| Darien 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1115 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 8/25 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Darien 161 Trumbull 168 | |
| Thu., 8/25 | JV Boys Golf | Trumbull | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Sat., 8/27 | V Football | Cheshire, Simsbury (Scrim.) | Away - Cheshire High Main Game field [Directions] | 9:00 a.m. | ||
| Sat., 8/27 | FR Football | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 9:00 a.m. | ||
| Sun., 8/28 | V Field Hockey | Ridgefield (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Mon., 8/29 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Darien 164 Stamford 205 | |
| Tue., 8/30 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Tue., 8/30 | V Field Hockey | Norwalk (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 8/30 | V Girls Soccer | Southington (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 8/30 | JV Girls Soccer | Southington (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 8/31 | V Boys Golf | Westhill | Home - Woodway Country Club [Directions] | 3:15 p.m. | Darien 178 Westhill 180 | |
| Wed., 8/31 | V Boys Soccer | St. Lukes (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 8/31 | JV Boys Soccer | St. Lukes (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Darien 171 Warde 152 | |
| Thu., 9/1 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:00 p.m. | ||
| Thu., 9/1 | V Girls Volleyball | John Jay (NY) (Scrim.) | Away - John Jay HS (Crossriver) | 4:30 p.m. | ||
| Thu., 9/1 | JV Girls Volleyball | John Jay (NY) (Scrim.) | Away - John Jay HS (Crossriver) | TBA | ||
| Fri., 9/2 | V Football | Fairfield Prep (Scrim.) | Away - Fairfield University-Barlow Field [Directions] | 4:00 p.m. | ||
| Fri., 9/2 | FR Football | Fairfield Prep (Scrim.) | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Fri., 9/2 | V Boys Soccer | Bassick (Scrim.) | Away - Bassick HS-Knight Stadium UB [Directions] | 5:00 p.m. | ||
| Sat., 9/3 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 9:00 a.m. | ||
| Sat., 9/3 | V Girls Volleyball | Bristol Eastern, Conard, East Lyme, Farmington, Foran, Southington | Home - Darien HS-DHS Main Gym [Directions] | 8:00 a.m. | ||
| Mon., 9/5 | V Girls Soccer | Weston (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 9/5 | JV Girls Soccer | Weston | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 9/7 | JV Boys Golf | Greenwich | Home - Woodway Country Club [Directions] | 3:15 p.m. | ||
| Wed., 9/7 | V Girls Soccer | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 9/7 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/8 | FR Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | V Boys Soccer | Norwalk | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 9/8 | JV Boys Soccer | Norwalk | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Girls Cross Country | Trumbull (Scrim.) | Away - Trumbull HS-Cross Country Course [Directions] | 4:15 p.m. | ||
| Sat., 9/10 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 1:30 p.m. | L 0-14 | |
| Sat., 9/10 | V Boys Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 12:00 p.m. | W 6-3 | |
| Sat., 9/10 | JV Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 9/10 | FR Boys Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 9/10 | V Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 3:00 p.m. | W 5-0 | |
| Sat., 9/10 | JV Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 9/10 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | W 5-0 | |
| Sat., 9/10 | JV Girls Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 3:00 p.m. | ||
| Sat., 9/10 | V Girls Volleyball | CIAC Early Season Volleyball Tournament @ CT Sports Center- Woodbridge | Away - Not Listed | 8:00 a.m. | ||
| Mon., 9/12 | JV Football | St. Joseph | Home - Darien HS-DHS Stadium East [Directions] | Canceled | Cancelled | |
| Mon., 9/12 | V Girls Soccer | Westhill | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 9/12 | JV Girls Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 9/13 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | Darien 165 Norwalk 185 | |
| Tue., 9/13 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 9/13 | JV Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | FR Boys Soccer | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Diving | Fairfield Ludlowe | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/13 | V Field Hockey | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 10-0 | |
| Tue., 9/13 | JV Field Hockey | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 9/14 | V Boys Cross Country | Danbury, Norwalk, Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Boys Golf | Ridgefield | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 168 Ridgefield 179 | |
| Wed., 9/14 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:00 p.m. | ||
| Wed., 9/14 | V Girls Cross Country | Danbury, Norwalk, Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:15 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Trumbull | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 3-3 | |
| Wed., 9/14 | FR Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | Amistad | Home - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 9/14 | JV Girls Volleyball | Amistad | Home - Darien HS-DHS Main Gym [Directions] | 6:30 p.m. | ||
| Thu., 9/15 | FR Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | FR Field Hockey | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 4:15 p.m. | ||
| Fri., 9/16 | V Boys Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 4-1 | |
| Fri., 9/16 | JV Boys Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/16 | JV Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:30 p.m. | ||
| Sat., 9/17 | V Football | Bridgeport Central | Home - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | W 47-0 | |
| Sat., 9/17 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:30 a.m. | ||
| Sat., 9/17 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 1:00 p.m. | W 8-0 | |
| Sat., 9/17 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 2:30 p.m. | ||
| Sat., 9/17 | FR Field Hockey | Norwalk | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 9/17 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | L 1-0 | |
| Sat., 9/17 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 10:00 a.m. | ||
| Mon., 9/19 | JV Football | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | V Boys Golf | Brien McMahon, St. Joseph | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 185 St. Joseph 165 Brien McMahon 185 | |
| Mon., 9/19 | FR Boys Soccer | Brien McMahon | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | V Girls Diving | Brien McMahon, Norwalk, Staples | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/19 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:00 p.m. | W 3-0 | |
| Mon., 9/19 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Westhill, Ridgefield, St. Joseph | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | Darien 156 Staples 148 | |
| Tue., 9/20 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | W 5-4 | |
| Tue., 9/20 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Westhill, Ridgefield, St. Joseph | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | FR Field Hockey | Ridgefield | Home - Darien HS-TBA [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Brien McMahon | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 2-1 | |
| Tue., 9/20 | JV Girls Soccer | Brien McMahon | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Boys Golf | Fairfield Prep | Away - CC of Fairfield [Directions] | 3:15 p.m. | Darien 175 Prep 145 | |
| Wed., 9/21 | FR Field Hockey | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | ||
| Wed., 9/21 | FR Girls Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 9/22 | FR Football | Maloney | Home - Darien HS-DHS Stadium East [Directions] | 5:00 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Bridgeport Central | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | W 5-2 | |
| Thu., 9/22 | JV Boys Soccer | Bridgeport Central | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | V Field Hockey | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:00 p.m. | W 6-2 | |
| Thu., 9/22 | JV Field Hockey | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 5:30 p.m. | ||
| Thu., 9/22 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 9/22 | V Girls Volleyball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/22 | JV Girls Volleyball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/22 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 9/23 | V Football | Maloney | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | L 9-21 | |
| Sat., 9/24 | JV Football | Maloney | Away - Maloney HS-Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 9/24 | V Boys Soccer | Conard | Away - Farmington Sports Arena [Directions] | 6:00 p.m. | T 1-1 | |
| Sat., 9/24 | V Girls Cross Country | Ocean State Invitational @ Goddard State Park, RI | Away - Goddard Park | TBA | ||
| Sat., 9/24 | V Girls Volleyball | John Jay G Volleyball Tournament | Away - Not Listed | 8:00 a.m. | ||
| Tue., 9/27 | V Boys Golf | Fairfield Prep | Home - Country Club of Darien [Directions] | 3:15 p.m. | Darien 178 Prep 164 | |
| Tue., 9/27 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 9/27 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Tue., 9/27 | FR Field Hockey | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | JV Girls Soccer | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/27 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | FR Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Boys Cross Country | Bridgeport Central, Brien McMahon, Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Boys Golf | Fairfield Ludlowe | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 175 :udlowe 170 | |
| Wed., 9/28 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | ||
| Wed., 9/28 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 9/28 | FR Boys Soccer | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Cross Country | Brien McMahon, Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Soccer | Staples | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 0-0 | |
| Wed., 9/28 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | FR Football | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | ||
| Thu., 9/29 | V Boys Golf | Greenwich | Away - Burning Tree Country Club [Directions] | 3:30 p.m. | Darien 161 Greenwich 157 | |
| Thu., 9/29 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | FR Girls Soccer | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/29 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | FR Girls Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | W 55-14 | |
| Fri., 9/30 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:45 p.m. | L 2-3 | |
| Fri., 9/30 | JV Boys Soccer | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | ||
| Fri., 9/30 | FR Boys Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Competitive Cheerleading | Fairfield Warde | Away - Fairfield Warde [Directions] | Canceled | Cancelled | |
| Fri., 9/30 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | W 8-0 | |
| Fri., 9/30 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | ||
| Fri., 9/30 | V Girls Soccer | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | T 2-2 | |
| Fri., 9/30 | JV Girls Soccer | Greenwich | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | JV Football | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Sat., 10/1 | FR Field Hockey | Newtown | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | Postponed | ||
| Sat., 10/1 | V Girls Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 2:00 p.m. | W 3-0 | |
| Sat., 10/1 | JV Girls Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 10/1 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/3 | V Boys Cross Country | Greenwich, Fairfield Ludlowe, New Canaan | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Girls Cross Country | Greenwich, Fairfield Ludlowe, New Canaan | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Diving | Wilton | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/4 | V Field Hockey | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/4 | JV Field Hockey | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 10/4 | V Girls Volleyball | Amistad | Away - Amistad HS-Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Tue., 10/4 | JV Girls Volleyball | Amistad | Away - Amistad HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 10/6 | V Boys Golf | CHAPPA Invitational @ Longshore | Away - Longshore Golf Course | 9:15 a.m. | ||
| Thu., 10/6 | JV Boys Golf | New Canaan | Home - Woodway Country Club [Directions] | 3:15 p.m. | ||
| Thu., 10/6 | V Boys Soccer | Danbury | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 1-6 | |
| Thu., 10/6 | JV Boys Soccer | Danbury | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | FR Field Hockey | Greenwich Academy | Away - Greenwich Academy - Everett Field | 4:30 p.m. | ||
| Thu., 10/6 | V Girls Swimming and Diving | Wilton | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 10/6 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 10/6 | FR Girls Volleyball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Field Hockey | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 10-0 | |
| Fri., 10/7 | JV Field Hockey | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | L 4-0 | |
| Fri., 10/7 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | FR Girls Soccer | Danbury | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 10/8 | V Field Hockey | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 11:00 a.m. | W 9-0 | |
| Sat., 10/8 | JV Field Hockey | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 12:30 p.m. | ||
| Sat., 10/8 | FR Field Hockey | Fairfield Warde | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | Canceled | Cancelled | |
| Sat., 10/8 | V Girls Volleyball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 10/8 | JV Girls Volleyball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 12:30 p.m. | ||
| Mon., 10/10 | V Boys Soccer | St. Joseph | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 7-2 | |
| Mon., 10/10 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/10 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/10 | FR Girls Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Boys Cross Country | Staples, Stamford, Trumbull | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | JV Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 10/11 | V Girls Cross Country | Staples, Stamford, Trumbull | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Field Hockey | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 7-0 | |
| Tue., 10/11 | JV Field Hockey | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 2-1 | |
| Tue., 10/11 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | Darien 178 Wilton 174 | |
| Wed., 10/12 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Wed., 10/12 | V Boys Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/12 | JV Boys Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | FR Field Hockey | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 10/12 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/12 | FR Girls Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | FR Football | Ridgefield | Home - Darien HS-DHS Stadium East [Directions] | 5:00 p.m. | ||
| Thu., 10/13 | V Boys Golf | Danbury, New Canaan | Home - Wee Burn CC [Directions] | 3:15 p.m. | New Canaan 156 (rescheduled from 10/4/22) Darien 163 Danbury 174 Danbury 174 | |
| Thu., 10/13 | JV Boys Golf | Fairfield Prep | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Thu., 10/13 | JV Boys Golf | Ridgefield | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Thu., 10/13 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | W 6-0 | |
| Thu., 10/13 | FR Field Hockey | Trumbull | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 10/13 | JV Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Thu., 10/13 | FR Girls Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Football | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | W 18-15 | |
| Fri., 10/14 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/14 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Competitive Cheerleading | To Wilton | Away - Wilton HS | 7:00 p.m. | ||
| Fri., 10/14 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/14 | JV Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/14 | JV Girls Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/15 | JV Football | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | FR Boys Soccer | Ridgefield | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Girls Soccer | Ridgefield | Home - Darien HS-DHS Center Oval - Turf [Directions] | 2:00 p.m. | L 1-0 | |
| Sat., 10/15 | JV Girls Soccer | Ridgefield | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Girls Swimming and Diving | St. Joseph | Away - FLOOD MS [Directions] | 2:00 p.m. | ||
| Mon., 10/17 | V Boys Golf | Holahan | Home - Wee Burn CC [Directions] | 11:30 a.m. | ||
| Mon., 10/17 | V Boys Soccer | Stamford | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/17 | JV Boys Soccer | Stamford | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | FR Boys Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | FR Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Girls Swimming and Diving | Fairfield Warde | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/17 | JV Girls Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club [Directions] | 3:15 p.m. | ||
| Tue., 10/18 | V Field Hockey | Danbury | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 10-0 | |
| Tue., 10/18 | JV Field Hockey | Danbury | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/18 | JV Girls Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/19 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/19 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/19 | JV Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 10/19 | FR Field Hockey | Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | ||
| Wed., 10/19 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/19 | JV Girls Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Football | St. Joseph | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | FR Boys Soccer | Wilton | Away - Allen's Meadow-Field #1 [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | V Girls Diving | St. Joseph, TBA, Trumbull | Away - New Canaan Y -Diving Only [Directions] | 3:45 p.m. | ||
| Thu., 10/20 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | W 2-0 | |
| Thu., 10/20 | JV Girls Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 10/21 | V Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 35-25 | |
| Fri., 10/21 | V Boys Soccer | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 6-3 | |
| Fri., 10/21 | JV Boys Soccer | Wilton | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | ||
| Fri., 10/21 | V Competitive Cheerleading | Fairfield Ludlowe | Away - Fairfield Ludlowe HS [Directions] | 7:00 p.m. | ||
| Fri., 10/21 | FR Girls Soccer | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/21 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 10/21 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/22 | JV Football | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Mon., 10/24 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | T 1-1 | |
| Mon., 10/24 | FR Boys Soccer | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | V Field Hockey | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 9-0 | |
| Mon., 10/24 | JV Field Hockey | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/24 | JV Girls Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Fairfield Warde | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 10/25 | JV Girls Soccer | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | ||
| Wed., 10/26 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | JV Girls Soccer | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | V Girls Volleyball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/26 | JV Girls Volleyball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/27 | V Boys Cross Country | Danbury | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | FR Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 10/27 | V Boys Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | V Girls Cross Country | Danbury | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/27 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/27 | FR Girls Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/28 | V Field Hockey | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 9-0 | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 9:35 a.m. | ||
| Sat., 10/29 | V Football | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | L 20-28 | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:10 a.m. | ||
| Sat., 10/29 | JV Girls Swimming and Diving | Greenwich, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 10:15 a.m. | ||
| Sat., 10/29 | FR Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 9:00 a.m. | ||
| Mon., 10/31 | JV Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | V Boys Golf | CIAC Division I Championship | Away - Stanley GC | 9:00 a.m. | ||
| Tue., 11/1 | V Boys Soccer | Norwalk | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 11/1 | V Field Hockey | New Canaan | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 11/1 | V Girls Soccer | Trumbull (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | ||
| Tue., 11/1 | V Girls Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | Miscellaneous Events | Boys Freshman Soccer Fan bus to FCIAC Semi-finals @ Fairfield Ludlowe | Home - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 11/1 | Miscellaneous Events | Boys JV Soccer Fan Bus to FCIAC Semi-Finals | Home - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championship | Away - Westhill HS-Westhill Pool | 5:00 p.m. | ||
| Wed., 11/2 | V | Unified to Fairfield Ludlowe | Away - Fairfield Ludlowe HS | 4:00 p.m. | ||
| Thu., 11/3 | FR Football | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 11/3 | V Boys Soccer | Trumbull | Away - Norwalk HS-Testa Field, NHS [Directions] | 7:00 p.m. | ||
| Thu., 11/3 | V Field Hockey | Staples | Home - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 11/3 | V Girls Volleyball | Greenwich | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 11/3 | Miscellaneous Events | Boys JV Soccer Fan Bus for FCIAC Championship Game @ Norwalk | Home - Norwalk HS-Testa Field, NHS [Directions] | 7:00 p.m. | ||
| Thu., 11/3 | Miscellaneous Events | Boys Freshman Soccer Fan Bus for FCIAC Championship Game @ Norwalk | Home - Norwalk HS-Testa Field, NHS [Directions] | 7:00 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 49-0 | |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Sat., 11/5 | JV Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 2:00 p.m. | ||
| Sat., 11/5 | V Girls Volleyball | Trumbull | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 3:00 p.m. | ||
| Mon., 11/7 | V Boys Soccer | Conard | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | ||
| Tue., 11/8 | V Girls Soccer | West Haven | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Boys Soccer | South Windsor | Away - South Windsor HS-Multi-purpose field [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Field Hockey | Newtown | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 11/9 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/10 | V Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | W 42-21 | |
| Thu., 11/10 | FR Football | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 11/10 | V Competitive Cheerleading | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Thu., 11/10 | V Girls Soccer | Cheshire | Away - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 11/11 | V Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | W 4-2 | |
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class L Trials | Away - Cornerstone Pool | 4:30 p.m. | ||
| Mon., 11/14 | JV Football | Brien McMahon | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Mon., 11/14 | V Girls Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 11/15 | V Field Hockey | Glastonbury | Home - Amity Regional HS-Field Hockey Field [Directions] | 6:00 p.m. | ||
| Tue., 11/15 | V Girls Swimming and Diving | CIAC Class L Final | Away | 6:00 p.m. | ||
| Wed., 11/16 | V Girls Volleyball | Southington | Away - Bunnell HS [Directions] | 6:00 p.m. | ||
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | JV Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/19 | V Field Hockey | Wilton | Home - Wethersfield HS-Cottone Field [Directions] | 2:00 p.m. | ||
| Sat., 11/19 | V Girls Volleyball | Trumbull | Home - East Haven HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 11/19 | Miscellaneous Events | Tentative Fan Bus for Volleyball State Championship game at East Haven HS | Home - East Haven HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 11/19 | Miscellaneous Events | Tentative Fan bus for Field Hockey State Championship game @ Wethersfield HS | Home - Wethersfield HS-Cottone Field [Directions] | 2:00 p.m. | ||
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Thu., 11/24 | V Football | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | L 10-13 | |
| Sat., 12/3 | V Boys Ice Hockey | Scrimmage v Marshfield, MA | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | ||
| Mon., 12/5 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | W 7-1 | |
| Tue., 12/6 | V Boys Basketball | Harding (Scrim.) | Away - Warren Harding HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/6 | V Girls Basketball | Bethel (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 12/6 | JV Girls Basketball | Bethel (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 12/7 | V Girls Squash | G varsity squash v Hopkins @ Hopkins School | Away - Not Listed | 3:30 p.m. | ||
| Wed., 12/7 | JV Girls Squash | G JV squash @ Hopkins School | Away - Not Listed | 3:30 p.m. | ||
| Thu., 12/8 | V Boys Squash | Boys V squash v Rye @ Lifetime of Rye | Away - Not Listed | 8:00 p.m. | ||
| Fri., 12/9 | V Boys Basketball | Weston (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/9 | JV Boys Basketball | Weston (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 12/9 | V Boys Ice Hockey | Xaverian Brothers (MA) (Scrim.) | Away - Canton Ice House | 4:20 p.m. | ||
| Fri., 12/9 | V Girls Basketball | Weston (Scrim.) | Away - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Fri., 12/9 | JV Girls Basketball | Weston (Scrim.) | Away - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Fri., 12/9 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 8:20 p.m. | W 4-0 | |
| Sat., 12/10 | V Boys Ice Hockey | St. Johns Prep (MA) (Scrim.) | Away - Essex Sports Center - Middleton-Ice Rink | 10:00 a.m. | Overnight trip Same LandJet bus charter #7204 | |
| Sat., 12/10 | JV Boys Ice Hockey | Notre Dame-West Haven (Scrim.) | Home - Stamford Twin Rinks-West [Directions] | 7:45 p.m. | ||
| Sat., 12/10 | V Wrestling | Suffield/Windsor Locks, Canton, Coventry, Granby Memorial, Rockville | Away - Suffield HS | 9:00 a.m. | ||
| Sat., 12/10 | V Girls Ice Hockey | Simsbury | Home - Darien Ice House-Ice Rink [Directions] | 5:50 p.m. | W 7-1 | |
| Sat., 12/10 | V Girls Squash | G V squash @ Choate | Away - Choate School | 3:30 p.m. | ||
| Sat., 12/10 | JV Girls Squash | Girls JV Squash to Choate | Away - Choate School | 3:30 p.m. | ||
| Mon., 12/12 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-TBA [Directions] | 4:00 p.m. | ||
| Mon., 12/12 | V Girls Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 41-16 | |
| Mon., 12/12 | JV Girls Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 12/12 | JV Girls Squash | G JV squash v Rye Grey @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Tue., 12/13 | V Girls Basketball | Wilbur Cross | Away - Wilbur Cross HS-Gym [Directions] | 7:00 p.m. | W 56-33 | |
| Tue., 12/13 | JV Girls Basketball | Wilbur Cross | Away - Wilbur Cross HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/13 | FR Girls Basketball | Wilbur Cross | Away - Wilbur Cross HS-Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/13 | V Girls Squash | G V squash v City Squash @ Fordham U | Away - Not Listed | 6:00 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Hamden | Away - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | W 5-0 | |
| Wed., 12/14 | V Boys Squash | B V squash v Greenwich @ Greenwich Field Club | Away - Not Listed | 7:30 p.m. | ||
| Wed., 12/14 | V Wrestling | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/14 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:40 p.m. | W 7-0 | |
| Thu., 12/15 | V Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 7:00 p.m. | W 74-52 | |
| Thu., 12/15 | JV Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/15 | FR Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/15 | JV Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:15 p.m. | ||
| Thu., 12/15 | V Boys Swimming and Diving | Wilton | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 12/15 | V Girls Basketball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 13-59 | |
| Thu., 12/15 | JV Girls Basketball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/15 | FR Girls Basketball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/16 | V Boys Diving | Wilton | Home - New Canaan Y -Diving Only [Directions] | 3:30 p.m. | ||
| Fri., 12/16 | V Boys Indoor Track | Coach Saint Invite @ NYC Armory | Away - NYC Armory | 5:00 p.m. | ||
| Fri., 12/16 | V Girls Indoor Track | Coach Saint Invite @ New York Armory | Away - NYC Armory | 5:00 p.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Northwest Catholic | Home - Darien Ice House-Ice Rink [Directions] | 5:30 p.m. | W 4-3 | |
| Sat., 12/17 | V Boys Indoor Track | Wilton, Brien McMahon, Fairfield Warde, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 12/17 | JV Boys Squash | B JV squash v Hartford & Rye @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 1:00 p.m. | ||
| Sat., 12/17 | V Wrestling | Darien Invitational | Home - Darien HS-DHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 12/17 | V Girls Indoor Track | Wilton, Brien McMahon, Fairfield Warde, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 12/17 | JV Girls Squash | G JV squash FairWest Round Robin v Hartford, Rye Red @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 1:00 p.m. | ||
| Sun., 12/18 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | ||
| Mon., 12/19 | V Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | L 32-35 | |
| Mon., 12/19 | JV Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/20 | V Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 77-35 | |
| Tue., 12/20 | JV Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | FR Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Girls Squash | G V squash v Westport @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | W 4-2 | |
| Wed., 12/21 | V Wrestling | St. Joseph | Home - Darien HS-DHS South Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/21 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 8:00 p.m. | W 6-0 | |
| Thu., 12/22 | V Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 7:00 p.m. | W 79-41 | |
| Thu., 12/22 | JV Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/22 | FR Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/22 | V Boys Indoor Track | Hillhouse Holiday Invitational | Away - New Haven Athletic Center/Hillhouse HS | Canceled | Cancelled | |
| Thu., 12/22 | V Girls Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | L 18-43 | |
| Thu., 12/22 | JV Girls Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/22 | FR Girls Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Mon., 12/26 | JV Wrestling | Tumbull HS JV Wrestling Tournament | Away - Trumbull HSchool | 9:00 a.m. | ||
| Tue., 12/27 | V Wrestling | Fairfield Prep | Home - Darien HS-DHS South Gym [Directions] | 10:00 a.m. | ||
| Wed., 12/28 | V Boys Basketball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 2:00 p.m. | L 52-58 | |
| Wed., 12/28 | JV Boys Basketball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 12:30 p.m. | ||
| Wed., 12/28 | FR Boys Basketball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | ||
| Wed., 12/28 | V Wrestling | Danbury, Bethel, Brookfield/Shepaug, Coventry (RI), Enfield, TBA, TBA, TBA, TBA, New Milford, Northfield Mt. Hampton (MA), Norwalk, Putnam Vo-Tech (MA), South Windsor, Staples, Wilton | Away - Danbury HS-Main Gym | 9:15 a.m. | ||
| Thu., 12/29 | V Boys Ice Hockey | Greenwich | Away - Greenwich Skating Club [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 12/29 | JV Boys Ice Hockey | Greenwich | Away - Greenwich Skating Club-Ice Rink [Directions] | 10:00 a.m. | ||
| Thu., 12/29 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 1:00 p.m. | L 30-49 | |
| Fri., 12/30 | V Boys Indoor Track | Relay Rust Buster @ SCSU/New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Fri., 12/30 | V Wrestling | Danbury, Stamford, Staples | Home - Darien HS-DHS South Gym [Directions] | 10:00 a.m. | ||
| Tue., 1/3 | V Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | L 47-48 | |
| Tue., 1/3 | JV Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | ||
| Tue., 1/3 | V Boys Indoor Track | Will Wright Invite at SCSU, New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 27-37 | |
| Tue., 1/3 | JV Girls Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | FR Girls Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/3 | V Girls Indoor Track | Wilton Wright Invite at SCSU, New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | T 2-2 OT | |
| Wed., 1/4 | V Boys Swimming and Diving | St. Joseph, Trumbull | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/4 | V Wrestling | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 5-1 | |
| Thu., 1/5 | V Boys Indoor Track | Wintergreen Invite @ SCSU/New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Thu., 1/5 | V Girls Gymnastics | Westhill, New Canaan, Stamford | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | Darien 125.75 Stamford 93.85 New Canaan 75.35 Westhill 52.7 | |
| Thu., 1/5 | V Girls Indoor Track | Wintergreen Invite @ SCSU | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 53-48 | |
| Fri., 1/6 | JV Boys Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | JV Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | ||
| Fri., 1/6 | V Boys Squash | B V squash v NC @ MSquash Sono | Home - Not Listed [Directions] | 6:00 p.m. | ||
| Fri., 1/6 | JV Boys Squash | B JV squash v NC @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | L 33-47 | |
| Fri., 1/6 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 1/6 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Darien vs Warwick Co_Op, RI | Home - Darien Ice House-Ice Rink [Directions] | 7:50 p.m. | T 2-2 OT | |
| Sat., 1/7 | V Boys Indoor Track | Wilton, New Canaan, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/7 | V Wrestling | Somers Invitational | Away - Somers HS-Somers High School Gymnasium | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Ice Hockey | Greenwich Academy | Home - Terry Conners - Stamford-Ice Rink [Directions] | 12:30 p.m. | T 1-1 | |
| Sat., 1/7 | V Girls Indoor Track | Wilton, New Canaan, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Squash | G V squash v Street Squash & NC @ Street Squash NYC | Away - Not Listed | Canceled | Cancelled | |
| Sun., 1/8 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | ||
| Mon., 1/9 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:00 p.m. | W 7-1 | |
| Tue., 1/10 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 7:00 p.m. | W 62-48 | |
| Tue., 1/10 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | JV Wrestling | Fairfield Ludlowe, Branford | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | W 28-24 | |
| Tue., 1/10 | JV Girls Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/10 | V Girls Gymnastics | Wilton, New Canaan | Away - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | Darien 132.85 Wilton 136.95 | |
| Wed., 1/11 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 4:10 p.m. | T 3-3 OT | |
| Wed., 1/11 | V Boys Indoor Track | James Barber Invite @ SCSU/New Haven | Away - Southern Connecticut State University | Canceled | Cancelled | |
| Wed., 1/11 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Wed., 1/11 | V Wrestling | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/11 | V Co-ed Alpine Skiing | Ski Race | Away - Mt. Southingon Ski Area | 4:00 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice House-Ice Rink [Directions] | 8:50 p.m. | W 6-3 | |
| Wed., 1/11 | V Girls Indoor Track | James Barber Invite @ SCSU | Away - Southern Connecticut State University | Canceled | Cancelled | |
| Thu., 1/12 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Fri., 1/13 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 47-56 | |
| Fri., 1/13 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Boys Indoor Track | Steve Borbet Invite @ NYC Armory | Away - NYC Armory | 5:30 p.m. | ||
| Fri., 1/13 | JV Boys Squash | Boys JV squash v Rye B @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 20-41 | |
| Fri., 1/13 | JV Girls Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | FR Girls Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Indoor Track | Steve Borbet Invite @ NYC Armory | Away - NYC Armory | 5:30 p.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | Westhill/Stamford | Home - Darien Ice House-Ice Rink [Directions] | 7:10 p.m. | W 6-1 | |
| Sat., 1/14 | V Boys Indoor Track | Staples, St. Joseph, Stamford | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | V Wrestling | Bunnell, Derby/Oxford/Holy Cross, New Fairfield, Weston | Home - Darien HS-DHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 1/14 | V Girls Gymnastics | St. Joseph, Trumbull | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien 130.25 Trumbull 120.5 St. Joe's 120.45 | |
| Sat., 1/14 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 5:50 p.m. | W 1-0(OT) | |
| Sat., 1/14 | V Girls Indoor Track | Staples, St. Joseph, Stamford | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | Xavier | Away - Cromwell-Upper Rink [Directions] | 3:00 p.m. | W 4-2 | |
| Mon., 1/16 | JV Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 5:30 p.m. | ||
| Mon., 1/16 | V Girls Ice Hockey | Avon | Away - Newington-Blue Rink [Directions] | 4:20 p.m. | W 7-1 | |
| Tue., 1/17 | V Boys Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 55-67 | |
| Tue., 1/17 | JV Boys Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | L 32-59 | |
| Tue., 1/17 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | ||
| Wed., 1/18 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Wrestling | Foran | Home - Darien HS-DHS South Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/18 | V Co-ed Alpine Skiing | Race | Away - Mt. Southingon Ski Area | 4:00 p.m. | ||
| Wed., 1/18 | V Girls Gymnastics | Fairfield Ludlowe | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Darien 137.5 Fairfield Ludlowe 138.15 Fairfield Warde 141 | |
| Wed., 1/18 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | ||
| Wed., 1/18 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | W 3-2 | |
| Thu., 1/19 | V Boys Squash | B V squash v Scarsdale @ Westchester Squash Academy | Away - Not Listed | 8:00 p.m. | ||
| Thu., 1/19 | V Girls Squash | G V squash v Rye @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Fri., 1/20 | V Boys Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 52-56 | |
| Fri., 1/20 | JV Boys Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | JV Boys Ice Hockey | Fairfield Prep | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | W 3-2 OT | |
| Sat., 1/21 | V Boys Indoor Track | Staples, Norwalk, Stamford | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Boys Indoor Track | SCC Coaches Invite @ Hillhouse/New Haven | Away - New Haven Athletic Center/Hillhouse HS | 2:30 p.m. | ||
| Sat., 1/21 | V Boys Squash | B V squash v Brunswick, Haverford & St Andrews @ Brunswick- all day | Away - Not Listed | 9:30 a.m. | No bus needed | |
| Sat., 1/21 | V Wrestling | Granby Duals | Away - Granby Memorial HS-K.L. King Gymnasium | 9:30 a.m. | ||
| Sat., 1/21 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 6:00 p.m. | L 36-64 | |
| Sat., 1/21 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:45 p.m. | ||
| Sat., 1/21 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:15 p.m. | ||
| Sat., 1/21 | V Girls Gymnastics | Norwalk, Staples | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien: 130.65 Staples: 130.25 Norwalk: 43.65 | |
| Sat., 1/21 | V Girls Indoor Track | Staples, Norwalk, Stamford | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | SCC Coaches Meet @ New Haven Athletic Center | Away - New Haven Athletic Center/Hillhouse HS | 9:00 a.m. | ||
| Sun., 1/22 | JV Boys Squash | B JV squash v Street Squash @ Street Squash | Away - Not Listed | 10:00 a.m. | ||
| Sun., 1/22 | V Girls Squash | G V squash v Squash Haven @ Street Squash | Away - Not Listed | 10:00 a.m. | ||
| Mon., 1/23 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 1/23 | JV Boys Squash | B JV squash v Fairfield @ Intensity- South Norwalk | Away - Not Listed | 7:30 p.m. | ||
| Mon., 1/23 | JV Girls Squash | G JV squash v Rye Black @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | W 44-60 | |
| Tue., 1/24 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 41-44 | |
| Tue., 1/24 | JV Girls Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/25 | V Wrestling | Fairfield Ludlowe | Home - Darien HS-DHS South Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/26 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 49-67 | |
| Thu., 1/26 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/26 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/26 | V Girls Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 37-53 | |
| Thu., 1/26 | JV Girls Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/26 | FR Girls Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/26 | V Girls Ice Hockey | Brewster (NY) | Away - Brewster HS-Ice Rink | 7:40 p.m. | W 4-2 | |
| Fri., 1/27 | JV Boys Ice Hockey | St. Joseph | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 1/27 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | L 2-3 | |
| Sat., 1/28 | V Boys Indoor Track | FCIAC Eastern Division Championship @ Wilton HS | Away - Wilton HS | 9:00 a.m. | ||
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Away - Brookfield HS-BHS Small Gym | 9:30 a.m. | ||
| Sat., 1/28 | JV Wrestling | Neil Godleski Wrestling Tournament | Away - Norwalk HS-Tom Scarso Gymnasium | 9:00 a.m. | ||
| Sat., 1/28 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:30 p.m. | W 6-0 | |
| Sat., 1/28 | V Girls Indoor Track | FCIAC Eastern Division Championships at Wilton | Away - Wilton HS | 9:00 a.m. | ||
| Sun., 1/29 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 7:45 p.m. | ||
| Mon., 1/30 | V Boys Squash | B V squash v Hackley @ Hackley School | Away - Not Listed | 4:30 p.m. | ||
| Mon., 1/30 | JV Boys Squash | B JV squash v Hackley @ Hackley School | Away - Not Listed | 4:30 p.m. | ||
| Mon., 1/30 | V Co-ed Alpine Skiing | Race | Away - Mt. Southingon Ski Area | 4:00 p.m. | ||
| Mon., 1/30 | V Girls Squash | G V squash v Bronxville @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Tue., 1/31 | V Boys Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 57-36 | |
| Tue., 1/31 | JV Boys Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Boys Diving | Staples | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | W 47-32 | |
| Tue., 1/31 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice House-Ice Rink [Directions] | 8:20 p.m. | W 9-0 | |
| Wed., 2/1 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | W 1-0 | |
| Wed., 2/1 | V Boys Squash | B V squash v Bronxville @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Wed., 2/1 | JV Boys Squash | Staples | Home - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Wed., 2/1 | V Boys Swimming and Diving | Staples | Home - Darien YMCA [Directions] | 3:30 p.m. | ||
| Wed., 2/1 | V Wrestling | Ridgefield | Home - Darien HS-DHS South Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/1 | V Co-ed Alpine Skiing | Race | Away - Mt. Southingon Ski Area | 4:00 p.m. | ||
| Wed., 2/1 | V Girls Ice Hockey | Greenwich Academy | Home - Darien Ice House-Ice Rink [Directions] | 7:10 p.m. | T 1-1 | |
| Thu., 2/2 | JV Boys Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Thu., 2/2 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 29-35 | |
| Thu., 2/2 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Thu., 2/2 | V Girls Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Thu., 2/2 | V Girls Squash | G V squash v Hackley School @ Hackley School | Away - Not Listed | 4:00 p.m. | ||
| Thu., 2/2 | JV Girls Squash | G JV squash v Hackley School @ Hackley School | Away - Not Listed | 4:00 p.m. | ||
| Fri., 2/3 | V Boys Squash | B V squash- potential round robin match @ Kent School | Away - Not Listed | Canceled | Cancelled | |
| Fri., 2/3 | V Boys Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 2/3 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | V Boys Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 3:00 p.m. | W 70-39 | |
| Sat., 2/4 | V Boys Ice Hockey | Bishop Hendricken (RI) | Away - Bishop Hendricken HS-Thayer/Warburton Ice Arena | 5:00 p.m. | L 2-5 | |
| Sat., 2/4 | V Boys Indoor Track | FCIAC Last Chance Meet @ Staples HS | Away - Staples HS | 10:00 a.m. | ||
| Sat., 2/4 | V Wrestling | East Lyme/Norwich Tech, Fairfield Prep, Montville | Away - East Lyme HS-North Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/4 | V Girls Gymnastics | Greenwich | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien: 131.25 Greenwich: 120.05 | |
| Sat., 2/4 | V Girls Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 7:00 p.m. | W 3-1 | |
| Sat., 2/4 | V Girls Indoor Track | FCIAC Last Chance Meet @ Staples | Away - Staples HS | 10:00 a.m. | ||
| Sun., 2/5 | V Boys Ice Hockey | LaSalle Academy (RI) | Away - Smithfield Municipal Ice Rink-SMIR | 5:30 p.m. | L 3-4 | |
| Mon., 2/6 | JV Boys Squash | B JV squash v City Squash @ Fordham University | Away - Not Listed | 6:00 p.m. | ||
| Mon., 2/6 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Mon., 2/6 | V Girls Squash | G V squash v New Canaan @ Chelsea Piers | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Mon., 2/6 | JV Girls Squash | G JV squash v Greenwich @ Greenwich Field Club | Away - Not Listed | 7:30 p.m. | No bus needed | |
| Tue., 2/7 | V Boys Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 48-67 | |
| Tue., 2/7 | JV Boys Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 30-51 | |
| Tue., 2/7 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 5:20 p.m. | W 5-1 | |
| Wed., 2/8 | V Boys Squash | B V squash @ Rye Country Day School | Away - Not Listed | 4:45 p.m. | ||
| Wed., 2/8 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/8 | V Co-ed Alpine Skiing | Race | Away - Mt. Southingon Ski Area | 4:00 p.m. | ||
| Wed., 2/8 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 1-0 | No bus needed |
| Wed., 2/8 | V Girls Squash | G V squash @ Rye Country Day School | Away - Not Listed | 3:30 p.m. | ||
| Thu., 2/9 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/9 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | JV Boys Ice Hockey | Xavier | Away - Cromwell-Upper Rink [Directions] | 4:20 p.m. | ||
| Thu., 2/9 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/10 | V Boys Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 35-47 | |
| Fri., 2/10 | JV Boys Ice Hockey | Greenwich | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 2/10 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/10 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Fri., 2/10 | V Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 25-36 | |
| Fri., 2/10 | JV Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 4:30 p.m. | L 1-4 | |
| Sat., 2/11 | V Wrestling | FCIAC Championships | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Sat., 2/11 | V Girls Gymnastics | FCIAC Gymnastics Championship @ Gymnastics & Cheerleading Academy, Fairfield | Away - Gymnastics and Cheerleading Academy at Connecticut | 10:00 a.m. | FCIAC Championship 5th place | |
| Sat., 2/11 | V Girls Ice Hockey | Avon | Home - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | L 7-6 | |
| Sat., 2/11 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 64-55 | |
| Mon., 2/13 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Squash | Hopkins School | Away - Hopkins School | 4:30 p.m. | ||
| Mon., 2/13 | JV Boys Squash | B JV squash v Hopkins @ Hopkins School | Away - Not Listed | 3:30 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 20-48 | |
| Mon., 2/13 | JV Girls Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Girls Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Mon., 2/13 | V Girls Ice Hockey | Rye Country Day (NY) | Away - Rye Country Day School-Ice Rink | 3:30 p.m. | W 6-1 | |
| Mon., 2/13 | V Girls Squash | G V squash v Briarcliff @ CP | Home - Chelsea Piers - Field Side-Chelsea Piers Connecticut [Directions] | 7:30 p.m. | ||
| Tue., 2/14 | V Boys Squash | Staples | Home - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Tue., 2/14 | V Co-ed Alpine Skiing | Fun Race @ Powder Ridge | Away - Powder Ridge Mountain | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 45-46 | |
| Wed., 2/15 | JV Boys Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | W 4-1 | |
| Wed., 2/15 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 45-48 | |
| Wed., 2/15 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | JV Girls Squash | Staples | Away - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Thu., 2/16 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 6-0 | |
| Thu., 2/16 | V Girls Gymnastics | Staples, Norwalk | Away - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | Darien 126.9 Staples 131.7 | |
| Fri., 2/17 | V Wrestling | CIAC LL Championship | Away - Trumbull | 4:00 p.m. | ||
| Sat., 2/18 | JV Boys Ice Hockey | Trumbull | Home - Stamford Twin Rinks-East [Directions] | 8:30 p.m. | ||
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC LL Championship | Away - Trumbull | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 52-58 | |
| Mon., 2/20 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/22 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 39-55 | |
| Wed., 2/22 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/22 | V Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | L 4-7 | |
| Wed., 2/22 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks-East [Directions] | 8:05 p.m. | ||
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | ||
| Sat., 2/25 | V Girls Ice Hockey | TBA | Home - Darien Ice House-Ice Rink [Directions] | 4:30 p.m. | Cancelled | |
| Sat., 2/25 | V Girls Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 4:30 p.m. | ||
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Wed., 3/1 | V Boys Basketball | Brien McMahon (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 3/1 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Wed., 3/1 | JV Boys Ice Hockey | St. Joseph | Home - Blake Field - New Haven-Walker Rink [Directions] | 8:30 p.m. | ||
| Thu., 3/2 | V Boys Diving | B Diving FCIAC's @ Westhill | Away - Not Listed | 5:00 p.m. | ||
| Thu., 3/2 | V Girls Ice Hockey | West Haven/SHA | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | ||
| Fri., 3/3 | JV Boys Ice Hockey | New Canaan | Away - Blake Field - New Haven-Walker Rink [Directions] | 6:30 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | Greenwich, Danbury, Farfield Ludlowe/Warde, Fairfield Warde, TBA, New Canaan, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Sat., 3/4 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Danbury Ice Arena-Patriot Rink [Directions] | 3:00 p.m. | ||
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Sat., 3/4 | V Girls Ice Hockey | East Catholic Coop | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:50 p.m. | ||
| Mon., 3/6 | V Boys Basketball | Prince Tech | Away - Prince Tech / Mark Snyder Gym [Directions] | 6:00 p.m. | ||
| Mon., 3/6 | JV Boys Ice Hockey | Tourney | Away - Ralph Walker Ice Rink | 8:00 p.m. | ||
| Wed., 3/8 | V Boys Basketball | WCA | Away - Wilby HS-Gym [Directions] | 6:30 p.m. | ||
| Wed., 3/8 | V Boys Ice Hockey | West Haven Coop | Home - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Wed., 3/8 | V Girls Ice Hockey | Avon | Home - Quinnipiac University-Quinnipiac [Directions] | 7:00 p.m. | ||
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class L Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Fri., 3/10 | V Boys Indoor Track | Nike Indoor Nationals @ Armory in NYC | Away - The Armory | 8:30 a.m. | ||
| Sat., 3/11 | V Boys Ice Hockey | New Canaan | Away - Sacred Heart University-Martire Arena [Directions] | 1:00 p.m. | ||
| Sun., 3/12 | V Boys Swimming and Diving | CIAC Class L Trials | Away - Cornerstone Pool | 3:15 p.m. | ||
| Mon., 3/13 | V | Unified Sports Basketball Tournament @ Fairfield Ludlowe | Away - Fairfield Ludlowe HS | 3:30 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Tue., 3/21 | V Boys Lacrosse | TBA | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 3/21 | V Boys Volleyball | Iona Prep (NY) (Scrim.) | Away - Iona Preparatory School-Gym | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 4/3 | ||||||
| Tue., 3/21 | V Boys Volleyball | Iona Prep (NY) (Scrim.) | Away - Iona Preparatory School-Gym | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 4/3 | ||||||
| Wed., 3/22 | V Baseball | Wilton (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 3/22 | JV Baseball | Wilton (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Thu., 3/23 | V Boys Lacrosse | Stepinac (NY) (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 3/23 | JV Boys Lacrosse | Stepinac (NY) (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 3/24 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Delbarton (NJ) (Scrim.) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 9:00 a.m. | ||
| Sat., 3/25 | FR Boys Lacrosse | Chaminade (NY) (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Sat., 3/25 | V Boys Volleyball | Scrimmage | Home - Darien HS-DHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 3/25 | V Girls Lacrosse | G Lax scrimmage @ Bayport Bluepoint | Away - Not Listed | TBA | Cancelled | |
| Sun., 3/26 | V Baseball | Stamford (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 9:00 a.m. | Possible double-header | |
| Sun., 3/26 | JV Baseball | Stamford (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 9:00 a.m. | Possible double-header | |
| Sun., 3/26 | V Softball | Stamford (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 11:00 a.m. | ||
| Tue., 3/28 | FR Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 3:30 p.m. | ||
| Tue., 3/28 | V Softball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Baseball | Greenwich (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | JV Baseball | Greenwich (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Boys Lacrosse | Cheshire (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 3/29 | JV Boys Lacrosse | Cheshire (Scrim.) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:30 p.m. | ||
| Wed., 3/29 | V Co-ed Sailing | Greenwich | Away - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 3/29 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Turf field | 3:45 p.m. | ||
| Wed., 3/29 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Softball | Greenwich (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 4/1 | V Baseball | Wilbur Cross | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:00 p.m. | W 10-0 | |
| Sat., 4/1 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 7:30 p.m. | W 9-8 | |
| Sat., 4/1 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 5:00 p.m. | ||
| Sat., 4/1 | FR Boys Lacrosse | Fairfield Prep | Home - Darien HS-DHS Center Oval - Turf [Directions] | 10:30 a.m. | ||
| Sat., 4/1 | V Boys Rugby | Trumbull (Scrim.) | Away - Trumbull HS-Aux Gym [Directions] | 10:30 a.m. | ||
| Sat., 4/1 | V Boys Volleyball | B Volleyball Pre-Season Tournament- CT Volleyball Center in Woodbridge | Away - Not Listed | 8:00 a.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Manhassett (NY) | Away - Manhasset Junior/Senior HS | 12:00 p.m. | W 18-5 | |
| Sat., 4/1 | JV Girls Lacrosse | Manhassett (NY) | Away - Manhasset Junior/Senior HS | 10:00 a.m. | ||
| Mon., 4/3 | V Baseball | New Fairfield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | W 11-4 | |
| Mon., 4/3 | JV Baseball | New Fairfield | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:30 p.m. | ||
| Mon., 4/3 | FR Baseball | Westhill | Home - Darien HS-Town Hall Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/3 | JV Boys Tennis | Greenwich | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/3 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | FR Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | JV Boys Tennis | Trumbull | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | V Co-ed Sailing | Greenwich | Away - Grass Island [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:15 p.m. | ||
| Tue., 4/4 | V Girls Lacrosse | Sacred Heart of Greenwich | Away - Sacred Heart Greenwich-Stadium 2 | 4:00 p.m. | W 9-8 | |
| Tue., 4/4 | JV Girls Lacrosse | Sacred Heart of Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 3:30 p.m. | ||
| Wed., 4/5 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | L 2-3 | |
| Wed., 4/5 | V Boys Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Boys Volleyball | Farmington | Home - Darien HS-DHS Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Wed., 4/5 | JV Boys Volleyball | Farmington | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 4/5 | V Co-ed Sailing | Sailing v Guilford, Rye, Hotchkiss | Home - Noroton Yacht Club [Directions] | Postponed | ||
| Wed., 4/5 | V Girls Golf | Fairfield Warde | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Wed., 4/5 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Girls Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Girls Tennis | Hotchkiss (Scrim.) | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-2 | |
| Thu., 4/6 | V Boys Lacrosse | Brunswick School | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | W 12-11 | |
| Thu., 4/6 | JV Boys Lacrosse | Brunswick School | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | V Boys Volleyball | Shelton | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 4/6 | JV Boys Volleyball | Shelton | Home - Darien HS-DHS Main Gym [Directions] | 7:30 p.m. | ||
| Thu., 4/6 | V Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | 4:30 p.m. | L 3-12 | |
| Thu., 4/6 | JV Girls Tennis | Trumbull | Home - Weed Beach Tennis Courts [Directions] | Postponed | ||
| Sat., 4/8 | V Baseball | Sheehan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 11:00 a.m. | W 7-3 | |
| Sat., 4/8 | JV Baseball | Sheehan | Home - Darien HS-DHS Baseball - JV Field [Directions] | 11:00 a.m. | ||
| Sat., 4/8 | V Boys Lacrosse | Manhassett (NY) | Away - Manhasset Junior/Senior HS | 1:00 p.m. | L 2-11 | |
| Sat., 4/8 | JV Boys Lacrosse | Manhassett (NY) | Away - Manhasset Junior/Senior HS | 1:00 p.m. | ||
| Sat., 4/8 | V Girls Lacrosse | Summit (NJ) | Home - Darien HS-DHS Stadium Field [Directions] | 11:00 a.m. | W 14-8 | |
| Sat., 4/8 | JV Girls Lacrosse | Summit (NJ) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 11:00 a.m. | ||
| Sat., 4/8 | V Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 12:00 p.m. | L 0-10 | |
| Mon., 4/10 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | FR Boys Lacrosse | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | V Boys Volleyball | Cheshire | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/10 | JV Boys Volleyball | Cheshire | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 4/10 | V Girls Lacrosse | Garden City (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 11:00 a.m. | W 20-9 | |
| Mon., 4/10 | JV Girls Lacrosse | Garden City (NY) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 4/10 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 3-2 | |
| Mon., 4/10 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 11:00 a.m. | W 7-0 [Detailed Results] | |
| Tue., 4/11 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | W 16-4 | |
| Tue., 4/11 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | FR Boys Lacrosse | Kellenberg Memorial (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 11:00 a.m. | ||
| Tue., 4/11 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:30 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/11 | V Girls Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | W 20-1 | |
| Tue., 4/11 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 11:30 a.m. | ||
| Tue., 4/11 | V Girls Tennis | Westhill | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/12 | FR Baseball | Westhill | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/12 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 11:00 a.m. | ||
| Wed., 4/12 | V Boys Tennis | Norwalk | Home - Darien HS-DHS Tennis Courts [Directions] | 10:00 a.m. | W 7-0 [Detailed Results] | |
| Wed., 4/12 | V Softball | Ridgefield | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 10-1 | |
| Thu., 4/13 | V Baseball | Stratford | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 1:00 p.m. | W 11-1 | |
| Thu., 4/13 | JV Baseball | Stratford | Home - Darien HS-DHS Baseball - JV Field [Directions] | 1:00 p.m. | ||
| Thu., 4/13 | V Boys Lacrosse | Chaminade (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | L 7-17 | |
| Thu., 4/13 | JV Boys Lacrosse | Chaminade (NY) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 1:00 p.m. | ||
| Thu., 4/13 | FR Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 10:30 a.m. | ||
| Thu., 4/13 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/13 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 10:00 a.m. | W 3-0 | |
| Thu., 4/13 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 4/13 | V Girls Lacrosse | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | W 18-3 | |
| Thu., 4/13 | JV Girls Lacrosse | Staples | Home - Darien HS-DHS Center Oval - Turf [Directions] | 11:30 a.m. | ||
| Thu., 4/13 | V Girls Tennis | Trumbull | Home - Darien HS-DHS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 [Detailed Results] | |
| Fri., 4/14 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | W 5-4 | |
| Fri., 4/14 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | FR Baseball | Norwalk | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | FR Boys Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 12:00 p.m. | ||
| Fri., 4/14 | V Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Fri., 4/14 | JV Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 4/14 | V Softball | Norwalk | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 9-8 | |
| Sat., 4/15 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | L 11-13 | |
| Sat., 4/15 | JV Boys Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 4/15 | V Girls Lacrosse | St. Paul School for Girls (MD) | Away - St. Paul School for Girl's | 1:00 p.m. | W 13-12 | No bus needed |
| Mon., 4/17 | V Baseball | Westhill | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 11-8 | |
| Mon., 4/17 | JV Baseball | Westhill | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Boys Lacrosse | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Tennis | Fairfield Ludlowe | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/17 | JV Boys Tennis | Fairfield Ludlowe | Home - Weed Beach Tennis Courts [Directions] | 4:30 p.m. | ||
| Mon., 4/17 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/17 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Co-ed Sailing | Greenwich Academy | Away - Greenwich Academy | 3:00 p.m. | ||
| Mon., 4/17 | V Girls Golf | Ridgefield | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/17 | JV Girls Golf | Ridgefield | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/17 | FR Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Mon., 4/17 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 10-6 | |
| Mon., 4/17 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Tue., 4/18 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Tue., 4/18 | V Boys Outdoor Track | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/18 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Golf | Danbury | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 4/18 | JV Girls Golf | Danbury | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Tennis | Brien McMahon | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/18 | JV Girls Tennis | Staples | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Baseball | Trumbull | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 10-0 | |
| Wed., 4/19 | JV Baseball | Trumbull | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | FR Boys Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/19 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/19 | V Co-ed Sailing | Greenwich, Fairfield Ludlowe | Away - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/19 | V Girls Golf | New Canaan | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Wed., 4/19 | FR Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | L 5-0 | |
| Thu., 4/20 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | W 15-6 | |
| Thu., 4/20 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/20 | V Boys Rugby | Fairfield Prep | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Bridgeport Central | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/20 | JV Boys Tennis | New Canaan | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Girls Lacrosse | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 18-11 | |
| Thu., 4/20 | JV Girls Lacrosse | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 4/20 | V Girls Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/20 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/21 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | W 8-3 | |
| Fri., 4/21 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | FR Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Boys Outdoor Track | B Track @ CT Distance Festival- Xavier HS- MIddletown | Away - Not Listed | 5:00 p.m. | ||
| Fri., 4/21 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Boys Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/21 | JV Boys Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/21 | FR Girls Lacrosse | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Softball | Fairfield Ludlowe | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 18-0 | |
| Sat., 4/22 | V Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 10:30 a.m. | L 7-18 | |
| Sat., 4/22 | JV Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS | 2:30 p.m. | ||
| Sat., 4/22 | FR Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Gym | 10:30 a.m. | ||
| Sat., 4/22 | V Co-ed Sailing | Greenwich Country Day | Away - Indian Harbor Yacht Club | 2:30 p.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Warde Melville (NY) | Away - Ward Melville HS | 10:00 a.m. | W 12-5 | |
| Sat., 4/22 | JV Girls Lacrosse | Warde Melville (NY) | Away - Ward Melville HS | 12:00 p.m. | ||
| Mon., 4/24 | V Baseball | Brien McMahon | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 5-2 | |
| Mon., 4/24 | JV Baseball | Brien McMahon | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | FR Baseball | Bethel | Away - Bethel HS-MS Turf baseball field [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/24 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/24 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/24 | V Girls Golf | Wilton | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/24 | JV Girls Golf | Wilton | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/24 | FR Girls Lacrosse | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 4/24 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | L 6-2 | |
| Mon., 4/24 | V Girls Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Mon., 4/24 | JV Girls Tennis | Staples | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Lacrosse | Norwalk | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 23-0 | |
| Tue., 4/25 | JV Boys Lacrosse | Norwalk | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/25 | V Boys Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | L 4-3 [Detailed Results] | |
| Tue., 4/25 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Tue., 4/25 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/25 | JV Girls Golf | New Canaan | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | W 19-4 | |
| Tue., 4/25 | JV Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | ||
| Tue., 4/25 | FR Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-2nd Field | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Greenwich | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Tue., 4/25 | JV Girls Tennis | Greenwich | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:00 p.m. | W 15-4 | |
| Wed., 4/26 | FR Boys Lacrosse | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 4/26 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/26 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Co-ed Sailing | Greenwich | Away - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/26 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/26 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 11-6 | |
| Wed., 4/26 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Wed., 4/26 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Softball | Bridgeport Central | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 26-0 | |
| Wed., 4/26 | JV Girls Tennis | Fairfield Ludlowe | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/27 | V Boys Lacrosse | Yorktown (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 4:15 p.m. | W 11-6 | |
| Thu., 4/27 | JV Boys Lacrosse | Yorktown (NY) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:15 p.m. | ||
| Thu., 4/27 | JV Boys Tennis | Fairfield Warde | Home - Weed Beach Tennis Courts [Directions] | Postponed | ||
| Thu., 4/27 | V Girls Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | Canceled | Cancelled | |
| Thu., 4/27 | V Girls Rugby | Staples, Fairfield Ludlowe | Away - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/27 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | Postponed | ||
| Fri., 4/28 | V Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 2-1 | |
| Fri., 4/28 | JV Baseball | Staples | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Boys Lacrosse | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away - Danbury HS-Stadium Track | 5:00 p.m. | ||
| Fri., 4/28 | V Boys Tennis | Danbury | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/28 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 4/28 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 4/28 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Fri., 4/28 | V Girls Outdoor Track | O'Grady Relays @ Danbury HS | Away - Danbury HS-Stadium Track | 5:00 p.m. | ||
| Fri., 4/28 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 8-2 | |
| Fri., 4/28 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/29 | V Boys Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | W 11-7 | |
| Sat., 4/29 | JV Boys Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Sat., 4/29 | V Boys Rugby | Fairfield Ludlowe | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 3:00 p.m. | ||
| Sat., 4/29 | JV Girls Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS | Postponed | ||
| Mon., 5/1 | V Baseball | Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | L 4-3 | |
| Mon., 5/1 | JV Baseball | Greenwich | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:30 p.m. | ||
| Mon., 5/1 | FR Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 5/1 | V Boys Outdoor Track | Bassick, Bridgeport Central, Harding | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Boys Tennis | St. Joseph | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/1 | V Boys Volleyball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/1 | JV Boys Volleyball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/1 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | FR Girls Lacrosse | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Canceled | Cancelled | |
| Mon., 5/1 | V Girls Outdoor Track | Bassick, Bridgeport Central, Greenwich Academy, Harding | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Softball | Greenwich | Away - Bruce Park Field [Directions] | 4:30 p.m. | L 6-3 | |
| Mon., 5/1 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/1 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Boys Tennis | New Canaan | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 5/2 | JV Girls Golf | Greenwich | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 5/2 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Wed., 5/3 | V Baseball | Danbury | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:15 p.m. | L 10-4 | |
| Wed., 5/3 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/3 | FR Baseball | Danbury | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:15 p.m. | ||
| Wed., 5/3 | FR Boys Lacrosse | Newtown | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 4:30 p.m. | ||
| Wed., 5/3 | V Boys Volleyball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/3 | JV Boys Volleyball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/3 | V Co-ed Sailing | Sailing Gold Cup | Away - Grassy Hill Country Club | 3:00 p.m. | ||
| Wed., 5/3 | V Girls Golf | Greenwich | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | FR Girls Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Girls Rugby | Fairfield Ludlowe, Greenwich | Home - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Wed., 5/3 | V Softball | Danbury | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 9-4 | |
| Wed., 5/3 | JV Girls Tennis | New Canaan | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Lacrosse | Wilton | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | W 9-8 | |
| Thu., 5/4 | JV Boys Lacrosse | Wilton | Home - Darien HS-DHS Center Oval - Turf [Directions] | 6:00 p.m. | ||
| Thu., 5/4 | V Boys Rugby | B Rugby v Cobra | Home - Royle School Field [Directions] | Canceled | Cancelled | |
| Thu., 5/4 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/4 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Girls Golf | St. Joseph | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Thu., 5/4 | V Girls Lacrosse | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | W 17-7 | |
| Thu., 5/4 | JV Girls Lacrosse | Wilton | Home - Darien HS-DHS Stadium East [Directions] | 5:00 p.m. | ||
| Thu., 5/4 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Girls Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Thu., 5/4 | JV Girls Tennis | Ridgefield | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | L 13-5 | |
| Fri., 5/5 | JV Baseball | St. Joseph | Away - Madison MS-Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | FR Baseball | St. Joseph | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | FR Boys Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 5/5 | JV Boys Tennis | Fairfield Ludlowe | Home - Weed Beach Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 5/5 | V Boys Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/5 | JV Boys Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/5 | FR Girls Lacrosse | Greenwich Academy | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 3:30 p.m. | ||
| Fri., 5/5 | V Softball | St. Joseph | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 10-9 | |
| Sat., 5/6 | V Boys Lacrosse | Mamaroneck (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | W 13-8 | |
| Sat., 5/6 | JV Boys Lacrosse | Mamaroneck (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Sat., 5/6 | FR Boys Lacrosse | Connor Corish Tournament @ Don Bosco HS- NJ | Away - Not Listed | 4:00 p.m. | ||
| Sat., 5/6 | V Co-ed Sailing | TERK Trophy at MIT in Cambridge, MA (overnight event) | Away - MIT Sailing Pavilion | 9:00 a.m. | ||
| Sun., 5/7 | JV Boys Lacrosse | Lincoln-Sudbury (MA) (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Mon., 5/8 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 4-3 | |
| Mon., 5/8 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | FR Baseball | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | FR Boys Lacrosse | Stamford | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Stamford | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/8 | JV Boys Tennis | New Canaan | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 5/8 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 5/8 | V Girls Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 20-0 | |
| Mon., 5/8 | JV Girls Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 5/8 | V Softball | New Canaan | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 5-3 | |
| Mon., 5/8 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/9 | V Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | W 19-1 | |
| Tue., 5/9 | JV Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Tue., 5/9 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 4:30 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 5/9 | JV Boys Tennis | Wilton | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | JV Girls Golf | New Canaan | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 5/9 | V Girls Lacrosse | Massapequa (NY) | Away - Massapequa HS | 6:00 p.m. | W 17-6 | |
| Tue., 5/9 | V Girls Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Wed., 5/10 | V Baseball | Ridgefield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 5/10 | JV Baseball | Ridgefield | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Wed., 5/10 | V Boys Rugby | Staples | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/10 | JV Boys Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/10 | V Girls Golf | New Canaan | Away - TBA [Directions] | 3:30 p.m. | ||
| Wed., 5/10 | JV Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-2nd Field | 3:45 p.m. | ||
| Wed., 5/10 | FR Girls Lacrosse | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 5/10 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:30 p.m. | L 12-0 | |
| Thu., 5/11 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 6-5 | |
| Thu., 5/11 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | FR Baseball | Stamford | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | Chatham (NJ) | Away - Fairleigh Dickinson University Florham | 6:30 p.m. | W 8-6 | |
| Thu., 5/11 | JV Boys Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:30 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Thu., 5/11 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | W 3-1 | |
| Thu., 5/11 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/11 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:10 p.m. | ||
| Thu., 5/11 | FR Girls Lacrosse | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 5/11 | V Girls Outdoor Track | White Plains (NY) | Away - White Plains HS | 6:00 p.m. | ||
| Thu., 5/11 | V Softball | Stamford | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 2-1 | |
| Thu., 5/11 | V Girls Tennis | Fairfield Warde | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/11 | JV Girls Tennis | Fairfield Warde | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V | Unified Sports @ Fairfield Ludlowe | Away - Fairfield Ludlowe HS | 4:00 p.m. | ||
| Fri., 5/12 | FR Boys Lacrosse | Connor Corish Tournament @ Don Bosco HS- NJ | Away - Not Listed | 7:00 p.m. | ||
| Fri., 5/12 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | Miscellaneous Events | Prom | Home - TBA [Directions] | TBA | ||
| Sat., 5/13 | V Boys Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 15-2 | |
| Sat., 5/13 | JV Boys Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 5/13 | FR Boys Lacrosse | TENTATIVE Connor Corish Tournament @ Don Bosco HS- NJ | Away - Not Listed | 5:00 p.m. | ||
| Sat., 5/13 | V Co-ed Sailing | Sailing- ODay Qualifiers- Hothkiss- Lakeville, CT | Away - Hotchkiss School | 9:30 a.m. | ||
| Sun., 5/14 | V Co-ed Sailing | Tentative- Sailing- ODay Finals- Quincy Mass- | Away - Not Listed | 9:30 a.m. | ||
| Mon., 5/15 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | W 4-2 | |
| Mon., 5/15 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | FR Baseball | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Westhill | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-0 [Detailed Results] | |
| Mon., 5/15 | V Boys Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/15 | JV Boys Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Girls Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 20-8 | |
| Mon., 5/15 | JV Girls Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 5/15 | FR Girls Lacrosse | Ridgefield | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Softball | Wilton | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | L 2-8 | |
| Tue., 5/16 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/16 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/16 | JV Girls Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 5/16 | FR Girls Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Wed., 5/17 | V Baseball | Fairfield Warde | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 6-2 | |
| Wed., 5/17 | JV Baseball | Fairfield Warde | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Boys Lacrosse | Newtown | Home - Darien HS-DHS Center Oval - Turf [Directions] | Canceled | Cancelled | |
| Wed., 5/17 | V Boys Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 5/17 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Co-ed Sailing | Fairfield County Sailing League Championship Race | Home - Noroton Yacht Club [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Girls Golf | Fairfield Ludlowe | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | JV Girls Golf | Fairfield Ludlowe | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | L 12-0 | |
| Thu., 5/18 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | JV Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/18 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | V Girls Golf | Staples | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Thu., 5/18 | V Girls Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 19-1 | |
| Thu., 5/18 | FR Girls Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | V Girls Rugby | Southington | Away - Southington HS-7 Rugby/Lacrosse [Directions] | 6:30 p.m. | ||
| Thu., 5/18 | JV Softball | Stamford | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Fri., 5/19 | FR Baseball | Newtown | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | ||
| Fri., 5/19 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 6:00 p.m. | ||
| Fri., 5/19 | V Softball | Sacred Heart Academy | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:45 p.m. | L 7-8 | |
| Sat., 5/20 | V Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Sat., 5/20 | V Boys Rugby | vs West Hartford | Home - Royle School Field [Directions] | 11:00 a.m. | ||
| Sat., 5/20 | V Boys Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | ||
| Sun., 5/21 | V Co-ed Sailing | Connecticut State HS Fleet Racing Championship | Away - Black Rock Yacht Club | 9:30 a.m. | ||
| Mon., 5/22 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 5/22 | JV Girls Golf | Eckstrom Tournament @ Par 3 in Fairfield | Away - Carl Dickman Par 3 | 3:15 p.m. | ||
| Mon., 5/22 | V Girls Lacrosse | Greenwich | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | W 16-2 | |
| Tue., 5/23 | V Baseball | Stamford (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | V Boys Lacrosse | Wilton | Home - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | ||
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Track Championship | Away - Danbury HS-Danbury HS Stadium | 2:30 p.m. | ||
| Tue., 5/23 | V Boys Tennis | Greenwich | Away - Wilton HS-Wilton HS tennis courts [Directions] | 2:30 p.m. | ||
| Tue., 5/23 | V Girls Outdoor Track | FCIAC Track Championship | Away - Danbury HS-DHS Stadium | 2:30 p.m. | ||
| Tue., 5/23 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 5/23 | V Girls Tennis | New Canaan | Away - Wilton HS [Directions] | 4:00 p.m. | W 4-3 | |
| Wed., 5/24 | V Boys Volleyball | Westhill | Home - Fairfield Warde HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/24 | V Girls Lacrosse | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | W 11-8 | |
| Thu., 5/25 | V Girls Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Fri., 5/26 | V Boys Volleyball | Trumbull | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | ||
| Fri., 5/26 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/27 | V Boys Rugby | vs Mid-State | Away - . | 12:00 p.m. | ||
| Sat., 5/27 | V Boys Tennis | CIAC Class LL - First Round vs winner of Hamden/New Britain | Home - Darien HS-DHS Tennis Courts [Directions] | 11:00 a.m. | ||
| Sat., 5/27 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Tue., 5/30 | V Baseball | Xavier | Away - Palmer Field-Baseball Diamond [Directions] | 3:00 p.m. | W 7-5 | |
| Tue., 5/30 | V Boys Tennis | Fairfield Warde | Home - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 5/30 | V Girls Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 20-2 | |
| Tue., 5/30 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Wed., 5/31 | V Baseball | Westhill | Away - Cubeta Stadium [Directions] | 3:30 p.m. | L 4-0 | |
| Wed., 5/31 | V Boys Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 6:00 p.m. | ||
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class L Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 5/31 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | ||
| Wed., 5/31 | V Boys Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 [Detailed Results] | |
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 5/31 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Thu., 6/1 | V Girls Golf | Girls Golf FCIAC Tournament | Away - Fairchild Wheeler Golf Course | 12:00 p.m. | ||
| Thu., 6/1 | V Girls Lacrosse | Simsbury | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 6/2 | V Boys Volleyball | Enfield | Home - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | W 3-0 [Detailed Results] | |
| Sat., 6/3 | V Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open | Away - [CIAC] Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Boys Volleyball | Conard | Home - Fairfield Warde-Gym 1 [Directions] | 5:00 p.m. | W 3-0 [Detailed Results] | |
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Golf | CIAC Division I Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Volleyball | Trumbull | Home - Newtown HS-Gym [Directions] | 7:00 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Fri., 6/9 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Fri., 6/9 | V Girls Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | ||
| Sat., 6/10 | V Girls Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/10 | V Girls Outdoor Track | New England Championships | Away - . | TBA | No bus needed | |
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Lacrosse | New Canaan | Home - Sacred Heart University-Campus Field [Directions] | 6:00 p.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||