| Darien 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1130 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 8/24 | V Boys Golf | Wilton | Home - Woodway Country Club [Directions] | 3:15 p.m. | ||
| Thu., 8/24 | JV Boys Golf | Wilton | Home - Woodway Country Club [Directions] | 3:30 p.m. | ||
| Mon., 8/28 | V Boys Golf | Fairfield Warde | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Mon., 8/28 | JV Boys Golf | Fairfield Warde | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 8/29 | V Girls Soccer | Greens Farms Academy (Scrim.) | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:30 p.m. | ||
| Tue., 8/29 | JV Girls Soccer | Greens Farms Academy (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 8/30 | V Boys Soccer | St. Lukes (Scrim.) | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:30 p.m. | ||
| Wed., 8/30 | JV Boys Soccer | St. Lukes (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 8/30 | V Field Hockey | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | V Football | Trumbull (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | FR Football | Trumbull (Scrim.) | Away - Trumbull HS-Field 14 [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | V Boys Golf | Norwalk | Home - Woodway Country Club [Directions] | 3:15 p.m. | ||
| Thu., 8/31 | JV Boys Golf | New Canaan | Away - New Canaan HS-CCNC [Directions] | 3:15 p.m. | ||
| Thu., 8/31 | JV Field Hockey | Greenwich Country Day (Scrim.) | Away - Greenwich Country Day-Stadium | 4:00 p.m. | ||
| Fri., 9/1 | V Girls Soccer | Southington (Scrim.) | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:30 p.m. | ||
| Fri., 9/1 | JV Girls Soccer | Southington (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 9/2 | V Field Hockey | Play Day at Sacred Heart Academy- Greenwich | Away - Not Listed | 9:00 a.m. | ||
| Sat., 9/2 | V Girls Volleyball | Berlin, Bristol Eastern, Brookfield, Conard, East Lyme, TBA, Southington | Home - Darien HS-DHS Main Gym [Directions] | 8:30 a.m. | ||
| Tue., 9/5 | V Girls Soccer | Greenwich Academy (Scrim.) | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:30 p.m. | ||
| Tue., 9/5 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 9/6 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | Postponed | ||
| Wed., 9/6 | V Boys Soccer | Bassick (Scrim.) | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 6:00 p.m. | ||
| Wed., 9/6 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 4:15 p.m. | ||
| Thu., 9/7 | FR Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | 7:00 p.m. | ||
| Thu., 9/7 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 9/7 | JV Boys Golf | Brien McMahon | Away - Brien McMahon HS-Oak Hills Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 9/7 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 10-0 | |
| Thu., 9/7 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 9/7 | FR Field Hockey | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 6:00 p.m. | ||
| Fri., 9/8 | V Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | Forfeit | W 1-0 | |
| Fri., 9/8 | FR Boys Soccer | Norwalk | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Postponed | ||
| Fri., 9/8 | V Girls Swimming and Diving | St. Joseph | Home - Darien YMCA [Directions] | 3:00 p.m. | Darien 99 St. Joseph 63 | |
| Fri., 9/8 | V Girls Volleyball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/8 | JV Girls Volleyball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 9/9 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/9 | JV Football | North Haven | Home - Darien HS-DHS Stadium East [Directions] | Canceled | Cancelled | |
| Sat., 9/9 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 3:00 p.m. | T 1-1 | |
| Sat., 9/9 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 1:00 p.m. | ||
| Sat., 9/9 | V Girls Cross Country | Wilton Invitational | Away - Allen's Meadow | 9:00 a.m. | ||
| Sat., 9/9 | V Girls Soccer | Norwalk | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 9:00 a.m. | W 8-0 | |
| Sat., 9/9 | V Girls Volleyball | CIAC Girls' Volleyball Invitational | Away - CT Volleyball Center Woodbridge | 7:30 a.m. | ||
| Sat., 9/9 | V Girls Volleyball | CIAC Girls Volleyball Invitational- CT Volleyball Center, 21 S Bradley Rd, Woodbridge, CT | Away - Not Listed | 8:00 a.m. | ||
| Mon., 9/11 | V Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 9/11 | JV Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 9/11 | FR Field Hockey | Greenwich | Away - Greenwich HS-Field 4 [Directions] | Postponed | ||
| Tue., 9/12 | V Boys Cross Country | Trumbull, St. Joseph, Wilton | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 9/12 | JV Boys Golf | Fairfield Prep | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Westhill | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | T 2-2 | |
| Tue., 9/12 | JV Boys Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | FR Boys Soccer | Westhill | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Trumbull, St. Joseph, Wilton | Away - Trumbull HS-Cross Country Course [Directions] | 4:15 p.m. | ||
| Tue., 9/12 | V Girls Diving | Fairfield Ludlowe, Fairfield Warde | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/12 | JV Field Hockey | Sacred Heart of Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | FR Girls Soccer | Newtown | Away - Newtown HS-NHS Soccer Practice Fields [Directions] | 4:30 p.m. | ||
| Tue., 9/12 | V Girls Volleyball | Simsbury | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 9/12 | JV Girls Volleyball | Simsbury | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 9/13 | V Girls Soccer | Wilton | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | T 2-2 | |
| Wed., 9/13 | JV Girls Soccer | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | V Girls Swimming and Diving | Fairfield Warde | Home - Darien YMCA [Directions] | 3:00 p.m. | Darien 106 Fairfield Warde 68 | |
| Thu., 9/14 | FR Football | Wilton | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | ||
| Thu., 9/14 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:15 p.m. | L 1-0 | |
| Thu., 9/14 | JV Boys Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | ||
| Thu., 9/14 | FR Boys Soccer | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 3-1 | |
| Thu., 9/14 | JV Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 9/14 | FR Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | FR Girls Soccer | Wilton | Away - Allen's Meadow-Field #1 [Directions] | 4:15 p.m. | ||
| Thu., 9/14 | V Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 9/14 | FR Girls Volleyball | Brookfield | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/15 | V Football | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 3:30 p.m. | W 21-14 | |
| Mon., 9/18 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | ||
| Mon., 9/18 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 11-0 | |
| Mon., 9/18 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/18 | FR Field Hockey | Westhill | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 9/18 | V Girls Soccer | Stamford | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 9/18 | JV Girls Soccer | Stamford | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Westhill, Brien McMahon, Greenwich | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/19 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Stamford | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | L 2-1 | |
| Tue., 9/19 | JV Boys Soccer | Stamford | Away - Trinity Catholic-Alumni Field [Directions] | 4:30 p.m. | ||
| Tue., 9/19 | FR Boys Soccer | Stamford | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Westhill, Brien McMahon, Greenwich | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Diving | Staples | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/20 | V Boys Golf | Greenwich | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Wed., 9/20 | JV Boys Golf | Greenwich | Away - Greenwich Country Club [Directions] | 3:30 p.m. | ||
| Wed., 9/20 | V Field Hockey | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 10-0 | |
| Wed., 9/20 | JV Field Hockey | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 9/20 | V Girls Soccer | St. Joseph | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | L 6-1 | |
| Wed., 9/20 | JV Girls Soccer | St. Joseph | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Girls Swimming and Diving | Staples | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | FR Football | Fairfield Prep | Home - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 [Directions] | 4:15 p.m. | ||
| Thu., 9/21 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | JV Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 5 2 | |
| Fri., 9/22 | V Football | Fairfield Prep | Home - Darien HS-DHS Stadium Field [Directions] | 6:00 p.m. | W 10-2 | |
| Fri., 9/22 | JV Boys Soccer | Staples | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 4-0 | |
| Fri., 9/22 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | FR Girls Soccer | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/22 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/22 | FR Girls Volleyball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/23 | JV Football | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Girls Cross Country | Ocean State Invitational, Goddard State Park, RI | Away - Goddard Park | 12:45 p.m. | ||
| Sat., 9/23 | V Field Hockey | Skyline (MI) | Away - The Proving Grounds | 7:00 p.m. | W 12-4 | |
| Sun., 9/24 | V Field Hockey | Camden Catholic (NJ) | Away - The Proving Grounds | 1:00 p.m. | L 1-6 | |
| Tue., 9/26 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | JV Boys Golf | New Canaan | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 9/26 | V Field Hockey | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 9/26 | JV Field Hockey | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 9/26 | FR Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:30 p.m. | ||
| Tue., 9/26 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Cross Country | Danbury, Fairfield Ludlowe, Stamford | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Golf | Staples | Home - Woodway Country Club [Directions] | 3:30 p.m. | ||
| Wed., 9/27 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/27 | V Girls Cross Country | Danbury, Fairfield Ludlowe, Stamford | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 4-1 | |
| Wed., 9/27 | JV Girls Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | FR Girls Soccer | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/27 | JV Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/28 | FR Football | Trumbull | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Boys Golf | CIAC Fall Classic @ Orange Hills GC | Away - Not Listed | 2:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Trumbull | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | L 0 2 | |
| Thu., 9/28 | JV Boys Soccer | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 10-0 | |
| Thu., 9/28 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:15 p.m. | ||
| Thu., 9/28 | FR Field Hockey | Fairfield Warde | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | Canceled | Cancelled | |
| Thu., 9/28 | V Girls Swimming and Diving | Wilton | Away - New Canaan Y -Diving Only [Directions] | 2:00 p.m. | ||
| Thu., 9/28 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Fri., 9/29 | V Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 49-7 | |
| Fri., 9/29 | V Girls Soccer | Bridgeport Central | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:30 p.m. | W 8-0 | |
| Fri., 9/29 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 9/29 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Sat., 9/30 | V Boys Cross Country | B Cross Country Meet @ New York State Night Time Showcase- Hudson Valley Sports Dome, Milton NY | Away - Not Listed | Canceled | Cancelled | |
| Sat., 9/30 | JV Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 2:30 p.m. | ||
| Sat., 9/30 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 2 0 | |
| Sat., 9/30 | JV Boys Soccer | Bridgeport Central | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:30 p.m. | ||
| Sat., 9/30 | V Girls Volleyball | John Jay (NY) | Away - John Jay HS (Crossriver)-Gym | 9:00 a.m. | ||
| Mon., 10/2 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Mon., 10/2 | V Boys Soccer | Staples | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | T 1 1 | |
| Mon., 10/2 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Field Hockey | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 10/2 | JV Field Hockey | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 10/2 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | FR Girls Volleyball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Staples, Bridgeport Central, Norwalk | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Golf | Fairfield Prep | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 10/3 | JV Boys Golf | Greenwich | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Staples, Bridgeport Central, Norwalk | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Diving | New Canaan | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Girls Soccer | New Canaan | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/3 | JV Girls Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | FR Girls Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/3 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | FR Girls Volleyball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Boys Golf | Fairfield Prep | Away - Patterson Club [Directions] | 3:00 p.m. | ||
| Wed., 10/4 | JV Boys Golf | Fairfield Prep | Home - Wee Burn CC [Directions] | Postponed | ||
| Wed., 10/4 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | T 1-1 | |
| Wed., 10/4 | JV Boys Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | FR Boys Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 7:00 p.m. | W 2-1 | |
| Wed., 10/4 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Wed., 10/4 | FR Field Hockey | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Girls Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 10/5 | FR Football | Fairfield Ludlowe | Home - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Boys Golf | CHAPPA Tournament @ Longshore- Westport | Away - Longshore Golf Course | 3:15 p.m. | ||
| Thu., 10/5 | JV Field Hockey | Sacred Heart of Greenwich | Away - Sacred Heart Greenwich-Stadium 2 | 4:00 p.m. | ||
| Thu., 10/5 | FR Girls Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 10/5 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/5 | FR Girls Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | V Boys Soccer | Greenwich | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:30 p.m. | W 1-0 | |
| Fri., 10/6 | JV Boys Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | L 5-2 | |
| Fri., 10/6 | JV Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/7 | V Girls Cross Country | Wickham Invitational at Wickham Park, East Hartford | Away - Wickham Park | Canceled | Cancelled | |
| Sat., 10/7 | FR Girls Soccer | Ridgefield | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 10/7 | V Girls Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 2:00 p.m. | W 3-0 | |
| Sat., 10/7 | JV Girls Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 10/9 | V Field Hockey | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 4-1 | |
| Mon., 10/9 | JV Field Hockey | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 10/9 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:00 p.m. | W 1-0 | |
| Mon., 10/9 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Grass Utility Field [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | FR Girls Soccer | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | V Girls Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/9 | JV Girls Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Cross Country | Fairfield Warde, New Canaan, Ridgefield | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Fairfield Warde | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/10 | JV Boys Soccer | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | Fairfield Warde, New Canaan, Ridgefield | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Girls Diving | Greenwich | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/10 | FR Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:15 p.m. | ||
| Tue., 10/10 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 10/11 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | W 9-1 | |
| Wed., 10/11 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:30 p.m. | ||
| Wed., 10/11 | V Girls Swimming and Diving | Greenwich | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/11 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | ||
| Thu., 10/12 | V Boys Golf | Stamford | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Thu., 10/12 | JV Boys Golf | Greenwich | Home - Woodway Country Club [Directions] | 3:10 p.m. | ||
| Thu., 10/12 | JV Field Hockey | Greenwich Academy | Away - Greenwich Academy-Turf field | 5:00 p.m. | ||
| Thu., 10/12 | V Girls Soccer | Danbury | Home - Darien HS-DHS Stadium Field [Directions] | 6:00 p.m. | W 6-1 | |
| Thu., 10/12 | JV Girls Soccer | Danbury | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | FR Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 3:45 p.m. | L 2-1 | |
| Fri., 10/13 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/13 | FR Boys Soccer | Danbury | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 10/13 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/13 | FR Field Hockey | Greenwich Academy | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:30 p.m. | ||
| Fri., 10/13 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/13 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | FR Girls Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/14 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | L 14-30 | |
| Sat., 10/14 | V Competitive Cheerleading | Greenwich | Away - Greenwich HS [Directions] | 2:00 p.m. | ||
| Sat., 10/14 | JV Girls Soccer | Norwalk | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Mon., 10/16 | JV Football | Greenwich | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | JV Boys Golf | Brien McMahon | Away - Brien McMahon HS-Oak Hills Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 10/16 | JV Field Hockey | Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | FR Field Hockey | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/16 | V Girls Soccer | Fairfield Ludlowe | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/16 | JV Girls Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 10/16 | JV Girls Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/16 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Golf | Holahan- Woodway CC | Home - Woodway Country Club [Directions] | 3:15 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 1-0 | |
| Tue., 10/17 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | FR Boys Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | JV Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 6:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | JV Boys Golf | Staples | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Field Hockey | Trumbull | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 10-2 | |
| Wed., 10/18 | JV Field Hockey | Trumbull | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 10/18 | FR Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | Canceled | Cancelled | |
| Wed., 10/18 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 2-1 | |
| Wed., 10/18 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Wed., 10/18 | V Girls Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/18 | JV Girls Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/19 | FR Football | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Boys Golf | FCIAC Tournament | Away - Not Listed | TBA | ||
| Thu., 10/19 | V Boys Soccer | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | W 2-1 | |
| Thu., 10/19 | JV Boys Soccer | Ridgefield | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Field Hockey | Greenwich Academy | Away - Greenwich Academy - Everett Field | 5:00 p.m. | ||
| Fri., 10/20 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | W 10-0 | |
| Fri., 10/20 | JV Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 10/20 | V Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 10/20 | JV Girls Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | JV Girls Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/20 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/20 | FR Girls Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/21 | V Football | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | W 34-21 | |
| Sat., 10/21 | FR Girls Soccer | Newtown | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 10/23 | JV Football | Fairfield Ludlowe | Away - Tomlinson MS-Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 10/23 | V Field Hockey | Taft (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Mon., 10/23 | JV Field Hockey | Greenwich Academy | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | Cancelled | |
| Mon., 10/23 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:15 p.m. | T 1-1 | |
| Mon., 10/23 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/23 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/23 | FR Girls Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Boys Golf | CIAC Division I Fall Championship | Away - Stanley GC | 8:30 a.m. | ||
| Tue., 10/24 | V Boys Soccer | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | T 2-2 | |
| Tue., 10/24 | JV Boys Soccer | Brien McMahon | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | ||
| Wed., 10/25 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 6:00 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/25 | JV Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/25 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Greenwich | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | V Girls Cross Country | Freshman Meet (2.00 miles) | Away - Tarrywile Park | 4:00 p.m. | ||
| Thu., 10/26 | FR Field Hockey | Danbury | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | W 2-0 | |
| Fri., 10/27 | V Football | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | L 10-24 | |
| Fri., 10/27 | V Field Hockey | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Fri., 10/27 | V Girls Volleyball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/27 | JV Girls Volleyball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/28 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/28 | JV Football | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:05 p.m. | ||
| Sat., 10/28 | JV Girls Swimming and Diving | Greenwich, Danbury, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 9:30 a.m. | ||
| Sat., 10/28 | JV Girls Volleyball | Fairfield Warde, Brien McMahon, Fairfield Ludlowe, Greenwich Country Day, Greenwich, Shelton, Stamford, Trumbull, Weston | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Sat., 10/28 | FR Girls Volleyball | Frosh Volleyball End of Season Tournament- Southington | Away - Southington HS-Gym 1 | 9:00 a.m. | ||
| Sat., 10/28 | Miscellaneous Events | women's lax scrimmage Michigan v BC | Home - Darien HS-DHS Stadium Field [Directions] | 11:30 a.m. | ||
| Mon., 10/30 | V Field Hockey | Greenwich | Home - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Tue., 10/31 | V Boys Soccer | New Canaan (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/31 | V Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 11/1 | V Field Hockey | Greenwich | Home - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | ||
| Wed., 11/1 | V Girls Soccer | Staples | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Wed., 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 | 5:30 p.m. | ||
| Thu., 11/2 | FR Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/2 | V Girls Volleyball | Westhill | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 11/3 | V Football | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 49-6 | |
| Fri., 11/3 | V Field Hockey | Staples | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | ||
| Sat., 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 | 3:30 p.m. | ||
| Sat., 11/4 | V Girls Volleyball | Trumbull | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Maloney | Home - Darien HS-DHS Stadium Field [Directions] | 4:45 p.m. | ||
| Tue., 11/7 | V Boys Soccer | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 2:00 p.m. | ||
| Wed., 11/8 | SO Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 3:30 p.m. | ||
| Wed., 11/8 | V Field Hockey | South Windsor | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 11/8 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 6:00 p.m. | ||
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class L Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/9 | FR Football | Danbury | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Thu., 11/9 | V Girls Volleyball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 11/9 | Miscellaneous Events | Unified Sports @ Ludlowe HS | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 3:00 p.m. | ||
| Fri., 11/10 | V Field Hockey | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Sat., 11/11 | V Football | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 11:00 a.m. | W 45-6 | |
| Sat., 11/11 | V Competitive Cheerleading | Cheer @ Bridgeport Central | Away - Not Listed | 11:00 a.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 11:15 a.m. | ||
| Sat., 11/11 | V Girls Volleyball | Cheshire | Home - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | ||
| Mon., 11/13 | JV Football | Iona Prep (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 11/14 | V Field Hockey | Wilton | Home - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Wed., 11/15 | SO Football | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Wed., 11/15 | V Girls Volleyball | Trumbull | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/16 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/17 | JV Football | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Sat., 11/18 | V Field Hockey | Staples | Home - Wethersfield HS-Cottone Field [Directions] | 11:00 a.m. | ||
| Sat., 11/18 | V Girls Volleyball | Southington | Home - East Haven HS-Gym [Directions] | 6:00 p.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Thu., 11/23 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | L 17-31 | |
| Thu., 11/23 | V Competitive Cheerleading | New Canaan | Away - New Canaan HS [Directions] | 10:00 a.m. | ||
| Sat., 11/25 | V Boys Rugby | B Rugby Alumni Game | Home - Darien HS-DHS Tennis Court Field [Directions] | 11:00 a.m. | ||
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 6:30 p.m. | W 42-28 | |
| Tue., 11/28 | V Competitive Cheerleading | Naugatuck | Away - Naugatuck HS [Directions] | 6:30 p.m. | ||
| Fri., 12/1 | V Girls Basketball | King and Low-Heywood Thomas (Scrim.) | Away - King School-Gym | 4:15 p.m. | ||
| Sat., 12/2 | V Boys Ice Hockey | Scrimmage v Marshfield Mass. | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | ||
| Sat., 12/2 | V Girls Ice Hockey | New Canaan (Scrim.) | Away - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | ||
| Sat., 12/2 | V Girls Squash | G V Squash v Episcopal | Home - MSquash [Directions] | 11:00 a.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Sun., 12/3 | V Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 12:30 p.m. | W 21-0 | |
| Mon., 12/4 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | W 6-0 | |
| Tue., 12/5 | FR Girls Basketball | Cardinal Kung Academy (Scrim.) | Home - MIDDLESEX MIDDLE SCHOOL-Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/5 | V Girls Squash | G V Squash v New Canaan | Away - Chelsea Piers - Field Side-Chelsea Piers Connecticut | 7:00 p.m. | ||
| Tue., 12/5 | JV Girls Squash | JV G Squash v Briarcliff V | Home - MSquash [Directions] | 8:00 p.m. | ||
| Thu., 12/7 | V Boys Squash | B V Squash v Westport Boys @ Chelsea Piers | Away - Chelsea Piers - Field Side-Chelsea Piers Connecticut | 7:00 p.m. | ||
| Thu., 12/7 | JV Boys Squash | B JV Squash v Fairfield Boys/Mixed | Home - MSquash [Directions] | 8:00 p.m. | ||
| Thu., 12/7 | V Girls Basketball | Lauralton Hall (Scrim.) | Away - Lauralton Hall-Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/8 | V Boys Basketball | Bullard Havens Tech (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/8 | V Boys Ice Hockey | Xaverian Brothers (MA) (Scrim.) | Away - Canton Ice House | 5:00 p.m. | ||
| Sat., 12/9 | V Football | New Canaan | Home - Rentschler Field [Directions] | 1:30 p.m. | L 21-28 | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Boys Ice Hockey | St. Johns Prep (MA) (Scrim.) | Away - Essex Sports Center - Middleton-Ice Rink | 10:20 a.m. | ||
| Sat., 12/9 | JV Boys Ice Hockey | New Canaan (Scrim.) | Home - Darien Ice House-Ice Rink [Directions] | 7:40 p.m. | ||
| Sat., 12/9 | V Wrestling | Suffield Windsor Locks Wrestling Co Op, Canton, Coventry, Granby Memorial, Lyman Memorial/Windham Tech, Rockville | Away - Suffield HS | 12:30 p.m. | ||
| Sat., 12/9 | V Competitive Cheerleading | New Canaan | Away - Rentschler Field [Directions] | 1:30 p.m. | ||
| Sat., 12/9 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 7-0 | |
| Mon., 12/11 | V Boys Squash | B V Squash v Bronxville Boys V @ Chelsea Piers | Away - Chelsea Piers - Field Side-Chelsea Piers Connecticut | 8:00 p.m. | ||
| Mon., 12/11 | V Girls Basketball | Joel Barlow | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 39-31 | |
| Mon., 12/11 | JV Girls Basketball | Joel Barlow | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 38-34 | |
| Mon., 12/11 | V Girls Squash | G V Squash v Westport Girls | Home - MSquash [Directions] | 7:30 p.m. | ||
| Wed., 12/13 | V Wrestling | Trumbull | Away - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/14 | V Boys Diving | Greenwich, Wilton | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 12/14 | V Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 41-31 | |
| Thu., 12/14 | JV Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 4:15 p.m. | W 37-17 | |
| Thu., 12/14 | JV Girls Squash | G JV Squash v Greenwich Girls B @ Field Club Greenwich- 276 Lake Ave, Greenwich | Away - Not Listed | 7:30 p.m. | ||
| Fri., 12/15 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 12/15 | V Boys Indoor Track | Coach Saint Invite- Armory- 216 Fort Washington Ave, New York, NY 10032 | Away - NYC Armory | 5:00 p.m. | ||
| Fri., 12/15 | V Boys Swimming and Diving | Greenwich | Home - Darien YMCA [Directions] | 3:00 p.m. | Greenwich 108 Darien 80 | |
| Fri., 12/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 12/15 | V Girls Indoor Track | Coach Saint Invite- The Armory- 216 Fort Washington Ave, New York, NY 10032 | Away - NYC Armory | 5:00 p.m. | ||
| Sat., 12/16 | V Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 2:00 p.m. | W 60-55 | |
| Sat., 12/16 | JV Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 12:15 p.m. | ||
| Sat., 12/16 | FR Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 10:30 a.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Northwest Catholic | Away - Simsbury - ISCC-NHL [Directions] | 6:30 p.m. | L 1-3 | |
| Sat., 12/16 | V Boys Indoor Track | Wilton, Brien McMahon, Fairfield Warde, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:30 p.m. | ||
| Sat., 12/16 | V Wrestling | Darien Invitational | Home - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | 7:00 p.m. | W 4-0 | |
| Sat., 12/16 | V Girls Indoor Track | Wilton, Brien McMahon, Fairfield Warde, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:30 p.m. | ||
| Sat., 12/16 | Miscellaneous Events | DHS g basketball to UCONN women's basketball game- 1 Civic Center Plaza, Hartford | Home - TBA [Directions] | 12:00 p.m. | ||
| Mon., 12/18 | V Boys Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 91-70 | |
| Mon., 12/18 | JV Boys Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/18 | FR Boys Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/18 | V Boys Diving | Westhill | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Mon., 12/18 | V Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 5:30 p.m. | W 50-43 | |
| Mon., 12/18 | JV Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 4:00 p.m. | W 49-14 | |
| Tue., 12/19 | V Boys Swimming and Diving | Westhill/Stamford | Home - Darien YMCA [Directions] | 3:00 p.m. | Darien 113 Westhill/Stamford 70 | |
| Tue., 12/19 | V Girls Ice Hockey | Southington Coop | Home - Darien Ice House-Ice Rink [Directions] | 7:20 p.m. | W 5-0 | |
| Wed., 12/20 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 12/20 | V Wrestling | Westhill | Home - Darien HS-DHS South Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/20 | V Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 31-16 | |
| Wed., 12/20 | JV Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 31-17 | |
| Thu., 12/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 7:10 p.m. | W 6-0 | |
| Fri., 12/22 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Stamford Twin Rinks-West [Directions] | Postponed | ||
| Fri., 12/22 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 63-39 | |
| Fri., 12/22 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 40-33 | |
| Fri., 12/22 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | Northern Highlands (NJ) | Away - Sport-O-Rama-Rink Two | 11:00 a.m. | W 4-2 | |
| Sat., 12/23 | V Girls Indoor Track | North Shore Invitational- NYC Armory | Away - NYC Armory | 9:00 a.m. | ||
| Wed., 12/27 | V Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 3:00 p.m. | L 69-60 | |
| Wed., 12/27 | JV Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 1:30 p.m. | ||
| Wed., 12/27 | FR Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 12:00 p.m. | ||
| Wed., 12/27 | V Boys Ice Hockey | Pilgrim (RI) | Away - Pilgrim HS | 1:00 p.m. | W 3-2 | |
| Wed., 12/27 | V Wrestling | Ryan Sabbagh Holiday Tournament | Away - Danbury HS | 9:00 a.m. | ||
| Thu., 12/28 | V Boys Indoor Track | Relay Rust Buster- Southern CT State U- New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Thu., 12/28 | V Girls Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 12:00 p.m. | W 58-33 | |
| Thu., 12/28 | V Girls Indoor Track | Relay Rust Buster- Southern CT State U- New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Fri., 12/29 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 1:00 p.m. | L 63-50 | |
| Fri., 12/29 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 11:30 a.m. | ||
| Fri., 12/29 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 10:15 a.m. | ||
| Fri., 12/29 | V Boys Ice Hockey | Greenwich | Away - Greenwich Skating Club-Ice Rink [Directions] | 4:00 p.m. | W 5-3 | |
| Fri., 12/29 | JV Boys Ice Hockey | Greenwich | Away - Greenwich Skating Club-Ice Rink [Directions] | 10:00 a.m. | ||
| Fri., 12/29 | V Wrestling | Trumbull, Brien McMahon, Fairfield Warde, Greenwich, Masuk, TBA, New Canaan, New Fairfield, New Milford, Newtown, Ridgefield, Simsbury, Stamford, Staples, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Sat., 12/30 | V Wrestling | Fairfield Warde, Brien McMahon, Norwalk | Away - Fairfield Warde HS-Small Gym [Directions] | 10:00 a.m. | ||
| Tue., 1/2 | V Boys Basketball | Masuk | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 66-49 | |
| Tue., 1/2 | JV Boys Basketball | Masuk | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/2 | FR Boys Basketball | Masuk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | L 44-35 | |
| Wed., 1/3 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice House-Ice Rink [Directions] | 7:20 p.m. | W 7-2 | |
| Thu., 1/4 | V Boys Indoor Track | Wintergreen Invitational- Southern CT State U- New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Thu., 1/4 | V Wrestling | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/4 | V Girls Indoor Track | Wintergreen Invitational- Southern CT State U- New Haven | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Fri., 1/5 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | L 60-58 | |
| Fri., 1/5 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | JV Boys Ice Hockey | Fairfield Prep | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 37-29 | |
| Fri., 1/5 | JV Girls Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/6 | V Boys Indoor Track | Wilton, New Canaan, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/6 | V Boys Squash | V B Squash v Squash Haven @ Yale U- 70 Tower Pkwy, New Haven, CT | Away - Yale University New Haven CT-Other | 12:00 p.m. | ||
| Sat., 1/6 | V Wrestling | Somers NY Duals @ Somers HS, NY | Away - Not Listed | 9:00 a.m. | ||
| Sat., 1/6 | V Girls Gymnastics | TBA, Trumbull | Away - TBA-Albermale Field | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Next Dimension Gymnastics-Next Dimension | ||||||
| Sat., 1/6 | V Girls Gymnastics | St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 4:30 p.m. | ||
| Sat., 1/6 | V Girls Indoor Track | Wilton, New Canaan, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/6 | V Girls Squash | G V Squash v Squash Haven- Yale U, 70 Tower Pkwy, New Haven | Away - Yale University New Haven CT-Other | 12:00 p.m. | ||
| Mon., 1/8 | V Boys Diving | Norwalk | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Mon., 1/8 | V Boys Squash | V B Squash v Scarsdale Boys/Mixed V @ Westchester Squash Academy 628 Fayette Ave, Mamaroneck, NY | Away - Not Listed | 8:00 p.m. | ||
| Mon., 1/8 | V Girls Squash | V G Squash v Rye Girls V | Home - MSquash [Directions] | 7:30 p.m. | ||
| Tue., 1/9 | V Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 5:15 p.m. | W 59-51 | |
| Tue., 1/9 | JV Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | JV Wrestling | Fairfield Ludlowe, Branford | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | W 42-23 | |
| Tue., 1/9 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/10 | V Wrestling | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 1/10 | V Girls Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | W 1-0 | |
| Thu., 1/11 | JV Boys Ice Hockey | Xavier | Away - Wesleyan University-Freeman Athletic Center [Directions] | 4:30 p.m. | ||
| Thu., 1/11 | V Co-ed Alpine Skiing | practice | Away - Mt. Southingon Ski Area | 4:40 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 70-69 | |
| Fri., 1/12 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | JV Boys Ice Hockey | New Canaan | Away - New Canaan Winter Club-Rink [Directions] | 6:00 p.m. | ||
| Fri., 1/12 | V Boys Indoor Track | Yale Invitational @ Coxe Cage- Yale U- New Haven | Away - Yale University New Haven CT-Coxe Cage | 1:00 p.m. | ||
| Fri., 1/12 | V Boys Swimming and Diving | Danbury | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 1/12 | V Wrestling | Weston | Away - Weston HS-Gym (New) [Directions] | 6:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 51-38 | |
| Fri., 1/12 | JV Girls Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Indoor Track | Yale Invitational @ Coxe Cage- Yale U- New Haven | Away - Yale University New Haven CT-Coxe Cage | 1:00 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 4:15 p.m. | W 4-3 (OT) | |
| Sat., 1/13 | V Boys Indoor Track | Staples, Bridgeport Central, Danbury, Greenwich, St. Joseph, Stamford, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/13 | V Boys Indoor Track | Yale Invitational @ Coxe Cage- Yale U- New Haven | Away - Yale University New Haven CT-Coxe Cage | TBA | ||
| Sat., 1/13 | V Girls Ice Hockey | Hall/Conard | Home - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | W 6-1 | |
| Sat., 1/13 | V Girls Indoor Track | Staples, Bridgeport Central, Danbury, Greenwich, St. Joseph, Stamford, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Yale Invitational @ Coxe Cage- Yale U- New Haven | Away - Yale University New Haven CT-Coxe Cage | TBA | ||
| Mon., 1/15 | V Boys Ice Hockey | Xavier | Home - Darien Ice House-Ice Rink [Directions] | 3:20 p.m. | W 6-1 | |
| Mon., 1/15 | V Girls Gymnastics | Trumbull, St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 7:00 p.m. | Darien 135.85 Trumbull 146.95 St. Joes 78.75 | |
| Mon., 1/15 | V Girls Ice Hockey | Southington Coop | Away - Newington-Red Rink [Directions] | 4:00 p.m. | W 5-1 | |
| Wed., 1/17 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 63-59 | |
| Wed., 1/17 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 4-2 | |
| Wed., 1/17 | V Wrestling | New Canaan | Home - Darien HS-DHS South Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/17 | V Co-ed Alpine Skiing | practice | Home - Mt. Southingon Ski Area [Directions] | 4:40 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 60-30 | |
| Wed., 1/17 | JV Girls Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Girls Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 2-1 | |
| Thu., 1/18 | V Girls Gymnastics | Norwalk | Away - Westport YMCA [Directions] | 7:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 p.m. | ||||||
| Thu., 1/18 | V Girls Gymnastics | Staples | Away - Staples HS-Westport YMCA [Directions] | 7:30 p.m. | Darien 128.9 Staples 135.1 Norwalk 109.15 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 p.m. | ||||||
| Fri., 1/19 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 73-65 | |
| Fri., 1/19 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | JV Boys Ice Hockey | Greenwich | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 1/19 | V Boys Squash | V B Squash v Rye Country Day School- 3 Cedar St, Rye NY | Away - Not Listed | 6:00 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/19 | V Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 67-19 | |
| Fri., 1/19 | JV Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Squash | V G Squash v Rye Country Day School- 3 Cedar St, Rye NY | Away - Not Listed | 4:00 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | L 0-1 | |
| Sat., 1/20 | V Boys Indoor Track | Staples, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Trumbull, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/20 | V Boys Indoor Track | SCC Coaches Invitational- Hillhouse HS- New Haven | Away - Not Listed | 3:00 p.m. | ||
| Sat., 1/20 | V Wrestling | Granby Duals | Away - Granby Memorial HS-K.L. King Gymnasium | 9:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/20 | V Girls Gymnastics | New Canaan, Stamford, Westhill | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien 129.7 Westhill 55 Stamford 93.15 New Canaan 60.6 | |
| Sat., 1/20 | V Girls Indoor Track | Staples, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Trumbull, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | SCC Coaches Invitational- Hillhouse HS- New Haven | Away - Not Listed | 9:00 a.m. | ||
| Sun., 1/21 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 5:30 p.m. | ||
| Sun., 1/21 | JV Girls Squash | G JV Squash v Westport JV | Home - MSquash [Directions] | 4:30 p.m. | ||
| Mon., 1/22 | V Boys Squash | B V Squash v Rye Boys V | Home - MSquash [Directions] | 7:30 p.m. | ||
| Mon., 1/22 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | W 8-1 | |
| Tue., 1/23 | V Boys Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 61-45 | |
| Tue., 1/23 | JV Boys Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Boys Diving | Fairfield Ludlowe | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 1/23 | JV Boys Squash | B JV Squash v Westport JV boys | Home - MSquash [Directions] | 8:00 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 64-46 | |
| Tue., 1/23 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Girls Ice Hockey | Greenwich Academy | Home - Chelsea Piers - Connecticut-North Rink [Directions] | 3:15 p.m. | L 1-5 | |
| Wed., 1/24 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 4-1 | |
| Wed., 1/24 | V Boys Squash | B V Squash v Greenwich Boys A | Home - MSquash [Directions] | 7:30 p.m. | ||
| Wed., 1/24 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/24 | V Wrestling | Staples | Home - Darien HS-DHS South Gym [Directions] | 5:00 p.m. | ||
| Thu., 1/25 | V Boys Diving | Diving V Ridgefield | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 1/25 | JV Boys Squash | B JV Squash v Briarcliff JV @ Lifetime Rye- 1 Westchester Park Drive, West Harrison, NY | Away - Not Listed | 8:00 p.m. | ||
| Thu., 1/25 | FR Girls Basketball | Cardinal Kung Academy | Away - Cardinal Kung Academy-GYM | 3:45 p.m. | ||
| Thu., 1/25 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:30 p.m. | Darien 132.4 Greenwich 114.35 | |
| Fri., 1/26 | V Boys Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 64-91 | |
| Fri., 1/26 | JV Boys Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | JV Boys Ice Hockey | Ridgefield | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Ridgefield | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 55-33 | |
| Fri., 1/26 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/26 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/26 | JV Girls Squash | G JV Squash v Rye Girls Red @ Chelsea Piers | Away - Chelsea Piers - Field Side-Chelsea Piers Connecticut | 7:00 p.m. | ||
| Sat., 1/27 | FR Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/27 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | W 4-1 | |
| Sat., 1/27 | V Boys Indoor Track | FCIAC Divisional Championship @ Wilton | Away - Wilton HS-Wilton Field House | 9:30 a.m. | ||
| Sat., 1/27 | V Boys Squash | B V Squash v New Canaan | Home - MSquash [Directions] | 4:30 p.m. | ||
| Sat., 1/27 | V Wrestling | Brookfield Invitational | Away - Brookfield HS-BHS Small & Big Gym | 9:30 a.m. | ||
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, New Milford, St. Joseph, Stamford, Staples, Trumbull, Westhill, Weston, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Sat., 1/27 | FR Girls Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/27 | V Girls Indoor Track | FCIAC Divisional Championship @ Wilton | Away - Wilton HS-Wilton Field House | 9:30 a.m. | ||
| Mon., 1/29 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Sacred Heart University-Martire Arena [Directions] | 5:15 p.m. | T 3-3 | |
| Tue., 1/30 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | W 77-62 | |
| Tue., 1/30 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | JV Boys Squash | B JV Squash v Rye Boys Varsity B @ Chelsea Piers | Away - Chelsea Piers - Field Side-Chelsea Piers Connecticut | 7:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 48-44 | |
| Tue., 1/30 | JV Girls Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Girls Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/31 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:30 p.m. | ||
| Wed., 1/31 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/31 | V Girls Ice Hockey | Greenwich Academy | Away - Chelsea Piers - Connecticut-North Rink | 3:30 p.m. | T 3-3 | |
| Wed., 1/31 | V Girls Squash | G V Squash v Greenwich Girls V @ Chelsea Piers | Away - Chelsea Piers - Field Side-Chelsea Piers Connecticut | 7:00 p.m. | ||
| Thu., 2/1 | V Boys Indoor Track | FCIAC Championship | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Thu., 2/1 | V Boys Squash | B V Squash v City Squash Boys Inter. | Home - MSquash [Directions] | Postponed | ||
| Thu., 2/1 | V Girls Indoor Track | FCIAC Championship | Home - Floyd Little Athletic Center-Field House [Directions] | 5:00 p.m. | ||
| Fri., 2/2 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 49-47 | |
| Fri., 2/2 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 2/2 | JV Boys Squash | B JV Squash v Bronxville JV @ Westchester Squash Academy- 628 Fayette Ave, Mamaroneck, NY | Away - Not Listed | 8:00 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 41-21 | |
| Fri., 2/2 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | FR Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/3 | JV Boys Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/3 | FR Boys Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | Bishop Hendricken (RI) | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | L 4-3 (OT) | |
| Sat., 2/3 | V Boys Indoor Track | Last Chance Meet- Staples HS | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 2/3 | V Wrestling | Foran Duals | Away - Foran HS -Edna L. Fraser Gymnasium | 9:00 a.m. | ||
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Gymnastics | Wilton | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien: 127.6 Wilton: 130 | |
| Sat., 2/3 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 8:40 p.m. | W 9-0 | |
| Sat., 2/3 | V Girls Indoor Track | Last Chance Meet- Staples HS | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 2/3 | JV Girls Squash | G JV Squash v Rye Girls Gray | Home - MSquash [Directions] | 4:30 p.m. | ||
| Sun., 2/4 | V Boys Ice Hockey | LaSalle Academy (RI) | Home - Darien Ice House-Ice Rink [Directions] | 3:00 p.m. | L 2-0 | |
| Mon., 2/5 | JV Boys Ice Hockey | Brunswick School | Away - Brunswick School-Hartong Rink | 5:00 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 68-60 | |
| Tue., 2/6 | JV Boys Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | JV Boys Squash | B JV Squash v New Canaan Boys JV | Home - MSquash [Directions] | 8:00 p.m. | ||
| Tue., 2/6 | V Wrestling | Wilton | Home - Darien HS-DHS South Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 54-28 | |
| Tue., 2/6 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | W 4-1 | |
| Wed., 2/7 | V Boys Squash | V B Squash v City Squash MACS @ City Squash Fordham 2532 Bathgate Ave, Bronx, NY | Away - Not Listed | 6:00 p.m. | ||
| Wed., 2/7 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Darien 135.8 | |
| Wed., 2/7 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | 6:20 p.m. | W 3-1 | |
| Thu., 2/8 | JV Boys Squash | B JV Squash v Scarsdale Boys Mixed | Home - MSquash [Directions] | 8:00 p.m. | ||
| Thu., 2/8 | V Girls Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | V Girls Indoor Track | Class LL g indoor track championship @ Hillhouse HS | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/8 | JV Girls Squash | G JV Squash v City Squash Girls Inter @ City Squash Fordham 2532 Bathgate Ave, Bronx NY | Away - Not Listed | 6:00 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 64-58 | |
| Fri., 2/9 | JV Boys Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 2/9 | 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 | 4:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 57-36 | |
| Fri., 2/9 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | W 5-0 | |
| Sat., 2/10 | V Boys Indoor Track | Class L Meet @ Hillhouse HS | Away - Floyd Little Athletic Center-Field House | 10:00 a.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/10 | V Wrestling | FCIAC Wrestling Championships | Away - New Canaan HS-Main Gym | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Gymnastics | FCIAC Gymnastics Championships @ Gymnastics & Cheer Academy- Fairfield | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 2:00 p.m. | Trumbull: 141.9 FLHS:136.25 Staples: 132.25 Darien: 129.05 Wilton: 127.9 FWHS 122.7 GHS:108.25 | |
| Sat., 2/10 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | W 1-0 | |
| Sat., 2/10 | JV Girls Squash | G JV Squash v Choate JV girls | Home - MSquash [Directions] | 4:30 p.m. | ||
| Mon., 2/12 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 73-43 | |
| Mon., 2/12 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Boys Squash | B V Squash v City Squash BCSM @ City Squash Fordham 2532 Bathgate Ave, Bronx NY | Away - Not Listed | 6:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 63-35 | |
| Mon., 2/12 | JV Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | JV Girls Squash | G JV Squash v Rye Girls Black @ Chelsea Piers | Away - Chelsea Piers - Field Side-Chelsea Piers Connecticut | 7:00 p.m. | ||
| Tue., 2/13 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-TBA [Directions] | Postponed | ||
| Wed., 2/14 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | L 81-51 | |
| Wed., 2/14 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | L 4-3 (OT) | |
| Wed., 2/14 | V Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 57-41 | |
| Wed., 2/14 | JV Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Girls Squash | G V Squash v Bronxville Girls V | Home - MSquash [Directions] | 7:30 p.m. | ||
| Fri., 2/16 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | ||
| Fri., 2/16 | Miscellaneous Events | B Basketball Team to Fairfield U to watch game | Home - Not Listed [Directions] | 7:00 p.m. | ||
| Sat., 2/17 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | W 4-0 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Ice Hockey | East Catholic Coop | Home - Darien Ice House-Ice Rink [Directions] | 6:10 p.m. | W 3-0 | |
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 78-57 | |
| Mon., 2/19 | JV Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/19 | V Boys Ice Hockey | St. Joseph | Away - Sports Center of Connecticut-Lower [Directions] | 1:30 p.m. | W 4-0 | |
| Mon., 2/19 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 10:00 a.m. | ||
| Wed., 2/21 | V Boys Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 56-55 | |
| Wed., 2/21 | JV Boys Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | L 4-0 | |
| Wed., 2/21 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | 7:40 p.m. | ||
| Fri., 2/23 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | Canceled | Cancelled | |
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Ice Hockey | Westhill/Stamford | Home - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Sat., 2/24 | V Boys Squash | Squash Nationals @ Arlen Specter Center, Philadelphia PA 2/23-25 | Away - Not Listed | TBA | ||
| Sat., 2/24 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Jonathan Law | 1:00 p.m. | ||
| Sat., 2/24 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 3:00 p.m. | ||
| Sat., 2/24 | V Girls Squash | Squash Nationals @ Arlen Specter Center Philadelphia PA 2/23-25 | Away - Not Listed | TBA | ||
| Mon., 2/26 | JV Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 4:00 p.m. | ||
| Tue., 2/27 | V Boys Swimming and Diving | Greenwich, TBA | Away - Greenwich HS-Pool [Directions] | 5:15 p.m. | ||
| Wed., 2/28 | V Boys Diving | B Diving FCIAC Finals @ Westhill HS | Away - Not Listed | 5:00 p.m. | ||
| Wed., 2/28 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 7:10 p.m. | ||
| Thu., 2/29 | V Boys Swimming and Diving | FCIAC Swim Finals @ Greenwich HS | Away - Greenwich HS | 6:00 p.m. | ||
| Thu., 2/29 | V Girls Ice Hockey | Hamden Coop | Home - Darien Ice House-Ice Rink [Directions] | 5:30 p.m. | ||
| Thu., 2/29 | Unified Sports Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 3:00 p.m. | ||
| Fri., 3/1 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Sat., 3/2 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 12:00 p.m. | ||
| Sat., 3/2 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:30 p.m. | ||
| Sun., 3/3 | JV Boys Ice Hockey | TBA | Home - Stamford Twin Rinks-West [Directions] | 12:30 p.m. | ||
| Wed., 3/6 | V Boys Ice Hockey | CIAC Div I First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class L Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Wed., 3/6 | Miscellaneous Events | DHS Pickleball Tournament- Main Gym or Tennis Courts | Home - Darien HS-DHS Main Gym [Directions] | 3:00 p.m. | ||
| Thu., 3/7 | Miscellaneous Events | Unified Sports Event @ Fairfield Ludlowe HS | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 3/8 | Miscellaneous Events | DHS School Dance | Home - Darien HS-DHS Main Gym [Directions] | 2:30 p.m. | ||
| Sat., 3/9 | V Boys Ice Hockey | Ridgefield | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:00 p.m. | W 3-1 | |
| Sat., 3/9 | V Boys Ice Hockey | CIAC Div I Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 11:15 a.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Wed., 3/13 | V Boys Ice Hockey | New Canaan | Away - Quinnipiac University-TD Bank Sports Center [Directions] | 5:30 p.m. | L 1-6 | |
| Wed., 3/13 | V Boys Ice Hockey | CIAC Div I Semifinal | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Thu., 3/14 | Unified Sports Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Tue., 3/19 | V Boys Ice Hockey | CIAC Div I Final | Away - Site TBA | TBA | ||
| Tue., 3/19 | V Boys Lacrosse | Blue v White Scrimmage | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 3:30 p.m. | ||
| Thu., 3/21 | V Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:45 p.m. | ||
| Thu., 3/21 | JV Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 3:45 p.m. | ||
| Thu., 3/21 | V Boys Lacrosse | Iona Prep (NY) (Scrim.) | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | ||
| Thu., 3/21 | JV Boys Lacrosse | Iona Prep (NY) (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 3/21 | V Boys Rugby | Trumbull (Scrim.) | Home - Royle School Field [Directions] | 4:30 p.m. | ||
| Thu., 3/21 | V Softball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 3/22 | V Baseball | Greenwich (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:15 p.m. | ||
| Fri., 3/22 | JV Baseball | Greenwich (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:15 p.m. | ||
| Fri., 3/22 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Jamboree on stadium field, center and upper ovals. | Home - Darien HS-[CIAC] Willow Brook Park [Directions] | 8:00 a.m. | ||
| Sat., 3/23 | JV Boys Lacrosse | Salisbury School, Staples (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 8:00 a.m. | ||
| Sat., 3/23 | V Boys Volleyball | Masuk, TBA, Wolcott Tech, Regis (NY), Ridgefield, Shelton, South Windsor | Home - Darien HS-DHS Main Gym [Directions] | 8:30 a.m. | ||
| Sun., 3/24 | V Girls Lacrosse | scrimmage v Stoneridge MD @ Greenwich Academy | Away - Not Listed | 9:00 a.m. | ||
| Sun., 3/24 | JV Girls Lacrosse | scrimmage v Stoneridge MD @ Greenwich Academy | Away - Not Listed | 9:00 a.m. | ||
| Mon., 3/25 | FR Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Softball | Stamford (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Baseball | Wilton (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:15 p.m. | ||
| Tue., 3/26 | JV Baseball | Wilton (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:15 p.m. | ||
| Tue., 3/26 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 3/26 | V Softball | Greenwich (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Baseball | Bethel (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | JV Baseball | Bethel (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Lacrosse | Cheshire (Scrim.) | Away - Cheshire HS-Main Game Field [Directions] | 6:30 p.m. | ||
| Wed., 3/27 | JV Boys Lacrosse | Cheshire (Scrim.) | Away - Cheshire HS-Grass Fields [Directions] | Canceled | Cancelled | |
| Wed., 3/27 | V Boys Volleyball | Iona Prep (NY) (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | JV Boys Volleyball | Iona Prep (NY) (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 3/27 | V Co-ed Sailing | Greenwich, Fairfield Ludlowe | Away - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Softball | Bethel (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 3/30 | V Baseball | North Haven | Away - North Haven MS-Bailey Road Baseball Field [Directions] | 12:00 p.m. | L 6-5 | |
| Sat., 3/30 | JV Baseball | North Haven | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 3/30 | V Boys Lacrosse | Fairfield Prep | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | ||
| Sat., 3/30 | JV Boys Lacrosse | Fairfield Prep | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 3/30 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 10:00 a.m. | ||
| Sat., 3/30 | V Boys Volleyball | CIAC Boys' Volleyball Invitational | Away - CT Volleyball Center Woodbridge | 8:00 a.m. | ||
| Mon., 4/1 | FR Baseball | Stamford | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Boys Volleyball | Simsbury | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Mon., 4/1 | JV Boys Volleyball | Simsbury | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Mon., 4/1 | V Girls Golf | Staples | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Mon., 4/1 | V Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 4:30 p.m. | W 5-0 | |
| Mon., 4/1 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | FR Boys Lacrosse | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | Postponed | ||
| Wed., 4/3 | JV Baseball | Stratford | Away - Wooster MS Field [Directions] | Postponed | ||
| Wed., 4/3 | FR Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 5:00 p.m. | ||
| Thu., 4/4 | V Baseball | Wilbur Cross | Away - Rice Field-Rice Field 1 [Directions] | Canceled | Cancelled | |
| Thu., 4/4 | V Baseball | Wilbur Cross | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 11-1 | |
| Thu., 4/4 | V Boys Lacrosse | Brunswick School | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | ||
| Thu., 4/4 | JV Boys Lacrosse | Brunswick School | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | FR Boys Lacrosse | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Boys Volleyball | Farmington | Away - Farmington HS [Directions] | 6:15 p.m. | W 3-2 | |
| Thu., 4/4 | JV Boys Volleyball | Farmington | Away - Farmington HS [Directions] | 5:00 p.m. | ||
| Thu., 4/4 | V Co-ed Sailing | Greenwich | Away - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 4/4 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | Postponed | ||
| Thu., 4/4 | V Girls Rugby | Ridgefield, Simsbury | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | ||
| Fri., 4/5 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | W 12-1 | |
| Fri., 4/5 | FR Baseball | Bethel | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Boys Tennis | Avon | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Fri., 4/5 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Softball | Lauralton Hall | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 4/6 | V Baseball | New Fairfield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | W 2-1 | |
| Sat., 4/6 | JV Baseball | New Fairfield | Home - Darien HS-DHS Baseball - JV Field [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | V Softball | Immaculate | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 12:00 p.m. | W 11-0 | |
| Sun., 4/7 | V Boys Lacrosse | Manhassett (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Sun., 4/7 | JV Boys Lacrosse | Manhassett (NY) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 1:00 p.m. | ||
| Sun., 4/7 | V Girls Lacrosse | St. Paul School for Girls (MD) | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | W 9-7 | |
| Mon., 4/8 | FR Baseball | New Canaan | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | JV Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 5:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/8 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | FR Girls Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Softball | Wilton | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Norwalk | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/9 | V Baseball | Stratford | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:15 p.m. | ||
| Tue., 4/9 | JV Baseball | Stratford | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:15 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | V Boys Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Westhill | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 4-3 [Detailed Results] | |
| Tue., 4/9 | V Boys Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 4/9 | JV Boys Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | V Girls Golf | Wilton | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | W 19-4 | |
| Tue., 4/9 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Outdoor Track | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/10 | FR Baseball | Greenwich | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Wed., 4/10 | V Co-ed Sailing | FCSL Meet @ Grassy Island or Indian Harbor- Greenwich | Away - Not Listed | 3:00 p.m. | ||
| Wed., 4/10 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 4/10 | JV Girls Golf | New Canaan | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Wed., 4/10 | FR Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-2nd Field | 3:30 p.m. | ||
| Wed., 4/10 | FR Girls Lacrosse | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 4/10 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 4/11 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | JV Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 20-2 | |
| Thu., 4/11 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Thu., 4/11 | V Girls Rugby | Ridgefield | Home - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Baseball | Norwalk | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | JV Baseball | Norwalk | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 4/12 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 4/12 | V Softball | Norwalk | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Sat., 4/13 | JV Boys Lacrosse | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Sat., 4/13 | FR Boys Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/13 | V Girls Lacrosse | McDonogh (MD) | Away - Not Listed | 1:30 p.m. | L 5-4 | |
| Mon., 4/15 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 12:00 p.m. | ||
| Mon., 4/15 | JV Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 12:00 p.m. | ||
| Mon., 4/15 | FR Baseball | Westhill | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 11:00 a.m. | ||
| Mon., 4/15 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 12:00 p.m. | ||
| Mon., 4/15 | V Boys Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | JV Boys Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/15 | V Girls Lacrosse | Garden City (NY) | Away - Garden City HS | 5:00 p.m. | W 10-9 | |
| Mon., 4/15 | JV Girls Lacrosse | Garden City (NY) | Away - Garden City HS | 4:00 p.m. | ||
| Mon., 4/15 | V Softball | Westhill | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Stamford | Home - Darien HS-DHS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 [Detailed Results] | |
| Tue., 4/16 | V Boys Lacrosse | Yorktown (NY) | Away - Yorktown Heights HS-Lacrosse Field | 7:00 p.m. | ||
| Tue., 4/16 | JV Boys Lacrosse | Yorktown (NY) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:00 p.m. | ||
| Tue., 4/16 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | Postponed | ||
| Tue., 4/16 | V Girls Tennis | St. Joseph | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/16 | JV Girls Tennis | St. Joseph | Home - Weed Beach Tennis Courts [Directions] | Postponed | ||
| Wed., 4/17 | V Baseball | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | JV Baseball | Wilton | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | FR Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/17 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Boys Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | JV Boys Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/17 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 5:00 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Thu., 4/18 | JV Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Center Oval - Turf [Directions] | 2:00 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | L 4-5 | |
| Thu., 4/18 | JV Girls Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 4/19 | V Baseball | Stamford | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | JV Baseball | Stamford | Home - Darien HS-DHS Baseball - JV Field [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | FR Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/19 | V Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 1:00 p.m. | ||
| Fri., 4/19 | JV Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 2:45 p.m. | ||
| Sat., 4/20 | V Boys Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | ||
| Sat., 4/20 | JV Boys Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 10:30 a.m. | ||
| Sat., 4/20 | V Co-ed Sailing | CT State Championship@ Indian Harbor, Greenwich | Away - Indian Harbor Yacht Club | 9:30 a.m. | ||
| Sat., 4/20 | V Girls Outdoor Track | Mongovan Invitational @ Bethel HS | Away - Not Listed | 9:00 a.m. | ||
| Mon., 4/22 | V Baseball | St. Joseph | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | JV Baseball | St. Joseph | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Boys Tennis | Trumbull | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | JV Boys Tennis | Trumbull | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Girls Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/23 | V Boys Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Boys Tennis | Fairfield Warde | Home - Cherry Lawn Park- Darien [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Boys Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Girls Golf | Wilton | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Tue., 4/23 | JV Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 18-5 | |
| Tue., 4/23 | JV Girls Lacrosse | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Bridgeport Central | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/23 | JV Girls Tennis | Fairfield Warde | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 5:00 p.m. | ||
| Wed., 4/24 | JV Boys Lacrosse | Chaminade (NY) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:00 p.m. | ||
| Wed., 4/24 | V Co-ed Sailing | FCSL Meet- Grassy Island or Indian Harbor- Greenwich | Away - Not Listed | 3:00 p.m. | ||
| Wed., 4/24 | V Girls Golf | Fairfield Ludlowe | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Wed., 4/24 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | Postponed | ||
| Wed., 4/24 | V Softball | Staples | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 5:00 p.m. | W 4-2 [Detailed Results] | |
| Wed., 4/24 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | JV Boys Tennis | New Canaan | Home - Cherry Lawn Park- Darien [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | JV Boys Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | T 5-5 | |
| Thu., 4/25 | JV Girls Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Girls Rugby | Staples, Simsbury | Away - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/25 | V Girls Tennis | New Canaan | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Thu., 4/25 | JV Girls Tennis | New Canaan | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Baseball | Trumbull | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away - Danbury HS-Danbury HS Stadium | 5:00 p.m. | ||
| Fri., 4/26 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/26 | V Co-ed Sailing | FCSL Fleet Race Championship- Grassy Island or Indian Harbor- Greenwich | Away - Not Listed | Canceled | Cancelled | |
| Fri., 4/26 | FR Girls Lacrosse | Norwalk | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Softball | Trumbull | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | ||
| Fri., 4/26 | JV Girls Tennis | Wilton | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/27 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Sat., 4/27 | FR Boys Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 4/27 | FR Boys Lacrosse | Chaminade (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 3:30 p.m. | ||
| Sat., 4/27 | V Co-ed Sailing | Shewolf Women's Regatta @ Tabor Academy, Marlon Mass. | Away - Not Listed | Canceled | Cancelled | |
| Sat., 4/27 | V Girls Lacrosse | Manhassett (NY) | Away - Cold Spring Harbor HS | 6:00 p.m. | W 13-2 | |
| Sat., 4/27 | JV Girls Lacrosse | Manhassett (NY) | Away - Manhasset Junior/Senior HS | 12:00 p.m. | ||
| Sun., 4/28 | V Co-ed Sailing | O'Day Qualifier @ Avery Point, Groton, CT 1084 Shennecossett Rd, Groton | Away - Not Listed | 9:30 a.m. | ||
| Mon., 4/29 | V Baseball | Bridgeport Central | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | V Boys Outdoor Track | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Co-ed Sailing | Greenwich Academy | Away - Greenwich Academy | 3:45 p.m. | ||
| Mon., 4/29 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 4/29 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 4/29 | JV Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Girls Lacrosse | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | L 0-6 [Detailed Results] | |
| Mon., 4/29 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:15 p.m. | ||
| Tue., 4/30 | JV Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Fairfield Warde | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Tennis | Fairfield Warde | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 6:00 p.m. | ||
| Tue., 4/30 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Co-ed Sailing | Silver Cup @ Grassy Island or Indian Harbor Point- Greenwich | Away - Not Listed | 3:00 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/30 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Baseball | New Canaan | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | Fairfield Prep | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Co-ed Sailing | Gold Cup @ Grassy Island or Indian Harbor Point- Greenwich | Away - Not Listed | 3:00 p.m. | ||
| Wed., 5/1 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | JV Girls Golf | New Canaan | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | V Girls Lacrosse | IMGAcademyFL | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Girls Lacrosse | Greenwich Academy | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 5/1 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Thu., 5/2 | FR Baseball | Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | V Boys Rugby | B Rugby v COBRA @ Sacred Heart U | Away - Not Listed | 5:30 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | JV Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:45 p.m. | ||
| Thu., 5/2 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | FR Girls Lacrosse | Greenwich Academy | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | V Girls Rugby | Ridgefield, North Haven | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Danbury | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 5/3 | V Baseball | Greenwich | Away - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Don Bosco (NJ) | Away - Don Bosco Prep School-Stadium Turf | 5:00 p.m. | ||
| Fri., 5/3 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | FR Girls Lacrosse | Sacred Heart of Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Postponed | ||
| Fri., 5/3 | V Softball | Greenwich | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | JV Girls Tennis | St. Joseph | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/4 | V Boys Lacrosse | Mamaroneck (NY) | Away - Mamaroneck HS-Field | 3:00 p.m. | ||
| Sat., 5/4 | JV Boys Lacrosse | Mamaroneck (NY) | Away - Mamaroneck HS-Field | 5:00 p.m. | ||
| Sat., 5/4 | FR Boys Lacrosse | Connor Corish Tournament @ Don Bosco HS NJ | Away - Not Listed | 1:00 p.m. | ||
| Sat., 5/4 | V Boys Outdoor Track | Fast Times @ Ridgefield HS | Away - Ridgefield HS-Tiger Hollow Stadium Track | 6:00 p.m. | ||
| Sat., 5/4 | V Girls Lacrosse | Summit (NJ) | Away - Summit HS-Upper HS Turf | 1:00 p.m. | ||
| Sat., 5/4 | JV Girls Lacrosse | Summit (NJ) | Away - Summit HS-Upper HS Turf | 3:00 p.m. | ||
| Sun., 5/5 | JV Boys Lacrosse | Lincoln-Sudbury (MA) (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | Cancelled | |
| Mon., 5/6 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Baseball | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | FR Baseball | Fairfield Warde | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 5/6 | V Boys Outdoor Track | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Fairfield Warde | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Fairfield Ludlowe | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Mon., 5/6 | JV Girls Tennis | Fairfield Ludlowe | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | Stamford | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Rugby | Ridgefield | Home - Royle School Field [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Boys Tennis | Ridgefield | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 5/7 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Baseball | Danbury | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Baseball | Danbury | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | Postponed | ||
| Wed., 5/8 | JV Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 5:00 p.m. | ||
| Wed., 5/8 | FR Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 5:00 p.m. | ||
| Wed., 5/8 | V Boys Tennis | Greenwich | Home - Darien HS-DHS Tennis Courts [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | JV Boys Tennis | Greenwich | Home - Weed Beach Tennis Courts [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Co-ed Sailing | FCSL Womens Championship- Grassy Island or Indian Harbor Point Greenwich | Away - Not Listed | Canceled | Cancelled | |
| Wed., 5/8 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | JV Girls Golf | Greenwich | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | V Girls Lacrosse | Sacred Heart of Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 6:00 p.m. | ||
| Wed., 5/8 | JV Girls Lacrosse | Sacred Heart of Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | Cancelled | |
| Wed., 5/8 | FR Girls Lacrosse | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:30 p.m. | W 6-1 [Detailed Results] | |
| Thu., 5/9 | FR Boys Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Brien McMahon | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Girls Golf | New Canaan | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | ||
| Thu., 5/9 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Girls Outdoor Track | Loucks Games @ White Plains HS | Away - Not Listed | 6:00 p.m. | ||
| Fri., 5/10 | V Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | JV Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Boys Lacrosse | Fairfield Prep | Home - Don Bosco Preparatory HS [Directions] | 7:00 p.m. | ||
| Fri., 5/10 | FR Boys Lacrosse | Connor Corish Tournament @ Don Bosco HS NJ | Away - Not Listed | 7:00 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Co-ed Sailing | Herreschoff (New England Women's Championship) Qualifier- Portland, Maine | Away - Not Listed | TBA | ||
| Fri., 5/10 | FR Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | ||
| Sat., 5/11 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Sat., 5/11 | FR Boys Lacrosse | Connor Corish Tournament @ Don Bosco HS | Away - Not Listed | 3:00 p.m. | ||
| Sat., 5/11 | V Co-ed Sailing | Herreschoff (New England Women's Championship) Qualifier- Portland, Maine | Away - Not Listed | 9:15 a.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | Loucks Games @ White Plains HS | Away - Not Listed | 1:00 p.m. | ||
| Sat., 5/11 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Sun., 5/12 | V Co-ed Sailing | O'Day Championship- Greenwich, CT Indian Harbor or Grass Island | Away - Not Listed | 9:30 a.m. | ||
| Mon., 5/13 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | Ridgefield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Boys Tennis | Staples | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | FR Girls Lacrosse | Ridgefield | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Softball | Ridgefield | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | ||
| Tue., 5/14 | JV Baseball | Brien McMahon | Away - Roton MS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | Seton Hall Prep (NJ) (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 6:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | Chatham (NJ) | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | Cancelled | |
| Tue., 5/14 | JV Boys Lacrosse | intra-squad JV v Frosh | Home - Darien HS-DHS Center Oval - Turf [Directions] | 3:30 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | Chatham (NJ) | Home - Darien HS-DHS Center Oval - Turf [Directions] | Canceled | Cancelled | |
| Tue., 5/14 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/14 | FR Girls Lacrosse | Sacred Heart of Greenwich | Home - Darien HS-DHS Center Oval - Turf [Directions] | Canceled | Cancelled | |
| Tue., 5/14 | V Girls Rugby | Greenwich | Home - MMS Upper Field-MMS Upper [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | V Softball | Brien McMahon | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | JV Girls Tennis | Greenwich | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Baseball | Brien McMahon | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | Canceled | Cancelled | |
| Wed., 5/15 | FR Baseball | Norwalk | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | Canceled | Cancelled | |
| Wed., 5/15 | JV Boys Rugby | Staples | Home - MMS Upper Field-MMS Upper [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | JV Boys Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/15 | V Co-ed Sailing | FCSL Match Race Championship- Noroton Yacht Club | Home - Noroton Yacht Club [Directions] | 3:00 p.m. | ||
| Wed., 5/15 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/15 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:00 p.m. | ||
| Wed., 5/15 | FR Girls Lacrosse | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCRC [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | FR Boys Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 5/16 | V Boys Volleyball | Shelton | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | JV Boys Volleyball | Shelton | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/16 | V Girls Lacrosse | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | V Girls Rugby | Fairfield Ludlowe | Home - MMS Upper Field-MMS Upper [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:30 p.m. | ||
| Fri., 5/17 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 1:30 p.m. | ||
| Fri., 5/17 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | Miscellaneous Events | Junior Prom | Home - TBA [Directions] | TBA | ||
| Sat., 5/18 | V Boys Lacrosse | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Sat., 5/18 | V Boys Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 5/18 | JV Boys Volleyball | B Volleyball end of season tournament @ Ludlowe HS | Away - Fairfield Ludlowe HS-Main Gym | Canceled | Cancelled | |
| Sat., 5/18 | V Co-ed Sailing | TERK Team Racing Tournament- Hyannis, MA | Away - Not Listed | Canceled | Cancelled | |
| Sun., 5/19 | V Co-ed Sailing | TERK Team Racing Tournament- Hyannis, MA | Away - Not Listed | Canceled | Cancelled | |
| Mon., 5/20 | FR Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Boys Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 5/20 | V Girls Lacrosse | Wilton | Away - Brien McMahon HS [Directions] | 7:00 p.m. | ||
| Tue., 5/21 | V Boys Lacrosse | Ridgefield | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | ||
| Tue., 5/21 | FR Boys Lacrosse | Guilford | Away - Guilford HS-Maturo Field [Directions] | 4:30 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Tue., 5/21 | V Girls Golf | Danbury | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 2:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Tue., 5/21 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Boys Volleyball | Ridgefield | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 5/22 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 5/22 | JV Girls Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Wed., 5/22 | V Girls Lacrosse | New Canaan | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | ||
| Wed., 5/22 | V Softball | New Canaan (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/23 | V Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:45 p.m. | ||
| Thu., 5/23 | V Boys Lacrosse | Staples | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/23 | V Girls Golf | Holohan @ CC of NC | Away - CCNC | 1:00 p.m. | ||
| Fri., 5/24 | V Boys Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/25 | V Co-ed Sailing | Herreschoff Finals- New Bedford, Mass- 1641 Padanaram Ave New Bedford, MA. Community Boating Center | Away - Not Listed | 4:00 p.m. | ||
| Sat., 5/25 | V Softball | Masuk (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 5/25 | V Girls Tennis | Brien McMahon | Home - Darien HS-DHS Tennis Courts [Directions] | 12:00 p.m. | ||
| Tue., 5/28 | V Baseball | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:30 p.m. | ||
| Tue., 5/28 | V Boys Tennis | Glastonbury | Away - Glastonbury HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | V Softball | Simsbury | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Girls Tennis | Fairfield Ludlowe | Home - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | V Boys Lacrosse | Hamden | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Wed., 5/29 | V Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 4:00 p.m. | ||
| Wed., 5/29 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 5/29 | V Boys Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/29 | V Softball | Enfield | Away - Enfield HS-EHS SOFTBALL V [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Girls Golf | G Golf FCIAC Championship | Away - Not Listed | TBA | ||
| Fri., 5/31 | V Girls Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | ||
| Fri., 5/31 | Miscellaneous Events | Senior Prom | Home - TBA [Directions] | TBA | ||
| Sat., 6/1 | V Boys Lacrosse | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | ||
| Sat., 6/1 | V Boys Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 6/1 | V Co-ed Sailing | Phoebe King Memorial Regatta- Annapolis MD | Away - Not Listed | TBA | ||
| Sat., 6/1 | V Co-ed Sailing | Mallory Trophy- UF Fleet Racing Championship @ College of Charleston | Away - Not Listed | Canceled | Cancelled | |
| Sat., 6/1 | V Softball | Southington | Away - Southington HS-1 Softball Varsity Field [Directions] | 3:30 p.m. | ||
| Sun., 6/2 | V Co-ed Sailing | Phoebe King Memorial Regatta- Annapolis MD | Away - Not Listed | TBA | ||
| Sun., 6/2 | V Co-ed Sailing | Mallory Trophy- UF Fleet Racing Championship @ College of Charleston | Away - Not Listed | Canceled | Cancelled | |
| Mon., 6/3 | V Boys Outdoor Track | State Open- Willow Brook Park- New Britain | Away - Not Listed | 1:30 p.m. | ||
| Mon., 6/3 | V Girls Golf | G Golf State Finals- Tashau Knolls-Trumbull | Away - Tashua Knolls Golf Course | 8:30 a.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | State Open- Willow Brook Park- New Britain | Away - Not Listed | 1:30 p.m. | ||
| Tue., 6/4 | V Boys Volleyball | East Hartford | Home - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 6/4 | V Girls Lacrosse | Greenwich | Home - Fairfield University-Rafferty Stadium [Directions] | 4:30 p.m. | ||
| Wed., 6/5 | V Boys Lacrosse | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 6/6 | V Boys Volleyball | Ridgefield | Home - Newtown HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 6/8 | V Girls Lacrosse | New Canaan | Home - Sacred Heart University-Turf Field [Directions] | 2:00 p.m. | ||
| Sun., 6/9 | V Boys Lacrosse | Fairfield Prep | Away - Sacred Heart University [Directions] | 5:30 p.m. | ||
| Mon., 6/10 | V Boys Outdoor Track | Decathalon- Willowbrook Park- New Britian | Away - Not Listed | 10:00 a.m. | ||
| Mon., 6/10 | V Girls Outdoor Track | Decathalon- Willowbrook Park- New Britian | Away - Not Listed | 10:00 a.m. | ||
| Tue., 6/11 | V Boys Outdoor Track | Decathalon- Willowbrook Park- New Britian | Away - Not Listed | 10:00 a.m. | ||
| Tue., 6/11 | V Girls Outdoor Track | Decathalon- Willowbrook Park- New Britian | Away - Not Listed | 10:00 a.m. | ||