| Staples 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1106 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Boys Alpine Skiing | Prep, Westhill, GIlbert, Westbrook, NC, SL | Away | TBA | ||
| TBA | JV Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Fairfield Warde (Scrim.) | Away - Tunxis Hill Park [Directions] | TBA | ||
| TBA | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | TBA | ||
| TBA | JV Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | TBA | ||
| TBA | JV Boys Basketball | Wilton | Home - Staples H.S. Gym [Directions] | TBA | ||
| TBA | FR Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | TBA | ||
| TBA | FR Boys Basketball | Wilton | Home - Staples H.S. Gym [Directions] | TBA | ||
| TBA | JV Boys Golf | Darien | Away - CC of Darien [Directions] | 3:15 p.m. | ED 1:50 CC of Darien | |
| TBA | JV Boys Ice Hockey | East Catholic | Away - Champions Skating Center/Cromwell [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | TBA | ||
| TBA | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | Cancelled | Cancelled | shuttle with varsity |
| TBA | V Boys Squash | Rye | Away | 8:00 p.m. | Chelsea Piers | |
| TBA | V Wrestling | Brien McMahon, Shelton | Home - Staples H.S. Gym [Directions] | 9:00 a.m. | ||
| TBA | V Competitive Cheerleading | Class LL States Championship | Away | TBA | Floyd Little Athletic Complex | |
| TBA | V Girls Alpine Skiing | Westhill, Gilbert, Westbrook, NC, SL | Away | TBA | ||
| TBA | JV Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | TBA | ride with varsity | |
| TBA | V Girls Gymnastics | Ro Carlucci Invitational | Away | TBA | ||
| TBA | V Girls Indoor Track | SCC Invitational | Away | Cancelled | Cancelled | Floyd Little Athletic Complex |
| TBA | FR Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | TBA | ||
| TBA | JV Girls Soccer | Wilton | Away - Allen's Field [Directions] | TBA | ||
| TBA | JV Softball | Fairfield Warde | Home - Staples HS - Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Greenwich | Home - Staples HS - Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | TBA | ride with varsity | |
| TBA | JV Girls Tennis | Weston | Away - Weston HS Tennis courts [Directions] | TBA | ride with varsity | |
| TBA | V Girls Water Polo | Hotchkiss | Away | 1:30 p.m. | ||
| Mon., 8/31 | V Boys Soccer | Fairfield Prep (Scrim.) | Away - Rafferty Stadium, Fairfield University [Directions] | 4:00 p.m. | ||
| Wed., 9/2 | JV Boys Soccer | New Canaan (Scrim.) | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 9/2 | V Field Hockey | Darien (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 3:45 p.m. | ||
| Wed., 9/2 | JV Field Hockey | Darien (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Thu., 9/3 | V Football | Fairfield Prep (Scrim.) | Away - Rafferty Stadium, Fairfield University [Directions] | 4:00 p.m. | 2 buses | |
| Thu., 9/3 | FR Football | Fairfield Prep (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Thu., 9/3 | V Girls Soccer | Blue vs. White scrimmage | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Thu., 9/3 | V Girls Volleyball | Jamboree | Home - Staples Field House [Directions] | 3:30 p.m. | ||
| Fri., 9/4 | V Boys Soccer | Choate Rosemary Hall (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Sat., 9/5 | V Boys Soccer | Wethersfield Jamboree | Away | 10:00 a.m. | ||
| Sat., 9/5 | V Girls Soccer | Conard Multi-team Scrimmage | Away | 8:00 a.m. | ||
| Mon., 9/7 | V Boys Soccer | Martin Luther King | Home - Loeffler Field - Staples HS [Directions] | 12:30 p.m. | ||
| Tue., 9/8 | JV Boys Soccer | Wilton (Scrim.) | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Wed., 9/9 | V Field Hockey | Convent of Sacred Heart (Scrim.) | Away | 4:15 p.m. | ||
| Wed., 9/9 | JV Field Hockey | Convent of Sacred Heart (Scrim.) | Away | 4:15 p.m. | ride with varsity | |
| Wed., 9/9 | FR Field Hockey | Darien (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 3:45 p.m. | ||
| Wed., 9/9 | JV Girls Volleyball | Trumbull (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Thu., 9/10 | V Field Hockey | Bethel (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 3:30 p.m. | ||
| Thu., 9/10 | JV Field Hockey | Bethel (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Thu., 9/10 | V Girls Soccer | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 9/10 | JV Girls Soccer | Pomperaug (Scrim.) | Away - PHS Soccer Field [Directions] | 5:00 p.m. | ride with varsity | |
| Fri., 9/11 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | 3:45 p.m. | L 0-1 | ED 2:00 |
| Fri., 9/11 | JV Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/11 | FR Boys Soccer | Trumbull | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 8-1 | |
| Fri., 9/11 | FR Girls Soccer | Trumbull | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/11 | V Girls Swimming and Diving | Danbury | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/11 | V Girls Volleyball | Ledyard | Away - Standish Gymnasium [Directions] | 6:00 p.m. | W 3-0 | ED 1:30 |
| Fri., 9/11 | JV Girls Volleyball | Ledyard | Away - Standish Gymnasium [Directions] | 4:30 p.m. | Ride with varsity | |
| Sat., 9/12 | V Boys Cross Country | Blue vs. White time trial | Home - Staples Stadium [Directions] | 9:00 a.m. | parent meeting | |
| Sat., 9/12 | V Boys Water Polo | Chelsea Piers | Away | 10:00 a.m. | JV to follow | |
| Sat., 9/12 | V Girls Cross Country | Blue vs. White time trial | Home - Staples Stadium [Directions] | 9:00 a.m. | parent meeting | |
| Sat., 9/12 | V Field Hockey | Stamford | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 4-0 | |
| Sat., 9/12 | JV Field Hockey | Stamford | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Sat., 9/12 | V Girls Soccer | Trumbull | Home - Loeffler Field - Staples HS [Directions] | 2:30 p.m. | L 2-3 | |
| Sat., 9/12 | JV Girls Soccer | Trumbull | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Tue., 9/15 | V Boys Cross Country | Danbury, Wilton, Westhill | Away - Tarrywile Park [Directions] | 4:00 p.m. | ED 1:15, 2 buses | |
| Tue., 9/15 | V Girls Cross Country | Danbury, Wilton, Westhill | Away - Tarrywile Park [Directions] | 4:00 p.m. | ED 1:15 | |
| Tue., 9/15 | V Field Hockey | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 9/15 | JV Field Hockey | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 9/15 | FR Field Hockey | Trumbull | Away - Indian Ledge Turf [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | FR Girls Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | V Girls Volleyball | Joel Barlow | Away - Lower Gym [Directions] | 5:00 p.m. | W 3-2 | |
| Tue., 9/15 | JV Girls Volleyball | Joel Barlow | Away - Lower Gym [Directions] | 3:30 p.m. | ride with varsity | |
| Wed., 9/16 | V Boys Water Polo | Suffield Academy | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 9/16 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 9/16 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 9/16 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | ||
| Thu., 9/17 | FR Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:30 p.m. | ||
| Thu., 9/17 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | W 3-1 | |
| Thu., 9/17 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | L 4-2 | |
| Thu., 9/17 | FR Boys Soccer | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/17 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Thu., 9/17 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 3:45 p.m. | ride with varsity | |
| Thu., 9/17 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/18 | V Football | Danbury | Home - Staples Stadium [Directions] | 7:00 p.m. | W 21-14 | |
| Fri., 9/18 | V Girls Soccer | Ridgefield | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 9/18 | JV Girls Soccer | Ridgefield | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/18 | FR Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Sat., 9/19 | V Boys Cross Country | Stratton Brook Invitational | Away | 9:00 a.m. | ||
| Sat., 9/19 | JV Football | Danbury | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/19 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 6:00 p.m. | W 1-0 | |
| Sat., 9/19 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | shuttle with varsity |
| Sat., 9/19 | V Girls Cross Country | Wilton Invitational | Away | 9:00 a.m. | ||
| Sat., 9/19 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 7-0 | |
| Sat., 9/19 | JV Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ride with varsity | |
| Sat., 9/19 | V Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 12:30 p.m. | W 3-2 | |
| Sat., 9/19 | JV Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 11:00 a.m. | ride with varsity | |
| Mon., 9/21 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 9/21 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 9/21 | FR Field Hockey | Westhill | Home - Ginny Parker Field - Staples [Directions] | Cancelled | Cancelled | |
| Mon., 9/21 | V Girls Soccer | Bridgeport Central | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 9/21 | V Girls Swimming and Diving | Wilton | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Mon., 9/21 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 9/21 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | ride with varsity | |
| Mon., 9/21 | FR Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/22 | V Boys Cross Country | Trumbull, Greenwich, Bridgeport Central | Away - XC Course [Directions] | 3:00 p.m. | ED 12:30, 2 buses | |
| Tue., 9/22 | V Boys Soccer | Greenwich | Home - Loeffler Field - Staples HS [Directions] | 3:00 p.m. | T 1-1 | |
| Tue., 9/22 | JV Boys Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | 3:00 p.m. | L 3-0 | |
| Tue., 9/22 | V Girls Cross Country | Trumbull, Greenwich, Bridgeport Central | Away - XC Course [Directions] | 3:00 p.m. | ED 12:30 | |
| Thu., 9/24 | FR Football | Wilton | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/24 | V Boys Water Polo | Hopkins School | Away | 4:15 p.m. | ED 1:45, JV to follow | |
| Thu., 9/24 | V Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | T 3-3 | |
| Thu., 9/24 | JV Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Thu., 9/24 | FR Field Hockey | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 9/24 | FR Girls Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/24 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ED 1:45 | |
| Fri., 9/25 | V Football | Wilton | Away - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 37-0 | 2 buses |
| Fri., 9/25 | V Boys Soccer | St. Joseph | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/25 | JV Boys Soccer | St. Joseph | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 9/25 | V Competitive Cheerleading | Wilton | Away [Directions] | 7:00 p.m. | ||
| Fri., 9/25 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 9/25 | JV Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 9/25 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 5:30 p.m. | ||
| Fri., 9/25 | V Girls Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/25 | JV Girls Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/25 | FR Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Sat., 9/26 | V Boys Cross Country | Bowdoin Park Classic | Away | 10:00 a.m. | Bowdian Park, Wappinger Falls, NY | |
| Sat., 9/26 | JV Football | Norwalk | Home - Staples Stadium [Directions] | 11:00 a.m. | ||
| Sat., 9/26 | FR Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 10:00 a.m. | L 2-0 | |
| Sat., 9/26 | V Girls Cross Country | Bowdoin Park Classic | Away | 10:00 a.m. | ||
| Sat., 9/26 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 1:00 p.m. | L 0-8 | |
| Sat., 9/26 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 1:00 p.m. | ride with varsity | |
| Sat., 9/26 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Mon., 9/28 | V Boys Soccer | Westhill | Away - Westhill Football Field [Directions] | 4:00 p.m. | W 4-0 | ED 2:00 |
| Mon., 9/28 | JV Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 5:15 p.m. | W 1-0 | |
| Mon., 9/28 | FR Boys Soccer | Westhill | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 9/28 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | L 0-1 | |
| Mon., 9/28 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | ride with varsity | |
| Mon., 9/28 | FR Field Hockey | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | V Girls Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/28 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 9/28 | FR Girls Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Boys Cross Country | New Canaan, Trinity Catholic, Fairfield Warde, Fairfield Ludlowe | Away - Waveny Park [Directions] | 4:00 p.m. | ED 1:30, 2 buses | |
| Tue., 9/29 | V Girls Cross Country | New Canaan, Trinity Catholic, Fairfield Warde, Fairfield Ludlowe | Away - Waveny Park [Directions] | 4:00 p.m. | ED 1:30 | |
| Tue., 9/29 | V Girls Soccer | Westhill | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 9/29 | JV Girls Soccer | Westhill | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/30 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 9/30 | V Boys Water Polo | Brunswick School | Away | 4:00 p.m. | ||
| Wed., 9/30 | V Girls Swimming and Diving | Trumbull | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 9/30 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/30 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 10/1 | FR Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | ||
| Thu., 10/1 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | L 0-2 | |
| Thu., 10/1 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 5:30 p.m. | shuttle with varsity | |
| Thu., 10/1 | FR Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Girls Soccer | Brien McMahon | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/1 | JV Girls Soccer | Brien McMahon | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Fri., 10/2 | V Football | Fairfield Warde | Home - Staples Stadium [Directions] | 7:00 p.m. | W 35-15 | Homecoming |
| Fri., 10/2 | V Boys Soccer | Fairfield Ludlowe | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/2 | JV Boys Water Polo | Greenwich HS Tournament | Away | 4:00 p.m. | ||
| Fri., 10/2 | V Girls Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 10/2 | JV Girls Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/2 | FR Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/3 | JV Boys Water Polo | Greenwich Tournament | Away | 10:00 a.m. | ||
| Sun., 10/4 | JV Boys Water Polo | Greenwich HS Tournament | Away | 10:00 a.m. | ||
| Mon., 10/5 | JV Football | Fairfield Warde | Home - Staples Stadium [Directions] | 6:30 p.m. | ||
| Mon., 10/5 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | L 2-4 | |
| Mon., 10/5 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 10/5 | FR Girls Soccer | Fairfield Ludlowe | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Mon., 10/5 | V Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/5 | JV Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/5 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Boys Cross Country | Norwalk, St. Joseph, Stamford | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Boys Soccer | Norwalk | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/6 | JV Boys Soccer | Norwalk | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 10/6 | FR Boys Soccer | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:30 p.m. | W 4-2 | |
| Tue., 10/6 | V Girls Cross Country | Norwalk, St. Joseph, Stamford | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Swimming and Diving | East Lyme | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | W 6-0 | |
| Wed., 10/7 | JV Girls Soccer | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | shuttle with varsity | |
| Wed., 10/7 | FR Girls Soccer | Masuk | Away - Masuk Middle Field [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/7 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 10/7 | FR Girls Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | FR Football | Brien McMahon | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/8 | V Boys Soccer | Darien | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 10/8 | JV Boys Soccer | Darien | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-0 | |
| Thu., 10/8 | FR Boys Soccer | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 10/8 | V Field Hockey | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 10/8 | JV Field Hockey | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Fri., 10/9 | V Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 28-0 | 2 buses |
| Fri., 10/9 | V Boys Water Polo | Hopkins School | Away | 4:15 p.m. | JV to follow | |
| Fri., 10/9 | V Competitive Cheerleading | Brien McMahon | Away [Directions] | 7:00 p.m. | ||
| Fri., 10/9 | V Field Hockey | Darien | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/9 | JV Field Hockey | Darien | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Fri., 10/9 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 10/9 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/9 | FR Girls Soccer | Darien | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Fri., 10/9 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 10/9 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 10/9 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Sat., 10/10 | V Boys Cross Country | Wickham Park Invitational | Away | 9:40 a.m. | 2 buses | |
| Sat., 10/10 | JV Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | V Boys Water Polo | Hotchkiss and Suffield Academy | Away | 1:30 p.m. | @ Suffield | |
| Sat., 10/10 | V Girls Cross Country | Wickham Park Invitational | Away | Cancelled | Cancelled | |
| Sat., 10/10 | V Girls Swimming and Diving | St. Joseph | Away - Orange Center Rec., Orange, CT [Directions] | 4:00 p.m. | ||
| Sat., 10/10 | JV Girls Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 9:30 a.m. | Hillcrest Middle School | |
| Sat., 10/10 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Mon., 10/12 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | T 0-0 | |
| Mon., 10/12 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | W 5-1 | |
| Mon., 10/12 | FR Boys Soccer | New Canaan | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/13 | V Boys Cross Country | Ridgefield, Darien, Brien McMahon | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | Ridgefield, Darien, Brien McMahon | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | W 2-0 | |
| Tue., 10/13 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Tue., 10/13 | V Girls Soccer | New Canaan | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/13 | JV Girls Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | FR Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 10/13 | JV Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/13 | FR Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/14 | V Boys Water Polo | Choate Rosemary Hall | Away | 4:00 p.m. | ED 1:45, JV to follow | |
| Wed., 10/14 | V Girls Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 4:00 p.m. | ED 2:00 | |
| Wed., 10/14 | V Girls Volleyball | Norwalk | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/14 | JV Girls Volleyball | Norwalk | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/15 | FR Football | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | W 2-1 | ED 1:45 |
| Thu., 10/15 | JV Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:30 p.m. | ride with varsity | |
| Thu., 10/15 | FR Field Hockey | Danbury | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | FR Girls Soccer | Ridgefield | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | JV Girls Swimming and Diving | Greenwich, Trumbull | Away - GHS Pool [Directions] | 5:30 p.m. | ||
| Fri., 10/16 | V Football | Stamford | Home - Staples Stadium [Directions] | 7:00 p.m. | W 35-0 | |
| Fri., 10/16 | FR Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:15 p.m. | W 3-0 | |
| Fri., 10/16 | V Boys Water Polo | Greenwich HS Tournament | Away | 4:30 p.m. | ||
| Fri., 10/16 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | FR Girls Soccer | Wilton | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Fri., 10/16 | V Girls Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 10/16 | JV Girls Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/16 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/17 | JV Football | Stamford | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/17 | V Boys Soccer | Wilton | Home - Loeffler Field - Staples HS [Directions] | 12:00 p.m. | L 2-1 | |
| Sat., 10/17 | JV Boys Soccer | Wilton | Home - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | W 3-2 | |
| Sat., 10/17 | V Boys Water Polo | Greenwich High School Tournament | Away | 9:00 a.m. | ||
| Sat., 10/17 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 11:00 a.m. | L 0-1 | |
| Mon., 10/19 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | L 2-1 | |
| Mon., 10/19 | JV Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | W 2-1 | shuttle with varsity |
| Mon., 10/19 | FR Boys Soccer | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 9-3 | |
| Mon., 10/19 | V Field Hockey | Brien McMahon | Home - Staples Stadium [Directions] | 6:30 p.m. | W 7-0 | |
| Mon., 10/19 | JV Field Hockey | Brien McMahon | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | ||
| Mon., 10/19 | JV Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 3:30 p.m. | ED 1:45 Barlow Mountain Elem School | |
| Mon., 10/19 | V Girls Volleyball | New Canaan | Away [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 10/19 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 10/19 | FR Girls Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 3:45 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Fairfield Warde | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 1-2 | |
| Tue., 10/20 | JV Girls Soccer | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | V Boys Cross Country | FCIAC Championships @ Waveny Park | Away | 2:15 p.m. | ED 11:15, 2 buses | |
| Wed., 10/21 | V Boys Soccer | Trinity Catholic | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 8-0 | |
| Wed., 10/21 | V Boys Water Polo | Brunswick School | Home - Staples HS Pool [Directions] | 4:00 p.m. | JV to follow | |
| Wed., 10/21 | V Girls Cross Country | FCIAC Championship @ Waveny Park | Away | 2:15 p.m. | ED 1:15 | |
| Wed., 10/21 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ED 1:00 | |
| Wed., 10/21 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | FR Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/22 | V Girls Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | 4:00 p.m. | W 7-0 | |
| Fri., 10/23 | V Football | Ridgefield | Home - Staples Stadium [Directions] | 7:00 p.m. | L 27-31 | |
| Fri., 10/23 | V Boys Soccer | Stamford | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 10/23 | JV Boys Soccer | Stamford | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 2-1 | |
| Fri., 10/23 | FR Boys Soccer | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 10/23 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/23 | V Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/23 | JV Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/23 | FR Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Sat., 10/24 | JV Football | Ridgefield | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | V Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 4:00 p.m. | L 3-4 | |
| Sat., 10/24 | JV Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:30 p.m. | ||
| Sat., 10/24 | JV Girls Swimming and Diving | New Canaan, Darien | Home - Staples HS Pool [Directions] | 9:00 a.m. | ||
| Sun., 10/25 | V Field Hockey | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 11:00 a.m. | W 5-1 | |
| Mon., 10/26 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | L 3-1 | |
| Mon., 10/26 | JV Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 6:00 p.m. | W 2-1 | |
| Mon., 10/26 | FR Boys Soccer | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/26 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 6:00 p.m. | W 2-0 | |
| Mon., 10/26 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 10/26 | FR Field Hockey | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 10/26 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 10/26 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:30 p.m. | ride with varsity | |
| Mon., 10/26 | FR Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Boys Cross Country | Bethel JV Invitational | Away | Cancelled | Cancelled | ED 1:30 |
| Tue., 10/27 | JV Boys Soccer | Fairfield Ludlowe | Home - Wakeman Field B (turf) [Directions] | 4:15 p.m. | T 1-1 | |
| Tue., 10/27 | V Girls Cross Country | Bethel JV Invitational | Away | Cancelled | Cancelled | ED 1:30 |
| Tue., 10/27 | JV Field Hockey | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | Cancelled | Cancelled | |
| Tue., 10/27 | V Girls Soccer | Danbury | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/27 | JV Girls Soccer | Danbury | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | FR Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 10/28 | V Girls Volleyball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 10/28 | JV Girls Volleyball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/29 | V Boys Cross Country | Danbury Freshmen Invitational | Away | 4:00 p.m. | ED 1:15 | |
| Thu., 10/29 | V Boys Soccer | Darien | Away [Directions] | 3:30 p.m. | L 2-0 | ED 1:30 |
| Thu., 10/29 | V Girls Cross Country | Danbury Freshmen Invitational | Away | 4:00 p.m. | ED 1:15 | |
| Thu., 10/29 | JV Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 10/29 | FR Girls Volleyball | Westhill | Away [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | Miscellaneous Events | Westport Field Hockey 8th grade | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Fri., 10/30 | FR Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/30 | V Boys Water Polo | Chelsea Piers | Away | TBA | ||
| Fri., 10/30 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 3:00 p.m. | L 1-0 | ED 1:15 |
| Fri., 10/30 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | W 3-2 | ED 1:45 |
| Fri., 10/30 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ride with varsity | |
| Fri., 10/30 | FR Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/31 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:55 a.m. | ||
| Sat., 10/31 | V Boys Water Polo | CT State Challenge @ Connecticut College | Away | 5:00 p.m. | ||
| Sat., 10/31 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:20 a.m. | ||
| Sat., 10/31 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | JV Girls Swimming and Diving | JV FCIAC Championships @ Greenwich HS | Away | 12:00 p.m. | ||
| Tue., 11/3 | V Girls Swimming and Diving | FCIAC Swimming Trials | Away | 4:00 p.m. | ||
| Tue., 11/3 | V Girls Volleyball | Darien | Away [Directions] | 4:00 p.m. | ||
| Wed., 11/4 | V Field Hockey | Greenwich Academy (Scrim.) | Away | 3:15 p.m. | ||
| Wed., 11/4 | V Field Hockey | Greenwich Academy (Scrim.) | Away | 3:15 p.m. | ||
| Wed., 11/4 | V Girls Swimming and Diving | FCIAC Diving Finals @ Westhill | Away | 4:30 p.m. | ||
| Thu., 11/5 | FR Football | St. Joseph | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/5 | V Girls Swimming and Diving | FCIAC Swimming Finals @ Greenwich HS | Away | 4:30 p.m. | ED 1:30 | |
| Fri., 11/6 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ED 10:30 | |
| Fri., 11/6 | V Boys Soccer | Norwalk (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Fri., 11/6 | V Boys Water Polo | Loomis Chaffee School | Home - Staples HS Pool [Directions] | 4:30 p.m. | JV to follow | |
| Fri., 11/6 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ED 10:30 | |
| Sat., 11/7 | V Football | St. Joseph | Away - St. Joseph HS [Directions] | 2:00 p.m. | W 28-20 | 2 buses |
| Sat., 11/7 | V Boys Water Polo | Hotchkiss | Home - Staples HS Pool [Directions] | 4:00 p.m. | JV to follow | |
| Sat., 11/7 | V Competitive Cheerleading | St. Joseph | Away [Directions] | 2:00 p.m. | ||
| Mon., 11/9 | JV Football | St. Joseph | Away - St. Joseph HS [Directions] | 3:00 p.m. | ED 1:30 | |
| Mon., 11/9 | V Girls Soccer | Class LL vs. Darien | Away | 2:00 p.m. | ED 12:15 | |
| Mon., 11/9 | V Girls Volleyball | Class LL First Round vs. Shelton | Away | 6:00 p.m. | ||
| Tue., 11/10 | V Boys Soccer | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 4:00 p.m. | L 2-1 | ED 12:45 |
| Tue., 11/10 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | Cancelled | Cancelled | |
| Wed., 11/11 | V Field Hockey | Class L First Round vs. So. Windsor | Away | 2:00 p.m. | ED 10:45 | |
| Wed., 11/11 | V Girls Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Bulkeley HS [Directions] | 4:30 p.m. | ||
| Thu., 11/12 | FR Football | Darien | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/12 | V Girls Volleyball | Class LL Second Round vs. Darien | Away | 5:00 p.m. | ||
| Fri., 11/13 | V Field Hockey | CIAC Quarterfinal vs. Conard | Away | 5:00 p.m. | ||
| Sat., 11/14 | V Boys Cross Country | New England Championship | Away - Thetford Academy (VT) [Directions] | TBA | ||
| Sat., 11/14 | V Football | Darien | Away - DHS Stadium Field [Directions] | 1:00 p.m. | L 0-27 | 3 buses |
| Sat., 11/14 | V Competitive Cheerleading | Darien | Away [Directions] | 1:30 p.m. | ||
| Sat., 11/14 | V Girls Cross Country | New England Championship | Away - Thetford Academy (VT) [Directions] | TBA | ||
| Sat., 11/14 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 11:30 a.m. | ||
| Mon., 11/16 | JV Football | Greenwich | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Tue., 11/17 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Thu., 11/19 | FR Football | Greenwich | Away - Cardinal Stadium [Directions] | 3:15 p.m. | ED 1:30 | |
| Thu., 11/19 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/21 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Thu., 11/26 | V Football | Greenwich | Home - Staples Stadium [Directions] | 10:00 a.m. | W 28-26 | |
| Mon., 11/30 | V Boys Squash | New Canaan | Away [Directions] | 8:00 p.m. | Chelsea Piers | |
| Tue., 12/1 | V Football | Darien | Away - Brien McMahon HS [Directions] | 6:30 p.m. | ||
| Sat., 12/5 | V Girls Ice Hockey | FCIAC Jamboree | Away - Shelton Ice Rink | 4:00 p.m. | ||
| Mon., 12/7 | V Girls Squash | Rye 3 | Away | 3:30 p.m. | ED, 1:45, LifeTime | |
| Tue., 12/8 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away [Directions] | 6:00 p.m. | ||
| Wed., 12/9 | V Boys Ice Hockey | Lyman Hall (Scrim.) | Home - Milford Ice Pavilion [Directions] | 7:00 p.m. | W 4-2 | |
| Fri., 12/11 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 5:00 p.m. | ||
| Fri., 12/11 | V Boys Indoor Track | Blue vs. White Event Trials | Home - Staples Field House [Directions] | 2:45 p.m. | ||
| Fri., 12/11 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown HS Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 12/12 | V Boys Ice Hockey | Taconic (MA) (Scrim.) | Away | 7:00 p.m. | W 10-1 | |
| Sat., 12/12 | JV Boys Ice Hockey | Wahconah Regional (MA) (Scrim.) | Away | 12:00 p.m. | ||
| Sat., 12/12 | V Boys Indoor Track | Blue vs. White Event Trials | Home - Staples Field House [Directions] | 9:00 a.m. | ||
| Sat., 12/12 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Terry Conners Ice Rink [Directions] | 2:10 p.m. | W 4-3 | |
| Sun., 12/13 | V Boys Ice Hockey | Wahconah Regional (MA) (Scrim.) | Away | 12:00 p.m. | W 4-2 | |
| Sun., 12/13 | V Boys Squash | Fairwest Jamboree 1 | Away | 4:00 p.m. | Chelsea Piers | |
| Sun., 12/13 | V Girls Squash | Fairwest Jamboree 1 | Away | 4:00 p.m. | Chelsea Piers | |
| Mon., 12/14 | V Boys Basketball | Foran (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | ||
| Mon., 12/14 | JV Boys Basketball | Foran (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | ||
| Mon., 12/14 | V Girls Basketball | Norwalk (Scrim.) | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/14 | JV Girls Basketball | Norwalk (Scrim.) | Away [Directions] | 4:00 p.m. | ride with varsity | |
| Tue., 12/15 | V Girls Basketball | Bassick | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 65-5 | |
| Tue., 12/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 8:50 p.m. | W 5-1 | |
| Wed., 12/16 | V Boys Basketball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/16 | V Boys Ice Hockey | Norwalk (Scrim.) | Home - Longshore [Directions] | 6:00 p.m. | W 4-2 | |
| Wed., 12/16 | V Wrestling | Norwalk | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/16 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | 5:30 p.m. | W 2-0 | |
| Thu., 12/17 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 38-25 | |
| Thu., 12/17 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 12/17 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/18 | JV Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavilion [Directions] | 3:00 p.m. | ||
| Fri., 12/18 | V Girls Basketball | Bethel | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 30-40 | |
| Fri., 12/18 | JV Girls Basketball | Bethel | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/18 | V Girls Squash | Darien | Away [Directions] | 4:00 p.m. | Chelsea Piers | |
| Sat., 12/19 | V Boys Indoor Track | FCIAC Qualifier #1 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/19 | V Wrestling | Fairfield Ludlowe Invitational | Away | 9:00 a.m. | ||
| Sat., 12/19 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:20 p.m. | L 0-6 | Staples bus 6:30 pm separate |
| Sat., 12/19 | V Girls Indoor Track | FCIAC Qualifier #1 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Mon., 12/21 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 12/21 | V Boys Squash | Greenwich | Away [Directions] | 8:00 p.m. | Chelsea Piers | |
| Mon., 12/21 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | 5:45 p.m. | W 61-29 | |
| Mon., 12/21 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ride with varsity | |
| Mon., 12/21 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | 7:30 p.m. | W 4-0 | |
| Tue., 12/22 | V Boys Basketball | Darien | Home - Trumbull HS [Directions] | 5:30 p.m. | W 44-43 | |
| Wed., 12/23 | V Boys Basketball | New Canaan | Home - Trumbull HS [Directions] | 5:00 p.m. | W 48-23 | |
| Wed., 12/23 | V Boys Ice Hockey | Norwich Free Academy | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 6-1 | |
| Wed., 12/23 | V Girls Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | W 36-23 | |
| Wed., 12/23 | JV Girls Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/23 | FR Girls Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/26 | JV Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | 2:00 p.m. | ||
| Sat., 12/26 | V Boys Indoor Track | Hillhouse Winter Relays | Away | 10:00 a.m. | 1 bus | |
| Mon., 12/28 | V Boys Basketball | Wilton | Away - Newtown HS [Directions] | 4:00 p.m. | L 55-56 | |
| Mon., 12/28 | V Boys Ice Hockey | Daniel Hand | Home - Milford Ice Pavilion [Directions] | 4:15 p.m. | L 3-5 | |
| Mon., 12/28 | V Girls Basketball | Manchester | Away - MAIN GYM AT MHS [Directions] | 1:30 p.m. | W 54-41 | |
| Tue., 12/29 | JV Boys Ice Hockey | Cheshire | Home - Milford Ice Pavilion [Directions] | 4:45 p.m. | ||
| Wed., 12/30 | V Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | TBA | L 39-41 | |
| Wed., 12/30 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 1:00 p.m. | L 3-4 | |
| Wed., 12/30 | JV Boys Ice Hockey | Guilford | Away - Milford Ice Pavilion [Directions] | 3:00 p.m. | ||
| Wed., 12/30 | V Wrestling | Greenwich, Darien, Fairfield Warde | Away - GHS Gymnasium [Directions] | 1:00 p.m. | ||
| Wed., 12/30 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 2:00 p.m. | 126.55 | |
| Thu., 12/31 | JV Boys Ice Hockey | JV Jamboree Championship | Away | 9:15 a.m. | ||
| Fri., 1/1 | V Boys Ice Hockey | Amity | Home - Milford Ice Pavilion [Directions] | 7:00 p.m. | W 7-0 | |
| Sat., 1/2 | JV Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 1:30 p.m. | ||
| Sat., 1/2 | V Boys Indoor Track | Wintergreen Invitational | Away | Cancelled | Cancelled | |
| Sat., 1/2 | V Wrestling | Bunnell Duals | Away | 10:00 a.m. | ||
| Sat., 1/2 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 7:00 p.m. | L 2-4 | Staples bus 5:00 pm separate bus |
| Mon., 1/4 | JV Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ED 1:45 | |
| Mon., 1/4 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | L 1-5 | |
| Tue., 1/5 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 45-58 | |
| Tue., 1/5 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Tue., 1/5 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/5 | V Wrestling | Westhill | Away - Westhill New Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/5 | V Girls Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 27-49 | |
| Tue., 1/5 | JV Girls Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/5 | FR Girls Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/6 | V Boys Alpine Skiing | Prep, Westhill, Gilbert, Westbrook, NC, SL | Away | Cancelled | Cancelled | |
| Wed., 1/6 | V Boys Ice Hockey | Norwich Free Academy | Away - Norwich Ice Rink [Directions] | 5:00 p.m. | W 6-3 | |
| Wed., 1/6 | V Boys Squash | Fairfield | Home - The Gym at Southport Athletic [Directions] | 8:00 p.m. | ||
| Wed., 1/6 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/6 | V Girls Alpine Skiing | Westhill, Gilbert, Westbrook, NC, SL | Away | Cancelled | Cancelled | |
| Wed., 1/6 | V Girls Gymnastics | Westhill, New Canaan | Away [Directions] | 5:30 p.m. | 117.65 | |
| Wed., 1/6 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 4:00 p.m. | L 0-1 | |
| Fri., 1/8 | V Boys Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 37-40 | |
| Fri., 1/8 | JV Boys Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Boys Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | JV Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - Milford Ice Pavilion [Directions] | 7:00 p.m. | ||
| Fri., 1/8 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:30 p.m. | ED 1:45 | |
| Fri., 1/8 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 32-53 | |
| Fri., 1/8 | JV Girls Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | ride with varsity | |
| Fri., 1/8 | FR Girls Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | V Girls Indoor Track | Elm City Invitational | Away | TBA | @ Hillhouse | |
| Fri., 1/8 | V Girls Squash | New Haven | Away | 5:00 p.m. | Yale University | |
| Sat., 1/9 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 7:00 p.m. | W 6-1 | |
| Sat., 1/9 | V Boys Indoor Track | FCIAC Qualifier #2 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/9 | V Wrestling | Fairfield Warde Invitational | Away | 9:30 a.m. | ||
| Sat., 1/9 | V Girls Gymnastics | Pomperaug Invitational | Away | 10:00 a.m. | 121.75 | |
| Sat., 1/9 | V Girls Indoor Track | FCIAC Qualifier #2 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/9 | V Girls Indoor Track | Elm City Invitational | Away | 8:00 a.m. | @ Hillhouse | |
| Tue., 1/12 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:45 p.m. | W 4-3(OT) | Staples separate bus 2:30 pm |
| Wed., 1/13 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 6:00 p.m. | L 64-68 | |
| Wed., 1/13 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:30 p.m. | ride with varsity | |
| Wed., 1/13 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 3:00 p.m. | ||
| Wed., 1/13 | V Wrestling | Ridgefield | Away - RHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/13 | V Girls Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | L 19-56 | |
| Wed., 1/13 | JV Girls Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/13 | FR Girls Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 3:00 p.m. | ||
| Wed., 1/13 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 3:30 p.m. | W 3-2 | |
| Thu., 1/14 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | 4:00 p.m. | 118.1 | |
| Fri., 1/15 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 7:00 p.m. | W 69-57 | |
| Fri., 1/15 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Fri., 1/15 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | JV Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | 5:50 p.m. | ||
| Fri., 1/15 | V Boys Indoor Track | Yale Classic | Away | 1:00 p.m. | Cox Cage | |
| Fri., 1/15 | V Boys Swimming and Diving | Greenwich | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Girls Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | W 43-20 | |
| Fri., 1/15 | JV Girls Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Girls Ice Hockey | Northwest Catholic | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 1/15 | V Girls Indoor Track | East Coast Invitaional | Away | Cancelled | Cancelled | Providence RI |
| Fri., 1/15 | V Girls Indoor Track | Yale Classic | Away | 1:00 p.m. | ||
| Sat., 1/16 | V Boys Ice Hockey | Trinity Catholic | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 11-0 | |
| Sat., 1/16 | V Boys Indoor Track | Yale Classic | Away | 9:00 a.m. | Cox Cage | |
| Sat., 1/16 | V Boys Indoor Track | FCIAC Qualifier #3 | Home - Staples Field House [Directions] | TBA | ||
| Sat., 1/16 | V Wrestling | Brien McMahon, Weston, Bunnell, Greenwich | Home [Directions] | 10:00 a.m. | ||
| Sat., 1/16 | V Competitive Cheerleading | Hatter Fest | Away | Cancelled | Cancelled | Danbury HS |
| Sat., 1/16 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | 1:30 p.m. | 117.6 | |
| Sat., 1/16 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | W 2-0 | |
| Sat., 1/16 | V Girls Indoor Track | East Coast Invitaional | Away | 7:00 a.m. | Providence RI | |
| Sat., 1/16 | V Girls Indoor Track | FCIAC Qualifier #3 | Home - Staples Field House [Directions] | TBA | ||
| Mon., 1/18 | JV Boys Ice Hockey | Darien | Home - Milford Ice Pavilion [Directions] | 2:30 p.m. | ||
| Tue., 1/19 | V Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 51-52 | |
| Tue., 1/19 | JV Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/19 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | L 25-71 | |
| Tue., 1/19 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ride with varsity | |
| Tue., 1/19 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/20 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 0-4 | |
| Wed., 1/20 | V Boys Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/20 | V Girls Ice Hockey | New Canaan | Home [Directions] | 5:00 p.m. | L 0-3 | Terry Conners Rink |
| Wed., 1/20 | V Girls Squash | Rye 3 | Away | 3:30 p.m. | LifeTime | |
| Thu., 1/21 | V Boys Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 57-53 | |
| Thu., 1/21 | JV Boys Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/21 | FR Boys Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/21 | V Boys Squash | Bronxville HS @ Sarah Lawrence College | Away | 5:00 p.m. | ||
| Thu., 1/21 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | L 38-41(OT) | |
| Thu., 1/21 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ride with varsity | |
| Thu., 1/21 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | V Boys Swimming and Diving | Trumbull | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Sat., 1/23 | V Boys Indoor Track | SCC Invitational | Away | Cancelled | Cancelled | Floyd Little Athletic Complex |
| Mon., 1/25 | V Boys Ice Hockey | Ridgefield | Home - Milford Ice Pavilion [Directions] | 7:00 p.m. | L 0-5 | |
| Tue., 1/26 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 45-59 | |
| Tue., 1/26 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ride with varsity | |
| Tue., 1/26 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/26 | V Boys Indoor Track | FCIAC Qualifier #4 | Home - Staples Field House [Directions] | 3:30 p.m. | ||
| Tue., 1/26 | V Girls Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | L 43-54 | |
| Tue., 1/26 | JV Girls Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/26 | FR Girls Basketball | Westhill | Home - Staples H.S. Gym [Directions] | Cancelled | Cancelled | |
| Tue., 1/26 | V Girls Indoor Track | FCIAC Qualifier #4 | Home - Staples Field House [Directions] | 3:30 p.m. | ||
| Wed., 1/27 | V Boys Alpine Skiing | Brunswick, Amity, Wilton, Glastonbury | Away | 4:00 p.m. | ||
| Wed., 1/27 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 7-0 | |
| Wed., 1/27 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ED 1:15 | |
| Wed., 1/27 | V Wrestling | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | ||
| Wed., 1/27 | V Girls Alpine Skiing | Brunswick, Amity, LH, Wilton, Glastonbury | Away | 4:00 p.m. | ||
| Wed., 1/27 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 1/28 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | 7:00 p.m. | 119.85 | |
| Thu., 1/28 | V Girls Ice Hockey | Branford | Home - Westport PAL Rink Longshore [Directions] | 7:30 p.m. | W 2-1 | |
| Fri., 1/29 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 41-56 | |
| Fri., 1/29 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ride with varsity | |
| Fri., 1/29 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Fri., 1/29 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Milford Ice Pavilion [Directions] | 8:30 p.m. | ||
| Fri., 1/29 | V Girls Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 5:45 p.m. | W 58-39 | |
| Fri., 1/29 | JV Girls Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | ||
| Sat., 1/30 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | 4:00 p.m. | W 3-2 | |
| Sat., 1/30 | V Boys Indoor Track | FCIAC Divisional Championship | Home - Staples Field House [Directions] | TBA | ||
| Sat., 1/30 | V Wrestling | Highlander Invitational @ Portland HS | Away | 9:00 a.m. | ||
| Sat., 1/30 | V Competitive Cheerleading | Quinnipiac's 2016 Cheer & Dance Challenge | Away | TBA | ||
| Sat., 1/30 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics [Directions] | 6:00 p.m. | 118.65 | |
| Sat., 1/30 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | 2:10 p.m. | W 5-2 | |
| Sat., 1/30 | V Girls Indoor Track | FCIAC Divisional Championship | Home - Staples Field House [Directions] | TBA | ||
| Sun., 1/31 | V Boys Squash | Fairwest Jamboree 2 | Away | 4:00 p.m. | Chelsea Piers | |
| Sun., 1/31 | V Girls Squash | Fairwest Jamboree 2 | Away | Cancelled | Cancelled | Chelsea Piers |
| Mon., 2/1 | V Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 48-35 | |
| Mon., 2/1 | JV Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/1 | FR Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/1 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 6:00 p.m. | W 3-0 | stop at MIP enroute |
| Mon., 2/1 | V Boys Squash | Darien | Away [Directions] | 8:00 p.m. | Chelsea Piers | |
| Mon., 2/1 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | L 34-52 | |
| Mon., 2/1 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Mon., 2/1 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/1 | Unified Sports Basketball | Basketball at Fairfield Ludlowe | Away | 3:00 p.m. | Bus must stay | |
| Tue., 2/2 | V Boys Alpine Skiing | Farifield, Cheshire, Litch, Hopkins, Greenwich | Away | 4:00 p.m. | ||
| Tue., 2/2 | JV Boys Ice Hockey | Guilford | Away [Directions] | 5:50 p.m. | ||
| Tue., 2/2 | V Girls Alpine Skiing | Fairfield, cheshire, Litch, Hopkins, Greenwich | Away | 4:00 p.m. | ||
| Tue., 2/2 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 8:30 p.m. | L 0-7 | Staples bus separate 6:45 pm |
| Wed., 2/3 | V Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 64-52 | |
| Wed., 2/3 | JV Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/3 | FR Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/3 | V Boys Ice Hockey | Greenwich | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 1-5 | |
| Wed., 2/3 | V Wrestling | Danbury | Home - Staples Field House [Directions] | 6:00 p.m. | ||
| Wed., 2/3 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | L 40-57 | |
| Wed., 2/3 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 2/4 | V Boys Indoor Track | FCIAC Championship | Away | TBA | Floyd Little Athletic Complex | |
| Thu., 2/4 | V Girls Indoor Track | FCIAC Championship | Away | TBA | Floyd Little Athletic Complex | |
| Thu., 2/4 | V Girls Squash | St. Lukes | Away | 3:45 p.m. | St Lukes School | |
| Sat., 2/6 | V Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | 3:00 p.m. | L 48-53 | |
| Sat., 2/6 | V Boys Indoor Track | FCIAC JV Invitational | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/6 | V Wrestling | Stamford | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/6 | V Competitive Cheerleading | FCIAC Championship | Away | TBA | Wilton HS | |
| Sat., 2/6 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | 7:30 p.m. | L 1-2 | |
| Tue., 2/9 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | L 55-57 | |
| Tue., 2/9 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | ride with varsity | |
| Tue., 2/9 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/9 | V Wrestling | Trumbull | Away - Auxiliary gym [Directions] | 6:00 p.m. | ||
| Tue., 2/9 | V Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 45-49 | |
| Tue., 2/9 | JV Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/9 | FR Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/9 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 4:30 p.m. | 121.65 | |
| Wed., 2/10 | V Boys Alpine Skiing | Barlow, Danbury, Southington, Guilford, CA, Weston, Hand | Away | 4:00 p.m. | ||
| Wed., 2/10 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 6:10 p.m. | L 2-5 | |
| Wed., 2/10 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | ED 1:30 | |
| Wed., 2/10 | V Girls Alpine Skiing | Barlow, Danbury, Southington, Guilford, CA, Weston, LH, Hand | Away | 4:00 p.m. | ||
| Wed., 2/10 | V Girls Ice Hockey | Greenwich | Home [Directions] | 6:00 p.m. | L 0-1 | Terry Conners Rink |
| Thu., 2/11 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/11 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | L 39-43 | |
| Thu., 2/11 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 2/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 2/11 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | JV Boys Ice Hockey | Woodstock Academy | Home - Milford Ice Pavilion [Directions] | 8:30 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ED 1:15 | |
| Fri., 2/12 | V Wrestling | FCIAC Championship at NCHS | Away | 4:00 p.m. | ||
| Fri., 2/12 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 7:30 p.m. | L 2-6 | |
| Sat., 2/13 | V Wrestling | FCIAC Championship at NCHS | Away | 10:00 a.m. | ||
| Sat., 2/13 | V Competitive Cheerleading | Cheer Fest | Away | 10:00 a.m. | Watertown HS | |
| Sat., 2/13 | V Girls Gymnastics | FCIAC Championship at Jonathan Law | Away | 10:30 a.m. | 123.00 | |
| Mon., 2/15 | V Boys Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 12:00 p.m. | W 73-65 | |
| Mon., 2/15 | V Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 12:00 p.m. | L 30-40 | |
| Wed., 2/17 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 54-75 | |
| Wed., 2/17 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Wed., 2/17 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | 8:00 p.m. | W 6-3 | |
| Wed., 2/17 | V Boys Swimming and Diving | Wilton | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Girls Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 40-54 | |
| Wed., 2/17 | JV Girls Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/17 | FR Girls Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/19 | JV Boys Ice Hockey | Trumbull | Home - Milford Ice Pavilion [Directions] | 8:30 p.m. | ||
| Fri., 2/19 | V Boys Swimming and Diving | Danbury | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Fri., 2/19 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:00 p.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 8:00 p.m. | W 6-4 | |
| Sat., 2/20 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/20 | V Boys Swimming and Diving | JV FCIAC at Greenwich HS | Away | 1:00 p.m. | ||
| Sat., 2/20 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ride with boys | |
| Mon., 2/22 | V Boys Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 64065 | |
| Mon., 2/22 | JV Boys Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/22 | FR Boys Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/22 | V Boys Swimming and Diving | FCIAC Trials at Greenwich HS | Away | 4:30 p.m. | ||
| Mon., 2/22 | V Girls Gymnastics | New Milford, Trumbull | Away - New Milford HS [Directions] | Cancelled | Cancelled | |
| Wed., 2/24 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 7:00 p.m. | L 51-66 | |
| Wed., 2/24 | JV Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ride with varsity | |
| Wed., 2/24 | FR Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Boys Squash | Hopkins School | Away | 4:30 p.m. | ride with girls | |
| Wed., 2/24 | V Girls Squash | Hopkins School | Away | 4:30 p.m. | ||
| Fri., 2/26 | V Boys Ice Hockey | Darien | Away - Chelsea Piers [Directions] | 8:15 p.m. | L 3-6 | |
| Fri., 2/26 | V Boys Swimming and Diving | FCIAC Championship at Greenwich HS | Away | 6:30 p.m. | ||
| Fri., 2/26 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavilion [Directions] | 7:15 p.m. | W 6-2 | |
| Sat., 2/27 | V Boys Squash | Fairwest Cup @Chelsea Piers | Away | 1:00 p.m. | ||
| Sat., 2/27 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Sat., 2/27 | V Girls Gymnastics | State Championship @ Pomperaug HS | Away | 11:45 a.m. | ||
| Sat., 2/27 | V Girls Squash | Fairwest Cup @ Chelsea Piers | Home [Directions] | 1:00 p.m. | ||
| Sun., 2/28 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 2/28 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Mon., 2/29 | V Boys Alpine Skiing | Darien, Framington, Pomperaug, Ridgefield | Away | 4:00 p.m. | ||
| Mon., 2/29 | JV Boys Ice Hockey | Guilford | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | ||
| Mon., 2/29 | V Girls Alpine Skiing | Darien, Farmington, Pomperaug, Ridgefield | Away | 4:00 p.m. | ||
| Tue., 3/1 | V Boys Alpine Skiing | Barlow, Danbury, Southington, Guilford, CA, Weston, Hand | Away | 4:00 p.m. | ED 1:30 | |
| Tue., 3/1 | JV Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | 3:00 p.m. | ED 1:15 | |
| Tue., 3/1 | V Girls Alpine Skiing | Barlow, Danbury, Southington, Guilford, CA, Weston, LH, Hand | Away | 4:00 p.m. | ED 1:30 | |
| Wed., 3/2 | V Boys Basketball | Trinity Catholic (Scrim.) | Away - Walsh Court | 3:30 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | East Haven Coop (Scrim.) | Away - DiLungo Rink [Directions] | 6:40 p.m. | ||
| Thu., 3/3 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Milford Ice Pavilion [Directions] | 7:00 p.m. | ||
| Fri., 3/4 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 4:00 p.m. | ||
| Sat., 3/5 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 9:00 a.m. | ||
| Sat., 3/5 | V Competitive Cheerleading | States at Floyd Little Athletic Complex | Away | 8:30 a.m. | ||
| Tue., 3/8 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 6:00 p.m. | ||
| Wed., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Hamden HS [Directions] | 5:30 p.m. | ||
| Thu., 3/10 | V Boys Ice Hockey | Division III Ice Hockey vs. LH/H-K/Cog. | Home [Directions] | 7:15 p.m. | ||
| Fri., 3/11 | V Boys Indoor Track | New Balance Indoor Nationals | Away | TBA | The Armory NYC | |
| Fri., 3/11 | V Boys Rugby | Fairfield Prep (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Sat., 3/12 | V Boys Indoor Track | New Balance Indoor Nationals | Away | TBA | ||
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class LL Qualifying | Away - Hamden HS [Directions] | 3:30 p.m. | ||
| Sun., 3/13 | V Boys Indoor Track | New Balance Indoor Nationals | Away | TBA | ||
| Mon., 3/14 | Unified Sports Basketball | Unified Sports | Away | 2:15 p.m. | accommodate 2 wheelchairs/must stay | |
| Tue., 3/15 | V Boys Ice Hockey | Division III Semi-Finals vs. Woodstock | Away | 7:30 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | ED 10:45 | |
| Thu., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Fri., 3/18 | V Boys Rugby | Stamford Academy (Scrim.) | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Sat., 3/19 | V Boys Ice Hockey | Division III Finals | Away | 10:00 a.m. | Bus leaves from MIP | |
| Sat., 3/19 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Wed., 3/23 | V Boys Rugby | Aspetuck | Home - Staples Stadium [Directions] | 7:00 p.m. | ||
| Thu., 3/24 | V Baseball | Bunnell (Scrim.) | Home - Staples Baseball Field [Directions] | TBA | ||
| Thu., 3/24 | V Boys Lacrosse | Somers (NY) (Scrim.) | Away | 4:00 p.m. | ED 1:30 | |
| Thu., 3/24 | V Co-ed Sailing | Regatta | Away | 4:00 p.m. | ||
| Thu., 3/24 | V Girls Lacrosse | Darien (Scrim.) | Away - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 3/24 | V Softball | Darien (Scrim.) | Away - DHS Softball Varsity Field [Directions] | 3:45 p.m. | ||
| Sat., 3/26 | V Baseball | Oxford (Scrim.) | Away - OHS Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 3/26 | V Boys Lacrosse | Choate/Branford | Home - Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 3/26 | V Girls Lacrosse | Jamboree at Danbury HS | Away | 9:00 a.m. | ||
| Sat., 3/26 | V Softball | Jamboree at Norwich Free Academy | Away | 10:00 a.m. | ||
| Tue., 3/29 | V Baseball | Fairfield Warde (Scrim.) | Away - Fairfield Warde H.S. [Directions] | 3:30 p.m. | ||
| Tue., 3/29 | V Boys Lacrosse | Fairfield Ludlowe (Scrim.) | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Tue., 3/29 | JV Boys Lacrosse | Fairfield Ludlowe (Scrim.) | Away - Taft Field [Directions] | 5:30 p.m. | ||
| Tue., 3/29 | V Girls Lacrosse | New Canaan (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | JV Girls Lacrosse | New Canaan (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Tue., 3/29 | V Softball | Oxford (Scrim.) | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | Joel Barlow (Scrim.) | Home - Staples HS Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 3/30 | FR Boys Lacrosse | Darien (Scrim.) | Away - DHS Turf #2 [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Co-ed Sailing | Greenwich Academy & Darien HS | Home [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | Foran (Scrim.) | Home - Wakeman Field [Directions] | 3:45 p.m. | ||
| Thu., 3/31 | V Girls Lacrosse | Cheshire (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 4:45 p.m. | ||
| Fri., 4/1 | FR Baseball | Joel Barlow (Scrim.) | Home - Wakeman Field [Directions] | 3:30 p.m. | ||
| Fri., 4/1 | V Boys Rugby | Darien | Away [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | V Girls Lacrosse | Greens Farms Academy (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Weston | Home - Staples Stadium [Directions] | 2:00 p.m. | W 15-5 | |
| Sat., 4/2 | JV Boys Lacrosse | Weston | Home - Staples Stadium [Directions] | 3:30 p.m. | ||
| Sat., 4/2 | V Co-ed Sailing | Prep, FL/FW, GFA, DHS, Stam | Away | TBA | Pequot Yacht Club | |
| Sat., 4/2 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Away | TBA | ||
| Tue., 4/5 | JV Boys Golf | Fairfield Ludlowe | Away [Directions] | Cancelled | Cancelled | |
| Tue., 4/5 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | L 7-10 | |
| Tue., 4/5 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Wed., 4/6 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | 4:00 p.m. | W 28-1 | |
| Wed., 4/6 | JV Baseball | Bridgeport Central | Away - Seaside Park Diamond 10 [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | JV Boys Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 4/6 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | W 11-5 | ED 1:30 |
| Wed., 4/6 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Wed., 4/6 | FR Boys Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/6 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/6 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ride with varsity | |
| Wed., 4/6 | V Co-ed Sailing | GHS, RCDS, DHS | Away | TBA | ||
| Wed., 4/6 | FR Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Wed., 4/6 | V Softball | Fairfield Ludlowe | Home - Wakeman Field [Directions] | 4:00 p.m. | L 3-5 | |
| Wed., 4/6 | V Girls Tennis | Trumbull | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/6 | V Girls Water Polo | Greenwich | Away [Directions] | 3:00 p.m. | ED 1:15 | |
| Thu., 4/7 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | W 16-8 | |
| Thu., 4/7 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 4/8 | FR Baseball | Newtown | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Boys Rugby | Ridgefield | Home - PJ Romano Field - Saugatuck Elem School [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Boys Tennis | Stamford | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/8 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 4/8 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 4/8 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Girls Tennis | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/8 | V Girls Water Polo | Choate Rosemary Hall | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Sat., 4/9 | JV Baseball | Amity | Away - John Janenda Baseball Field @ Amity HS [Directions] | 2:00 p.m. | ||
| Sat., 4/9 | FR Baseball | Amity | Home - Wakeman Field [Directions] | Cancelled | Cancelled | |
| Sat., 4/9 | V Boys Lacrosse | Fox Lane (NY) | Home - Staples Stadium [Directions] | 3:00 p.m. | W 14-13 | |
| Sat., 4/9 | JV Boys Lacrosse | Fox Lane (NY) | Home - Staples Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/9 | V Boys Outdoor Track | Bloomfield Invitational | Away | 10:00 a.m. | ||
| Sat., 4/9 | V Girls Outdoor Track | Bloomfield Invitational | Away | 9:00 a.m. | ||
| Sat., 4/9 | V Girls Outdoor Track | Arcadia Tournament | Away | 5:00 p.m. | ||
| Sat., 4/9 | V Girls Water Polo | Suffield Academy | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Sun., 4/10 | V Baseball | Amity | Home - Staples HS Baseball Field [Directions] | 2:00 p.m. | L 5-1 | |
| Sun., 4/10 | V Softball | Greenwich | Home - Wakeman Field [Directions] | 4:00 p.m. | L 7-16 | |
| Mon., 4/11 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | W 6-2 | |
| Mon., 4/11 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | FR Baseball | Trumbull | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 4/11 | V Boys Volleyball | Southington | Away - West Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Mon., 4/11 | JV Boys Volleyball | Southington | Away - West Gym [Directions] | 5:00 p.m. | ||
| Mon., 4/11 | V Softball | Trumbull | Home - Wakeman Field [Directions] | 4:15 p.m. | L 5-7 | |
| Mon., 4/11 | JV Softball | Trumbull | Home - Staples HS - Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Ridgefield | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/12 | V Boys Lacrosse | Trinity Catholic | Home - Staples Stadium [Directions] | 5:30 p.m. | W 19 - 0 | |
| Tue., 4/12 | FR Boys Lacrosse | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | 195-191 | |
| Tue., 4/12 | V Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 11-12(OT) | |
| Tue., 4/12 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Wed., 4/13 | V Baseball | Stamford | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 4/13 | JV Baseball | Stamford | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | FR Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | FR Boys Lacrosse | Joel Barlow | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 4/13 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 4/13 | V Co-ed Sailing | GFA, Stamford | Away | 4:00 p.m. | ||
| Wed., 4/13 | V Softball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | L 0-6 | |
| Wed., 4/13 | JV Softball | Stamford | Away - Cummings Park [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 4/14 | V Boys Lacrosse | St. John The Baptist (NY) | Away | 4:00 p.m. | W 13 - 5 | ED 12:30 |
| Thu., 4/14 | V Boys Tennis | Fairfield Prep | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/14 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Girls Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:30 p.m. | 198-226 | ED 1:35 |
| Thu., 4/14 | JV Girls Golf | Ridgefield | Away [Directions] | 3:00 p.m. | ride with varsity | |
| Thu., 4/14 | V Girls Lacrosse | Newtown | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 16-12 | |
| Thu., 4/14 | JV Girls Lacrosse | Newtown | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Thu., 4/14 | JV Girls Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/15 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | L 2-11 | Ed 1:45 |
| Fri., 4/15 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:00 p.m. | ED 1:45 | |
| Fri., 4/15 | FR Baseball | Ridgefield | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/15 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 4/15 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 4/15 | V Softball | Ridgefield | Home - Wakeman Field [Directions] | 4:30 p.m. | L 3-6 | |
| Fri., 4/15 | JV Softball | Ridgefield | Home - Staples HS - Softball Field [Directions] | 4:30 p.m. | ||
| Sat., 4/16 | V Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | 12:00 p.m. | L 2-4 | |
| Sat., 4/16 | V Boys Lacrosse | Kellenberg Memorial (NY) | Home - Staples Stadium [Directions] | 12:30 p.m. | W 10-2 | |
| Sat., 4/16 | JV Boys Lacrosse | Kellenberg Memorial | Home - Staples Stadium [Directions] | 2:00 p.m. | ||
| Sat., 4/16 | FR Boys Lacrosse | St. Anthonys (NY) | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Sat., 4/16 | V Co-ed Sailing | O'Day Qualifier | Away | TBA | Indian Harbor, small bus | |
| Sat., 4/16 | V Girls Outdoor Track | New York Relays | Away | 9:00 a.m. | ||
| Sun., 4/17 | V Co-ed Sailing | O'Day Finals | Away | TBA | Brown Univ | |
| Mon., 4/18 | V Baseball | Masuk | Home - Staples Baseball Field [Directions] | 4:00 p.m. | W 7-6 | |
| Mon., 4/18 | FR Boys Lacrosse | New Canaan | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Tennis | Greenwich | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 4-3 | |
| Mon., 4/18 | JV Boys Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/18 | JV Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/18 | V Girls Outdoor Track | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Softball | Bridgeport Central | Home - Wakeman Field [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/18 | JV Softball | Bridgeport Central | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/19 | V Boys Lacrosse | Greenwich | Home - Staples Stadium [Directions] | 5:30 p.m. | W 13-12 2OT | |
| Tue., 4/19 | JV Boys Lacrosse | Greenwich | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | V Boys Outdoor Track | Darien | Away - DHS Stadium Field [Directions] | 3:15 p.m. | ||
| Tue., 4/19 | V Boys Tennis | St. Joseph | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/19 | V Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 9-14 | |
| Tue., 4/19 | JV Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Tue., 4/19 | V Girls Tennis | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/20 | V Baseball | Greenwich | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | L 6-9 | |
| Wed., 4/20 | JV Baseball | Greenwich | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | JV Boys Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 4/20 | FR Boys Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Boys Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/20 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/20 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ride with varsity | |
| Wed., 4/20 | V Girls Lacrosse | Conard | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 11-10(OT) | |
| Wed., 4/20 | JV Girls Lacrosse | Conard | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Wed., 4/20 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | 4:00 p.m. | W 23-6 (5 inn) | |
| Wed., 4/20 | V Girls Tennis | Bridgeport Central | Home - Staples HS-Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 4/21 | V Boys Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 4-3 | |
| Thu., 4/21 | V Boys Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-0 [Detailed Results] | |
| Thu., 4/21 | JV Boys Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 15-3 | |
| Thu., 4/21 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Girls Tennis | Westhill | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 4/22 | V Baseball | St. Joseph | Home - Staples HS Baseball Field [Directions] | 3:30 p.m. | L 3-5 | |
| Fri., 4/22 | JV Baseball | St. Joseph | Home - Wakeman Field [Directions] | 3:30 p.m. | ||
| Fri., 4/22 | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 3:30 p.m. | ||
| Fri., 4/22 | FR Boys Lacrosse | Newtown | Home - Wakeman Field B (turf) [Directions] | 3:30 p.m. | ||
| Fri., 4/22 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | 3:00 p.m. | L 0-3 | |
| Fri., 4/22 | JV Softball | St. Joseph | Away - Long Hill Admin.,Trumbull,CT [Directions] | Cancelled | Cancelled | ride with varsity |
| Sat., 4/23 | V Baseball | Montville | Away - Montville H.S. [Directions] | 1:30 p.m. | L 1-6 | Dodd Stadium |
| Sat., 4/23 | V Boys Lacrosse | Trumbull | Home - Staples Stadium [Directions] | 2:00 p.m. | W 16 - 2 | |
| Sat., 4/23 | JV Boys Lacrosse | Trumbull | Home - Staples Stadium [Directions] | 3:30 p.m. | ||
| Mon., 4/25 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | L 0-6 | |
| Mon., 4/25 | JV Baseball | Westhill | Away - Rippowam MS [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | FR Baseball | Westhill | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Golf | Bridgeport Central | Away - Fairchild Wheeler Golf Course [Directions] | 3:15 p.m. | staples 151 central 262 | ED 2:00 |
| Mon., 4/25 | JV Boys Golf | New Canaan | Away [Directions] | 3:30 p.m. | New Canaan Country Club | |
| Mon., 4/25 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/25 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 4/25 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ride with varsity | |
| Mon., 4/25 | V Girls Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | 189-205 | ED 2:00 |
| Mon., 4/25 | JV Girls Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | ||
| Mon., 4/25 | FR Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Mon., 4/25 | V Softball | Westhill | Home - Wakeman Field [Directions] | 4:00 p.m. | L 10-1 | |
| Mon., 4/25 | JV Softball | Westhill | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Girls Tennis | Brien McMahon | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/26 | V Boys Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | Staples 158 Warde 166 | |
| Tue., 4/26 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 6:30 p.m. | L 4 - 7 | |
| Tue., 4/26 | JV Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Golf | Trumbull | Home - Longshore [Directions] | 3:27 p.m. | 190-221 | ED 2:00 |
| Tue., 4/26 | V Girls Lacrosse | Joel Barlow | Away - Field J (competition field) [Directions] | 4:00 p.m. | L 8-12 | |
| Tue., 4/26 | JV Girls Lacrosse | Joel Barlow | Away - Field J (competition field) [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 11-1 | |
| Wed., 4/27 | JV Baseball | Brien McMahon | Away - Roton [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Outdoor Track | Westhill, Ridgefield | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/27 | JV Boys Tennis | Fairfield Ludlowe | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Co-ed Sailing | BS & RHS | Home [Directions] | TBA | ||
| Wed., 4/27 | V Girls Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | 187-193 | ED 2:00 |
| Wed., 4/27 | JV Girls Golf | Greenwich | Home [Directions] | 3:00 p.m. | ||
| Wed., 4/27 | FR Girls Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Girls Outdoor Track | Westhill, Ridgefield | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Softball | Brien McMahon | Home - Wakeman Field [Directions] | 4:00 p.m. | W 8-1 | |
| Wed., 4/27 | JV Softball | Brien McMahon | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Golf | St. Joseph | Home - Longshore [Directions] | 3:00 p.m. | Staples 155, St. Joes 178 | |
| Thu., 4/28 | V Boys Tennis | Norwalk | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/28 | JV Girls Golf | Fairfield Ludlowe, Fairfield Warde | Home - Longshore [Directions] | 3:27 p.m. | ||
| Thu., 4/28 | V Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 8-11 | |
| Thu., 4/28 | JV Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Thu., 4/28 | V Girls Outdoor Track | Penn Relays | Away | TBA | ||
| Thu., 4/28 | V Softball | Bristol Central | Away - Bristol Central HS [Directions] | 3:45 p.m. | L 8-9 | |
| Thu., 4/28 | V Girls Tennis | Norwalk | Away - Norwalk HS [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/28 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | School Holidays and Closings | World Language National Honor Society ceremony | ||||
| Fri., 4/29 | V Baseball | Fairfield Ludlowe | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 4/29 | JV Baseball | Fairfield Ludlowe | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Lacrosse | Ridgefield | Home - Staples Stadium [Directions] | 7:00 p.m. | W 7 - 6 | Sticks for Soldiers |
| Fri., 4/29 | JV Boys Lacrosse | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Fairfield Warde | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Don Bosco Tournament | Away | TBA | ||
| Fri., 4/29 | V Boys Outdoor Track | Dan O'Grady Relays | Away | Cancelled | Cancelled | ED 1:15 |
| Fri., 4/29 | V Boys Rugby | Fairfield Prep | Home - PJ Romano Field - Saugatuck Elem School [Directions] | 3:00 p.m. | ED 1:45 | |
| Fri., 4/29 | V Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/29 | JV Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/29 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | W 8-7 | |
| Fri., 4/29 | JV Softball | Fairfield Ludlowe | Away - Owen Fish Park [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 4/29 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/29 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Girls Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Sat., 4/30 | FR Boys Lacrosse | Don Bosco Tournament | Away | TBA | Don Bosco Prep School 492 Franklin Turnpike Ramsey, NJ 07446 | |
| Sat., 4/30 | V Boys Outdoor Track | Dan O'Grady Relays | Away | 9:00 a.m. | ||
| Sat., 4/30 | V Girls Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | ||
| Sat., 4/30 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 12:30 p.m. | ||
| Sun., 5/1 | V Co-ed Sailing | Herreshoff Women's Regatta | Away | TBA | ||
| Mon., 5/2 | V Baseball | Norwalk | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 10-2 | |
| Mon., 5/2 | JV Baseball | Norwalk | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | FR Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:30 p.m. | Staples167 Wilton 183 | ED 2:00 |
| Mon., 5/2 | JV Boys Golf | Wilton | Away [Directions] | 3:30 p.m. | Rolling Hills | |
| Mon., 5/2 | FR Boys Lacrosse | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Boys Tennis | Darien | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/2 | JV Boys Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 5/2 | JV Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/2 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | 198-203 | ED 1:50 |
| Mon., 5/2 | V Girls Lacrosse | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 6:00 p.m. | W 16-8 | |
| Mon., 5/2 | JV Girls Lacrosse | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 4:30 p.m. | ED 1:45 | |
| Mon., 5/2 | FR Girls Lacrosse | Darien | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | 4:00 p.m. | W 9-8 | |
| Mon., 5/2 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 5/2 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | L 4-3 | |
| Tue., 5/3 | V Boys Golf | Stamford | Away [Directions] | 3:15 p.m. | Staples 165 Stamford 220 | ED 2:00 |
| Tue., 5/3 | V Boys Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | L 5 - 17 | ED 1:30 |
| Tue., 5/3 | JV Boys Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 5:45 p.m. | ||
| Wed., 5/4 | V Boys Golf | Fairfield Ludlowe | Home - Longshore [Directions] | 3:00 p.m. | Staples 152 Ludlow 164 | |
| Wed., 5/4 | JV Boys Golf | Fairfield Ludlowe | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 5/4 | FR Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 5/4 | V Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 5/4 | JV Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/4 | V Co-ed Sailing | GA, Prep, Stam | Away | Cancelled | Cancelled | Indian Harbor, ED 1:45 |
| Wed., 5/4 | V Girls Water Polo | Choate and Suffield | Away | 3:00 p.m. | ||
| Thu., 5/5 | V Baseball | Darien | Home - Staples HS Baseball Field [Directions] | 4:15 p.m. | L 1-6 | |
| Thu., 5/5 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | JV Boys Golf | Wilton | Home - Longshore [Directions] | 3:00 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | W 10-6 | |
| Thu., 5/5 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS - Upper Grass [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Outdoor Track | Stamford | Home - Staples HS [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | Cancelled | Cancelled | |
| Thu., 5/5 | V Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Thu., 5/5 | JV Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | 189-194 | ED 2:00 |
| Thu., 5/5 | JV Girls Golf | Trumbull | Away [Directions] | 3:15 p.m. | ride with varsity | |
| Thu., 5/5 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:15 p.m. | W 17-9 | |
| Thu., 5/5 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | Cancelled | Cancelled | |
| Thu., 5/5 | FR Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Girls Outdoor Track | Stamford | Home [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 9-8 | |
| Thu., 5/5 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 5/5 | JV Girls Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | FR Boys Lacrosse | Stamford | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Boys Outdoor Track | Middletown Invitational (FR & Soph) | Away | 3:30 p.m. | ED 12:30 | |
| Fri., 5/6 | V Boys Outdoor Track | Irv Black Invitational | Away | 3:30 p.m. | ED 12:30 | |
| Fri., 5/6 | V Boys Rugby | Fairfield | Away | 7:00 p.m. | ||
| Fri., 5/6 | FR Girls Lacrosse | Trumbull | Away - Indian Ledge Park [Directions] | 3:30 p.m. | ||
| Fri., 5/6 | V Girls Outdoor Track | FR/SO Invitational | Away | Cancelled | Cancelled | Middletown |
| Fri., 5/6 | JV Softball | New Canaan | Home - Staples HS - Softball Field [Directions] | Cancelled | Cancelled | |
| Sat., 5/7 | V Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 19-3 | |
| Sat., 5/7 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:00 p.m. | ||
| Sat., 5/7 | FR Boys Lacrosse | Don Bosco Tournament | Away | 12:00 p.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Irv Black Invitational | Away | 10:00 a.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Middletown Invitational (varsity) | Away | 1:00 p.m. | ||
| Sat., 5/7 | V Co-ed Sailing | Fairfield Cup | Away | TBA | Pequot Yacht Club | |
| Sat., 5/7 | V Girls Outdoor Track | Middletown Invitational | Away | 9:00 a.m. | ||
| Sat., 5/7 | V Girls Water Polo | Hopkins School | Away | 3:00 p.m. | ||
| Sun., 5/8 | V Co-ed Sailing | Herreshoff Women's Regatta | Away | TBA | ||
| Mon., 5/9 | FR Baseball | Fairfield Country Day School | Home - Staples HS Baseball Field [Directions] | 3:30 p.m. | ||
| Mon., 5/9 | V Boys Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | Staples 146 Ridgefield 153 | |
| Mon., 5/9 | JV Boys Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | ||
| Mon., 5/9 | FR Boys Lacrosse | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Wilton | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/9 | JV Boys Tennis | Wilton | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | W 3-0 | ED 1:45 |
| Mon., 5/9 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ride with varsity | |
| Mon., 5/9 | JV Girls Golf | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | 3:00 p.m. | ED 1:45 Par 3 | |
| Mon., 5/9 | V Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 9-10 | |
| Mon., 5/9 | JV Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Mon., 5/9 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Mon., 5/9 | V Girls Outdoor Track | Danbury, Trumbull | Away - Danbury HS Stadium [Directions] | 4:00 p.m. | ED 1:30 | |
| Mon., 5/9 | V Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/10 | V Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | W 8-0 | |
| Tue., 5/10 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | FR Baseball | New Canaan | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | 3:15 p.m. | Staples 161 Trinity 194 | ED 2:00 |
| Tue., 5/10 | JV Boys Golf | Brien McMahon | Away [Directions] | 3:00 p.m. | Oak Hills CC | |
| Tue., 5/10 | V Boys Lacrosse | Westhill | Home - Staples Stadium [Directions] | 5:30 p.m. | W 15-0 | Senior Day |
| Tue., 5/10 | JV Boys Lacrosse | Westhill | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| Tue., 5/10 | V Boys Outdoor Track | Danbury, Trumbull | Away - Danbury HS Stadium [Directions] | 4:00 p.m. | ED 1:15 | |
| Tue., 5/10 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/10 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Co-ed Sailing | @ Indian Harbor YC | Away | 4:00 p.m. | ||
| Tue., 5/10 | JV Girls Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | ||
| Tue., 5/10 | V Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 16-4 | |
| Tue., 5/10 | JV Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Tue., 5/10 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | L 7-9 | |
| Tue., 5/10 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/10 | JV Girls Tennis | Fairfield Warde | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Baseball | Wilton | Home - Staples HS Baseball Field [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 5/11 | JV Baseball | Wilton | Home - Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | Staples 153 Trumbull 153 | |
| Wed., 5/11 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/11 | V Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 5/11 | JV Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/11 | V Co-ed Sailing | GHS, DHS, BS | Away | TBA | Grass Island, ED 1:45 | |
| Wed., 5/11 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | 6:30 p.m. | L 1-3 | |
| Wed., 5/11 | V Girls Tennis | New Canaan | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 5/11 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | ED 1:50 Ridgefield GC | |
| Thu., 5/12 | V Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | W 11-5 | |
| Thu., 5/12 | JV Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 5:15 p.m. | ||
| Thu., 5/12 | V Boys Outdoor Track | Loucks Games | Away | Cancelled | Cancelled | |
| Thu., 5/12 | V Boys Tennis | Trinity Catholic | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/12 | JV Boys Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Golf | Fairfield Ludlowe, Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | Staples 184, Ludlowe 220 Ridgefield 217 | ED 2:00pm |
| Thu., 5/12 | V Girls Lacrosse | Wilton | Home - Staples Stadium [Directions] | 5:30 p.m. | W 15-10 | |
| Thu., 5/12 | JV Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Outdoor Track | Louckes Games | Away | 4:00 p.m. | ED 1:30 | |
| Thu., 5/12 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | W 7-0 | |
| Thu., 5/12 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | FR Boys Lacrosse | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Boys Outdoor Track | Loucks Games | Away | TBA | ||
| Fri., 5/13 | V Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 4:30 p.m. | ||
| Fri., 5/13 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/13 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ride with varsity | |
| Fri., 5/13 | FR Girls Lacrosse | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Fri., 5/13 | V Girls Outdoor Track | Louckes Games | Away | 4:00 p.m. | ED 1:30 | |
| Sat., 5/14 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 11:00 a.m. | L 12-4 | |
| Sat., 5/14 | V Boys Outdoor Track | Greater Hartford Invitational | Away | 9:30 a.m. | Simsbury | |
| Sat., 5/14 | V Boys Outdoor Track | Loucks Games | Away | TBA | ||
| Sat., 5/14 | V Girls Outdoor Track | Hillhouse Invitational | Away | Cancelled | Cancelled | |
| Sat., 5/14 | V Girls Outdoor Track | Louckes Games | Away | 9:00 a.m. | ||
| Sat., 5/14 | V Girls Water Polo | Hotchkiss | Home - Staples HS Pool [Directions] | Cancelled | Cancelled | |
| Sun., 5/15 | V Softball | Fairfield Warde | Home - Wakeman Field [Directions] | 4:00 p.m. | L 14-2 | |
| Mon., 5/16 | V Baseball | Trinity Catholic | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 24-3 | |
| Mon., 5/16 | JV Baseball | Trinity Catholic | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Boys Golf | Westhill, Norwalk | Home - Longshore [Directions] | 3:00 p.m. | Staples 165, Westhill 170, Norwalk 210 | |
| Mon., 5/16 | JV Boys Golf | Brien McMahon | Home - Longshore [Directions] | Cancelled | Cancelled | |
| Mon., 5/16 | V Boys Tennis | Danbury | Away - Danbury HS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/16 | V Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Mon., 5/16 | JV Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/16 | JV Girls Golf | Greenwich | Away [Directions] | 3:00 p.m. | ED 1:30 Millbook Club | |
| Mon., 5/16 | FR Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Girls Outdoor Track | Greenwich | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Softball | Trinity Catholic | Away - Westhill HS | 4:00 p.m. | L 1-7 | |
| Mon., 5/16 | V Girls Tennis | Danbury | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/16 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | FR Baseball | Fairfield Warde | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | JV Boys Golf | Fairfield Prep | Away - Patterson Club, Fairfield, CT [Directions] | 3:00 p.m. | Patterson Club | |
| Tue., 5/17 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | Greenwich | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Weston | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/17 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Tue., 5/17 | V Co-ed Sailing | Indian Harbor Yacht Club | Away | TBA | ||
| Tue., 5/17 | V Girls Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | 178-237 | ED 2:00 |
| Tue., 5/17 | JV Girls Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | ||
| Tue., 5/17 | V Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | W 11-7 | |
| Tue., 5/17 | JV Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Softball | New Canaan | Home - Greens Farms Elementary School [Directions] | 6:30 p.m. | W 8-3 | |
| Tue., 5/17 | V Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:15 p.m. | W 4-3 | ED 1:55 |
| Tue., 5/17 | V Girls Tennis | Joel Barlow (Scrim.) | Home - Staples HS-Tennis Courts [Directions] | Cancelled | Cancelled | |
| Tue., 5/17 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | L 1-3 | ED 1:45 |
| Wed., 5/18 | JV Baseball | Danbury | Away - Danbury HS Junior Varsity Baseball Field [Directions] | 4:00 p.m. | ED 1:45 | |
| Wed., 5/18 | FR Baseball | Danbury | Home - Staples HS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/18 | V Boys Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | Staples 150 Danbury 157 | |
| Wed., 5/18 | V Boys Lacrosse | Brien McMahon | Home - Staples Stadium [Directions] | 5:30 p.m. | W 16-3 | |
| Wed., 5/18 | JV Boys Lacrosse | Brien McMahon | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:00 p.m. | 185-176 | ED 2:00 |
| Wed., 5/18 | JV Girls Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 5/18 | V Girls Outdoor Track | FR & Soph Last chance qualifier | Away | 4:00 p.m. | ||
| Wed., 5/18 | V Softball | Danbury | Home - Wakeman Field [Directions] | 4:00 p.m. | L 5-3 (9 inn) | |
| Wed., 5/18 | JV Softball | Danbury | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Tennis | FCIAC Playdowns vs. Wilton | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | JV Girls Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Water Polo | Chelsea Piers | Home - Staples HS Pool [Directions] | 4:30 p.m. | ||
| Thu., 5/19 | JV Baseball | Darien | Home - Staples Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Boys Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | Staples 147 Darien 140 | |
| Thu., 5/19 | JV Boys Golf | Fairfield Prep | Home - Longshore [Directions] | 3:00 p.m. | ||
| Thu., 5/19 | FR Boys Lacrosse | Ridgefield | Home - Wakeman Field E (grass) [Directions] | 5:00 p.m. | ||
| Thu., 5/19 | V Boys Tennis | FCIAC Playdowns vs. Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 5/19 | V Boys Tennis | FCIAC Playdowns vs. Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | 3:15 p.m. | 168-172 | ED 2:00 |
| Thu., 5/19 | JV Girls Golf | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | 3:00 p.m. | ED 1:45 Par 3 | |
| Fri., 5/20 | JV Boys Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | V Girls Tennis | FCIAC Semi-finals vs. New Canaan | Home - Staples HS-Tennis Courts [Directions] | 2:00 p.m. | ED 1:00 | |
| Sat., 5/21 | V Boys Lacrosse | Greenwich | Home - Staples Stadium [Directions] | 12:00 p.m. | W 13-8 | |
| Sat., 5/21 | V Boys Outdoor Track | FCIAC Championships | Away | 10:00 a.m. | Bethel HS | |
| Sat., 5/21 | V Co-ed Sailing | High School Mark Trophy | Away | TBA | ||
| Sat., 5/21 | V Girls Outdoor Track | FCIAC Championship @ Bethel HS | Away | 10:00 a.m. | ||
| Sat., 5/21 | V Girls Water Polo | Hotchkiss | Away | 1:30 p.m. | ||
| Sun., 5/22 | V Co-ed Sailing | High School Mark Trophy | Away | TBA | ||
| Mon., 5/23 | V Boys Tennis | FCIAC Semi-Finals vs. New Canaan | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Girls Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | 184-203 | ED 2:00 |
| Mon., 5/23 | Unified Sports Track | Fairfield Ludlowe | Away [Directions] | 3:00 p.m. | 2 wheelchairs, bus to stay | |
| Tue., 5/24 | V Boys Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | Staples 148 Greenwich 143 | |
| Tue., 5/24 | JV Boys Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | Darien | Away [Directions] | 7:30 p.m. | L 4-14 | |
| Tue., 5/24 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | 181-204 | ED 2:00 |
| Tue., 5/24 | V Girls Tennis | FCIAC Finals vs. Darien @ Shippan Racquet Club | Away | 2:00 p.m. | ED 12:45 | |
| Wed., 5/25 | V Boys Golf | Brien McMahon, New Canaan | Home - Longshore [Directions] | 3:00 p.m. | 146 | |
| Wed., 5/25 | V Boys Outdoor Track | Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/25 | V Boys Tennis | FCIAC Finals vs. Greenwich @ Wilton | Away | 4:00 p.m. | ||
| Wed., 5/25 | V Boys Volleyball | Ridgefield | Home [Directions] | 7:00 p.m. | L 1-3 | |
| Wed., 5/25 | JV Girls Golf | Ekstrom JV FCIAC Tournament | Away | TBA | ||
| Wed., 5/25 | V Girls Outdoor Track | Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/25 | V Softball | Darien (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Boys Golf | Chappa Tournament | Home - Longshore [Directions] | TBA | ||
| Thu., 5/26 | V Boys Outdoor Track | Hatter Freshman Invitational | Away | 4:00 p.m. | ED 1:30 Danbury HS | |
| Thu., 5/26 | V Boys Outdoor Track | Dream Invitational | Away | 7:00 p.m. | ||
| Sat., 5/28 | V Boys Tennis | Class LL State Championship @ Yale University Tennis Courts | Away | TBA | ||
| Mon., 5/30 | V Girls Tennis | Class LL First Round vs. Hamden/Trumbull winner | Home - Staples HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Mon., 5/30 | V Girls Tennis | Class LL First Round vs. Hamden/Trumbull winner | Home - Staples HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Tue., 5/31 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 3:30 p.m. | ED 1:45 | |
| Tue., 5/31 | V Boys Golf | Holahan Tournament @ Woodway CC | Away | 12:30 p.m. | ||
| Tue., 5/31 | V Girls Golf | Guimares Tournament | Away | TBA | ED 11:20 | |
| Tue., 5/31 | V Girls Lacrosse | Class L First Round vs Glastonbury | Away | 5:00 p.m. | ||
| Wed., 6/1 | V Baseball | Southington | Away [Directions] | 3:30 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Trumbull | Home - Staples Stadium [Directions] | 4:30 p.m. | W 9 - 4 | |
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 2:30 p.m. | ||
| Wed., 6/1 | V Boys Volleyball | Shelton | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 2:30 p.m. | ||
| Wed., 6/1 | V Girls Tennis | Class L Quarterfinal vs. New Canaan | Home - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Thu., 6/2 | V Boys Golf | FCIAC Finals | Away | 12:00 p.m. | ED 11:00 | |
| Thu., 6/2 | V Girls Golf | FCIAC Finals | Away | 9:00 a.m. | Fairchild Wheeler | |
| Thu., 6/2 | V Girls Tennis | Glastonbury | Away [Directions] | 3:00 p.m. | ||
| Fri., 6/3 | V Boys Volleyball | Conard | Away - Conard HS [Directions] | 5:00 p.m. | ||
| Fri., 6/3 | V Girls Tennis | Greenwich | Away [Directions] | 2:30 p.m. | ED 12:45 | |
| Sat., 6/4 | V Boys Lacrosse | Ridgefield | Home - Staples Stadium [Directions] | 2:30 p.m. | L 5 - 13 | |
| Mon., 6/6 | V Boys Golf | CIAC Div. I Championship | Away - Tallwood CC - Hebron [Directions] | 7:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Tue., 6/7 | V Boys Volleyball | Darien | Away [Directions] | 6:00 p.m. | ||
| Tue., 6/7 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 7:00 a.m. | ||
| Sat., 6/11 | V Boys Outdoor Track | New England Championship | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Sat., 6/11 | V Girls Outdoor Track | New England Championship | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park | 11:30 a.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Wed., 6/22 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||
| Wed., 6/22 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||