| Darien 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1088 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/25 | V Football | Cheshire (Scrim.) | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 8/27, Time to 6:00 p.m. | ||||||
| Sun., 8/29 | V Field Hockey | Darien HS Play Day | Home - Darien HS-DHS Stadium Field [Directions] | 9:00 a.m. | ||
| Mon., 8/30 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 8/31 | V Girls Soccer | Hamden (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 9/1 | JV Boys Soccer | St. Lukes (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 9/1 | V Field Hockey | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | Cancelled | |
| Wed., 9/1 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | Cancelled | |
| Wed., 9/1 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/2 | JV Boys Golf | Fairfield Warde | Home - Country Club of Darien [Directions] | Canceled | Cancelled | |
| Thu., 9/2 | JV Boys Golf | Ridgefield, Fairfield Ludlowe | Away - Ridgefield Golf Course [Directions] | Canceled | Cancelled | |
| Thu., 9/2 | V Field Hockey | Norwalk (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Thu., 9/2 | V Girls Soccer | Southington (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 9/2 | JV Girls Soccer | Southington (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 9/3 | V Football | Fairfield Prep (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Boys Soccer | King and Low-Heywood Thomas (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 9/4 | FR Football | Fairfield Prep (Scrim.) | Away - Fairfield University-Barlow Field [Directions] | 10:00 a.m. | ||
| Sat., 9/4 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 9/4 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - CSH Grass Lacrosse Field | 9:00 a.m. | ||
| Sat., 9/4 | V Girls Volleyball | East Lyme (Scrim.) | Home - Darien HS-DHS Main Gym [Directions] | 8:30 a.m. | ||
| Sat., 9/4 | V Girls Volleyball | TBA | Home - Darien HS-DHS Main Gym [Directions] | 8:30 a.m. | ||
| Wed., 9/8 | V Boys Golf | Wilton | Home - Country Club of Darien [Directions] | 3:15 p.m. | Wilton 165 Darien 177 | |
| Wed., 9/8 | JV Boys Golf | Wilton | Home - Country Club of Darien [Directions] | 3:15 p.m. | ||
| Wed., 9/8 | V Boys Soccer | Weston (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 9/8 | JV Boys Soccer | Weston (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/9 | JV Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Postponed | ||
| Thu., 9/9 | V Girls Soccer | Norwalk | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 8-1 | |
| Thu., 9/9 | JV Girls Soccer | Norwalk | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/9 | V Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/9 | JV Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/9 | FR Girls Volleyball | Brookfield | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/10 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | T 1-1 | |
| Fri., 9/10 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Fri., 9/10 | V Field Hockey | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 9/10 | JV Field Hockey | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 9/10 | FR Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 9/10 | V Girls Volleyball | Woodstock Academy | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/10 | JV Girls Volleyball | Woodstock Academy | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/10 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/11 | V Football | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | W 41-8 | |
| Sat., 9/11 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 12:00 p.m. | ||
| Sat., 9/11 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | V Girls Volleyball | CIAC Early Season Tournament | Away - Connecticut Sports Center | 8:00 a.m. | ||
| Mon., 9/13 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:00 p.m. | ||
| Mon., 9/13 | V Boys Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 157 Trumbull 205 | |
| Mon., 9/13 | JV Boys Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Mon., 9/13 | V Field Hockey | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 9-0 | |
| Mon., 9/13 | JV Field Hockey | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 9/13 | FR Field Hockey | Greenwich Country Day | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 9/13 | V Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:30 p.m. | W 4-0 | |
| Mon., 9/13 | JV Girls Soccer | Westhill | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:30 p.m. | ||
| Mon., 9/13 | FR Girls Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/13 | V Girls Volleyball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Mon., 9/13 | JV Girls Volleyball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 6:30 p.m. | ||
| Mon., 9/13 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Staples, Danbury, Norwalk | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:15 p.m. | Darien 158 Ridgefield 159 | |
| Tue., 9/14 | V Boys Soccer | Westhill | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/14 | JV Boys Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Staples, Danbury, Norwalk | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | FR Field Hockey | Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Girls Swimming and Diving | Fairfield Warde | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 9/15 | FR Football | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | Canceled | Cancelled | |
| Wed., 9/15 | FR Football | Ridgefield | Home - Darien HS-DHS Stadium East [Directions] | 4:30 p.m. | ||
| Wed., 9/15 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Darien 154 Westhill 167 | |
| Wed., 9/15 | FR Boys Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/17 | V Football | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 7:00 p.m. | W 47-0 | |
| Fri., 9/17 | FR Boys Soccer | Westhill | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:30 p.m. | ||
| Fri., 9/17 | V Field Hockey | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 4-1 | |
| Fri., 9/17 | JV Field Hockey | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Fri., 9/17 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | T 2-2 | |
| Fri., 9/17 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 9/17 | FR Girls Soccer | Greenwich Country Day | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 9/18 | V Boys Cross Country | 32nd Wilton XC Invitational @ Allens Meadows | Away - Allen's Meadow | 9:00 a.m. | ||
| Sat., 9/18 | JV Football | Bridgeport Central | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | V Boys Soccer | Trumbull | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 1:00 p.m. | W 5-0 | |
| Sat., 9/18 | JV Boys Soccer | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 9/18 | V Girls Cross Country | 32nd Wilton XC Invitational @ Allens Meadows | Away - Allen's Meadow | 9:00 a.m. | ||
| Sat., 9/18 | FR Field Hockey | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FR Girls Soccer | Masuk | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FR Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | ||
| Mon., 9/20 | V Boys Golf | Fairfield Warde | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 160 Staples Warde 180 | |
| Mon., 9/20 | V Boys Golf | Staples | Home - Wee Burn CC [Directions] | 3:15 p.m. | see tri-match above | |
| Mon., 9/20 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 9/20 | FR Boys Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 9/21 | V Boys Cross Country | Ridgefield, Brien McMahon, St. Joseph | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Tue., 9/21 | V Girls Cross Country | Ridgefield, Brien McMahon, St. Joseph | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Girls Diving | Staples | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/21 | V Girls Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 1-4 | |
| Tue., 9/21 | JV Girls Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Darien 159 St. Joseph 147 | |
| Wed., 9/22 | JV Boys Golf | New Canaan | Away - New Canaan HS-CCNC [Directions] | 3:15 p.m. | ||
| Wed., 9/22 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 3-1 | |
| Wed., 9/22 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | V Field Hockey | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 9/22 | JV Field Hockey | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 9/22 | FR Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | FR Girls Soccer | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:15 p.m. | ||
| Thu., 9/23 | FR Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | Darien 164 McMahon 188 | |
| Thu., 9/23 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 9/23 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | W 2-0 | |
| Thu., 9/23 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | V Girls Swimming and Diving | Staples | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 9/24 | V Football | Newtown | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 27-14 | |
| Fri., 9/24 | V Boys Soccer | Brien McMahon | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 3:30 p.m. | W 3-1 | |
| Fri., 9/24 | JV Boys Soccer | Brien McMahon | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 3:30 p.m. | ||
| Fri., 9/24 | FR Boys Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:30 p.m. | ||
| Fri., 9/24 | V Field Hockey | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | W 6-0 | |
| Fri., 9/24 | V Field Hockey | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | JV Field Hockey | Brien McMahon | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 6:00 p.m. | ||
| Fri., 9/24 | FR Girls Soccer | Weston | Home - Darien HS-MMS (Middlesex) Lower Field at 30 Edgerton Street [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | JV Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 9/24 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away - King School-Upper School Gym | Canceled | Cancelled | |
| Sat., 9/25 | JV Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 9:00 a.m. | ||
| Sat., 9/25 | V Girls Cross Country | Ocean State XC Invitational | Away - Goddard Park | 8:45 a.m. | ||
| Sat., 9/25 | V Girls Diving | Wilton | Away - New Canaan YMCA-Pool [Directions] | 9:00 a.m. | ||
| Sat., 9/25 | FR Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | V Girls Volleyball | John Jay (NY) | Away - John Jay HS (Crossriver) | 9:00 a.m. | ||
| Sat., 9/25 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | ||
| Mon., 9/27 | V Boys Golf | Stamford | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 159 Stamford 200 | |
| Mon., 9/27 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 10-0 | |
| Mon., 9/27 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Mon., 9/27 | V Girls Soccer | Bridgeport Central | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 5:00 p.m. | W 8-0 | |
| Mon., 9/27 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Tue., 9/28 | V Boys Cross Country | Westhill, Wilton | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | JV Boys Golf | Greenwich | Away - TBA [Directions] | 3:30 p.m. | ||
| Tue., 9/28 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 4-2 | |
| Tue., 9/28 | JV Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Seaside Park [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Girls Cross Country | Westhill, Wilton | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/28 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 9/29 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | Darien 159 Ludlowe 170 | |
| Wed., 9/29 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 9/29 | FR Boys Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | FR Field Hockey | Westhill | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 9/30 | V Boys Golf | Norwalk | Home - Woodway Country Club [Directions] | 3:15 p.m. | Darien 153 Norwalk 199 | |
| Thu., 9/30 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | W 8-0 | |
| Thu., 9/30 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:30 p.m. | ||
| Thu., 9/30 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 1-2 | |
| Thu., 9/30 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | V Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/30 | JV Girls Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/30 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/1 | V Football | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 6:30 p.m. | W 49-7 | |
| Fri., 10/1 | V Boys Soccer | Staples | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 10/1 | JV Boys Soccer | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/1 | JV Field Hockey | Greenwich Country Day | Away - Greenwich Country Day-Stadium 2 | 4:00 p.m. | ||
| Sat., 10/2 | JV Football | Norwich Free Academy | Home - Darien HS-DHS Stadium East [Directions] | 2:00 p.m. | ||
| Sat., 10/2 | FR Football | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | FR Boys Soccer | Brien McMahon | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 3:30 p.m. | ||
| Sat., 10/2 | V Field Hockey | Daniel Hand | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | W 6-0 | |
| Sat., 10/2 | JV Field Hockey | Daniel Hand | Home - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 10/2 | FR Field Hockey | Trumbull | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 2:00 p.m. | ||
| Sat., 10/2 | FR Girls Soccer | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/2 | V Girls Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 2:00 p.m. | W 3-0 | |
| Sat., 10/2 | JV Girls Volleyball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 10/4 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:15 p.m. | Darien 159 New Canaan 154 | |
| Mon., 10/4 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:00 p.m. | ||
| Mon., 10/4 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 10/4 | JV Girls Soccer | Greenwich | Away - Cos Cob Park-Binney Park [Directions] | 4:45 p.m. | ||
| Mon., 10/4 | FR Girls Soccer | Greenwich Country Day | Away - GCDS Old church Fields | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Cross Country | Greenwich, Fairfield Warde, New Canaan | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Golf | Greenwich | Home - Country Club of Darien [Directions] | 3:15 p.m. | Darien 169 Greenwich 166 | |
| Tue., 10/5 | JV Boys Golf | Greenwich | Home - Country Club of Darien [Directions] | 3:10 p.m. | ||
| Tue., 10/5 | V Boys Soccer | Greenwich | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 10/5 | JV Boys Soccer | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Cross Country | Greenwich, Fairfield Warde, New Canaan | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Diving | St. Joseph | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/5 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 8-0 | |
| Tue., 10/5 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/5 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/5 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Field Hockey | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | V Girls Soccer | Danbury | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 10/6 | JV Girls Soccer | Danbury | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Girls Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Girls Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/7 | FR Football | Fairfield Warde | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Boys Golf | Chappa | Away - Longshore Golf Course | 3:15 p.m. | ||
| Thu., 10/7 | JV Boys Golf | New Canaan | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Thu., 10/7 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | T 0-0 | |
| Thu., 10/7 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Field Hockey | Trumbull | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 5-1 | |
| Thu., 10/7 | JV Field Hockey | Trumbull | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 10/7 | V Girls Volleyball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 10/7 | JV Girls Volleyball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/8 | V Girls Soccer | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | L 3-0 | |
| Fri., 10/8 | JV Girls Soccer | St. Joseph | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | V Girls Swimming and Diving | St. Joseph | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/8 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/8 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Sat., 10/9 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 10:00 a.m. | T 1-1 | |
| Sat., 10/9 | FR Boys Soccer | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 11:30 a.m. | ||
| Sat., 10/9 | V Girls Diving | Fairfield Warde | Home - New Canaan YMCA-Pool [Directions] | 9:00 a.m. | ||
| Sat., 10/9 | V Field Hockey | Guilford | Home - Darien HS-DHS Stadium Field [Directions] | 10:30 a.m. | W 6-0 | |
| Sat., 10/9 | JV Field Hockey | Guilford | Home - Darien HS-DHS Stadium Field [Directions] | 12:00 p.m. | ||
| Sat., 10/9 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Postponed | ||
| Sat., 10/9 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/11 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | W 8-0 | |
| Mon., 10/11 | JV Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 10/11 | V Girls Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/11 | JV Girls Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/12 | V Boys Cross Country | Fairfield Ludlowe, Stamford, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Darien 167 Danbury 192 | |
| Tue., 10/12 | JV Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:20 p.m. | ||
| Tue., 10/12 | FR Boys Soccer | Greenwich Country Day | Home - Darien HS-MMS (Middlesex) Lower Field at 30 Edgerton Street [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Cross Country | Fairfield Ludlowe, Stamford, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Diving | New Canaan | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/12 | FR Field Hockey | Fairfield Warde | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 2-1 | |
| Wed., 10/13 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/13 | JV Boys Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | W 5-0 | |
| Wed., 10/13 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:30 p.m. | ||
| Wed., 10/13 | FR Field Hockey | Norwalk | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | JV Girls Soccer | New Canaan | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | FR Girls Soccer | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Girls Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/13 | V Girls Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/13 | JV Girls Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/13 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 10/14 | FR Football | Wilton | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Girls Soccer | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | L 2-3 | |
| Thu., 10/14 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | V Boys Soccer | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 10/15 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/15 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 10/16 | V Football | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | W 56-36 | |
| Sat., 10/16 | FR Boys Soccer | Stamford | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/16 | FR Field Hockey | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 11:00 a.m. | ||
| Sat., 10/16 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | JV Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 8:30 a.m. | ||
| Sat., 10/16 | FR Girls Volleyball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | ||
| Mon., 10/18 | JV Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division I Boys Golf Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/18 | V Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 5-1 | |
| Mon., 10/18 | JV Field Hockey | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 10/18 | V Girls Soccer | Stamford | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/18 | JV Girls Soccer | Stamford | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/18 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/18 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/19 | JV Boys Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Boys Cross Country | FCIAC Championships @ Waveny Park, New Canaan | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/20 | FR Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 10/20 | JV Boys Soccer | Ridgefield | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | FR Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | FCIAC Championships @ Waveny Park, New Canaan | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/20 | FR Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 10/20 | FR Girls Soccer | Danbury | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Wed., 10/20 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/20 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/21 | V Girls Soccer | Wilton | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 10/21 | JV Girls Soccer | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | W 50-27 | |
| Fri., 10/22 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | W 4-2 | |
| Fri., 10/22 | JV Boys Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 1-2 | |
| Fri., 10/22 | JV Field Hockey | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 10/22 | JV Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 6:00 p.m. | ||
| Fri., 10/22 | V Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/22 | JV Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/23 | JV Football | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Sat., 10/23 | FR Boys Soccer | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/23 | FR Field Hockey | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 2:00 p.m. | ||
| Sat., 10/23 | FR Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | JV Girls Volleyball | East Haven JV Volleyball Invite | Away - East Haven HS-Gym | 8:00 a.m. | ||
| Sat., 10/23 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 2:00 p.m. | ||
| Mon., 10/25 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/25 | JV Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Mon., 10/25 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/26 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Tue., 10/26 | FR Girls Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | V Boys Soccer | Fairfield Warde | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | T 1-1 | |
| Wed., 10/27 | JV Boys Soccer | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | Postponed | ||
| Wed., 10/27 | FR Girls Soccer | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:30 p.m. | ||
| Wed., 10/27 | FR Girls Volleyball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/28 | V Boys Cross Country | Danbury Hatter Freshmen Invitational @ Tarrywile Park, Danbury | Away - Tarrywile Park | TBA | ||
| Thu., 10/28 | FR Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | FR Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:45 p.m. | W 8-0 | |
| Thu., 10/28 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-1 | |
| Thu., 10/28 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Fri., 10/29 | V Boys Soccer | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | ||
| Fri., 10/29 | V Field Hockey | Trumbull | Home - Darien HS-DHS Stadium Field [Directions] | 3:45 p.m. | W 8-0 | |
| Fri., 10/29 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/29 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 10/29 | FR Girls Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 10/30 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 2:00 p.m. | W 42-14 | |
| Sat., 10/30 | V Girls Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | W 3-0 | |
| Sat., 10/30 | JV Girls Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class L Championship | Away - Wickham Park | 11:25 a.m. | ||
| Mon., 11/1 | JV Football | St. Joseph | Home - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class L Championship | Away - Wickham Park | 11:55 a.m. | ||
| Mon., 11/1 | V | Unified Sports @ Staples HS | Away - TBA | 4:00 p.m. | ||
| Tue., 11/2 | V Field Hockey | Staples | Home - Brien McMahon HS-Casagrande Field [Directions] | 7:30 p.m. | W 2-1 | |
| Tue., 11/2 | V Girls Volleyball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 11/3 | V Girls Soccer | Trumbull (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 11/3 | V Girls Swimming and Diving | FCIAC Girls Swim Trials | Away - Greenwich HS | 5:00 p.m. | ||
| Thu., 11/4 | FR Football | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 11/4 | V Girls Swimming and Diving | FCIAC Girls Diving Finals | Away - Fairfield County Interscholastic Athletic Conferen-Westhill HS | 5:00 p.m. | ||
| Thu., 11/4 | V Girls Volleyball | Fairfield Ludlowe | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Norwalk | Home - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 49-21 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 3:00 p.m. | ||
| Sat., 11/6 | V Girls Swimming and Diving | FCIAC Girls Swim Finals | Away - Fairfield County Interscholastic Athletic Conferen-Greenwich HS | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Greenwich HS | ||||||
| Sat., 11/6 | V Girls Volleyball | Greenwich | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 11/8 | V Girls Soccer | Southington | Away - Southington HS-TURF FIELD [Directions] | 5:00 p.m. | ||
| Tue., 11/9 | V Boys Soccer | New Britain | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | ||
| Wed., 11/10 | V Field Hockey | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 11/10 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/11 | FR Football | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Thu., 11/11 | V Boys Soccer | Ridgefield | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | ||
| Thu., 11/11 | V Girls Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/12 | V Field Hockey | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 1-0 | |
| Sat., 11/13 | V Boys Cross Country | New England Championship @ Thetford Academy, VT | Away - Thetford Academy | TBA | ||
| Sat., 11/13 | V Football | Brien McMahon | Home - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | W 35-0 | |
| Sat., 11/13 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 12:00 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sat., 11/13 | V Girls Volleyball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 11/15 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Tue., 11/16 | V Field Hockey | Wilton | Home - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | ||
| Tue., 11/16 | V Girls Swimming and Diving | CIAC Class L Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Wed., 11/17 | V Girls Volleyball | Greenwich | Away - Stamford HS [Directions] | 5:00 p.m. | ||
| Thu., 11/18 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Mon., 11/22 | JV Football | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 11/25 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | L 7-12 | |
| Tue., 11/30 | V Football | Hamden | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | ||
| Thu., 12/2 | JV Boys Squash | v Greenwich | Home - Ox Ridge Club [Directions] | 8:00 p.m. | ||
| Thu., 12/2 | JV Girls Squash | v Rye Blk @ MSquash Portchester | Away - Not Listed | 8:00 p.m. | ||
| Sat., 12/4 | V Boys Ice Hockey | Scrimmage v Marshfield, MA | Home - Darien Ice House-Ice Rink [Directions] | 3:50 p.m. | ||
| Sat., 12/4 | V Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 7:30 p.m. | ||
| Sun., 12/5 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 12:30 p.m. | ||
| Mon., 12/6 | V Boys Squash | v Greenwich | Home - Ox Ridge Club [Directions] | 8:00 p.m. | ||
| Tue., 12/7 | JV Girls Squash | v WP JV @ MSquash Sono | Away - Not Listed | 8:00 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 6-2 | |
| Wed., 12/8 | V Girls Squash | v Bronxville @ Chelsea Piers | Away - Chelsea Piers - Stamford | 7:30 p.m. | ||
| Thu., 12/9 | JV Boys Squash | v Briarcliff @ M-Squash Portchester | Away - Not Listed | 8:00 p.m. | ||
| Fri., 12/10 | V Girls Basketball | Weston (Scrim.) | Away - Weston HS-Gym (New) [Directions] | 6:30 p.m. | ||
| Sat., 12/11 | V Football | Fairfield Prep | Away - Trumbull HS-McDougall Stadium [Directions] | 3:00 p.m. | ||
| Sat., 12/11 | V Boys Ice Hockey | St. Johns Prep (MA) (Scrim.) | Home - Stamford Twin Rinks-West [Directions] | 11:15 a.m. | ||
| Sat., 12/11 | JV Boys Ice Hockey | New Canaan (Scrim.) | Home - Stamford Twin Rinks-West [Directions] | 8:20 p.m. | ||
| Sat., 12/11 | V Wrestling | Suffield/Windsor Locks, Canton, Coventry, Granby Memorial, Portland, Rockville | Away - Suffield HS | 9:00 a.m. | ||
| Sat., 12/11 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 10-2 | |
| Sun., 12/12 | V Boys Ice Hockey | Xaverian Brothers (MA) (Scrim.) | Away - Xaverian Brothers HS-Canton Ice House | 1:30 p.m. | ||
| Mon., 12/13 | JV Boys Squash | v New Canaan @ MSquash- Sono | Away - Not Listed | 8:00 p.m. | ||
| Mon., 12/13 | V Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 5:30 p.m. | W 54-7 | |
| Tue., 12/14 | V Girls Squash | v New Canaan @ Chelsea Piers | Away - Chelsea Piers - Stamford | 7:30 p.m. | ||
| Wed., 12/15 | V Boys Ice Hockey | Hamden | Home - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | W 2-1 | |
| Wed., 12/15 | V Boys Squash | v New Canaan @ MSquash- Sono | Away - Sono Ice House | 7:45 p.m. | ||
| Wed., 12/15 | V Wrestling | Norwalk | Home - Darien HS-DHS South Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/16 | V Boys Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | L 41-66 | |
| Thu., 12/16 | JV Boys Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/16 | V Boys Squash | v Greens Farms Academy- away | Away - Greens Farm Academy | 4:00 p.m. | ||
| Thu., 12/16 | JV Boys Squash | v Greens Farms Academy- away | Away - Not Listed | 4:00 p.m. | ||
| Thu., 12/16 | V Boys Swimming and Diving | Greenwich | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | L 18-38 | |
| Thu., 12/16 | JV Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/16 | V Girls Squash | v Greens Farms Academy- away | Away - Not Listed | 4:00 p.m. | ||
| Thu., 12/16 | JV Girls Squash | v Greens Farms Academy- away | Away - Not Listed | 4:00 p.m. | ||
| Fri., 12/17 | FR Boys Basketball | Bassick | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/17 | V Boys Diving | Greenwich, TBA | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 12/17 | JV Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Fri., 12/17 | V Girls Indoor Track | Girls Indoor Track Meet at the Armory | Away - The Armory | 4:00 p.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Northwest Catholic | Away - Simsbury - ISCC-Olympic [Directions] | 6:20 p.m. | T 3-3(OT) | |
| Sat., 12/18 | JV Boys Ice Hockey | Greenwich | Home - Stamford Twin Rinks-West [Directions] | 8:20 p.m. | ||
| Sat., 12/18 | V Boys Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Fairfield Warde | Away - Wilton HS-Wilton Field House | 11:00 a.m. | ||
| Sat., 12/18 | V Wrestling | Darien Invitational | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 12/18 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | W 3-0 | |
| Sat., 12/18 | V Girls Indoor Track | FCIAC, Brien McMahon, Fairfield Warde | Away - Wilton HS-Wilton Field House | 11:00 a.m. | ||
| Mon., 12/20 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | L 53-60 | |
| Mon., 12/20 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/20 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | Postponed | ||
| Mon., 12/20 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice House-Ice Rink [Directions] | 8:10 p.m. | W 8-0 | |
| Wed., 12/22 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 2-0 | |
| Wed., 12/22 | FR Girls Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/23 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 2:30 p.m. | ||
| Thu., 12/23 | V Boys Indoor Track | Hillhouse Holiday Invitational @ Hillhouse HS | Away - Not Listed | 3:30 p.m. | ||
| Thu., 12/23 | V Wrestling | Ridgefield | Away - Ridgefield HS-Aux Gym [Directions] | 2:30 p.m. | ||
| Thu., 12/23 | V Girls Indoor Track | Hillhouse Holiday Invitational @ Hillhouse HS | Away - Not Listed | 3:30 p.m. | ||
| Thu., 12/23 | JV Girls Squash | v New Canaan JV | Home - Ox Ridge Club [Directions] | 7:45 p.m. | ||
| Tue., 12/28 | V Boys Basketball | Wright Tech | Home - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | W 77-31 | |
| Tue., 12/28 | JV Boys Basketball | Wright Tech | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | ||
| Tue., 12/28 | FR Boys Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Tue., 12/28 | V Wrestling | Avon, Bristol Central, Canton, Conard, Haddam-Killingworth, TBA, TBA | Away - Avon HS-Large Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Wed., 12/29 | V Boys Ice Hockey | Greenwich | Away - Greenwich Skating Club-Ice Rink [Directions] | 4:00 p.m. | W 4-2 | |
| Wed., 12/29 | JV Boys Ice Hockey | Greenwich | Away - Greenwich Skating Club-Ice Rink [Directions] | 10:30 a.m. | ||
| Wed., 12/29 | V Wrestling | Fairfield Prep | Away - Fairfield University-Brissette Gymnasium [Directions] | 1:45 p.m. | ||
| Thu., 12/30 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | L 19-29 | |
| Thu., 12/30 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/4 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 28-30 | |
| Tue., 1/4 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/6 | V Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 6:00 p.m. | W 78-30 | |
| Thu., 1/6 | JV Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 1/6 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | ||
| Sat., 1/8 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 1:00 p.m. | W 61-37 | |
| Sat., 1/8 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | Postponed | ||
| Sat., 1/8 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | Postponed | ||
| Sat., 1/8 | V Boys Ice Hockey | Bishop Hendricken (RI) | Home - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | L 2-3 | |
| Sat., 1/8 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Stamford Twin Rinks-West [Directions] | 8:20 p.m. | ||
| Sat., 1/8 | V Boys Indoor Track | Qualifying Meet #2A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sat., 1/8 | V Boys Squash | v Bronxville & Street Squash @ Street Squash facility | Away - Not Listed | 10:00 a.m. | ||
| Sat., 1/8 | JV Boys Squash | v Bronxville & Street Squash @ Street Squash facility- Harlem | Away - Not Listed | 11:00 a.m. | ||
| Sat., 1/8 | V Wrestling | Eric D'Agnese Memorial Tournament- Somers HS, Somers, NY | Away - Not Listed | Canceled | Cancelled | |
| Sat., 1/8 | V Girls Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | L 29-45 | |
| Sat., 1/8 | JV Girls Basketball | Norwalk | Home - Darien HS-DHS Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 1/8 | V Girls Gymnastics | New Canaan, Wilton | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien 126.65 Wilton 118.45 New Canaan 61.7 | |
| Sat., 1/8 | V Girls Indoor Track | Qualifying Meet #2A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sun., 1/9 | V Boys Ice Hockey | LaSalle Academy (RI) | Home - Darien Ice House-Ice Rink [Directions] | 3:40 p.m. | L 1-2 | |
| Sun., 1/9 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 7:30 p.m. | ||
| Mon., 1/10 | JV Boys Squash | v Rye | Home - Ox Ridge Club [Directions] | 8:00 p.m. | ||
| Mon., 1/10 | V Girls Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 8:20 p.m. | L 1-3 | |
| Tue., 1/11 | V Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 54-69 | |
| Tue., 1/11 | JV Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/11 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice House-Ice Rink [Directions] | 7:50 p.m. | W 7-0 | |
| Wed., 1/12 | FR Boys Basketball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | Postponed | ||
| Wed., 1/12 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | W 2-1(OT) | |
| Wed., 1/12 | V Wrestling | Wilton | Home - Darien HS-DHS South Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/14 | V Boys Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 60-49 | |
| Fri., 1/14 | JV Boys Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/14 | JV Boys Ice Hockey | New Canaan | Away - New Canaan Winter Club-Rink [Directions] | 5:40 p.m. | ||
| Fri., 1/14 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Sat., 1/15 | FR Boys Basketball | Trumbull | Home - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 1/15 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 8:15 p.m. | W 5-1 | |
| Sat., 1/15 | JV Boys Ice Hockey | St. Joseph | Home - Stamford Twin Rinks-East [Directions] | Postponed | ||
| Sat., 1/15 | V Boys Indoor Track | FCIAC, St. Joseph, Stamford, Staples | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/15 | V Wrestling | Bunnell, Derby/Oxford/Holy Cross, Weston | Home - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/15 | V Girls Basketball | Southington | Away - Southington HS-Gym West [Directions] | 1:00 p.m. | L 45-23 | |
| Sat., 1/15 | JV Girls Basketball | Southington | Away - Southington HS-Gym West [Directions] | 11:30 a.m. | ||
| Sat., 1/15 | V Girls Ice Hockey | v Westchester | Home - Stamford Twin Rinks-East [Directions] | 6:55 p.m. | ||
| Sat., 1/15 | V Girls Indoor Track | FCIAC, St. Joseph, Stamford, Staples | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/17 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 1:30 p.m. | L 60-65 | |
| Mon., 1/17 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 12:00 p.m. | ||
| Mon., 1/17 | V Boys Ice Hockey | Xavier | Home - Darien Ice House-Ice Rink [Directions] | 4:30 p.m. | L 5-6(OT) | |
| Mon., 1/17 | V Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 1:30 p.m. | L 51-25 | |
| Mon., 1/17 | JV Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | ||
| Mon., 1/17 | V Girls Gymnastics | Trumbull, New Canaan, St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 1:00 p.m. | Darien 126.35 St. Joe's 132.9 Trumbull 136.2 | |
| Tue., 1/18 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/18 | FR Girls Basketball | Fairfield Ludlowe | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/18 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:15 p.m. | W 6-0 | |
| Wed., 1/19 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 8:00 p.m. | L 4-6 | |
| Wed., 1/19 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/19 | V Wrestling | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/19 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | T 0-0(OT) | |
| Wed., 1/19 | JV Girls Squash | v Rye 2 @ MSquash Portchester | Away - Not Listed | 8:00 p.m. | ||
| Fri., 1/21 | V Boys Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 64-62 | |
| Fri., 1/21 | JV Boys Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/21 | FR Boys Basketball | Brien McMahon | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/21 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 54-21 | |
| Fri., 1/21 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Postponed | ||
| Sat., 1/22 | V Boys Basketball | Harding | Home - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | W 71-37 | |
| Sat., 1/22 | JV Boys Basketball | Harding | Home - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 1/22 | FR Boys Basketball | Harding | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 1-0 | |
| Sat., 1/22 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Stamford Twin Rinks-West [Directions] | 8:20 p.m. | ||
| Sat., 1/22 | V Boys Indoor Track | FCIAC, Brien McMahon, Danbury, Wilton | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sat., 1/22 | V Wrestling | Granby Memorial, Bacon Academy, East Hartford, East Haven, Montville, Suffield/Windsor Locks, Windsor | Away - Granby Memorial HS-K.L. King Gymnasium | 9:00 a.m. | ||
| Sat., 1/22 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 11:45 a.m. | W 33-17 | |
| Sat., 1/22 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 10:15 a.m. | ||
| Sat., 1/22 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien 128.3 Fairfield Warde 131.85 Fairfield Ludlowe 131.95 | |
| Sat., 1/22 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 3-0 | |
| Sat., 1/22 | V Girls Indoor Track | Qualifying Meet #4A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Mon., 1/24 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 7:00 p.m. | W 66-52 | |
| Mon., 1/24 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Mon., 1/24 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Mon., 1/24 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | L 1-5 | |
| Mon., 1/24 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-TBA [Directions] | 5:15 p.m. | ||
| Mon., 1/24 | V Boys Squash | v Scarsdale | Home - Ox Ridge Club [Directions] | 8:00 p.m. | ||
| Mon., 1/24 | V Girls Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 5:15 p.m. | W 55-24 | |
| Mon., 1/24 | JV Girls Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 6:45 p.m. | ||
| Wed., 1/26 | JV Boys Squash | v Fairfield @ Intensity | Away - Not Listed | 7:30 p.m. | ||
| Wed., 1/26 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/26 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/26 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:30 p.m. | Darien 127.45 Greenwich 120.6 | |
| Wed., 1/26 | V Girls Ice Hockey | Simsbury | Home - Darien Ice House-Ice Rink [Directions] | 3:40 p.m. | W 4-3 | |
| Thu., 1/27 | V Boys Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 43-72 | |
| Thu., 1/27 | JV Boys Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/27 | FR Boys Basketball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/27 | V Boys Diving | Fairfield Ludlowe, TBA, TBA | Home - New Canaan Y -Diving Only [Directions] | 3:00 p.m. | ||
| Thu., 1/27 | V Boys Squash | v Rye @ Lifetime | Away - Not Listed | 8:00 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 34-24 | |
| Thu., 1/27 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/27 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/27 | V Girls Squash | v Rye 1 | Home - Ox Ridge Club [Directions] | 7:45 p.m. | ||
| Fri., 1/28 | V Boys Ice Hockey | St. Joseph (Metuchen, NJ) | Away - St. Joseph HS Metuchen-Hockey Rink | 6:45 p.m. | Cancelled | |
| Fri., 1/28 | V Boys Swimming and Diving | Ridgefield | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 1/28 | V Wrestling | Brookfield/Shepaug | Away - Brookfield HS-BHS Small Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/28 | V Girls Gymnastics | Norwalk | Away - TBA [Directions] | 6:30 p.m. | Darien 129.75 Staples 128.2 Norwalk 73.9 | |
| Fri., 1/28 | V Girls Gymnastics | Staples | Away - Westport YMCA [Directions] | 6:30 p.m. | Darien 129.75 Staples 128.2 Norwalk 73.9 | |
| Sat., 1/29 | V Boys Squash | v Delbarton | Home - Ox Ridge Club [Directions] | Canceled | Cancelled | |
| Sat., 1/29 | V Wrestling | Norwalk, Brien McMahon, Fairfield Ludlowe, Fairfield Warde, Greens Farms Academy, Greenwich, TBA, TBA, TBA, Notre Dame-Fairfield, Ridgefield, St. Joseph, Staples, Trumbull, Weston | Away - Norwalk HS-Tom Scarso Gymnasium | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/29 | V Wrestling | Brookfield, Bethel, Canton, Danbury, Joel Barlow, Montville, New Canaan, Newtown, Pomperaug, Stratford, Harding, Wilton | Away - Brookfield HS-BHS Small & Big Gym | Canceled | Cancelled | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/30, Time to 11:00 a.m. | ||||||
| Sat., 1/29 | V Girls Squash | Home v DelBarton | Home - Ox Ridge Club [Directions] | Canceled | Cancelled | |
| Sun., 1/30 | V Boys Squash | v New Haven Lawn Club | Away - Not Listed | 1:00 p.m. | ||
| Mon., 1/31 | JV Boys Squash | v Westport | Home - Ox Ridge Club [Directions] | 7:45 p.m. | ||
| Mon., 1/31 | V Girls Ice Hockey | Morristown-Beard (NJ) | Away - Morristown-Beard School | 4:45 p.m. | Cancelled | |
| Tue., 2/1 | V Boys Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 40-51 | |
| Tue., 2/1 | JV Boys Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/1 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | 8:10 p.m. | W 4-3(OT) | |
| Tue., 2/1 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | L 42-36 | |
| Tue., 2/1 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Blue Rink [Directions] | 4:25 p.m. | T 3-3 | |
| Wed., 2/2 | FR Boys Basketball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/2 | V Boys Swimming and Diving | Westhill/Stamford | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/2 | V Wrestling | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/2 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 2/2 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 3:30 p.m. | L 1-4 | |
| Thu., 2/3 | V Boys Diving | Wilton | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Thu., 2/3 | V Boys Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/3 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 40-43 | |
| Thu., 2/3 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 2/3 | V Girls Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/3 | JV Girls Squash | v Greenwich | Home - Ox Ridge Club [Directions] | 7:45 p.m. | ||
| Fri., 2/4 | V Wrestling | Fairfield Warde, Fitch, TBA, St. Joseph | Away - Fairfield Warde HS-Small Gym [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Sat., 2/5 | JV Boys Ice Hockey | Ridgefield | Home - Stamford Twin Rinks-West [Directions] | 8:20 p.m. | ||
| Sat., 2/5 | V Wrestling | Fairfield Warde, Fitch, St. Joseph | Away - Fairfield Warde HS-Small Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/5 | V Girls Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | L 42-25 | |
| Sat., 2/5 | JV Girls Basketball | Wilton | Home - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/5 | FR Girls Basketball | Bridgeport Central | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | JV Competitive Cheerleading | FCIAC Cheer Championships | Away - Not Listed-Trumbull | 11:00 a.m. | ||
| Sat., 2/5 | V Girls Gymnastics | Stamford, Westhill | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien 126.7 Stamford 73.55 Westhill 47.05 | |
| Sat., 2/5 | V Girls Ice Hockey | East Catholic Coop | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 2-0 | |
| Mon., 2/7 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | W 55-54 | |
| Mon., 2/7 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/7 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/7 | JV Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | Canceled | Cancelled | |
| Mon., 2/7 | V Boys Squash | v Westport @ Intensity | Away - Not Listed | 7:30 p.m. | ||
| Mon., 2/7 | V Boys Swimming and Diving | Danbury | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 43-37 | |
| Mon., 2/7 | JV Girls Basketball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/8 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 54-66 | |
| Tue., 2/8 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/8 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/8 | V Wrestling | Westhill | Home - Darien HS-DHS South Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Wrestling | Trumbull | Home - Darien HS-DHS South Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/8 | V Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 28-45 | |
| Tue., 2/8 | JV Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/8 | V Girls Ice Hockey | Guilford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:00 p.m. | W 5-4 | |
| Tue., 2/8 | JV Girls Squash | v Rye Rd- @ MSquash SoNo | Away - Not Listed | 8:00 p.m. | ||
| Wed., 2/9 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 7:50 p.m. | W 5-0 | |
| Wed., 2/9 | FR Girls Basketball | St. Joseph | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/9 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms Ice Rink-Ice Rink [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 2/10 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:15 p.m. | L 47-60 | |
| Thu., 2/10 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/11 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 3:00 p.m. | ||
| Fri., 2/11 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:30 p.m. | ||
| Fri., 2/11 | V Wrestling | FCIAC, Danbury, Fairfield Ludlowe, Fairfield Warde, Greenwich, TBA, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 29-27 | |
| Fri., 2/11 | JV Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/11 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | Postponed | ||
| Sat., 2/12 | V Boys Ice Hockey | New Canaan | Home - Darien Ice House-Ice Rink [Directions] | 4:45 p.m. | W 3-2 | |
| Sat., 2/12 | JV Boys Ice Hockey | Fairfield Prep | Home - Stamford Twin Rinks-East [Directions] | 8:20 p.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/12 | V Boys Swimming and Diving | St. Joseph | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:00 p.m. | ||
| Sat., 2/12 | V Boys Swimming and Diving | Trumbull | Away - Orange Town Pool [Directions] | 3:00 p.m. | ||
| Sat., 2/12 | V Wrestling | FCIAC Wrestling Championships Wrestlebacks | Away - New Canaan HS-Main Gym | 10:00 a.m. | ||
| Sat., 2/12 | V Girls Basketball | Wilbur Cross | Home - Darien HS-DHS Main Gym [Directions] | 12:30 p.m. | W 43-39 | |
| Sat., 2/12 | JV Girls Basketball | Wilbur Cross | Home - Darien HS-DHS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/12 | FR Girls Basketball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Championships | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 11:00 a.m. | 133.85 6th place | |
| Sat., 2/12 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | L 0-5 | |
| Sat., 2/12 | V Girls Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/14 | V Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | L 37-48 | |
| Mon., 2/14 | JV Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 2/14 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 39-15 | |
| Mon., 2/14 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/14 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:15 p.m. | W 3-1 | |
| Tue., 2/15 | FR Boys Basketball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/16 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 59-57 | |
| Wed., 2/16 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 7:50 p.m. | W 4-1 | |
| Wed., 2/16 | V Girls Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 49-36 | |
| Wed., 2/16 | JV Girls Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/16 | V Girls Ice Hockey | Greenwich Academy | Away - Chelsea Piers - Field Side-North Rink | 3:30 p.m. | ||
| Thu., 2/17 | FR Girls Basketball | Stamford | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/18 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice House-Ice Rink [Directions] | 1:40 p.m. | L 1-3 | |
| Fri., 2/18 | V Wrestling | Class L Championship - Day 1 | Away - Wilton | 3:00 p.m. | ||
| Sat., 2/19 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | W 5-2 | |
| Sat., 2/19 | JV Boys Ice Hockey | Trumbull | Home - Stamford Twin Rinks-West [Directions] | 8:25 p.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class L Championship - Day 2 | Away - Wilton | 9:00 a.m. | ||
| Sat., 2/19 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 56-62 | |
| Mon., 2/21 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Mon., 2/21 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 2/23 | V Boys Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 55-66 | |
| Wed., 2/23 | JV Boys Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/23 | FR Boys Basketball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 2:30 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | L 1-4 | |
| Wed., 2/23 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Darien Ice House-Ice Rink [Directions] | 5:50 p.m. | ||
| Sat., 2/26 | V Boys Ice Hockey | Trumbull | Home - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Sat., 2/26 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-New [Directions] | 6:00 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Girls Gymnastics | CIAC Class M Divisional Championship | Away - Richetelli Gymnasium @Jonathan Law | 10:00 a.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Tue., 3/1 | JV Boys Ice Hockey | Xavier | Home - Blake Field - New Haven-Walker Rink [Directions] | 8:30 p.m. | ||
| Tue., 3/1 | V Boys Swimming and Diving | FCIAC Boys' Swim Trials | Away - Greenwich HS | 5:30 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | ||
| Wed., 3/2 | V Boys Swimming and Diving | FCIAC Diving Finals | Away - Westhill High-Westhill HS | 5:00 p.m. | ||
| Thu., 3/3 | JV Boys Ice Hockey | Fairfield Prep | Away - TBA [Directions] | 6:30 p.m. | ||
| Thu., 3/3 | V Boys Swimming and Diving | FCIAC Boys' Swim Finals | Away - Greenwich HS | 6:30 p.m. | ||
| Thu., 3/3 | V Girls Ice Hockey | Conard | Home - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Sat., 3/5 | V Competitive Cheerleading | Cheer State Finals @ Hillhouse HS | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Sat., 3/5 | V Girls Ice Hockey | Avon | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | ||
| Tue., 3/8 | V Boys Basketball | WCA | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 3/8 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 4:30 p.m. | ||
| Wed., 3/9 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 5:30 p.m. | No bus | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class L Diving Championships | Away - Sheehan | 6:30 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 6:30 p.m. | ||
| Sat., 3/12 | V Boys Ice Hockey | Northwest Catholic | Away - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | ||
| Mon., 3/14 | V | Unified Sports Tournament @ Ludlowe HS | Away - Fairfield Ludlowe HS-Main Gym | 4:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class L Swimming Championships | Away - Cornerstone Pool | 1:30 p.m. | ||
| Wed., 3/16 | V Boys Ice Hockey | Xavier | Away - West Haven HS-Bennett Rink [Directions] | 6:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | JV Boys Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 12:00 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Tue., 3/22 | V Boys Ice Hockey | Notre Dame-West Haven | Away - [CIAC] People's United Center-Quinnipiac-Ice Arena [Directions] | 6:30 p.m. | ||
| Tue., 3/22 | V Boys Lacrosse | scrimmage v Salisbury | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 3/23 | V Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:45 p.m. | ||
| Wed., 3/23 | JV Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 3:45 p.m. | ||
| Wed., 3/23 | FR Baseball | Westhill (Scrim.) | Away - Westhill HS-Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 3/23 | V Co-ed Sailing | Sailing Meet @ Pequot YC - Fairfield Prep, Ludlowe | Away - Pequot Yacht Club | 3:30 p.m. | ||
| Thu., 3/24 | V Boys Lacrosse | Blue v White intrasquad game | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 3/24 | JV Boys Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Sat., 3/26 | V Baseball | Pelham Memorial (NY) (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 9:00 a.m. | ||
| Sat., 3/26 | JV Baseball | Pelham Memorial (NY) (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 9:00 a.m. | ||
| Sat., 3/26 | V Boys Lacrosse | Delbarton (NJ) (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 8:00 a.m. | ||
| Sat., 3/26 | V Boys Volleyball | Joel Barlow, Masuk, TBA, Newtown, Wolcott Tech, Shelton, South Windsor, Xavier | Home - Darien HS-DHS Main Gym [Directions] | 8:30 a.m. | also using north & south gyms | |
| Sat., 3/26 | V Softball | Greenwich (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 12:00 p.m. | ||
| Sat., 3/26 | V Softball | Stamford (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 2:00 p.m. | ||
| Mon., 3/28 | V Girls Lacrosse | Sacred Heart of Greenwich (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Mon., 3/28 | JV Girls Lacrosse | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart Greenwich-Magnetti Turf Field | 4:30 p.m. | ||
| Tue., 3/29 | FR Baseball | New Canaan (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 3:45 p.m. | ||
| Wed., 3/30 | V Baseball | Wilton (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | JV Baseball | Wilton (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Boys Lacrosse | Fairfield Prep (Scrim.) | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | JV Boys Lacrosse | Fairfield Prep (Scrim.) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | FR Boys Lacrosse | Fairfield Prep (Scrim.) | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Co-ed Sailing | Sailing Meet @ Cedar Point YC - Westport vs GFA, SHS, FLHS | Away - Cedar Point Yacht Club | 3:30 p.m. | ||
| Wed., 3/30 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Turf field | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | Brien McMahon (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 3:45 p.m. | ||
| Thu., 3/31 | V Baseball | Greenwich (Scrim.) | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | Canceled | Cancelled | |
| Thu., 3/31 | JV Baseball | Greenwich (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | Canceled | Cancelled | |
| Sat., 4/2 | V Baseball | Stratford | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 2:00 p.m. | L 2-3 | |
| Sat., 4/2 | JV Baseball | Staples | Home - Darien HS-DHS Baseball - JV Field [Directions] | 2:00 p.m. | ||
| Sat., 4/2 | V Boys Rugby | Fairfield Warde | Home - Royle School Field [Directions] | 1:00 p.m. | ||
| Sat., 4/2 | V Boys Volleyball | Farmington | Away - Farmington HS [Directions] | 1:00 p.m. | W 3-0 | |
| Sat., 4/2 | JV Boys Volleyball | Farmington | Away - Farmington HS [Directions] | 12:00 p.m. | ||
| Sat., 4/2 | V Softball | Newtown | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 1:00 p.m. | L 1-4 | |
| Mon., 4/4 | V Baseball | New Fairfield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 4/4 | JV Baseball | New Fairfield | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:30 p.m. | ||
| Mon., 4/4 | V Softball | Joel Barlow | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | W 13-0 | |
| Tue., 4/5 | FR Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Lacrosse | Brien McMahon | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 16-2 [Detailed Results] | |
| Tue., 4/5 | JV Boys Lacrosse | Brien McMahon | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:30 p.m. | ||
| Tue., 4/5 | V Boys Outdoor Track | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Volleyball | Iona Prep (NY) | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 4/5 | JV Boys Volleyball | Iona Prep (NY) | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | Darien 209 Wilton 192 Non fciac | |
| Tue., 4/5 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 20-1 | |
| Tue., 4/5 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Tue., 4/5 | V Girls Outdoor Track | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | JV Girls Tennis | Fairfield Ludlowe | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | JV Baseball | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | FR Baseball | Westhill (Scrim.) | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | FR Boys Lacrosse | St. Joseph | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Co-ed Sailing | Sailing Meet @ Grass Island - Greenwich vs GCDS, GHS, BMHS, FGA, FP | Away - Indian Harbor Yacht Club | 3:30 p.m. | ||
| Wed., 4/6 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | Darien 214 Warde 243 | |
| Wed., 4/6 | V Girls Lacrosse | Manhassett (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 6:00 p.m. | W 14-7 | |
| Wed., 4/6 | JV Girls Lacrosse | Manhassett (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 6:00 p.m. | ||
| Wed., 4/6 | V Girls Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/7 | JV Boys Lacrosse | Brunswick School | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 4/7 | V Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | Postponed | ||
| Fri., 4/8 | JV Baseball | Stamford | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | FR Baseball | Newtown | Home - Darien HS-Town Hall Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 4/8 | FR Boys Lacrosse | Wilton | Away - Wilton HS-Whitten Field [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | JV Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 4/8 | V Boys Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 4/8 | JV Boys Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 4/8 | FR Girls Lacrosse | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 4/9 | V Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 1:00 p.m. | W 15-12 | |
| Sat., 4/9 | JV Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 10:00 a.m. | ||
| Sat., 4/9 | FR Boys Lacrosse | Chaminade (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Victor (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | W 10-9 | |
| Sat., 4/9 | V Softball | Bridgeport Central | Away - Bridgeport Central HS-Cal Ripken Turf Field [Directions] | 11:00 a.m. | W 16-0 | |
| Mon., 4/11 | V Baseball | Wilbur Cross | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 8-1 | |
| Mon., 4/11 | FR Baseball | Westhill | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/11 | FR Girls Lacrosse | Trumbull | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Norwalk | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/12 | V Baseball | Cheshire | Away - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 4/12 | V Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 15-9 | |
| Tue., 4/12 | JV Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 4/12 | V Boys Tennis | Westhill | Home - Darien HS-DHS Tennis Courts [Directions] | 1:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 4/12 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 10:00 a.m. | W 19-10 | |
| Tue., 4/12 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 11:30 a.m. | ||
| Tue., 4/12 | V Softball | Stamford | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 5-4 | |
| Tue., 4/12 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 2:00 p.m. | W 6-1 | |
| Tue., 4/12 | JV Girls Tennis | Trumbull | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | JV Baseball | Fairfield Prep | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | FR Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | FR Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 10:00 a.m. | W 3-0 | |
| Wed., 4/13 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 11:30 a.m. | ||
| Wed., 4/13 | V Girls Lacrosse | Ridgewood (NJ) | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | W 15-4 | |
| Wed., 4/13 | JV Girls Lacrosse | Ridgewood (NJ) | Home - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Wed., 4/13 | FR Girls Lacrosse | Ridgewood (NJ) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 4/14 | V Baseball | Norwalk | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 2:30 p.m. | L 1-7 | |
| Thu., 4/14 | JV Baseball | Norwalk | Home - Darien HS-DHS Baseball - JV Field [Directions] | 2:30 p.m. | ||
| Thu., 4/14 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 2:30 p.m. | ||
| Thu., 4/14 | V Boys Tennis | Trumbull | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-0 [Detailed Results] | |
| Thu., 4/14 | V Boys Volleyball | Masuk | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 4/14 | JV Boys Volleyball | Masuk | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 4/14 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 2:30 p.m. | W 7-0 | |
| Thu., 4/14 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/14 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/16 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 11:00 a.m. | L 2-10 | |
| Sat., 4/16 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | L 10-11 | |
| Sat., 4/16 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/16 | FR Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 12:00 p.m. | ||
| Sat., 4/16 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 4/16 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 11:30 a.m. | ||
| Sat., 4/16 | V Softball | Brookfield | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 1:00 p.m. | L 8-4 | |
| Mon., 4/18 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 0-6 | |
| Mon., 4/18 | JV Baseball | Westhill | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | FR Baseball | Westhill | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | JV Boys Lacrosse | Manhassett (NY) | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:30 p.m. | ||
| Mon., 4/18 | FR Boys Lacrosse | Fairfield Prep | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/18 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/18 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/18 | V Softball | Westhill | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 15-2 | |
| Mon., 4/18 | V Girls Tennis | Fairfield Ludlowe | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/19 | V Boys Lacrosse | Yorktown (NY) | Away - Yorktown Heights HS-Lacrosse Field | 7:00 p.m. | W 9-8 | |
| Tue., 4/19 | JV Boys Lacrosse | Yorktown (NY) | Away - Yorktown Heights HS-Lacrosse Field | 4:30 p.m. | ||
| Tue., 4/19 | V Boys Tennis | Brien McMahon | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/19 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | Postponed | ||
| Tue., 4/19 | V Girls Golf | New Canaan | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 246 New Canaan 189 | |
| Tue., 4/19 | V Girls Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 15-11 | |
| Tue., 4/19 | JV Girls Lacrosse | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 4/19 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/20 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 3-6 | |
| Wed., 4/20 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Baseball | Trumbull | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/20 | V Boys Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 4/20 | JV Boys Volleyball | Ridgefield | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Co-ed Sailing | Sailing Meet @ Indian Harbor - Greenwich vs BS, GA, GCDS | Home - Indian Harbor Yacht Club [Directions] | 3:30 p.m. | ||
| Wed., 4/20 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 14-8 | |
| Wed., 4/20 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Wed., 4/20 | FR Girls Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Softball | Trumbull | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 12-1 | |
| Wed., 4/20 | V Girls Tennis | Bridgeport Central | Home - Darien HS-DHS Tennis Courts [Directions] | 2:30 p.m. | W 7-0 | |
| Thu., 4/21 | FR Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | Postponed | ||
| Thu., 4/21 | V Girls Rugby | Trumbull | Home - Royle School Field [Directions] | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/23 | ||||||
| Fri., 4/22 | V Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 4/22 | JV Baseball | Fairfield Ludlowe | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Baseball | Fairfield Ludlowe | Home - Darien HS-Town Hall Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Boys Lacrosse | Wilton | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Boys Outdoor Track | Distance Festival | Away - Hall HS-Stadium (Track) | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 4/22 | JV Boys Tennis | New Canaan | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/22 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/22 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | L 6-1 | |
| Fri., 4/22 | JV Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 5:30 p.m. | ||
| Sat., 4/23 | V Boys Lacrosse | Manhassett (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 1:00 p.m. | W 13-11 | |
| Sat., 4/23 | V Boys Outdoor Track | Hillhouse | Away - Bowen Field-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 4/23 | JV Softball | Westhill | Home - Darien HS-DHS - Softball - JV Field [Directions] | 10:00 a.m. | ||
| Sat., 4/23 | JV Girls Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Sun., 4/24 | V Co-ed Sailing | Sailing CT Fleet Race Championship @ Black Rock YC - Bridgeport | Away - Black Rock Yacht Club | 10:00 a.m. | ||
| Mon., 4/25 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 4/25 | JV Baseball | Brien McMahon | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:30 p.m. | ||
| Mon., 4/25 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/25 | JV Boys Tennis | Staples | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 4/25 | JV Boys Volleyball | Danbury | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 4/25 | V Girls Golf | Wilton | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 233 Wilton 203 | |
| Mon., 4/25 | V Girls Lacrosse | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 16-5 | |
| Mon., 4/25 | JV Girls Lacrosse | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 4/25 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:30 p.m. | ||
| Mon., 4/25 | V Softball | Harding | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 20-1 | |
| Mon., 4/25 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 16-3 | |
| Tue., 4/26 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:45 p.m. | ||
| Tue., 4/26 | V Boys Outdoor Track | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Golf | Staples | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 231 Staples 185 | |
| Tue., 4/26 | V Girls Lacrosse | Fairfield Warde | Home - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | W 20-2 | |
| Tue., 4/26 | JV Girls Lacrosse | Fairfield Warde | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:30 p.m. | ||
| Tue., 4/26 | V Girls Outdoor Track | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Softball | Brien McMahon | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 3-2 | |
| Wed., 4/27 | V Baseball | Bridgeport Central | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 12-1 | |
| Wed., 4/27 | JV Baseball | Bassick | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | FR Baseball | Fairfield Prep | Home - Darien HS-Town Hall Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | FR Boys Lacrosse | Newtown | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Greenwich | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Wed., 4/27 | JV Boys Tennis | Greenwich | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/27 | JV Boys Volleyball | Westhill | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Co-ed Sailing | Sailing Meet @ Noroton YC vs BMHS | Home - Noroton Yacht Club [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | JV Girls Golf | New Canaan | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Wed., 4/27 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/27 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Lacrosse | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 15-10 | |
| Thu., 4/28 | JV Boys Lacrosse | Staples | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 4/28 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/28 | V Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 4/28 | JV Boys Volleyball | New Canaan | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Darien 221 Danbury 262 | |
| Thu., 4/28 | JV Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:00 p.m. | ||
| Thu., 4/28 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 17-1 | |
| Thu., 4/28 | JV Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | ||
| Thu., 4/28 | V Girls Outdoor Track | Penn Relays @ University of Pennsylvania | Away - University of Pennsylvania-Franklin Field | 10:00 a.m. | ||
| Thu., 4/28 | V Girls Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Thu., 4/28 | V Girls Tennis | Danbury | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 4/28 | JV Girls Tennis | St. Joseph | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | L 1-7 | |
| Fri., 4/29 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Fri., 4/29 | FR Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Lacrosse | Norwalk | Home - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 21-0 | |
| Fri., 4/29 | JV Boys Lacrosse | Norwalk | Home - Darien HS-DHS Center Oval - Turf [Directions] | 5:30 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/29 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Girls Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Softball | Staples | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 19-9 | |
| Fri., 4/29 | JV Softball | Staples | Home - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Sat., 4/30 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 9-7 | |
| Sat., 4/30 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Sat., 4/30 | FR Boys Lacrosse | Connor Cornish Tournament @ Don Bosco HS vs Westfield | Away - Not Listed | 11:30 a.m. | ||
| Sat., 4/30 | V Boys Outdoor Track | 40th O'Grady Relays @ Danbury HS | Away - Danbury HS | 9:00 a.m. | ||
| Sat., 4/30 | V Boys Rugby | Harvey School (NY) (Scrim.) | Home - Royle School Field [Directions] | Canceled | Cancelled | |
| Sat., 4/30 | V Girls Outdoor Track | 40th O'Grady Relays @ Danbury HS | Away - Danbury HS | 9:00 a.m. | ||
| Sat., 4/30 | JV Softball | Brien McMahon | Home - Darien HS-DHS - Softball - JV Field [Directions] | 10:30 a.m. | ||
| Sun., 5/1 | V Co-ed Sailing | Sailing Fleet Race Oday Qualifier @ UCONN Avery Point OR Hotchkiss School | Away - UCONN Avery Point | 9:00 a.m. | ||
| Mon., 5/2 | FR Boys Lacrosse | Kellenberg Memorial (NY) | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:15 p.m. | ||
| Mon., 5/2 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/2 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Girls Lacrosse | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 4:15 p.m. | W 12-8 | |
| Mon., 5/2 | JV Girls Lacrosse | Wilton | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 5/2 | FR Girls Lacrosse | Fairfield Warde | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | JV Girls Tennis | Greenwich | Home - Weed Beach Tennis Courts [Directions] | Postponed | ||
| Tue., 5/3 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | L 0-1 | |
| Tue., 5/3 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | FR Baseball | Greenwich | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 18-0 | |
| Tue., 5/3 | JV Boys Lacrosse | Stamford | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 5/3 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/3 | JV Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 5:30 p.m. | ||
| Tue., 5/3 | V Girls Golf | Fairfield Ludlowe | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 233 Ludlowe 233 | |
| Tue., 5/3 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Softball | Greenwich | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | W 7-1 | |
| Tue., 5/3 | V Girls Tennis | New Canaan | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/3 | JV Girls Tennis | New Canaan | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | V Baseball | Danbury | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 3-5 | |
| Wed., 5/4 | JV Baseball | Danbury | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/4 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | Postponed | ||
| Wed., 5/4 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/4 | JV Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 5/4 | V Co-ed Sailing | Sailing Greenwich Clean Up Day @ Indian Harbor YC OR Grass Island | Away - Indian Harbor Yacht Club | 3:30 p.m. | ||
| Wed., 5/4 | JV Girls Golf | Greenwich | Home - Woodway Country Club [Directions] | Postponed | ||
| Wed., 5/4 | V Girls Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 7:00 p.m. | W 12-7 | |
| Wed., 5/4 | JV Girls Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 5:00 p.m. | ||
| Wed., 5/4 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:00 p.m. | L 0-6 | |
| Thu., 5/5 | V Baseball | St. Joseph | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 7-4 | |
| Thu., 5/5 | FR Baseball | St. Joseph | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | Brunswick School | Away - Brunswick Cosby Turf Field | 7:00 p.m. | ||
| Thu., 5/5 | JV Boys Lacrosse | Brunswick School | Away - Brunswick Cosby Turf Field | 4:30 p.m. | ||
| Thu., 5/5 | JV Boys Lacrosse | Brunswick School | Away - Brunswick-Edwards Campus-Grass | 4:30 p.m. | ||
| Thu., 5/5 | FR Boys Lacrosse | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | V Boys Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Thu., 5/5 | JV Boys Tennis | Ridgefield | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 5/5 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 2:30 p.m. | Darien 226 Ridgefield 218 | |
| Thu., 5/5 | JV Girls Golf | Greenwich Country Day | Home - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Thu., 5/5 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 19-2 | |
| Thu., 5/5 | JV Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Girls Rugby | Greenwich | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/5 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | FR Baseball | St. Joseph | Home - Darien HS-DHS Baseball - JV Field [Directions] | Canceled | Cancelled | |
| Fri., 5/6 | V Boys Rugby | Darien Rugby vs Fordham Prep | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Fri., 5/6 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Fri., 5/6 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Sat., 5/7 | V Boys Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | W 19-18 | |
| Sat., 5/7 | JV Boys Lacrosse | St. Anthonys (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Sat., 5/7 | FR Boys Lacrosse | Don Bosco (NJ) | Away - Don Bosco Prep School-Stadium Turf | 1:30 p.m. | ||
| Sat., 5/7 | V Boys Tennis | St. Joseph | Home - Solaris Racquet Club [Directions] | 6:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 5/7 | V Girls Lacrosse | Garden City (NY) | Home - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | Cancelled | |
| Sat., 5/7 | JV Girls Lacrosse | Garden City (NY) | Home - Darien HS-DHS Stadium Field [Directions] | Canceled | Cancelled | |
| Sat., 5/7 | V Girls Tennis | St. Joseph | Home - Solaris Racquet Club [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/9 | V Baseball | New Canaan | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 4-12 | |
| Mon., 5/9 | JV Baseball | New Canaan | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | JV Boys Lacrosse | Staples (Scrim.) | Away - Staples HS-Wakeman Field B (turf) [Directions] | 5:30 p.m. | ||
| Mon., 5/9 | FR Boys Lacrosse | New Canaan | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Outdoor Track | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/9 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/9 | JV Boys Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/9 | V Girls Lacrosse | Moorestown (NJ) | Away - MOORESTOWN - SALEM RD/PRYOR PARK-S1 | 6:00 p.m. | W 17-7 | |
| Mon., 5/9 | JV Girls Lacrosse | Moorestown (NJ) | Away - MOORESTOWN - SALEM RD/PRYOR PARK-S1 | 4:30 p.m. | ||
| Mon., 5/9 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Girls Outdoor Track | Ridgefield | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 6:00 p.m. | L 2-0 | |
| Mon., 5/9 | V Girls Tennis | Stamford | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/9 | JV Girls Tennis | Fairfield Warde | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | JV Baseball | St. Joseph | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | W 20-5 | |
| Tue., 5/10 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:30 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 5/10 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Co-ed Sailing | Sailing FCSL Team Race Championships @ Indian Harbor YC OR Grass Island | Away - Indian Harbor Yacht Club | TBA | ||
| Tue., 5/10 | V Girls Golf | Danbury | Home - Country Club of Darien [Directions] | 2:50 p.m. | Darien 218 Danbury 282 | |
| Tue., 5/10 | JV Girls Golf | Danbury | Home - Country Club of Darien [Directions] | 2:50 p.m. | ||
| Tue., 5/10 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | L 17-1 | |
| Tue., 5/10 | V Girls Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/10 | JV Girls Tennis | Wilton | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 5/11 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Baseball | Ridgefield | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Boys Lacrosse | Ridgefield | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 5/11 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 5/11 | V Co-ed Sailing | Sailing FCSL Team Race Championships @ Indian Harbor YC OR Grass Island | Away - Indian Harbor Yacht Club | 4:00 p.m. | ||
| Wed., 5/11 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | Darien 239 NC 175 | |
| Wed., 5/11 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Girls Rugby | Trumbull | Home - Royle School Field [Directions] | Postponed | ||
| Wed., 5/11 | V Softball | Ridgefield | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 7-1 | |
| Wed., 5/11 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Wed., 5/11 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Thu., 5/12 | V Baseball | Stamford | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 9-3 | |
| Thu., 5/12 | JV Baseball | Stamford | Home - Darien HS-DHS Baseball - JV Field [Directions] | 3:30 p.m. | ||
| Thu., 5/12 | FR Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | W 16-6 | |
| Thu., 5/12 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | ||
| Thu., 5/12 | FR Boys Lacrosse | Westhill | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 5/12 | V Boys Outdoor Track | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Rugby | Ridgefield | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Fairfield Warde | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Thu., 5/12 | JV Boys Tennis | Fairfield Warde | Home - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 5/12 | JV Boys Volleyball | Fairfield Warde | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/12 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | Darien 214 St. Joseph 218 | |
| Thu., 5/12 | JV Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/12 | V Girls Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | W 20-4 | |
| Thu., 5/12 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 5/12 | V Girls Outdoor Track | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | L 5-4 | |
| Thu., 5/12 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 3:00 p.m. | W 7-0 | |
| Thu., 5/12 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | FR Boys Lacrosse | Staples | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | JV Boys Tennis | Trumbull | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | FR Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | ||
| Sat., 5/14 | FR Boys Lacrosse | Don Bosco (NJ) | Home - Darien HS-DHS Stadium East [Directions] | 10:00 a.m. | ||
| Mon., 5/16 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 5/16 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Girls Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 228 Trumbull 206 | |
| Tue., 5/17 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | W 9-8 | |
| Tue., 5/17 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/17 | FR Boys Lacrosse | Greenwich | Home - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | JV Girls Golf | New Canaan, Wilton | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | New Canaan | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 7:00 p.m. | W 16-1 | |
| Tue., 5/17 | V Girls Tennis | St. Joseph | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/18 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-7 | |
| Wed., 5/18 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | FR Baseball | Fairfield Warde | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Tennis | Ridgefield | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Wed., 5/18 | V Boys Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 5/18 | JV Boys Volleyball | Staples | Home - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Co-ed Sailing | Sailing FCSL Match Race Champs @ Grass Island in Greenwich | Away - Grass Island | 3:30 p.m. | ||
| Wed., 5/18 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | Darien 220 Greenwich 193 | |
| Wed., 5/18 | V Softball | Fairfield Warde | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 8-7 | |
| Thu., 5/19 | V Baseball | Wilton | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 1-2 | |
| Thu., 5/19 | JV Baseball | Wilton | Home - Darien HS-DHS Baseball - JV Field [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | FR Baseball | Staples | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Thu., 5/19 | V Girls Lacrosse | St. Joseph | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Girls Rugby | Staples | Home - Royle School Field [Directions] | 5:00 p.m. | ||
| Thu., 5/19 | V Girls Tennis | New Canaan | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/20 | FR Baseball | Wilton | Away - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Fri., 5/20 | V Boys Outdoor Track | Danbury Dream Invitational @ Darien HS | Away - Danbury HS | 6:30 p.m. | ||
| Fri., 5/20 | V Boys Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/23 | ||||||
| Sat., 5/21 | V Boys Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 12:00 p.m. | ||
| Sat., 5/21 | V Boys Volleyball | Greenwich | Home - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 5/23 | JV Baseball | Staples | Home - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Boys Tennis | Staples | Home - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | Darien 223 Staples 179 | |
| Mon., 5/23 | JV Girls Golf | Staples | Home - Wee Burn CC [Directions] | Canceled | Cancelled | |
| Mon., 5/23 | V Girls Lacrosse | Ridgefield | Home - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | ||
| Mon., 5/23 | V Girls Lacrosse | FCIAC Semi Final 5 or 7p | Away - Norwalk HS-Testa Field, NHS | TBA | ||
| Mon., 5/23 | V Girls Outdoor Track | FCIAC Championships | Away - Wilton HS-Fujitani Field - Turf | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Danbury HS-Wilton HS-Fujitani Field - Turf | ||||||
| Mon., 5/23 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | JV Softball | Westhill (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 5:30 p.m. | ||
| Tue., 5/24 | FR Baseball | Westhill | Home - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | Greenwich | Home - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | FCIAC Championships | Away - Danbury HS-Stadium Track | 3:30 p.m. | ||
| Tue., 5/24 | V Girls Golf | Ridgefield | Home - Country Club of Darien [Directions] | 3:00 p.m. | Darien 236 Ridgefield 244 | |
| Tue., 5/24 | JV Girls Golf | Ridgefield | Home - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 5/24 | V Girls Tennis | Staples | Home - Wilton HS-Staples Tennis Courts [Directions] | 3:00 p.m. | W 4-1 | |
| Wed., 5/25 | V Boys Volleyball | Ridgefield | Home - Fairfield Warde HS-Large Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/25 | JV Girls Golf | Girls JV Golf Ekstrom Tournament | Away - Carl Dickman Par 3 | 3:15 p.m. | ||
| Wed., 5/25 | V Girls Lacrosse | FCIAC Finals | Away - Norwalk HS-Testa Field, NHS | 7:00 p.m. | ||
| Wed., 5/25 | V Softball | Stamford (Scrim.) | Home - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Girls Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | Postponed | ||
| Fri., 5/27 | V Boys Volleyball | Trumbull | Home - Fairfield Warde HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 5/28 | V Boys Lacrosse | Wilton | Away - Brien McMahon HS-Casagrande Field [Directions] | 11:00 a.m. | ||
| Tue., 5/31 | V Boys Tennis | Newington | Home - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/31 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Darien 222 Trumbull 198 | |
| Tue., 5/31 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 5/31 | V Girls Lacrosse | Fairfield Ludlowe | Home - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Tue., 5/31 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Tennis | Conard | Home - Darien HS-DHS Tennis Courts [Directions] | 1:00 p.m. | W 7-0 | |
| Wed., 6/1 | V Boys Lacrosse | Westhill | Home - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | ||
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Boys Tennis | Wilton | Home - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Girls Tennis | Westhill | Home - Darien HS-DHS Tennis Courts [Directions] | 1:00 p.m. | W 4-1 | |
| Thu., 6/2 | V Girls Golf | Girls Golf FCIAC Tournament @ Fairchild Wheeler | Away - Fairchild Wheeler Golf Course | 12:00 p.m. | ||
| Thu., 6/2 | V Girls Tennis | Staples | Home - Solaris Racquet Club [Directions] | 2:00 p.m. | ||
| Fri., 6/3 | V Boys Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:00 p.m. | ||
| Fri., 6/3 | V Boys Volleyball | Newtown | Home - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 6/3 | V Girls Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Sat., 6/4 | V Boys Lacrosse | Greenwich | Home - Darien HS-DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Sat., 6/4 | V Boys Tennis | New Canaan | Away - Wesleyan-John Wood Memorial Tennis Courts [Directions] | 9:00 a.m. | ||
| Sun., 6/5 | V Girls Tennis | Amity | Away - Wesleyan-John Wood Memorial Tennis Courts [Directions] | 11:30 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Golf | CIAC Division I Championship | Away - Tashua Knolls GC | 8:30 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Boys Volleyball | Ridgefield | Home - Fairfield Warde HS-Gym [Directions] | 6:00 p.m. | ||
| Tue., 6/7 | V Girls Lacrosse | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Lacrosse | Fairfield Prep | Home - Fairfield University-Rafferty Stadium [Directions] | 7:30 p.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Volleyball | Trumbull | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Boys Outdoor Track | New England Track and Field Championships @ Willow Brook Park, New Britain CT | Away - [CIAC] Willow Brook Park | 10:00 a.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/11 | V Girls Lacrosse | New Canaan | Home - Sacred Heart University-Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 6/11 | V Girls Outdoor Track | New England Track and Field Championships @ Willow Brook Park, New Britain CT | Away - [CIAC] Willow Brook Park | 10:00 a.m. | ||
| Sun., 6/12 | V Boys Lacrosse | Staples | Home - Sacred Heart University [Directions] | 3:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||