| Darien 2016-17 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1121 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | FR Baseball | Fairfield Ludlowe | Away - Owen Fish Park [Directions] | 4:00 p.m. | @ Owen Fish Park | |
| TBA | FR Baseball | Fairfield Ludlowe | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| TBA | FR Boys Basketball | Newtown | Home - DHS Main Gym [Directions] | TBA | ||
| TBA | JV Boys Golf | Fairfield Prep | Home - Wee Burn CC [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | TBA | @ Milford Ice | |
| TBA | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | ||
| TBA | V Girls Basketball | Holyoke (MA) | Away | Cancelled | Cancelled | |
| TBA | JV Girls Basketball | Holyoke (MA) | Away | 10:30 a.m. | ||
| TBA | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | TBA | ||
| TBA | FR Girls Lacrosse | Greenwich | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Danbury | Away - Hatters Park Softball Fields [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Stamford | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Fairfield Ludlowe | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | St. Joseph | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Wilton | Home - DHS Softball JV Field [Directions] | 4:30 p.m. | ||
| TBA | FR Softball | Danbury | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| TBA | FR Softball | Norwalk | Away - Naramake School [Directions] | TBA | ||
| Sun., 8/28 | V Field Hockey | Staples (Scrim.) | Home - DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Wed., 8/31 | V Boys Soccer | St. Lukes (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Wed., 8/31 | JV Boys Soccer | St. Lukes (Scrim.) | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Wed., 8/31 | V Girls Volleyball | John Jay (NY) (Scrim.) | Away | 3:00 p.m. | ||
| Thu., 9/1 | FR Football | Brien McMahon (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 9/1 | V Girls Soccer | St. Lukes (Scrim.) | Away | 4:00 p.m. | ||
| Fri., 9/2 | V Football | Trinity Catholic (Scrim.) | Home - DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Sat., 9/3 | V Field Hockey | Darien Field Hockey Playday (Wilton, Greenwich Academy, Hotchkiss | Home - DHS Stadium Field [Directions] | 1:00 p.m. | 1:00 - 5:00 p.m. | |
| Sat., 9/3 | V Girls Soccer | PlayDay w/Mahopac, Mercy, Nyack | Home - DHS Turf #2 [Directions] | 10:00 a.m. | Also on DHS Field #1Turf | |
| Sat., 9/3 | V Girls Volleyball | Darien Playday | Home - DHS Main Gym [Directions] | 8:00 a.m. | ||
| Mon., 9/5 | V Boys Soccer | Derby (Scrim.) | Home - DHS Turf #2 [Directions] | 5:00 p.m. | ||
| Tue., 9/6 | V Girls Soccer | Greenwich Academy (Scrim.) | Home - DHS Turf #2 [Directions] | 4:30 p.m. | ||
| Tue., 9/6 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Wed., 9/7 | V Boys Soccer | Bassick (Scrim.) | Away - Went Field [Directions] | 4:00 p.m. | ||
| Wed., 9/7 | V Field Hockey | Greenwich Academy (Scrim.) | Away | 3:30 p.m. | ||
| Wed., 9/7 | JV Field Hockey | Greenwich Academy (Scrim.) | Away | 5:00 p.m. | L 0-3 | |
| Wed., 9/7 | FR Field Hockey | Greenwich Academy (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Fri., 9/9 | FR Football | St. Joseph | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Fri., 9/9 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 5:00 p.m. | L 0-2 | |
| Fri., 9/9 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Fri., 9/9 | FR Boys Soccer | Greenwich | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | L 5-0 | |
| Fri., 9/9 | V Girls Cross Country | Scrimmage in Trumbull | Away | 4:00 p.m. | ||
| Fri., 9/9 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 8-0 | |
| Fri., 9/9 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | W 7-0 | |
| Fri., 9/9 | V Girls Swimming and Diving | St. Joseph | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 9/9 | V Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 6:30 p.m. | W 3-1 | |
| Fri., 9/9 | JV Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 9/10 | V Football | St. Joseph | Away - St. Joseph HS [Directions] | 1:30 p.m. | W 48-14 | |
| Sat., 9/10 | V Girls Soccer | Greenwich | Home - DHS Turf #2 [Directions] | 2:00 p.m. | W 6-1 | |
| Sat., 9/10 | JV Girls Soccer | Greenwich | Home - DHS Field #1 -Turf [Directions] | 2:00 p.m. | L 2-1 | |
| Sat., 9/10 | V Girls Volleyball | Henrick Hudson Tournament | Away | TBA | ||
| Mon., 9/12 | JV Football | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | V Boys Soccer | Trumbull | Home - DHS Turf #2 [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 9/12 | JV Boys Soccer | Trumbull | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Mon., 9/12 | FR Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | L 4-1 | |
| Mon., 9/12 | FR Field Hockey | Trumbull | Away - Indian Ledge Park [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/13 | V Boys Cross Country | Staples, Danbury, Norwalk | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Cross Country | Staples, Danbury, Norwalk | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Field Hockey | Trumbull | Home - DHS Stadium Field [Directions] | 5:30 p.m. | W 7-1 | |
| Tue., 9/13 | JV Field Hockey | Trumbull | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 9/13 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 9/13 | JV Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | L 3-0 | |
| Tue., 9/13 | FR Girls Soccer | Trumbull | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | SO Football | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | ||
| Wed., 9/14 | V Boys Soccer | Brien McMahon | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/14 | JV Boys Soccer | Brien McMahon | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Thu., 9/15 | FR Football | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | ||
| Thu., 9/15 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | W 10-0 | |
| Thu., 9/15 | JV Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:30 p.m. | W 9-0 | |
| Thu., 9/15 | FR Field Hockey | Danbury | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 9/15 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Thu., 9/15 | V Girls Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 9/16 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 9/16 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | FR Boys Soccer | Fairfield Ludlowe | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | T 2-2 | |
| Fri., 9/16 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 9/16 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/16 | FR Girls Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Wilton Invite | Away | 9:30 a.m. | ||
| Sat., 9/17 | V Football | Stamford | Home - DHS Stadium Field [Directions] | 1:30 p.m. | W 51-14 | |
| Sat., 9/17 | V Sideline Cheerleading | Stamford | Home - DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 9/17 | V Girls Cross Country | Wilton Invitational | Away | 9:30 a.m. | ||
| Sat., 9/17 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 12:00 p.m. | W 3-1 | |
| Sat., 9/17 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 10:30 a.m. | W 3-0 | |
| Mon., 9/19 | V Girls Soccer | Fairfield Ludlowe | Home - DHS Turf #2 [Directions] | 4:00 p.m. | T 0-0 | |
| Mon., 9/19 | JV Girls Soccer | Fairfield Ludlowe | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Mon., 9/19 | V Girls Volleyball | Trumbull | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 9/19 | JV Girls Volleyball | Trumbull | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 9/19 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Ridgefield, Brien McMahon, St. Joseph | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | JV Football | Stamford | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 9/20 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | FR Boys Soccer | New Canaan | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/20 | V Girls Cross Country | Ridgefield, Brien McMahon, St. Joseph | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Field Hockey | Greenwich | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 8-1 | |
| Wed., 9/21 | JV Field Hockey | Greenwich | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 9/21 | V Girls Soccer | New Canaan | Home - DHS Turf #2 [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 9/21 | JV Girls Soccer | New Canaan | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Wed., 9/21 | FR Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | JV Girls Swimming and Diving | Greenwich | Home - Darien YMCA [Directions] | 3:00 p.m. | 2:30 p.m. warm-up | |
| Wed., 9/21 | V Girls Volleyball | Brien McMahon | Home - DHS Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 9/21 | JV Girls Volleyball | Brien McMahon | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/22 | FR Football | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Danbury | Home - DHS Turf #2 [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 9/22 | JV Boys Soccer | Danbury | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/23 | V Field Hockey | New Canaan | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/23 | JV Field Hockey | New Canaan | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | FR Field Hockey | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | T 0-0 | |
| Fri., 9/23 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 6:00 p.m. | ||
| Fri., 9/23 | FR Girls Soccer | Danbury | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 9/23 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | FR Girls Volleyball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | V Football | Greenwich | Home - DHS Stadium Field [Directions] | 1:30 p.m. | W 42-35 | HOMECOMING |
| Sat., 9/24 | V Sideline Cheerleading | Greenwich | Home - DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 9/24 | V Girls Cross Country | Ocean State Invite @ Goddard Park, RI | Away | 1:35 p.m. | ||
| Sat., 9/24 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | JV Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 10:30 a.m. | 10:00 a.m. warm-up | |
| Mon., 9/26 | JV Football | Greenwich | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/26 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | T 1-1 | |
| Mon., 9/26 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 9/26 | FR Boys Soccer | Stamford | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 9/26 | FR Field Hockey | Greenwich Academy | Away | 4:30 p.m. | ||
| Mon., 9/26 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/26 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 9/26 | FR Girls Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Cross Country | Wilton, Westhill | Away - Allen's Field [Directions] | 4:00 p.m. | BRIDGEPORT CENTRAL CANCELLED | |
| Tue., 9/27 | FR Boys Soccer | Norwalk | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/27 | V Girls Cross Country | Wilton, Westhill | Away - Allen's Field [Directions] | 4:00 p.m. | BRIDGEPORT CENTRAL CANCELLED | |
| Tue., 9/27 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 9/27 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Stamford | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 9/27 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | SO Football | New Canaan | Home - DHS Stadium East Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 9/28 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:15 p.m. | W 2-1 | |
| Wed., 9/28 | JV Boys Soccer | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | FR Field Hockey | Westhill | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/28 | JV Girls Volleyball | Danbury | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Field Hockey | Norwalk | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 9/29 | JV Field Hockey | Norwalk | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 9/29 | FR Field Hockey | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Girls Soccer | Norwalk | Home - DHS Turf #2 [Directions] | 4:15 p.m. | W 4-0 | |
| Thu., 9/29 | JV Girls Soccer | Norwalk | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | FR Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Boys Soccer | Fairfield Warde | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 9/30 | JV Boys Soccer | Fairfield Warde | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Fri., 9/30 | V Girls Swimming and Diving | Fairfield Warde | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 9/30 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 9/30 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 9/30 | FR Girls Volleyball | Stamford | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | Norwich Free Academy | Home - DHS Stadium Field [Directions] | 2:00 p.m. | W 45-6 | |
| Sat., 10/1 | V Sideline Cheerleading | Norwich Free Academy | Home - DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Tue., 10/4 | V Boys Cross Country | Greenwich, Fairfield Warde, New Canaan, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | JV Football | Trumbull (Scrim.) | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Cross Country | Greenwich, Fairfield Warde, New Canaan, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 10/4 | JV Field Hockey | Wilton | Away [Directions] | 5:30 p.m. | ||
| Tue., 10/4 | FR Field Hockey | Wilton | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | T 0-0 | |
| Tue., 10/4 | FR Girls Soccer | Fairfield Warde | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Wed., 10/5 | V Boys Soccer | Ridgefield | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/5 | JV Boys Soccer | Ridgefield | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Wed., 10/5 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/5 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/5 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/5 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | FR Football | Newtown | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Field Hockey | Ridgefield | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 4-0 | |
| Thu., 10/6 | JV Field Hockey | Ridgefield | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 1-0 | |
| Thu., 10/6 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | FR Girls Soccer | Ridgefield | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/7 | JV Girls Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 10/7 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/8 | V Boys Cross Country | Wickham Park Invite, Manchester, CT | Away | TBA | ||
| Sat., 10/8 | SO Football | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | V Field Hockey | Lakeland/Panas (NY) | Home - DHS Stadium Field [Directions] | 1:00 p.m. | T 0-0 | |
| Sat., 10/8 | JV Field Hockey | Lakeland/Panas (NY) | Home - DHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 10/8 | JV Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 11:00 a.m. | 10:00 a.m. warm-up | |
| Mon., 10/10 | V Boys Cross Country | Fairfield Ludlowe, Trumbull, Stamford | Away - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 10/10 | JV Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | FR Boys Soccer | Wilton | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | W 7-2 | |
| Mon., 10/10 | V Girls Cross Country | Fairfield Ludlowe, Trumbull, Stamford | Away - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | V Field Hockey | Daniel Hand | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/10 | JV Field Hockey | Daniel Hand | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 10/10 | V Girls Swimming and Diving | Staples | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Mon., 10/10 | V Girls Volleyball | Newtown | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 2-3 | |
| Mon., 10/10 | JV Girls Volleyball | Newtown | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/10 | FR Girls Volleyball | Newtown | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Wilton | Home - DHS Turf #2 [Directions] | 4:00 p.m. | L 1-2 | |
| Tue., 10/11 | JV Girls Soccer | Wilton | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | FR Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Girls Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 3:30 p.m. | L 0-3 | |
| Tue., 10/11 | JV Girls Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Staples | Home - DHS Turf #2 [Directions] | 4:00 p.m. | T 0-0 | |
| Thu., 10/13 | JV Boys Soccer | Staples | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | FR Boys Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 3-0 | |
| Thu., 10/13 | V Field Hockey | Staples | Home - DHS Stadium Field [Directions] | 4:00 p.m. | T 1-1 | |
| Thu., 10/13 | JV Field Hockey | Staples | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 10/13 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 7:15 p.m. | Warm-up @ 6:45 p.m. | |
| Fri., 10/14 | FR Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | ||
| Fri., 10/14 | FR Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:30 p.m. | L 4-2 | |
| Fri., 10/14 | JV Girls Soccer | Stamford | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Sat., 10/15 | V Football | Brien McMahon | Home - DHS Stadium Field [Directions] | 1:30 p.m. | W 54-17 | |
| Sat., 10/15 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 5-0 | |
| Sat., 10/15 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | ||
| Sat., 10/15 | FR Boys Soccer | Greenwich Country Day | Away | Cancelled | Cancelled | |
| Sat., 10/15 | V Sideline Cheerleading | Brien McMahon | Home - DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 10/15 | FR Field Hockey | Greenwich Country Day | Away | 12:30 p.m. | ||
| Sat., 10/15 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 2-0 | |
| Sat., 10/15 | JV Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:15 p.m. | ||
| Sat., 10/15 | V Girls Volleyball | Rhode Island Invitational | Away | 9:00 a.m. | ||
| Mon., 10/17 | FR Field Hockey | Staples | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Girls Soccer | St. Joseph | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/17 | JV Girls Soccer | St. Joseph | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 10/17 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | Wilton | Home - DHS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | V Boys Soccer | Westhill | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/18 | JV Boys Soccer | Westhill | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | FR Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 3:30 p.m. | T 4-4 | |
| Tue., 10/18 | V Field Hockey | Brien McMahon | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 10/18 | JV Field Hockey | Brien McMahon | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 10/18 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/19 | V Boys Cross Country | FCIACS @ Waveny Park, New Canaan | Away | 2:15 p.m. | ||
| Wed., 10/19 | SO Football | Brien McMahon | Home - DHS Stadium East Turf Field [Directions] | Cancelled | Cancelled | |
| Wed., 10/19 | V Girls Cross Country | FCIACS @ Waveny Park, New Canaan | Away | 2:15 p.m. | ||
| Wed., 10/19 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 10/19 | JV Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Wed., 10/19 | FR Field Hockey | Fairfield Ludlowe | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/19 | FR Girls Soccer | Ridgefield | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Staples | Home - DHS Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/19 | JV Girls Volleyball | Staples | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/19 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/20 | FR Football | Danbury | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Trinity Catholic | Away - Gaglio Field | 4:00 p.m. | W 7-0 | |
| Thu., 10/20 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 6:00 p.m. | Warm-up @ 5:30 p.m. | |
| Fri., 10/21 | V Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 7:00 p.m. | W 41-16 | |
| Fri., 10/21 | V Sideline Cheerleading | Danbury | Away [Directions] | 7:00 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Trinity Catholic | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 10/21 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 10/21 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Fri., 10/21 | FR Girls Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | JV Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 10/24 | V Boys Soccer | Bridgeport Central | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 5-3 | |
| Mon., 10/24 | JV Boys Soccer | Bridgeport Central | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | JV Field Hockey | Greenwich Academy | Away | 3:30 p.m. | ||
| Mon., 10/24 | JV Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Westhill | Home - DHS Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 10/24 | JV Girls Volleyball | Westhill | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | FR Field Hockey | Greenwich Academy | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 10/25 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 10/26 | SO Football | Greenwich (Scrim.) | Home - DHS Stadium East Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 10/26 | FR Football | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Wed., 10/26 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | W 1-0(OT) | |
| Wed., 10/26 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Wed., 10/26 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | FR Girls Soccer | Staples | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | W 3-0 | |
| Wed., 10/26 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Thu., 10/27 | V Boys Soccer | FCIAC Quarterfinals vs Fairfield Warde | Away - DHS Turf #2 | 3:30 p.m. | ||
| Thu., 10/27 | V Girls Cross Country | Freshmen's Two Mile Race @ Danbury | Away | 3:45 p.m. | Freshmen Only | |
| Thu., 10/27 | V Girls Volleyball | Bridgeport Central | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 10/27 | JV Girls Volleyball | Bridgeport Central | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/28 | V Field Hockey | FCIAC Quarterfinals vs Greenwich | Home - DHS Stadium Field [Directions] | 4:00 p.m. | 10/29 Rain date/field conflict | |
| Fri., 10/28 | V Girls Soccer | FCIAC Quarterfinals @ Staples | Away | 3:30 p.m. | 10/29 RAIN DATE OR FIELD CONFLICT | |
| Fri., 10/28 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class L @ Wickham Park, Manchester, CT | Away | 2:05 p.m. | ||
| Sat., 10/29 | V Football | Wilton | Home - DHS Stadium Field [Directions] | 1:00 p.m. | W 35-3 | |
| Sat., 10/29 | V Sideline Cheerleading | Wilton | Home - DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class L Meet @ Wickham Park | Away | TBA | Best Seven Runners | |
| Sat., 10/29 | JV Girls Swimming and Diving | FCIAC JV Swimming @ Greenwich | Away | 4:00 p.m. | Warm-Up at 3:00 p.m. | |
| Sat., 10/29 | FR Girls Volleyball | Southington | Away [Directions] | 9:00 a.m. | ||
| Mon., 10/31 | JV Football | Wilton | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | V Boys Soccer | Tentative FCIAC Semi-Finals @ Fairfield Ludlowe | Away | Cancelled | Cancelled | Games at 5:00 p.m. & 7:00 p.m. |
| Tue., 11/1 | V Field Hockey | FCIAC Semi-Finals vs Staples @ Brien McMahon | Away | 7:30 p.m. | Games @ 6:00 p.m. and 7:30 p.m. | |
| Tue., 11/1 | FR Field Hockey | Greenwich Country Day | Home - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Tue., 11/1 | V Girls Soccer | Tentative FCIAC Semi-Finals @ Wilton | Away | Cancelled | Cancelled | 5:00 p.m. or 7:00 p.m. |
| Tue., 11/1 | V Girls Swimming and Diving | FCIAC Swimming Trials @ Greenwich | Away | 4:30 p.m. | Warm-Ups at 3:00 p.m. | |
| Tue., 11/1 | V Girls Volleyball | FCIAC Quarterfinals @ Greenwich | Away - DHS Main Gym | 4:00 p.m. | ||
| Wed., 11/2 | V Boys Soccer | Ridgefield (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Wed., 11/2 | JV Boys Soccer | Ridgefield (Scrim.) | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | Varsity scrimmage | |
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving @ Westhill | Away | 4:30 p.m. | Warm-Ups @ 2:30 p.m. | |
| Thu., 11/3 | FR Football | Fairfield Warde | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 11/3 | V Boys Soccer | Tentative FCIAC Final @ Norwalk | Away | Cancelled | Cancelled | |
| Thu., 11/3 | V Field Hockey | Tentative FCIAC Final @ Brien McMahon | Away | Cancelled | Cancelled | |
| Thu., 11/3 | V Girls Soccer | Tentative FCIAC Finals @ Norwalk | Away | Cancelled | Cancelled | |
| Thu., 11/3 | V Girls Swimming and Diving | FCIAC Swimming Finals @ Greenwich | Away | 6:30 p.m. | Warm-Ups at 5:00 p.m. | |
| Thu., 11/3 | V Girls Volleyball | Tentative FCIAC Semi-Finals @ Fairfield Ludllowe | Away | Cancelled | Cancelled | 5:00 p.m. or 7:00 p.m. |
| Fri., 11/4 | V Boys Cross Country | State Open @ Wickham Park, Manchester, CT | Away | 2:00 p.m. | ||
| Fri., 11/4 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | W 50-21 | |
| Fri., 11/4 | V Sideline Cheerleading | Fairfield Warde | Away [Directions] | 7:00 p.m. | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open @ Wickham Park | Away | TBA | Need to Qualify | |
| Sat., 11/5 | JV Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 10:00 a.m. | ||
| Sat., 11/5 | V Girls Volleyball | Tentative FCIAC Final @ Fairfield Ludlowe | Away | Cancelled | Cancelled | |
| Mon., 11/7 | V Field Hockey | King and Low-Heywood Thomas (Scrim.) | Home - DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Mon., 11/7 | V Girls Soccer | CIAC Class LL - Round 1 vs Danbury | Home - DHS Turf #2 [Directions] | Cancelled | Cancelled | |
| Mon., 11/7 | V Girls Volleyball | CIAC Class LL - Round 1 @ Trumbull | Away | 3:00 p.m. | ||
| Tue., 11/8 | V Boys Soccer | CIAC Class LL - Round 1 vs Conard | Home - DHS Turf #2 [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Field Hockey | CIAC Class L - Round 1 vs Amity | Home - DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Girls Soccer | CIAC Class L - Round 1 vs Trumbull | Home - DHS Turf #2 [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Girls Swimming and Diving | Class L Diving Championship @ Middletown | Away | 5:30 p.m. | Warm-Ups @ 4:00 p.m. | |
| Thu., 11/10 | SO Football | Staples | Away - @ Staples [Directions] | 5:30 p.m. | ||
| Thu., 11/10 | FR Football | Staples | Home - DHS Stadium East Turf Field [Directions] | 3:00 p.m. | ||
| Thu., 11/10 | V Boys Soccer | CIAC Class LL - Round 2 @ Farmington's Tunxis Meade | Away | 2:00 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | Tentative CIAC Class LL - Round 2 | Away | Cancelled | Cancelled | |
| Fri., 11/11 | V Football | Staples | Away - Staples Stadium [Directions] | 7:00 p.m. | W 27-0 | |
| Fri., 11/11 | V Sideline Cheerleading | Staples | Away [Directions] | 7:00 p.m. | ||
| Fri., 11/11 | V Field Hockey | CIAC Class L - Quarterfinals vs Cheshire | Home - DHS Stadium Field [Directions] | 2:00 p.m. | Alt date 11/12 | |
| Fri., 11/11 | V Girls Soccer | Tentative CIAC Class L - Round 2 @ E. Hartford/Ridgefield winner | Away | Cancelled | Cancelled | |
| Sat., 11/12 | V Boys Cross Country | New Englands @ Ponaganset HS/North Scituate, RI | Away | TBA | ||
| Sat., 11/12 | V Boys Soccer | Tentative CIAC Class LL - Quarterfinals | Away | 2:00 p.m. | ||
| Sat., 11/12 | V Girls Cross Country | New England Meet in Rhode Island | Away | TBA | Need to Qualify | |
| Sat., 11/12 | V Girls Swimming and Diving | Class L Swimming Trials @ East Hartford | Away | 11:30 a.m. | Warm-Ups @ 10:00 a.m. | |
| Sat., 11/12 | V Girls Volleyball | Tentative CIAC Class LL - Quarterfinals | Away | Cancelled | Cancelled | |
| Sun., 11/13 | V Girls Soccer | Tentative CIAC Class LL - Quarterfinals | Away | Cancelled | Cancelled | |
| Mon., 11/14 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Tue., 11/15 | V Boys Soccer | Tentative CIAC Class LL - Semifinals | Away | Cancelled | Cancelled | Alt date 11/16 |
| Tue., 11/15 | V Girls Soccer | Tentative CIAC Class LL - Semi-Finals | Away | Cancelled | Cancelled | |
| Tue., 11/15 | V Girls Swimming and Diving | Class L Finals Championship @ Southern CT | Away | 6:00 p.m. | Warm-Ups @ 5:00 p.m. | |
| Wed., 11/16 | V Field Hockey | CIAC Class L - Semifinals vs Glastonbury @ Watertown HS | Away | 6:00 p.m. | ||
| Wed., 11/16 | V Girls Volleyball | Tentative CIAC Class LL - Semifinals | Away | Cancelled | Cancelled | |
| Thu., 11/17 | SO Football | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 11/17 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 6:00 p.m. | ||
| Fri., 11/18 | V Boys Soccer | Tentative CIAC Class LL - Final | Away | Cancelled | Cancelled | Alt date 11/19 |
| Fri., 11/18 | V Girls Swimming and Diving | State Open Diving Championship @ Bulkeley HS, Hartford, CT | Away | 5:30 p.m. | Warm-Ups at 4:00 p.m. | |
| Sat., 11/19 | V Field Hockey | CIAC Class L - Final vs Staples @ Wethersfield HS Field Turf Complex | Away | 10:00 a.m. | ||
| Sat., 11/19 | V Girls Soccer | Tentative CIAC Finals | Away | Cancelled | Cancelled | Alt date 11/19 |
| Sat., 11/19 | V Girls Swimming and Diving | State Open Swimming Championship @ Yale | Away | 12:00 p.m. | Warm-Ups @ 10:00 a.m. | |
| Sat., 11/19 | V Girls Volleyball | Tentative CIAC Class LL - Final @ East Haven HS | Away | Cancelled | Cancelled | |
| Thu., 11/24 | V Football | New Canaan | Away - Dunning Stadium [Directions] | 10:30 a.m. | W 37-34 (OT) | |
| Thu., 11/24 | V Sideline Cheerleading | New Canaan | Away [Directions] | 10:30 a.m. | ||
| Sat., 11/26 | V Boys Cross Country | Foot Locker Northeast @ Van Cortlandt Park, Bronx, NY | Away | Cancelled | Cancelled | |
| Sat., 11/26 | V Girls Ice Hockey | Alumnae Game | Home - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Tue., 11/29 | V Football | CIAC Quarterfinal vs Greenwich @ Boyle Stadium | Home [Directions] | 6:30 p.m. | ||
| Sat., 12/3 | V Boys Squash | @ Poly Prep, Brooklyn, NY | Away | 8:30 a.m. | ||
| Sat., 12/3 | V Girls Ice Hockey | Shelton Jamboree @ Rinks @ Shelton | Away | 6:00 p.m. | ||
| Sun., 12/4 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away [Directions] | 12:30 p.m. | ||
| Sun., 12/4 | JV Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away [Directions] | TBA | ||
| Mon., 12/5 | V Football | CIAC Semifinal vs Southington @ Boyle Stadium, Stamford | Home [Directions] | 6:30 p.m. | ||
| Mon., 12/5 | V Boys Squash | @ Hackley, Tarrytown, NY | Away | 4:00 p.m. | ||
| Mon., 12/5 | V Girls Squash | New Canaan | Home - Chelsea Piers [Directions] | 8:30 p.m. | ||
| Wed., 12/7 | V Boys Squash | Rye (NY) | Home - Royle School Field [Directions] | 7:00 p.m. | ||
| Wed., 12/7 | JV Boys Squash | Fairfield | Home - Chelsea Piers [Directions] | 8:00 p.m. | ||
| Wed., 12/7 | V Girls Basketball | Fairfield Ludlowe (Scrim.) | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/7 | JV Girls Basketball | Fairfield Ludlowe (Scrim.) | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/7 | V Girls Ice Hockey | Hamden Coop | Home - Darien Ice Rink [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 12/9 | V Girls Basketball | Weston (Scrim.) | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/9 | JV Girls Basketball | Weston (Scrim.) | Home - DHS Main Gym [Directions] | TBA | ||
| Sat., 12/10 | V Boys Basketball | Hoops for Food Jamboree @ Windsor HS | Away | 1:30 p.m. | ||
| Sat., 12/10 | V Football | CIAC Final vs Ridgefield @ West Haven | Away | 2:30 p.m. | ||
| Sat., 12/10 | V Boys Ice Hockey | St. John's Prep @ Sono | Away | 11:00 a.m. | ||
| Sat., 12/10 | V Girls Ice Hockey | Simsbury | Home - Darien Ice Rink [Directions] | 6:10 p.m. | L 1-2 | |
| Mon., 12/12 | V Boys Squash | Brunswick School | Away | 4:00 p.m. | ||
| Mon., 12/12 | V Girls Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 5:15 p.m. | W 40-29 | Non-League |
| Mon., 12/12 | JV Girls Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Mon., 12/12 | V Girls Squash | Westport | Home - Chelsea Piers [Directions] | 8:30 p.m. | ||
| Wed., 12/14 | V Boys Basketball | Immaculate (Scrim.) | Away - Immaculate HS [Directions] | 6:15 p.m. | ||
| Wed., 12/14 | V Boys Squash | Harrison (NY) | Home - Royle School Field [Directions] | 7:00 p.m. | ||
| Wed., 12/14 | V Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 5:15 p.m. | W 57-24 | Non-League |
| Wed., 12/14 | JV Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 12/14 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Connors Rink [Directions] | 5:10 p.m. | L 0-2 | |
| Thu., 12/15 | V Wrestling | Fairfield Warde | Away - Fairfield Warde Small Gym [Directions] | 5:00 p.m. | ||
| Sat., 12/17 | V Boys Basketball | Trumbull | Away - Staples H.S. [Directions] | 5:00 p.m. | L 55-63 | Game @ Staples HS- non-league |
| Sat., 12/17 | V Boys Ice Hockey | Hamden | Home - Darien Ice Rink [Directions] | 6:00 p.m. | L 2-7 | |
| Sat., 12/17 | V Boys Indoor Track | Qualifying Meet @ Staples v Greenwich, Warde, Ludlowe, Stamford, Central, St Joes, Staples | Away | 1:00 p.m. | ||
| Sat., 12/17 | V Boys Swimming and Diving | Norwalk HS Relays | Away | 3:00 p.m. | Warmups @ 2:00 p.m. | |
| Sat., 12/17 | V Wrestling | Derby Invitational | Away | Cancelled | Cancelled | Weigh in @ 11:00 a.m. |
| Sat., 12/17 | V Girls Indoor Track | Qualifying Meet @ Staples v Greenwich, Warde, Ludlowe, Stamford, Central, St Joes, Staples | Away | 1:00 p.m. | ||
| Mon., 12/19 | V Boys Basketball | Staples | Away - Trumbull H.S. [Directions] | 5:30 p.m. | W 71-64 | @ Trumbull HS- non-league |
| Mon., 12/19 | V Girls Squash | Rye 1 | Home - Chelsea Piers [Directions] | 8:30 p.m. | ||
| Tue., 12/20 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena [Directions] | 8:20 p.m. | ||
| Tue., 12/20 | V Wrestling | Norwalk | Home - DHS - South Gym [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Norwalk | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 46-56 | |
| Tue., 12/20 | JV Girls Basketball | Norwalk | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice Rink [Directions] | 5:50 p.m. | L 2-3 (OT) | |
| Wed., 12/21 | V Boys Squash | Bronxville (NY) | Home - Royle School Field [Directions] | 7:00 p.m. | ||
| Wed., 12/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 4:00 p.m. | W 9-1 | |
| Thu., 12/22 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | L 61-58 | |
| Thu., 12/22 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/22 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 12/22 | JV Boys Ice Hockey | Greenwich | Home - Stamford Twin Rinks [Directions] | 4:00 p.m. | ||
| Thu., 12/22 | V Wrestling | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 4:00 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 44-59 | |
| Thu., 12/22 | JV Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/23 | JV Boys Ice Hockey | New Canaan | Away - Sono Veterns Park [Directions] | 3:30 p.m. | @ Sono Veterans Park | |
| Mon., 12/26 | JV Boys Ice Hockey | St. Joseph | Away [Directions] | 2:45 p.m. | Game will be played at Milford Ice | |
| Mon., 12/26 | V Boys Indoor Track | North Shore HS Invitational | Away | TBA | ||
| Mon., 12/26 | V Girls Indoor Track | North Shore HS Invitational at Armory Track and Field Center | Away | TBA | ||
| Tue., 12/27 | V Boys Basketball | Norwich Free Academy | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 48-65 | |
| Tue., 12/27 | JV Boys Basketball | Norwich Free Academy | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 12/27 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 4:00 p.m. | L 2-5 | Non-League |
| Wed., 12/28 | JV Boys Ice Hockey | Trumbull | Away [Directions] | 1:00 p.m. | @ Milford Ice | |
| Thu., 12/29 | V Boys Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | 6:00 p.m. | W 4-3 | Non-League |
| Thu., 12/29 | JV Boys Ice Hockey | Cheshire | Away [Directions] | 2:45 p.m. | Game will be played at Milford Ice | |
| Thu., 12/29 | V Wrestling | Staples, Ridgefield, Westhill | Away - Staples Field House [Directions] | 12:00 p.m. | ||
| Tue., 1/3 | V Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 66-53 | |
| Tue., 1/3 | JV Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 47-58 | |
| Tue., 1/3 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 1/4 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | 4:00 p.m. | L 3-6 | |
| Wed., 1/4 | JV Boys Squash | Westport | Home - Chelsea Piers [Directions] | 9:00 p.m. | ||
| Wed., 1/4 | V Boys Swimming and Diving | Ridgefield | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/4 | V Wrestling | Stamford | Home - DHS - South Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | ||
| Thu., 1/5 | FR Boys Basketball | Harding | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 85-39 | |
| Fri., 1/6 | JV Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:45 p.m. | W 57-33 | |
| Fri., 1/6 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Indoor Track | Qualifying Meet @ Wilton v Greenwich, Danbury, New Canaan, McMahon, Central, St Joes & Wilton | Away | 9:30 a.m. | ||
| Sat., 1/7 | V Wrestling | Bethel, Seymour, Amity | Home - DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | Qualifying Meet @ Wilton v Greenwich, Danbury, New Canaan, McMahon, Central, St Joes & Wilton | Away | 9:30 a.m. | ||
| Sun., 1/8 | JV Boys Ice Hockey | Notre Dame-West Haven (Scrim.) | Home - SONO Ice House [Directions] | 1:30 p.m. | ||
| Tue., 1/10 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | W 66-59 | |
| Tue., 1/10 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Trinity Catholic | Home - DHS Main Gym [Directions] | 5:30 p.m. | W 50-28 | |
| Tue., 1/10 | JV Girls Basketball | Trinity Catholic | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | 6:30 p.m. | DHS: 124.95 FLHS: 130.8 FWHS: 110.85 | @ GCA |
| Wed., 1/11 | V Boys Ice Hockey | Xavier | Home - Darien Ice Rink [Directions] | 6:00 p.m. | L 3-4(OT) | |
| Wed., 1/11 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | 4:15 p.m. | @ Wonderland of Ice | |
| Wed., 1/11 | V Boys Squash | Taft/Choate @ Taft | Away | 3:30 p.m. | ||
| Wed., 1/11 | JV Boys Squash | Rye (NY) | Home - Chelsea Piers [Directions] | 9:00 p.m. | ||
| Wed., 1/11 | V Boys Swimming and Diving | Trumbull | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/11 | V Wrestling | Wilton | Home - DHS - South Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 5:30 p.m. | W 9-3 | |
| Thu., 1/12 | V Boys Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 55-43 | |
| Thu., 1/12 | JV Boys Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/12 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | ||
| Thu., 1/12 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | W 59-43 | |
| Thu., 1/12 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Thu., 1/12 | V Girls Ice Hockey | Morristown-Beard (NJ) | Away | 4:00 p.m. | W 1-0 | |
| Fri., 1/13 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 1/13 | V Girls Squash | Rye II @ Lifetime | Away | 4:00 p.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | 1:00 p.m. | W 5-0 | |
| Sat., 1/14 | V Boys Indoor Track | Qualifying Meet @ Wilton v Warde,New Canaan, Trumbull, Ludlowe, Norwalk, Stamford & Wilton | Away | 9:30 a.m. | ||
| Sat., 1/14 | V Boys Indoor Track | Stanner Games @ Armory, NYC | Away | TBA | ||
| Sat., 1/14 | V Wrestling | Bunnell, New Canaan, Stamford, Norwalk | Home - DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice Rink [Directions] | 7:00 p.m. | W 9-1 | |
| Sat., 1/14 | V Girls Indoor Track | Qualifying Meet @ Wilton v Warde,New Canaan, Trumbull, Ludlowe, Norwalk, Stamford & Wilton | Away | 9:30 a.m. | ||
| Sat., 1/14 | V Girls Indoor Track | Stanner Games @ Armory, NYC | Away | TBA | ||
| Mon., 1/16 | V Girls Ice Hockey | New Canaan | Home - Darien Ice Rink [Directions] | 6:40 p.m. | W 6-0 | |
| Tue., 1/17 | V Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 48-41 | |
| Tue., 1/17 | JV Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | L 42-50 | |
| Tue., 1/17 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | Norwalk | Home - Darien Ice Rink [Directions] | 8:10 p.m. | W 8-1 | |
| Wed., 1/18 | V Boys Swimming and Diving | Greenwich | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/18 | V Wrestling | Mahopac (NY) | Away | 5:00 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | W 55-53 | |
| Fri., 1/20 | JV Boys Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Stamford | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 37-61 | |
| Fri., 1/20 | JV Girls Basketball | Stamford | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | 5:20 p.m. | W 3-2(OT) | |
| Sat., 1/21 | V Boys Indoor Track | Qualifying Meet @ Staples v Warde, New Canaan, Trumbull, Ludlowe, Norwalk, McMahon & Staples | Away | 10:00 a.m. | ||
| Sat., 1/21 | V Boys Indoor Track | Yale Track Classic | Away | 7:35 a.m. | ||
| Sat., 1/21 | V Boys Indoor Track | SCC Coaches Invitational @ Hillhouse HS | Away | 9:00 a.m. | ||
| Sat., 1/21 | V Boys Squash | Brunswick School | Away | 3:00 p.m. | ||
| Sat., 1/21 | V Wrestling | Guilford Duals | Away | 10:00 a.m. | ||
| Sat., 1/21 | V Girls Gymnastics | Greenwich | Home - Darien YMCA [Directions] | 2:00 p.m. | DHS: 130.9 GHS: 140.15 | |
| Sat., 1/21 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | 3:20 p.m. | W 7-0 | |
| Sat., 1/21 | V Girls Indoor Track | Qualifying Meet @ Staples v Warde, New Canaan, Trumbull, Ludlowe, Norwalk, McMahon & Staples | Away | 10:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | SCC Coaches Invitational @ Hillhouse HS | Away | 3:00 p.m. | ||
| Mon., 1/23 | V Girls Gymnastics | Pomperaug Invitational | Away | Cancelled | Cancelled | |
| Tue., 1/24 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 56-59 | |
| Tue., 1/24 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | JV Boys Ice Hockey | Fairfield Prep | Home - Darien Ice Rink [Directions] | 2:50 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Wilton | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 36-47 | |
| Tue., 1/24 | JV Girls Basketball | Wilton | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Gymnastics | Westhill, New Canaan, Fairfield Ludlowe, Fairfield Warde | Away - Westhill - New Gymnasium [Directions] | 5:30 p.m. | DHS: 128.35 Westhill HS 95.5 Stamford HS 63.75 New Canaan 117.15 | @ Westhill HS |
| Wed., 1/25 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice Rink [Directions] | 7:00 p.m. | L 1-2 | |
| Wed., 1/25 | V Boys Squash | New Canaan | Home - Royle School Field [Directions] | 8:00 p.m. | ||
| Wed., 1/25 | JV Boys Squash | vs New Canaan Day School at CC of New Canaan | Away | 3:30 p.m. | ||
| Wed., 1/25 | JV Boys Squash | New Canaan | Home - Chelsea Piers [Directions] | 9:00 p.m. | ||
| Wed., 1/25 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/25 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | ||
| Wed., 1/25 | V Girls Basketball | Harding | Home - DHS Main Gym [Directions] | 5:00 p.m. | W 64-40 | |
| Wed., 1/25 | JV Girls Basketball | Harding | Home - DHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/25 | V Girls Ice Hockey | Hall/Conard | Home - Darien Ice Rink [Directions] | 4:20 p.m. | W 2-0 | |
| Fri., 1/27 | V Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 53-56 | |
| Fri., 1/27 | JV Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Boys Squash | Fairwest Championships 1/27 thru 1/29/17 | Away | TBA | ||
| Fri., 1/27 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 39-57 | |
| Fri., 1/27 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | V Girls Squash | StreetSquash | Home - Chelsea Piers [Directions] | TBA | ||
| Sat., 1/28 | V Boys Ice Hockey | Trumbull | Home - Darien Ice Rink [Directions] | 5:00 p.m. | W 6-4 | |
| Sat., 1/28 | V Boys Indoor Track | East Division Championship @ Wilton | Away | 9:30 a.m. | ||
| Sat., 1/28 | V Wrestling | Portland Invitational | Away | 9:00 a.m. | @ Portland HS | |
| Sat., 1/28 | V Girls Gymnastics | Trumbull, Staples | Away - Next Dimension Gymnastics [Directions] | 6:00 p.m. | DHS: 129.05 Trumbull HS: 140.15 Staples: 121.05 | @ Next Dimensions- Trumbull |
| Sat., 1/28 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice Rink [Directions] | 7:10 p.m. | W 8-0 | |
| Sat., 1/28 | V Girls Indoor Track | East Division Championship @ Wilton | Away | 9:30 a.m. | ||
| Sat., 1/28 | V Girls Squash | Fairwest Championship | Away | 10:00 a.m. | 10:00 a.m. - 4:00 p.m. | |
| Sun., 1/29 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 9:00 p.m. | ||
| Sun., 1/29 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice Rink [Directions] | 7:30 p.m. | W 2-1 | |
| Mon., 1/30 | FR Boys Basketball | Greenwich Country Day | Away | 4:15 p.m. | ||
| Mon., 1/30 | V Boys Squash | Hopkins School | Away | 3:30 p.m. | New Haven | |
| Mon., 1/30 | V Co-ed Alpine Skiing | Shootouts @ Mt. Southington | Away | 4:00 p.m. | ||
| Wed., 2/1 | V Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 64-56 | |
| Wed., 2/1 | JV Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/1 | FR Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/1 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 8:30 p.m. | L 0-4 | |
| Wed., 2/1 | V Wrestling | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/1 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | ||
| Wed., 2/1 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 44-58 | |
| Wed., 2/1 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/1 | V Girls Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | 7:20 p.m. | W 3-1 | |
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championshp @ Hillhouse | Away | 4:30 p.m.k | ||
| Thu., 2/2 | V Girls Indoor Track | FCIAC Championshp @ Hillhouse | Away | 4:30 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | L 44-50 | |
| Fri., 2/3 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 5:30 p.m. | W 61-39 | |
| Fri., 2/3 | JV Girls Basketball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | New Canaan | Home - Darien Ice Rink [Directions] | 4:00 p.m. | L 1-4 | |
| Sat., 2/4 | JV Boys Ice Hockey | Norwalk | Home - Terry Connors Rink [Directions] | Cancelled | Cancelled | |
| Sat., 2/4 | V Boys Indoor Track | JV FCIACS @ Staples HS | Away | 10:00 a.m. | ||
| Sat., 2/4 | V Wrestling | Lawmen Invitational | Away | 10:00 a.m. | ||
| Sat., 2/4 | V Girls Gymnastics | Wilton, Trumbull | Home - Darien YMCA [Directions] | 2:00 p.m. | DHS: 132.1 Wilton: 133.25 Trumbull: 142.55 | |
| Sat., 2/4 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 3:00 p.m. | W 7-0 | |
| Mon., 2/6 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 6:45 p.m. | T 2-2(OT) | |
| Mon., 2/6 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks [Directions] | 2:45 p.m. | ||
| Mon., 2/6 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Mon., 2/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice Rink [Directions] | 6:00 p.m. | W 9-0 | |
| Tue., 2/7 | V Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 52-38 | |
| Tue., 2/7 | JV Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/7 | JV Boys Ice Hockey | Ridgefield | Away - Brewster Ice Rink [Directions] | Cancelled | Cancelled | @ Brewsters Ice Arena |
| Tue., 2/7 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 7:00 p.m. | W 63-52 | |
| Tue., 2/7 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | 6:00 p.m. | L 1-3 | |
| Wed., 2/8 | JV Boys Squash | Bronxville (NY) | Home - Chelsea Piers [Directions] | 8:00 p.m. | ||
| Wed., 2/8 | V Boys Swimming and Diving | Danbury | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/8 | V Wrestling | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | ||
| Wed., 2/8 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | ||
| Thu., 2/9 | V Boys Squash | HS Nationals Feb 9-12 | Away | TBA | ||
| Sat., 2/11 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice Rink [Directions] | 6:00 p.m. | L 0-1(OT) | |
| Sat., 2/11 | V Boys Indoor Track | Class L Championship @ Hillhouse | Away | 4:00 p.m. | ||
| Sat., 2/11 | V Wrestling | FCIAC Championship- New Canaan HS | Away | 8:00 a.m. | ||
| Sat., 2/11 | V Wrestling | FCIAC Chmapionship- New Canaan HS | Away | Cancelled | Cancelled | |
| Sat., 2/11 | V Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 52-42 | |
| Sat., 2/11 | JV Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 2:30 p.m. | ||
| Sat., 2/11 | V Girls Gymnastics | FCIAC's @ Jonathan Law HS | Away | 9:30 a.m. | Darien HS: 3rd place | |
| Sat., 2/11 | V Girls Indoor Track | Class L Championship @ Hillhouse | Away | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | W 72-68 | |
| Mon., 2/13 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Ice Hockey | Wilton | Home - Darien Ice Rink [Directions] | 6:00 p.m. | W 7-1 | |
| Mon., 2/13 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks [Directions] | 2:45 p.m. | ||
| Mon., 2/13 | V Girls Basketball | St. Joseph | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 51-56 | |
| Mon., 2/13 | JV Girls Basketball | St. Joseph | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 8:10 p.m. | W 2-0 | |
| Wed., 2/15 | V Boys Basketball | Westhill | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 59-42 | |
| Wed., 2/15 | JV Boys Basketball | Westhill | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Westhill | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Darien Ice Rink [Directions] | 8:00 p.m. | W 3-2(OT) | |
| Wed., 2/15 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 52-65 | |
| Wed., 2/15 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Girls Gymnastics | Ro Carlucci Invitational @ Westhill HS | Away | 5:30 p.m. | Pickup @ Darien YMCA | |
| Wed., 2/15 | V Girls Ice Hockey | Greenwich Academy | Away - Chelsea Piers- CT | 3:00 p.m. | ||
| Thu., 2/16 | JV Boys Ice Hockey | St. Lukes | Home - Stamford Twin Rinks [Directions] | 3:00 p.m. | ||
| Thu., 2/16 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 2:10 p.m. | W 9-0 | |
| Fri., 2/17 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:00 p.m. | W 49-40 | |
| Fri., 2/17 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:00 p.m. | ||
| Fri., 2/17 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 1:30 p.m. | ||
| Fri., 2/17 | V Wrestling | Class L Championship- Bristol Central | Away | TBA | ||
| Fri., 2/17 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice Rink [Directions] | 7:20 p.m. | W 9-1 | |
| Sat., 2/18 | V Boys Ice Hockey | Trinity Catholic | Home - Darien Ice Rink [Directions] | 7:00 p.m. | W 6-0 | |
| Sat., 2/18 | JV Boys Ice Hockey | Ridgefield | Home - Stamford Twin Rinks [Directions] | 2:10 p.m. | ||
| Sat., 2/18 | V Wrestling | Class L Championship- Bristol Central | Away | TBA | ||
| Mon., 2/20 | V Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 7:00 p.m. | W 62-38 | |
| Mon., 2/20 | JV Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 2/20 | V Boys Indoor Track | State Open @ Hillhouse | Away | 4:00 p.m. | ||
| Mon., 2/20 | V Girls Indoor Track | State Open @ Hillhouse | Away | 4:00 p.m. | ||
| Wed., 2/22 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 7:00 p.m. | W 50-40 | |
| Wed., 2/22 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:00 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/22 | V Girls Ice Hockey | FCIAC Semi-Finals vs Fairfield Warde/Ludlowe | Home - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Fri., 2/24 | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 2/24 | V Wrestling | State Open- Hillhouse | Away | TBA | ||
| Fri., 2/24 | V Girls Basketball | CIAC Qualifying Round vs West Haven | Home - DHS Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 2/25 | V Boys Basketball | FCIAC QUARTERFINALS vs Danbury @ Fairfield Warde | Away | 2:00 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Tentative FCIAC Playdowns @ Terry Connors | Away | Cancelled | Cancelled | Games @ 3 & 5 p.m. |
| Sat., 2/25 | V Boys Indoor Track | Pre-Nationals @ The Armory | Away | 6:00 p.m. | ||
| Sat., 2/25 | V Wrestling | State Open- Hillhouse | Away | TBA | ||
| Sat., 2/25 | V Girls Gymnastics | CIAC Championships @ Pomperaug | Away | TBA | Pickup and drop off @ Darien YMCA | |
| Sat., 2/25 | V Girls Ice Hockey | FCIAC Finals vs Greenwich @ Terry Conners | Away | 12:30 p.m. | ||
| Mon., 2/27 | V Girls Ice Hockey | State Quarter-Finals vs New Canaan @ Darien Ice | Home - Darien Ice Rink [Directions] | 6:10 p.m. | ||
| Tue., 2/28 | V Boys Basketball | Tentative FCIAC Semi-Finals @ Fairfield Warde | Away | Cancelled | Cancelled | |
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Boys Swim Trials @ Greenwich HS | Away | 4:30 p.m. | ||
| Tue., 2/28 | V Girls Basketball | CIAC Class LL - First Round @ Trumbull | Away | 5:00 p.m. | ||
| Wed., 3/1 | V Boys Basketball | Trinity Catholic (Scrim.) | Away | 4:30 p.m. | ||
| Wed., 3/1 | V Boys Ice Hockey | Tentative FCIAC Semi-Finals @ Terry Connors | Away | Cancelled | Cancelled | Games at 6 & 8 p.m. |
| Wed., 3/1 | V Boys Swimming and Diving | FCIAC Diving Finals @ Westhill | Away | 4:30 p.m. | ||
| Thu., 3/2 | V Boys Basketball | Tentative FCIAC Final @ Fairfield Warde | Away | Cancelled | Cancelled | |
| Thu., 3/2 | V Boys Swimming and Diving | FCIAC Boys Swim Finals @ Greenwich HS | Away | 6:30 p.m. | ||
| Thu., 3/2 | V Girls Ice Hockey | State Semi-Final vs East Cahtolic at Rinks @ Shelton | Away | 7:30 p.m. | ||
| Fri., 3/3 | V Boys Basketball | CIAC Class LL - Qualifying Round | Away | Cancelled | Cancelled | |
| Fri., 3/3 | V Girls Basketball | Tentative CIAC Class LL - Second Round | Away | Cancelled | Cancelled | |
| Sat., 3/4 | V Boys Ice Hockey | Tentative FCIAC Final @ Terry Connors | Away | Cancelled | Cancelled | |
| Sat., 3/4 | V Boys Indoor Track | New England Championshps @ Reggie Lewis Center, Boston, MA | Away | TBA | ||
| Sat., 3/4 | V Girls Gymnastics | State Open Championhip | Away | TBA | ||
| Sat., 3/4 | V Girls Ice Hockey | Tentative State Final @ Bennett Rink, West Haven | Away | 7:00 p.m. | ||
| Sat., 3/4 | V Girls Indoor Track | New England Championships @ Reggies Lewis Center, Boston, MA | Away | TBA | ||
| Mon., 3/6 | V Boys Basketball | CIAC Class LL - First Round vs West Haven | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 3/8 | V Boys Basketball | CIAC Class LL - Second Round @ East Hartford HS | Away | 6:00 p.m. | ||
| Wed., 3/8 | V Boys Ice Hockey | CIAC vs Ridgefield - Round 1 @ Winter Garden | Away | 6:40 p.m. | ||
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 3/9 | V Girls Basketball | Tentative CIAC Class LL - Quarter-finals | Away | Cancelled | Cancelled | |
| Fri., 3/10 | V Boys Basketball | Tentative CIAC Class LL - Quarter-finals | Away | Cancelled | Cancelled | |
| Sat., 3/11 | V Boys Ice Hockey | Tentative CIAC Quarterfinals | Away | Cancelled | Cancelled | |
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Kennedy HS [Directions] | 4:30 p.m. | ||
| Sat., 3/11 | V Girls Gymnastics | New Englands | Away | TBA | ||
| Mon., 3/13 | V Girls Basketball | Tentative CIAC Class LL - Semi-finals | Away | Cancelled | Cancelled | |
| Tue., 3/14 | V Boys Basketball | Tentative CIAC Class LL - Semi-Finals | Away | Cancelled | Cancelled | |
| Tue., 3/14 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | ||
| Wed., 3/15 | V Boys Ice Hockey | Tentative CIAC Semi-Finals @ Ingalls Rink | Away | Cancelled | Cancelled | Games at 5:30 and 7:30 p.m. |
| Fri., 3/17 | V Boys Rugby | Fairfield Prep B | Away | Cancelled | Cancelled | |
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Basketball | Tentative CIAC Class LL - Final @ Mohegan Sun Arena | Away | Cancelled | Cancelled | |
| Sat., 3/18 | V Boys Ice Hockey | Tentative CIAC Finals @ Ingalls Rink | Away | Cancelled | Cancelled | |
| Sat., 3/18 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Sat., 3/18 | V Girls Basketball | Tentative CIAC Class LL - Finals @ Mohegan Sun Arena | Away | Cancelled | Cancelled | |
| Tue., 3/21 | V Softball | Staples (Scrim.) | Home - DHS Baseball JV Field [Directions] | 3:30 p.m. | ||
| Wed., 3/22 | V Boys Lacrosse | Blue/White Scrimmage | Home - DHS Turf #2 [Directions] | 3:30 p.m. | ||
| Fri., 3/24 | V Softball | Westhill (Scrim.) | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Baseball | Brien McMahon (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 3/25 | V Boys Lacrosse | DHS Jamboree | Home - DHS Turf #2 [Directions] | 8:30 a.m. | Warm-up at 8:00 a.m. | |
| Sat., 3/25 | FR Boys Lacrosse | Chaminade (NY) (Scrim.) | Away | 12:00 p.m. | ||
| Sat., 3/25 | V Boys Volleyball | Blue Wave Volleyball Playday | Home - DHS Main Gym [Directions] | 7:00 a.m. | DHS Main Gym, North Gym & South Gym | |
| Sat., 3/25 | V Softball | Stamford (Scrim.) | Home - DHS Baseball JV Field [Directions] | 2:30 p.m. | ||
| Mon., 3/27 | V Girls Lacrosse | New Canaan (Scrim.) | Home - DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Wed., 3/29 | V Boys Lacrosse | Salisbury School (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Co-ed Sailing | Staples HS, Stamford HS, Darien @ Cedar Point YC, Westport | Away | Cancelled | Cancelled | TO BE RESCHEDULED |
| Wed., 3/29 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Away | 3:45 p.m. | ||
| Wed., 3/29 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Away | 5:00 p.m. | ||
| Thu., 3/30 | V Baseball | Wilton (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | JV Baseball | Wilton (Scrim.) | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Fri., 3/31 | V Boys Rugby | Aspetuck | Away | Cancelled | Cancelled | |
| Sat., 4/1 | V Boys Lacrosse | Yorktown (NY) | Home - DHS Stadium Field [Directions] | 2:00 p.m. | W 15-4 | |
| Sat., 4/1 | JV Boys Lacrosse | Yorktown (NY) | Home - DHS Turf #2 [Directions] | 4:30 p.m. | ||
| Sat., 4/1 | V Boys Volleyball | Masuk | Home - DHS Main Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 4/1 | JV Boys Volleyball | Masuk | Home - DHS Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Yorktown (NY) | Home - DHS Stadium Field [Directions] | 11:00 a.m. | W 20-4 | |
| Sat., 4/1 | JV Girls Lacrosse | Yorktown (NY) | Home - DHS Turf #2 [Directions] | 12:30 p.m. | ||
| Sun., 4/2 | V Baseball | Fitch | Away - Fitch HS-Baseball Field [Directions] | 2:00 p.m. | W 5-1 | |
| Mon., 4/3 | FR Baseball | Trinity Catholic | Home - DHS Baseball JV Field [Directions] | 3:45 p.m. | ||
| Mon., 4/3 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 4/3 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | L 3-4 | |
| Mon., 4/3 | V Girls Outdoor Track | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/3 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-2 | Non League |
| Mon., 4/3 | V Girls Tennis | Greenwich | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/4 | V Boys Lacrosse | Brien McMahon | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 22-1 | |
| Tue., 4/4 | JV Boys Lacrosse | Brien McMahon | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Wed., 4/5 | V Baseball | New Fairfield | Home - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | L 5-7 | |
| Wed., 4/5 | JV Baseball | New Fairfield | Home - DHS Baseball JV Field [Directions] | 4:30 p.m. | No metal spikes | |
| Wed., 4/5 | FR Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 6:00 p.m. | ||
| Wed., 4/5 | FR Boys Lacrosse | Danbury | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Wed., 4/5 | V Boys Outdoor Track | Greenwich | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Boys Tennis | Trumbull | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/5 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/5 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/5 | V Co-ed Sailing | Fairfield Prep, Brunswick, Darien @ Pequot YC, Southport | Away | 3:00 p.m. | ||
| Wed., 4/5 | FR Girls Lacrosse | Fairfield Ludlowe | Home - DHS Field #1 -Turf [Directions] | Cancelled | Cancelled | |
| Wed., 4/5 | V Softball | Norwich Free Academy | Home - DHS Softball Varsity Field [Directions] | 4:30 p.m. | L 2-6 | |
| Wed., 4/5 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/5 | JV Girls Tennis | Greenwich | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | JV Boys Golf | Ridgefield | Home - Woodway CC [Directions] | Cancelled | Cancelled | |
| Thu., 4/6 | V Co-ed Sailing | Fairfield Ludlowe, Darien, Greenwich @ Pequot YC, Southport | Away | Cancelled | Cancelled | |
| Fri., 4/7 | FR Baseball | New Canaan | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Fri., 4/7 | FR Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Fri., 4/7 | V Boys Volleyball | Staples | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/7 | JV Boys Volleyball | Staples | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/7 | V Girls Lacrosse | St. Joseph | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 20-5 | |
| Fri., 4/7 | JV Girls Lacrosse | St. Joseph | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 4/7 | FR Girls Lacrosse | Wilton | Home - DHS Field #1 -Turf [Directions] | 4:15 p.m. | ||
| Sat., 4/8 | V Baseball | Daniel Hand | Away - Polson Baseball Field/DHHS Campus [Directions] | 2:30 p.m. | L 1-8 | |
| Sat., 4/8 | JV Baseball | Daniel Hand | Home - DHS Baseball Varsity Field [Directions] | 11:00 a.m. | ||
| Sat., 4/8 | V Boys Lacrosse | Niskayuna (NY) | Away | 6:30 p.m. | W 17-9 | |
| Sat., 4/8 | JV Boys Lacrosse | Lincoln Sudbury & Greenwich | Home - DHS Turf #2 [Directions] | 3:00 p.m. | ||
| Sat., 4/8 | FR Boys Lacrosse | Hingham & Lincoln Sudbury | Home - DHS Field #1 -Turf [Directions] | 5:00 p.m. | ||
| Sat., 4/8 | V Girls Lacrosse | Ridgewood (NJ) | Home - DHS Stadium Field [Directions] | 3:00 p.m. | L 8-10 | |
| Sat., 4/8 | JV Girls Lacrosse | Ridgewood (NJ) | Home - DHS Turf #2 [Directions] | 1:30 p.m. | ||
| Sat., 4/8 | FR Girls Lacrosse | Ridgewood (NJ) | Home - DHS Stadium Field [Directions] | 12:00 p.m. | ||
| Sat., 4/8 | V Softball | Newtown | Home - DHS Softball Varsity Field [Directions] | 2:00 p.m. | L 3-4 | |
| Mon., 4/10 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 1:00 p.m. | W 11-1 | |
| Mon., 4/10 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 1:00 p.m. | ||
| Mon., 4/10 | FR Baseball | Greenwich | Home - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | 10:30 a.m. | W 6-1 | |
| Mon., 4/10 | V Softball | Greenwich | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 4=1 | |
| Mon., 4/10 | JV Softball | Greenwich | Home - DHS Softball JV Field [Directions] | Cancelled | Cancelled | |
| Mon., 4/10 | V Girls Tennis | Trinity Catholic | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/11 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 23-5 | |
| Tue., 4/11 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 4/11 | V Girls Lacrosse | Brien McMahon | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 20-1 | |
| Tue., 4/11 | JV Girls Lacrosse | Brien McMahon | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 4/12 | V Baseball | Trumbull | Home - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | L 4-5(8) | |
| Wed., 4/12 | JV Baseball | Trumbull | Home - DHS Baseball JV Field [Directions] | 1:00 p.m. | No metal spikes | |
| Wed., 4/12 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 1:00 p.m. | ||
| Wed., 4/12 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 1:00 p.m. | ||
| Wed., 4/12 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 10:00 a.m. | W 3-0 | |
| Wed., 4/12 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 11:30 a.m. | ||
| Wed., 4/12 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:15 p.m. | W 8-2 | |
| Wed., 4/12 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | Cancelled | Cancelled | |
| Thu., 4/13 | V Baseball | Bridgeport Central | Home - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | W 12-0 | |
| Thu., 4/13 | JV Baseball | Bridgeport Central | Home - DHS Baseball JV Field [Directions] | 1:00 p.m. | No metal spikes | |
| Thu., 4/13 | FR Baseball | Westhill | Home - DHS Baseball JV Field [Directions] | 10:00 a.m. | No metal spikes | |
| Thu., 4/13 | FR Boys Lacrosse | Stamford | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Thu., 4/13 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 19-8 | |
| Thu., 4/13 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Thu., 4/13 | V Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 2:00 p.m. | W 23-9 | |
| Thu., 4/13 | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | Cancelled | Cancelled | |
| Sat., 4/15 | V Boys Lacrosse | Manhassett (NY) | Away | 1:00 p.m. | W 12-8 | |
| Sat., 4/15 | JV Boys Lacrosse | Manhassett (NY) | Away | 10:30 a.m. | ||
| Sat., 4/15 | V Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 10:00 a.m. | W 3-1 | |
| Sat., 4/15 | JV Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 11:30 a.m. | ||
| Sat., 4/15 | V Girls Lacrosse | Garden City (NY) | Home - DHS Turf #2 [Directions] | 11:00 a.m. | L 11-17 | |
| Sat., 4/15 | JV Girls Lacrosse | Garden City (NY) | Home - DHS Field #1 -Turf [Directions] | 11:00 a.m. | ||
| Sat., 4/15 | V Softball | Trinity Catholic | Home - DHS Softball Varsity Field [Directions] | 11:00 a.m. | W 10-0 | |
| Mon., 4/17 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:00 p.m. | W 10-1 | |
| Mon., 4/17 | JV Baseball | Trinity Catholic | Away - Barrett Field @ Belltown Park | 4:00 p.m. | ||
| Mon., 4/17 | FR Baseball | Trinity Catholic | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | ||
| Mon., 4/17 | V Boys Tennis | Brien McMahon | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/17 | JV Boys Tennis | New Canaan | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/17 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/17 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | Cancelled | Cancelled | |
| Mon., 4/17 | V Girls Outdoor Track | Staples | Home - DHS Stadium Field [Directions] | 4:00 p.m. | Greenwich Academy is also participating | |
| Mon., 4/17 | V Softball | Fryeburg (ME) | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 7-5 | |
| Mon., 4/17 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/17 | JV Girls Tennis | New Canaan | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:30 p.m. | Darien 163 Wilton 180 | |
| Tue., 4/18 | JV Boys Golf | Wilton | Away [Directions] | 3:30 p.m. | ||
| Tue., 4/18 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | W 18-4 | |
| Tue., 4/18 | V Boys Outdoor Track | Staples | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Danbury | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/18 | JV Boys Tennis | Fairfield Warde | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | W 6-0 | |
| Tue., 4/18 | V Co-ed Sailing | Staples @ Cedar Point YC | Away | 3:00 p.m. | ||
| Tue., 4/18 | V Girls Golf | Danbury | Home - CC of Darien [Directions] | 3:00 p.m. | Darien 201 Danbury 248 | |
| Tue., 4/18 | JV Girls Golf | Danbury | Home - CC of Darien [Directions] | 3:00 p.m. | ||
| Tue., 4/18 | V Girls Lacrosse | Ridgefield | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 16-6 | |
| Tue., 4/18 | JV Girls Lacrosse | Ridgefield | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Tue., 4/18 | V Girls Tennis | Danbury | Home - Weed Beach [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/18 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Baseball | Brien McMahon | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 10-5 | |
| Wed., 4/19 | JV Baseball | Brien McMahon | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | No metal spikes | |
| Wed., 4/19 | V Boys Golf | Westhill | Home - CC of Darien [Directions] | 3:15 p.m. | Darien 166 Westhill 183 | |
| Wed., 4/19 | JV Boys Tennis | Fairfield Ludlowe | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | W 7-1 | |
| Wed., 4/19 | V Boys Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/19 | JV Boys Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/19 | V Co-ed Sailing | Greenwich Academy, Greens Farms Academy, Darien, Rye Country Day @ Indian Harbor, Greenwich | Away | 3:00 p.m. | ||
| Wed., 4/19 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | Darien 209 Greenwich 191 | |
| Wed., 4/19 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 16-2 | |
| Wed., 4/19 | JV Softball | Brien McMahon | Away - Brookside Elementary School [Directions] | Cancelled | Cancelled | |
| Wed., 4/19 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Darien 157 Ludlowe 175 | |
| Thu., 4/20 | JV Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 4/20 | JV Boys Lacrosse | Chaminade (NY) | Home - DHS Turf #2 [Directions] | 5:30 p.m. | FRESHMAN TEAM WILL PLAY | |
| Thu., 4/20 | V Boys Tennis | Stamford | Away [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/20 | V Girls Golf | New Canaan | Home - Woodway CC [Directions] | 3:00 p.m. | Darien 221 New Canaan 190 White Tees | |
| Thu., 4/20 | JV Girls Golf | Trumbull | Home - Woodway CC [Directions] | TBA | ||
| Thu., 4/20 | JV Girls Lacrosse | Greenwich Academy | Home - DHS Field #1 -Turf [Directions] | 3:30 p.m. | ||
| Thu., 4/20 | V Girls Tennis | Stamford | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 4/21 | V Baseball | Danbury | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | L 4-6 | |
| Fri., 4/21 | JV Baseball | Danbury | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | No metal spikes | |
| Fri., 4/21 | FR Boys Lacrosse | Wilton | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Fri., 4/21 | V Boys Rugby | West Hartford | Away | 5:30 p.m. | ||
| Fri., 4/21 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/21 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/21 | FR Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Sat., 4/22 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 11-4 | |
| Sat., 4/22 | JV Boys Lacrosse | Wilton | Away - Whitten Field [Directions] | 4:30 p.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Bayport-Bluepoint (NY) | Away | 10:00 a.m. | W 12-4 | |
| Mon., 4/24 | V Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 9-5 | |
| Mon., 4/24 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | FR Baseball | Stamford | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Golf | Fairfield Warde | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 158 Danbury 201 | |
| Mon., 4/24 | V Boys Golf | Danbury | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 158 Danbury 201 | |
| Mon., 4/24 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/24 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | T 3-3 | |
| Mon., 4/24 | V Boys Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/24 | JV Boys Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/24 | JV Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | @ New Canaan Country Club | |
| Mon., 4/24 | FR Girls Lacrosse | Ridgefield | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Girls Outdoor Track | St. Joseph, Norwalk | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Softball | Stamford | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 5-4 | |
| Mon., 4/24 | JV Girls Tennis | Wilton | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Golf | Brien McMahon | Home - CC of Darien [Directions] | 3:15 p.m. | Darien 165 McMahon 280 | |
| Tue., 4/25 | V Boys Lacrosse | St. Joseph | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 23-4 | |
| Tue., 4/25 | JV Boys Lacrosse | St. Joseph | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 20-3 | |
| Tue., 4/25 | JV Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Tue., 4/25 | FR Girls Lacrosse | Greenwich Academy | Away | 4:30 p.m. | ||
| Wed., 4/26 | FR Baseball | Wilton | Home - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | ||
| Wed., 4/26 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Darien 148 Norwalk 199 | |
| Wed., 4/26 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:15 p.m. | ||
| Wed., 4/26 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/26 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Co-ed Sailing | Stamford HS, Darien, Staples HS @ Stamford YC | Away | 3:00 p.m. | ||
| Wed., 4/26 | V Girls Golf | Ridgefield | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 203 Ridgefield 189 | |
| Wed., 4/26 | JV Girls Golf | Staples | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Wed., 4/26 | V Girls Lacrosse | Manhassett (NY) | Away | 6:30 p.m. | L 11-14 | |
| Wed., 4/26 | JV Girls Lacrosse | Manhassett (NY) | Away | 4:00 p.m. | ||
| Wed., 4/26 | V Girls Tennis | Wilton | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/27 | JV Baseball | Ridgefield | Home - DHS Baseball JV Field [Directions] | 4:15 p.m. | No metal spikes | |
| Thu., 4/27 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Thu., 4/27 | V Boys Tennis | Fairfield Warde | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/27 | V Co-ed Sailing | Brunswick, Fairfield Prep, Darien, Rye Country Day @ Indian Harbor, Greenwich | Away | 3:00 p.m. | ||
| Thu., 4/27 | V Girls Golf | Trumbull | Home - Woodway CC [Directions] | 3:00 p.m. | Darien 195 Trumbull 199 | |
| Thu., 4/27 | JV Girls Golf | Fairfield Ludlowe | Away - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Thu., 4/27 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 6:30 p.m. | W 10-0 | |
| Thu., 4/27 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/27 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Baseball | Ridgefield | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | L 3-4 | |
| Fri., 4/28 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | JV Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Boys Lacrosse | New Canaan | Home - DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Fri., 4/28 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away | 6:00 p.m. | ||
| Fri., 4/28 | V Boys Tennis | Ridgefield | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 4/28 | JV Boys Tennis | Ridgefield | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/28 | V Boys Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 4/28 | JV Boys Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/28 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 6:00 p.m. | ||
| Fri., 4/28 | FR Girls Lacrosse | New Canaan | Home - DHS Stadium Field [Directions] | 3:30 p.m. | ||
| Fri., 4/28 | V Girls Outdoor Track | Freshmen Only @ Cheshire | Away | 4:00 p.m. | ||
| Fri., 4/28 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | W 7-6 | |
| Fri., 4/28 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Sat., 4/29 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | W 11-8 | |
| Sat., 4/29 | FR Boys Lacrosse | Don Bosco (NJ) | Away | TBA | ||
| Sat., 4/29 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away | 9:00 a.m. | ||
| Sat., 4/29 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 1:30 p.m. | W 11-10(2OT) | |
| Sat., 4/29 | V Girls Outdoor Track | O'Grady Relays @ Danbury | Away | 9:30 a.m. | ||
| Mon., 5/1 | V Baseball | Fairfield Warde | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 12-1 | |
| Mon., 5/1 | JV Baseball | Fairfield Warde | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | No metal spikes | |
| Mon., 5/1 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | FR Boys Lacrosse | Staples | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/1 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | W 6-2 | |
| Mon., 5/1 | V Boys Volleyball | Trumbull | Home - DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/1 | JV Boys Volleyball | Trumbull | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Girls Golf | Fairfield Ludlowe | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 209 Ludlow 218 | |
| Mon., 5/1 | JV Girls Golf | Fairfield Ludlowe | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Mon., 5/1 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Mon., 5/1 | V Girls Outdoor Track | Fairfield Warde, Wilton | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | W 14-1 | |
| Mon., 5/1 | V Girls Tennis | Fairfield Ludlowe | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/1 | JV Girls Tennis | Fairfield Ludlowe | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:30 p.m. | L 1-3 | |
| Tue., 5/2 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:30 p.m. | ||
| Tue., 5/2 | JV Boys Golf | Ridgefield, New Canaan | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:30 p.m. | ||
| Tue., 5/2 | V Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | 5:30 p.m. | W 19-4 | |
| Tue., 5/2 | JV Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | Wilton, Fairfield Warde | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Boys Tennis | Staples | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 5/2 | JV Boys Tennis | Staples | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | L 0-6 | |
| Tue., 5/2 | V Girls Golf | Wilton | Home - CC of Darien [Directions] | 3:15 p.m. | Darien 192 Wilton 205 | |
| Tue., 5/2 | V Girls Lacrosse | Trumbull | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 20-3 | |
| Tue., 5/2 | JV Girls Lacrosse | Trumbull | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 5/2 | FR Girls Lacrosse | Greenwich Country Day | Away | 3:30 p.m. | ||
| Tue., 5/2 | V Softball | Wilton | Home - DHS Softball Varsity Field [Directions] | 4:30 p.m. | W 5-1 | |
| Tue., 5/2 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 5/3 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | JV Boys Golf | Wilton | Home - Woodway CC [Directions] | 3:15 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Bridgeport Central | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/3 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/3 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/3 | V Co-ed Sailing | Greenwich HS, Darien, Fairfield Ludlowe, Rye HS @ Grass Island, Greenwich | Away | 3:00 p.m. | ||
| Wed., 5/3 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | Darien 187 Ludlowe 219 | |
| Wed., 5/3 | JV Girls Golf | New Canaan | Home - Woodway CC [Directions] | 3:15 p.m. | ||
| Wed., 5/3 | V Softball | Fairfield Ludlowe | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 5/3 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/3 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Baseball | Staples | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/4 | JV Baseball | Staples | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | No metal spikes | |
| Thu., 5/4 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | Darien 167 Greenwich 156 | |
| Thu., 5/4 | V Boys Lacrosse | St. Anthonys (NY) | Away | 7:00 p.m. | W 9-4 | |
| Thu., 5/4 | JV Boys Lacrosse | St. Anthonys (NY) | Away | 4:30 p.m. | ||
| Thu., 5/4 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Thu., 5/4 | JV Boys Tennis | New Canaan | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/4 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 6:00 p.m. | W 15-2 | |
| Thu., 5/4 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:15 p.m. | ||
| Thu., 5/4 | JV Softball | Trinity Catholic | Home - DHS Softball JV Field [Directions] | 3:30 p.m. | ||
| Thu., 5/4 | V Girls Tennis | New Canaan | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/4 | JV Girls Tennis | New Canaan | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Boys Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/5 | JV Boys Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 5/6 | V Boys Lacrosse | Ridgefield | Home - DHS Stadium Field [Directions] | 2:30 p.m. | W 10-3 | |
| Sat., 5/6 | JV Boys Lacrosse | Ridgefield | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Sat., 5/6 | FR Boys Lacrosse | Don Bosco (NJ) | Away | TBA | ||
| Sat., 5/6 | V Boys Outdoor Track | Amity HS Midnight Meet, Woodbridge, CT | Away | 5:00 p.m. | ||
| Sat., 5/6 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | L 3-4 | |
| Sun., 5/7 | V Softball | Staples | Away - Wakeman Field [Directions] | 1:00 p.m. | W 6-0 | |
| Mon., 5/8 | V Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | L 10-11 | |
| Mon., 5/8 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | FR Baseball | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | JV Boys Golf | New Canaan | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Mon., 5/8 | FR Boys Lacrosse | Ridgefield | Home - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Mon., 5/8 | V Boys Tennis | St. Joseph | Home - Weed Beach Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/8 | JV Boys Tennis | Greenwich | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | W 7-1 | |
| Mon., 5/8 | V Boys Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/8 | JV Boys Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/8 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | Darien 205 NC 182 | |
| Mon., 5/8 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:15 p.m. | W 21-5 | |
| Mon., 5/8 | JV Girls Lacrosse | Greenwich Academy | Away | 3:30 p.m. | ||
| Mon., 5/8 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Girls Outdoor Track | Fairfield Ludlowe, Brien McMahon | Away - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Softball | New Canaan | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 8-4 | |
| Mon., 5/8 | V Girls Tennis | St. Joseph | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/8 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | 3:15 p.m. | Darien 150 Stamford 195 | |
| Tue., 5/9 | V Boys Lacrosse | Norwalk | Home - DHS Turf #2 [Directions] | 4:00 p.m. | W 23-0 | |
| Tue., 5/9 | JV Boys Lacrosse | Norwalk | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Brien McMahon, Fairfield Ludlowe | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Westhill | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 5/9 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/9 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | JV Softball | New Canaan | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Westhill | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/9 | JV Girls Tennis | Ridgefield | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 7-2 | |
| Wed., 5/10 | JV Baseball | St. Joseph | Away - Madison MS, Trumbull [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Baseball | St. Joseph | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Golf | Ridgefield | Home - CC of Darien [Directions] | 3:15 p.m. | Darien 166 Ridgefield 169 | |
| Wed., 5/10 | FR Boys Lacrosse | Glastonbury | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Rugby | Greenwich B | Home - Royle School Field [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/10 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Wed., 5/10 | V Co-ed Sailing | Greens Farms Academy, Greenwich Academy, Darien @ Pequot YC, Southport | Away | 3:00 p.m. | ||
| Wed., 5/10 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:00 p.m. | Darien 185 Warde 177 | |
| Wed., 5/10 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | W 22-6 | |
| Wed., 5/10 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | ||
| Wed., 5/10 | FR Girls Lacrosse | Norwalk | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Girls Outdoor Track | Freshmen/Sophomore Meet | Home - DHS Stadium Field [Directions] | 4:00 p.m. | Rain Date = 5/18/17 | |
| Wed., 5/10 | V Girls Outdoor Track | Freshman/Sophomore Meet | Home - DHS Track [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Softball | St. Joseph | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 5/11 | V Baseball | Westhill | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | L 8-10 | |
| Thu., 5/11 | JV Baseball | Westhill | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | No metal spikes | |
| Thu., 5/11 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Golf | Trumbull | Home - Woodway CC [Directions] | 3:15 p.m. | Darien 151 Trumbull 161 | |
| Thu., 5/11 | V Boys Lacrosse | Trinity Catholic | Away - Trinity Gaglio Field | 4:00 p.m. | W 21-4 | |
| Thu., 5/11 | JV Boys Lacrosse | Staples | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Outdoor Track | St. Joseph, Norwalk | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | JV Boys Tennis | Greenwich | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | L 2-6 | |
| Thu., 5/11 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Darien 196 Trumbull 194 | |
| Thu., 5/11 | JV Girls Golf | Trumbull | Away [Directions] | 3:15 p.m. | @ Tashua | |
| Thu., 5/11 | V Girls Lacrosse | Fairfield Warde | Home - DHS Turf #2 [Directions] | 5:00 p.m. | W 18-5 | |
| Thu., 5/11 | JV Girls Lacrosse | Fairfield Warde | Home - DHS Turf #2 [Directions] | 6:30 p.m. | ||
| Thu., 5/11 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | L 2-5 | |
| Thu., 5/11 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | FR Boys Lacrosse | St. Joseph | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | V Boys Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 3:30 p.m. | W 3-0 | |
| Fri., 5/12 | JV Boys Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 5/13 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 3:00 p.m. | W 12-8 | |
| Sat., 5/13 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 1:00 p.m. | ||
| Sat., 5/13 | V Co-ed Sailing | Fairfield Cup @ Pequot YC, Southport | Away | 9:00 a.m. | ||
| Mon., 5/15 | V Boys Golf | Staples | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 162 Staples 166 | |
| Mon., 5/15 | JV Boys Golf | Staples | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Mon., 5/15 | FR Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:00 p.m. | ||
| Mon., 5/15 | V Boys Rugby | Cheshire @ 1325 Cheshire St. Cheshire, CT | Away | 4:30 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Norwalk | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/15 | V Boys Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/15 | JV Boys Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/15 | V Girls Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | Darien 208 Staples 197 | |
| Mon., 5/15 | JV Girls Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | @ Longshore | |
| Mon., 5/15 | V Girls Outdoor Track | New Canaan | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Girls Tennis | Norwalk | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/16 | V Baseball | Norwich Free Academy | Away - Dodd Stadium [Directions] | 4:00 p.m. | W 7-6(9) | |
| Tue., 5/16 | JV Baseball | Fairfield Ludlowe | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | Darien 165 New Canaan 179 | |
| Tue., 5/16 | JV Boys Golf | Greenwich | Home - CC of Darien [Directions] | 3:15 p.m. | ||
| Tue., 5/16 | V Boys Lacrosse | Stamford | Home - DHS Stadium Field [Directions] | 5:30 p.m. | W 22-2 | |
| Tue., 5/16 | JV Boys Lacrosse | Stamford | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | FR Boys Lacrosse | Greenwich | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | JV Boys Tennis | Fairfield Warde | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/16 | V Girls Golf | Fairfield Warde | Home - CC of Darien [Directions] | 3:30 p.m. | Darien 200 Warde 201 | |
| Tue., 5/16 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | JV Softball | Norwalk | Home - DHS Softball JV Field [Directions] | 4:30 p.m. | ||
| Tue., 5/16 | JV Girls Tennis | Staples | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 6:00 p.m. | W 8-0 | |
| Wed., 5/17 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | Norwalk | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | JV Boys Golf | Fairfield Warde/Fairfield Ludlowe @ Smith Richardson GC, Fairfield | Away | 3:15 p.m. | ||
| Wed., 5/17 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | Cancelled | Cancelled | |
| Wed., 5/17 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 5/17 | V Boys Volleyball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/17 | JV Boys Volleyball | Danbury | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/17 | JV Girls Golf | Fairfield Ludlowe | Away - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Wed., 5/17 | FR Girls Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Softball | Norwalk | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 9-6 | |
| Wed., 5/17 | V Girls Tennis | Fairfield Warde | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | FCIAC Quarter Finals |
| Thu., 5/18 | JV Boys Golf | New Canaan, Ridgefield | Home - Woodway CC [Directions] | 3:15 p.m. | ||
| Thu., 5/18 | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | V Boys Rugby | Southington | Home - Royle School Field [Directions] | 5:00 p.m. | ||
| Thu., 5/18 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 3:30 p.m. | L 0-3 | |
| Thu., 5/18 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 5/18 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:30 p.m. | Darien 181 Danbury 219 | |
| Thu., 5/18 | JV Girls Golf | Greenwich | Away - Millbrook CC [Directions] | 3:15 p.m. | ||
| Thu., 5/18 | FR Girls Lacrosse | Fairfield Warde | Home - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | V Girls Outdoor Track | Freshmen/Sophomore Meet (Rain Date | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 5/19 | V Baseball | FCIAC Quarterfinal @ Staples | Away | 4:00 p.m. | ||
| Fri., 5/19 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/19 | V Boys Outdoor Track | Freshmen Hatter Invitational @ Danbury HS | Away | 4:00 p.m. | ||
| Fri., 5/19 | V Co-ed Sailing | FCSL Silver Cup @ Indian Harbory YC, Greenwich | Away | 3:00 p.m. | ||
| Fri., 5/19 | V Girls Lacrosse | FCIACS vs Trumbull | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Fri., 5/19 | V Softball | FCIACS vs Ridgefield | Home [Directions] | 2:00 p.m. | ||
| Sat., 5/20 | V Boys Lacrosse | FCIAC Quarter Final vs Fairfield Ludlowe | Home - DHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 5/20 | FR Boys Lacrosse | Fairfield Prep | Home - DHS Stadium Field [Directions] | 1:00 p.m. | ||
| Sat., 5/20 | V Co-ed Sailing | FCSL Gold Cup @ Indian Harbor, Greenwich | Away | 9:00 a.m. | ||
| Mon., 5/22 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | 3:30 p.m. | Darien 174 Wilton 176 | |
| Mon., 5/22 | V Girls Lacrosse | FCIAC Semi-Finals vs Staples @ Norwalk HS | Away | 7:00 p.m. | ||
| Tue., 5/23 | V Boys Golf | St. Joseph | Away [Directions] | 3:15 p.m. | Darien 138 St. Joseph 159 | |
| Tue., 5/23 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Tue., 5/23 | V Boys Lacrosse | FCIAC Semi-finals vs Wilton @ Brien McMahon | Away | 7:30 p.m. | ||
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Championship @ Ridgefield HS | Away | 3:00 p.m. | ||
| Tue., 5/23 | V Boys Tennis | FCIAC Semi-finals @ Staples | Away | 4:00 p.m. | ||
| Tue., 5/23 | V Softball | FCIAC Semi-finals vs Fairfield Ludlowe @ Sacred Heart Univ. | Away | 3:00 p.m. | ||
| Tue., 5/23 | V Girls Tennis | FCIAC Final vs Staples @ Wilton | Away | 4:00 p.m. | ||
| Wed., 5/24 | V Baseball | FCIAC Semi-Finals vs Wilton @ Harbor Yard | Away | 5:00 p.m. | ||
| Wed., 5/24 | V Boys Golf | Trinity Catholic, Wilton | Away - Sterling Farms | 3:15 p.m. | Darien 162 Trinity 190 | |
| Wed., 5/24 | V Boys Rugby | Fairfield Prep | Away [Directions] | 4:00 p.m. | ||
| Wed., 5/24 | V Boys Tennis | Tentative FCIAC Finals @ Wilton | Away | Cancelled | Cancelled | |
| Wed., 5/24 | V Boys Volleyball | FCIAC Semi-finals vs Staples @ Fairfield Ludlowe | Away | 7:00 p.m. | ||
| Wed., 5/24 | V Girls Golf | Danbury | Home - Fairchild Wheeler [Directions] | 3:00 p.m. | Darien 178 Danbury 224 | |
| Wed., 5/24 | JV Girls Golf | Eckstrom Tournament | Away | TBA | ||
| Wed., 5/24 | V Girls Lacrosse | FCIAC Final vs Ridgefield @ Norwalk HS | Away | 7:00 p.m. | ||
| Wed., 5/24 | V Girls Outdoor Track | FCIAC Championships @ Danbury HS | Away | 3:00 p.m. | ||
| Wed., 5/24 | V Softball | FCIAC Final vs Westhill @ Sacred Heart Univ. | Away | 5:00 p.m. | ||
| Thu., 5/25 | V Boys Golf | Chappa- Longshore | Away | 12:00 p.m. | ||
| Thu., 5/25 | V Boys Lacrosse | FCIAC Final vs Ridgefield @ Brien McMahon | Away | 6:00 p.m. | ||
| Fri., 5/26 | V Baseball | Tentative FCIAC Finals @ Harbor Yard | Away | Cancelled | Cancelled | |
| Fri., 5/26 | V Boys Volleyball | FCIAC Final vs Ridgefield @ Fairfield Ludlowe | Away | 7:00 p.m. | ||
| Fri., 5/26 | V Girls Outdoor Track | Non Varsity Freshmen Only @ Wilton | Away | Cancelled | Cancelled | |
| Sat., 5/27 | V Baseball | CIAC - Qualifying Round @ higher seed | Home - DHS Baseball Varsity Field [Directions] | Cancelled | Cancelled | |
| Sat., 5/27 | V Boys Tennis | CIAC Class L - Round 1 @ William Hall HS, W. Hartford | Away | 8:30 a.m. | ||
| Sat., 5/27 | V Girls Tennis | CIAC - Round 1 vs Southington/Hall winner | Home - DHS Tennis Courts [Directions] | 12:30 p.m. | ||
| Tue., 5/30 | V Baseball | CIAC - Round 1 vs Danbury | Home - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Tue., 5/30 | V Boys Golf | Holohan | Home - CC of Darien [Directions] | 12:30 p.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | Class L Championship @ Manchester HS | Away [Directions] | 3:00 p.m. | ||
| Tue., 5/30 | V Boys Tennis | CIAC Quarterfinals @ William Hall HS, W. Hartford | Away | 1:00 p.m. | ||
| Tue., 5/30 | V Girls Lacrosse | CIAC Round 1 vs Southington | Home - DHS Turf #2 [Directions] | 4:30 p.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class L Championship @ Manchester HS | Away [Directions] | 3:00 p.m. | ||
| Tue., 5/30 | V Softball | CIAC Round 1 vs New Britain | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 5/30 | V Girls Tennis | CIAC Quarter-finals | Home - DHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 5/31 | V Baseball | Tentative CIAC - Round 2 @ higher seed | Away | Cancelled | Cancelled | |
| Wed., 5/31 | V Boys Lacrosse | CIAC vs Conard | Home - DHS Turf #2 [Directions] | 4:30 p.m. | ||
| Wed., 5/31 | V Boys Tennis | Tentative CIAC Semi-finals @ Yale | Away | Cancelled | Cancelled | |
| Wed., 5/31 | V Boys Volleyball | CIAC - Round 1 vs Newtown | Home - DHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/31 | V Softball | CIAC Round 2 @ Southington | Away | 4:00 p.m. | ||
| Wed., 5/31 | V Girls Tennis | Tentative CIAC Semi-finals @ Staples | Away - DHS Tennis Courts | Cancelled | Cancelled | |
| Thu., 6/1 | V Boys Golf | FCIAC's @ Fairchild Wheeler GC | Away | 12:00 p.m. | ||
| Thu., 6/1 | V Boys Tennis | Tentative CIAC Finals @ Conard HS | Away | Cancelled | Cancelled | Rain date is June 2nd |
| Thu., 6/1 | V Girls Golf | FCIAC Championship @ Wheel Blank | Away | 9:00 a.m. | ||
| Thu., 6/1 | V Girls Lacrosse | CIAC Round 2 | Home - DHS Turf #2 [Directions] | 5:00 p.m. | ||
| Thu., 6/1 | V Girls Tennis | Tentative CIAC Finals @ Yale | Away | Cancelled | Cancelled | Rain date June 2nd |
| Fri., 6/2 | V Boys Volleyball | CIAC - Quarterfinals vs Shelton | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 6/2 | V Softball | Tentative CIAC Quarterfinals @ higher ranked | Away | Cancelled | Cancelled | Rain date 6/3 |
| Sat., 6/3 | V Baseball | Tentative CIAC - Quarterfinals @ higher seed | Away | Cancelled | Cancelled | |
| Sat., 6/3 | V Boys Lacrosse | CIAC Quarterfinals | Home - DHS Turf #2 [Directions] | 3:00 p.m. | ||
| Sat., 6/3 | V Boys Lacrosse | CIAC Quarterfinals vs Greenwich | Home - DHS Turf #2 [Directions] | 3:00 p.m. | ||
| Sat., 6/3 | V Boys Tennis | State Open @ Amity HS | Away | Cancelled | Cancelled | Makeup date 6/4/17 |
| Sat., 6/3 | V Girls Tennis | State Open @ Conard/William Hall HS, W. Hartford | Away | 1:00 p.m. | Rain date 6/4 | |
| Mon., 6/5 | V Boys Outdoor Track | State Open @ Willow Brook Park, New Britain, CT | Away | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | Tentative State Open Quarterfinals @ Yale | Away | Cancelled | Cancelled | |
| Mon., 6/5 | V Boys Volleyball | CIAC Semi-finals vs Ridgefield @ Fairfield Warde | Away | 6:00 p.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open @ Willowbrook Park, New Britain | Away | 1:30 p.m. | ||
| Mon., 6/5 | V Softball | Tentative CIAC Semi-finals @ DeLuca Field and West Haven | Away | Cancelled | Cancelled | or 6/6/16 |
| Mon., 6/5 | V Girls Tennis | State Open - Quarterfinals @ Yale | Away | 12:00 p.m. | ||
| Tue., 6/6 | V Baseball | Tentative CIAC - Semi-finals @ neutral site | Away | Cancelled | Cancelled | |
| Tue., 6/6 | V Boys Golf | State Tourney @ Fairview Farms GC, Harwington, CT | Away | TBA | ||
| Tue., 6/6 | V Boys Tennis | Tentative State Open Semi-finals @ Yale | Away | Cancelled | Cancelled | |
| Tue., 6/6 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | ||
| Tue., 6/6 | V Girls Lacrosse | CIAC Semi-finals vs New Canaan @ Brien McMahon | Away | 8:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | Tentative State Open - Semi-finals @ Yale | Away | 3:00 p.m. | ||
| Wed., 6/7 | V Boys Lacrosse | CIAC Semi-finals vs Glastonbury @ Fairfield Prep | Away | 5:00 p.m. | ||
| Wed., 6/7 | V Boys Lacrosse | CIAC Semi-finals vs Glastonbury @ Fairfield Prep | Away | 5:00 p.m. | ||
| Wed., 6/7 | V Boys Tennis | Tentative State Open Finals @ CT Tennis Center | Away | Cancelled | Cancelled | Rain date is June 8th |
| Wed., 6/7 | V Girls Golf | Guimares Tournament @ Orange Hills GC | Away | 12:30 a.m. | Lunch @ 11:30 a.m. | |
| Wed., 6/7 | V Girls Tennis | Tentative State Open Finals @ Yale | Away | Cancelled | Cancelled | Rain date 6/8 |
| Thu., 6/8 | V Boys Volleyball | CIAC Finals vs winner of Cheshire/E. Hartford | Away | 7:00 p.m. | ||
| Fri., 6/9 | V Baseball | Tentative CIAC Finals @ Palmer Field, Middletown | Away | Cancelled | Cancelled | or June 10th |
| Fri., 6/9 | V Softball | Tentative CIAC Finals @ DeLuca Field and West Haven | Away | Cancelled | Cancelled | or 6/10 (Rain date 6/11) |
| Sat., 6/10 | V Boys Lacrosse | CIAC Final vs Cheshire @ Brien McMahon | Away | 3:30 p.m. | Rain date 6/11 | |
| Sat., 6/10 | V Boys Lacrosse | Tentative CIAC Finals @ Brien McMahon | Away | TBA | Rain date 6/11 | |
| Sat., 6/10 | V Boys Outdoor Track | New England Championship @ Norwell HS, MA | Away | TBA | ||
| Sat., 6/10 | V Girls Lacrosse | CIAC Final vs Wilton @ Jonathan Law | Away | 11:00 a.m. | ||
| Sat., 6/10 | V Girls Outdoor Track | New England Championships @ Norwell HS, MA | Away | TBA | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Hepathlon, Steeplechase, Hammer Championships, New Britain | Away | TBA | ||
| Fri., 6/16 | V Boys Outdoor Track | New Balance Nationals Outdoor, North Carolina A&R Univ./Greensboro, NC | Away | TBA | June 16-18th | |
| Wed., 6/21 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||
| Wed., 6/21 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||