| Darien 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 707 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 9/12 | Miscellaneous Events | ACT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Sat., 9/26 | Miscellaneous Events | SAT Test @ DHS | Home - Darien HS-TBA [Directions] | 12:00 p.m. | ||
| Tue., 9/29 | V Boys Soccer | Westhill (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 10/1 | V Boys Cross Country | New Canaan | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | W 1-0 | |
| Thu., 10/1 | V Girls Cross Country | New Canaan | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | OT-L 2-3 | |
| Thu., 10/1 | V Girls Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 10/1 | V Girls Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 10/2 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Sat., 10/3 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:30 p.m. | W 10-0 | |
| Sat., 10/3 | JV Field Hockey | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 9:30 a.m. | ||
| Sat., 10/3 | FR Field Hockey | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 10/3 | V Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 3:00 p.m. | W 7-0 | |
| Sat., 10/3 | JV Girls Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 10/3 | FR Girls Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 10/3 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | Postponed | ||
| Sat., 10/3 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Aux Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | Miscellaneous Events | SAT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Mon., 10/5 | JV Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/5 | V Boys Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/6 | V Boys Cross Country | Westhill | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Westhill | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 10/6 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 10/7 | V Boys Soccer | Wright Tech | Away - Scalzi Park [Directions] | 3:45 p.m. | W 8-1 | |
| Wed., 10/7 | JV Boys Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 8-0 | |
| Thu., 10/8 | FR Football | New Canaan | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Girls Diving | Westhill | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 10/8 | V Girls Volleyball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/9 | V Girls Swimming and Diving | Westhill/Stamford | Home - Darien YMCA [Directions] | 3:00 p.m. | No bus | |
| Sat., 10/10 | V Boys Cross Country | Greenwich | Away - Allen's Meadow-XC Course [Directions] | 11:00 a.m. | ||
| Sat., 10/10 | JV Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 11:00 a.m. | No bus | |
| Sat., 10/10 | FR Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 9:00 a.m. | No bus | |
| Sat., 10/10 | V Girls Cross Country | Greenwich | Away - Allen's Meadow-XC Course [Directions] | 11:15 a.m. | ||
| Sat., 10/10 | V Girls Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 9:50 a.m. | ||
| Sat., 10/10 | JV Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 9:30 a.m. | ||
| Sat., 10/10 | FR Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 10/10 | JV Girls Soccer | Stamford | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 10/10 | JV Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 9:50 a.m. | ||
| Sat., 10/10 | JV Girls Volleyball | Intersquad Game | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | ||
| Mon., 10/12 | V Boys Soccer | Wright Tech | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | W 6-0 | Senior Day |
| Tue., 10/13 | V Boys Cross Country | Stamford | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | Stamford | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | W 3-2 | Senior Day |
| Tue., 10/13 | V Girls Volleyball | Wright Tech | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | Senior Day |
| Wed., 10/14 | V Boys Soccer | Greenwich | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/14 | V Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | W 1-0 | |
| Thu., 10/15 | V Girls Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:10 p.m. | ||
| Thu., 10/15 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 1-0 | |
| Thu., 10/15 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:10 p.m. | ||
| Thu., 10/15 | V Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 10/17 | JV Boys Soccer | Intersquad game Darien JV vs Freshman | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 10/17 | JV Field Hockey | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 10:30 a.m. | ||
| Sat., 10/17 | FR Field Hockey | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 9:00 a.m. | ||
| Sat., 10/17 | JV Girls Soccer | Darien JV vs Darien Freshman (Intersquad) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 10/17 | JV Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 10/17 | FR Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 12:30 p.m. | ||
| Sun., 10/18 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Mon., 10/19 | V Football | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | FR Football | Stamford | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | V Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 10/19 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 10/20 | V Boys Cross Country | Wright Tech | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | Boys Senior Day | |
| Tue., 10/20 | V Girls Cross Country | Wright Tech | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Westhill | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 10/20 | V Girls Swimming and Diving | New Canaan | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/20 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 10/21 | V Boys Soccer | Stamford | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/21 | V Field Hockey | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 10-0 | |
| Wed., 10/21 | V Girls Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/21 | V Girls Swimming and Diving | St. Joseph | Home - Darien YMCA [Directions] | 3:00 p.m. | This is a Virtual Meet | |
| Thu., 10/22 | FR Football | Greenwich | Home - Darien HS-DHS Stadium East [Directions] | 4:30 p.m. | ||
| Fri., 10/23 | V Football | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 10/23 | V Boys Soccer | Westhill | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 10/23 | V Field Hockey | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 10-0 | Senior Day |
| Fri., 10/23 | V Girls Soccer | Stamford | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 10/23 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/23 | V Girls Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 10/24 | JV Boys Soccer | Greenwich | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 10/24 | FR Boys Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 10/24 | JV Girls Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 10/24 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 9:00 a.m. | ||
| Sat., 10/24 | JV Girls Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 10/24 | FR Girls Volleyball | Stamford | Home - Darien HS-DHS South Gym [Directions] | 12:30 p.m. | ||
| Sat., 10/24 | Miscellaneous Events | ACT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Mon., 10/26 | JV Football | Greenwich | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Mon., 10/26 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/27 | V Boys Cross Country | Greenwich | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Girls Cross Country | Greenwich | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/28 | V Boys Soccer | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | L 0-2 | |
| Wed., 10/28 | V Girls Diving | Greenwich | Home - New Canaan YMCA-Pool [Directions] | 5:00 p.m. | ||
| Wed., 10/28 | V Girls Swimming and Diving | Trumbull | Home - Darien YMCA [Directions] | 3:00 p.m. | This is a Virtual Meet | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/31, Time to 8:00 a.m. | ||||||
| Wed., 10/28 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest MS-Pool [Directions] | 3:45 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/31, Time to 8:00 a.m. | ||||||
| Thu., 10/29 | V Girls Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 10/30 | V Football | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | JV Football | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/31 | JV Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | FR Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 12:00 p.m. | ||
| Sat., 10/31 | JV Field Hockey | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 9:30 a.m. | ||
| Sat., 10/31 | FR Field Hockey | Intersquad Darien | Home - Darien HS-DHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 10/31 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 10/31 | JV Girls Soccer | Westhill | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 10/31 | FR Girls Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 11:30 a.m. | ||
| Sat., 10/31 | JV Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:50 a.m. | ||||||
| Sat., 10/31 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 11/2 | V Boys Cross Country | Cross Country Meet FCIAC JV Jamboree #2 @ Allen's Meadows in Wilton | Away - Allen's Meadow | 3:00 p.m. | Postponed from 10/31 | |
| Mon., 11/2 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:00 p.m. | W 4-0 | |
| Mon., 11/2 | V Girls Cross Country | Cross Country Meet FCIAC JV Jamboree #2 @ Allen's Meadows in Wilton | Away - Allen's Meadow | 3:15 p.m. | Postponed from 10/31 | |
| Mon., 11/2 | V Girls Swimming and Diving | Greenwich | Home - Greenwich HS [Directions] | 4:10 p.m. | ||
| Tue., 11/3 | V Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 11/3 | V Girls Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | W 3-2 | |
| Wed., 11/4 | V Boys Cross Country | FCIAC Regional Cross Country Championships @ Waveny Park in New Canaan | Away - Waveny Park | 12:30 p.m. | ||
| Wed., 11/4 | V Girls Cross Country | FCIAC Regional Cross Country Championships @ Waveny Park in New Canaan | Away - Waveny Park | 1:00 p.m. | ||
| Wed., 11/4 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:00 p.m. | L 1-3 | |
| Fri., 11/6 | V Boys Soccer | Westhill | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | ||
| Fri., 11/6 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | W 6-0 | |
| Fri., 11/6 | V Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 3:00 p.m. | W 7-0 | |
| Fri., 11/6 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/6 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 11/7 | JV Boys Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 12:30 p.m. | ||
| Sat., 11/7 | JV Boys Soccer | Greenwich | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 11/7 | FR Boys Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 12:30 p.m. | ||
| Sat., 11/7 | FR Boys Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 11/7 | JV Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | FR Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | JV Girls Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | V Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 2:30 p.m. | W 3-1 | |
| Mon., 11/9 | V Girls Diving | Westhill | Away - Westhill HS-Westhill Pool [Directions] | 3:00 p.m. | ||
| Tue., 11/10 | V Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 11/11 | ||||||
| Wed., 11/11 | V Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 11/11 | V Girls Soccer | Stamford | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | W 5-0 | Early dismissal @ 12:50 p.m. |
| Wed., 11/11 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Wed., 11/11 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 11/12 | V Girls Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 12/5 | Miscellaneous Events | SAT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Wed., 2/3 | JV Boys Squash | vs Greenwich B | Away - Intensity Fitness | 7:15 p.m. | ||
| Wed., 2/3 | V Girls Squash | vs Greenwich | Away - Greenwich Water Club (GWC) | 7:30 p.m. | ||
| Thu., 2/4 | V Boys Squash | vs Greenwich A | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Fri., 2/5 | V Boys Squash | vs Fairfield HS A @ Intensity, Norwalk | Away - Intensity Fitness | 6:30 p.m. | ||
| Sat., 2/6 | Miscellaneous Events | ACT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Sun., 2/7 | JV Boys Squash | vs New Canaan HS | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Tue., 2/9 | V Girls Squash | vs New Canaan A | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Wed., 2/10 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 6:10 p.m. | W 7-4 | |
| Wed., 2/10 | JV Boys Squash | vs New Canaan HS | Away - Intensity Fitness | 7:15 p.m. | ||
| Wed., 2/10 | V Co-ed Alpine Skiing | RACE @ MT. SOUTHINGTON | Home - Mt. Southingon Ski Area [Directions] | 6:00 p.m. | ||
| Thu., 2/11 | JV Boys Ice Hockey | Greenwich | Home - Stamford Twin Rinks-West [Directions] | 3:00 p.m. | ||
| Thu., 2/11 | V Boys Squash | Staples | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Fri., 2/12 | JV Boys Ice Hockey | St. Joseph | Home - Stamford Twin Rinks-West [Directions] | 1:20 p.m. | ||
| Fri., 2/12 | JV Boys Squash | Staples | Away - Intensity Fitness [Directions] | 6:30 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Sat., 2/13 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/13 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | 3:50 p.m. | L 0-3 | |
| Sat., 2/13 | JV Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/13 | FR Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/13 | V Girls Gymnastics | Greenwich | Home - Darien YMCA [Directions] | 2:30 p.m. | 128.2 | |
| Sat., 2/13 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:40 p.m. | W 2-1 | |
| Mon., 2/15 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | L 2-3(OT) | |
| Mon., 2/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 3:25 p.m. | W 9-2 | |
| Tue., 2/16 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks-West [Directions] | 2:30 p.m. | ||
| Tue., 2/16 | JV Girls Squash | Staples | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Wed., 2/17 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 2/17 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | T 4-4(OT) | |
| Wed., 2/17 | V Co-ed Alpine Skiing | RACE @ MT. SOUTHINGTON | Home - Powder Ridge Mountain [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Girls Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 33-26 | |
| Wed., 2/17 | V Girls Gymnastics | Fairfield Ludlowe | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | ||
| Wed., 2/17 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | ||
| Wed., 2/17 | V Girls Squash | vs Greenwich | Away - Greenwich Water Club (GWC) | 7:30 p.m. | ||
| Thu., 2/18 | JV Boys Squash | vs Greenwich B | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Sat., 2/20 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 1:00 p.m. | W 62-55 | |
| Sat., 2/20 | JV Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/20 | FR Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 1:30 p.m. | ||
| Sat., 2/20 | JV Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 a.m. | ||
| Sat., 2/20 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 11:00 a.m. | ||
| Sat., 2/20 | V Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | L 26-60 | |
| Sat., 2/20 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Girls Gymnastics | Fairfield Warde | Home - Darien YMCA [Directions] | 2:30 p.m. | 122.75 | This Virtual meet corresponds with Fairfield Warde/Ludlowe competing on 2/17 at 6:30 p.m. at GCA |
| Sat., 2/20 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | W 8-0 | |
| Sun., 2/21 | JV Girls Squash | Staples | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Mon., 2/22 | V Boys Diving | Fairfield Ludlowe | Home - New Canaan YMCA-Pool [Directions] | 7:40 p.m. | ||
| Tue., 2/23 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | L 63-54 | |
| Tue., 2/23 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Tue., 2/23 | V Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | L 32-51 | |
| Tue., 2/23 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:00 p.m. | ||
| Tue., 2/23 | V Girls Squash | Staples | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Wed., 2/24 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/24 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 2/24 | JV Boys Squash | vs Fairfield HS B | Away - Intensity Fitness | 7:15 p.m. | ||
| Wed., 2/24 | V Co-ed Alpine Skiing | RACE @ MT. SOUTHINGTON | Home - Mt. Southingon Ski Area [Directions] | 5:00 p.m. | ||
| Wed., 2/24 | JV Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/24 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice House-Ice Rink [Directions] | 6:10 p.m. | W 9-0 | |
| Thu., 2/25 | V Boys Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 42-40 | |
| Thu., 2/25 | V Boys Diving | vs New Canaan HS | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 2/25 | JV Boys Squash | Staples | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Thu., 2/25 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:00 p.m. | W 38-35 | |
| Thu., 2/25 | V Sideline Cheerleading | @ Boys Varsity Basketball game vs Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/26 | JV Boys Ice Hockey | St. Lukes | Away - Sono Ice House-Main Rink | 3:05 p.m. | ||
| Sat., 2/27 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 3:00 p.m. | L 55-51 | |
| Sat., 2/27 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 2:00 p.m. | ||
| Sat., 2/27 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 11:00 a.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | W 5-1 | |
| Sat., 2/27 | V Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 12:30 p.m. | W 29-26 | |
| Sat., 2/27 | JV Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/27 | FR Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/27 | V Girls Gymnastics | Staples | Home - Darien YMCA [Directions] | 2:30 p.m. | 124.6 | This Virtual meet corresponds to Staples competing on 2/26 at 4:30 p.m. at Westport YMCA |
| Sat., 2/27 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | W 9-1 | |
| Sun., 2/28 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 12:30 p.m. | W 50-49 | |
| Sun., 2/28 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 5:20 p.m. | ||
| Sun., 2/28 | V Boys Squash | vs New Canaan HS | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Mon., 3/1 | V Boys Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Tue., 3/2 | V Boys Basketball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 5:00 p.m. | L 43-52 | |
| Tue., 3/2 | V Boys Squash | vs New Canaan HS | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Tue., 3/2 | V Girls Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | L 23-27 | |
| Tue., 3/2 | V Girls Gymnastics | Wilton | Away - Wilton HS-Aux Gym [Directions] | 6:00 p.m. | 136.85 | |
| Tue., 3/2 | V Girls Gymnastics | Westhill | Away - Chelsea Piers - Stamford-Virtual Meet [Directions] | 7:30 p.m. | ||
| Tue., 3/2 | V Girls Gymnastics | Stamford | Away - Chelsea Piers-Virtual Meet [Directions] | 7:30 p.m. | ||
| Wed., 3/3 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:00 p.m. | L 49-68 | |
| Wed., 3/3 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | ||
| Wed., 3/3 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 8:00 p.m. | L 3-4 | |
| Wed., 3/3 | JV Boys Ice Hockey | St. Joseph | Home - Stamford Twin Rinks-West [Directions] | 3:15 p.m. | ||
| Wed., 3/3 | V Co-ed Alpine Skiing | RACE @ MT. SOUTHINGTON | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | ||
| Wed., 3/3 | V Girls Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 37-18 | |
| Wed., 3/3 | JV Girls Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 3/3 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 7-1 | |
| Wed., 3/3 | V Girls Indoor Track | Wilton | Home - Darien HS-DHS Track [Directions] | 3:00 p.m. | ||
| Thu., 3/4 | V Boys Squash | vs Fairfield HS A | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Fri., 3/5 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:00 p.m. | L 57-66 | |
| Fri., 3/5 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 3/5 | V Girls Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | L 22-52 | |
| Fri., 3/5 | V Sideline Cheerleading | @ Girls Varsity Basketball game vs Ridgefield | Home - Darien HS-DHS Track [Directions] | 4:30 p.m. | ||
| Fri., 3/5 | V Girls Gymnastics | New Canaan | Away - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Sat., 3/6 | JV Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 3/6 | FR Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 3/6 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | T 2-2(OT) | |
| Sat., 3/6 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 3/6 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 3/6 | V Girls Gymnastics | Westhill | Home - Darien YMCA [Directions] | 2:30 p.m. | 127.55 | This Virtual meet corresponds with Westhill/Stamford competing on 3/2 @ 7:00 p.m. at Chelsea Piers |
| Sat., 3/6 | V Girls Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | L 4-3 | |
| Sun., 3/7 | V Girls Indoor Track | Bethel | Away - Bethel Berry School- Kisling Field [Directions] | 5:00 p.m. | ||
| Sun., 3/7 | JV Girls Squash | Staples | Home - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Mon., 3/8 | V Boys Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | L 42-51 | |
| Mon., 3/8 | JV Boys Ice Hockey | Ridgefield | Home - Stamford Twin Rinks-West [Directions] | 4:00 p.m. | ||
| Mon., 3/8 | V Co-ed Alpine Skiing | RACE @ MT. SOUTHINGTON | Home - Mt. Southingon Ski Area [Directions] | 5:00 p.m. | ||
| Mon., 3/8 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | L 33-50 | |
| Tue., 3/9 | V Boys Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 61-50 | |
| Tue., 3/9 | V Boys Ice Hockey | Greenwich | Away - DontUse-Dorothy Hamill Ice Rink-Dorothy Hamill Ice Rink [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 3/9 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks-West [Directions] | 3:00 p.m. | ||
| Tue., 3/9 | V Boys Outdoor Track | Greenwich (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Tue., 3/9 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | L 1-0 | |
| Wed., 3/10 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 3/10 | V Boys Diving | Wilton | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 3/10 | JV Girls Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 3/10 | V Girls Indoor Track | New Canaan | Home - Darien HS-DHS Track [Directions] | 3:00 p.m. | ||
| Thu., 3/11 | V Boys Basketball | Harding | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 60-56 | |
| Thu., 3/11 | V Boys Swimming and Diving | Wilton | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 3/11 | V Girls Basketball | Harding | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | Cancelled | |
| Thu., 3/11 | V Sideline Cheerleading | @ Boys Varsity Basketball game vs Warren Harding | Home - Darien HS-DHS Track [Directions] | 4:30 p.m. | ||
| Fri., 3/12 | V Boys Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | L 41-43 | |
| Fri., 3/12 | JV Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Fri., 3/12 | JV Boys Squash | Staples | Away - Intensity Fitness [Directions] | 6:30 p.m. | ||
| Fri., 3/12 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 19-54 | |
| Fri., 3/12 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | T 1-1(OT) | |
| Sat., 3/13 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 3/13 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 3/13 | V Boys Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 8:10 p.m. | W 4-1 | |
| Sat., 3/13 | V Girls Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | W 39-35 | |
| Sat., 3/13 | JV Girls Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/13 | FR Girls Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 3/13 | V Girls Gymnastics | Trumbull | Home - Darien YMCA [Directions] | 2:30 p.m. | 125.85 | This Virtual Meet corresponds to Trumbull/St. Joes competing on 3/14 at 1:00 p.m. @ Next Dimensions |
| Sat., 3/13 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Stamford Twin Rinks-East [Directions] | 4:10 p.m. | W 9-0 | |
| Sun., 3/14 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 1:00 p.m. | ||
| Sun., 3/14 | V Girls Gymnastics | St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 1:00 p.m. | ||
| Mon., 3/15 | V Co-ed Alpine Skiing | States | Away - Mt. Southingon Ski Area | 4:00 p.m. | ||
| Mon., 3/15 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:00 p.m. | L 37-41 | |
| Mon., 3/15 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 9-0 | |
| Mon., 3/15 | V Girls Indoor Track | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Tue., 3/16 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | W 51-40 | |
| Wed., 3/17 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 3:50 p.m. | W 5-0 | |
| Wed., 3/17 | V Boys Indoor Track | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 3/17 | V Boys Squash | vs Fairfield HS A | Home - Ox Ridge Club [Directions] | 7:15 p.m. | ||
| Wed., 3/17 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 5:00 p.m. | L 30-36 | |
| Thu., 3/18 | JV Girls Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 3/18 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 3/18 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 4:45 p.m. | W 4-2 | |
| Fri., 3/19 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L ?? | |
| Sat., 3/20 | JV Boys Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 3/20 | FR Boys Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 3/20 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:15 p.m. | W 7-2 | |
| Sat., 3/20 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 3/20 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/20 | V Girls Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | ||
| Tue., 3/23 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Thu., 3/25 | V Boys Diving | FCIAC Diving @ Greenwich | Away - Greenwich HS | 5:00 p.m. | ||
| Thu., 3/25 | V Boys Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | L 1-2 | |
| Wed., 3/31 | V Boys Lacrosse | Brunswick School (Scrim.) | Away - Brunswick Cosby Turf Field | 5:00 p.m. | ||
| Wed., 3/31 | V Co-ed Sailing | Brunswick School | Away - Indian Harbor Yacht Club | 4:00 p.m. | ||
| Thu., 4/1 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 3:30 p.m. | ||
| Sat., 4/3 | V Baseball | New Fairfield (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 9:00 a.m. | ||
| Sat., 4/3 | JV Baseball | New Fairfield (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 9:00 a.m. | ||
| Sat., 4/3 | V Boys Lacrosse | Wilton (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 4/3 | JV Boys Lacrosse | Wilton (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 4/3 | V Softball | Stamford (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 4/3 | V Softball | Stamford (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 2:00 p.m. | ||
| Mon., 4/5 | V Co-ed Sailing | Brunswick School | Away - Indian Harbor Yacht Club | Postponed | ||
| Tue., 4/6 | V Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:45 p.m. | ||
| Tue., 4/6 | JV Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 3:45 p.m. | ||
| Tue., 4/6 | V Softball | Greenwich (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 3:45 p.m. | ||
| Wed., 4/7 | V Boys Lacrosse | TBA | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 4/7 | V Co-ed Sailing | Fairfield Ludlowe | Away - Pequot Yacht Club [Directions] | 4:00 p.m. | ||
| Thu., 4/8 | V Girls Lacrosse | Convent of Sacred Heart (Scrim.) | Away - CSH Grass Lacrosse Field-Stadium | 4:30 p.m. | ||
| Thu., 4/8 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 3:30 p.m. | ||
| Sat., 4/10 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | L 0-6 | |
| Sat., 4/10 | JV Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 9:30 a.m. | ||
| Sat., 4/10 | FR Baseball | Danbury | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 4/10 | FR Baseball | Danbury | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 2:00 p.m. | ||
| Sat., 4/10 | V Boys Tennis | Norwalk | Home - Darien HS-DHS Tennis Courts [Directions] | 10:00 a.m. | W 5-2 [Detailed Results] | |
| Sat., 4/10 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 4/10 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 1:00 p.m. | ||
| Sat., 4/10 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | 2:00 p.m. | L 2-14 | |
| Sat., 4/10 | JV Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 4/10 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 10:00 a.m. | W 7-0 | |
| Mon., 4/12 | JV Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | ||
| Mon., 4/12 | V Boys Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 4/13 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | W 24-1 | |
| Tue., 4/13 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Tue., 4/13 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/13 | JV Boys Tennis | Trumbull | Away - Unity Park [Directions] | 4:00 p.m. | ||
| Tue., 4/13 | V Girls Lacrosse | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 21-2 | |
| Tue., 4/13 | V Softball | Brien McMahon | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | W 11-4 | |
| Tue., 4/13 | V Girls Tennis | Trumbull | Home - Darien HS-DHS Tennis Courts [Directions] | 10:00 a.m. | W 7-0 | |
| Tue., 4/13 | JV Girls Tennis | Trumbull | Home - Weed Beach Tennis Courts [Directions] | 10:00 a.m. | ||
| Wed., 4/14 | V Baseball | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | L 4-9 | |
| Wed., 4/14 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/14 | FR Boys Lacrosse | Fairfield Prep (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/14 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Wed., 4/14 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/14 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/14 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 5-1 | |
| Wed., 4/14 | V Girls Tennis | Westhill | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 4/15 | JV Boys Tennis | Fairfield Ludlowe | Home - Weed Beach Tennis Courts [Directions] | Postponed | ||
| Fri., 4/16 | V Baseball | Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 17-9 | |
| Fri., 4/16 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Fri., 4/16 | V Boys Lacrosse | Glastonbury | Home - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | W 19-5 | |
| Fri., 4/16 | JV Boys Lacrosse | Glastonbury | Home - Darien HS-DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Fri., 4/16 | FR Boys Lacrosse | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Fri., 4/16 | FR Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Fri., 4/16 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | W 10-5 | |
| Fri., 4/16 | V Softball | Greenwich | Away - Bruce Park Field [Directions] | 4:00 p.m. | W 17-5 | |
| Fri., 4/16 | JV Softball | Greenwich | Home - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Sat., 4/17 | FR Baseball | Ridgefield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 4/17 | FR Baseball | Ridgefield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 4/17 | JV Softball | Wilton | Home - Darien HS-DHS - Softball - JV Field [Directions] | 10:00 a.m. | ||
| Mon., 4/19 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 7-8 | |
| Mon., 4/19 | JV Baseball | Westhill | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/19 | JV Boys Golf | New Canaan | Away - New Canaan HS-CCNC [Directions] | 3:15 p.m. | ||
| Mon., 4/19 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/19 | V Girls Lacrosse | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 14-7 | |
| Mon., 4/19 | V Softball | Westhill | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 4/19 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 4/19 | V Girls Tennis | Brien McMahon | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/20 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Darien 152 Westhill 185 | |
| Tue., 4/20 | JV Boys Golf | Wilton | Home - Country Club of Darien [Directions] | 3:30 p.m. | ||
| Tue., 4/20 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | W 14-7 | |
| Tue., 4/20 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/20 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Boys Tennis | Bridgeport Central | Home - Darien HS-DHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/20 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 4/20 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 4/20 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/21 | JV Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | Canceled | Cancelled | |
| Wed., 4/21 | JV Softball | Norwalk | Home - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Thu., 4/22 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:30 p.m. | ||
| Thu., 4/22 | V Boys Golf | Fairfield Warde | Home - Woodway Country Club [Directions] | 3:15 p.m. | Darien 177 Warde 179 Woodway - BLUE Tees | |
| Thu., 4/22 | FR Boys Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:30 p.m. | ||
| Thu., 4/22 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/22 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/22 | V Girls Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | Darien 214 Staples 210 | |
| Thu., 4/22 | JV Girls Golf | Staples | Away - Longshore Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 4/22 | V Girls Indoor Track | Greenwich Academy | Home - Darien HS-DHS Track [Directions] | 3:00 p.m. | ||
| Thu., 4/22 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 7-5 | |
| Thu., 4/22 | V Girls Rugby | Greenwich | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 4/22 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 4:15 p.m. | W 12-8 | |
| Thu., 4/22 | V Girls Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 4/22 | JV Girls Tennis | Staples | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-9 | |
| Fri., 4/23 | JV Baseball | St. Joseph | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | FR Boys Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | V Boys Rugby | Greenwich | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | V Boys Tennis | Fairfield Ludlowe | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/23 | V Softball | St. Joseph | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 16-0 | |
| Fri., 4/23 | JV Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Sat., 4/24 | V Baseball | Norwalk | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:00 p.m. | L 9-15 | |
| Sat., 4/24 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 10:30 a.m. | ||
| Sat., 4/24 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 12:30 p.m. | ||
| Sat., 4/24 | V Boys Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | W 15-6 | |
| Sat., 4/24 | JV Boys Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | Postponed | ||
| Sat., 4/24 | V Boys Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 4/24 | JV Boys Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 4/24 | JV Softball | Westhill | Home - Darien HS-DHS - Softball - JV Field [Directions] | 10:00 a.m. | ||
| Sat., 4/24 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 2:00 p.m. | L 3-4 | |
| Mon., 4/26 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | L 9-20 | |
| Mon., 4/26 | JV Baseball | Ridgefield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/26 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Darien 163 Danbury 215 | |
| Mon., 4/26 | FR Boys Lacrosse | St. Joseph | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/26 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | W 5-2 [Detailed Results] | |
| Mon., 4/26 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Mon., 4/26 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/26 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/26 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Darien 227 Trumbull 205 | |
| Mon., 4/26 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 4/26 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | W 18-3 | |
| Mon., 4/26 | V Girls Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/26 | V Softball | Ridgefield | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | W 8-7 | |
| Mon., 4/26 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Field [Directions] | Canceled | Cancelled | |
| Mon., 4/26 | V Girls Tennis | Greenwich | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/26 | JV Girls Tennis | Greenwich | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | JV Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 4/27 | V Boys Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Boys Tennis | Danbury | Home - Darien HS-DHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/27 | V Girls Golf | Danbury | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 212 Danbury 250 | |
| Tue., 4/27 | JV Girls Golf | Danbury | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 4/27 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/27 | JV Girls Tennis | Weston | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Baseball | Trumbull | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 6-10 | |
| Wed., 4/28 | V Boys Golf | Wilton | Home - Woodway Country Club [Directions] | 3:15 p.m. | Darien 167 Wilton 178 Woodway - BLUE Tees | |
| Wed., 4/28 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/28 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 4/28 | JV Boys Tennis | Weston | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Co-ed Sailing | Staples | Away - Pequot Yacht Club [Directions] | 3:45 p.m. | ||
| Wed., 4/28 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | Darien 224 Ludlowe 188 | |
| Wed., 4/28 | V Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-Stadium | 4:00 p.m. | W 15-5 | |
| Wed., 4/28 | JV Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-Turf field | 5:30 p.m. | ||
| Wed., 4/28 | JV Softball | Trumbull | Home - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Thu., 4/29 | V Boys Golf | Norwalk | Home - Woodway Country Club [Directions] | 3:15 p.m. | Darien 154 Norwalk 183 Woodway - WHITE tees | |
| Thu., 4/29 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | W 10-7 | |
| Thu., 4/29 | JV Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Thu., 4/29 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 4/29 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 4/29 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:15 p.m. | Darien 200 Wilton NS | |
| Fri., 4/30 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:30 p.m. | L 3-4 | |
| Fri., 4/30 | JV Baseball | Brien McMahon | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Boys Outdoor Track | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Boys Tennis | St. Joseph | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/30 | V Boys Volleyball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/30 | JV Boys Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 4/30 | V Girls Lacrosse | Staples | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 16-8 | |
| Fri., 4/30 | V Girls Outdoor Track | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Softball | Brien McMahon | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 12-0 | |
| Fri., 4/30 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Sat., 5/1 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/1 | FR Baseball | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 5/1 | FR Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 5/1 | V Boys Lacrosse | Brunswick School | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | L 9-8 | |
| Sat., 5/1 | JV Boys Lacrosse | Brunswick School | Home - Darien HS-DHS Stadium Field [Directions] | 10:30 a.m. | ||
| Sat., 5/1 | V Boys Rugby | Notre Dame-Fairfield | Away - Holden Field-Simsbury 2 [Directions] | 2:15 p.m. | ||
| Sat., 5/1 | JV Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 2:00 p.m. | ||
| Sat., 5/1 | JV Boys Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Sat., 5/1 | V Boys Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 5/1 | JV Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 10:00 a.m. | No bus needed | |
| Sun., 5/2 | V Co-ed Sailing | Regatta @ Pequot YC | Away - Pequot Yacht Club | 10:00 a.m. | ||
| Mon., 5/3 | V Baseball | Fairfield Warde | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 2-13 | |
| Mon., 5/3 | JV Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/3 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Darien 169 Trumbull 177 | |
| Mon., 5/3 | JV Boys Golf | Trumbull | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Mon., 5/3 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/3 | V Boys Tennis | New Canaan | Home - Darien HS-DHS Tennis Courts [Directions] | 4:30 p.m. | W 6-0 | |
| Mon., 5/3 | JV Boys Tennis | New Canaan | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/3 | V Boys Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/3 | JV Boys Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/3 | V Girls Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 9-10 | |
| Mon., 5/3 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | L 3-2 | |
| Mon., 5/3 | JV Softball | Fairfield Warde | Home - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Mon., 5/3 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/4 | V Baseball | Fairfield Warde | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | Darien 163 Ridgefield 163 | |
| Tue., 5/4 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/4 | V Boys Lacrosse | Fairfield Warde | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 20-4 | |
| Tue., 5/4 | JV Boys Lacrosse | Fairfield Warde | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 5/4 | V Boys Outdoor Track | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/4 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Girls Golf | Ridgefield | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 218 Ridgefield 214 | |
| Tue., 5/4 | JV Girls Golf | Ridgefield | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 5/4 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 20-0 | |
| Tue., 5/4 | V Girls Outdoor Track | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Girls Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/4 | JV Girls Tennis | Ridgefield | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/5 | V Boys Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | W 20-6 | |
| Wed., 5/5 | V Girls Golf | Greenwich | Home - Woodway Country Club [Directions] | 3:00 p.m. | Darien 215 Greenwich 197 | |
| Wed., 5/5 | JV Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | Canceled | Cancelled | |
| Wed., 5/5 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/6 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | L 8-9 | |
| Thu., 5/6 | JV Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/6 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 23-1 | |
| Thu., 5/6 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Thu., 5/6 | V Boys Tennis | Stamford | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/6 | V Boys Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 5/6 | JV Boys Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/6 | V Co-ed Sailing | Regatta @ Grass Island v Greenwich HS, GFA and Fairfield Prep | Away - Grass Island | 4:00 p.m. | ||
| Thu., 5/6 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:15 p.m. | Darien 201 Wilton 227 | |
| Thu., 5/6 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/6 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Thu., 5/6 | V Girls Lacrosse | Norwalk | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 20-1 | |
| Thu., 5/6 | V Girls Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Thu., 5/6 | V Girls Rugby | North Haven | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 5/6 | V Softball | Fairfield Ludlowe | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 16-3 | |
| Fri., 5/7 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 5/7 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Canceled | Cancelled | |
| Fri., 5/7 | V Softball | Harding | Away - Warren Harding HS-Luis Munoz Marin School-Boston Ave/Pembroke St. [Directions] | 4:00 p.m. | W 21-1 | |
| Fri., 5/7 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:15 p.m. | ||
| Sat., 5/8 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 11:30 a.m. | ||
| Sat., 5/8 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 9:30 a.m. | ||
| Sat., 5/8 | V Boys Lacrosse | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | W 15-11 | |
| Sat., 5/8 | JV Boys Lacrosse | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Sat., 5/8 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 5/8 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 11:30 a.m. | ||
| Sat., 5/8 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 3:00 p.m. | L 3-1 | |
| Sat., 5/8 | JV Softball | Harding | Home - Darien HS-DHS Softball - Varsity Field [Directions] | Postponed | ||
| Sat., 5/8 | Miscellaneous Events | SAT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Mon., 5/10 | JV Baseball | Danbury | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Boys Golf | Fairfield Prep | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 165 Fairfield Prep 170 | |
| Mon., 5/10 | JV Boys Lacrosse | Staples | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 5:45 p.m. | ||
| Mon., 5/10 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Mon., 5/10 | V Boys Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 4:30 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/10 | V Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 5/10 | JV Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Girls Golf | Fairfield Warde | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 207 Warde 198 | |
| Mon., 5/10 | V Girls Outdoor Track | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Softball | Danbury | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 6-4 | |
| Mon., 5/10 | JV Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | Canceled | Cancelled | |
| Mon., 5/10 | V Girls Tennis | Wilton | Away - Wilton HS-Wilton Varsity Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/10 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/11 | V Baseball | Harding | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 20-2 | |
| Tue., 5/11 | FR Baseball | Greenwich | Home - Darien HS-Town Hall Baseball Field [Directions] | 4:00 p.m. | Address- 2 Renshaw Rd, Darien | |
| Tue., 5/11 | V Boys Golf | Stamford | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 161 Stamford 254 | |
| Tue., 5/11 | V Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 4:00 p.m. | W 24-2 | |
| Tue., 5/11 | JV Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:30 p.m. | ||
| Tue., 5/11 | V Boys Outdoor Track | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/11 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Tue., 5/11 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Tue., 5/11 | V Co-ed Sailing | Fairfield County Sailing League Silver Cup | Away - Grass Island | 4:00 p.m. | ||
| Tue., 5/11 | V Girls Golf | St. Joseph | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 232 St. Joseph 207 | |
| Tue., 5/11 | V Girls Lacrosse | Stamford | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 20-3 | |
| Tue., 5/11 | V Girls Tennis | Fairfield Warde | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/11 | JV Girls Tennis | Fairfield Warde | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/12 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 3-13 | |
| Wed., 5/12 | JV Baseball | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/12 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:15 p.m. | Darien 163 McMahon 188 | |
| Wed., 5/12 | JV Boys Golf | Fairfield Prep | Away - Patterson Club [Directions] | 3:00 p.m. | ||
| Wed., 5/12 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Wed., 5/12 | V Boys Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | ||
| Wed., 5/12 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/12 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/12 | V Co-ed Sailing | Gold Cup @ Grass Island- need to qualify based on results of 5/11 | Away - Grass Island | Canceled | Cancelled | |
| Wed., 5/12 | V Girls Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | ||
| Wed., 5/12 | V Softball | New Canaan | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 8-1 | |
| Thu., 5/13 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:30 p.m. | W 26-5 | |
| Thu., 5/13 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | Darien 153 Staples 150 | |
| Thu., 5/13 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/13 | V Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | W 15-9 | |
| Thu., 5/13 | JV Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Center Oval Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 5/13 | V Boys Tennis | Norwalk | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-0 | |
| Thu., 5/13 | V Girls Golf | New Canaan | Home - Woodway Country Club [Directions] | 3:00 p.m. | Darien 222 New Canaan 168 | |
| Thu., 5/13 | JV Girls Golf | New Canaan | Home - Woodway Country Club [Directions] | 3:30 p.m. | ||
| Thu., 5/13 | V Girls Lacrosse | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 14-3 | |
| Thu., 5/13 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | FR Boys Lacrosse | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 5/14 | V Boys Rugby | Staples | Home - Royle School Field [Directions] | Canceled | Cancelled | |
| Fri., 5/14 | JV Boys Rugby | Staples | Home - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 16-4 | |
| Fri., 5/14 | V Girls Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | Cancelled | |
| Fri., 5/14 | V Girls Tennis | Bridgeport Central | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/15 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 10:00 a.m. | L 4-5 | |
| Sat., 5/15 | FR Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 5/15 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 1:00 p.m. | W 12-7 | |
| Sat., 5/15 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 10:30 a.m. | ||
| Sat., 5/15 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 10:00 a.m. | ||
| Sat., 5/15 | JV Boys Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 11:00 a.m. | ||
| Sat., 5/15 | V Boys Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 5/15 | JV Boys Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 5/15 | V Girls Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | Canceled | Cancelled | |
| Sat., 5/15 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 11:00 a.m. | ||
| Sat., 5/15 | JV Girls Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 2:00 p.m. | ||
| Sun., 5/16 | V Co-ed Sailing | CT State Co-Ed Fleet Race Championships- Black Rock or Grass Island | Away - Grass Island | 10:00 a.m. | ||
| Mon., 5/17 | V Baseball | Stamford | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | W 7-3 | |
| Mon., 5/17 | JV Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | V Boys Golf | New Canaan | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 162 New Canaan 160 | |
| Mon., 5/17 | FR Boys Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | V Boys Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | V Girls Golf | Fairfield Ludlowe | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 222 Ludlowe 198 | |
| Mon., 5/17 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | L 6-0 | |
| Mon., 5/17 | JV Softball | Stamford | Home - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Tue., 5/18 | FR Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Darien 161 St. Joe 157 | |
| Tue., 5/18 | V Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | W 16-9 | |
| Tue., 5/18 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Boys Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 5/18 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | W 19-7 | |
| Tue., 5/18 | V Girls Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Wed., 5/19 | V Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 0-4 | |
| Wed., 5/19 | JV Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/19 | FR Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 5/19 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 2:40 p.m. | Darien 223 St Joseph 182 | |
| Wed., 5/19 | JV Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 2:40 p.m. | ||
| Wed., 5/19 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/19 | V Softball | Staples | Away - Greens Farms Elementary School-Softball Field [Directions] | 7:00 p.m. | L 5-4 | |
| Wed., 5/19 | JV Softball | Staples | Home - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Wed., 5/19 | V Girls Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/20 | V Boys Golf | Fairfield Ludlowe | Home - Woodway Country Club [Directions] | 3:15 p.m. | Darien 158 Ludlowe 166 | |
| Thu., 5/20 | JV Boys Golf | Greenwich | Home - Woodway Country Club [Directions] | 3:15 p.m. | ||
| Thu., 5/20 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | W 10-9 | |
| Thu., 5/20 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 6:30 p.m. | ||
| Thu., 5/20 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/20 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/20 | V Boys Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/20 | V Boys Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 5/20 | JV Boys Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/20 | V Girls Golf | New Canaan | Away - New Canaan HS-CCNC [Directions] | 3:30 p.m. | Darien 238 Nyc 169 | |
| Thu., 5/20 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/20 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Thu., 5/20 | V Girls Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 19-2 | |
| Thu., 5/20 | V Girls Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | Canceled | Cancelled | |
| Fri., 5/21 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/21 | FR Boys Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/21 | V Boys Rugby | Fairfield Prep | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Fri., 5/21 | V Boys Volleyball | TBA | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 5/21 | V Softball | Ridgefield | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 1:00 p.m. | W 5-0 | |
| Fri., 5/21 | V Girls Tennis | Westhill | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/22 | FR Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 5/22 | FR Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 5/22 | V Boys Lacrosse | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | W 21-4 | |
| Sat., 5/22 | JV Boys Lacrosse | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 10:30 a.m. | ||
| Sun., 5/23 | V Co-ed Sailing | CT State Women's Championship | Away - Grass Island | 9:00 a.m. | ||
| Mon., 5/24 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/24 | V Boys Lacrosse | Trumbull | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | W 20-6 | |
| Mon., 5/24 | V Boys Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/24 | V Girls Outdoor Track | Girls Outdoor Track FCIAC Championshiop | Away - Danbury HS-Danbury HS Stadium | 4:00 p.m. | ||
| Tue., 5/25 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Tue., 5/25 | FR Boys Lacrosse | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Tue., 5/25 | V Boys Outdoor Track | Boys Outdoor Track FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 4:00 p.m. | ||
| Tue., 5/25 | V Boys Tennis | Staples | Away - Wilton HS-Wilton HS tennis courts [Directions] | 4:00 p.m. | ||
| Tue., 5/25 | V Girls Golf | Staples | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 219 Staples 187 | |
| Wed., 5/26 | V Boys Golf | Greenwich | Home - Wee Burn CC [Directions] | 3:30 p.m. | Darien 157 Greenwich 164 | |
| Wed., 5/26 | V Boys Lacrosse | Ridgefield | Home - Darien HS [Directions] | 5:00 p.m. | W 16-9 | |
| Wed., 5/26 | V Boys Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/26 | JV Girls Golf | Ekstrom JV Girls Golf Tourney @ Par 3 in Fairfield | Away - Carl Dickman Par 3 | 3:15 p.m. | ||
| Wed., 5/26 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 3:30 p.m. | ||
| Thu., 5/27 | V Baseball | Fairfield Warde | Away - Cubeta Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/27 | V Boys Golf | CHAPPA @ Longshore | Away - Longshore Golf Course | 3:15 p.m. | ||
| Thu., 5/27 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 5/27 | JV Girls Golf | New Canaan | Away - CCNC [Directions] | 3:00 p.m. | ||
| Thu., 5/27 | V Girls Rugby | Southington | Home - Royle School Field [Directions] | Canceled | Cancelled | |
| Thu., 5/27 | V Girls Tennis | Staples | Away - Wilton HS-Wilton HS tennis courts [Directions] | 5:00 p.m. | ||
| Fri., 5/28 | V Boys Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | W 15-3 | |
| Fri., 5/28 | JV Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:00 p.m. | ||
| Fri., 5/28 | V Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 5/29 | V Girls Tennis | East Hartford | Home - Solaris Racquet Club [Directions] | 2:00 p.m. | ||
| Sun., 5/30 | V Softball | Stamford (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 12:00 p.m. | Cancelled | |
| Tue., 6/1 | V Baseball | Hamden | Away - Hamden HS-HHS Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 6/1 | V Boys Golf | Holahan Invitational @ CCD | Home - Country Club of Darien [Directions] | 12:00 p.m. | ||
| Tue., 6/1 | V Boys Outdoor Track | CIAC Class L Boys Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/1 | V Boys Tennis | South Windsor | Home - Darien HS-DHS Tennis Courts [Directions] | 1:00 p.m. | ||
| Tue., 6/1 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | Darien 199 Warde 209 | |
| Tue., 6/1 | V Girls Outdoor Track | CIAC Class L Girls Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/1 | V Softball | South Windsor | Away - South Windsor HS-Varsity Softball Diamond Ayers Road [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 6/1 | V Girls Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/2 | V Boys Golf | FCIAC Championship- Fairchild Wheeler | Away - Fairchild Wheeler Golf Course | 3:20 p.m. | ||
| Wed., 6/2 | V Boys Lacrosse | Glastonbury | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Wed., 6/2 | V Boys Tennis | New Canaan | Home - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/2 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | L 4-3 | |
| Thu., 6/3 | V Boys Golf | FCIACS @ Fairchild Wheeler | Away - Fairchild Wheeler Golf Course | 12:00 p.m. | ||
| Thu., 6/3 | V Boys Tennis | Wilton | Away - East Hartford Tennis Club [Directions] | 10:00 a.m. | ||
| Thu., 6/3 | V Girls Golf | FCIACS @ Fairchild Wheeler | Away - Fairchild Wheeler Golf Course | TBA | ||
| Thu., 6/3 | V Girls Rugby | Staples | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Fri., 6/4 | V Boys Volleyball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 6/5 | V Boys Lacrosse | Fairfield Prep | Home - Darien HS-DHS Stadium Field [Directions] | 2:30 p.m. | ||
| Sat., 6/5 | Miscellaneous Events | SAT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Mon., 6/7 | V Boys Golf | State Tournament @ Tallwood Golf Course | Away - Tallwood Country Club | 7:30 a.m. | ||
| Mon., 6/7 | V Boys Golf | CIAC Boys Div. I Golf Championship | Away - Tallwood CC | 8:00 a.m. | ||
| Tue., 6/8 | V Boys Volleyball | Trumbull | Home - Shelton HS-Murray Gymnasium [Directions] | 7:00 p.m. | ||
| Tue., 6/8 | V Girls Golf | States | Away - Grassy Hill Country Club | 8:30 a.m. | ||
| Wed., 6/9 | V Boys Outdoor Track | CIAC Open Boys Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Wed., 6/9 | V Girls Golf | CIAC Girls Div. I Golf Championship | Away - Grassy Hill | 8:30 a.m. | ||
| Wed., 6/9 | V Girls Outdoor Track | CIAC Open Girls Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Thu., 6/10 | V Boys Volleyball | Enfield | Home - Xavier HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 6/12 | V Boys Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/12 | V Girls Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/12 | Miscellaneous Events | ACT Test @ DHS | Home - Darien HS-TBA [Directions] | TBA | ||
| Sun., 6/13 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 5:00 p.m. | ||
| Mon., 6/14 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Mon., 6/14 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Tue., 6/15 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 1 | Away - Manchester | 10:00 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 1 | Away - Manchester | 10:30 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||