| Darien 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1160 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Ridgefield | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| TBA | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Tennis | Wilton | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | One way | |
| TBA | FR Field Hockey | Danbury | Home - DHS Baseball Varsity Field [Directions] | TBA | ||
| TBA | V Girls Ice Hockey | Greenwich Academy | Away | 3:30 p.m. | @ Chelsea Piers, Stamford - requesting Lewin & new bus | |
| TBA | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| TBA | JV Girls Tennis | Staples | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Sat., 8/25 | FR Football | Cheshire (Scrim.) | Home - DHS Stadium East Turf Field [Directions] | 3:00 p.m. | ||
| Thu., 8/30 | FR Football | Greenwich (Scrim.) | Away - GHS Field 7 [Directions] | 4:30 p.m. | TWO BUSES WILL BE NEEDED | |
| Thu., 8/30 | V Boys Soccer | St. Lukes (Scrim.) | Home - DHS Center Oval Turf [Directions] | 4:30 p.m. | ||
| Thu., 8/30 | JV Boys Soccer | St. Lukes (Scrim.) | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 8/30 | V Field Hockey | Norwalk (Scrim.) | Home - DHS Stadium Field [Directions] | 3:45 p.m. | ||
| Thu., 8/30 | JV Field Hockey | Norwalk (Scrim.) | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 8/31 | V Football | Fairfield Prep (Scrim.) | Home - DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Fri., 8/31 | V Boys Soccer | Bassick (Scrim.) | Home - DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 9/1 | SO Football | St. Anthonys (NY) (Scrim.) | Home - DHS Stadium East Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/1 | JV Football | Stepinac (NY) (Scrim.) | Away | 9:00 a.m. | 950 Mamaroneck Ave, White Plains, NY | |
| Sat., 9/1 | V Field Hockey | PlayDay @ Convent of the Sacred Heart | Away | 9:00 a.m. | 9:00 a.m. to 1:00 p.m. | |
| Sat., 9/1 | V Girls Soccer | DHS Girls Soccer Jamboree w/Mercy, Mahopac, RHAM, Berlin | Home - DHS Center Oval Turf Field [Directions] | 9:00 a.m. | will also use DHS Upper Oval Turf | |
| Sat., 9/1 | V Girls Volleyball | Darien Volleyball Play Day | Home - DHS Main Gym [Directions] | 8:00 a.m. | WILL INCLUDE NORTH & SOUTH GYMS | |
| Tue., 9/4 | V Boys Soccer | Greens Farms Academy (Scrim.) | Home - DHS Center Oval Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 9/4 | V Field Hockey | Greenwich Academy (Scrim.) | Away | 5:00 p.m. | ||
| Tue., 9/4 | V Girls Soccer | Greenwich Academy (Scrim.) | Away | 5:00 p.m. | ||
| Thu., 9/6 | V Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:30 p.m. | L 2-3 | ONE BUS FOR BOTH VAR/JV |
| Thu., 9/6 | JV Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 4:00 p.m. | ONE BUS FOR BOTH VAR/JV | |
| Thu., 9/6 | FR Girls Volleyball | Newtown | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Football | Ridgefield | Home - DHS Stadium Field [Directions] | 7:00 p.m. | W 30-6 | |
| Fri., 9/7 | V Girls Cross Country | Trumbull (Scrim.) | Away [Directions] | 4:15 p.m. | 3 buses needed, - to Long Hill Rd at Franco Gianni's Pizza | |
| Fri., 9/7 | V Field Hockey | Staples | Home - DHS Stadium Field [Directions] | 3:30 p.m. | L 1-2 | |
| Fri., 9/7 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 9/7 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:00 p.m. | 43 Lake Avenue Extension, Danbury, CT 06811 | |
| Sat., 9/8 | JV Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/8 | FR Football | Ridgefield | Away - Tiger Hollow II [Directions] | 10:30 a.m. | 55 passengers | |
| Sat., 9/8 | V Boys Soccer | Bridgeport Central | Home - DHS Center Oval Turf Field [Directions] | 2:00 p.m. | W 5-1 | |
| Sat., 9/8 | JV Boys Soccer | Bridgeport Central | Home - DHS Upper Oval Turf Field [Directions] | 2:00 p.m. | W 2-0 | |
| Sat., 9/8 | V Girls Volleyball | CIAC Tournament @ CT Sports Center | Away | 8:15 a.m. | ||
| Tue., 9/11 | V Boys Cross Country | Ridgefield, Westhill, Stamford | Away - Upper Grass Field [Directions] | 4:00 p.m. | 4 buses total for both boys & girls | |
| Tue., 9/11 | V Girls Cross Country | Ridgefield, Westhill, Stamford | Away - Upper Grass Field [Directions] | 4:00 p.m. | 4 buses total for both boys & girls | |
| Tue., 9/11 | V Field Hockey | Brien McMahon | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 9/11 | JV Field Hockey | Brien McMahon | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 9/11 | V Girls Soccer | Trumbull | Away - New Turf Field [Directions] | 5:30 p.m. | L 2-3 | |
| Tue., 9/11 | JV Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | FR Girls Soccer | Trumbull | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | SO Football | Greenwich | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Boys Soccer | Trumbull | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 9/12 | JV Boys Soccer | Trumbull | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | L 1-5 | |
| Wed., 9/12 | FR Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | T 0-0 | |
| Wed., 9/12 | FR Field Hockey | Greenwich Academy | Away | 4:00 p.m. | ||
| Wed., 9/12 | V Girls Swimming and Diving | St. Joseph | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:55 p.m. ONE WAY | |
| Thu., 9/13 | FR Football | Brien McMahon | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Greenwich | Home - DHS Center Oval Turf Field [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 9/13 | JV Girls Soccer | Greenwich | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/13 | FR Girls Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | Sound Shore Dr, Cos Cob, CT | |
| Thu., 9/13 | V Girls Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/13 | JV Girls Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/13 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 35-0 | 2 buses needed |
| Fri., 9/14 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 9/14 | JV Boys Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 9/14 | FR Boys Soccer | Greenwich | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 9/14 | V Sideline Cheerleading | Brien McMahon | Away [Directions] | 7:00 p.m. | 12 passengers | |
| Fri., 9/14 | V Field Hockey | Fairfield Warde | Away - Tomlinson MS [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 9/14 | JV Field Hockey | Fairfield Warde | Away - Tomlinson MS [Directions] | 5:30 p.m. | ||
| Fri., 9/14 | V Girls Volleyball | Bridgeport Central | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/14 | JV Girls Volleyball | Bridgeport Central | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Sat., 9/15 | V Boys Cross Country | Wilton Invitationals @ Allens Meadows | Away | 9:30 a.m. | THREE buses total for both boys & girls | |
| Sat., 9/15 | JV Football | Brien McMahon | Home - DHS Stadium East Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 9/15 | V Girls Cross Country | Wilton Invitational | Away | 9:30 a.m. | THREE buses total for both boys & girls | |
| Sat., 9/15 | V Field Hockey | Garden City (NY) | Home - DHS Stadium Field [Directions] | 11:00 a.m. | L 1-3 | |
| Sat., 9/15 | JV Field Hockey | Garden City (NY) | Home - DHS Stadium Field [Directions] | 12:30 p.m. | ||
| Sat., 9/15 | V Girls Soccer | Trinity Catholic | Home - DHS Center Oval Turf Field [Directions] | 10:00 a.m. | W 6-0 | |
| Mon., 9/17 | V Boys Cross Country | Fairfield Ludlowe, Danbury, Trinity Catholic | Away - Taft Field [Directions] | 4:00 p.m. | 3 buses total for both boys & girls | |
| Mon., 9/17 | V Boys Soccer | Trinity Catholic | Away | 4:00 p.m. | W 4-0 | |
| Mon., 9/17 | V Girls Cross Country | Fairfield Ludlowe, Danbury, Trinity Catholic | Away - Taft Field [Directions] | 4:00 p.m. | 3 buses total for both boys & girls | |
| Mon., 9/17 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 9-0 | |
| Mon., 9/17 | JV Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | V Girls Swimming and Diving | Trumbull | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:55 p.m. ONE WAY | |
| Mon., 9/17 | V Girls Volleyball | Trumbull | Home - DHS Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 9/17 | JV Girls Volleyball | Trumbull | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | FR Football | St. Joseph | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 11-1 | |
| Thu., 9/20 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Thu., 9/20 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:30 p.m. | T 1-1 | |
| Thu., 9/20 | JV Girls Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Boys Soccer | Brien McMahon | Home - DHS Stadium Field [Directions] | 7:00 p.m. | L 1-3 | |
| Fri., 9/21 | JV Boys Soccer | Brien McMahon | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | L 2-6 | |
| Fri., 9/21 | FR Boys Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 9/21 | JV Field Hockey | Greenwich Academy | Away | 4:00 p.m. | ||
| Fri., 9/21 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:30 p.m. | L 2-3 | One bus for Varsity & JV |
| Fri., 9/21 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | One bus for Varsity & JV | |
| Fri., 9/21 | FR Girls Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/22 | V Football | St. Joseph | Away - St. Joseph HS [Directions] | 1:30 p.m. | W 22-7 | 54 passenger |
| Sat., 9/22 | V Sideline Cheerleading | St. Joseph | Away [Directions] | 1:30 p.m. | 12 passengers | |
| Sat., 9/22 | V Girls Cross Country | Ocean State Invite, Goddard Park, RI | Away | 2:35 p.m. | Overnight Trip | |
| Sat., 9/22 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 11:00 a.m. | W 4-0 | Combining Varsity & JV |
| Sat., 9/22 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 11:00 a.m. | Combining Varsity & JV | |
| Sat., 9/22 | FR Girls Soccer | Danbury | Home - DHS Upper Oval Turf Field [Directions] | 9:45 a.m. | ||
| Mon., 9/24 | JV Football | St. Joseph | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | V Boys Soccer | Danbury | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Mon., 9/24 | JV Boys Soccer | Danbury | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 9/24 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 9/24 | V Girls Swimming and Diving | Ridgefield | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:55 p.m. ONE WAY | |
| Mon., 9/24 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | W 3-0 | One bus for Varsity & JV |
| Mon., 9/24 | JV Girls Volleyball | Trinity Catholic | Away | 4:00 p.m. | One bus for Varsity & JV | |
| Wed., 9/26 | FR Football | Stamford | Away [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 9/26 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | FR Boys Soccer | Stamford | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 9/26 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 7:00 p.m. | Warmups @ 6:30 p.m. | |
| Wed., 9/26 | V Girls Volleyball | Brien McMahon | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/26 | JV Girls Volleyball | Brien McMahon | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/27 | V Boys Cross Country | Trumbull, Brien McMahon, Greenwich | Away - Greenwich Point [Directions] | 4:00 p.m. | 4 buses total for both boys & girls | |
| Thu., 9/27 | V Girls Cross Country | Trumbull, Brien McMahon, Greenwich | Away - Greenwich Point [Directions] | 4:00 p.m. | 4 buses total for both boys & girls | |
| Thu., 9/27 | V Field Hockey | Daniel Hand | Home - DHS Stadium Field [Directions] | 5:30 p.m. | W 6-2 | |
| Thu., 9/27 | JV Field Hockey | Daniel Hand | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Soccer | Wilton | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/27 | JV Girls Soccer | Wilton | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/27 | FR Girls Soccer | Wilton | Away [Directions] | 4:00 p.m. | ||
| Fri., 9/28 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 9/28 | JV Boys Soccer | Wilton | Away [Directions] | 4:00 p.m. | ||
| Fri., 9/28 | FR Boys Soccer | Wilton | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/28 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | Cancelled | Cancelled | |
| Fri., 9/28 | V Girls Volleyball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/28 | JV Girls Volleyball | Danbury | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/28 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Sat., 9/29 | V Football | Stamford | Home - DHS Stadium Field [Directions] | 1:30 p.m. | W 42-7 | |
| Sat., 9/29 | V Sideline Cheerleading | Stamford | Home - DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 9/29 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 11:00 a.m. | W 6-0 | |
| Sat., 9/29 | JV Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 9/29 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 2-0 | |
| Sat., 9/29 | JV Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 1:00 p.m. | ||
| Sat., 9/29 | FR Girls Soccer | Ridgefield | Home - DHS Upper Oval Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 10/1 | JV Football | Stamford | Away [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | V Boys Soccer | Ridgefield | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/1 | JV Boys Soccer | Ridgefield | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | FR Boys Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 10/1 | V Field Hockey | Trumbull | Home - DHS Stadium Field [Directions] | 5:45 p.m. | W 6-0 | |
| Mon., 10/1 | JV Field Hockey | Trumbull | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | FR Field Hockey | Trumbull | Home - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | ||
| Mon., 10/1 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 3-1 | One bus for Varsity & JV |
| Mon., 10/1 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | One bus for Varsity & JV | |
| Mon., 10/1 | FR Girls Volleyball | Stamford | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Boys Cross Country | New Canaan, Wilton, Fairfield Warde | Away - Waveny Park [Directions] | 4:00 p.m. | 3 buses total for both boys & girls | |
| Tue., 10/2 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 10/2 | FR Field Hockey | Fairfield Ludlowe | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | W 3-2 | VARSITY & JV COMBININE ON ONE BUS |
| Tue., 10/2 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | VARSITY & JV COMBINING ON ONE BUS | |
| Tue., 10/2 | FR Girls Soccer | Fairfield Warde | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | JV Field Hockey | Staples | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Soccer | Stamford | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 10/3 | JV Girls Soccer | Stamford | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 10/3 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | One bus for Varsity & JV |
| Wed., 10/3 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | One bus for Varsity & JV | |
| Wed., 10/3 | FR Girls Volleyball | Wilton | Home - DHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/4 | FR Football | Staples | Away - Staples Stadium [Directions] | 6:15 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Fairfield Warde | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 10/4 | JV Boys Soccer | Fairfield Warde | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 10/4 | V Field Hockey | Greenwich | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 7-2 | |
| Thu., 10/4 | JV Field Hockey | Greenwich | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 10/5 | V Girls Cross Country | New Canaan, Wilton, Fairfield Warde | Away - Waveny Park [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | FR Field Hockey | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | V Girls Soccer | Fairfield Ludlowe | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 10/5 | JV Girls Soccer | Fairfield Ludlowe | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/5 | JV Girls Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/5 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/6 | V Boys Cross Country | Wickham Park Invitational, Manchester, CT | Away | TBA | No bus needed | |
| Sat., 10/6 | V Football | Staples | Home - DHS Stadium Field [Directions] | 2:00 p.m. | W 24-0 | |
| Sat., 10/6 | V Sideline Cheerleading | Staples | Home - DHS Stadium Field [Directions] | 2:00 p.m. | ||
| Mon., 10/8 | SO Football | Greenwich | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/8 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | W 2-1 | |
| Mon., 10/8 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Mon., 10/8 | FR Boys Soccer | Fairfield Ludlowe | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | T 2-2 | |
| Mon., 10/8 | V Field Hockey | New Canaan | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 10/8 | JV Field Hockey | New Canaan | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 10/8 | FR Field Hockey | New Canaan | Away - WTT2 [Directions] | 4:00 p.m. | ||
| Mon., 10/8 | V Girls Volleyball | Newtown | Home - DHS Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 10/8 | JV Girls Volleyball | Newtown | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/8 | FR Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Cross Country | Staples, St. Joseph, Norwalk | Away - Staples Stadium [Directions] | 4:00 p.m. | 3 buses total for both boys & girls | |
| Tue., 10/9 | V Girls Cross Country | Staples, St. Joseph, Norwalk | Away - Staples Stadium [Directions] | 4:00 p.m. | 3 buses total for both boys & girls | |
| Tue., 10/9 | V Girls Soccer | New Canaan | Home - DHS Stadium Field [Directions] | 5:30 p.m. | L 1-0 | |
| Tue., 10/9 | JV Girls Soccer | New Canaan | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | FR Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:30 p.m. | ||
| Wed., 10/10 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/10 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | FR Boys Soccer | New Canaan | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/10 | V Field Hockey | Westhill | Away - Westhill Stadium [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 10/10 | JV Field Hockey | Westhill | Away - Westhill Football Field [Directions] | 5:30 p.m. | ||
| Wed., 10/10 | V Girls Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:55 p.m. - No bus | |
| Wed., 10/10 | V Girls Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Wed., 10/10 | JV Girls Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/10 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 10 passengers | |
| Thu., 10/11 | V Girls Swimming and Diving | Westhill/Stamford | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:55 p.m.- no bus | |
| Fri., 10/12 | JV Boys Soccer | Staples | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Field Hockey | Norwalk | Home - DHS Stadium Field [Directions] | 7:00 p.m. | W 5-2 | |
| Fri., 10/12 | JV Field Hockey | Norwalk | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 10/12 | FR Field Hockey | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Fri., 10/12 | V Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 3-1 | |
| Fri., 10/12 | JV Girls Soccer | Staples | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-2 | One bus for Varsity & JV |
| Fri., 10/12 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | One bus for Varsity & JV | |
| Fri., 10/12 | FR Girls Volleyball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/13 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | T 0-0 | |
| Sat., 10/13 | FR Boys Soccer | Greenwich Country Day | Away | 10:30 a.m. | W 2-1 | |
| Sat., 10/13 | FR Field Hockey | Greenwich Country Day | Away | Cancelled | Cancelled | |
| Mon., 10/15 | JV Boys Soccer | Wright Tech | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:45 p.m. | T 0-0 | |
| Mon., 10/15 | JV Field Hockey | Greenwich Academy | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | One bus for Varsity & JV |
| Mon., 10/15 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | One bus for Varsity & JV | |
| Mon., 10/15 | FR Girls Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-2 | |
| Tue., 10/16 | JV Girls Soccer | Westhill | Away - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | FR Girls Soccer | Staples | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | Early dismissal at 2:00 p.m. | |
| Wed., 10/17 | FR Boys Soccer | Westhill | Away - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/17 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 6:30 p.m. | W 6-2 | |
| Wed., 10/17 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:00 p.m. | ||
| Wed., 10/17 | FR Field Hockey | Wilton | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Girls Volleyball | Staples | Home - DHS Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 10/17 | JV Girls Volleyball | Staples | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/17 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Boys Cross Country | FCIAC Championship @ Waveny Park, New Canaan | Away | 2:15 p.m. | 3 buses total for both boys & girls | |
| Thu., 10/18 | FR Football | Fairfield Warde | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Westhill | Home - DHS Stadium Field [Directions] | 5:30 p.m. | L 1-4 | |
| Thu., 10/18 | JV Boys Soccer | Westhill | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Girls Cross Country | FCIAC Tourney @ Waveny Park, New Canaan | Away | 2:15 p.m. | 3 buses total for both boys & girls | |
| Thu., 10/18 | FR Field Hockey | Westhill | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | Early dismiss @ 2:00 p.m. | |
| Fri., 10/19 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | W 42-7 | |
| Fri., 10/19 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:15 p.m. | W 4-0 | |
| Fri., 10/19 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:15 p.m. | ||
| Fri., 10/19 | V Sideline Cheerleading | Fairfield Warde | Away [Directions] | 6:00 p.m. | 12 passengers | |
| Fri., 10/19 | V Field Hockey | Ridgefield | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 10/19 | JV Field Hockey | Ridgefield | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 10/19 | FR Field Hockey | Ridgefield | Away - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Girls Soccer | St. Joseph | Home - DHS Center Oval Turf Field [Directions] | 4:15 p.m. | T 1-1 | |
| Fri., 10/19 | JV Girls Soccer | St. Joseph | Home - DHS Upper Oval Turf Field [Directions] | 4:15 p.m. | ||
| Sat., 10/20 | JV Football | Fairfield Warde | Home - DHS Stadium Field [Directions] | Cancelled | Cancelled | |
| Sat., 10/20 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 8:30 a.m. | ||
| Mon., 10/22 | SO Football | Norwalk | Away [Directions] | 5:30 p.m. | @ Nathan Hale MS | |
| Mon., 10/22 | V Girls Soccer | Norwalk | Home - DHS Stadium Field [Directions] | 5:30 p.m. | W 5-1 | |
| Mon., 10/22 | JV Girls Soccer | Norwalk | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Volleyball | Westhill | Home - DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/22 | JV Girls Volleyball | Westhill | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/22 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:15 p.m. | T 1-1 | |
| Tue., 10/23 | JV Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | FR Boys Soccer | Norwalk | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | FR Field Hockey | Greenwich Academy | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | W 3-1 | One bus for Varsity & JV |
| Wed., 10/24 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | One bus for Varsity & JV | |
| Wed., 10/24 | FR Girls Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/25 | FR Football | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | ||
| Thu., 10/25 | FR Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/25 | V Girls Cross Country | Freshman Two-Mile Race in Danbury/Tarrywile Park | Away | 4:15 p.m. | Freshmen only (25 passengers) | |
| Thu., 10/25 | V Girls Soccer | FCIAC Quarterfinal @ Staples HS | Away | 3:00 p.m. | Early dismiss @ 1:15 p.m. | |
| Thu., 10/25 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University [Directions] | 4:00 p.m. | Early dismiss @ 2:00 p.m. | |
| Thu., 10/25 | V Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:30 p.m. | W 3-0 | One bus for Varsity & JV |
| Thu., 10/25 | JV Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:00 p.m. | One bus for Varsity & JV | |
| Fri., 10/26 | V Boys Cross Country | CIAC Class L Championship @ Wickham Park, Manchester, CT | Away | 9:15 a.m. | 1 bus needed for Boys & Girls - full day early dismissal | |
| Fri., 10/26 | V Football | Trumbull | Home - DHS Stadium Field [Directions] | 7:00 p.m. | W 42-13 | |
| Fri., 10/26 | V Sideline Cheerleading | Trumbull | Home - DHS Stadium Field [Directions] | 7:00 p.m. | ||
| Fri., 10/26 | V Girls Cross Country | CIAC State Class L Meet at Wickham Park | Away | 9:45 a.m. | 1 bus for both Boys/Girls & full day early dismissal | |
| Fri., 10/26 | V Field Hockey | FCIAC Quarterfinals vs Ridgefield | Home - DHS Stadium Field [Directions] | 3:30 p.m. | Early dismiss @ 2:00 p.m. | |
| Sat., 10/27 | JV Girls Swimming and Diving | JV FCIACS @ Greenwich HS | Away | 2:30 p.m. | ||
| Sat., 10/27 | FR Girls Volleyball | Southington HS Freshman Volleyball Playday | Away | 9:00 a.m. | ||
| Mon., 10/29 | JV Football | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | 53 passengers | |
| Mon., 10/29 | V Field Hockey | FCIAC Semi-final vs Greenwich @ McMahon | Away | 7:30 p.m. | Games at 6:00 p.m. & 7:30 p.m. | |
| Mon., 10/29 | V Girls Soccer | FCIAC Semi-final vs New Canaan @ Wilton | Away | 7:00 p.m. | ||
| Mon., 10/29 | V Girls Swimming and Diving | FCIAC Diving Championships @ Westhill | Away | 5:00 p.m. | Early dismiss @ 1:50 p.m. | |
| Tue., 10/30 | V Girls Swimming and Diving | FCIAC Swim Trials @ Greenwich HS | Away | 5:30 p.m. | ||
| Tue., 10/30 | V Girls Volleyball | FCIAC Quarterfinal @ Greenwich | Away | 4:30 p.m. | ||
| Thu., 11/1 | V Boys Cross Country | CIAC State Open Championships @ Wickham Park, Manchester, CT | Away | 2:00 p.m. | Early dismiss @ 11:00 a.m. - no bus | |
| Thu., 11/1 | FR Football | Wilton | Home - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 11/1 | V Girls Cross Country | CIAC State Open at Wickham Park | Away | 2:45 p.m. | Early dismiss @ 11:30 a.m. - No bus | |
| Thu., 11/1 | V Field Hockey | FCIAC Final vs Staples @ McMahon | Away | 7:00 p.m. | ||
| Thu., 11/1 | V Girls Soccer | Tentative FCIAC Final @ Fairfield Warde | Away | Cancelled | Cancelled | |
| Thu., 11/1 | V Girls Swimming and Diving | FCIAC Swim Finals @ Greenwich | Away | 6:30 p.m. | ||
| Thu., 11/1 | V Girls Volleyball | FCIAC Semi-Finals vs Westhill @ Fairfield Ludlowe | Away | 5:00 p.m. | ||
| Fri., 11/2 | V Football | Wilton | Away - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 34-13 | 2 buses needed |
| Fri., 11/2 | V Sideline Cheerleading | Wilton | Away [Directions] | 7:00 p.m. | 12 passengers | |
| Sat., 11/3 | JV Football | Wilton | Home [Directions] | 2:00 p.m. | ||
| Sat., 11/3 | V Girls Volleyball | Tentative FCIAC Final @ Fairfield Ludlowe | Away | Cancelled | Cancelled | |
| Mon., 11/5 | V Girls Soccer | CIAC - Round 1 @ Brien McMahon | Away | 6:30 p.m. | ||
| Mon., 11/5 | V Girls Volleyball | CIAC - Round 1 vs Jonathan Hall | Home - DHS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 11/6 | V Boys Soccer | CIAC Round 1 @ Staples'@ Bedford MS | Away | 2:00 p.m. | ||
| Wed., 11/7 | FR Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Wed., 11/7 | V Field Hockey | CIAC - Round 1 vs New Canaan | Home - DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Wed., 11/7 | V Girls Soccer | Suffield | Away - Ted Beneski Turf Field [Directions] | 2:00 p.m. | W 1-0 | Early dismissal @ 10:45 a.m. |
| Thu., 11/8 | V Boys Soccer | Tentative CIAC - Round 2 @ higher ranked | Away | Cancelled | Cancelled | |
| Thu., 11/8 | V Girls Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | Early dismiss @ 1:30 p.m. One way - small bus | |
| Thu., 11/8 | V Girls Volleyball | CIAC - Round 2 @ Newtown | Away | 5:00 p.m. | ||
| Fri., 11/9 | V Field Hockey | CIAC - Quarterfinal @ Hall HS, West Hartford | Away | 4:00 p.m. | Early dismiss @ 12:10 p.m. | |
| Fri., 11/9 | V Girls Soccer | CIAC Quarterfinal @ Ridgefield | Away | 4:00 p.m. | Early dismiss @ 1:45 p.m. | |
| Sat., 11/10 | V Boys Cross Country | New England Championships @ Derryfield Park, Manchester, NH | Away | Cancelled | Cancelled | |
| Sat., 11/10 | V Football | Bridgeport Central | Home - DHS Stadium Field [Directions] | 1:30 p.m. | W 45-8 | |
| Sat., 11/10 | V Boys Soccer | Tentative CIAC - Quarterfinal @ higher ranked | Away | Cancelled | Cancelled | |
| Sat., 11/10 | V Sideline Cheerleading | Bridgeport Central | Home - DHS Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 11/10 | V Girls Cross Country | New England Meet in New Hampshire | Away | TBA | If we qualify from 11/2 | |
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 3:15 p.m. | ||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC States for Girls Swim @ Cornerstone Aquatics, W. Hartford | Away | 3:15 p.m. | Warm-ups @ 2:00 p.m./55 Buena Vista Rd, West Hartford | |
| Sat., 11/10 | V Girls Volleyball | CIAC - Quarterfinal vs Glastonbury | Home - DHS Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 11/12 | JV Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Tue., 11/13 | V Field Hockey | CIAC Semi-Final vs Staples @ Brien McMahon | Away | 6:00 p.m. | ||
| Tue., 11/13 | V Girls Swimming and Diving | CIAC Class L Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Tue., 11/13 | V Girls Swimming and Diving | CIAC Girls Swim Finals @ SCSU in New Haven | Away | 6:00 p.m. | Warm ups @ 5:00 p.m./125 Wintergreen Ave. | |
| Wed., 11/14 | V Girls Volleyball | CIAC Semi Final vs Southington @ Shelton HS | Away | 6:00 p.m. | ||
| Fri., 11/16 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | 1:30 p.m. early dismissal -Small bus - one way | |
| Sat., 11/17 | V Boys Soccer | Tentative CIAC Final | Away | Cancelled | Cancelled | |
| Sat., 11/17 | V Field Hockey | Tentative CIAC Final @ Wethersfield | Away | Cancelled | Cancelled | |
| Sat., 11/17 | V Girls Soccer | Tentative CIAC Final | Away | Cancelled | Cancelled | |
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Sat., 11/17 | V Girls Swimming and Diving | State Open @ Yale Kiphuth Pool/Payne Whitney Gym | Away | 12:00 p.m. | 10:00 a.m. warm-ups / 70 Tower Pkwy, New Haven, CT | |
| Sat., 11/17 | V Girls Volleyball | CIAC Final vs Amity @ East Haven | Away | 10:00 a.m. | ||
| Mon., 11/19 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 11/20 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/22 | V Football | New Canaan | Away - Boyle Stadium [Directions] | 10:30 a.m. | L 14-17 | School buses cancelled per Chris |
| Thu., 11/22 | V Sideline Cheerleading | Turkey Bowl vs New Canaan @ Boyle Stadium, Stamford | Away | 10:30 a.m. | 12 passengers | |
| Tue., 11/27 | V Football | CIAC Tourney Quarterfinals @ Newtown | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/27 | V Sideline Cheerleading | CIAC Quarterfinal Football @ Newtown HS | Away | 6:30 p.m. | ||
| Sat., 12/1 | V Girls Ice Hockey | Shelton Jamboree- Rinks @ Shelton | Away | 7:00 p.m. | ||
| Sun., 12/2 | V Football | CIAC Tourney Semifinals | Away - Higher Seed | Cancelled | Cancelled | |
| Mon., 12/3 | V Boys Ice Hockey | St. Lukes (Scrim.) | Home - SoNo Ice House [Directions] | 3:15 p.m. | ||
| Mon., 12/3 | V Boys Squash | Brunswick School | Away | 4:00 p.m. | ||
| Mon., 12/3 | V Girls Basketball | Weston (Scrim.) | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/3 | JV Girls Basketball | Weston (Scrim.) | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 12/4 | JV Girls Squash | Rye (NY) | Home - Chelsea Piers, Stamford [Directions] | 7:55 p.m. | ||
| Wed., 12/5 | V Boys Squash | New Canaan | Home - Chelsea Piers, Stamford [Directions] | 8:20 p.m. | ||
| Wed., 12/5 | JV Boys Squash | Briarcliff (NY) | Away | 8:00 p.m. | @ Life Time Athletic, Harrison, NY | |
| Wed., 12/5 | V Girls Ice Hockey | Hamden Coop | Home - Darien Ice Rink [Directions] | 5:50 p.m. | W 9-1 | |
| Thu., 12/6 | V Boys Basketball | Immaculate (Scrim.) | Away - Immaculate [Directions] | 6:30 p.m. | ||
| Sat., 12/8 | V Boys Basketball | Hoops for Food Jamboree @ Windsor HS | Away | 1:30 p.m. | ||
| Sat., 12/8 | V Football | CIAC Tourney Final | Away - Site TBA | Cancelled | Cancelled | |
| Sat., 12/8 | V Boys Ice Hockey | St. Johns Prep (MA) (Scrim.) | Home - Darien Ice Rink [Directions] | 3:50 p.m. | ||
| Sat., 12/8 | V Boys Squash | Bronxville (NY) | Away | 10:00 a.m. | @ Yale, New Haven - 1 bus total for all Squash teams | |
| Sat., 12/8 | JV Boys Squash | New Haven/Bronxville @ Yale, New Haven, CT | Away | 10:00 a.m. | 1 bus total for all Squash teams | |
| Sat., 12/8 | V Boys Swimming and Diving | Norwalk Relays | Away | 3:00 p.m. | Warm-ups @ 2:15 p.m. | |
| Sat., 12/8 | V Girls Squash | New Canaan | Away [Directions] | 11:20 a.m. | 1 bus total for all squash team to Yale, New Haven | |
| Sat., 12/8 | JV Girls Squash | New Haven @ Yale, New Haven | Away | 11:20 a.m. | 1 bus total for all squash teams | |
| Sun., 12/9 | V Boys Ice Hockey | St. Johns-Shrewsbury (MA) (Scrim.) | Away | 1:30 p.m. | @ New England Sports Center | |
| Mon., 12/10 | JV Boys Ice Hockey | Trumbull | Home - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Mon., 12/10 | V Boys Squash | St. Lukes | Away | 5:15 p.m. | ||
| Mon., 12/10 | JV Boys Squash | St. Lukes | Away | 4:15 p.m. | 1 bus Varsity & JV Boys | |
| Mon., 12/10 | V Girls Basketball | Kolbe Cathedral | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 23-41 | |
| Mon., 12/10 | JV Girls Basketball | Kolbe Cathedral | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/10 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 8:40 p.m. | W 8-0 | |
| Tue., 12/11 | V Girls Squash | Staples | Away [Directions] | 8:15 p.m. | @ Intensity, Norwalk, CT | |
| Tue., 12/11 | JV Girls Squash | Rye (NY) | Away | 8:00 p.m. | @ Life Time Athletic, Harrison, NY | |
| Wed., 12/12 | V Boys Ice Hockey | LaSalle Academy (RI) | Home - Stamford Twin Rinks [Directions] | 5:00 p.m. | L 2-3(OT) | |
| Wed., 12/12 | V Boys Squash | Rye (NY) | Away | 7:30 p.m. | @ MSquash, Port Chester, NY | |
| Wed., 12/12 | V Wrestling | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/12 | V Girls Squash | Greenwich | Home - Chelsea Piers, Stamford [Directions] | 8:30 p.m. | ||
| Fri., 12/14 | V Boys Squash | Choate Rosemary Hall | Away | 4:00 p.m. | Choate, Wallingford, CT | |
| Fri., 12/14 | V Girls Basketball | Norwalk | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 40-68 | |
| Fri., 12/14 | JV Girls Basketball | Norwalk | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/14 | V Girls Squash | Choate Rosemary Hall | Away | 5:30 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Hamden | Home - Darien Ice Rink [Directions] | 6:00 p.m. | W 3-1 | |
| Sat., 12/15 | JV Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 7:30 p.m. | ||
| Sat., 12/15 | V Boys Indoor Track | Wilton, New Canaan, Danbury, Brien McMahon | Away [Directions] | 9:30 a.m. | 1 bus needed for Boys | |
| Sat., 12/15 | V Wrestling | Oxford HS Invitational Tourney | Away | 9:30 a.m. | Weigh-ins @ 7:30-8:30 a.m. | |
| Sat., 12/15 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice Rink [Directions] | 8:10 p.m. | W 8-1 | |
| Sat., 12/15 | V Girls Indoor Track | Wilton, New Canaan, Danbury, Brien McMahon | Away [Directions] | 9:30 a.m. | @ Wilton - Two buses needed | |
| Mon., 12/17 | V Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 7:00 p.m. | W 70-66 | 1 bus Varsity/JV |
| Mon., 12/17 | JV Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:15 p.m. | 1 bus Varsity/JV | |
| Mon., 12/17 | FR Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 12/17 | JV Boys Ice Hockey | Greenwich | Home - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Mon., 12/17 | V Boys Swimming and Diving | Greenwich | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:50 p.m. - one way | |
| Mon., 12/17 | V Girls Basketball | Bethel | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 34-49 | |
| Mon., 12/17 | JV Girls Basketball | Bethel | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/17 | V Girls Ice Hockey | New Canaan | Home - Darien Ice Rink [Directions] | 7:10 p.m. | L 0-3 | |
| Tue., 12/18 | V Girls Squash | Rye (NY) | Away | 8:00 p.m. | @ Life Time Athletic, Harrison, NY | |
| Wed., 12/19 | V Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 57-61 | |
| Wed., 12/19 | JV Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | FR Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice Rink [Directions] | 8:00 p.m. | W 2-1 | |
| Wed., 12/19 | JV Boys Squash | Staples | Away [Directions] | 7:30 p.m. | @ Intensity, Norwalk, CT | |
| Wed., 12/19 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Pat Spinola Natatorium [Directions] | 3:30 p.m. | Early dismiss @ 1:50 p.m. | |
| Wed., 12/19 | V Wrestling | Trumbull | Home - DHS - South Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/19 | V Competitive Cheerleading | Bridgeport Central | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/19 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 69-25 | 1 bus Varsity/JV |
| Wed., 12/19 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 1 bus Varsity/JV | |
| Thu., 12/20 | JV Boys Ice Hockey | ND Christmas Tournament @ Rinks @ Shelton | Away | 8:20 p.m. | ||
| Fri., 12/21 | V Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 5:00 p.m. | L 53-72 | |
| Fri., 12/21 | JV Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 2:00 p.m. | ||
| Fri., 12/21 | JV Boys Ice Hockey | ND Christmas Tournament 6:30 or 8:15 Rinks @ Shelton | Away | TBA | ||
| Fri., 12/21 | V Competitive Cheerleading | Trumbull | Home - DHS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 12/21 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:00 p.m. | L 29-45 | 1 bus Varsity/JV |
| Fri., 12/21 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 3:30 p.m. | 1 bus Varsity/JV | |
| Fri., 12/21 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 2:00 p.m. | L 27-31 | |
| Fri., 12/21 | V Girls Ice Hockey | Morristown-Beard (NJ) | Away | 3:15 p.m. | L 1-3 | @ Twin Oaks Rink 65 Columbia Rd, Morristown, NJ |
| Sat., 12/22 | V Boys Indoor Track | Hillhouse HS, New Haven, CT | Away | 10:00 a.m. | No bus needed | |
| Sat., 12/22 | V Boys Indoor Track | Reindeer Relays @ Wilton HS | Away | 9:30 a.m. | 2 buses total for both boys & girls | |
| Sat., 12/22 | V Wrestling | Ridgefield, Stamford, Norwalk, John Jay (NY) | Away - RHS Main and Aux Gyms [Directions] | 10:00 a.m. | @ Ridgefield | |
| Sat., 12/22 | V Girls Indoor Track | Wilton Reindeer Relays | Away | 9:30 a.m. | 2 buses total for both boys & girls | |
| Mon., 12/24 | JV Boys Ice Hockey | Tourney Consolation (if lose 12/20) 9am or 10:45 Rinks @ Shelton | Away | TBA | ||
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invitational @ Hillhouse HS, New Haven | Away | 12:00 p.m. | 1 bus for boys | |
| Fri., 12/28 | V Boys Basketball | Bethel | Away - Bethel HS [Directions] | 7:00 p.m. | W 51-50 | |
| Fri., 12/28 | JV Boys Basketball | Bethel | Away - Bethel HS [Directions] | 5:00 p.m. | ||
| Sat., 12/29 | V Boys Basketball | Weston | Home - DHS Main Gym [Directions] | 5:00 p.m. | W 52-46 | |
| Sat., 12/29 | JV Boys Basketball | Weston | Home - DHS Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/29 | V Boys Ice Hockey | Greenwich | Away - Greenwich Skating Club [Directions] | 4:00 p.m. | L 0-3 | |
| Sat., 12/29 | JV Boys Ice Hockey | Christmas Tournament Finals 9am Rinks @ Shelton | Away | TBA | ||
| Sat., 12/29 | V Wrestling | Danbury Holiday Invitational | Away | 9:00 a.m. | ||
| Sat., 12/29 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 2:00 p.m. | W 43-42(4OT) | |
| Wed., 1/2 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | 6:00 p.m. | W 6-4 | |
| Wed., 1/2 | JV Boys Squash | Rye (NY) | Away | 7:30 p.m. | @ MSquash, Port Chester, NY | |
| Thu., 1/3 | V Wrestling | Wilton | Home - DHS - South Gym [Directions] | 5:00 p.m. | ||
| Thu., 1/3 | V Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 50-34 | |
| Thu., 1/3 | JV Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/3 | FR Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/3 | V Girls Gymnastics | Fairfield Warde, Fairfield Ludlowe | Away - GCA [Directions] | 6:30 p.m. | Darien: 119 Ludlowe: 130 Warde: 126.4 | PICKUP @ DARIEN YMCA - 85 Mill Plain Rd Fairfield |
| Fri., 1/4 | V Boys Basketball | Greenwich | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 51-67 | GOING TO BRIEN MCMAHON HS |
| Fri., 1/4 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Sat., 1/5 | JV Boys Basketball | Greenwich | Away - Central MS [Directions] | 10:30 a.m. | ||
| Sat., 1/5 | FR Boys Basketball | Greenwich | Away - Central MS [Directions] | 9:00 a.m. | ||
| Sat., 1/5 | V Boys Ice Hockey | Xavier | Home - Darien Ice Rink [Directions] | 3:50 p.m. | W 4-3 | |
| Sat., 1/5 | V Boys Indoor Track | Wilton, New Canaan, Fairfield Ludlowe, Ridgefield | Away [Directions] | 9:30 a.m. | @ Wilton - 2 buses total for both boys & girls | |
| Sat., 1/5 | V Wrestling | Somers (NY) Tournament | Away | 9:00 a.m. | ||
| Sat., 1/5 | V Girls Basketball | St. Joseph | Home - DHS Main Gym [Directions] | 1:00 p.m. | L 47-58 | |
| Sat., 1/5 | JV Girls Basketball | St. Joseph | Home - DHS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 1/5 | FR Girls Basketball | St. Joseph | Home - DHS Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 1/5 | V Girls Gymnastics | Pomperaug Invitational | Away | 10:00 a.m. | 7th place: 123.1 | PICKUP AT DARIEN YMCA |
| Sat., 1/5 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms CC [Directions] | 12:30 p.m. | L 2-3 | @ ISCC - requesting new bus and driver Lewin |
| Sat., 1/5 | V Girls Indoor Track | Wilton, New Canaan, Fairfield Ludlowe, Ridgefield | Away [Directions] | 9:30 a.m. | @ Wilton -Two buses total for both boys and girls | |
| Sat., 1/5 | V Girls Indoor Track | 3rd James Barber Invitational @ Southern CT State University/Moore Field House & Hillhouse HS - Elm City | Away | 12:00 p.m. | 2nd Stop will be at Hillhouse HS (no return) | |
| Mon., 1/7 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | L 51-55 | 1 bus for Var/JV |
| Mon., 1/7 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | 1 bus for Var/JV | |
| Mon., 1/7 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Mon., 1/7 | JV Boys Ice Hockey | Ridgefield | Home - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Mon., 1/7 | V Boys Squash | Hopkins School | Away | 4:00 p.m. | Hopkins School, New Haven. CT | |
| Mon., 1/7 | JV Boys Squash | Hopkins School | Away | 4:00 p.m. | 1 bus Varsity & JV Boys | |
| Mon., 1/7 | V Girls Basketball | Trinity Catholic | Home - DHS Main Gym [Directions] | 5:30 p.m. | L 39-58 | |
| Mon., 1/7 | JV Girls Basketball | Trinity Catholic | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/8 | V Girls Squash | Briarcliff (NY) | Away | 8:00 p.m. | @ Life Time Athletic, Harrison, NY | |
| Wed., 1/9 | V Boys Squash | Greenwich | Away [Directions] | 4:00 p.m. | @ MSquash, Port Chester, NY | |
| Wed., 1/9 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | early dismiss @ 2:00 p.m. | |
| Wed., 1/9 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice Rink [Directions] | 6:00 p.m. | W 8-0 | |
| Thu., 1/10 | V Boys Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 81-77 | |
| Thu., 1/10 | JV Boys Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/10 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | early dismiss @ 2:05 p.m. | |
| Thu., 1/10 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | Early dismiss @ 1:30 p.m. | |
| Thu., 1/10 | V Competitive Cheerleading | Brien McMahon | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/10 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 55-26 | 1 bus Varsity/JV |
| Thu., 1/10 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 1 bus Varsity/JV | |
| Fri., 1/11 | FR Boys Basketball | Greenwich Country Day | Away | 6:00 p.m. | ||
| Fri., 1/11 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 5:20 p.m. | L 2-3(OT) | |
| Fri., 1/11 | V Boys Indoor Track | Yale Invitational, Coxe Cage, New Haven | Away | 1:00 p.m. | 10:50 a.m. early dismissal - 1 bus boys & girls | |
| Fri., 1/11 | V Girls Indoor Track | Yale Invitational Coxe Cage, New Haven | Away | 1:00 p.m. | early dismissal @ 10:50 a.m. - no bus | |
| Sat., 1/12 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice Rink [Directions] | 5:00 p.m. | L 0-2 | Non League |
| Sat., 1/12 | V Boys Indoor Track | Yale Invitational, Coxe Cage, New Haven | Away | 7:30 a.m. | No bus needed | |
| Sat., 1/12 | V Boys Indoor Track | Wilton, Fairfield Ludlowe, Danbury, Greenwich | Away [Directions] | 9:30 a.m. | Total of 2 buses needed for boys & girls | |
| Sat., 1/12 | V Wrestling | Derby/Oxford/Holy Cross, Weston, Bunnell | Home - DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/12 | V Girls Gymnastics | Greenwich | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien: 125.1 Greenwich: 123.45 | |
| Sat., 1/12 | V Girls Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | 7:10 p.m. | W 2-0 | |
| Sat., 1/12 | V Girls Indoor Track | Yale Invitational Coxe Cage, New Haven | Away | 7:30 a.m. | No bus needed | |
| Sat., 1/12 | V Girls Indoor Track | Wilton, Fairfield Ludlowe, Danbury, Greenwich | Away [Directions] | 9:30 a.m. | @ Wilton - total of 2 buses needed for boys & girls | |
| Mon., 1/14 | V Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 59-66 | |
| Mon., 1/14 | JV Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | FR Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/14 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Mon., 1/14 | V Boys Squash | Greens Farms Academy | Away | 3:30 p.m. | ||
| Mon., 1/14 | JV Boys Squash | Greens Farms Academy | Away | 4:30 p.m. | 1 bus Varsity & JV Boys | |
| Mon., 1/14 | V Boys Swimming and Diving | Danbury | Home - Darien YMCA [Directions] | 7:00 p.m. | no bus | |
| Mon., 1/14 | V Competitive Cheerleading | Danbury | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Mon., 1/14 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | L 35-49 | 1 bus Varsity/JV |
| Mon., 1/14 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 1 bus Varsity/JV - ECS Transportation | |
| Mon., 1/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 3:30 p.m. | W 5-1 | |
| Wed., 1/16 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice Rink [Directions] | 6:00 p.m. | W 9-0 | |
| Wed., 1/16 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Darien YMCA [Directions] | 3:00 p.m. | No bus due to exam schedule | |
| Wed., 1/16 | V Wrestling | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/16 | FR Girls Basketball | Danbury | Away - Danbury HS - NEW gym [Directions] | Cancelled | Cancelled | |
| Wed., 1/16 | V Girls Ice Hockey | West Haven/SHA | Home - Stamford Twin Rinks [Directions] | 3:00 p.m. | W 6-2 | No bus |
| Thu., 1/17 | V Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 7:00 p.m. | L 53-60 | 1 bus Var/JV |
| Thu., 1/17 | JV Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | 1 bus Var/JV | |
| Thu., 1/17 | FR Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 1/17 | V Girls Basketball | Stamford | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 48-52 | |
| Thu., 1/17 | JV Girls Basketball | Stamford | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/17 | FR Girls Basketball | Stamford | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/17 | V Girls Squash | St. Lukes | Away | 4:15 p.m. | ||
| Fri., 1/18 | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Sat., 1/19 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | 1:00 p.m. | W 4-3(OT) | |
| Sat., 1/19 | V Boys Indoor Track | Staples, Stamford, St. Joseph, Greenwich | Away [Directions] | 10:00 a.m. | Two buses total for boys/girls | |
| Sat., 1/19 | V Boys Indoor Track | SCC Coach's Invitational @ Hillhouse HS, New Haven | Away | 9:00 a.m. | No bus needed | |
| Sat., 1/19 | V Wrestling | New Milford Invitational | Away | Cancelled | Cancelled | |
| Sat., 1/19 | V Competitive Cheerleading | Fairfield Ludlowe Cheer Competition | Away | Cancelled | Cancelled | |
| Sat., 1/19 | V Girls Gymnastics | New Canaan, Westhill | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien: 125 New Canaan: 110.55 Westhill: 102.35 | |
| Sat., 1/19 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice Rink [Directions] | 3:50 p.m. | W 7-1 | |
| Sat., 1/19 | V Girls Indoor Track | Staples, Stamford, St. Joseph, Greenwich | Away [Directions] | 10:00 a.m. | @ Staples - Two buses needed | |
| Sat., 1/19 | V Girls Indoor Track | SCC Coaches Invite @ Hillhouse HS -Floyd Little, New Haven | Away | 1:30 p.m. | One bus | |
| Sat., 1/19 | JV Girls Squash | Miss Porter's School @ Chelsea Piers, Stamford | Away | 2:00 p.m. | ||
| Mon., 1/21 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | 6:00 p.m. | W 8-0 | |
| Mon., 1/21 | JV Boys Ice Hockey | St. Joseph | Home - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Mon., 1/21 | V Boys Indoor Track | New Haven Soph/Fresh Meet @ Hillhouse HS | Away | 9:00 a.m. | No bus needed | |
| Tue., 1/22 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 57-65 | 1 bus Var/JV |
| Tue., 1/22 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | 1 bus Var/JV | |
| Tue., 1/22 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/22 | V Girls Basketball | Wilton | Home - DHS Main Gym [Directions] | 6:00 p.m. | L 41-43 | |
| Tue., 1/22 | JV Girls Basketball | Wilton | Home - DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/23 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners Ice Rink [Directions] | 4:00 p.m. | W 8-0 | |
| Wed., 1/23 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | early dismiss @ 1:50 p.m. | |
| Wed., 1/23 | V Wrestling | New Canaan | Home - DHS - South Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/23 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 8:30 p.m. | W 6-1 | Requesting new bus and driver Lewin |
| Wed., 1/23 | JV Girls Squash | Staples | Home - Chelsea Piers, Stamford [Directions] | 8:30 p.m. | ||
| Thu., 1/24 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | 5:10 p.m. | @ Bennett Rink, West Haven | |
| Thu., 1/24 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | Cancelled | Cancelled | |
| Fri., 1/25 | V Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 51-67 | |
| Fri., 1/25 | JV Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 4:50 p.m. | ||
| Fri., 1/25 | V Boys Squash | Greenwich | Away [Directions] | 6:00 p.m. | @ MSquash, Port Chester, NY - no bus | |
| Fri., 1/25 | JV Boys Squash | Greenwich | Away [Directions] | 6:00 p.m. | @ MSquash, Port Chester, NY - No bus | |
| Fri., 1/25 | V Competitive Cheerleading | Ridgefield | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 27-52 | 1 bus Varsity/JV |
| Fri., 1/25 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | 1 bus Varsity/JV | |
| Fri., 1/25 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | V Girls Gymnastics | Wilton | Away [Directions] | 5:00 p.m. | Darien: 127.1 Wilton: 13.95 Oxford: 129.9 | PICKUP AT DARIEN YMCA |
| Sat., 1/26 | V Boys Indoor Track | Eastern Division Championships @ Wilton | Away | 9:30 a.m. | Two buses total for both boys/girls | |
| Sat., 1/26 | V Wrestling | Mahopac (NY) Tournament | Away | 9:00 a.m. | ||
| Sat., 1/26 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 7:10 p.m. | T 1-1(OT) | |
| Sat., 1/26 | V Girls Indoor Track | Eastern Division Championships @ Wilton | Away | 9:30 a.m. | Two buses total for both boys/girls | |
| Mon., 1/28 | V Co-ed Alpine Skiing | State Shootout @ Mt. Southington | Away | 4:00 p.m. | Early dismissal @ 1:30 p.m. | |
| Mon., 1/28 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice Rink [Directions] | 7:40 p.m. | W 8-1 | |
| Mon., 1/28 | V Girls Squash | Sacred Heart - Greenwich | Away | 4:00 p.m. | ||
| Tue., 1/29 | V Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 65-82 | |
| Tue., 1/29 | JV Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/29 | FR Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/29 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice Rink [Directions] | 8:30 p.m. | ||
| Tue., 1/29 | V Competitive Cheerleading | Fairfield Warde | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Tue., 1/29 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 30-41 | 1 bus Varsity/JV |
| Tue., 1/29 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | 1 bus Varsity/JV | |
| Tue., 1/29 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/29 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | 7:40 p.m. | W 8-1 | @ Terry Connors Rink - Requesting new bus and driver Lewin |
| Tue., 1/29 | V Girls Squash | Rye (NY) | Away | 8:00 p.m. | @ Life Time Athletic, Harrison, NY | |
| Wed., 1/30 | V Boys Ice Hockey | New Canaan | Home - Darien Ice Rink [Directions] | 4:00 p.m. | W 4-3 | |
| Wed., 1/30 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | Cancelled | Cancelled | POSTPONED |
| Wed., 1/30 | JV Girls Squash | Fairfield @ Chelsea Piers, Stamford | Home [Directions] | 8:30 p.m. | ||
| Thu., 1/31 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | W 74-71(2OT) | 1 bus for Var/JV |
| Thu., 1/31 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | 1 bus for Var/JV | |
| Thu., 1/31 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | V Boys Indoor Track | FCIAC Championships @ Hillhouse HS, New Haven | Away | 5:30 p.m. | One bus for both boys & girls | |
| Thu., 1/31 | V Wrestling | Fairfield Warde, Fairfield Prep, Greenwich, Norwalk | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | Multi-Team Event @ Warde | |
| Thu., 1/31 | V Girls Basketball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 7:00 p.m. | L 35-51 | |
| Thu., 1/31 | JV Girls Basketball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Girls Basketball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | V Girls Indoor Track | FCIAC Championships @ Hillhouse HS | Away | 5:30 p.m. | 1 bus for both boys & girls | |
| Fri., 2/1 | V Boys Ice Hockey | Trinity Catholic | Home - Darien Ice Rink [Directions] | 7:30 p.m. | W 7-1 | |
| Fri., 2/1 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena [Directions] | Cancelled | Cancelled | |
| Fri., 2/1 | V Boys Squash | U.S. Squash Nationals in Hartford, CT | Away | 12:00 p.m. | Full day dismissal - Tourney runs 2/1-2/3 | |
| Fri., 2/1 | V Boys Swimming and Diving | Ridgefield | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:50 p.m. - one way | |
| Fri., 2/1 | FR Girls Basketball | New Canaan | Away - Saxe Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/1 | V Girls Squash | U.S. Squash Nationals, Hartford, CT | Away | 12:00 p.m. | Full day dismissal - Tourney runs 2/1-2/3 | |
| Sat., 2/2 | V Boys Indoor Track | FCIAC JV Invitational @ Staples HS | Away | 10:00 a.m. | One bus for boys | |
| Sat., 2/2 | V Wrestling | Lawmen Invitational @ Jonathan Law HS | Away | 9:00 a.m. | ||
| Sat., 2/2 | V Competitive Cheerleading | FCIAC Cheer Competition @ Wilton HS Field House | Away | 9:00 a.m. | Returning around 4:00 p.m. | |
| Sat., 2/2 | V Girls Gymnastics | Trumbull, Staples | Home - Darien YMCA [Directions] | 2:30 p.m. | Darien: 130.95 Staples: 124.4 Trumbull: 131.7 | |
| Sat., 2/2 | V Girls Ice Hockey | East Catholic Coop | Home - Darien Ice Rink [Directions] | 5:20 p.m. | W 4-2 | |
| Mon., 2/4 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Darien Ice Rink [Directions] | 8:10 p.m. | W 6-0 | |
| Mon., 2/4 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Mon., 2/4 | V Co-ed Alpine Skiing | SL State Shootouts | Away | 4:00 p.m. | Early dismiss @ 1:30 p.m. - Top 30 | |
| Mon., 2/4 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 6:30 p.m. | W 6-0 | @ Rinks at Shelton -Requesting new bus and driver Lewin |
| Tue., 2/5 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | W 54-45 | 1 bus Var/JV |
| Tue., 2/5 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | 1 bus Var/JV | |
| Tue., 2/5 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/5 | V Wrestling | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | ||
| Tue., 2/5 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:40 p.m. | Early dismissal @ 1:30 p.m. | |
| Tue., 2/5 | V Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 31-18 | |
| Tue., 2/5 | JV Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/5 | V Girls Squash | Greenwich Academy | Away | 4:00 p.m. | ||
| Thu., 2/7 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | Early dismiss @ 1:30 p.m. | |
| Fri., 2/8 | V Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 56-51 | |
| Fri., 2/8 | JV Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/8 | JV Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 8:30 p.m. | ||
| Fri., 2/8 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | Early dismiss @ 1:30 p.m. - 1 bus for both boys & girls | |
| Fri., 2/8 | V Boys Squash | FairWest Championship @ Chelsea Piers, Stamford | Home [Directions] | TBA | Feb. 8-9 - no bus needed | |
| Fri., 2/8 | JV Boys Squash | FairWest Championship @ Chelsea Piers, Stamford | Away | TBA | Feb. 8-9 - no bus needed | |
| Fri., 2/8 | V Wrestling | FCIAC Tournament- @ New Canaan HS | Away | 4:00 p.m. | ||
| Fri., 2/8 | V Competitive Cheerleading | Staples | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 7:00 p.m. | L 38-50 | 1 bus Varsity/JV |
| Fri., 2/8 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | 1 bus Varsity/JV | |
| Fri., 2/8 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | Early dismiss @ 1:30 p.m. - 1 bus for both boys & girls | |
| Sat., 2/9 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 6:00 p.m. | W 6-0 | |
| Sat., 2/9 | V Wrestling | FCIAC Tournament- @ New Canaan HS | Away | 9:00 a.m. | ||
| Sat., 2/9 | V Competitive Cheerleading | Fairfield Warde Winter Competition | Away | Cancelled | Cancelled | |
| Sat., 2/9 | V Girls Gymnastics | FCIAC Championships @ Westhill HS | Away | 9:00 a.m. | 6th Place | PICKUP FROM DARIEN YMCA |
| Sat., 2/9 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 6:30 p.m. | W 1-0 | Requesting new bus and driver Lewin |
| Sun., 2/10 | V Girls Squash | FairWest Championship @ Yale, New Haven | Away | 3:00 p.m. | 15 passengers - returning around 6:00 p.m. | |
| Sun., 2/10 | JV Girls Squash | FairWest Championship @ Yale, New Haven | Away | 3:00 p.m. | 1 bus Var/JV | |
| Mon., 2/11 | V Boys Basketball | Harding | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 66-62 | |
| Mon., 2/11 | JV Boys Basketball | Harding | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/11 | FR Boys Basketball | Harding | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | V Boys Swimming and Diving | Trumbull | Home - Darien YMCA [Directions] | 3:00 p.m. | Early dismiss @ 1:50 p.m. - one way | |
| Mon., 2/11 | V Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | W 54-32 | 1 bus Varsity/JV |
| Mon., 2/11 | JV Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/13 | V Boys Basketball | Westhill | Home - DHS Main Gym [Directions] | 7:00 p.m. | W 66-61 | |
| Wed., 2/13 | JV Boys Basketball | Westhill | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/13 | FR Boys Basketball | Westhill | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/13 | V Boys Ice Hockey | Wilton | Home - Darien Ice Rink [Directions] | 8:30 p.m. | W 7-0 | |
| Wed., 2/13 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | 4:00 p.m. | @ Wonderland of Ice | |
| Wed., 2/13 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | Early dismiss @ 1:30 p.m. | |
| Wed., 2/13 | V Competitive Cheerleading | Westhill | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/13 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 44-33 | 1 bus Varsity/JV |
| Wed., 2/13 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | 1 bus Varsity/JV | |
| Wed., 2/13 | V Girls Gymnastics | JV Tournament @ Westhill | Away | Cancelled | Cancelled | |
| Wed., 2/13 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice Rink [Directions] | 7:10 p.m. | W 7-1 | |
| Fri., 2/15 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 4:45 p.m. | ||
| Sat., 2/16 | V Boys Ice Hockey | Trumbull | Home - Darien Ice Rink [Directions] | 5:40 p.m. | W 7-0 | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | No bus needed for boys | |
| Sat., 2/16 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 9:00 a.m. | ||
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 1 bus needed | |
| Mon., 2/18 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | L 58-60 | 1 bus Var/JV |
| Mon., 2/18 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | 1 bus Var/JV | |
| Mon., 2/18 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Mon., 2/18 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:30 p.m. | W 4-2 | |
| Mon., 2/18 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Thu., 2/21 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice Rink [Directions] | 6:00 p.m. | W 7-3 | |
| Thu., 2/21 | V Girls Ice Hockey | FCIAC Semi Finals vs Greenwich | Home - Darien Ice Rink [Directions] | 8:00 p.m. | Postponed from 2/20 due to weather | |
| Fri., 2/22 | V Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 7:00 p.m. | W 72-70 | 1 bus Var/JV |
| Fri., 2/22 | JV Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:15 p.m. | 1 bus Var/JV | |
| Fri., 2/22 | FR Boys Basketball | Norwalk | Away - Norwalk HS [Directions] | 4:00 p.m. | ||
| Fri., 2/22 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:00 p.m. | ||
| Sat., 2/23 | V Boys Basketball | FCIAC Quarterfinals @ Fairfield Warde | Away | Cancelled | Cancelled | |
| Sat., 2/23 | V Boys Ice Hockey | Tentative FCIAC Playdowns hosted by #3 & #4 seeds | Away | Cancelled | Cancelled | |
| Sat., 2/23 | JV Boys Ice Hockey | JV Championship vs Ridgefield @ Danbury Ice Arena | Away | 4:50 p.m. | ||
| Sat., 2/23 | V Boys Swimming and Diving | FCIAC JV Swim @ Greenwich HS | Away | Cancelled | Cancelled | |
| Sat., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Sat., 2/23 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law HS [Directions] | 8:30 a.m. | PICKUP FROM DARIEN YMCA | |
| Sat., 2/23 | V Girls Ice Hockey | Tentative FCIAC Finals | Away - Darien Ice Rink | Cancelled | Cancelled | |
| Mon., 2/25 | V Girls Basketball | CIAC Tourney 1st Round @ New London HS | Away - Higher Seed | 6:00 p.m. | ||
| Tue., 2/26 | V Boys Basketball | Tentative FCIAC Semi-finals @ Wilton | Away | Cancelled | Cancelled | Games @ 6:00 & 7:45 p.m. |
| Tue., 2/26 | JV Boys Ice Hockey | Hamden | Home - Darien Ice Rink [Directions] | 8:30 p.m. | ||
| Tue., 2/26 | V Boys Swimming and Diving | FCIAC Swim Trials @ Greenwich HS | Away | 5:30 p.m. | ||
| Tue., 2/26 | V Co-ed Alpine Skiing | Race @ Mt. Southington | Away | 4:00 p.m. | Early dismissal @ 1:30 p.m. | |
| Wed., 2/27 | V Boys Ice Hockey | FCIAC Semis vs Greenwich @ Darien Ice | Away | 5:00 p.m. | No bus needed | |
| Thu., 2/28 | V Boys Basketball | Tentative FCIAC Final @ Wilton | Away | Cancelled | Cancelled | |
| Thu., 2/28 | V Boys Swimming and Diving | FCIAC Swim Finals @ Greenwich HS | Away | 6:30 p.m. | ||
| Fri., 3/1 | V Girls Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | Cancelled | |
| Sat., 3/2 | V Boys Ice Hockey | Tentative FCIAC Final @ Dorothy Hamill Rink | Away | Cancelled | Cancelled | |
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | Cancelled | Cancelled | |
| Sat., 3/2 | V Girls Ice Hockey | State Quarter Final vs Greenwich | Home - Darien Ice Rink [Directions] | 4:00 p.m. | ||
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | No bus needed | |
| Sun., 3/3 | V Competitive Cheerleading | State Cheer Competition @ Hillhouse HS | Away | 9:00 a.m. | Returning around 2:30 p.m. | |
| Tue., 3/5 | V Boys Basketball | Newington | Away - Richard Rogalski Gymnasium @ Newington HS [Directions] | 6:00 p.m. | ||
| Tue., 3/5 | V Boys Ice Hockey | 1st Round CIAC vs St. Joes | Home - Darien Ice Rink [Directions] | 5:00 p.m. | ||
| Tue., 3/5 | V Co-ed Alpine Skiing | States Competition @ Mt. Southington | Away | 1:00 p.m. | Early dismissal @ 11:30 a.m. | |
| Wed., 3/6 | V Boys Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | Cancelled | |
| Wed., 3/6 | V Boys Ice Hockey | CIAC Tourney 1st Round | Away - Higher Seed | Cancelled | Cancelled | |
| Wed., 3/6 | V Boys Ice Hockey | CIAC Tourney 1st Round | Away - Higher Seed | Cancelled | Cancelled | |
| Wed., 3/6 | V Boys Ice Hockey | CIAC Tourney 1st Round | Away - Higher Seed | Cancelled | Cancelled | |
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | No bus needed | |
| Wed., 3/6 | V Girls Gymnastics | CIAC Open Championship | Away - New Milford HS [Directions] | 4:00 p.m. | No bus needed | |
| Wed., 3/6 | V Girls Ice Hockey | CIAC Semi-final vs West Haven @ Rinks of Shelton | Away | 7:30 p.m. | ||
| Thu., 3/7 | V Girls Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | |
| Fri., 3/8 | V Boys Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | |
| Sat., 3/9 | V Boys Ice Hockey | CIAC Tourney Quarterfinals vs Notre Dame - West Haven @ Wonderland of Ice | Away - Site TBA | 4:00 p.m. | ||
| Sat., 3/9 | V Boys Ice Hockey | CIAC Tourney Quarterfinals | Away - Site TBA | Cancelled | Cancelled | |
| Sat., 3/9 | V Boys Ice Hockey | CIAC Tourney Quarterfinals | Away - Site TBA | Cancelled | Cancelled | |
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class L Qualifying Swim Trials | Away - East Hartford HS [Directions] | 11:30 a.m. | ||
| Sat., 3/9 | V Girls Ice Hockey | CIAC Final vs New Canaan @ Bennett Rink | Away | 1:00 p.m. | Requesting Driver (Lewin) and new bus | |
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class L Swim Finals | Away - SCSU [Directions] | 6:30 p.m. | ||
| Mon., 3/11 | V Girls Basketball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | |
| Tue., 3/12 | V Boys Basketball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | |
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | No bus needed | |
| Wed., 3/13 | V Boys Ice Hockey | CIAC Tourney Semifinals | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Wed., 3/13 | V Boys Ice Hockey | CIAC Tourney Semifinals | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Wed., 3/13 | V Boys Ice Hockey | CIAC Tourney Semifinals | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | ||
| Sat., 3/16 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | |
| Sat., 3/16 | V Boys Ice Hockey | CIAC Tourney Final | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Sat., 3/16 | V Boys Ice Hockey | CIAC Tourney Final | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Sat., 3/16 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | |
| Sun., 3/17 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | |
| Sun., 3/17 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | |
| Tue., 3/19 | V Boys Ice Hockey | CIAC Tourney Final | Away - Ingalls Rink [Directions] | Cancelled | Cancelled | |
| Tue., 3/19 | V Boys Lacrosse | Blue/White Scrimmage | Home - DHS Center Oval Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 3/20 | V Baseball | Pelham Memorial (NY) (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 3:45 p.m. | ||
| Wed., 3/20 | JV Baseball | Pelham Memorial (NY) (Scrim.) | Home - DHS Baseball JV Field [Directions] | 3:45 p.m. | ||
| Thu., 3/21 | V Boys Lacrosse | John Jay (NY) (Scrim.) | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 3/22 | V Boys Rugby | @ Tomlinson MS, Fairfield, CT | Away | 4:30 p.m. | 200 Unquowa Rd, Fairfield, CT 06824 | |
| Fri., 3/22 | V Girls Lacrosse | Greenwich (Scrim.) | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Sat., 3/23 | V Baseball | Jamboree v Greenwich, McMahon, Ludlowe- also on JV field | Home - DHS Baseball Varsity Field [Directions] | 9:00 a.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Jamboree | Home - DHS Center Oval Turf Field [Directions] | 9:00 a.m. | Also Upper Oval Field | |
| Sat., 3/23 | V Boys Volleyball | Darien PlayDay | Home - DHS Main Gym [Directions] | 8:30 a.m. | ||
| Sat., 3/23 | V Softball | Softball Playday (Stamford, Westhill, Greenwich) | Home - DHS Softball Varsity Field [Directions] | 10:00 a.m. | Will also be using the Darien JV Softball Field and Stadium East | |
| Mon., 3/25 | V Girls Lacrosse | Convent of Sacred Heart (Scrim.) | Away | 4:30 p.m. | 1177 King St, Greenwich, CT 06831 | |
| Tue., 3/26 | V Baseball | Wilton (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | JV Baseball | Wilton (Scrim.) | Home - DHS Baseball JV Field [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Boys Lacrosse | Salisbury School (Scrim.) | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Rugby | Fairfield Prep | Away [Directions] | 5:30 p.m. | @ Barlow Field | |
| Wed., 3/27 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Away | 3:45 p.m. | ||
| Wed., 3/27 | V Softball | Wilton (Scrim.) | Away - WHS Varsity Softball Field [Directions] | 4:00 p.m. | Less than 18 passengers | |
| Fri., 3/29 | V Baseball | Stamford (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 3:15 p.m. | ||
| Fri., 3/29 | JV Baseball | Stamford (Scrim.) | Home - DHS Baseball JV Field [Directions] | 3:15 p.m. | ||
| Sat., 3/30 | V Boys Lacrosse | Yorktown (NY) | Home - DHS Stadium Field [Directions] | 1:00 p.m. | W 11-7 | |
| Sat., 3/30 | JV Boys Lacrosse | Yorktown (NY) | Home - DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 3/30 | FR Boys Lacrosse | Don Bosco (NJ) | Home - DHS Upper Oval Turf Field [Directions] | 11:30 a.m. | ||
| Sat., 3/30 | V Boys Volleyball | Newtown | Home - DHS Main Gym [Directions] | 12:00 p.m. | L 2-3 | |
| Sat., 3/30 | JV Boys Volleyball | Newtown | Home - DHS Main Gym [Directions] | 1:30 p.m. | ||
| Mon., 4/1 | V Boys Tennis | Bridgeport Central | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/1 | V Girls Lacrosse | Bronxville (NY) (Scrim.) | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Mon., 4/1 | JV Girls Lacrosse | Bronxville (NY) | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 4/1 | V Softball | Newtown | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 2-21 | |
| Mon., 4/1 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/2 | V Baseball | New Fairfield | Home - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 4/2 | JV Baseball | New Fairfield | Home - DHS Baseball JV Field [Directions] | 4:30 p.m. | L 10-3 | |
| Tue., 4/2 | V Boys Lacrosse | Westhill | Home - DHS Center Oval Turf Field [Directions] | 5:30 p.m. | W 12-0 | |
| Tue., 4/2 | JV Boys Lacrosse | Westhill | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Boys Tennis | Trumbull | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/2 | V Girls Lacrosse | Fairfield Warde | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 19-3 | |
| Tue., 4/2 | JV Girls Lacrosse | Fairfield Warde | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/3 | V Baseball | Stratford | Away - Penders Field [Directions] | 4:15 p.m. | L 2-3 | Longbrook Park - 103 Glendale Rd, Stratford, CT |
| Wed., 4/3 | JV Baseball | Stratford | Home - DHS Baseball JV Field [Directions] | 4:15 p.m. | L 11-9 | |
| Wed., 4/3 | FR Baseball | Westhill | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | FR Boys Lacrosse | Westhill | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Boys Rugby | Simsbury | Home - Royle School Field [Directions] | 5:45 p.m. | ||
| Wed., 4/3 | V Boys Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/3 | JV Boys Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/3 | V Girls Golf | Fairfield Ludlowe | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 204 Ludlowe 191 | One way - pickup front bus loop |
| Thu., 4/4 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:30 p.m. | W 4-3 | |
| Thu., 4/4 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Thu., 4/4 | V Girls Tennis | Greenwich | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 4/4 | JV Girls Tennis | Greenwich | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Fri., 4/5 | V Boys Lacrosse | Ridgefield | Home - DHS Stadium Field [Directions] | 6:30 p.m. | W 14-6 | |
| Fri., 4/5 | JV Boys Lacrosse | Ridgefield | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | 1 bus Var/JV |
| Fri., 4/5 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 1 bus Var/JV | |
| Fri., 4/5 | FR Girls Lacrosse | Wilton | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 4/6 | V Baseball | Guilford | Away - Baseball Field at GHS [Directions] | 2:00 p.m. | W 6-0 | |
| Sat., 4/6 | JV Baseball | Guilford | Home - DHS Baseball Varsity Field [Directions] | 11:00 a.m. | W 10-9 | |
| Sat., 4/6 | FR Baseball | Guilford | Home - DHS Baseball Varsity Field [Directions] | Cancelled | Cancelled | |
| Sat., 4/6 | FR Boys Lacrosse | Chaminade (NY) (Scrim.) | Home - DHS Upper Oval Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Garden City (NY) | Home - DHS Stadium Field [Directions] | 10:00 a.m. | W 19-4 | |
| Sat., 4/6 | JV Girls Lacrosse | Garden City (NY) (Scrim.) | Home - DHS Center Oval Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | V Softball | West Haven | Home - DHS Softball Varsity Field [Directions] | 2:00 p.m. | L 2-14 | |
| Mon., 4/8 | V Baseball | Bridgeport Central | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 10-2 | |
| Mon., 4/8 | FR Baseball | Westhill | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | JV Boys Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Trinity Catholic | Away | 4:00 p.m. | W 7-0 | |
| Mon., 4/8 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | 1 bus Var/JV |
| Mon., 4/8 | JV Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | 1 bus Var/JV | |
| Mon., 4/8 | FR Girls Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | V Girls Outdoor Track | St. Joseph, Fairfield Ludlowe | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Softball | Bridgeport Central | Away - Luis Marin Field #1 [Directions] | 4:00 p.m. | W 29-1 | |
| Mon., 4/8 | V Girls Tennis | Trinity Catholic | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/8 | JV Girls Tennis | Fairfield Warde | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Tue., 4/9 | V Boys Golf | Brien McMahon | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 157 McMahon 223 | |
| Tue., 4/9 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:30 p.m. | @ Smith | |
| Tue., 4/9 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 24-7 | |
| Tue., 4/9 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | Cancelled | Cancelled | |
| Tue., 4/9 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | Sound Shore Dr, Cos Cob, CT | |
| Tue., 4/9 | V Boys Outdoor Track | St. Joseph, Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | Two buses needed | |
| Tue., 4/9 | V Co-ed Sailing | Greens Farms Academy @ Pequot YC | Away | 4:00 p.m. | Small bus Round trip to Pequot YC 669 Harbor Rd, Southport, CT | |
| Tue., 4/9 | V Girls Golf | Fairfield Warde | Home - Wee Burn CC [Directions] | 3:00 p.m. | Warde 185 Darien 210 | |
| Tue., 4/9 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | W 18-8 | |
| Tue., 4/9 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 4/10 | V Baseball | Trumbull | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 4/10 | JV Baseball | Trumbull | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | L 4-2 | |
| Wed., 4/10 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | COMBINING WITH SOFTBALL | |
| Wed., 4/10 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | 3:15 p.m. | Darien 147 Stamford 205 | |
| Wed., 4/10 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 4:30 p.m. | ||
| Wed., 4/10 | V Boys Rugby | Greenwich | Away [Directions] | 4:30 p.m. | ||
| Wed., 4/10 | V Boys Tennis | Brien McMahon | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/10 | V Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | W 3-0 | 1 bus Var/JV |
| Wed., 4/10 | JV Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:30 p.m. | 1 bus Var/JV | |
| Wed., 4/10 | V Co-ed Sailing | FL/FW, BS, GA @ Pequot YC | Away | 4:00 p.m. | Small bus Round trip to Pequot YC 669 Harbor Rd, Southport, CT | |
| Wed., 4/10 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:15 p.m. | L 2-18 | COMBINING WITH FRESHMAN BASEBALL |
| Wed., 4/10 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:30 p.m. | W 7-0 | |
| Wed., 4/10 | JV Girls Tennis | Wilton | Away [Directions] | 4:00 p.m. | 24 passengers | |
| Thu., 4/11 | V Boys Golf | Fairfield Prep | Away - Country Club of Fairfield [Directions] | 3:00 p.m. | Darien 155 Prep 167 | Early dismissal @ 1:30 p.m. |
| Thu., 4/11 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:00 p.m. | 14 passenger van | |
| Thu., 4/11 | V Boys Outdoor Track | Trumbull | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Tennis | Danbury | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/11 | JV Boys Tennis | Fairfield Ludlowe | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | One way | |
| Thu., 4/11 | V Girls Golf | New Canaan | Home - Woodway CC [Directions] | 3:00 p.m. | Darien 194 New Canaan 174 | |
| Thu., 4/11 | JV Girls Golf | New Canaan | Home - Woodway CC [Directions] | 3:00 p.m. | ||
| Thu., 4/11 | FR Girls Lacrosse | New Canaan | Home - DHS Upper Oval Turf Field [Directions] | 5:15 p.m. | ||
| Thu., 4/11 | V Girls Tennis | Danbury | Away - WCSU Tennis Courts, Westside Campus [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/11 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:30 p.m. | W 10-0 | 1 bus Var/JV |
| Fri., 4/12 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | W 2-0 | 1 bus Var/JV - JV @ 180 E Elm St, Greenwich, CT |
| Fri., 4/12 | FR Baseball | Greenwich | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | FR Boys Lacrosse | Staples | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Westhill | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/12 | JV Boys Volleyball | Westhill | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | W 21-3 | |
| Fri., 4/12 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Fri., 4/12 | V Softball | Greenwich | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 4-16 | |
| Sat., 4/13 | V Boys Lacrosse | Manhassett (NY) | Away | 2:00 p.m. | L 5-10 | 200 Memorial Pl,Manhasset, NY |
| Sat., 4/13 | JV Boys Lacrosse | Manhassett (NY) | Away | 12:00 p.m. | 200 Memorial Pl,Manhasset, NY | |
| Sat., 4/13 | FR Girls Lacrosse | Ridgewood (NJ) (Scrim.) | Home - DHS Center Oval Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 4/15 | FR Baseball | New Canaan | Home - DHS Baseball Varsity Field [Directions] | 11:00 a.m. | ||
| Mon., 4/15 | FR Boys Lacrosse | St. Anthony's HS | Away | 6:30 p.m. | 275 Wolf Hill Road, South Huntington, NY | |
| Tue., 4/16 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:30 p.m. | W 23-8 | |
| Tue., 4/16 | JV Boys Lacrosse | Fairfield Warde | Home - DHS Center Oval Turf Field [Directions] | 12:00 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 1:00 p.m. | W 5-2 | |
| Tue., 4/16 | V Girls Lacrosse | Ridgefield | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 14-8 | |
| Tue., 4/16 | JV Girls Lacrosse | Ridgefield | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | FR Girls Lacrosse | Ridgefield | Home - DHS Upper Oval Turf Field [Directions] | 11:00 a.m. | ||
| Tue., 4/16 | V Softball | Fryeburg (ME) | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 16-8 | |
| Tue., 4/16 | V Girls Tennis | Wilton | Home - DHS Tennis Courts [Directions] | 10:00 a.m.. | W 4-3 | |
| Wed., 4/17 | V Baseball | Brien McMahon | Home - DHS Baseball Varsity Field [Directions] | 11:00 a.m. | L 2-6 | |
| Wed., 4/17 | JV Baseball | Brien McMahon | Home - DHS Baseball JV Field [Directions] | 11:00 a.m. | W 7-4 | |
| Wed., 4/17 | FR Baseball | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 11:00 a.m. | ||
| Wed., 4/17 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Boys Volleyball | Stamford | Home - DHS Main Gym [Directions] | 10:30 a.m. | W 3-0 | |
| Wed., 4/17 | JV Boys Volleyball | Stamford | Home - DHS Main Gym [Directions] | 12:00 p.m. | ||
| Wed., 4/17 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 11-4 | |
| Thu., 4/18 | V Baseball | Danbury | Home - DHS Baseball Varsity Field [Directions] | 10:00 a.m. | L 2-16(5) | |
| Thu., 4/18 | JV Baseball | Danbury | Home - DHS Baseball JV Field [Directions] | 10:00 a.m. | L 11-6 | |
| Thu., 4/18 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 18-6 | |
| Thu., 4/18 | JV Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Thu., 4/18 | FR Boys Lacrosse | New Canaan | Home - DHS Upper Oval Turf Field [Directions] | 11:00 a.m. | ||
| Thu., 4/18 | V Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 4/18 | JV Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 4:30 p.m. | 1 bus Var/JV | |
| Thu., 4/18 | V Girls Lacrosse | Radnor (PA) | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 10-6 | |
| Thu., 4/18 | JV Girls Lacrosse | Radnor, PA | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 4:00 p.m. | L 0-13 | |
| Mon., 4/22 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | W 3-0 | Both Var/JV combining w/Girls Freshman Lax |
| Mon., 4/22 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | Both Var/JV combining w/Girls Freshman Lax | |
| Mon., 4/22 | V Girls Golf | Staples | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 210 Staples 197 | |
| Mon., 4/22 | JV Girls Golf | Staples | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/22 | JV Girls Lacrosse | Greenwich Academy | Away | 4:00 p.m. | 26 passengers | |
| Tue., 4/23 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:15 p.m. | W 24-0 | |
| Tue., 4/23 | V Boys Golf | Westhill | Home - CC of Darien [Directions] | 3:15 p.m. | Darien 151 Westhill 184 | One-Way |
| Tue., 4/23 | JV Boys Golf | New Canaan | Home - CC of Darien [Directions] | 3:15 p.m. | One-Way | |
| Tue., 4/23 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 4:30 p.m. | W 20-1 | |
| Tue., 4/23 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Wilton, Brien McMahon | Away - WHS Track [Directions] | 4:00 p.m. | 2 buses needed | |
| Tue., 4/23 | V Boys Tennis | Fairfield Warde | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/23 | JV Boys Tennis | Fairfield Warde | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | One way | |
| Tue., 4/23 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Darien 186 Trumbull 201 | Small bus for Var/JV - early dismiss @ 1:45 p.m. |
| Tue., 4/23 | JV Girls Golf | Trumbull | Away [Directions] | 3:15 p.m. | @ Tashua Knolls GC | |
| Tue., 4/23 | V Softball | Stamford | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 2-12 | |
| Tue., 4/23 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 5-2 | One Bus for for V/JV |
| Tue., 4/23 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:00 p.m. | W 6-3 | 1 bus Var/JV |
| Wed., 4/24 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | W 6-4 | 1 bus Var/JV |
| Wed., 4/24 | FR Baseball | Wilton | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Boys Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 149 Trumbull 191 | |
| Wed., 4/24 | JV Boys Golf | Trumbull | Home - Wee Burn [Directions] | 3:15 p.m. | ||
| Wed., 4/24 | JV Boys Lacrosse | Chaminade (NY) | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | FR Boys Lacrosse | Chaminade (NY) (Scrim.) | Away | 4:30 p.m. | 340 Jackson Ave, Mineola, NY | |
| Wed., 4/24 | V Boys Rugby | Ridgefield | Home - Royle School Field [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Ridgefield | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/24 | JV Boys Tennis | Ridgefield | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | One way | |
| Wed., 4/24 | V Boys Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/24 | JV Boys Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/24 | V Co-ed Sailing | FL/FW @ Pequot YC | Away | 4:00 p.m. | Small bus Round trip to Pequot YC 669 Harbor Rd, Southport, CT | |
| Wed., 4/24 | FR Girls Lacrosse | Greenwich Academy | Away | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Outdoor Track | Wilton, Brien McMahon | Away - WHS Track [Directions] | 4:00 p.m. | Two buses (1-J&R) and 1-First Student | |
| Wed., 4/24 | V Softball | Wilton | Home - DHS Softball Varsity Field [Directions] | 4:30 p.m. | L 2-5 | |
| Wed., 4/24 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | Varsity Only |
| Thu., 4/25 | V Baseball | Stamford | Away - SHS Baseball Field [Directions] | 4:00 p.m. | W 7-0 | 1 bus Var/JV |
| Thu., 4/25 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | L 1-0 | 1 bus Var/JV |
| Thu., 4/25 | FR Baseball | Stamford | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Golf | Fairfield Ludlowe | Home - Woodway CC [Directions] | 3:00 p.m. | Darien 160 Ludlowe 170 | |
| Thu., 4/25 | V Boys Golf | Fairfield Ludlowe | Home - Woodway CC [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | JV Boys Golf | Greenwich | Home - Woodway CC [Directions] | 3:15 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Danbury | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 21-4 | |
| Thu., 4/25 | JV Boys Lacrosse | Danbury | Home - DHS Center Oval Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | 1 bus Var/JV |
| Thu., 4/25 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | 1 bus Var/JV | |
| Thu., 4/25 | V Boys Volleyball | Danbury | Home - DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 4/25 | JV Boys Volleyball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 2:45 p.m. | Darien 186 Danbury 239 | Early dismiss @ 1:25 p.m. |
| Thu., 4/25 | JV Girls Golf | Fairfield Ludlowe | Away - South Pine Creek Par 3 [Directions] | 3:15 p.m. | Small bus | |
| Thu., 4/25 | V Girls Lacrosse | Bishop Ireton (VA) | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 11-10 | |
| Thu., 4/25 | V Girls Outdoor Track | Penn Relays | Away | TBA | 4/25-4/27 - registration fee is being processed | |
| Thu., 4/25 | V Softball | Ridgefield | Away - Tiger Ridge Softball Field (RHS) [Directions] | 4:00 p.m. | L 3-10 | Early dismiss @ 2:00 p.m. |
| Thu., 4/25 | V Girls Tennis | Fairfield Ludlowe | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/25 | JV Girls Tennis | Fairfield Ludlowe | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Fri., 4/26 | FR Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Boys Outdoor Track | O'Grady Relays @ Bethel HS | Away | Cancelled | Cancelled | |
| Sat., 4/27 | V Boys Lacrosse | Seton Hall Prep (NJ) | Away | 12:00 p.m. | L 11-12(OT) | 275 Wolf Hill Rd, South Huntington, NY |
| Sat., 4/27 | FR Boys Lacrosse | Daniel Hand | Home - DHS Upper Oval Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays @ Bethel HS | Away | 9:00 a.m. | Two buses total-One bus @ 7:00 a.m. and One bus @ 9:00 a.m. | |
| Sat., 4/27 | V Boys Tennis | Stamford | Away [Directions] | 11:00 a.m. | W 7-0 | |
| Sat., 4/27 | V Co-ed Sailing | CT State Championship @ Sail BlackRock, Bridgeport, CT | Away | 10:00 a.m. | Small bus round trip 80 Grovers Ave, Bridgeport, CT | |
| Sat., 4/27 | V Girls Lacrosse | Eastport-South Manor (NY) | Away | 3:00 p.m. | L 9-10 | 82 Turkey Ln, Cold Spring Harbor, NY -GAINS FOR BRAINS TOURNEY - Returning 6:00 p.m. |
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays at Bethel HS | Away | 9:00 a.m. | Two buses total -One bus @ 7:00 a.m. and One bus @ 9:00 a.m. | |
| Sat., 4/27 | V Softball | Trinity Catholic | Home - DHS Softball Varsity Field [Directions] | 11:00 a.m. | W 19-1 | |
| Sun., 4/28 | V Boys Lacrosse | St. Anthonys (NY) | Away | 10:00 a.m. | L 9-11 | 275 Wolf Hill Rd, South Huntington, NY |
| Sun., 4/28 | V Co-ed Sailing | Herreschoff Qualifier @ Sail BlackRock, Bridgeport, CT | Away | 9:00 a.m. | Small bus Round trip 80 Grovers Ave, Bridgeport, CT | |
| Mon., 4/29 | V Baseball | Fairfield Warde | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 4/29 | JV Baseball | Fairfield Warde | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | L 14-6 | |
| Mon., 4/29 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | Combining with Softball | |
| Mon., 4/29 | V Boys Golf | Ridgefield | Home - Wee Burn CC [Directions] | 3:15 p.m. | Darien 148 Ridgefield 171 | |
| Mon., 4/29 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | Small bus | |
| Mon., 4/29 | JV Boys Lacrosse | St. Anthonys (NY) (Scrim.) | Away | 5:00 p.m. | 275 Wolf Hill Road South Huntington, NY 11747 | |
| Mon., 4/29 | FR Boys Lacrosse | Fairfield Warde | Home - DHS Upper Oval Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | V Boys Rugby | Staples | Away [Directions] | 5:00 p.m. | ||
| Mon., 4/29 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 4/29 | JV Boys Tennis | New Canaan | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/29 | JV Boys Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | V Girls Lacrosse | St. Joseph | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 19-3 | |
| Mon., 4/29 | JV Girls Lacrosse | St. Joseph | Home - DHS Center Oval Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Bridgeport Central | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | L 0-10 | Combining with Freshman Baseball |
| Mon., 4/29 | V Girls Tennis | New Canaan | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/29 | JV Girls Tennis | New Canaan | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Tue., 4/30 | V Baseball | Ridgefield | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 3-2(9) | |
| Tue., 4/30 | FR Baseball | Ridgefield | Home - Darien JV Baseball field [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Darien 143 Norwalk 193 | |
| Tue., 4/30 | JV Boys Golf | Ridgefield | Home - CC of Darien [Directions] | 3:15 p.m. | ||
| Tue., 4/30 | V Boys Lacrosse | Trumbull | Away - New Turf Field [Directions] | 6:00 p.m. | W 18-6 | |
| Tue., 4/30 | JV Boys Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Bridgeport Central | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Staples | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 4/30 | JV Boys Tennis | Staples | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | One way | |
| Tue., 4/30 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:45 p.m. | Darien 223 Greenwich 188 | |
| Tue., 4/30 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | W 22-2 | |
| Tue., 4/30 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | 1 bus Var/JV |
| Tue., 4/30 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 1 bus Var/JV | |
| Wed., 5/1 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | L 1-4 | 1 bus Var/JV |
| Wed., 5/1 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park [Directions] | 4:00 p.m. | L 11-2 | 1 bus Var/JV |
| Wed., 5/1 | FR Baseball | Fairfield Ludlowe | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Golf | Danbury | Home - Woodway CC [Directions] | 3:15 p.m. | Darien 151 Danbury 179 | |
| Wed., 5/1 | FR Boys Lacrosse | Stamford | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Volleyball | Staples | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/1 | JV Boys Volleyball | Staples | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/1 | V Co-ed Sailing | GHS, RHS, RCDS @ Indian Harbor YC, Greenwich | Away | 4:00 p.m. | Small bus round trip 710 Steamboat Rd, Greenwich, CT | |
| Wed., 5/1 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:00 p.m. | Darien 203 Warde 186 | Early dismiss @ 2:00 p.m. |
| Wed., 5/1 | FR Girls Lacrosse | Fairfield Warde | Home - DHS Tennis Court Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Girls Outdoor Track | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | Two buses needed | |
| Wed., 5/1 | V Softball | Fairfield Ludlowe | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 0-12 | |
| Thu., 5/2 | JV Boys Lacrosse | Staples | Home - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Golf | St. Joseph | Away [Directions] | 3:15 p.m. | Darien 193 St Joes 216 | Early dismiss @ 1:45 p.m. |
| Thu., 5/2 | JV Girls Golf | Greenwich | Away - Milbrook Country Club [Directions] | 3:30 p.m. | Small bus to Millbrook GC | |
| Thu., 5/2 | V Girls Lacrosse | Manhassett (NY) | Away | 4:00 p.m. | L 11-12(OT) | Early dismiss @ 1:20 p.m. 200 Memorial Pl, Manhasset, NY -Returning 7:00 p.m. |
| Thu., 5/2 | JV Girls Lacrosse | Manhassett (NY) (Scrim.) | Away | 4:00 p.m. | ||
| Thu., 5/2 | JV Girls Tennis | Wilton | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Fri., 5/3 | V Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | W 1-0 | 1 bus Var/JV |
| Fri., 5/3 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | L 4-3 | 1 bus Var/JV |
| Fri., 5/3 | FR Baseball | New Canaan | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Wilton | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Boys Outdoor Track | Amity HS Midnight Meet, Woodbridge, CT | Away | 5:00 p.m. | One bus | |
| Fri., 5/3 | V Boys Rugby | Southington | Home - DHS Stadium Field [Directions] | 6:30 p.m. | ||
| Fri., 5/3 | V Boys Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/3 | JV Boys Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | FR Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Softball | New Canaan | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 8-5 | |
| Fri., 5/3 | V Girls Tennis | Stamford | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Sat., 5/4 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 2:00 p.m. | W 15-0 | |
| Sat., 5/4 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | FR Boys Lacrosse | Bosco Tournament | Away | 3:00 p.m. | 492 North Franklin Turnpike, Ramsey, NJ | |
| Sat., 5/4 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 3:00 p.m. | W 11-10 | |
| Sat., 5/4 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/4 | FR Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 1:00 p.m. | ||
| Sun., 5/5 | V Boys Lacrosse | Scrimmages @ Babson College | Away | 8:00 a.m. | ||
| Mon., 5/6 | V Baseball | Staples | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 5/6 | JV Baseball | Staples | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | L 11-0 | |
| Mon., 5/6 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | Small bus | |
| Mon., 5/6 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Westhill | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/6 | JV Boys Tennis | Greenwich | Home - Cherry Lawn Park [Directions] | 4:30 p.m. | One way | |
| Mon., 5/6 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-0 | 1 bus Var/JV |
| Mon., 5/6 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | 1 bus Var/JV | |
| Mon., 5/6 | V Girls Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 235 Trumbull 192 | |
| Mon., 5/6 | JV Girls Golf | Trumbull | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 5/6 | FR Girls Lacrosse | Norwalk | Home - DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Fairfield Warde, Norwalk | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Westhill | Away [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/6 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | Norwalk | Home - DHS Stadium Field [Directions] | 5:30 p.m. | W 22-2 | |
| Tue., 5/7 | JV Boys Lacrosse | Norwalk | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Fairfield Warde, Norwalk | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | Two buses needed | |
| Tue., 5/7 | V Boys Tennis | St. Joseph | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/7 | V Girls Lacrosse | Greenwich | Home - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 21-8 | |
| Tue., 5/7 | JV Girls Lacrosse | Greenwich | Home - DHS Center Oval Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | V Softball | Staples | Away - Greens Farms Elementary School [Directions] | 7:00 p.m. | L 7-8 | |
| Tue., 5/7 | V Girls Tennis | St. Joseph | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/8 | V Baseball | Norwich Free Academy | Away - Dodd Stadium [Directions] | 4:00 p.m. | L 5-8 | Early dismiss @ 1:00 p.m. -1 bus Var/JV |
| Wed., 5/8 | JV Baseball | Norwich Free Academy | Away - Dickenman Field [Directions] | 4:00 p.m. | L 11-6 | Early dismiss @ 1:00 p.m. - 1 bus Var/JV |
| Wed., 5/8 | V Boys Golf | Fairfield Warde | Home - CC of Darien [Directions] | 3:15 p.m. | Darien 157 Warde 174 | |
| Wed., 5/8 | FR Boys Lacrosse | Greenwich | Home - DHS Center Oval Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | W 3-0 | 1 bus Var/JV |
| Wed., 5/8 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 1 bus Var/JV | |
| Wed., 5/8 | V Co-ed Sailing | GFA, SHS @ Indian Harbor YC Greenwich | Away | 4:00 p.m. | Small bus round trip 10 Grass Island Rd, Greenwich, CT | |
| Wed., 5/8 | FR Girls Lacrosse | Greenwich | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Girls Outdoor Track | Sophomore Meet @ Staple HS | Away | 4:00 p.m. | ||
| Wed., 5/8 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:15 p.m. | ||
| Thu., 5/9 | V Boys Golf | St. Joseph | Away [Directions] | 3:15 p.m. | Darien 144 St. Joseph 170 | Early dismissal @ 1:30 p.m. / Tashua Knolls |
| Thu., 5/9 | V Boys Outdoor Track | Loucks Games @ White Plains HS | Away | Cancelled | Cancelled | *You must Qualify - Tourney = May 9-11, 2019 |
| Thu., 5/9 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/9 | JV Boys Tennis | New Canaan | Home - Cherry Lawn Park [Directions] | 4:00 p.m. | One way | |
| Thu., 5/9 | V Girls Golf | Wilton | Home - Woodway CC [Directions] | 3:00 p.m. | Darien 210 Wilton 220 | |
| Thu., 5/9 | V Girls Lacrosse | Westhill | Home - DHS Stadium Field [Directions] | 4:00 p.m. | W 19-4 | |
| Thu., 5/9 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | Westhill | Home - DHS Stadium Field [Directions] | Cancelled | Cancelled | |
| Thu., 5/9 | V Girls Tennis | Norwalk | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/9 | JV Girls Tennis | New Canaan | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Fri., 5/10 | V Baseball | Westhill | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 5-3 | |
| Fri., 5/10 | JV Baseball | Westhill | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | W 7-4 | |
| Fri., 5/10 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Boys Lacrosse | Bosco Tournament | Away | 6:30 p.m. | 492 North Franklin Turnpike, Ramsey, NJ | |
| Fri., 5/10 | V Boys Volleyball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 5/10 | JV Boys Volleyball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 3:00 p.m. | W 10-8 | Early dismissal @ 1:15 p.m. |
| Fri., 5/10 | FR Girls Lacrosse | Greenwich Academy | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Softball | Westhill | Away - Westhill Softball Field [Directions] | 4:00 p.m. | L 1-7 | |
| Sat., 5/11 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 3:00 p.m. | W 12-4 | |
| Sat., 5/11 | JV Boys Lacrosse | New Canaan | Away - WTT2 [Directions] | 10:00 a.m. | ||
| Sat., 5/11 | FR Boys Lacrosse | Tentative Bosco Tournament Championship | Away | 3:30 p.m. | 492 North Franklin Turnpike, Ramsey, NJ | |
| Sat., 5/11 | V Softball | Wamogo/Litchfield | Home - DHS Softball Varsity Field [Directions] | 11:00 a.m. | L 3-7 | |
| Sun., 5/12 | V Co-ed Sailing | Herreschoff Finals (if qualified) | Away | TBA | No bus | |
| Mon., 5/13 | JV Boys Golf | Staples | Home - Wee Burn CC [Directions] | Cancelled | Cancelled | |
| Mon., 5/13 | FR Boys Lacrosse | Ridgefield | Home - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Rugby | West Hartford | Away | Cancelled | Cancelled | |
| Mon., 5/13 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | 1 bus Var/JV |
| Mon., 5/13 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 1 bus Var/JV | |
| Mon., 5/13 | JV Girls Lacrosse | Longmeadow (MA) | Away | Cancelled | Cancelled | Tentative |
| Tue., 5/14 | V Baseball | St. Joseph | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/14 | JV Baseball | St. Joseph | Away - Unity Park, Trumbull [Directions] | 4:00 p.m. | L 11-14 | 1 bus Var/JV |
| Tue., 5/14 | V Boys Golf | Trinity Catholic | Away | 2:45 p.m. | Darien 149 Trinity 240 | @ Sterling Farms GC |
| Tue., 5/14 | JV Boys Golf | New Canaan | Home - CC of Darien [Directions] | 3:15 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | Trinity Catholic | Away - Trinity Catholic Alumni Field | 4:00 p.m. | ||
| Tue., 5/14 | FR Boys Lacrosse | Trumbull | Away - Indian Ledge Artificial Field [Directions] | 4:00 p.m. | 43 passengers | |
| Tue., 5/14 | JV Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Co-ed Sailing | League Championship @ Grass Island, Greenwich | Away | 4:00 p.m. | Under 10 passengers | |
| Tue., 5/14 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | Darien 216 NC 175 | |
| Tue., 5/14 | JV Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Cancelled | Cancelled | |
| Tue., 5/14 | V Softball | St. Joseph | Home - DHS Softball Varsity Field [Directions] | 4:30 p.m. | L 4-19 | |
| Tue., 5/14 | V Girls Tennis | FCIAC Quarterfinals vs Westhill | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | JV Girls Tennis | Ridgefield | Home - Weed Beach [Directions] | 4:00 p.m. | One way | |
| Wed., 5/15 | V Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 3:00 p.m. | W 11-4 | Early dismiss @ 1:20 p.m. |
| Wed., 5/15 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | L 6-0 | |
| Wed., 5/15 | FR Baseball | Norwalk | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | Darien 145 New Canaan 164 | |
| Wed., 5/15 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Small bus - under 12 passengers | |
| Wed., 5/15 | V Boys Lacrosse | Brunswick School | Away | 7:00 p.m. | ||
| Wed., 5/15 | JV Boys Lacrosse | Brunswick School | Away | 5:00 p.m. | ||
| Wed., 5/15 | V Boys Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | Two Buses Needed | |
| Wed., 5/15 | V Boys Tennis | Wilton | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 5/15 | V Boys Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 5/15 | JV Boys Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/15 | V Co-ed Sailing | Tentative League Championship @ TBD | Away | Cancelled | Cancelled | |
| Wed., 5/15 | V Girls Lacrosse | Longmeadow (MA) | Away | 6:00 p.m. | W 14-13 | 95 Grassy Gutter Rd, Longmeadow, MA -Returning 9 p.m. |
| Wed., 5/15 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Girls Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | Two buses needed | |
| Wed., 5/15 | V Softball | Norwalk | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 2-13 | |
| Wed., 5/15 | Unified Sports Track | Track Meet @ Fairfield Ludlowe | Away | Cancelled | Cancelled | |
| Thu., 5/16 | FR Baseball | St. Joseph | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | JV Boys Golf | Greenwich | Home - Woodway CC [Directions] | 3:15 p.m. | ||
| Thu., 5/16 | V Boys Rugby | Midstate | Home - Royle School Field [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | V Boys Tennis | New Canaan | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 5/16 | V Boys Volleyball | Joel Barlow | Home - DHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 5/16 | JV Boys Volleyball | Joel Barlow | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Lacrosse | FCIAC Quarter Final vs Trumbull | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Outdoor Track | Girls Track Freshman Meet @ Wilton | Away | 4:00 p.m. | No bus | |
| Thu., 5/16 | V Girls Tennis | FCIAC Semi-Finals vs Wilton | Home - DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 3:30 p.m. | ||
| Sat., 5/18 | V Baseball | FCIAC Quarterfinals vs Danbury | Home - DHS Baseball Varsity Field [Directions] | 2:00 p.m. | ||
| Sat., 5/18 | V Boys Lacrosse | FCIAC Quarter Final vs Trumbull | Home - DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Sat., 5/18 | FR Boys Lacrosse | Daniel Hand | Away - DHHS Turf Field [Directions] | 12:00 p.m. | ||
| Mon., 5/20 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | Darien 152 Wilton167 | |
| Mon., 5/20 | JV Boys Golf | Wilton | Away [Directions] | 3:30 p.m. | Small bus | |
| Mon., 5/20 | V Boys Volleyball | FCIAC Playdowns | Home [Directions] | Cancelled | Cancelled | |
| Mon., 5/20 | JV Girls Golf | Greenwich | Home - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 5/20 | JV Girls Golf | Fairfield Warde | Home - Wee Burn CC [Directions] | Cancelled | Cancelled | |
| Mon., 5/20 | V Girls Lacrosse | FCIAC Semi Finals vs Wilton @ Norwalk HS | Away | 5:00 p.m. | ||
| Mon., 5/20 | V Girls Tennis | Tentative FCIAC Finals @ Wilton | Away | Cancelled | Cancelled | |
| Tue., 5/21 | V Baseball | FCIAC Semi-finals vs Fairfield Ludlowe @ Cubeta Stadium | Away | 7:30 p.m. | ||
| Tue., 5/21 | V Boys Golf | Staples | Home - Wee Burn CC [Directions] | 3:00 p.m. | Darien 150 Staples 177 | |
| Tue., 5/21 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | Small bus | |
| Tue., 5/21 | V Boys Lacrosse | FCIAC Semi Final vs Wilton @ McMahon | Away | 7:00 p.m. | Two buses needed | |
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship @ SCSU, New Haven, CT | Away | 1:30 p.m. | 2 buses total for both boys/girls - Early dismissal @ 10:45 a.m. | |
| Tue., 5/21 | V Girls Golf | Danbury | Home - CC of Darien [Directions] | 3:00 p.m. | Darien 194 Danbury 244 | |
| Tue., 5/21 | JV Girls Golf | Danbury | Home - CC of Darien [Directions] | 3:00 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship @ SCSU, New Haven | Away | 1:30 p.m. | 2 buses total for both boys/girls - Early dismiss @ 10:45 a.m. | |
| Wed., 5/22 | V Baseball | Tentative FCIAC Finals @ Cubeta Stadium | Away | Cancelled | Cancelled | |
| Wed., 5/22 | V Boys Golf | Greenwich | Away - Round Hill Country Club [Directions] | 3:30 p.m. | Greenwich 146 Darien 147 | Early dismissal @ 1:30 p.m. |
| Wed., 5/22 | V Boys Tennis | FCIAC Finals vs Staples @ Wilton | Away | 4:00 p.m. | ||
| Wed., 5/22 | V Boys Volleyball | FCIAC Semi-Finals vs New Canaan @ Fairfield Ludlowe | Away | 5:00 p.m. | ||
| Wed., 5/22 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 2:30 p.m. | Darien 198 Ridgefield 185 | Early dismiss @ 1:15 - 12 PASSENGERS- Var/JV |
| Wed., 5/22 | JV Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 2:30 p.m. | Combining with Varsity - total passengers 12 - early dismiss @ 1:15 | |
| Wed., 5/22 | V Girls Lacrosse | FCIAC Finals vs New Canaan @ Norwalk HS | Away | 7:00 p.m. | ||
| Thu., 5/23 | V Boys Golf | Chappa Invitational @ Longshore | Away | 12:00 p.m. | Early dismissal @ 10:30 a.m. | |
| Thu., 5/23 | V Boys Lacrosse | Tentative FCIAC Final @ McMahon | Away | Cancelled | Cancelled | Two buses needed |
| Thu., 5/23 | V Girls Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | Darien 205 Staples 180 | Early dismiss @ 2:00 p.m. |
| Fri., 5/24 | V Boys Tennis | CIAC Tourney Through Rnd. of 16 | Away - E. Hartford HS & Raquet Club | 8:30 a.m. | Early dismissal - all day | |
| Fri., 5/24 | V Boys Volleyball | FCIAC Final vs Staples @ Fairfield Ludlowe | Away | 7:00 p.m. | ||
| Fri., 5/24 | V Girls Tennis | CIAC Tourney Qualifying Round | Away - Highest Seed | Cancelled | Cancelled | |
| Sat., 5/25 | V Baseball | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | Cancelled | |
| Sat., 5/25 | V Boys Lacrosse | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | Cancelled | |
| Sat., 5/25 | V Boys Tennis | CIAC Tourney @ Wilton HS | Away [Directions] | 9:00 a.m. | ||
| Sat., 5/25 | V Girls Lacrosse | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | Cancelled | |
| Sat., 5/25 | V Girls Tennis | CIAC Tourney 1st Round - vs winner of Simsbury/NFA | Away - DHS Tennis Courts | TBA | If Simsbury = 11:00 a.m. If NFA = 12:30 p.m. | |
| Tue., 5/28 | V Boys Golf | Holahan | Home - Woodway CC [Directions] | 11:30 a.m. | Early dismissal @ 11:00 a.m. | |
| Tue., 5/28 | V Girls Golf | Fairfield Warde, Greenwich | Away - Fairchild Wheeler [Directions] | 2:45 p.m. | Darien 197 Warde | Early dismiss @ 1:20 p.m. |
| Tue., 5/28 | V Girls Lacrosse | CIAC Tourney 1st Round vs Amity | Home - DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Wed., 5/29 | V Baseball | CIAC Tourney 1st Round @ Danbury | Away - Higher Seed | 3:30 p.m. | Early dismiss @ 12:45 p.m. | |
| Wed., 5/29 | V Boys Lacrosse | CIAC Tourney 1st Round vs winner of Newington/Conard | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Quarterfinals @ Wesleyan | Away - Wesleyan University [Directions] | 3:30 p.m. | Early dismissal @ 12:45 p.m. | |
| Wed., 5/29 | V Boys Volleyball | CIAC Tourney 1st Round vs Shelton | Home - DHS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/29 | JV Girls Golf | Fairfield's JV Championship @ South Pine Creek | Away | TBA | Early dismiss @ 2:10 p.m. 3 passengers total | |
| Wed., 5/29 | V Girls Tennis | CIAC Tourney Quarterfinals vs Wilton | Home - DHS Tennis Courts [Directions] | 3:00 p.m. | Early dismiss @ 2:00 p.m. | |
| Thu., 5/30 | V Boys Golf | FCIAC Championhip @ Fairchild Wheeler | Away | 12:00 p.m. | Early dismissal @ 10:30 a.m. | |
| Thu., 5/30 | V Boys Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 3:00 p.m. | Early dismiss @ 11:35 - Boys & Girls combining on one bus | |
| Thu., 5/30 | V Boys Tennis | CIAC Tourney Semifinals @ Wesleyan | Away - Wesleyan University [Directions] | 2:30 p.m. | Early dismissal @ 12:15 p.m. - request Romain as driver | |
| Thu., 5/30 | V Girls Golf | FCIAC Championship @ Fairchild Wheeler | Away | 9:00 a.m. | All day dismissal | |
| Thu., 5/30 | V Girls Lacrosse | CIAC Tourney Quarterfinals vs Fairfield Ludlowe | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Girls Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 3:00 p.m. | Early dismiss @ 11:35 - boys & girls combining on one bus | |
| Thu., 5/30 | V Girls Tennis | Tentative CIAC Tourney Semifinals | Home - DHS Tennis Courts [Directions] | Cancelled | Cancelled | |
| Fri., 5/31 | V Baseball | CIAC Tourney 2nd Round vs Southington | Away - Higher Seed | 3:30 p.m. | Early dismissal @ 12:45 p.m. | |
| Fri., 5/31 | V Boys Tennis | CIAC Tourney Finals @ Wesleyan | Away - Wesleyan University [Directions] | 3:30 p.m. | Early dismissal @ 1:15 p.m. | |
| Fri., 5/31 | V Boys Volleyball | CIAC Tourney Quarterfinals vs Danbury | Home - DHS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 5/31 | V Girls Tennis | Tentative CIAC Tourney Final | Away - Site TBA | Cancelled | Cancelled | |
| Sat., 6/1 | V Baseball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | |
| Sat., 6/1 | V Boys Lacrosse | CIAC Tourney Quarterfinals vs Fairfield Ludlowe | Home - DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Sat., 6/1 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Wesleyan [Directions] | 12:00 p.m. | ||
| Sat., 6/1 | V Girls Tennis | State Open Qualifying, 1st and 2nd Rounds | Away - Singles @ Conard/Doubles @ Hall | 1:00 p.m. | No bus | |
| Mon., 6/3 | V Boys Golf | CIAC Div. I Championship | Away - Timberlin GC - Kensington [Directions] | 8:00 a.m. | All-day dismissal | |
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | Early dismiss @ 10:45 a.m. -No bus needed | |
| Mon., 6/3 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | Early dismiss @ 1:00 p.m. - no bus | |
| Mon., 6/3 | V Girls Lacrosse | CIAC Tourney Semifinals vs winner Staples/Wilton @ Brien McMahon | Away | 5:00 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | Early dismiss @ 10:30 a.m. - no bus needed | |
| Mon., 6/3 | V Girls Tennis | State Open Round of 16/Quarterfinals | Away - Yale University [Directions] | 12:00 p.m. | Early dismiss @ - no bus | |
| Tue., 6/4 | V Baseball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | |
| Tue., 6/4 | V Boys Tennis | State Open Singles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | Early dismiss @ 1:15 p.m. - small bus | |
| Tue., 6/4 | V Boys Volleyball | CIAC Tourney Semifinals vs Newtown at Fairfield Warde | Away - Site TBA | 7:00 p.m. | ||
| Tue., 6/4 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | ||
| Tue., 6/4 | V Girls Tennis | State Open Semifinals | Away - Yale University [Directions] | 3:00 p.m. | Early dismiss @ 12:30 p.m.- no bus | |
| Wed., 6/5 | V Boys Lacrosse | CIAC Tourney Semifinals vs Staples @ Brien McMahon | Away - Site TBA | 7:15 p.m. | Two (2) buses needed | |
| Wed., 6/5 | V Boys Tennis | State Open Finals | Away - Wesleyan [Directions] | 3:00 p.m. | Early dismiss @ 12:45 p.m. | |
| Wed., 6/5 | V Girls Golf | Guimares @ Heritage Village GC | Away | 1:00 p.m. | Early dismiss @ 11:00 a.m. | |
| Wed., 6/5 | V Girls Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | Cancelled | Cancelled | |
| Thu., 6/6 | V Boys Volleyball | CIAC Tourney Final vs Staples @ Shelton HS | Away - Site TBA | 5:00 p.m. | Early dismiss @ 1:45 p.m. | |
| Sat., 6/8 | V Baseball | CIAC Tourney Final | Away - Palmer Field, Middletown [Directions] | Cancelled | Cancelled | |
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Boys Lacrosse | CIAC Championship Final vs Wilton @ Brien McMahon | Away - Brien McMahon HS [Directions] | 3:30 p.m. | Two buses needed | |
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | No bus needed | |
| Sat., 6/8 | V Girls Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Girls Lacrosse | CIAC Tourney Final vs New Canaan @ Law | Away - Site TBA | 12:00 p.m. | ||
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | No bus needed | |
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | No bus needed | |
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Fri., 6/14 | V Boys Outdoor Track | New Balance Nationals Outdoor @ North Carolina A&T Univ./Greensboro, N.C. | Away | TBA | You must qualify for this meet (June 14-16) | |
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||
| Wed., 6/19 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||