| Darien 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1070 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | New Canaan (Scrim.) | Home - DHS Baseball JV Field [Directions] | 3:30 p.m. | ||
| TBA | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | TBA | ||
| TBA | V Boys Golf | St. Joseph, Norwalk, Brien McMahon | Away - Tashua Knolls, Trumbull [Directions] | Cancelled | ||
| TBA | JV Boys Ice Hockey | New Canaan | Home - Darien Ice Rink [Directions] | 2:50 p.m. | ||
| TBA | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Stamford Twin Rinks [Directions] | 7:40 p.m. | ||
| TBA | FR Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | TBA | ||
| TBA | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | TBA | 2:30 p.m. | |
| TBA | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Golf | Fairfield Ludlowe | Away [Directions] | 3:30 p.m. | @ South Pine Creek | |
| TBA | JV Girls Soccer | Bassick | Home - Middlesex Upper Field [Directions] | Cancelled | ||
| TBA | FR Softball | Danbury | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| TBA | FR Softball | Trumbull | Home - DHS Softball JV Field [Directions] | Cancelled | ||
| Tue., 8/26 | V Girls Soccer | Greenwich Academy (Scrim.) | Home - DHS Turf #2 [Directions] | 3:00 p.m. | ||
| Wed., 8/27 | V Boys Soccer | Blind Brook (NY) (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Thu., 8/28 | V Field Hockey | Rye Country Day (NY) (Scrim.) | Away | 3:30 p.m. | 2:30 | |
| Thu., 8/28 | JV Field Hockey | Rye Country Day (NY) (Scrim.) | Away | 3:30 p.m. | 2:30 p.m. | |
| Thu., 8/28 | V Girls Soccer | St. Lukes (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Fri., 8/29 | V Boys Soccer | Brunswick School (Scrim.) | Home - DHS Turf #2 [Directions] | 3:00 p.m. | ||
| Sat., 8/30 | V Football | Branford (Scrim.) | Away - Branford High School-Turf Field [Directions] | 9:00 a.m. | 7:00 a.m. | Two buses |
| Sat., 8/30 | FR Football | Brien McMahon (Scrim.) | Home - DHS Stadium Field [Directions] | 9:00 a.m. | ||
| Sat., 8/30 | V Boys Soccer | Jamboree @ Shelton HS | Away | 3:00 p.m. | 1:30 p.m. | |
| Sat., 8/30 | V Field Hockey | Granby Jamboree | Away | 9:00 a.m. | 7:00 a.m. | 9:00 - 1:00 |
| Sat., 8/30 | V Girls Soccer | Scarsdale (NY) (Scrim.) | Home - DHS Turf #2 [Directions] | 10:00 a.m. | ||
| Tue., 9/2 | V Boys Soccer | Brien McMahon (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Wed., 9/3 | V Field Hockey | Greenwich Academy (Scrim.) | Away | 3:30 p.m. | ||
| Wed., 9/3 | JV Field Hockey | Greenwich Academy (Scrim.) | Away | 3:30 p.m. | ||
| Thu., 9/4 | V Football | Brien McMahon (Scrim.) | Away - Brien McMahon HS [Directions] | 3:45 p.m. | TBD | |
| Thu., 9/4 | V Girls Volleyball | John Jay (NY) (Scrim.) | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/5 | V Girls Cross Country | Scrimmage in Trumbull with Barlow | Away | 4:15 p.m. | 2:30 p.m. | |
| Fri., 9/5 | V Girls Soccer | New Fairfield (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Sat., 9/6 | FR Football | Stamford (Scrim.) | Away - Stamford High School [Directions] | 8:30 a.m. | 7:00 a.m. | |
| Sat., 9/6 | FR Football | Stamford (Scrim.) | Home - Royle School Field [Directions] | Cancelled | ||
| Sat., 9/6 | V Field Hockey | Darien Play Day | Home - DHS Stadium Field [Directions] | 1:00 p.m. | 1:00 - 5:00 | |
| Sat., 9/6 | V Girls Volleyball | Darien Girls Volleyball Playday | Home - DHS Main Gym [Directions] | 7:00 a.m. | ||
| Tue., 9/9 | V Boys Cross Country | Harding, Brien McMahon, Trumbull, Bassick, Bridgeport Central | Away [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 9/9 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-3 | 5:00 p.m. | |
| Tue., 9/9 | JV Boys Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 5:00 p.m. | 3:45 p.m. | |
| Tue., 9/9 | FR Boys Soccer | Fairfield Ludlowe | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Tue., 9/9 | V Girls Cross Country | Harding (Beardsley Park), Brien McMahon, Trumbull, Bassick, Bridgeport Central | Away [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Wed., 9/10 | V Field Hockey | Ridgefield | Home - DHS Stadium Field [Directions] | W 2-0 | ||
| Wed., 9/10 | JV Field Hockey | Ridgefield | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 9/10 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/10 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | W 3-0 | ||
| Wed., 9/10 | JV Girls Soccer | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 9/10 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University- Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/10 | V Girls Volleyball | Brien McMahon | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Wed., 9/10 | JV Girls Volleyball | Brien McMahon | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/11 | V Boys Soccer | Westhill | Home - DHS Turf #2 [Directions] | W 2-0 | ||
| Thu., 9/11 | JV Boys Soccer | Westhill | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Fri., 9/12 | V Football | Hillhouse | Away - Wilbur Cross Athletic Complex [Directions] | W 47-25 | TBA | |
| Fri., 9/12 | FR Girls Soccer | New Canaan | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Fri., 9/12 | V Girls Volleyball | Bassick | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Fri., 9/12 | JV Girls Volleyball | Bassick | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/12 | FR Girls Volleyball | Newtown | Home - DHS - South Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/13 | V Boys Cross Country | Wilton Invitational @ Allens Meadows for JV & Freshman | Away | 9:30 a.m. | ||
| Sat., 9/13 | JV Football | Hillhouse | Away - Blake Field I [Directions] | 10:30 a.m. | ||
| Sat., 9/13 | FR Football | Don Bosco (NJ) (Scrim.) | Home - DHS Stadium Field [Directions] | 9:30 a.m. | ||
| Sat., 9/13 | FR Boys Soccer | Westhill | Away - Westhill Front Field [Directions] | 1:00 p.m.. | ||
| Sat., 9/13 | V Girls Cross Country | Wilton Invitational | Away | TBA | ||
| Sat., 9/13 | V Field Hockey | Lakeland/Panas (NY) | Home - DHS Stadium Field [Directions] | L 0-2 | ||
| Sat., 9/13 | JV Field Hockey | Lakeland/Panas (NY) | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Mon., 9/15 | FR Field Hockey | Ridgefield | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 9/15 | V Girls Soccer | Fairfield Warde | Home - DHS Turf #2 [Directions] | L 3-0 | ||
| Mon., 9/15 | JV Girls Soccer | Fairfield Warde | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Tue., 9/16 | V Boys Cross Country | Wilton, Westhill, Fairfield Ludlowe, Bassick | Away - Allen's Meadow [Directions] | 4:00 p.m. | ||
| Tue., 9/16 | V Boys Soccer | Harding | Away - Went Field Park [Directions] | W 5-3 | ||
| Tue., 9/16 | FR Boys Soccer | Newtown | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Tue., 9/16 | V Girls Cross Country | Wilton, Westhill, Fairfield Ludlowe, Bassick | Away - Allen's Meadow [Directions] | 4:00 p.m. | ||
| Tue., 9/16 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | W 5-1 | ||
| Tue., 9/16 | JV Field Hockey | Norwalk | Away - NHS Grass Field [Directions] | 5:30 p.m. | ||
| Tue., 9/16 | FR Field Hockey | Norwalk | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 9/16 | FR Girls Soccer | Newtown | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Tue., 9/16 | V Girls Volleyball | Harding | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Tue., 9/16 | JV Girls Volleyball | Harding | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/17 | SO Football | Stamford | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Wed., 9/17 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 4-0 | ||
| Wed., 9/17 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 9/17 | V Girls Volleyball | Wilton | Away - Wilton High School Field House [Directions] | W 3-0 | ||
| Wed., 9/17 | JV Girls Volleyball | Wilton | Away - Wilton High School Field House [Directions] | 4:30 p.m. | ||
| Wed., 9/17 | FR Girls Volleyball | Wilton | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/18 | FR Football | Greenwich | Home - Royle School Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 9/18 | V Boys Soccer | Wilton | Home - DHS Turf #2 [Directions] | L 0-1 | ||
| Thu., 9/18 | JV Boys Soccer | Wilton | Home - Middlesex Upper Field [Directions] | 4:30 p.m. | ||
| Thu., 9/18 | FR Boys Soccer | Wilton | Away - Allen's Meadow [Directions] | 4:30 p.m. | 2:30 p.m. | |
| Thu., 9/18 | FR Field Hockey | St. Joseph | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 9/19 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | W 33-26 | ||
| Fri., 9/19 | V Field Hockey | Stamford | Home - DHS Stadium Field [Directions] | W 8-0 | ||
| Fri., 9/19 | JV Field Hockey | Stamford | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 9/19 | FR Field Hockey | Stamford | Away [Directions] | Cancelled | ||
| Fri., 9/19 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | T 1-1 | ||
| Fri., 9/19 | JV Girls Soccer | Wilton | Away - Allen's Meadow [Directions] | 4:00 p.m. | ||
| Fri., 9/19 | FR Girls Soccer | Wilton | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Fri., 9/19 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | ||
| Fri., 9/19 | V Girls Volleyball | Trumbull | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Fri., 9/19 | JV Girls Volleyball | Trumbull | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/19 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/20 | JV Football | Greenwich | Away - GHS Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 9/20 | V Field Hockey | Daniel Hand | Home - DHS Stadium Field [Directions] | W 2-0 | ||
| Sat., 9/20 | JV Field Hockey | Daniel Hand | Home - DHS Stadium Field [Directions] | 2:30 p.m. | ||
| Sat., 9/20 | JV Girls Swimming and Diving | Greenwich | Away [Directions] | 11:00 a.m. | ||
| Mon., 9/22 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | L 0-2 | 2:30 p.m. | |
| Mon., 9/22 | JV Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 9/22 | FR Boys Soccer | New Canaan | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Mon., 9/22 | V Girls Volleyball | Trinity Catholic | Away | W 3-0 | 2:30 p.m. | |
| Mon., 9/22 | JV Girls Volleyball | Trinity Catholic | Away | 4:00 p.m. | 2:30 p.m. | |
| Tue., 9/23 | V Boys Cross Country | Ridgefield, Fairfield Warde, Norwalk | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/23 | V Girls Cross Country | Ridgefield, Fairfield Warde, Norwalk | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/23 | FR Field Hockey | Staples | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 9/23 | V Girls Soccer | Trumbull | Home - DHS Turf #2 [Directions] | L 1-2 | ||
| Tue., 9/23 | JV Girls Soccer | Trumbull | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Wed., 9/24 | SO Football | Greenwich | Home - DHS Baseball JV Field [Directions] | 3:30 p.m. | ||
| Wed., 9/24 | V Boys Soccer | Trumbull | Home - DHS Turf #2 [Directions] | W 2-1 | ||
| Wed., 9/24 | JV Boys Soccer | Trumbull | Home - Middlesex Upper Field [Directions] | 3:00 p.m. | ||
| Wed., 9/24 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | W 5-3 | ||
| Wed., 9/24 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Wed., 9/24 | FR Field Hockey | New Canaan | Home - DHS Baseball Varsity Field [Directions] | 3:00 p.m. | ||
| Wed., 9/24 | V Girls Volleyball | Stamford | Away - Stamford High School [Directions] | W 3-0 | ||
| Wed., 9/24 | JV Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 4:30 p.m. | ||
| Wed., 9/24 | FR Girls Volleyball | Stamford | Home - DHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/26 | FR Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/26 | V Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | T 0-0 | ||
| Fri., 9/26 | JV Girls Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 7:00 p.m. | ||
| Fri., 9/26 | FR Girls Soccer | Danbury | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Sat., 9/27 | V Football | Bassick | Home - DHS Stadium Field [Directions] | W 41-0 | ||
| Sat., 9/27 | V Boys Soccer | Norwalk | Home - DHS Turf #2 [Directions] | T 0-0 | ||
| Sat., 9/27 | JV Boys Soccer | Norwalk | Home - DHS Turf #2 [Directions] | 9:00 a.m. | ||
| Sat., 9/27 | FR Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 11:00 a.m. | TBD | |
| Sat., 9/27 | V Girls Cross Country | Bethel Invitational for Freshman only | Away | Cancelled | ||
| Sat., 9/27 | V Girls Cross Country | Ocean State Invite, Goddard Park, RI | Away | TBA | ||
| Sat., 9/27 | V Girls Volleyball | John Jay Tourney | Away | TBA | ||
| Mon., 9/29 | JV Football | Bassick | Home - DHS Stadium Field [Directions] | Cancelled | ||
| Mon., 9/29 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/29 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/29 | V Girls Volleyball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Mon., 9/29 | JV Girls Volleyball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 9/29 | FR Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/30 | V Boys Cross Country | Greenwich, Stamford, New Canaan, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 9/30 | V Boys Soccer | Trinity Catholic | Home - DHS Turf #2 [Directions] | W 7-0 | ||
| Tue., 9/30 | V Girls Cross Country | Greenwich, Stamford, New Canaan, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 9/30 | V Field Hockey | Greenwich | Home - DHS Stadium Field [Directions] | W 7-1 | ||
| Tue., 9/30 | JV Field Hockey | Greenwich | Home - DHS Stadium Field [Directions] | 6:00 p.m. | ||
| Tue., 9/30 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 3:45 p.m. | ||
| Tue., 9/30 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | W 5-0 | ||
| Tue., 9/30 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | ||
| Tue., 9/30 | FR Girls Soccer | Fairfield Warde | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Wed., 10/1 | V Girls Soccer | Westhill | Home - DHS Turf #2 [Directions] | L 1-3 | ||
| Wed., 10/1 | JV Girls Soccer | Westhill | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Wed., 10/1 | V Girls Swimming and Diving | St. Joseph | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/1 | V Girls Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/1 | JV Girls Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/2 | V Football | St. Joseph | Home - DHS Stadium Field [Directions] | W 21-17 | ||
| Thu., 10/2 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | W 3-0 | 2:30 p.m. | |
| Thu., 10/2 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 10/2 | FR Girls Volleyball | Ridgefield | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/3 | FR Football | St. Joseph | Away - Upper Football Field [Directions] | 3:45 p.m. | ||
| Fri., 10/3 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | L 0-2 | ||
| Fri., 10/3 | V Girls Soccer | New Canaan | Home - DHS Turf #2 [Directions] | T 0-0 | ||
| Fri., 10/3 | JV Girls Soccer | New Canaan | Home - Middlesex Upper Field [Directions] | 3:30 p.m. | ||
| Fri., 10/3 | FR Girls Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 3:30 p.m. | ||
| Sat., 10/4 | V Boys Cross Country | Woods Trail Run @ Thetford Acad./VT | Away | TBA | ||
| Mon., 10/6 | JV Football | St. Joseph | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 10/6 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 3-2 | 2:30 p.m. | |
| Mon., 10/6 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 10/6 | FR Boys Soccer | Stamford | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Mon., 10/6 | V Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | W 5-1 | ||
| Mon., 10/6 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Mon., 10/6 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-0 | 2:30 p.m. | |
| Mon., 10/6 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 10/6 | FR Girls Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/7 | V Boys Cross Country | St. Joseph, Danbury, Staples | Away - St. Joseph High School [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 10/7 | V Girls Cross Country | St. Joseph, Danbury, Staples | Away [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 10/7 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | W 3-1 | ||
| Tue., 10/7 | JV Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 10/7 | FR Field Hockey | Fairfield Ludlowe | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 10/7 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 7-1 | ||
| Tue., 10/7 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:15 p.m. | ||
| Tue., 10/7 | FR Girls Soccer | Greenwich | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Wed., 10/8 | SO Football | Staples | Away [Directions] | Cancelled | ||
| Wed., 10/8 | V Boys Soccer | Greenwich | Home - DHS Turf #2 [Directions] | T 0-0 | ||
| Wed., 10/8 | JV Boys Soccer | Greenwich | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Wed., 10/8 | FR Boys Soccer | Greenwich | Away - GHS Field 7 [Directions] | 4:30 p.m. | 3:00 p.m. | |
| Wed., 10/8 | FR Field Hockey | Wilton | Home - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | ||
| Wed., 10/8 | V Girls Swimming and Diving | New Canaan | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/8 | V Girls Volleyball | Norwalk | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/8 | JV Girls Volleyball | Norwalk | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/9 | FR Boys Soccer | Newtown | Away - Newtown High School Practice Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 10/9 | V Girls Soccer | Trinity Catholic | Home - DHS Turf #2 [Directions] | W 7-0 | ||
| Thu., 10/9 | JV Girls Soccer | Harding | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Fri., 10/10 | FR Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 3:45 p.m. | ||
| Fri., 10/10 | V Boys Soccer | Bassick | Away [Directions] | W 3-1 | 2:30 p.m. | |
| Fri., 10/10 | V Field Hockey | Danbury | Home - DHS Stadium Field [Directions] | W 8-1 | ||
| Fri., 10/10 | JV Field Hockey | Danbury | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 10/10 | FR Field Hockey | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/10 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/10 | FR Girls Volleyball | Newtown | Away - Newtown High School Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/11 | V Boys Cross Country | Manhattan Invitational @ Van Cortlandt Park, Bronx, NY | Away | 10:45 a.m. | 8:15 a.m. | |
| Sat., 10/11 | V Football | Fairfield Warde | Home - DHS Stadium Field [Directions] | W 42-14 | ||
| Sat., 10/11 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 2:30 p.m. | ||
| Sat., 10/11 | JV Girls Swimming and Diving | Greenwich | Away [Directions] | 9:00 a.m. | ||
| Sat., 10/11 | V Girls Volleyball | Garden State Challenge VB Tourney @ Fairleigh Dickinson Univ. | Away | TBA | 10/11 & 10/12 | |
| Mon., 10/13 | JV Football | Fairfield Warde | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 10/13 | V Boys Soccer | Danbury | Home - DHS Turf #2 [Directions] | W 1-0 | ||
| Mon., 10/13 | JV Boys Soccer | Danbury | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Mon., 10/13 | FR Boys Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 10/13 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | W 3-1 | ||
| Mon., 10/13 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:15 p.m. | ||
| Mon., 10/13 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | ||
| Tue., 10/14 | FR Girls Soccer | Fairfield Ludlowe | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Tue., 10/14 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 3-0 | 2:30 p.m. | |
| Tue., 10/14 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | 2:30 p.m. | |
| Tue., 10/14 | FR Girls Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/15 | SO Football | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 10/15 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | L 2-3 | ||
| Wed., 10/15 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 10/15 | FR Field Hockey | Westhill | Home - DHS Baseball Varsity Field [Directions] | Cancelled | ||
| Wed., 10/15 | V Girls Swimming and Diving | Staples | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/15 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | W 3-0 | 2:30 p.m. | |
| Wed., 10/15 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | 2:30 p.m. | |
| Wed., 10/15 | FR Girls Volleyball | Staples | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/16 | FR Football | Trinity Catholic | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 10/16 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 3-2 | 4:15 p.m. | |
| Thu., 10/16 | V Girls Soccer | Bridgeport Central | Home - DHS Turf #2 [Directions] | W 5-0 | ||
| Fri., 10/17 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | W 4-1 | 2:30 p.m. | |
| Fri., 10/17 | JV Boys Soccer | Fairfield Warde | Home - DHS Turf #2 [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 10/17 | FR Boys Soccer | Fairfield Warde | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Fri., 10/17 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | W 6-0 | ||
| Fri., 10/17 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/17 | FR Field Hockey | Trumbull | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 10/17 | FR Girls Soccer | Newtown | Away - Newtown High School Practice Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 10/17 | V Girls Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Fri., 10/17 | JV Girls Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/17 | FR Girls Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Sat., 10/18 | V Football | Trinity Catholic | Away - Trinity Catholic Alumni Field | W 42-0 | ||
| Sat., 10/18 | V Field Hockey | Mamaroneck (NY) | Away | L 1-7 | ||
| Sat., 10/18 | JV Field Hockey | Mamaroneck (NY) | Away | Cancelled | ||
| Sat., 10/18 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 1-0 | ||
| Sat., 10/18 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 2:00 p.m. | ||
| Sat., 10/18 | FR Girls Soccer | Ridgefield | Home - Middlesex Lower Field [Directions] | 10:00 a.m. | ||
| Mon., 10/20 | V Boys Cross Country | FCIAC Championship @ Waveny Park, New Canaan | Away | 2:15 p.m. | ||
| Mon., 10/20 | JV Football | Trinity Catholic | Away - Trinity Catholic Alumni Field | Cancelled | ||
| Mon., 10/20 | V Boys Soccer | Ridgefield | Home - DHS Stadium Field [Directions] | W 2-1 | ||
| Mon., 10/20 | JV Boys Soccer | Ridgefield | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Mon., 10/20 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 10/20 | V Girls Cross Country | FCIACS @ Waveny Park, New Canaan | Away | 2:15 p.m. | ||
| Mon., 10/20 | V Girls Volleyball | Westhill | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/20 | JV Girls Volleyball | Westhill | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/20 | FR Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/21 | V Field Hockey | Brien McMahon | Home - DHS Stadium Field [Directions] | W 7-0 | ||
| Tue., 10/21 | JV Field Hockey | Brien McMahon | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 10/21 | V Girls Soccer | Staples | Home - DHS Turf #2 [Directions] | T 1-1 | ||
| Tue., 10/21 | JV Girls Soccer | Staples | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Tue., 10/21 | FR Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | 2:45 p.m. | |
| Wed., 10/22 | SO Football | Stamford | Home - DHS Baseball JV Field [Directions] | 3:30 p.m. | ||
| Wed., 10/22 | V Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | W 5-1 | 2:30 p.m. | |
| Wed., 10/22 | V Girls Swimming and Diving | Ridgefield | Home - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/22 | V Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | W 3-0 | 2:30 p.m. | |
| Wed., 10/22 | JV Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:30 p.m. | 2:30 p.m. | |
| Wed., 10/22 | FR Girls Volleyball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/23 | V Boys Cross Country | The Running Acad. Freshman Invitational @ Tarrywile Park, Danbury | Away | 4:00 p.m. | ||
| Thu., 10/23 | V Field Hockey | Fairfield Warde | Home - DHS Stadium Field [Directions] | W 3-0 | ||
| Thu., 10/23 | JV Field Hockey | Fairfield Warde | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 10/23 | V Girls Soccer | St. Joseph | Home - DHS Turf #2 [Directions] | L 1-2 | ||
| Fri., 10/24 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 50-23 | 3:45 p.m. | |
| Fri., 10/24 | FR Football | Ridgefield | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 10/24 | V Boys Soccer | FCIAC Playdown @ Norwalk | Home [Directions] | 6:00 p.m. | 5:00 p.m. | Rain-date 10/25/14 |
| Fri., 10/24 | JV Girls Soccer | St. Joseph | Home - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Fri., 10/24 | FR Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 10/24 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 3-0 | 2:30 p.m. | |
| Fri., 10/24 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | 2:30 p.m. | |
| Sat., 10/25 | V Boys Cross Country | CIAC Class L Championship @ Wickham Park, Manchester CT | Away | TBA | ||
| Sat., 10/25 | JV Football | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 2:00 p.m. | 12:00 p.m. | |
| Sat., 10/25 | V Girls Cross Country | CIAC Meet @ Wickham Park, East Hartford 5,000 meters | Away | TBA | ||
| Sat., 10/25 | V Field Hockey | Westhill | Home [Directions] | W 4-2 | ||
| Sat., 10/25 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | L 0-2 | Rain-date is 10/26 | |
| Sat., 10/25 | V Girls Swimming and Diving | JV FCIAC @ GREENWICH | Away | 4:00 p.m. | Warmup @ 3:00 p.m. | |
| Sat., 10/25 | FR Girls Volleyball | Southington Freshman Volleyball Playday | Away | 9:00 a.m. | TBD | |
| Mon., 10/27 | V Boys Soccer | Tentative FCIAC Semi-Finals @ Fairfield Ludlowe | Away | Cancelled | Games @ 5:00 and 7:00 p.m. | |
| Mon., 10/27 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 10/27 | V Girls Soccer | Tentative FCIAC Semi-Finals @ Norwalk | Away | Cancelled | ||
| Tue., 10/28 | V Field Hockey | FCIAC Semi-Finals vs Staples @ Brien McMahon | Away | 7:00 p.m. | ||
| Tue., 10/28 | V Girls Swimming and Diving | FCIAC Swim Trials @ Greenwich | Away | 4:00 p.m. | Warm-ups at 2:30 p.m. | |
| Tue., 10/28 | V Girls Volleyball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/29 | SO Football | New Canaan | Home - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Wed., 10/29 | V Boys Soccer | Wilton (Scrim.) | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Wed., 10/29 | V Boys Soccer | Tentative FCIAC Finals @ Norwalk | Away | Cancelled | ||
| Wed., 10/29 | V Girls Soccer | Tentative FCIAC Finals @ Norwalk | Away | 4:30 p.m. | ||
| Wed., 10/29 | V Girls Swimming and Diving | FCIAC Diving @ Westhill | Away | 4:00 p.m. | Warm-ups @ 2:30 p.m. | |
| Thu., 10/30 | FR Football | Wilton | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 10/30 | V Field Hockey | FCIAC Finals vs New Canaan @ Brien McMahon | Away | 7:00 p.m. | Rain date is 11/1 | |
| Thu., 10/30 | V Girls Swimming and Diving | FCIAC Swim Finals @ Greenwich | Away | 4:00 p.m. | Warm-ups @ 2:30 p.m. | |
| Thu., 10/30 | V Girls Volleyball | CIAC Semi-Finals vs Greenwich @ Fairfield Ludlowe | Away | 7:00 p.m. | 5:00 p.m. | |
| Fri., 10/31 | V Boys Cross Country | CIAC State Open Championship @ Wickham Park, Manchester, CT | Away | TBA | ||
| Fri., 10/31 | V Football | Wilton | Away - Fujitani Field - Turf [Directions] | W 41-0 | 3:30 p.m. | |
| Fri., 10/31 | V Girls Cross Country | CIAC State Open @ Wickham Park, East Hartford | Away | TBA | ||
| Sat., 11/1 | V Girls Volleyball | Tentative FCIAC Finals @ Fairfield Ludlowe | Away | 4:00 p.m. | 2:00 p.m. | |
| Mon., 11/3 | JV Football | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Mon., 11/3 | V Boys Soccer | CIAC - Round One vs Stamford | Home - DHS Turf #2 [Directions] | 2:00 p.m. | ||
| Mon., 11/3 | V Girls Volleyball | Scrimmage @ RHAM | Away | 4:00 p.m. | 2:00 p.m. | |
| Tue., 11/4 | V Girls Soccer | CIAC - Round One vs Newington | Home - DHS Turf #2 [Directions] | 2:00 p.m. | ||
| Wed., 11/5 | SO Football | Staples | Home - DHS Baseball JV Field [Directions] | 3:30 p.m. | ||
| Wed., 11/5 | V Boys Soccer | CIAC Round 2 @ Shelton | Away | 4:00 p.m. | TBD | |
| Wed., 11/5 | V Field Hockey | CIAC - Round One vs Westhill | Home [Directions] | 2:00 p.m. | ||
| Wed., 11/5 | V Girls Swimming and Diving | Class L Diving Championship @ Middletown | Away | 5:30 p.m. | Warm-up @ 4:00 p.m. | |
| Thu., 11/6 | FR Football | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 11/6 | V Girls Soccer | CIAC - Round 2 @ higher seed | Away | 2:00 p.m. | 10:45 a.m. | |
| Thu., 11/6 | V Girls Volleyball | CIAC - Round Two vs Hall | Home - DHS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 11/7 | V Boys Soccer | CIAC Quarterfinals vs Staples | Home - DHS Turf #2 [Directions] | 2:00 p.m. | ||
| Fri., 11/7 | V Field Hockey | CIAC - Quarterfinals @ Simsbury | Away | 5:00 p.m. | 1:30 p.m. | Raindate 11/8 |
| Sat., 11/8 | V Boys Cross Country | New England Championship @ Wickham Park, Manchester CT | Away | 11:30 a.m. | ||
| Sat., 11/8 | V Football | Harding | Home - DHS Stadium Field [Directions] | W 42-14 | ||
| Sat., 11/8 | V Girls Cross Country | New England Meet @ Wickham Park, E. Hartford | Away | 11:30 a.m. | ||
| Sat., 11/8 | V Girls Soccer | Tentative CIAC Quarterfinals @ higher seed | Away | Cancelled | ||
| Sat., 11/8 | V Girls Swimming and Diving | Class L Swimming Trials @ West Hartford | Away | 6:15 p.m. | 2:30 p.m. | Warm-ups @ 5:10 p.m. |
| Sat., 11/8 | V Girls Volleyball | CIAC Quarterfinals vs Ridgefield | Home - DHS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 11/10 | JV Football | Harding | Home - DHS Stadium Field [Directions] | 3:15 p.m. | ||
| Tue., 11/11 | V Boys Soccer | CIAC Semi-Finals vs Glastonbury @ West Haven HS | Away | 6:00 p.m. | ||
| Tue., 11/11 | V Field Hockey | CIAC Semifinal vs New Milford @ Ridgefield | Away | 6:00 p.m. | Raindate 11/12 | |
| Tue., 11/11 | V Girls Soccer | Tentative CIAC Semi-Finals @ site TBD | Away | Cancelled | Alternate date 11/12/14 | |
| Wed., 11/12 | V Girls Swimming and Diving | Class L Finals Champ. @ SCSU | Away | 6:00 p.m. | Warmups @ 5:00 p.m. | |
| Thu., 11/13 | FR Football | North Haven | Away - Vanacore Field [Directions] | 5:00 p.m. | ||
| Thu., 11/13 | V Girls Swimming and Diving | State Open Diving Champ. @ Middletown HS | Away | Cancelled | Warmups @ 4:00 p.m. | |
| Thu., 11/13 | V Girls Volleyball | CIAC Semi-Finals vs Fairfield Ludlowe @ Shelton HS | Away | 6:00 p.m. | 3:30 p.m. | |
| Fri., 11/14 | V Boys Soccer | Tentative CIAC Finals @ site TBD | Away | Cancelled | Alternate date 11/15/14 | |
| Fri., 11/14 | V Girls Soccer | Tentative CIAC Finals @ site TBD | Away | Cancelled | Alternate date 11/15/14 | |
| Sat., 11/15 | V Football | North Haven | Home - DHS Stadium Field [Directions] | W 31-0 | ||
| Sat., 11/15 | V Field Hockey | CIAC Final vs Glastonbury @ Wethersfield | Away | 12:30 p.m. | 9:30 a.m. | |
| Sat., 11/15 | V Girls Swimming and Diving | State Open Swim Champ. @ Yale | Away | 7:30 p.m. | 4:00 p.m. | Warmups @ 6:00 p.m. |
| Sat., 11/15 | V Girls Volleyball | CIAC Final vs Cheshire @ Glastonbury HS | Away | 7:00 p.m. | 4:00 p.m. | |
| Mon., 11/17 | JV Football | North Haven | Away - Vanacore Field [Directions] | Cancelled | 3:00 p.m. | |
| Thu., 11/20 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Sat., 11/22 | JV Football | New Canaan | Home - DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Thu., 11/27 | V Football | New Canaan | Home - Boyle Stadium/Stamford [Directions] | W 28-21 (OT) | ||
| Sat., 11/29 | V Boys Cross Country | Foot Locker Northeast Regional @ Van Cortlandt Park, Bronx, NY | Away | TBA | ||
| Sat., 11/29 | V Girls Ice Hockey | Alumnae Game | Home - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/3 | V Girls Basketball | Weston (Scrim.) | Home - DHS Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/6 | V Football | CIAC Semi-Final vs Naugatuck | Home - DHS Stadium Field [Directions] | 1:00 p.m. | ||
| Sat., 12/6 | V Girls Ice Hockey | Shelton Jamboree @ Rinks @ Shelton | Away | 4:30 p.m. | ||
| Sun., 12/7 | V Boys Ice Hockey | Bishop Hendricken (RI) (Scrim.) | Away | 4:00 p.m. | ||
| Wed., 12/10 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 36-69 | ||
| Wed., 12/10 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/10 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Sono Ice House [Directions] | 8:20 p.m. | ||
| Thu., 12/11 | V Boys Basketball | Immaculate (Scrim.) | Away - Immaculate High School [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 12/12 | JV Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | Cancelled | 7:15 p.m. | |
| Fri., 12/12 | V Girls Basketball | Norwalk | Home - DHS Main Gym [Directions] | W 54-52 | ||
| Fri., 12/12 | JV Girls Basketball | Norwalk | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/13 | V Boys Cross Country | Foot Locker XC Championships, Balboa Park, San Diego CA | Away | TBA | ||
| Sat., 12/13 | V Boys Ice Hockey | Jamboree @ Terry Conners Rink | Away | TBA | ||
| Sat., 12/13 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice Rink [Directions] | 3:50 p.m. | ||
| Mon., 12/15 | JV Boys Ice Hockey | New Canaan | Home - Stamford Twin Rinks [Directions] | 3:00 p.m. | ||
| Mon., 12/15 | V Girls Ice Hockey | New Canaan | Home - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/17 | V Boys Basketball | Westhill | Away [Directions] | L 43-64 | ||
| Wed., 12/17 | JV Boys Basketball | Westhill | Away [Directions] | 5:15 p.m. | ||
| Wed., 12/17 | FR Boys Basketball | Westhill | Away [Directions] | 4:00 p.m. | ||
| Wed., 12/17 | V Boys Ice Hockey | Hamden | Home - Darien Ice Rink [Directions] | W 4-3 | ||
| Wed., 12/17 | V Boys Indoor Track | Wesleyan Univ. Developmental | Away | 5:00 p.m. | 2:30 p.m. | |
| Wed., 12/17 | V Wrestling | Wilton | Home - DHS - South Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/17 | V Girls Basketball | Westhill | Home - DHS Main Gym [Directions] | W 48-40 | ||
| Wed., 12/17 | JV Girls Basketball | Westhill | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/19 | V Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | L 36-76 | ||
| Fri., 12/19 | JV Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/19 | FR Boys Basketball | Bridgeport Central | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 12/19 | V Boys Indoor Track | New Haven Varsity Invitational @ Hillhouse | Away | 4:00 p.m. | ||
| Fri., 12/19 | V Boys Swimming and Diving | Fairfield Warde | Home - Darien YMCA [Directions] | Fairfield 60 Darien 93 | ||
| Fri., 12/19 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 55-28 | ||
| Fri., 12/19 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/19 | V Girls Indoor Track | New Haven Invitational @ Hillhouse HS | Away | TBA | ||
| Sat., 12/20 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice Rink [Directions] | W 3-2 | ||
| Sat., 12/20 | V Boys Indoor Track | New Haven JV Invitational @ Hillhouse | Away | 9:00 a.m. | ||
| Sat., 12/20 | V Wrestling | Derby Invitational | Away | 10:00 a.m. | 7:00 a.m. | |
| Sat., 12/20 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Connors Rink [Directions] | 8:00 p.m. | ||
| Sat., 12/20 | V Girls Indoor Track | Reindeer Relays @ Wilton | Away | 9:30 a.m. | ||
| Mon., 12/22 | V Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | W 53-51 | ||
| Mon., 12/22 | JV Boys Basketball | St. Joseph | Away [Directions] | 5:15 p.m. | ||
| Mon., 12/22 | FR Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Mon., 12/22 | V Girls Basketball | St. Joseph | Home - DHS Main Gym [Directions] | L 26-39 | ||
| Mon., 12/22 | JV Girls Basketball | St. Joseph | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/27 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | W 6-3 | Non-League | |
| Sat., 12/27 | V Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | L 36-57 | ||
| Mon., 12/29 | V Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | L 23-35 | Either 11am or 1pm | |
| Mon., 12/29 | V Girls Indoor Track | Marine Corps. Meet, NYC | Away | TBA | ||
| Tue., 12/30 | FR Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 10:00 a.m. | ||
| Tue., 12/30 | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 1:45 p.m. | 12:15 p.m. | |
| Tue., 12/30 | V Wrestling | Newtown, Fairfield Warde, Ridgefield, Westhill | Away - Fairfield Warde Large Gym [Directions] | 10:00 a.m. | 8:15 a.m. | |
| Wed., 12/31 | V Boys Basketball | Weston | Home - DHS Main Gym [Directions] | L 53-62 | ||
| Wed., 12/31 | JV Boys Basketball | Weston | Home - DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/3 | V Boys Indoor Track | Developmental Meet @ Wilton v Ridgefield, St Joe's, Ludlowe, Warde, Westhill | Away | 9:30 a.m. | ||
| Sat., 1/3 | V Wrestling | Bethel, New Britain, Seymour, Stratford | Home - DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/3 | V Girls Gymnastics | Pomperaug Invitational | Away | 2nd Place New Milford 134.7 (1) Hand 129.4 (3) Fairfield Ludlowe 127.7 (4) Nonnewaug 125.150 (5) Pomperaug 120.850 (6) Conard 119.450 (7) Newtown 115.9 (8) Staples 113.150 (9) Hall 109.850 (10) Oxford 89.350 (11) | ||
| Sat., 1/3 | V Girls Ice Hockey | East Catholic Coop | Home - Darien Ice Rink [Directions] | 3:50 p.m. | ||
| Sat., 1/3 | V Girls Indoor Track | Developmental Meet @ Wilton v Ridgefield, St Joe's, Ludlowe, Warde, Westhill | Away | 9:30 a.m. | ||
| Mon., 1/5 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice Rink [Directions] | L 2-3 | ||
| Mon., 1/5 | JV Boys Ice Hockey | Stamford | Home - Darien Ice Rink [Directions] | 2:50 p.m. | ||
| Tue., 1/6 | V Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | L 57-60 | ||
| Tue., 1/6 | JV Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/6 | FR Boys Basketball | Danbury | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/6 | V Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | L 32-53 | ||
| Tue., 1/6 | JV Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:15 p.m. | ||
| Wed., 1/7 | V Boys Ice Hockey | Stamford | Away - Terry Conners Ice Rink [Directions] | W 8-3 | ||
| Wed., 1/7 | V Boys Swimming and Diving | Ridgefield | Home - Darien YMCA [Directions] | Darien 80 Ridgefield 106 | ||
| Wed., 1/7 | V Wrestling | Brien McMahon | Home - DHS - South Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/7 | V Co-ed Alpine Skiing | Race vs Glastonbury, Berlin, Hand, Ridgefield @ Southington | Away | 4:00 p.m. | ||
| Wed., 1/7 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Fri., 1/9 | V Boys Basketball | Harding | Home - DHS Main Gym [Directions] | L 46-58 | ||
| Fri., 1/9 | JV Boys Basketball | Harding | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/9 | FR Boys Basketball | Harding | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/9 | V Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 86-54 | ||
| Fri., 1/9 | JV Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/10 | V Boys Ice Hockey | Trumbull | Home - Darien Ice Rink [Directions] | W 5-4 | ||
| Sat., 1/10 | V Boys Indoor Track | Elm City Invite @ Hillhouse HS | Away | 9:00 a.m. | ||
| Sat., 1/10 | V Boys Indoor Track | Developmental Meet @ Wilton v NC, Greenwich, Westhill, Warde, St Joe's | Away | 9:30 a.m. | ||
| Sat., 1/10 | V Wrestling | Bunnell, New Canaan, Fairfield Prep, Platt Tech | Home - DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/10 | V Girls Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Sat., 1/10 | V Girls Indoor Track | Developmental Meet @ Wilton v NC, Greenwich, Westhill, Warde, St Joe's | Away | 9:30 a.m. | ||
| Mon., 1/12 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 1-4 | 4:00 p.m. | |
| Tue., 1/13 | V Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | W 53-44 | ||
| Tue., 1/13 | JV Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/13 | FR Boys Basketball | Fairfield Warde | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/13 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 59-70 | 4:00 p.m. | |
| Tue., 1/13 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | Cancelled | ||
| Tue., 1/13 | V Girls Gymnastics | Fairfield Warde, Fairfield Ludlowe | Away - Gymnastics & Cheer Academy [Directions] | Darien: 128.850 Fairfield Ludlowe: 127.60 Fairfield Warde: 64.6 | 5:00 p.m. | Pickup @ Darien YMCA |
| Wed., 1/14 | V Boys Swimming and Diving | Trumbull | Home - Darien YMCA [Directions] | Trumbull 62 Darien 90 | ||
| Wed., 1/14 | V Wrestling | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 6:00 p.m. | 4:15 p.m. | |
| Wed., 1/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 5:00 p.m. | ||
| Thu., 1/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice Rink [Directions] | 5:40 p.m. | ||
| Fri., 1/16 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 43-40 | ||
| Fri., 1/16 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Fri., 1/16 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:45 p.m. | ||
| Fri., 1/16 | V Boys Indoor Track | Yale Invitational, Coxe Cage | Away | 1:00 p.m. | ||
| Fri., 1/16 | V Girls Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | W 76-26 | ||
| Fri., 1/16 | JV Girls Basketball | Brien McMahon | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/16 | V Girls Indoor Track | Yale Invitational | Away | TBA | ||
| Sat., 1/17 | V Boys Ice Hockey | New Canaan | Home - Darien Ice Rink [Directions] | W 4-2 | ||
| Sat., 1/17 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:50 p.m. | ||
| Sat., 1/17 | V Boys Indoor Track | Developmental Meet @ Staples v NC, Greenwich, Ludlowe, Warde, St Joe's | Away | 10:00 a.m. | ||
| Sat., 1/17 | V Boys Indoor Track | Yale Invitational | Away | 7:30 a.m. | ||
| Sat., 1/17 | V Wrestling | Spartan Duels @ Maloney | Away | 10:00 a.m. | 8:00 a.m. | |
| Sat., 1/17 | V Girls Gymnastics | Greenwich | Home - Darien YMCA [Directions] | Darien 128.95 Greenwich 78.6 | ||
| Sat., 1/17 | V Girls Ice Hockey | Simsbury | Away - ISCC [Directions] | 6:00 p.m. | ||
| Sat., 1/17 | V Girls Indoor Track | Developmental Meet @ Staples v NC, Greenwich, Ludlowe, Warde, St Joe's | Away | 10:00 a.m. | ||
| Sat., 1/17 | V Girls Indoor Track | Yale Invitational | Away | TBA | ||
| Tue., 1/20 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | L 36-48 | ||
| Tue., 1/20 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Tue., 1/20 | FR Boys Basketball | Trinity Catholic | Away | 4:00 p.m. | ||
| Tue., 1/20 | V Girls Basketball | Trinity Catholic | Home - DHS Main Gym [Directions] | W 54-40 | ||
| Tue., 1/20 | JV Girls Basketball | Trinity Catholic | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/21 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | W 6-3 | 4:00 p.m. | |
| Wed., 1/21 | V Boys Swimming and Diving | Greenwich | Home - Darien YMCA [Directions] | Darien 74 Greenwich 109 | ||
| Wed., 1/21 | V Wrestling | Stamford | Away - Stamford High Aux Gym [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Wed., 1/21 | V Co-ed Alpine Skiing | Race vs Cheshire, Prep, Staples, Westbrook, LH @ Southington | Away | 4:00 p.m. | ||
| Wed., 1/21 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden [Directions] | 3:30 p.m. | ||
| Thu., 1/22 | V Boys Basketball | Hamden | Away - HHS Gym [Directions] | L 39-62 | ||
| Thu., 1/22 | JV Boys Basketball | Hamden | Away - HHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/22 | FR Boys Basketball | Hamden | Away - HHS Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/22 | V Girls Gymnastics | Staples | Away - Wilton High School Aux. Gym [Directions] | Darien 132.85 Staples 119.95 | @ Wilton | |
| Fri., 1/23 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | Norwalk/McMahon 83 Darien 95 | ||
| Sat., 1/24 | V Boys Indoor Track | Developmental Meet @ Staples v Ridgefield, St Joe's Ludlowe, Warde, & Westhill | Away | Cancelled | 8:30 a.m. | |
| Sat., 1/24 | V Wrestling | Valley of Champions @ Oxford | Away | Cancelled | 7:00 a.m. | |
| Sat., 1/24 | V Girls Indoor Track | Developmental Meet @ Staples v Ridgefield, Ludlowe, Warde, & Westhill | Away | Cancelled | 8:30 a.m. | |
| Sun., 1/25 | JV Boys Ice Hockey | New Canaan (Scrim.) | Home - Darien Ice Rink [Directions] | 9:00 p.m. | ||
| Sun., 1/25 | V Boys Indoor Track | SCC Coach's Invitational @ Hillhouse HS | Away | 12:00 p.m. | ||
| Sun., 1/25 | V Girls Indoor Track | SCC Coaches Meet @ Hillhouse HS | Away | 4:45 p.m. | ||
| Tue., 1/27 | JV Girls Basketball | Bassick | Home - DHS Main Gym [Directions] | Cancelled | ||
| Wed., 1/28 | V Boys Basketball | Bassick | Away [Directions] | L 37-60 | ||
| Wed., 1/28 | JV Boys Basketball | Bassick | Away [Directions] | 5:15 p.m. | ||
| Wed., 1/28 | FR Boys Basketball | Bassick | Away [Directions] | 4:00 p.m. | ||
| Wed., 1/28 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | Staples 92 Darien 94 | ||
| Wed., 1/28 | V Co-ed Alpine Skiing | Race vs Greenwich, Amity,St. Lukes, Litchfield, NC, Hopkins @ Southington | Away | 4:00 p.m. | ||
| Wed., 1/28 | V Girls Basketball | Bassick | Home - DHS Main Gym [Directions] | W 66-31 | ||
| Wed., 1/28 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice Rink [Directions] | 7:40 p.m. | ||
| Thu., 1/29 | V Wrestling | Norwalk | Home - DHS - South Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/29 | V Girls Gymnastics | New Milford | Away - New Milford High School [Directions] | 135.1 New Milford 134.4 Darien | ||
| Thu., 1/29 | V Girls Ice Hockey | Hall/Conard | Home - Darien Ice Rink [Directions] | 5:40 p.m. | ||
| Fri., 1/30 | V Boys Basketball | Stamford | Home - DHS Main Gym [Directions] | L 37-68 | ||
| Fri., 1/30 | JV Boys Basketball | Stamford | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/30 | FR Boys Basketball | Stamford | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/30 | V Boys Indoor Track | FCIAC Eastern Division Championship @ Wilton | Away | 5:30 p.m. | 3:30 p.m. | |
| Fri., 1/30 | V Boys Swimming and Diving | Westhill/Stamford | Away [Directions] | Westhill/Stamford 77 Darien 107 | 2:00 p.m. | |
| Fri., 1/30 | V Girls Basketball | Stamford | Away - Stamford High School [Directions] | L 45-64 | 2:30 p.m. | |
| Fri., 1/30 | JV Girls Basketball | Stamford | Away - Stamford High School [Directions] | Cancelled | ||
| Fri., 1/30 | V Girls Indoor Track | FCIAC Eastern Division Championship @ Wilton | Away | 5:30 p.m. | 3:30 p.m. | |
| Sat., 1/31 | V Boys Ice Hockey | Trinity Catholic | Home - Darien Ice Rink [Directions] | W 8-2 | ||
| Sat., 1/31 | V Wrestling | East Hartford, Granby Memorial, Northwestern, RHAM | Away [Directions] | 10:00 a.m. | 7:30 a.m. | |
| Sat., 1/31 | V Girls Gymnastics | Wilton | Home - Darien YMCA [Directions] | Darien 131.55 Wilton 127.90 | ||
| Tue., 2/3 | V Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | L 48-68 | ||
| Tue., 2/3 | JV Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/3 | FR Boys Basketball | Trumbull | Home - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/3 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | T 3-3 | 2:30 p.m. | |
| Tue., 2/3 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 37-64 | 2:30 p.m. | |
| Tue., 2/3 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 2/3 | V Girls Ice Hockey | Simsbury | Home - Darien Ice Rink [Directions] | 5:10 p.m. | ||
| Wed., 2/4 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | W 4-1 | 3:45 p.m. | |
| Wed., 2/4 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | Wilton 82 Darien 102 | 2:00 p.m. | |
| Wed., 2/4 | V Wrestling | Trumbull | Home - DHS - South Gym [Directions] | 5:00 p.m. | ||
| Thu., 2/5 | V Boys Indoor Track | FCIAC Championships @ Hillhouse HS | Away | 4:30 p.m. | 1:30 p.m. | |
| Thu., 2/5 | V Co-ed Alpine Skiing | Race vs Farmington, Pomperaug, Branford, Wilton, Westhill @ Southington | Away | 4:00 p.m. | 1:45 p.m. | |
| Thu., 2/5 | V Girls Indoor Track | FCIAC Championships @ Hillhouse | Away | 4:30 p.m. | 1:30 p.m. | |
| Fri., 2/6 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | L 40-45 | 4:00 p.m. | |
| Fri., 2/6 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | 4:00 p.m. | |
| Fri., 2/6 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 2/6 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Darien YMCA [Directions] | Fairfield Ludlowe 67 Darien 96 | 1:50 p.m. | |
| Fri., 2/6 | V Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | L 58-71 | ||
| Fri., 2/6 | JV Girls Basketball | Greenwich | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/7 | V Boys Ice Hockey | Wilton | Home - Darien Ice Rink [Directions] | W 7-3 | ||
| Sat., 2/7 | V Boys Indoor Track | FCIAC JV Invitational @ Staples | Away | 10:00 a.m. | 8:30 a.m. | |
| Sat., 2/7 | V Wrestling | Lawmen Invitational @ Jonathan Law | Away | 10:00 a.m. | 7:15 a.m. | |
| Sat., 2/7 | V Girls Gymnastics | New Canaan, Westhill | Home - Darien YMCA [Directions] | Darien; 135.70 New Canaan: 111.30 Westhill: 91.30 Stamford: 56.85 | ||
| Sat., 2/7 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill [Directions] | 6:30 p.m. | 5:00 p.m. | |
| Sat., 2/7 | V Girls Indoor Track | FCIAC JV Invitational | Away | 10:00 a.m. | ||
| Tue., 2/10 | V Boys Basketball | Wilton | Home - DHS Main Gym [Directions] | L 61-68 | ||
| Tue., 2/10 | JV Boys Basketball | Wilton | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/10 | FR Boys Basketball | Wilton | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/10 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Tue., 2/10 | V Wrestling | Harding/Bassick/Bridgeport Central | Away - Harding-Auxiliary Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 2/10 | V Girls Basketball | Wilton | Away - Wilton High School Field House [Directions] | L 24-67 | 3:00 p.m. | |
| Tue., 2/10 | JV Girls Basketball | Wilton | Away - Wilton High School Field House [Directions] | 4:00 p.m. | 3:00 p.m. | |
| Tue., 2/10 | V Girls Gymnastics | Trumbull | Away - Greenwich [Directions] | Darien: 131.25 Trumbull: 132.85 | 3:30 p.m. | PICKUP/RETURN FROM DARIEN YMCA |
| Tue., 2/10 | V Girls Gymnastics | Greenwich, Trumbull | Away - Greenwich YWCA [Directions] | 5:00 p.m. | ||
| Tue., 2/10 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 2:50 p.m. | ||
| Wed., 2/11 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | W 9-3 | 2:00 p.m. | |
| Wed., 2/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice Rink [Directions] | 7:40 p.m. | ||
| Thu., 2/12 | JV Boys Ice Hockey | Stamford | Home - Stamford Twin Rinks [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 2/12 | V Co-ed Alpine Skiing | Race vs Fairfield, Barlow, Danbury, Guilford, Weston @ Southington | Away | 4:00 p.m. | 1:45 p.m. | |
| Fri., 2/13 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 51-62 | 3:45 p.m. | |
| Fri., 2/13 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | 3:45 p.m. | |
| Fri., 2/13 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 2/13 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:30 p.m. | |
| Fri., 2/13 | V Boys Swimming and Diving | Danbury | Home - Darien YMCA [Directions] | Cancelled | ||
| Fri., 2/13 | V Wrestling | FCIAC | Away | 4:00 p.m. | 1:55 p.m. | |
| Fri., 2/13 | V Girls Basketball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | W 51-44 | ||
| Fri., 2/13 | JV Girls Basketball | Fairfield Ludlowe | Home - DHS Main Gym [Directions] | Cancelled | ||
| Fri., 2/13 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Rinks at Shelton [Directions] | 4:00 p.m. | 1:45 p.m. | |
| Fri., 2/13 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:00 p.m. | |
| Sat., 2/14 | V Boys Ice Hockey | Norwalk | Home - Darien Ice Rink [Directions] | W 9-1 | ||
| Sat., 2/14 | V Wrestling | FCIAC | Away | 10:00 a.m. | ||
| Sat., 2/14 | V Girls Gymnastics | FCIAC Championships @ Law HS | Away | 134.20 | ||
| Sun., 2/15 | JV Boys Ice Hockey | New Canaan (Scrim.) | Away - Darien Ice Rink [Directions] | Cancelled | ||
| Mon., 2/16 | V Boys Basketball | Staples | Home - DHS Main Gym [Directions] | W 61-50 | ||
| Mon., 2/16 | JV Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/16 | FR Boys Basketball | Staples | Home - DHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 2/16 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice Rink [Directions] | W Forfeit | ||
| Mon., 2/16 | JV Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | 11:00 a.m. | 2:00 p.m. | |
| Mon., 2/16 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 41-52 | ||
| Mon., 2/16 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | Cancelled | ||
| Tue., 2/17 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Rink [Directions] | 8:00 p.m. | 6:15 p.m. | |
| Wed., 2/18 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | L 47-54 | 2:15 p.m. | |
| Wed., 2/18 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:30 p.m. | 2:15 p.m. | |
| Wed., 2/18 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 2:00 p.m. | 12:45 p.m. | |
| Wed., 2/18 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Darien Ice Rink [Directions] | W 3-1 | ||
| Wed., 2/18 | V Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | W 61-48 | ||
| Wed., 2/18 | JV Girls Basketball | New Canaan | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/18 | V Girls Ice Hockey | Pomfret | Away - Pomfret School | 2:00 p.m. | 10:30 a.m. | |
| Fri., 2/20 | V Wrestling | Class L | Away | 4:00 p.m. | ||
| Sat., 2/21 | V Boys Ice Hockey | West Haven Coop | Home - Darien Ice Rink [Directions] | W 4-2 | ||
| Sat., 2/21 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/21 | V Wrestling | Class L | Away | 9:00 a.m. | ||
| Sat., 2/21 | V Girls Gymnastics | Ro Carlucci Invitational @ GCA | Away | TBA | ||
| Sat., 2/21 | V Girls Ice Hockey | Greenwich Academy | Home - Darien Ice Rink [Directions] | Cancelled | ||
| Sat., 2/21 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/23 | V Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | L 39-65 | ||
| Mon., 2/23 | JV Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/23 | FR Boys Basketball | Ridgefield | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/23 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | W 5-3 | 1:45 p.m. | |
| Mon., 2/23 | JV Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 5:45 p.m. | 3:30 p.m. | |
| Wed., 2/25 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | L 65-78 | ||
| Wed., 2/25 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/25 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Wed., 2/25 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | W 5-0 | ||
| Wed., 2/25 | V Girls Ice Hockey | FCIAC Semi-Finals @ DIR | Home - Darien Ice Rink [Directions] | 7:40 p.m. | ||
| Fri., 2/27 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | ||
| Fri., 2/27 | V Wrestling | Opens | Away | 4:00 p.m. | ||
| Fri., 2/27 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | ||
| Sat., 2/28 | V Boys Ice Hockey | FCIAC Playdowns @ Terry Conners | Away | Cancelled | Games @ 2:20 and 4:20 p.m. | |
| Sat., 2/28 | V Wrestling | Opens | Away | 9:00 a.m. | ||
| Sat., 2/28 | V Girls Gymnastics | CIAC Divisionals | Away | 3rd Place M Division. 1st Place specifically on the Beam event in M Division. 5th place overall in the State. | ||
| Sat., 2/28 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 12:20 p.m. | ||
| Mon., 3/2 | V Girls Ice Hockey | State Quarter-Finals vs Ridgefield | Home - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Tue., 3/3 | V Girls Basketball | Norwich Free Academy | Away - Alumni Gym [Directions] | 6:00 p.m. | TBD | Class LL First Round |
| Wed., 3/4 | V Boys Ice Hockey | FCIAC Semi-Finals @ Terry Conners | Away | TBA | Games @ 4:00 and 6:30 p.m. | |
| Wed., 3/4 | V Girls Ice Hockey | Tentative State Semi-Finals @ Shelton Rinks | Away | TBA | 5:30 or 7:30 at Shelton Rinks | |
| Sat., 3/7 | V Boys Ice Hockey | FCIAC Final vs Greenwich @ Terry Conners | Away | 3:30 p.m. | ||
| Sat., 3/7 | V Girls Gymnastics | CIAC Opens @ New Milford HS | Away | 9:00 a.m. | 7:15 a.m. | |
| Sat., 3/7 | V Girls Ice Hockey | Tentative State Finals @ Terry Conners Rinks | Away | Cancelled | @ Terry Connors Rink | |
| Wed., 3/11 | V Boys Ice Hockey | CIACS - Round 1 | Home - Darien Ice Rink [Directions] | 7:00 p.m. | ||
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Class L Diving @ Middletown HS | Away | 5:30 p.m. | TBD | Warmup @ 4:00 p.m. |
| Fri., 3/13 | V Boys Indoor Track | New Balance Indoor Nationals @ 168 St Armory, Manhattan, NY | Away | TBA | Dates include March 13, 14, 15 | |
| Sat., 3/14 | V Boys Ice Hockey | Ridgefield | Away [Directions] | 2:00 p.m. | CIAC Quarter-Final @ Webster Bank Arena- Bridgeport | |
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Class L @ Kennedy HS, Waterbury, CT | Away | 4:30 p.m. | 12:45 p.m. | Warmup @ 2:30 p.m. |
| Sat., 3/14 | V Girls Gymnastics | New Englands | Away | TBA | ||
| Sun., 3/15 | V Boys Rugby | @ Fordham University Murphy Field | Away | 10:00 a.m. | 9:00 a.m. | |
| Tue., 3/17 | V Boys Swimming and Diving | CIAC Class L Final @ Wesleyan | Away | 1:30 p.m. | 11:15 a.m. | Warmup @ 12:45 p.m. |
| Wed., 3/18 | V Boys Ice Hockey | Xavier | Away [Directions] | 7:30 p.m. | Div I Semi-Finala @ Ingalls Rink- Yale | |
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Class L Open Dive @ Middletown HS | Away | 5:30 p.m. | TBD | Warmup @ 4:00 p.m. |
| Sat., 3/21 | V Boys Ice Hockey | CIAC Championship vs Greenwich @ Ingalls Rink, Yale University | Away | 2:00 p.m. | 11:30 a.m. | |
| Wed., 3/25 | V Boys Lacrosse | Blue v White | Home - DHS Turf #2 [Directions] | 3:30 p.m. | ||
| Wed., 3/25 | V Co-ed Sailing | Ludlowe, Prep, Stamford | Home [Directions] | TBA | @ Noroton | |
| Thu., 3/26 | V Girls Lacrosse | Rye (NY) (Scrim.) | Away | 4:30 p.m. | ||
| Fri., 3/27 | V Girls Lacrosse | Yorktown (NY) (Scrim.) | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 3/27 | V Softball | Mamaroneck (NY) (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | ||
| Sat., 3/28 | V Baseball | Monadnock Regional HS, NH | Home - DHS Baseball Varsity Field [Directions] | TBA | ||
| Sat., 3/28 | V Boys Lacrosse | Jamboree | Home - DHS Stadium Field [Directions] | 8:00 a.m. | also center oval field | |
| Sat., 3/28 | V Boys Volleyball | Darien PlayDay | Home - DHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 3/28 | V Softball | Play-Day vs. Stamford, Westhill & NC | Home - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | ||
| Tue., 3/31 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Away | 3:30 p.m. | 2:25 p.m. | |
| Wed., 4/1 | V Baseball | Wilton (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 3:45 p.m. | ||
| Wed., 4/1 | V Boys Lacrosse | Salisbury School (Scrim.) | Home - DHS Turf #2 [Directions] | 3:30 p.m. | ||
| Wed., 4/1 | V Co-ed Sailing | Greenwich Academy, Staples | Away | TBA | @ Staples | |
| Wed., 4/1 | V Girls Lacrosse | Wilton (Scrim.) | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 4/2 | V Baseball | New Canaan (Scrim.) | Home - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Thu., 4/2 | V Boys Rugby | Fairfield Prep | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Thu., 4/2 | V Softball | Westhill (Scrim.) | Home - DHS Softball Varsity Field [Directions] | 3:15 p.m. | ||
| Sat., 4/4 | V Baseball | Jamboree vs Stratford & Warde | Home - DHS Baseball Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 4/4 | V Boys Lacrosse | Jamboree | Home - DHS Stadium Field [Directions] | 8:00 a.m. | also center oval | |
| Sat., 4/4 | V Boys Volleyball | Pre-Season Boys Volleyball Playday @ Ludlowe HS | Away | 8:30 a.m. | TBD | |
| Sat., 4/4 | V Co-ed Sailing | Brunswick, Greenwich, Xavier, Hotchkiss, Xavier, Falmouth, Nantucket | Away | TBA | @ Indian Harbor YC | |
| Sat., 4/4 | V Softball | Play-Day v Conville, NH, Branford, East Lyme | Home - DHS Softball Varsity Field [Directions] | 12:30 p.m. | ||
| Mon., 4/6 | V Softball | New Canaan (Scrim.) | Home - DHS Softball Varsity Field [Directions] | 3:15 p.m. | ||
| Wed., 4/8 | V Baseball | New Fairfield | Home - DHS Baseball Varsity Field [Directions] | L 2-4 | ||
| Wed., 4/8 | JV Baseball | New Fairfield | Home - DHS Baseball JV Field [Directions] | 4:15 p.m. | ||
| Wed., 4/8 | V Boys Lacrosse | Westhill | Home - DHS Turf #2 [Directions] | W 21-0 | ||
| Wed., 4/8 | JV Boys Lacrosse | Westhill | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Wed., 4/8 | V Boys Tennis | Bridgeport Central | Away - Central H.S. Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/8 | V Boys Volleyball | Newtown | Away - Newtown High School Gymnasium [Directions] | W 3-0 | ||
| Wed., 4/8 | V Co-ed Sailing | Greenwich, Staples | Away | TBA | @ Grass Island | |
| Wed., 4/8 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | W 11-5 | ||
| Wed., 4/8 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:15 p.m. | ||
| Wed., 4/8 | V Girls Outdoor Track | St. Joseph, Weston | Home - DHS Track [Directions] | 4:00 p.m. | ||
| Wed., 4/8 | V Softball | Harding | Away - Beardsley Park - Softball [Directions] | W 17-0(5) | ||
| Wed., 4/8 | V Girls Tennis | Bridgeport Central | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/8 | JV Girls Tennis | Staples | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Thu., 4/9 | FR Boys Lacrosse | Wilton | Home - Middlesex Lower Field [Directions] | 4:30 p.m. | ||
| Thu., 4/9 | V Boys Outdoor Track | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Thu., 4/9 | V Boys Rugby | Fairfield | Home - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 4/9 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | L 3-4 | ||
| Thu., 4/9 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | W 7-1 | ||
| Thu., 4/9 | V Boys Volleyball | AAE-International | Away - Learning Corridor Gym [Directions] | W 3-0 | ||
| Thu., 4/9 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | Darien 188 Wilton 200 | ||
| Thu., 4/9 | JV Girls Tennis | Fairfield Ludlowe | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Fri., 4/10 | V Baseball | Westhill | Home - DHS Baseball Varsity Field [Directions] | W 5-4 | ||
| Fri., 4/10 | JV Boys Lacrosse | Wilton | Home - Middlesex Lower Field [Directions] | Cancelled | ||
| Fri., 4/10 | V Boys Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | W 3-0 | ||
| Fri., 4/10 | JV Boys Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:30 p.m. | ||
| Fri., 4/10 | FR Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 4/10 | FR Softball | Westhill | Away - Roxbury Elementary School [Directions] | Cancelled | ||
| Sat., 4/11 | V Baseball | Norwich Free Academy | Away - Dodd Stadium [Directions] | L 0-6 | @ Dodd Stadium | |
| Sat., 4/11 | JV Baseball | Norwich Free Academy | Away - Dickenman Field [Directions] | Cancelled | ||
| Sat., 4/11 | FR Baseball | Joel Barlow | Home - DHS Baseball Varsity Field [Directions] | 11:00 a.m. | ||
| Sat., 4/11 | V Boys Lacrosse | Niskayuna (NY) | Away | W 11-5 | @ Union College | |
| Sat., 4/11 | JV Boys Lacrosse | Fairfield Prep | Home - DHS Turf #2 [Directions] | 10:30 a.m. | ||
| Sat., 4/11 | V Girls Lacrosse | Garden City (NY) | Home - DHS Stadium Field [Directions] | L 8-9 | ||
| Sat., 4/11 | V Softball | Masuk | Away - Masuk Upper Softball Field [Directions] | W 12-5 | ||
| Sun., 4/12 | V Softball | Westhill | Home - DHS Softball Varsity Field [Directions] | W 2-1 | ||
| Sun., 4/12 | JV Softball | Westhill | Home - DHS Softball JV Field [Directions] | 12:30 p.m. | ||
| Mon., 4/13 | V Baseball | Bridgeport Central | Home - DHS Baseball Varsity Field [Directions] | W 27-5 | ||
| Mon., 4/13 | JV Baseball | Bridgeport Central | Home - DHS Baseball JV Field [Directions] | 1:00 p.m. | ||
| Mon., 4/13 | V Boys Tennis | Staples | Home - DHS Tennis Courts [Directions] | L 1-6 | ||
| Mon., 4/13 | JV Boys Tennis | Staples | Home - Cherry Lawn Park [Directions] | 2:00 p.m. | ||
| Mon., 4/13 | V Boys Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Mon., 4/13 | JV Boys Volleyball | Fairfield Warde | Home - DHS Main Gym [Directions] | 12:30 p.m. | ||
| Mon., 4/13 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | W 23-0 | ||
| Mon., 4/13 | JV Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/13 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 3-4 | ||
| Tue., 4/14 | FR Baseball | Westhill | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 4/14 | V Boys Lacrosse | Trinity Catholic | Home - DHS Stadium Field [Directions] | W 20-0 | ||
| Tue., 4/14 | JV Boys Lacrosse | Bridgeport Central | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 4/14 | FR Boys Lacrosse | Ridgefield | Home - DHS Turf #2 [Directions] | 4:30 p.m. | ||
| Tue., 4/14 | V Boys Tennis | St. Joseph | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/14 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 20-1 | ||
| Tue., 4/14 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 11:30 a.m. | ||
| Tue., 4/14 | V Girls Tennis | St. Joseph | Away - St. Joseph High School [Directions] | W 7-0 | ||
| Wed., 4/15 | V Baseball | St. Joseph | Away - St. Joseph High School [Directions] | W 17-2 | ||
| Wed., 4/15 | JV Baseball | St. Joseph | Away - Madison Middle School, Trumbull [Directions] | 1:00 p.m. | ||
| Wed., 4/15 | FR Baseball | St. Joseph | Home - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | ||
| Wed., 4/15 | FR Boys Lacrosse | Fairfield Prep | Home - DHS Turf #2 [Directions] | 11:00 a.m. | ||
| Wed., 4/15 | V Girls Lacrosse | Manhassett (NY) | Away | L 11-14 | ||
| Wed., 4/15 | JV Girls Lacrosse | Manhassett (NY) | Away | 4:15 p.m. | ||
| Wed., 4/15 | V Softball | St. Joseph | Home - DHS Softball Varsity Field [Directions] | L 4-5 | ||
| Wed., 4/15 | JV Softball | St. Joseph | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Thu., 4/16 | JV Baseball | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Thu., 4/16 | FR Girls Lacrosse | New Canaan | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Fri., 4/17 | V Baseball | Danbury | Home - DHS Baseball Varsity Field [Directions] | W 5-4 | ||
| Fri., 4/17 | JV Baseball | Danbury | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Fri., 4/17 | FR Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 1:00 p.m. | ||
| Fri., 4/17 | V Boys Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 3-0 | ||
| Fri., 4/17 | V Girls Lacrosse | St. Joseph | Home - DHS Stadium Field [Directions] | W 20-0 | ||
| Fri., 4/17 | JV Girls Lacrosse | St. Joseph | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 4/17 | V Softball | Danbury | Away - Danbury High School Varsity Softball Field [Directions] | W 6-1 | ||
| Fri., 4/17 | JV Softball | Danbury | Away - Danbury High School Junior Varsity Softball Field [Directions] | 1:00 p.m. | ||
| Sat., 4/18 | V Boys Lacrosse | Manhassett (NY) | Away | W 7-3 | Battle of the Sound @ Garden City HS | |
| Sat., 4/18 | JV Boys Lacrosse | Manhassett @ Garden City HS | Away | 11:00 a.m. | ||
| Sat., 4/18 | FR Boys Lacrosse | Don Bosco (NJ) (Scrim.) | Home - DHS Turf #2 [Directions] | 11:00 a.m. | ||
| Mon., 4/20 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-1 | ||
| Mon., 4/20 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 4/21 | V Baseball | Harding | Home - DHS Baseball Varsity Field [Directions] | W 16-0 | ||
| Tue., 4/21 | JV Baseball | Harding | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Boys Golf | Danbury | Home - CC of Darien [Directions] | Darien 168 Danbury 171 | ||
| Tue., 4/21 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | W 13-5 | ||
| Tue., 4/21 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Boys Outdoor Track | Bassick, Trumbull | Home - DHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Boys Tennis | Fairfield Warde | Away [Directions] | W 6-1 | ||
| Tue., 4/21 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | W 6-1 | ||
| Tue., 4/21 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Darien 207 Warde 207 | ||
| Tue., 4/21 | V Girls Lacrosse | Brien McMahon | Home - DHS Turf #2 [Directions] | W 20-1 | ||
| Tue., 4/21 | JV Girls Lacrosse | Brien McMahon | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Tue., 4/21 | V Girls Outdoor Track | Trumbull, Bassick | Away - McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Softball | Fryeburg (ME) | Home - DHS Softball Varsity Field [Directions] | W 6-0 | ||
| Tue., 4/21 | JV Softball | Fryeburg (ME) | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Girls Tennis | Fairfield Warde | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/21 | JV Girls Tennis | Fairfield Warde | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Wed., 4/22 | V Baseball | Fairfield Warde | Home - DHS Baseball Varsity Field [Directions] | W 6-1 | ||
| Wed., 4/22 | JV Baseball | Fairfield Warde | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/22 | JV Boys Golf | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | Cancelled | 2:30 p.m. | @ Smith Richardson |
| Wed., 4/22 | FR Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Wed., 4/22 | V Boys Volleyball | Bassick | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Wed., 4/22 | JV Boys Volleyball | Bassick | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/22 | V Co-ed Sailing | Brunswick | Away | TBA | @ Indian Harbor YC | |
| Wed., 4/22 | V Girls Golf | New Canaan | Home - Weeburn Country Club [Directions] | Darien 207 NC 243 | ||
| Wed., 4/22 | FR Girls Lacrosse | Greenwich | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Wed., 4/22 | V Girls Tennis | Fairfield Ludlowe | Home - DHS Tennis Courts [Directions] | L 2-4 | ||
| Thu., 4/23 | V Boys Golf | St. Joseph, Fairfield Warde | Away [Directions] | Darien 162 St. Joseph 198 | ||
| Thu., 4/23 | V Boys Lacrosse | Ridgefield | Home - DHS Turf #2 [Directions] | W 10-9 | ||
| Thu., 4/23 | JV Boys Lacrosse | Ridgefield | Home - DHS Turf #2 [Directions] | 6:15 p.m. | ||
| Thu., 4/23 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 6-1 | ||
| Thu., 4/23 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 2-3 | ||
| Thu., 4/23 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | ||
| Thu., 4/23 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | Darien 203 Danbury 202 | ||
| Thu., 4/23 | JV Girls Golf | Greenwich | Away [Directions] | Cancelled | ||
| Thu., 4/23 | V Girls Lacrosse | Notre Dame Academy (MA) | Home - DHS Stadium Field [Directions] | W 14-11 | ||
| Thu., 4/23 | JV Girls Lacrosse | Greenwich Academy | Away | 4:00 p.m. | ||
| Thu., 4/23 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | W 9-1 | ||
| Thu., 4/23 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | ||
| Thu., 4/23 | V Girls Tennis | Trumbull | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/23 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Fri., 4/24 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-2 | ||
| Fri., 4/24 | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | 4:30 p.m. | ||
| Fri., 4/24 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:45 p.m. | ||
| Fri., 4/24 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away | 5:30 p.m. | 3:30 p.m. | |
| Fri., 4/24 | V Boys Rugby | Greenwich B | Away | Cancelled | ||
| Fri., 4/24 | JV Boys Tennis | Greenwich | Home - Cherry Lawn Park [Directions] | W 5-1 | ||
| Fri., 4/24 | FR Girls Lacrosse | Wilton | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Fri., 4/24 | V Softball | Brien McMahon | Home - DHS Softball Varsity Field [Directions] | W 15-0 | ||
| Fri., 4/24 | JV Softball | Brien McMahon | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Sat., 4/25 | FR Baseball | Brien McMahon | Home - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | ||
| Sat., 4/25 | JV Boys Lacrosse | Don Bosco (NJ) | Home - DHS Turf #2 [Directions] | Cancelled | ||
| Sat., 4/25 | V Boys Outdoor Track | Danbury | Away [Directions] | 9:00 a.m. | 7:00 a.m. | |
| Sat., 4/25 | V Co-ed Sailing | O'Day Qualifiers Fleet @ Hotchkiss | Away | TBA | ||
| Sat., 4/25 | V Girls Outdoor Track | Danbury | Away [Directions] | 9:00 a.m. | 7:00 a.m. | |
| Sun., 4/26 | V Co-ed Sailing | O'Day Finas @ Ida Lewis- Newport | Away | TBA | ||
| Mon., 4/27 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | W 9-0 | ||
| Mon., 4/27 | JV Baseball | Trinity Catholic | Away - Barrett Field @ Belltown Park | 4:00 p.m. | ||
| Mon., 4/27 | FR Baseball | Trinity Catholic | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/27 | V Boys Golf | Fairfield Warde, Stamford | Home - Wee Burn CC [Directions] | Darien 158 Warde 177 Stamford 229 | ||
| Mon., 4/27 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 19-5 | ||
| Mon., 4/27 | JV Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Mon., 4/27 | FR Boys Lacrosse | Daniel Hand | Away - Janssen Field/DHHS Campus [Directions] | 4:45 p.m. | ||
| Mon., 4/27 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | W 4-3 | ||
| Mon., 4/27 | JV Boys Tennis | Wilton | Away - Allen's Field [Directions] | W 6-3 | ||
| Mon., 4/27 | V Boys Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | W 3-1 | ||
| Mon., 4/27 | JV Boys Volleyball | St. Joseph | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/27 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Darien 206 Greenwich 186 | ||
| Mon., 4/27 | JV Girls Golf | Greenwich | Away - Greenwich Country Club [Directions] | 3:30 p.m. | ||
| Mon., 4/27 | JV Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:30 p.m. | ||
| Mon., 4/27 | FR Girls Lacrosse | Norwalk | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Mon., 4/27 | V Girls Outdoor Track | New Canaan, Harding | Home - DHS Track [Directions] | 4:00 p.m. | ||
| Mon., 4/27 | V Softball | Trinity Catholic | Home - DHS Softball Varsity Field [Directions] | W 14-0 | ||
| Mon., 4/27 | JV Softball | Ridgefield | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/27 | V Girls Tennis | Wilton | Home - DHS Tennis Courts [Directions] | W 5-2 | ||
| Mon., 4/27 | JV Girls Tennis | Wilton | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Tue., 4/28 | V Boys Golf | Harding, Bridgeport Central | Away [Directions] | Darien 163 Harding 239 Central forfeit Central - forfeit | ||
| Tue., 4/28 | V Boys Outdoor Track | Wilton, New Canaan, Bassick | Away [Directions] | Cancelled | ||
| Tue., 4/28 | V Boys Tennis | Ridgefield | Home - DHS Tennis Courts [Directions] | W 5-2 | ||
| Tue., 4/28 | JV Boys Tennis | Ridgefield | Home - Cherry Lawn Park [Directions] | W 6-0 | ||
| Tue., 4/28 | V Girls Golf | Trumbull | Home - CC of Darien [Directions] | Darien 211 Trumbull 230 | ||
| Tue., 4/28 | V Girls Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | W 15-5 | ||
| Tue., 4/28 | JV Girls Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/28 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/28 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/29 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | Darien 162 Trinity 192 | ||
| Wed., 4/29 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Wed., 4/29 | V Boys Outdoor Track | New Canaan, Harding | Away - Wilton High School [Directions] | Cancelled | ||
| Wed., 4/29 | V Boys Tennis | Greenwich | Home - DHS Tennis Courts [Directions] | W 4-3 | ||
| Wed., 4/29 | V Boys Volleyball | Staples | Home - DHS Main Gym [Directions] | W 3-1 | ||
| Wed., 4/29 | JV Boys Volleyball | Staples | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/29 | V Co-ed Sailing | Prep, GFA, Brunswick | Away | TBA | @ Pequot YC | |
| Wed., 4/29 | JV Girls Golf | Trumbull | Home - Woodway CC [Directions] | 3:15 p.m. | ||
| Wed., 4/29 | FR Girls Lacrosse | Greenwich Academy | Away | 4:00 p.m. | ||
| Wed., 4/29 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | W 5-3 | ||
| Thu., 4/30 | JV Baseball | Fairfield Warde | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 4/30 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 3:30 p.m. | ||
| Thu., 4/30 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Ludlowe 161 Darien 169 | ||
| Thu., 4/30 | JV Boys Golf | Staples | Home - Woodway CC [Directions] | 3:00 p.m. | ||
| Thu., 4/30 | V Boys Lacrosse | Yorktown (NY) | Home - DHS Turf #2 [Directions] | W 15-3 | ||
| Thu., 4/30 | JV Boys Lacrosse | Yorktown (NY) | Home - DHS Turf #2 [Directions] | 6:00 p.m. | ||
| Thu., 4/30 | V Boys Tennis | Norwalk | Away - Norwalk High School [Directions] | W 6-1 | ||
| Thu., 4/30 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | W 7-0 | ||
| Thu., 4/30 | V Girls Golf | Staples | Away - Longshore [Directions] | Darien 204 Staples 185 | ||
| Thu., 4/30 | V Girls Lacrosse | Greenwich | Home - DHS Stadium Field [Directions] | W 20-10 | ||
| Thu., 4/30 | JV Girls Lacrosse | Greenwich | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 4/30 | V Girls Tennis | Norwalk | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/30 | JV Girls Tennis | Greenwich | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Fri., 5/1 | V Baseball | Bassick | Away [Directions] | W 13-0 | ||
| Fri., 5/1 | FR Baseball | Trinity Catholic | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/1 | FR Boys Lacrosse | New Canaan | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Fri., 5/1 | V Boys Outdoor Track | Yellow Jacket Midnight Meet @ Newtown HS | Away | 4:30 p.m. | ||
| Fri., 5/1 | V Boys Rugby | Staples | Away [Directions] | 5:00 p.m. | TBD | |
| Fri., 5/1 | V Boys Volleyball | Harding | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Fri., 5/1 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | W 17-6 | ||
| Fri., 5/1 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Fri., 5/1 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/1 | V Softball | Bassick | Home - DHS Softball Varsity Field [Directions] | W 24-0 | ||
| Fri., 5/1 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Sat., 5/2 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | W 10-2 | ||
| Sat., 5/2 | JV Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Sat., 5/2 | FR Boys Lacrosse | Jamboree @ Don Bosco Prep, NJ | Away | TBA | ||
| Sun., 5/3 | V Co-ed Sailing | CT States @ USCGA New London | Away | TBA | ||
| Mon., 5/4 | V Baseball | Stamford | Home - DHS Baseball Varsity Field [Directions] | W 19-7 | ||
| Mon., 5/4 | JV Baseball | Stamford | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | FR Baseball | Stamford | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Boys Golf | Trumbull | Home - Wee Burn CC [Directions] | Darien 165 Trumbull 178 | ||
| Mon., 5/4 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | @ Ridgefield GC | |
| Mon., 5/4 | FR Boys Lacrosse | Staples | Away - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Mon., 5/4 | V Boys Tennis | Trinity Catholic | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/4 | JV Boys Tennis | New Canaan | Home - Cherry Lawn Park [Directions] | W 6-2 | ||
| Mon., 5/4 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 0-3 | ||
| Mon., 5/4 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Golf | Ridgefield | Home - Wee Burn CC [Directions] | Darien 211 Ridgefield | ||
| Mon., 5/4 | JV Girls Lacrosse | Greenwich Academy | Away | 3:30 p.m. | 2:30 p.m. | |
| Mon., 5/4 | FR Girls Lacrosse | Staples | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Girls Outdoor Track | Wilton, Norwalk | Away - WHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Softball | Stamford | Away - Stamford High School [Directions] | L 1-2 | ||
| Mon., 5/4 | JV Softball | Stamford | Away - Cummings Park [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | W 7-0 | ||
| Mon., 5/4 | JV Girls Tennis | New Canaan | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Tue., 5/5 | JV Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:00 p.m. | @ Griffith Harris | |
| Tue., 5/5 | V Boys Lacrosse | St. Joseph | Home - DHS Turf #2 [Directions] | W 20-4 | ||
| Tue., 5/5 | JV Boys Lacrosse | St. Joseph | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Tue., 5/5 | V Boys Outdoor Track | Norwalk, Wilton | Home - DHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/5 | V Boys Tennis | Stamford | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/5 | V Co-ed Sailing | FCSL Women's Champs @ Indian Harbor | Away | TBA | ||
| Tue., 5/5 | JV Girls Golf | Fairfield Ludlowe | Home - Woodway CC [Directions] | Cancelled | ||
| Tue., 5/5 | V Girls Tennis | Stamford | Away [Directions] | W 7-0 | ||
| Tue., 5/5 | JV Girls Tennis | Harding | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Wed., 5/6 | V Baseball | Trumbull | Home - DHS Baseball Varsity Field [Directions] | W 12-5 | ||
| Wed., 5/6 | JV Baseball | Trumbull | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/6 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/6 | JV Boys Golf | Wilton | Home - CC of Darien [Directions] | 3:00 p.m. | ||
| Wed., 5/6 | FR Boys Lacrosse | Fairfield Warde | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Wed., 5/6 | V Boys Volleyball | New Canaan | Home - DHS Main Gym [Directions] | W 3-2 | ||
| Wed., 5/6 | JV Boys Volleyball | New Canaan | Home - DHS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/6 | V Co-ed Sailing | Greenwich, Ludlowe, Stamford | Away | TBA | @ Grass Island | |
| Wed., 5/6 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | W 6-2 | ||
| Wed., 5/6 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/7 | V Boys Lacrosse | Danbury | Home - DHS Stadium Field [Directions] | W 17-4 | ||
| Thu., 5/7 | JV Boys Lacrosse | Danbury | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 5/7 | V Boys Outdoor Track | Loucks Games @ White Plains HS, NY | Away | TBA | May 7-9 | |
| Thu., 5/7 | V Boys Tennis | Westhill | Home - DHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 5/7 | JV Boys Tennis | Wilton | Home - Cherry Lawn Park [Directions] | W 5-3 | ||
| Thu., 5/7 | V Boys Volleyball | Bridgeport Central | Away - Fairchild Wheeler Magnet School [Directions] | W 3-0 | ||
| Thu., 5/7 | JV Boys Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | Cancelled | ||
| Thu., 5/7 | V Girls Golf | Fairfield Ludlowe | Home - Wee Burn CC [Directions] | Darien 202 Ludlowe 239 | ||
| Thu., 5/7 | JV Girls Golf | Greenwich | Away [Directions] | 3:15 p.m. | @ Millbrook | |
| Thu., 5/7 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | W 12-9 | ||
| Thu., 5/7 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/7 | V Girls Tennis | Westhill | Away [Directions] | W 7-0 | ||
| Thu., 5/7 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | W 10-4 | ||
| Fri., 5/8 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | FR Baseball | Greenwich | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | FR Boys Lacrosse | Greenwich | Home - Middlesex Lower Field [Directions] | 4:30 p.m. | ||
| Fri., 5/8 | V Boys Outdoor Track | Irv Black Invitational @ Willow Brook Park, New Britain, CT | Away | TBA | May 8-9 | |
| Fri., 5/8 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 5/8 | V Softball | Greenwich | Home - DHS Softball Varsity Field [Directions] | W 6-0 | ||
| Fri., 5/8 | JV Softball | Greenwich | Home - DHS Softball JV Field [Directions] | 4:30 p.m. | ||
| Sat., 5/9 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | L 8-9 | ||
| Sat., 5/9 | JV Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Sat., 5/9 | FR Boys Lacrosse | Jamboree @ Don Bosco Prep NJ | Away | TBA | ||
| Sat., 5/9 | V Boys Rugby | Stamford | Home - Royle School Field [Directions] | 10:30 a.m. | ||
| Sat., 5/9 | V Co-ed Sailing | Herresoff Qualifiers @ TBA | Away | TBA | ||
| Sat., 5/9 | V Girls Lacrosse | Farmingdale (NY) | Away | W 14-4 | 7:30 a.m. | |
| Sun., 5/10 | V Co-ed Sailing | Herreshoff Finals @ MIT | Away | TBA | ||
| Sun., 5/10 | V Co-ed Sailing | Fairfield Cup @ Pequot YC | Away | TBA | ||
| Mon., 5/11 | V Baseball | Wilton | Home - DHS Baseball Varsity Field [Directions] | W 12-1 | ||
| Mon., 5/11 | JV Baseball | Wilton | Home - DHS Baseball JV Field [Directions] | 4:30 p.m. | ||
| Mon., 5/11 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/11 | JV Boys Golf | Wilton | Away [Directions] | 3:00 p.m. | @ Rolling Hills | |
| Mon., 5/11 | FR Boys Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 5:00 p.m. | ||
| Mon., 5/11 | V Boys Tennis | Danbury | Away - Danbury High School Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/11 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | L 0-8 | ||
| Mon., 5/11 | V Boys Volleyball | Greenwich | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Mon., 5/11 | JV Boys Volleyball | Greenwich | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/11 | JV Girls Golf | New Canaan | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Mon., 5/11 | V Girls Lacrosse | Longmeadow (MA) | Away | L 9-12 | ||
| Mon., 5/11 | FR Girls Lacrosse | Ridgefield | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Mon., 5/11 | V Girls Outdoor Track | Ridgefield, Brien McMahon | Home - DHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/11 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | W 13-0 | ||
| Mon., 5/11 | JV Softball | Danbury | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 5/11 | V Girls Tennis | Danbury | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/12 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Darien 169 New Canaan 172 | ||
| Tue., 5/12 | JV Boys Golf | Greenwich | Home - CC of Darien [Directions] | 3:00 p.m. | ||
| Tue., 5/12 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | W 21-6 | ||
| Tue., 5/12 | JV Boys Lacrosse | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 5/12 | V Boys Outdoor Track | Brien McMahon, Ridgefield | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Tue., 5/12 | V Boys Tennis | Brien McMahon | Home - DHS Tennis Courts [Directions] | W 6-1 | ||
| Tue., 5/12 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | W 7-1 | ||
| Tue., 5/12 | V Girls Golf | Wilton | Home - CC of Darien [Directions] | Darien 192 Wilton 243 | ||
| Tue., 5/12 | FR Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Tue., 5/12 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | ||
| Tue., 5/12 | JV Girls Tennis | Ridgefield | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Wed., 5/13 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | W 5-2 | ||
| Wed., 5/13 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/13 | FR Baseball | Fairfield Ludlowe | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/13 | JV Boys Golf | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | 3:00 p.m. | @ Smith Richardson | |
| Wed., 5/13 | FR Boys Lacrosse | Chaminade (NY) (Scrim.) | Away | 4:30 p.m. | ||
| Wed., 5/13 | V Boys Volleyball | Trumbull | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Wed., 5/13 | JV Boys Volleyball | Trumbull | Home - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/13 | V Co-ed Sailing | GFA, Staples, Stamford | Away | TBA | @ Pequot YC | |
| Wed., 5/13 | JV Girls Golf | Fairfield Ludlowe | Home - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Wed., 5/13 | FR Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Wed., 5/13 | V Softball | Fairfield Ludlowe | Home - DHS Softball Varsity Field [Directions] | W 6-1 | ||
| Wed., 5/13 | JV Softball | Fairfield Ludlowe | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Thu., 5/14 | V Boys Golf | Westhill | Away - E. Gaynor Brennan [Directions] | Darien 159 Westhill 174 | ||
| Thu., 5/14 | V Boys Lacrosse | St. Anthonys (NY) | Away | L 7-10 | ||
| Thu., 5/14 | JV Boys Lacrosse | St. Anthonys (NY) | Away | 4:15 p.m. | 2:30 p.m. | |
| Thu., 5/14 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | L 1-6 | ||
| Thu., 5/14 | JV Boys Tennis | New Canaan | Home - Cherry Lawn Park [Directions] | W 7-1 | ||
| Thu., 5/14 | V Boys Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | W 3-0 | ||
| Thu., 5/14 | JV Boys Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 5/14 | V Girls Golf | Fairfield Warde | Home - Millbrook CC in Greenwich, CT [Directions] | Warde 198 Darien 210 | Match moved to MILLBROOK in Greenwich | |
| Thu., 5/14 | JV Girls Golf | Staples | Away - Longshore [Directions] | 3:15 p.m. | @ Longshore | |
| Thu., 5/14 | JV Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 5:30 p.m. | ||
| Thu., 5/14 | V Girls Outdoor Track | Frosh/Soph Meet | Home - DHS Track [Directions] | 3:30 p.m. | rain date 5/15 | |
| Thu., 5/14 | JV Softball | Trumbull | Home - DHS Softball JV Field [Directions] | Cancelled | ||
| Thu., 5/14 | V Girls Tennis | New Canaan | Home - DHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/14 | JV Girls Tennis | New Canaan | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Fri., 5/15 | V Baseball | Staples | Home - DHS Baseball Varsity Field [Directions] | L 2-8 | ||
| Fri., 5/15 | JV Baseball | Staples | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Fri., 5/15 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/15 | V Boys Outdoor Track | Dream Invitation @ Danbury HS | Away | 7:00 p.m. | ||
| Fri., 5/15 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | W 14-7 | ||
| Fri., 5/15 | FR Girls Lacrosse | Trumbull | Home - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Fri., 5/15 | V Softball | Staples | Away - Wakeman Field [Directions] | W 11-0 | ||
| Fri., 5/15 | JV Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Fri., 5/15 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/16 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | L 11-12(OT) | ||
| Sat., 5/16 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 11:00 a.m. | ||
| Sat., 5/16 | V Boys Rugby | Aspetuck | Home - Royle School Field [Directions] | 2:00 p.m. | ||
| Sat., 5/16 | V Co-ed Sailing | Silver Cup @ Grass Island/Indian Harbor | Away | TBA | ||
| Sat., 5/16 | V Co-ed Sailing | Mark Trophy- Hyannis YC, MA | Away | TBA | ||
| Sun., 5/17 | V Co-ed Sailing | Gold Cup @ Grass Island/Indian Harbor | Away | TBA | ||
| Sun., 5/17 | V Co-ed Sailing | Mark Trophy- Hyannis YC, MA | Away | TBA | ||
| Mon., 5/18 | V Baseball | New Canaan | Away - Mead Park [Directions] | W 6-1 | ||
| Mon., 5/18 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/18 | FR Baseball | New Canaan | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/18 | V Boys Golf | Ridgefield | Home - Wee Burn CC [Directions] | Ridgefield 158 Darien 165 | ||
| Mon., 5/18 | FR Boys Lacrosse | Daniel Hand | Home - Middlesex Lower Field [Directions] | 4:30 p.m. | ||
| Mon., 5/18 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Darien 210 Ludlowe 225 | ||
| Mon., 5/18 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/18 | V Girls Outdoor Track | Greenwich, Staples | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/18 | V Softball | New Canaan | Home - DHS Softball Varsity Field [Directions] | W 9-0 | ||
| Mon., 5/18 | JV Softball | Newtown | Away - Newtown High School Softball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/19 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Greenwich 156 Darien 162 | ||
| Tue., 5/19 | V Boys Lacrosse | Norwalk | Home - DHS Turf #2 [Directions] | W 21-2 | ||
| Tue., 5/19 | JV Boys Lacrosse | Norwalk | Home - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Tue., 5/19 | V Boys Volleyball | Newtown | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Tue., 5/19 | JV Boys Volleyball | Newtown | Home - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 5/19 | V Girls Golf | Danbury | Home - CC of Darien [Directions] | Danbury 195 Darien 204 | ||
| Tue., 5/19 | JV Girls Golf | Danbury | Home - CC of Darien [Directions] | 3:15 p.m. | ||
| Tue., 5/19 | V Girls Lacrosse | Fairfield Warde | Home - DHS Stadium Field [Directions] | W 17-8 | ||
| Tue., 5/19 | JV Girls Lacrosse | Fairfield Warde | Home - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 5/19 | JV Softball | Trumbull (Scrim.) | Home [Directions] | Cancelled | ||
| Tue., 5/19 | FR Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | ||
| Tue., 5/19 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | V Baseball | Ridgefield | Home - DHS Baseball Varsity Field [Directions] | L 1-7 | ||
| Wed., 5/20 | JV Baseball | Ridgefield | Home - Holahan Field- Town Hall [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | JV Boys Golf | Fairfield Warde, Fairfield Ludlowe | Home - Woodway CC [Directions] | 3:00 p.m. | ||
| Wed., 5/20 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | V Boys Outdoor Track | Staples, Greenwich | Home - DHS Track [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | V Boys Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | W 3-2 | ||
| Wed., 5/20 | JV Boys Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 5:30 p.m. | ||
| Wed., 5/20 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Darien 193 Trumbull 207 | ||
| Wed., 5/20 | JV Girls Golf | Trumbull | Away [Directions] | 3:15 p.m. | @ Tashua Knolls | |
| Wed., 5/20 | V Girls Lacrosse | Westhill | Away [Directions] | W 20-0 | ||
| Wed., 5/20 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 5/20 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | W 11-0 | ||
| Wed., 5/20 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | V Girls Tennis | FCIACS vs New Canaan | Home - Weed Beach [Directions] | 4:00 p.m. | ||
| Thu., 5/21 | V Boys Golf | CHAPPA @ Longshore | Away | TBA | ||
| Thu., 5/21 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | @ Ridgefield GC | |
| Thu., 5/21 | FR Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Thu., 5/21 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Darien 220 NC 214 | ||
| Thu., 5/21 | JV Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | ||
| Thu., 5/21 | FR Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Fri., 5/22 | V Baseball | Norwalk | Away - City Hall Field [Directions] | W 12-9(11) | ||
| Fri., 5/22 | JV Baseball | Norwalk | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/22 | FR Baseball | Norwalk | Home - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Fri., 5/22 | V Boys Lacrosse | FCIAC Quarter-Finals vs Staples | Home - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Fri., 5/22 | V Boys Rugby | Ridgefield | Away [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 5/22 | V Girls Lacrosse | FCIAC Quarter-Finals vs Fairfield Warde | Home - DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Fri., 5/22 | V Softball | Norwalk | Home - DHS Softball Varsity Field [Directions] | W 5-3 | ||
| Fri., 5/22 | JV Softball | Norwalk | Home - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Fri., 5/22 | V Girls Tennis | FCIACS @ Staples | Away | 4:00 p.m. | ||
| Sat., 5/23 | V Softball | FCIACS vs Trumbull | Home - DHS Softball Varsity Field [Directions] | 1:30 p.m. | ||
| Mon., 5/25 | V Boys Volleyball | Xavier | Home - DHS Main Gym [Directions] | W 3-0 | ||
| Mon., 5/25 | JV Boys Volleyball | Xavier | Home - DHS Main Gym [Directions] | 12:00 p.m. | ||
| Tue., 5/26 | V Baseball | FCIACS vs Stamford | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 5/26 | V Boys Golf | Holahan @ Woodway | Away | 12:30 p.m. | 11:05 a.m. | |
| Tue., 5/26 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | 2:30 p.m. | @ CC of New Canaan |
| Tue., 5/26 | V Boys Lacrosse | FCIACS vs New Canaan @ Brien McMahon | Away | 5:00 p.m. | 3:30 p.m. | |
| Tue., 5/26 | V Boys Outdoor Track | FCIACS @ Danbury HS | Away | 2:00 p.m. | 12:00 p.m. | |
| Tue., 5/26 | V Boys Rugby | Fairfield Prep | Away [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 5/26 | V Girls Lacrosse | FCIACS vs Wilton @ New Canaan HS | Away | 7:00 p.m. | 6:00 p.m. | |
| Tue., 5/26 | V Girls Outdoor Track | FCIACS @ Danbury HS | Away | 2:00 p.m. | 12:00 p.m. | |
| Tue., 5/26 | V Softball | FCIAC Semi-finals vs Stamford @ Sacred Heart University | Away | 3:00 p.m. | 12:45 p.m. | |
| Wed., 5/27 | V Baseball | FCIAC Semi-Finals vs Wilton @ Harbor Yard | Away | 5:00 p.m. | 3:00 p.m. | |
| Wed., 5/27 | V Boys Golf | Wilton, Staples | Home [Directions] | Darien 158 Staples 158 Wilton 161 | ||
| Wed., 5/27 | V Boys Volleyball | FCIAC Semi-Finals vs Staples @ Ludlowe | Away | 5:00 p.m. | 2:45 p.m. | |
| Wed., 5/27 | JV Girls Golf | Ekstrom JV Tournament @ South Pine Creek | Away | 3:15 p.m. | ||
| Thu., 5/28 | V Boys Golf | Norwalk, Brien McMahon | Away - Oak Hills G.C. [Directions] | Darien 158 McMahon 178 Norwalk 190 | ||
| Thu., 5/28 | V Boys Lacrosse | FCIAC Championship vs Ridgefield @ Brien McMahon | Away | 7:00 p.m. | 5:15 p.m. | |
| Thu., 5/28 | V Boys Outdoor Track | Hatter Freshman Invitational @ Danbury HS | Away | 4:00 p.m. | ||
| Thu., 5/28 | V Boys Volleyball | Tentative FCIAC Finals @ Ludlowe | Away | 7:00 p.m. | ||
| Thu., 5/28 | V Girls Golf | Danbury, Newtown | Away - Richter Park Golf Course [Directions] | Cancelled | ||
| Thu., 5/28 | V Girls Lacrosse | FCIAC Finals vs New Canaan @ Brien McMahon | Away | 4:00 p.m. | 2:30 p.m. | |
| Thu., 5/28 | V Girls Outdoor Track | Wilton | Away [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 5/29 | V Baseball | FCIAC Finals @ Harbor Yard | Away | Cancelled | ||
| Mon., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 2:30 p.m. | ||
| Mon., 6/1 | V Girls Golf | Guimares Tournament | Away | TBA | ||
| Mon., 6/1 | V Girls Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 2:30 p.m. | ||
| Mon., 6/1 | V Softball | Class LL First Round | Home - DHS Softball Varsity Field [Directions] | Cancelled | ||
| Mon., 6/1 | V Girls Tennis | CIACS vs South Windsor | Home - Chelsea Piers/Stamford [Directions] | 2:00 p.m. | ||
| Tue., 6/2 | V Boys Tennis | CIACS @ Yale University | Away | 12:00 p.m. | 10:30 a.m. | |
| Tue., 6/2 | V Boys Volleyball | Class L First Round | Home - DHS Main Gym [Directions] | Cancelled | ||
| Tue., 6/2 | V Girls Golf | Danbury | Home - CC of Darien [Directions] | Darien 200 Danbury 190 | ||
| Tue., 6/2 | V Girls Lacrosse | CIAC - Round 1 vs S. Windsor | Home - DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Wed., 6/3 | V Baseball | CIAC vs Newington HS | Home - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Wed., 6/3 | V Baseball | Tentative Class LL Second Round | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 6/3 | V Boys Golf | FCIAC Championship @ Fairchild Wheeler | Away | 12:00 p.m. | RAIN DATE JUNE 4 | |
| Wed., 6/3 | V Boys Lacrosse | CIAC - Round 1 vs Amity | Home - DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Wed., 6/3 | V Boys Tennis | CIACS @ Yale University | Away | 12:30 p.m. | 10:45 a.m. | |
| Wed., 6/3 | V Girls Golf | FCIAC Tourney @ Fairchild Wheeler | Away | 9:00 a.m. | RAIN DATE JUNE 4 | |
| Wed., 6/3 | V Girls Tennis | Class LL Quarter-Final @ Southington v Southington v New Canaan winner | Away [Directions] | 3:00 p.m. | ||
| Thu., 6/4 | V Baseball | Greenwich | Home - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Thu., 6/4 | V Boys Tennis | CIACS @ Conard HS | Away | 3:00 p.m. | ||
| Thu., 6/4 | V Boys Volleyball | Southington | Home - DHS Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 6/4 | V Girls Lacrosse | Class L Quarter Finals vs Staples | Home - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 6/4 | V Softball | Norwalk | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 6/4 | V Softball | Tournament Game - Opponent Not Known | Home - DHS Softball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 6/5 | V Baseball | Tentative Class LL Quarter Final | Home - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 6/6 | V Boys Lacrosse | New Milford | Home - DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Mon., 6/8 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Mon., 6/8 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Mon., 6/8 | V Girls Tennis | CIACS @ Yale | Away | 12:00 p.m. | ||
| Tue., 6/9 | V Baseball | Tentative Class L Semi-Final | Away | Cancelled | ||
| Tue., 6/9 | V Boys Volleyball | Shelton | Away [Directions] | 6:00 p.m. | 3:30 p.m. | |
| Wed., 6/10 | V Boys Lacrosse | Class L Semi-Final vs Glastonbury @ Cheshire | Away | 7:15 p.m. | 3:45 p.m. | |
| Wed., 6/10 | V Girls Lacrosse | Class L Semi-Finals vs Conard @ Southington HS | Away | 5:00 p.m. | 1:30 p.m. | |
| Wed., 6/10 | V Softball | Class LL Semi-Final vs Cheshire @ DeLuca Field- Stratford | Away | 7:00 p.m. | 3:30 p.m. | |
| Fri., 6/12 | V Baseball | Tentative Class LL Final or 6/13 | Away | Cancelled | ||
| Fri., 6/12 | V Boys Volleyball | Class L Final vs Ridgefield @ Shelton HS | Away | 7:00 p.m. | 3:00 p.m. | |
| Fri., 6/12 | V Softball | Class LL Final or 6/13 | Away | Cancelled | ||
| Sat., 6/13 | V Boys Lacrosse | CIAC Finals vs Ridgefield @ Brien McMahon | Away | 3:30 p.m. | 1:30 p.m. | |
| Sat., 6/13 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy (ME) | TBA | ||
| Sat., 6/13 | V Girls Lacrosse | CIAC Finals vs Wilton @ Bunnell | Away | 10:30 a.m. | 8:00 a.m. | |
| Sat., 6/13 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy (ME) | TBA | ||
| Tue., 6/16 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Tue., 6/16 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park | 11:30 a.m. | ||
| Wed., 6/17 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Thu., 6/18 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Fri., 6/19 | V Boys Outdoor Track | New Balance Outdoor Nationals @ North Carolina and Greensboro NC | Away | TBA | ||
| Mon., 5/26 | V Boys Outdoor Track | FCIAC Championship @ Danbury HS | Away | 2:00 p.m. | ||