0 | 2:30pm | |
| Wed., 9/26 | JV Girls Volleyball | North Branford | Away - North Branford HS [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 9/27 | V Boys Cross Country | League Meet 1 | Away - Indian River | 3:45 p.m. | 2:30pm | |
| Thu., 9/27 | V Girls Cross Country | League Meet 1 | Away - Indian River | 3:45 p.m. | 2:30pm | |
| Thu., 9/27 | JV Girls Soccer | Old Saybrook | Home - Old Saybrook HS [Directions] | 3:45 p.m. | Non-conference | |
| Fri., 9/28 | V Girls Volleyball | Valley Regional | Home - Haddam Killingworth HS [Directions] | W 3-0 | ||
| Fri., 9/28 | JV Girls Volleyball | Valley Regional | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Sat., 9/29 | V Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | L 19-47 | 10:30am | |
| Sat., 9/29 | V Boys Soccer | Lyman Memorial | Home - Old Saybrook HS [Directions] | T 3-3 | 8:00am | |
| Sat., 9/29 | V Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS [Directions] | L 4-0 | 11:30am | |
| Sat., 9/29 | JV Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS [Directions] | 2:30 p.m. | ||
| Mon., 10/1 | JV Football | Cromwell/Portland | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Mon., 10/1 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 0-2 | 2:30pm | |
| Mon., 10/1 | V Field Hockey | Pomperaug | Home - Haddam Killingworth HS [Directions] | T 1-1 | ||
| Mon., 10/1 | JV Field Hockey | Pomperaug | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Mon., 10/1 | V Girls Soccer | Old Saybrook | Home - Haddam Killingworth HS [Directions] | W 2-1 | ||
| Mon., 10/1 | V Girls Volleyball | SMSA | Home - Haddam Killingworth HS [Directions] | L 3-2 | ||
| Mon., 10/1 | JV Girls Volleyball | SMSA | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Boys Cross Country | Floyd Parness Inv. | Away - Totoket Park- North Branford | 3:45 p.m. | 2:30pm | |
| Tue., 10/2 | V Girls Cross Country | Floyd Parness Inv. | Away - Totokot Park- North Branford | 3:45 p.m. | 2:30pm | |
| Tue., 10/2 | JV Girls Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | 2:30pm | |
| Tue., 10/2 | V Girls Swimming and Diving | Middletown | Away - Middletown HS [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 10/3 | V Boys Soccer | Amistad | Away - AF Amistad HS [Directions] | W 4-2 | 2:30pm | |
| Wed., 10/3 | V Field Hockey | Morgan | Away - Indian River Complex [Directions] | L 0-2 | 4:00pm | |
| Wed., 10/3 | JV Field Hockey | Morgan | Away - Indian River Complex [Directions] | 5:00 p.m. | ||
| Thu., 10/4 | V Girls Soccer | Morgan | Away - Indian River Complex [Directions] | L 0-3 | 5:00PM | |
| Thu., 10/4 | V Girls Volleyball | Hale Ray | Away - Hale-Ray HS [Directions] | W 3-2 | 2:30pm | |
| Thu., 10/4 | JV Girls Volleyball | Hale Ray | Away [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/5 | V Football | Coventry/Windham Tech/Bolton/Lyman | Home - Haddam Killingworth HS [Directions] | W 56-13 | ||
| Fri., 10/5 | V Boys Soccer | Morgan | Home - Haddam Killingworth HS [Directions] | L 1-5 | ||
| Fri., 10/5 | JV Girls Soccer | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | ||
| Fri., 10/5 | V Girls Swimming and Diving | Sheehan | Away - Sheehan HS Pool [Directions] | 5:00 p.m. | 3:15pm | |
| Sat., 10/6 | V Boys Cross Country | Woods Trail Run | Away - Thetford, VT | 11:00 a.m. | 6:00am | |
| Sat., 10/6 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS [Directions] | 10:00 a.m. | 8:00am | |
| Sat., 10/6 | JV Boys Soccer | Morgan | Away - Morgan HS [Directions] | 10:30 a.m. | 9:15am | |
| Sat., 10/6 | V Girls Cross Country | Woods Trail Run | Away - Thetford, VT | 11:00 a.m. | 6:00AM | |
| Sat., 10/6 | V Field Hockey | Stonington | Away - Palmer Field (Turf) [Directions] | L 0-6 | 3:00pm | |
| Sat., 10/6 | JV Field Hockey | Stonington | Away - Palmer Field (Turf) [Directions] | 4:30 p.m. | 3:00pm | |
| Sat., 10/6 | V Girls Soccer | Cromwell | Home - Haddam Killingworth HS [Directions] | L 0-3 | ||
| Mon., 10/8 | V Girls Soccer | Westbrook | Home - Haddam Killingworth HS [Directions] | W 4-0 | ||
| Tue., 10/9 | V Boys Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | W 8-0 | 2:30pm | |
| Tue., 10/9 | V Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | L 4-0 | 2:30pm | |
| Tue., 10/9 | JV Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Tue., 10/9 | V Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | L 0-3 | 2:30pm | |
| Tue., 10/9 | JV Girls Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | 2:30pm | |
| Tue., 10/9 | V Girls Swimming and Diving | Old Lyme/Valley Reg/Old Saybrook | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Volleyball | Morgan | Home - Haddam Killingworth HS [Directions] | W 3-0 | ||
| Tue., 10/9 | JV Girls Volleyball | Morgan | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Boys Cross Country | League Meet 2 | Away - Nathan Hale Ray HS | 3:00 p.m. | 1:00pm | |
| Wed., 10/10 | V Girls Cross Country | League Meet 2 | Away - Nathan Hale Ray HS | 3:00 p.m. | 1:00pm | |
| Wed., 10/10 | V Girls Volleyball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | L 3-1 | 2:30pm | |
| Wed., 10/10 | JV Girls Volleyball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/12 | V Football | MSW | Away - Peters Complex [Directions] | W 63-22 | 5:00pm | |
| Sat., 10/13 | JV Boys Soccer | Cromwell | Home - Old Saybrook HS [Directions] | 12:00 p.m. | ||
| Sat., 10/13 | V Field Hockey | North Branford | Home - Old Saybrook HS [Directions] | L 5-0 | 4:00pm | |
| Sat., 10/13 | JV Field Hockey | North Branford | Home - Old Saybrook HS [Directions] | 10:30 a.m. | ||
| Sat., 10/13 | V Girls Volleyball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | W 3-0 | 2:30pm | |
| Sat., 10/13 | JV Girls Volleyball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 4:00 p.m. | 2:30pm | |
| Sun., 10/14 | V Boys Soccer | Hale Ray | Away - Hale Ray MS Field [Directions] | W 3-1 | 5:00pm | |
| Mon., 10/15 | JV Football | MSW | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Mon., 10/15 | FR Field Hockey | Daniel Hand | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Mon., 10/15 | V Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | L 0-6 | 2:30pm | |
| Mon., 10/15 | V Girls Volleyball | Old Lyme | Home - Haddam Killingworth HS [Directions] | W 3-0 | ||
| Mon., 10/15 | JV Girls Volleyball | Old Lyme | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Boys Soccer | Old Lyme | Home - Haddam Killingworth HS [Directions] | W 4-2 | ||
| Tue., 10/16 | V Field Hockey | Old Saybrook | Home - Haddam Killingworth HS [Directions] | L 6-1 | ||
| Tue., 10/16 | JV Field Hockey | Old Saybrook | Home - Haddam Killingworth HS [Directions] | 5:15 p.m. | ||
| Tue., 10/16 | V Girls Soccer | Valley Regional | Away - VRHS Football Field [Directions] | L 0-1 | 9:45am | Non-conference |
| Tue., 10/16 | V Girls Volleyball | North Branford | Home - Haddam Killingworth HS [Directions] | W 3-0 | ||
| Tue., 10/16 | JV Girls Volleyball | North Branford | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | JV Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | 2:30pm | |
| Wed., 10/17 | V Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | L 6-0 | 2:30pm | |
| Wed., 10/17 | JV Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 5:15 p.m. | ||
| Wed., 10/17 | V Girls Soccer | Wolcott | Home - Haddam Killingworth HS [Directions] | L 1-3 | ||
| Wed., 10/17 | JV Girls Soccer | Old Lyme | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Wed., 10/17 | V Girls Swimming and Diving | Lyman Hall | Away - Sheehan Pool [Directions] | 5:00 p.m. | 3:15pm | |
| Thu., 10/18 | V Boys Soccer | University/Prince Tech | Home - Haddam Killingworth HS [Directions] | W 5-0 | ||
| Fri., 10/19 | V Boys Cross Country | Shoreline Championship | Away - Nathan Hale Ray HS | 2:30 p.m. | 12:10pm | |
| Fri., 10/19 | V Girls Cross Country | Shoreline Championship | Away - Nathan Hale Ray HS | 2:30 p.m. | 12:10pm | |
| Fri., 10/19 | V Field Hockey | North Branford | Away - North Branford HS [Directions] | L 0-3 | ||
| Fri., 10/19 | JV Field Hockey | North Branford | Away - North Branford HS [Directions] | 4:30 p.m. | ||
| Fri., 10/19 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Home - Haddam Killingworth HS [Directions] | 4:15 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | Valley Regional | Away - Valley Regional HS [Directions] | W 3-2 | 2:30pm | |
| Fri., 10/19 | JV Girls Volleyball | Valley Regional | Away - Valley Regional HS [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 10/20 | V Boys Soccer | Bacon Academy | Away - Football/ Soccer Field [Directions] | L 0-1 | 11:15am | |
| Sat., 10/20 | V Field Hockey | Valley Regional | Home - Haddam Killingworth HS [Directions] | L 1-0 | ||
| Sat., 10/20 | JV Field Hockey | Valley Regional | Home - Haddam Killingworth HS [Directions] | 1:00 p.m. | ||
| Mon., 10/22 | V Boys Soccer | Cromwell | Away - Cromwell HS [Directions] | W 3-2 | 4:30pm | |
| Tue., 10/23 | V Field Hockey | Mercy | Home - Haddam Killingworth HS [Directions] | L 1-3 | ||
| Tue., 10/23 | JV Field Hockey | Mercy | Home - Haddam Killingworth HS [Directions] | 5:15 p.m. | ||
| Tue., 10/23 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Away - Windsor Locks HS [Directions] | 5:00 p.m. | 4:00pm | |
| Wed., 10/24 | V Boys Cross Country | Running Rams Inv. (Fresh/Soph) | Away - Old Saybrook HS | 3:30 p.m. | 2:30pm | |
| Wed., 10/24 | V Girls Cross Country | Running Rams Inv. (Fresh/Soph) | Away - Old Saybrook HS | 3:30 p.m. | 2:30pm | |
| Wed., 10/24 | V Field Hockey | Guilford | Home - Haddam Killingworth HS [Directions] | L 6-1 | ||
| Wed., 10/24 | JV Field Hockey | Guilford | Home - Haddam Killingworth HS [Directions] | 5:15 p.m. | ||
| Wed., 10/24 | V Girls Soccer | Hale Ray | Home - Haddam Killingworth HS [Directions] | W 6-0 | ||
| Wed., 10/24 | V Girls Volleyball | Lyman Memorial | Away - Lyman Memorial HS - Gymnasium [Directions] | W 3-0 | 3:15pm | |
| Wed., 10/24 | JV Girls Volleyball | Lyman Hall | Away - Lyman Memorial [Directions] | 4:30 p.m. | 2:30pm | |
| Thu., 10/25 | V Boys Soccer | Cromwell | Home - Haddam Killingworth HS [Directions] | L 2-7 | ||
| Fri., 10/26 | V Football | North Branford | Away - NBHS Colafati Field [Directions] | W 27-6 | 4:45pm | |
| Fri., 10/26 | JV Boys Soccer | East Hampton | Home - Haddam-Killingworth HS [Directions] | 3:45 p.m. | 2:30pm | |
| Fri., 10/26 | V Girls Volleyball | East Hampton | Away - East Hampton HS [Directions] | W 3-2 | ||
| Fri., 10/26 | JV Girls Volleyball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | ||
| Sat., 10/27 | V Boys Cross Country | Class SS State Championship | Away - Manchester - Wickham | 1:00 p.m. | 9:00am | |
| Sat., 10/27 | V Girls Cross Country | Class SS State Championship | Away - Manchester - Wickham | 1:00 p.m. | 9:00am | |
| Mon., 10/29 | V Boys Cross Country | Valley Freshman Invitational | Away - Valley Regional | 3:30 p.m. | 2:30pm | |
| Mon., 10/29 | V Girls Cross Country | Valley Freshman Invitational | Away - Valley Regional | 3:30 p.m. | 2:30pm | |
| Mon., 10/29 | V Girls Volleyball | Cromwell | Home - Haddam Killingworth HS [Directions] | W 3-1 | ||
| Tue., 10/30 | V Boys Soccer | Cromwell | Home - Haddam Killingworth HS [Directions] | W 2-1 | ||
| Tue., 10/30 | V Girls Volleyball | East Hampton | Away - East Hampton HS [Directions] | L 3-2 | 3:45pm | |
| Thu., 11/1 | V Boys Cross Country | CT State Open Championship | Away - Manchester - Wickham | 2:00 p.m. | 11:30am | |
| Thu., 11/1 | V Boys Soccer | Valley Regional | Away - Valley Regional HS [Directions] | W 3-2 | 4:45pm | |
| Thu., 11/1 | V Girls Cross Country | CT State Open Championship | Away - Manchester - Wickham | 2:00 p.m. | 11:30am | |
| Fri., 11/2 | V Girls Swimming and Diving | Nutmeg Championship | Away - Windsor Locks | 5:00 p.m. | 2:45pm | |
| Fri., 11/2 | V Girls Swimming and Diving | Nutmeg Conference Championship | Away - Windsor Locks | TBA | TBA | |
| Sat., 11/3 | V Boys Soccer | Morgan | Away - Indian River Complex [Directions] | L 0-3 | 4:15pm | |
| Sun., 11/4 | V Football | Lewis Mills | Away - Lewis Mills Track [Directions] | W 42-0 | 11:45am | |
| Mon., 11/5 | JV Football | Lewis Mills | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Mon., 11/5 | V Girls Volleyball | Lauralton Hall | Home - Haddam Killingworth HS [Directions] | W 3-0 | ||
| Wed., 11/7 | V Boys Soccer | Nonnewaug | Away - Nonnewaug [Directions] | W 4-0 | 10:00am | |
| Wed., 11/7 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:00 p.m. | 2:45pm | |
| Thu., 11/8 | V Boys Soccer | Granby Memorial | Away - Granby Memorial HS [Directions] | L 1-3 | 3:45pm | |
| Sat., 11/10 | V Boys Cross Country | New England Championship | Away - Manchester - NH | TBA | TBA | |
| Sat., 11/10 | V Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | W 42-12 | 10:30am | |
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Manchester - Wickham | TBA | TBA | |
| Sat., 11/10 | V Girls Swimming and Diving | Class S State Tournament | Away - Cheshire Community Pool | TBA | TBA | |
| Mon., 11/12 | JV Football | Old Saybrook | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Wed., 11/14 | V Girls Swimming and Diving | Divisional Swim Championships | Away - Wesleyan | TBA | TBA | |
| Sat., 11/17 | JV Football | Valley Regional/Old Lyme | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Tue., 11/20 | V Football | Valley Regional/Old Lyme | Away - VRHS Football Field [Directions] | W 27-21 | 5:00pm | |
| Tue., 11/27 | V Football | Bullard/Kolbe | Away - Kennedy Stadium [Directions] | W 52-0 | 3:30pm | |
| Sun., 12/2 | V Football | Stafford/East Windsor/Somers | Away - Enfield HS [Directions] | W 21-14(OT) | 10:00am | |
| Fri., 12/7 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | L 2-8 | 6:00 p.m. | |
| Sat., 12/8 | V Boys Basketball | Bacon Academy (Scrim.) | Home - Haddam Killingworth HS [Directions] | 2:00 p.m. | ||
| Sat., 12/8 | V Football | Bloomfield | Away - TBA [Directions] | L 25-7 | Yes | |
| Mon., 12/10 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | L 0-6 | 3:15 p.m. | |
| Tue., 12/11 | V Boys Basketball | Bolton (Scrim.) | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Tue., 12/11 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | L 22-61 | 4:15pm | |
| Tue., 12/11 | JV Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:45 p.m. | ||
| Wed., 12/12 | V Boys Indoor Track | Shoreline Developmental Meet | Away - Little Athletic Center @ Hillhouse HS | 5:30 p.m. | 3:00pm | |
| Wed., 12/12 | V Wrestling | Morgan | Home - Haddam Killingworth MS in Killingworth [Directions] | 6:00 p.m. | ||
| Wed., 12/12 | V Girls Indoor Track | Shoreline Developmental Meet | Away - Little Athletic Center @ Hillhouse HS | 5:30 p.m. | 3:00pm | |
| Thu., 12/13 | V Boys Basketball | Portland | Away - Portland HS [Directions] | L 48-65 | 4:15pm | |
| Thu., 12/13 | JV Boys Basketball | Portland | Away - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 12/13 | V Girls Basketball | Portland | Home - Haddam Killingworth HS [Directions] | L 33-75 | ||
| Thu., 12/13 | JV Girls Basketball | Portland | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Sat., 12/15 | V Wrestling | Wethersfield Tournament | Away - Wethersfield | TBA | Yes | |
| Sat., 12/15 | V Girls Basketball | Westbrook | Home - Haddam Killingworth HS [Directions] | L 44-58 | ||
| Sat., 12/15 | JV Girls Basketball | Westbrook | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Mon., 12/17 | V Girls Basketball | Bolton | Home - Haddam Killingworth HS [Directions] | L 43-51 | ||
| Tue., 12/18 | FR Boys Basketball | Westbrook | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 12/19 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | L 2-6 | 2:15pm | |
| Thu., 12/20 | V Girls Basketball | Stonington | Home - Haddam Killingworth HS [Directions] | L 16-64 | ||
| Thu., 12/20 | JV Girls Basketball | Stonington | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Sat., 12/22 | FR Boys Basketball | Morgan | Away - Morgan HS [Directions] | 4:00 p.m. | Yes | |
| Sat., 12/22 | V Wrestling | Simsbury Tournament | Away - Simsbury | TBA | Yes | |
| Thu., 12/27 | V Boys Basketball | Comp Sci | Away - Civic Leadership HS [Directions] | W 75-55 | 10:30am | |
| Thu., 12/27 | JV Boys Basketball | Comp Sci | Away - Civic Leadership HS [Directions] | 12:00 p.m. | ||
| Thu., 12/27 | FR Boys Basketball | Portland | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invite | Away - Little Athletic Center @ Hillhouse HS | 11:30 a.m. | 9:30am | |
| Thu., 12/27 | V Wrestling | Daniel Hand | Away - Polson Gym/DHHS Campus [Directions] | 6:00 p.m. | 4:15pm | |
| Thu., 12/27 | V Girls Gymnastics | Mercy, Valley Regional, Jonathan Law | Away - Flip Flop Gymnastics, Deep River [Directions] | 63 | ||
| Thu., 12/27 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks [Directions] | L 0-9 | 12pm | |
| Thu., 12/27 | V Girls Indoor Track | Jack Long Invite | Away - Little Athletic Center @ Hillhouse HS | 11:30 a.m. | 9:30am | |
| Fri., 12/28 | V Wrestling | Ledyard Duals | Away - Ledyard | 10:00 a.m. | Yes | |
| Fri., 12/28 | V Girls Basketball | Morgan | Away - Morgan HS [Directions] | L 21-43 | 4:30pm | |
| Fri., 12/28 | JV Girls Basketball | Morgan | Away - Morgan HS [Directions] | 5:30 p.m. | ||
| Fri., 12/28 | V Girls Ice Hockey | Alumni Game | Home - Northford Ice Pavilion [Directions] | 5:45 p.m. | 4pm | |
| Sat., 12/29 | V Boys Basketball | Ellis Tech | Away - Ellis Tech Gymnasium [Directions] | W 70-32 | 9:00am | |
| Sat., 12/29 | JV Boys Basketball | Ellis Tech | Away - Ellis Tech Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/29 | V Boys Indoor Track | Hillhouse Winter Relays | Away - Little Athletic Center @ Hillhouse HS | 9:00 a.m. | 7:15am | |
| Sat., 12/29 | V Girls Gymnastics | Mercy, Valley Regional, Stonington | Away - Flip Flop Gym [Directions] | 74.4 | ||
| Sat., 12/29 | V Girls Indoor Track | Hillhouse Winter Relays | Away - Little Athletic Center @ Hillhouse HS | 9:00 a.m. | 7:15am | |
| Wed., 1/2 | V Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 47-67 | 4:15pm | |
| Wed., 1/2 | JV Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Wed., 1/2 | V Girls Basketball | Old Lyme | Home - Haddam Killingworth HS [Directions] | L 48-60 | ||
| Wed., 1/2 | JV Girls Basketball | Old Lyme | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Thu., 1/3 | FR Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 7:00 p.m. | Yes | |
| Thu., 1/3 | V Boys Indoor Track | Shoreline League Meet #1 | Away - Little Athletic Center @ Hillhouse HS | 5:30 p.m. | 3:00pm | |
| Thu., 1/3 | V Boys Swimming and Diving | Granby Memorial | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 1/3 | V Girls Gymnastics | Mercy, Valley Regional, Hamden | Away - Flip Flop Gymnastics, Deep River [Directions] | 81.2 | ||
| Thu., 1/3 | V Girls Indoor Track | Shoreline League Meet #1 | Away - Little Athletic Center @ Hillhouse HS | 5:30 p.m. | 3:00pm | |
| Fri., 1/4 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | W 60-47 | 4:15pm | |
| Fri., 1/4 | JV Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | ||
| Fri., 1/4 | V Girls Basketball | Hale Ray | Home - Haddam Killingworth HS [Directions] | W 43-15 | ||
| Fri., 1/4 | JV Girls Basketball | Hale Ray | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Sat., 1/5 | FR Boys Basketball | Old Saybrook | Home - Haddam Killingworth HS [Directions] | 10:30 a.m. | ||
| Sat., 1/5 | V Boys Indoor Track | Elm City Coaches Meet | Away - Little Athletic Center @ Hillhouse HS | 9:00 a.m. | 7:00AM | |
| Sat., 1/5 | V Wrestling | Chad Antoch Tournament | Away - Westerly, RI | TBA | Yes | |
| Sat., 1/5 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden Ice Rink [Directions] | L 4-5 | 6:15pm | |
| Sat., 1/5 | V Girls Indoor Track | Elm City Coaches Invitational | Away - Little Athletic Center @ Hillhouse HS | 9:00 a.m. | 7:00AM | |
| Mon., 1/7 | V Boys Basketball | Coginchaug | Home - Haddam Killingworth HS [Directions] | W 59-57 | ||
| Mon., 1/7 | JV Boys Basketball | Coginchaug | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Mon., 1/7 | V Boys Swimming and Diving | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | 7:00 p.m. | 5:45pm | |
| Tue., 1/8 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | L 32-63 | 4:15pm | |
| Tue., 1/8 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 5:30 p.m. | ||
| Wed., 1/9 | V Wrestling | Portland/Cromwell | Away - Portland HS [Directions] | 6:30 p.m. | 4:00pm | |
| Wed., 1/9 | V Girls Basketball | Aerospace | Away - Academy of Aerospace and Engineering [Directions] | W 69-47 | 2:30pm | |
| Wed., 1/9 | V Girls Ice Hockey | Hamden Coop | Home - Northford Ice Pavilion [Directions] | L 1-7 | 6:30 p.m. | |
| Thu., 1/10 | V Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | L 31-54 | 4:30pm | |
| Thu., 1/10 | JV Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 5:30 p.m. | ||
| Thu., 1/10 | V Girls Gymnastics | Mercy, Valley Regional, Old Lyme | Away - Flip Flop Gym [Directions] | 87.25 | ||
| Thu., 1/10 | V Girls Ice Hockey | Masuk Coop | Home - Northford Ice Pavilion [Directions] | W 9-1 | 2:30 p.m. | |
| Fri., 1/11 | V Boys Indoor Track | Yale Invitational | Away - Cox Cage | TBA | TBA | |
| Fri., 1/11 | V Girls Basketball | Valley Regional | Home - Haddam Killingworth HS [Directions] | L 34-54 | ||
| Fri., 1/11 | JV Girls Basketball | Valley Regional | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Fri., 1/11 | V Girls Indoor Track | Yale Invitational | Away - Cox Cage | TBA | TBA | |
| Sat., 1/12 | FR Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 9:00 a.m. | Yes | |
| Sat., 1/12 | V Boys Indoor Track | Shoreline Coaches Invite | Away - Little Athletic Center @ Hillhouse HS | 9:30 a.m. | 7:30am | |
| Sat., 1/12 | V Boys Indoor Track | Yale Invitational | Away - Cox Cage | TBA | TBA | |
| Sat., 1/12 | V Wrestling | Canton Duals | Away - Canton | TBA | Yes | |
| Sat., 1/12 | V Girls Ice Hockey | Guilford Coop | Home - Northford Ice Pavilion [Directions] | L 2-5 | 5:30 p.m. | |
| Sat., 1/12 | V Girls Indoor Track | Shoreline Coaches Invite | Away - Little Athletic Center @ Hillhouse HS | 9:30 a.m. | 7:30am | |
| Sat., 1/12 | V Girls Indoor Track | Yale Invitational | Away - Cox Cage | TBA | TBA | |
| Mon., 1/14 | V Boys Basketball | Old Saybrook | Home - Haddam Killingworth HS [Directions] | L 59-69 | ||
| Mon., 1/14 | JV Boys Basketball | Old Saybrook | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Mon., 1/14 | V Boys Indoor Track | OS Indoor Qualifier | Away - Little Athletic Center @ Hillhouse HS | 5:30 p.m. | 3:00pm | |
| Mon., 1/14 | V Girls Indoor Track | OS Indoor Qualifier | Away - Little Athletic Center @ Hillhouse HS | 5:30 p.m. | 3:00PM | |
| Tue., 1/15 | V Boys Swimming and Diving | Sheehan/Lyman Hall | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Tue., 1/15 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | W 55-48 | 4:15pm | |
| Tue., 1/15 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Wed., 1/16 | FR Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | Cancelled | Yes | |
| Fri., 1/18 | V Boys Indoor Track | HK Invite | Away - Little Athletic Center @ Hillhouse HS | 5:00 p.m. | 3:00pm | |
| Fri., 1/18 | V Boys Swimming and Diving | Brookfield | Home - Haddam Killingworth HS [Directions] | 4:30 p.m. | ||
| Fri., 1/18 | V Girls Basketball | North Branford | Away - North Branford HS [Directions] | L 45-46 | 4:00pm | |
| Fri., 1/18 | JV Girls Basketball | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | ||
| Fri., 1/18 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Northford Ice Pavilion [Directions] | L 2-3 | 7 p.m. | |
| Fri., 1/18 | V Girls Indoor Track | HK Invite | Away - Little Athletic Center @ Hillhouse HS | 5:00 p.m. | 3:00pm | |
| Sat., 1/19 | FR Boys Basketball | Coginchaug | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Sat., 1/19 | V Boys Indoor Track | SCC Invitational | Away - Little Athletic Center @ Hillhouse HS | Cancelled | TBA | |
| Sat., 1/19 | V Wrestling | Cougar Duals | Home - Haddam Killingworth HS [Directions] | 9:00 a.m. | ||
| Sat., 1/19 | V Girls Ice Hockey | Simsbury | Away - ISCC [Directions] | L 0-6 | 11:45 a.m. | |
| Sat., 1/19 | V Girls Indoor Track | SCC Invitational | Away - Little Athletic Center @ Hillhouse HS | Cancelled | TBA | |
| Mon., 1/21 | V Boys Indoor Track | FRESH/SOPH INVITE | Away - Little Athletic Center @ Hillhouse HS | 10:00 a.m. | 8:00am | |
| Mon., 1/21 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton - Lower [Directions] | L 0-5 | 11:45 a.m. | |
| Mon., 1/21 | V Girls Indoor Track | FRESH/SOPH INVITATIONAL | Away - Little Athletic Center @ Hillhouse HS | 10:00 a.m. | 8:00am | |
| Tue., 1/22 | V Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | L 55-76 | 2:30pm | |
| Tue., 1/22 | JV Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | Cancelled | ||
| Tue., 1/22 | V Girls Basketball | Cromwell | Home - Haddam Killingworth HS [Directions] | L 38-61 | ||
| Tue., 1/22 | JV Girls Basketball | Cromwell | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Wed., 1/23 | V Boys Basketball | Wheeler | Home - Haddam Killingworth HS [Directions] | W 53-38 | ||
| Wed., 1/23 | JV Boys Basketball | Wheeler | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 1/23 | V Wrestling | Ellis Tech | Away - Ellis Tech [Directions] | 5:00 p.m. | ||
| Wed., 1/23 | V Girls Ice Hockey | West Haven/SHA | Home - Northford Ice Pavilion [Directions] | L 2-8 | 4:30pm | |
| Thu., 1/24 | V Boys Swimming and Diving | Lyman Hall | Away - Sheehan Pool [Directions] | 5:00 p.m. | 3:15pm | |
| Thu., 1/24 | V Girls Gymnastics | Mercy, Daniel Hand, Valley Regional | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 66.60 | ||
| Fri., 1/25 | V Boys Basketball | Morgan | Home - Haddam Killingworth HS [Directions] | L 52-54 | ||
| Fri., 1/25 | JV Boys Basketball | Morgan | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Fri., 1/25 | V Boys Indoor Track | Shoreline League Meet #2 | Away - Little Athletic Center @ Hillhouse HS | 5:00 p.m. | 3:00pm | |
| Fri., 1/25 | V Girls Indoor Track | Shoreline League Meet #2 | Away - Little Athletic Center @ Hillhouse HS | 5:00 p.m. | 3:00pm | |
| Sat., 1/26 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 12:00 p.m. | Yes | |
| Sat., 1/26 | V Boys Indoor Track | Bacon Invitational | Away - Little Athletic Center @ Hillhouse HS | 4:30 p.m. | 2:30PM | |
| Sat., 1/26 | V Wrestling | Hastings Duals | Away - Newington HS | 9:30 a.m. | 7:00am | |
| Sat., 1/26 | V Girls Indoor Track | Bacon Invitational | Away - Little Athletic Center @ Hillhouse HS | 4:30 p.m. | 2:30pm | |
| Mon., 1/28 | V Girls Basketball | Morgan | Home - Haddam Killingworth HS [Directions] | L 38-57 | ||
| Mon., 1/28 | JV Girls Basketball | Morgan | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Tue., 1/29 | V Boys Basketball | Morgan | Away - Morgan HS [Directions] | L 45-64 | 4:30pm | |
| Tue., 1/29 | JV Boys Basketball | Morgan | Away - Morgan HS [Directions] | 5:30 p.m. | ||
| Tue., 1/29 | V Boys Swimming and Diving | Waterford/Ledyard | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | V Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | L 41-54 | 4:15pm | |
| Thu., 1/31 | JV Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Boys Basketball | Valley Regional | Home - Haddam Killingworth HS [Directions] | L 45-74 | ||
| Fri., 2/1 | JV Boys Basketball | Valley Regional | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | W 8-0 | 2:45 p.m. | |
| Sat., 2/2 | V Boys Indoor Track | Shoreline Championship | Away - Little Athletic Center @ Hillhouse HS | 10:00 a.m. | 8:30am | |
| Sat., 2/2 | V Wrestling | Stafford Invitational | Away - Stafford | 9:15 a.m. | 7:00am | |
| Sat., 2/2 | V Girls Ice Hockey | Woodstock Academy Coop (Scrim.) | Home - Northford Ice Pavilion [Directions] | 7:00 p.m. | 4:15 p.m. | |
| Sat., 2/2 | V Girls Indoor Track | Shoreline Championship | Away - Little Athletic Center @ Hillhouse HS | 10:00 a.m. | 8:30am | |
| Sun., 2/3 | V Girls Ice Hockey | Avon | Home - Northford Ice Pavilion [Directions] | L 3-6 | 9:30 a.m. | |
| Mon., 2/4 | V Boys Basketball | Ellis Tech | Home - Haddam Killingworth HS [Directions] | W 66-32 | ||
| Mon., 2/4 | JV Boys Basketball | Ellis Tech | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Tue., 2/5 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | L 45-48 | 4:15pm | |
| Tue., 2/5 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 5:30 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Coginchaug | Home - Haddam Killingworth HS [Directions] | L 45-64 | ||
| Tue., 2/5 | JV Girls Basketball | Coginchaug | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 2/6 | FR Boys Basketball | Valley Regional | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 2/6 | V Girls Gymnastics | Mercy, Valley Regional, Hamden | Away - Flip Flop Gymnastics, Deep River [Directions] | 73.4 | ||
| Wed., 2/6 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford Ice Pavilion [Directions] | L 1-6 | 6:45 P.M. | |
| Thu., 2/7 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 2/7 | V Girls Basketball | North Branford | Home - Haddam Killingworth HS [Directions] | L 37-54 | ||
| Thu., 2/7 | JV Girls Basketball | North Branford | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Thu., 2/7 | V Girls Ice Hockey | Northwest Catholic | Home - Northford Ice Pavilion [Directions] | W 10-2 | 2:15 p.m. | |
| Thu., 2/7 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 2/8 | V Boys Basketball | North Branford | Away - North Branford HS [Directions] | W 72-59 | 4:00pm | |
| Fri., 2/8 | JV Boys Basketball | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | ||
| Fri., 2/8 | V Boys Swimming and Diving | Suffield | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 2/8 | V Girls Gymnastics | Valley Regional, Old Lyme | Away - ABC [Directions] | 66.9 | ||
| Sat., 2/9 | FR Boys Basketball | Cromwell | Home - Haddam Killingworth HS [Directions] | 10:00 a.m. | ||
| Sat., 2/9 | V Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 29-58 | 2:15pm | |
| Sat., 2/9 | JV Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 3:30 p.m. | ||
| Sat., 2/9 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | L 0-4 | 10:15 a.m. | |
| Mon., 2/11 | V Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | L 28-71 | 4:15pm | |
| Mon., 2/11 | JV Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 5:30 p.m. | ||
| Mon., 2/11 | V Girls Ice Hockey | Suffield Coop | Home - Northford Ice Pavilion [Directions] | L 1-7 | 2:30pm | |
| Wed., 2/13 | V Boys Basketball | Cromwell | Home - Haddam Killingworth HS [Directions] | L 48-77 | ||
| Wed., 2/13 | JV Boys Basketball | Cromwell | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 2/13 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | L 1-4 | 2:45 p.m. | |
| Thu., 2/14 | V Girls Gymnastics | Mercy, Daniel Hand, Valley Regional | Away - Hand [Directions] | 74.3 | ||
| Fri., 2/15 | V Boys Basketball | North Branford | Home - Haddam Killingworth HS [Directions] | W 66-57 | ||
| Fri., 2/15 | JV Boys Basketball | North Branford | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Fri., 2/15 | V Boys Swimming and Diving | Granby Memorial | Away - Farmington Valley YMCA [Directions] | 4:00 p.m. | ||
| Fri., 2/15 | V Girls Ice Hockey | Branford | Home - Northford Ice Pavilion [Directions] | L N/A | 2:15pm | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 10:15am | |
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 10:15am | |
| Mon., 2/18 | V Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | L 48-50 | 4:15pm | |
| Mon., 2/18 | JV Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/18 | V Girls Ice Hockey | SCC South - 1st Round | Away - TBA | TBA | TBA | |
| Thu., 2/21 | V Boys Basketball | East Hampton | Home - Haddam Killingworth HS [Directions] | L 53-62 | ||
| Thu., 2/21 | JV Boys Basketball | East Hampton | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Fri., 2/22 | V Boys Swimming and Diving | Classical Magnet | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Fri., 2/22 | V Girls Ice Hockey | SCC South Semi-Finals | Away - Bennett | TBA | TBA | |
| Thu., 2/28 | V Boys Swimming and Diving | Nutmeg Conference Championship | Away - Windsor Locks | TBA | TBA | |
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | Cancelled | TBA | |
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | Cancelled | TBA | |
| Tue., 3/5 | V Boys Basketball | Morgan | Away - Morgan HS [Directions] | 7:00 p.m. | 6:00pm | |
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | Cancelled | 2:30pm | |
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Cheshire Community Pool [Directions] | 3:00 p.m. | 12:15pm | |
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | 4:15pm | |
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | Cancelled | 3:00pm | |
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | 4:00pm | |
| Tue., 3/19 | V Girls Lacrosse | Branford (Scrim.) | Away - Branford HS-Turf Field [Directions] | 5:30 p.m. | 4:15pm | |
| Thu., 3/21 | V Baseball | North Haven (Scrim.) | Away - North Haven Athletic Complex-DeMayo Field [Directions] | 3:45 p.m. | 2:30pm | |
| Sun., 3/24 | V Baseball | Hopkinton (MA) (Scrim.) | Home - Haddam Killingworth HS [Directions] | 12:00 p.m. | ||
| Mon., 3/25 | V Baseball | Bolton (Scrim.) | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Softball | Bolton (Scrim.) | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | V Baseball | Portland (Scrim.) | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Baseball | Lyman Memorial (Scrim.) | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Softball | East Lyme (Scrim.) | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Baseball | Middletown (Scrim.) | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Sat., 3/30 | V Boys Tennis | Cromwell | Away - Watrous Park [Directions] | L 2-6 [Detailed Results] | 9:45am | |
| Sat., 3/30 | V Softball | Stonington (Scrim.) | Home - Haddam Killingworth HS [Directions] | 11:00 a.m. | ||
| Sat., 3/30 | V Girls Tennis | Cromwell | Home - Haddam Killingworth HS [Directions] | W 6-1 | ||
| Mon., 4/1 | V Baseball | Old Saybrook | Home - Haddam Killingworth HS [Directions] | W 10-0 | ||
| Mon., 4/1 | V Boys Tennis | Westbrook | Away - Westbrook HS/MS Tennis Courts [Directions] | L 0-7 [Detailed Results] | 2:30pm | |
| Mon., 4/1 | V Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | L 18-8 | TBA | |
| Mon., 4/1 | JV Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 4/1 | V Softball | Old Saybrook | Home - Haddam Killingworth HS [Directions] | W 6-5 | ||
| Mon., 4/1 | V Girls Tennis | Westbrook | Home - Haddam Killingworth HS [Directions] | L 2-5 | ||
| Tue., 4/2 | JV Baseball | Old Saybrook | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Tue., 4/2 | V Boys Lacrosse | North Branford | Home - HK HS [Directions] | W 8-6 | ||
| Tue., 4/2 | JV Boys Lacrosse | North Branford | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | V Girls Lacrosse | North Branford | Away - North Branford HS [Directions] | L 21-6 | 2:30pm | |
| Tue., 4/2 | JV Girls Lacrosse | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | ||
| Wed., 4/3 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | W 11-4 | 2:30pm | |
| Wed., 4/3 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | L 5-4 | 2:30pm | |
| Thu., 4/4 | JV Baseball | Hale Ray | Home - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Thu., 4/4 | V Boys Lacrosse | Cromwell | Away - Cromwell HS [Directions] | W 17-1 | 2:30pm | |
| Thu., 4/4 | JV Boys Lacrosse | Cromwell | Away - Cromwell HS [Directions] | 5:30 p.m. | ||
| Thu., 4/4 | V Girls Tennis | North Branford | Home - Haddam Killingworth HS [Directions] | L 1-6 | ||
| Fri., 4/5 | V Baseball | East Hampton | Home - Haddam Killingworth HS [Directions] | W 2-0 | ||
| Fri., 4/5 | V Boys Tennis | North Branford | Home - Haddam Killingworth HS [Directions] | W 7-0 | ||
| Fri., 4/5 | V Softball | East Hampton | Home - Haddam Killingworth HS [Directions] | W 13-1 | ||
| Sat., 4/6 | JV Baseball | East Hampton | Home - Haddam-Killingworth HS [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | V Boys Outdoor Track | Hand Freshman Invitational | Away - Hand | 9:00 a.m. | 7:30am | |
| Sat., 4/6 | V Girls Outdoor Track | Hand Freshman Invitational | Away - Hand | 9:00 a.m. | 7:30am | |
| Tue., 4/9 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS [Directions] | W 11-2 | 2:30pm | |
| Tue., 4/9 | JV Baseball | ValleyReg/Westbrook | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Golf | North Branford | Home - Black Birch [Directions] | HK: 190, NB: 262 (League) | 2:15pm | |
| Tue., 4/9 | V Boys Lacrosse | Old Saybrook | Home - Old Saybrook HS [Directions] | W 17-2 | ||
| Tue., 4/9 | V Boys Tennis | Valley Regional | Home - Haddam Killingworth HS [Directions] | L 1-6 [Detailed Results] | ||
| Tue., 4/9 | V Girls Lacrosse | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 17-5 | 2:30pm | |
| Tue., 4/9 | JV Girls Lacrosse | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | V Softball | Valley Regional | Away - Valley Regional HS [Directions] | L 6-0 | 2:30pm | |
| Tue., 4/9 | V Girls Tennis | Valley Regional | Away - Valley Regional HS [Directions] | L 0-7 | 2:30pm | |
| Wed., 4/10 | V Baseball | North Branford | Home - Haddam Killingworth HS [Directions] | W 5-1 | ||
| Wed., 4/10 | V Boys Tennis | Morgan | Home - Haddam Killingworth HS [Directions] | L 0-7 [Detailed Results] | ||
| Wed., 4/10 | V Softball | North Branford | Home - Haddam Killingworth HS [Directions] | L 11-5 | ||
| Wed., 4/10 | V Girls Tennis | Morgan | Away - Morgan HS [Directions] | L 2-5 | 2:30pm | |
| Thu., 4/11 | JV Baseball | North Branford | Away - North Branford HS [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 4/11 | V Boys Golf | Morgan | Home - Black Birch [Directions] | HK: 192, Morgan: 189 (League) | 2:15pm | |
| Thu., 4/11 | V Boys Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | L 8-14 | 2:30pm | |
| Thu., 4/11 | JV Boys Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Baseball | Morgan | Away - Morgan HS [Directions] | W 2-1 | 2:30pm | |
| Fri., 4/12 | V Girls Lacrosse | Old Lyme | Home - Haddam Killingworth HS [Directions] | L 19-9 | ||
| Fri., 4/12 | JV Girls Lacrosse | Old Lyme | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Softball | Morgan | Away - Morgan HS [Directions] | W 8-1 | 2:30pm | |
| Fri., 4/12 | V Girls Tennis | Coginchaug | Home - Haddam Killingworth HS [Directions] | L 3-4 | ||
| Tue., 4/16 | V Baseball | Portland | Away - Portland HS [Directions] | L 3-2 | 2:30pm | |
| Tue., 4/16 | V Boys Tennis | East Hampton | Home - Haddam Killingworth HS [Directions] | L 0-7 | ||
| Tue., 4/16 | V Girls Tennis | East Hampton | Away - East Hampton HS [Directions] | L 2-5 | 2:30pm | |
| Wed., 4/17 | V Baseball | Coginchaug | Home - Haddam Killingworth HS [Directions] | W 9-2 | ||
| Wed., 4/17 | JV Baseball | Rocky Hill | Away - Rocky Hill HS [Directions] | 3:45 p.m. | 2:30pm | |
| Wed., 4/17 | V Boys Tennis | Old Lyme | Away - Old Lyme HS [Directions] | L 0-7 | 2:30pm | |
| Wed., 4/17 | V Girls Lacrosse | Valley Regional | Home - Haddam Killingworth HS [Directions] | L 17-23 | ||
| Wed., 4/17 | JV Girls Lacrosse | Valley Regional | Home - Haddam Killingworth HS [Directions] | 2:30 p.m. | ||
| Wed., 4/17 | V Softball | Coginchaug | Home - Haddam Killingworth HS [Directions] | L 7-2 | ||
| Wed., 4/17 | V Girls Tennis | Old Lyme | Home - Haddam Killingworth HS [Directions] | L 2-5 | ||
| Thu., 4/18 | JV Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:45 p.m. | 9:30am | |
| Thu., 4/18 | V Boys Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | L 7-8 | 2:30pm | |
| Thu., 4/18 | JV Boys Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 5:30 p.m. | ||
| Fri., 4/19 | JV Baseball | Hale Ray (Scrim.) | Away - Hale-Ray HS [Directions] | 11:00 a.m. | 2:30pm | |
| Tue., 4/23 | JV Baseball | Cromwell | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Golf | Old Lyme | Home - Black Birch [Directions] | HK: 204, Old Lyme: 167 (League) | 2:15pm | |
| Tue., 4/23 | V Boys Lacrosse | Morgan | Home - Haddam Killingworth HS [Directions] | L 6-14 | ||
| Tue., 4/23 | JV Boys Lacrosse | Morgan | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | East Hampton, North Branford | Home - Haddam Killingworth HS [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | L 0-7 | 2:30pm | |
| Tue., 4/23 | V Girls Outdoor Track | East Hampton, North Branford | Home - Haddam Killingworth HS [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | V Softball | Portland | Away - Nolan Field [Directions] | W 3-0 | 2:30pm | |
| Tue., 4/23 | V Girls Tennis | Portland | Home - Haddam Killingworth HS [Directions] | W 4-3 | ||
| Wed., 4/24 | V Baseball | Westbrook | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | W 14-0 | 2:30pm | |
| Wed., 4/24 | V Boys Tennis | Cromwell | Home - Haddam Killingworth HS [Directions] | L 0-7 | ||
| Wed., 4/24 | V Girls Lacrosse | Mercy | Away - Mercy [Directions] | L 19-5 | 2:30pm | |
| Wed., 4/24 | JV Girls Lacrosse | Mercy | Away - Mercy [Directions] | 5:30 p.m. | ||
| Wed., 4/24 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS Field #5 - Softball [Directions] | W 21-1 | 2:30pm | |
| Wed., 4/24 | V Girls Tennis | Cromwell | Away - Watrous Park [Directions] | L 1-6 | 2:30pm | |
| Thu., 4/25 | V Baseball | Cromwell | Away - Fran Monnes Baseball Field @ Cromwell HS [Directions] | W 2-1 | 2:30pm | |
| Thu., 4/25 | JV Baseball | Westbrook | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Golf | Valley Regional | Away - Black Hall CC [Directions] | HK: 204, Valley: 226 (League) | tba | |
| Thu., 4/25 | V Boys Lacrosse | North Branford | Away - North Branford HS [Directions] | L 11-12 | 2:30pm | |
| Thu., 4/25 | JV Boys Lacrosse | North Branford | Away - North Branford HS [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | North Branford | Home - Haddam Killingworth HS [Directions] | L 18-5 | ||
| Thu., 4/25 | JV Girls Lacrosse | North Branford | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Softball | Cromwell | Away - Cromwell HS [Directions] | L 5-3 | 2:30pm | |
| Fri., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away - Bethel HS | Cancelled | 3:00pm | |
| Fri., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away - Bethel HS | Cancelled | 3:00pm | |
| Sat., 4/27 | V Baseball | Old Lyme | Home - Haddam Killingworth HS [Directions] | W 6-3 | ||
| Sat., 4/27 | JV Baseball | Old Lyme | Home - Haddam Killingworth HS [Directions] | 1:00 p.m. | 8:45am | |
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Bethel HS | 9:00 a.m. | 7:00am | |
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays | Away - Bethel HS | 9:00 a.m. | 7:00am | |
| Mon., 4/29 | V Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | L 8-6 | 2:30pm | |
| Mon., 4/29 | V Boys Golf | Hale Ray | Home - Black Birch [Directions] | HK: 185, Hale-Ray: 178 (League) | TBA | |
| Mon., 4/29 | V Girls Lacrosse | Mercy | Home - Haddam Killingworth HS [Directions] | L 5-19 | ||
| Mon., 4/29 | JV Girls Lacrosse | Mercy | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | V Softball | Coginchaug | Away - Atwell Field @ CRHS [Directions] | W 8-5 | 2;30pm | |
| Tue., 4/30 | V Boys Golf | North Branford | Home - Black Birch [Directions] | HK: 186, North Branford: 215 (Non-League) | 2:15pm | |
| Tue., 4/30 | JV Boys Lacrosse | Cromwell | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Tue., 4/30 | V Boys Outdoor Track | Cromwell, Coginchaug | Away - Cromwell HS [Directions] | 3:30 p.m. | 2:30pm | |
| Tue., 4/30 | V Boys Tennis | Westbrook | Home - Haddam Killingworth HS [Directions] | L 0-7 [Detailed Results] | ||
| Tue., 4/30 | V Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | L 18-7 | 4:00pm | |
| Tue., 4/30 | JV Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | Cancelled | ||
| Tue., 4/30 | V Girls Outdoor Track | Cromwell, Coginchaug | Away - Cromwell HS [Directions] | 3:30 p.m. | 2:30pm | |
| Tue., 4/30 | V Girls Tennis | Westbrook | Away - Westbrook HS/MS Tennis Courts [Directions] | L 0-7 | 2:30pm | |
| Wed., 5/1 | V Baseball | North Branford | Away - North Branford HS [Directions] | W 4-0 | 2:30pm | |
| Wed., 5/1 | V Boys Golf | Old Saybrook | Away - Fenwick [Directions] | HK: 196, Old Saybrook: 162 (League) | 2:15pm | |
| Wed., 5/1 | JV Boys Lacrosse | Capital Prep | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Tennis | North Branford | Away - North Branford HS [Directions] | W 7-0 | 2:30pm | |
| Wed., 5/1 | V Girls Lacrosse | Waterford | Away - Waterford HS [Directions] | L 10-20 | ||
| Wed., 5/1 | JV Girls Lacrosse | Waterford | Away - Waterford HS [Directions] | 6:30 p.m. | 3:30PM | |
| Wed., 5/1 | JV Girls Lacrosse | Waterford | Away - Alumni Turf Field [Directions] | 6:30 p.m. | ||
| Wed., 5/1 | V Softball | North Branford | Away - North Branford HS [Directions] | L 13-5 | 2:30pm | |
| Wed., 5/1 | V Girls Tennis | North Branford | Away - North Branford HS [Directions] | L 0-7 | 2:30pm | |
| Thu., 5/2 | JV Baseball | North Branford | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Golf | East Hampton | Home - Black Birch [Directions] | HK: 169, East Hampton: 194 (League) | tba | |
| Thu., 5/2 | V Boys Lacrosse | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | W 17-3 | 2:30pm | |
| Thu., 5/2 | JV Boys Lacrosse | Old Saybrook | Away [Directions] | Cancelled | ||
| Fri., 5/3 | V Boys Outdoor Track | Middletown Froshmore | Away - Middletown | 3:00 p.m. | 2:30pm | |
| Fri., 5/3 | V Girls Lacrosse | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 20-8 | ||
| Fri., 5/3 | JV Girls Lacrosse | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | V Girls Outdoor Track | Middletown Froshmore | Away - Middletown | 3:00 p.m. | 2:30pm | |
| Sat., 5/4 | V Baseball | ValleyReg/Westbrook | Home - Haddam Killingworth HS [Directions] | W 4-0 | ||
| Sat., 5/4 | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional HS [Directions] | 1:00 p.m. | 9:15am | |
| Sat., 5/4 | JV Boys Lacrosse | Holy Cross | Away - Holy Cross [Directions] | 2:30 p.m. | ||
| Sat., 5/4 | V Boys Outdoor Track | Middletown Invitational | Away - Middletown | 10:00 a.m. | 8:30am | |
| Sat., 5/4 | V Girls Outdoor Track | Middletown Invitational | Away - Middletown | 10:00 a.m. | 8:30am | |
| Mon., 5/6 | V Baseball | Cromwell | Home - Haddam Killingworth HS [Directions] | L 13-4 | ||
| Mon., 5/6 | V Boys Lacrosse | Holy Cross | Away - Post University [Directions] | W 15-0 | 11:15AM | |
| Mon., 5/6 | V Boys Tennis | Morgan | Away - Morgan HS [Directions] | L 0-7 | 5:45pm | |
| Mon., 5/6 | V Softball | Cromwell | Home - Haddam Killingworth HS [Directions] | W 6-5 | ||
| Mon., 5/6 | V Girls Tennis | Morgan | Home - Haddam Killingworth HS [Directions] | L 3-4 | ||
| Tue., 5/7 | JV Baseball | Cromwell | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 5/7 | V Boys Golf | Coginchaug | Away - Lyman Orchards [Directions] | HK: 198, Coginchaug: 158 (League) | 2:15pm | |
| Tue., 5/7 | V Boys Lacrosse | Old Lyme | Home - Haddam Killingworth HS [Directions] | W 9-7 | ||
| Tue., 5/7 | JV Boys Lacrosse | Old Lyme | Home - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Westbrook, Morgan | Away - Westbrook HS [Directions] | 3:30 p.m. | 2:30pm | |
| Tue., 5/7 | V Girls Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | L 23-12 | 2:30pm | |
| Tue., 5/7 | JV Girls Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | 6:00 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Westbrook, Morgan | Away - Westbrook HS [Directions] | 3:30 p.m. | 2:30pm | |
| Wed., 5/8 | V Baseball | Morgan | Home - Haddam Killingworth HS [Directions] | L 3-0 | ||
| Wed., 5/8 | V Boys Golf | Old Saybrook | Home - Black Birch [Directions] | HK: 179, Old Saybrook: 156 (Non-League) | 2:15pm | |
| Wed., 5/8 | V Boys Lacrosse | Suffield-Windsor Locks | Home - Haddam Killingworth HS [Directions] | W 17-1 | ||
| Wed., 5/8 | JV Boys Lacrosse | Suffield-Windsor Locks | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Wed., 5/8 | V Boys Tennis | Coginchaug | Home - Haddam Killingworth HS [Directions] | L 2-5 [Detailed Results] | ||
| Wed., 5/8 | V Girls Lacrosse | Suffield | Away - Ted Beneski Turf Field [Directions] | W 15-14 | 2:30pm | |
| Wed., 5/8 | JV Girls Lacrosse | Suffield | Away - Ted Beneski Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Morgan | Home - Haddam Killingworth HS [Directions] | W 8-4 | ||
| Wed., 5/8 | V Girls Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | W 6-1 | 2:30pm | |
| Thu., 5/9 | JV Baseball | Morgan | Away - Morgan HS [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 5/9 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | HK: 186, Cromwell: 180 (League) | 1:00pm | |
| Thu., 5/9 | V Boys Outdoor Track | Loucks Games | Away | Cancelled | 2:30PM | |
| Thu., 5/9 | V Boys Tennis | Valley Regional | Away - Valley Regional HS [Directions] | L 2-5 [Detailed Results] | 2:30pm | |
| Thu., 5/9 | V Girls Outdoor Track | Loucks Games | Away - White Plains, NY | Cancelled | 2:30PM | |
| Thu., 5/9 | V Girls Tennis | Valley Regional | Home - Haddam Killingworth HS [Directions] | L 0-7 | ||
| Fri., 5/10 | V Baseball | Windsor Locks | Away - Veteran's Memorial Park [Directions] | W 7-1 | 4:00pm | |
| Fri., 5/10 | V Boys Lacrosse | Vinal-Goodwin | Home - Haddam Killingworth HS [Directions] | W 8-0 | ||
| Fri., 5/10 | V Boys Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS | 3:30 a.m. | 2:30pm | |
| Fri., 5/10 | V Girls Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS | 3:30 a.m. | 2:30pm | |
| Fri., 5/10 | V Softball | Canton | Away - Canton H.S. [Directions] | W 7-1 | 2:30pm | |
| Sat., 5/11 | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 11:00 a.m. | 9:15am | |
| Sat., 5/11 | V Boys Outdoor Track | Loucks Games | Away - White Plains, NY | 9:00 a.m. | 6:15AM | |
| Sat., 5/11 | V Girls Lacrosse | Holy Cross | Home - Haddam Killingworth HS [Directions] | W 17-8 | ||
| Sat., 5/11 | JV Girls Lacrosse | Holy Cross | Home - Haddam Killingworth HS [Directions] | Cancelled | ||
| Sat., 5/11 | V Girls Outdoor Track | Loucks Games | Away - White Plains, NY | 9:00 a.m. | 6:15AM | |
| Tue., 5/14 | V Baseball | Ellington | Home - Haddam Killingworth HS [Directions] | W 10-8 | ||
| Tue., 5/14 | JV Baseball | Ellington | Away - Ellington HS [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 5/14 | V Boys Lacrosse | Valley Regional | Home - Haddam Killingworth HS [Directions] | W 10-9 | ||
| Tue., 5/14 | V Boys Tennis | East Hampton | Home - Haddam-Killingworth HS [Directions] | L 3-4 | 2:30pm | |
| Tue., 5/14 | V Girls Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | L 8-20 | 2:30pm | |
| Tue., 5/14 | JV Girls Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Golf | Portland, Coventry | Away - PGC [Directions] | HK: 200, Portland: 157 (League) | 1:50pm | |
| Wed., 5/15 | V Boys Lacrosse | Cromwell | Home - Haddam Killingworth HS [Directions] | W 18-4 | ||
| Wed., 5/15 | V Boys Outdoor Track | Shoreline Novice Meet | Home - Haddam Killingworth HS [Directions] | 3:30 p.m. | ||
| Wed., 5/15 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS [Directions] | L 1-6 | ||
| Wed., 5/15 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS [Directions] | L 3-4 | 2:30pm | |
| Wed., 5/15 | V Girls Outdoor Track | Shoreline Novice Meet | Home - Haddam Killingworth HS [Directions] | 3:30 p.m. | ||
| Wed., 5/15 | V Softball | Old Lyme | Home - Haddam Killingworth HS [Directions] | W 6-5 | ||
| Wed., 5/15 | V Girls Tennis | Old Saybrook | Home - Haddam Killingworth HS [Directions] | L 3-4 | ||
| Wed., 5/15 | V Girls Tennis | Old Saybrook | Home - Haddam Killingworth HS [Directions] | L 2-5 | 2:30pm | |
| Thu., 5/16 | V Boys Golf | Hale Ray | Away - Fox Hopyard CC [Directions] | HK: 189, Hale-Ray: 177, East Hampton: 232 (Non-League) | 2:15pm | |
| Thu., 5/16 | V Boys Lacrosse | Morgan | Away - Indian River Complex [Directions] | L 5-8 | 4:00pm | |
| Thu., 5/16 | JV Boys Lacrosse | Morgan | Away - Indian River Complex [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | V Boys Tennis | Old Lyme | Home - Haddam Killingworth HS [Directions] | L 0-7 | ||
| Thu., 5/16 | V Girls Lacrosse | Morgan | Home - Haddam Killingworth HS [Directions] | L 18-9 | ||
| Thu., 5/16 | JV Girls Lacrosse | Morgan | Home - Haddam Killingworth HS [Directions] | 6:00 p.m. | ||
| Thu., 5/16 | V Softball | Rockville | Home - Haddam Killingworth HS [Directions] | W 4-0 | ||
| Thu., 5/16 | V Girls Tennis | Portland | Away - Portland HS [Directions] | W 5-2 | 2:30pm | |
| Fri., 5/17 | V Boys Lacrosse | Vinal-Goodwin | Away - Vinal Tech Field [Directions] | W 13-3 | 2:30pm | |
| Fri., 5/17 | V Girls Tennis | East Hampton | Home - Haddam Killingworth HS [Directions] | L 1-6 | ||
| Sat., 5/18 | V Baseball | Coventry | Home - Haddam Killingworth HS [Directions] | L 1-0 | 2:30pm | |
| Sat., 5/18 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | L 0-7 | 7:00am | |
| Sun., 5/19 | V Softball | Bolton | Home - Haddam Killingworth HS [Directions] | W 12-3 | ||
| Tue., 5/21 | V Baseball | Old Lyme | Home - Haddam Killingworth HS [Directions] | W 11-4 | ||
| Tue., 5/21 | JV Baseball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 5/21 | V Boys Golf | East Hampton | Away - Black Birch Country Club [Directions] | HK: 177, East Hampton: 209 (Non-League) | 2:15pm | |
| Tue., 5/21 | V Boys Lacrosse | Morgan | Away - Indian River Complex [Directions] | 5:30 p.m. | 4:00pm | |
| Tue., 5/21 | V Softball | Valley Regional | Home - Haddam Killingworth HS [Directions] | L 4-0 | ||
| Wed., 5/22 | V Baseball | North Branford | Home - Haddam Killingworth HS [Directions] | W 4-2 | ||
| Wed., 5/22 | V Boys Golf | Shoreline Championship | Away - Stanley Golf Course | 9:00 a.m. | 7:00am | |
| Wed., 5/22 | V Boys Outdoor Track | Shoreline Championship | Away - Coginchaug HS | 1:30 p.m. | 12:00pm | |
| Wed., 5/22 | V Girls Outdoor Track | Shoreline Championship | Away - Coginchaug HS | 1:30 p.m. | 12:00pm | |
| Wed., 5/22 | V Softball | Woodstock Academy | Away - Weimann Softball Field/Bentley Complex [Directions] | W 9-5 | 2:30pm | |
| Thu., 5/23 | JV Baseball | Portland | Home - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Thu., 5/23 | V Softball | North Branford | Away - NBHS Softball Field [Directions] | 3:00 p.m. | 1:15pm | |
| Fri., 5/24 | V Baseball | Portland | Away - Palmer Field- Middletown [Directions] | L 2-1 | 4:15pm | |
| Mon., 5/27 | V Baseball | Alumni Game | Home - Haddam Killingworth HS [Directions] | 1:00 p.m. | ||
| Wed., 5/29 | V Baseball | Stonington | Home - Haddam Killingworth HS [Directions] | W 3-1 | ||
| Wed., 5/29 | V Boys Lacrosse | Morgan | Home - Haddam Killingworth HS [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | V Softball | Wilcox Tech | Away - Wilcox Tech School Field [Directions] | W 16-0 | 2:30pm | |
| Thu., 5/30 | V Baseball | East Catholic | Away - East Catholic [Directions] | W 3-2 | 1:00pm | |
| Sat., 6/1 | V Baseball | Wolcott | Away - Wolcott HS [Directions] | L 8-0 | 8:45am | |
| Sat., 6/1 | V Boys Lacrosse | East Catholic | Home - Haddam Killingworth HS [Directions] | 3:00 p.m. | ||
| Tue., 6/4 | V Boys Golf | Division III State Championship | Away - Fairview Farms - Harwinton | 8:30 a.m. | 6:15am | |