| Staples 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1100 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | FR Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | TBA | ||
| TBA | SO Football | Stamford | Away - Stamford High School [Directions] | TBA | ||
| TBA | V Boys Ice Hockey | JBWA (Scrim.) | Away - Danbury Ice Arena [Directions] | TBA | Danbury Ice Rink | |
| TBA | V Boys Tennis | Amity | Home - Staples HS-Tennis Courts [Directions] | TBA | ||
| TBA | JV Boys Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | TBA | ride with varsity | |
| TBA | FR Girls Basketball | Trumbull | Home - Staples High School [Directions] | TBA | ||
| TBA | V Girls Golf | Tournament Game - Opponent Not Known | Away | 8:00 a.m. | ||
| TBA | V Girls Gymnastics | Ro Carlucci Invitational | Away | TBA | ||
| TBA | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ride with varsity | |
| TBA | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Wed., 8/28 | V Football | Naugatuck (Scrim.) | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | V Boys Soccer | Fairfield Prep (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Fri., 8/30 | V Boys Soccer | Wethersfield (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Fri., 8/30 | V Field Hockey | Bethel (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 8/30 | JV Field Hockey | Bethel (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Sat., 8/31 | V Girls Soccer | Tournament @ Conard HS | Away | TBA | ||
| Sun., 9/1 | FR Football | Ridgefield (Scrim.) | Away - Tiger Hollow Stadium [Directions] | 1:00 p.m. | ||
| Tue., 9/3 | V Football | Fairfield Prep (Scrim.) | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/3 | V Boys Soccer | Newtown (Scrim.) | Away - Treadwell Town Park--Tilson Field [Directions] | 4:00 p.m. | ||
| Tue., 9/3 | V Field Hockey | Brien McMahon (Scrim.) | Away [Directions] | 6:00 p.m. | W 1-3 | |
| Fri., 9/6 | V Boys Soccer | Choate Rosemary Hall (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 5:15 p.m. | ||
| Fri., 9/6 | V Field Hockey | Fairfield Warde (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 3:30 p.m. | T 1-1 | |
| Fri., 9/6 | V Girls Soccer | Pomperaug (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Fri., 9/6 | FR Girls Soccer | Pomperaug (Scrim.) | Away - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Sat., 9/7 | V Boys Cross Country | Blue vs. White Time Trial | Home [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Boys Soccer | Wethersfield Jamboree | Away | 10:00 a.m. | ||
| Sat., 9/7 | V Girls Cross Country | Blue and White Time Trial | Home - Staples Stadium [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Girls Volleyball | Val Dickinson Memorial Jamboree | Home - Staples H.S. Gym [Directions] | 9:00 a.m. | ||
| Mon., 9/9 | V Girls Soccer | Greenwich Academy (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Mon., 9/9 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Danbury, Brien McMahon, Westhill, Darien | Away - Tarrywile Park [Directions] | 4:00 p.m. | ED 1:15, 2 buses | |
| Tue., 9/10 | V Boys Soccer | Danbury | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/10 | JV Boys Soccer | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-2 | |
| Tue., 9/10 | FR Boys Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 9/10 | V Girls Cross Country | Danbury, Brien McMahon, Westhill, Darien | Away - Tarrywile Park [Directions] | 4:00 p.m. | Staples 17 - Danbury 43 Staples 21 - Darien 38 Staples 19- Westhill 44 | ED 1:15 |
| Tue., 9/10 | V Field Hockey | Trumbull | Home - Staples Stadium [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 9/10 | JV Field Hockey | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | W 3-1 | |
| Tue., 9/10 | FR Field Hockey | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | W 1-3 | |
| Wed., 9/11 | V Football | Xavier | Away - Palmer Field [Directions] | 6:30 p.m. | L 22-30 | ED, 2 buses |
| Wed., 9/11 | V Boys Water Polo | Greenwich Y | Away | 7:00 p.m. | ||
| Wed., 9/11 | V Competitive Cheerleading | Xavier | Away [Directions] | 6:30 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 6-0 | |
| Wed., 9/11 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | ||
| Thu., 9/12 | JV Football | Xavier | Away - Xavier H.S. [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | FR Football | Xavier | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/12 | V Boys Soccer | New Canaan | Away - Connor Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 9/12 | JV Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 9/12 | FR Boys Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 9/12 | V Girls Volleyball | Norwalk | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/12 | JV Girls Volleyball | Norwalk | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 9/16 | V Boys Soccer | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 4:00 p.m. | L 3-2 | |
| Mon., 9/16 | V Boys Water Polo | Horace Mann (NY) | Away | 4:00 p.m. | ED 2:00 | |
| Mon., 9/16 | FR Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 9/16 | JV Girls Volleyball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | FR Girls Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Boys Cross Country | New Canaan, Wilton, Brien McMahon, Bassick, Trinity Catholic | Away [Directions] | 4:00 p.m. | ED 1:15, 2 buses | |
| Tue., 9/17 | V Girls Cross Country | New Canaan, Wilton, Brien McMahon, Bassick, Trinity Catholic | Away [Directions] | 4:00 p.m. | ED 1:15 | |
| Tue., 9/17 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/17 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Boys Soccer | Ridgefield | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 2-2 | |
| Wed., 9/18 | JV Boys Soccer | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 9/18 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:15 p.m. | W 2-1 | |
| Wed., 9/18 | V Boys Water Polo | Suffield Academy | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 9/18 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 3-0 | |
| Wed., 9/18 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | L 0-4 | |
| Wed., 9/18 | FR Field Hockey | Darien | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 9/18 | V Girls Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 4:00 p.m. | Staples 94 Ridgefield 92 | |
| Wed., 9/18 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/18 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | FR Girls Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | FR Football | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Fairfield Ludlowe | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 9/19 | JV Girls Soccer | Fairfield Ludlowe | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Football | Wilton | Home - Staples Stadium [Directions] | 7:00 p.m. | W 14-7 | Homecoming |
| Fri., 9/20 | JV Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 9/20 | FR Field Hockey | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 5-1 | |
| Fri., 9/20 | V Girls Soccer | Bridgeport Central | Home - Loeffler Field - Staples HS [Directions] | 3:30 p.m. | W 8-0 | |
| Fri., 9/20 | V Girls Swimming and Diving | Danbury | Home - Staples HS Pool [Directions] | 3:30 p.m. | 99-49 | |
| Fri., 9/20 | JV Girls Swimming and Diving | Greenwich | Away [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 9/20 | V Girls Volleyball | Harding | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/20 | JV Girls Volleyball | Harding | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Sat., 9/21 | V Boys Cross Country | Stratton Brook Invitational | Away | 9:00 a.m. | 2 buses | |
| Sat., 9/21 | V Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | W 2-1 | |
| Sat., 9/21 | V Girls Cross Country | Bethel Invitational | Away | 9:00 a.m. | ||
| Sat., 9/21 | V Field Hockey | Daniel Hand | Away - DHHS Turf Field [Directions] | 3:00 p.m. | OT-L 1-2 | |
| Sat., 9/21 | JV Field Hockey | Daniel Hand | Away - DHHS Turf Field [Directions] | 4:30 p.m. | L 1-0 | |
| Mon., 9/23 | JV Football | Wilton | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 9/23 | V Boys Soccer | Bridgeport Central | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 9/23 | JV Boys Soccer | Bridgeport Central | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 9/23 | FR Boys Soccer | Bridgeport Central | Away - Bridgeport Central [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 9/23 | V Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Mon., 9/23 | JV Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:45 p.m. | ||
| Mon., 9/23 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Fairfield Warde, Brien McMahon, Ridgefield, Norwalk | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Fairfield Warde, Brien McMahon, Ridgefield, Norwalk | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | L 1-0 | |
| Tue., 9/24 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:15 p.m. | W 0-1 | |
| Tue., 9/24 | FR Field Hockey | Westhill | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | L 3-1 | ED 1:45 |
| Tue., 9/24 | JV Girls Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | ED 1:45 | |
| Tue., 9/24 | FR Girls Soccer | Danbury | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 9/25 | JV Boys Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | L 3-0 | |
| Wed., 9/25 | FR Boys Soccer | Wilton | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/25 | V Boys Water Polo | Loomis Chaffee School | Home - Staples HS Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/25 | V Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | 6:30 p.m. | W 1-0 | |
| Wed., 9/25 | JV Girls Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | FR Girls Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | L 2-3 | ED 2:00 |
| Wed., 9/25 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ED 2:00 | |
| Wed., 9/25 | FR Girls Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Field Hockey | Norwalk | Home - Staples Stadium [Directions] | 6:00 p.m. | W 2-1 | |
| Thu., 9/26 | JV Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 9/26 | FR Field Hockey | Norwalk | Away - NHS Grass Field [Directions] | 5:30 p.m. | T 1-1 | |
| Fri., 9/27 | FR Football | Westhill | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/27 | V Girls Soccer | Ridgefield | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 3-0 | |
| Fri., 9/27 | JV Girls Soccer | Ridgefield | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | FR Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 3:30 p.m. | ||
| Sat., 9/28 | V Boys Cross Country | Wilton Invitational (Allen's Meadow) | Away | 9:00 a.m. | 2 buses | |
| Sat., 9/28 | V Football | Westhill | Away - Westhill Football Field [Directions] | 1:30 p.m. | W 63-14 | 2 buses |
| Sat., 9/28 | V Boys Soccer | Brien McMahon | Home - Loeffler Field - Staples HS [Directions] | 11:00 a.m. | W 5-1 | |
| Sat., 9/28 | JV Boys Soccer | Brien McMahon | Home - Loeffler Field - Staples HS [Directions] | 1:00 p.m. | W 4-1 | |
| Sat., 9/28 | V Boys Water Polo | Greenwich High School Tournament | Away | TBA | ||
| Sat., 9/28 | V Competitive Cheerleading | Westhill | Away [Directions] | 1:30 p.m. | ||
| Sat., 9/28 | V Girls Cross Country | Bethel Invitational | Away | 9:00 a.m. | Cancelled | |
| Sun., 9/29 | V Boys Water Polo | Greenwich High School Tournament | Away | TBA | ||
| Mon., 9/30 | JV Football | Westhill | Away - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | L 2-0 | |
| Mon., 9/30 | JV Girls Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | FR Girls Soccer | Wilton | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 9/30 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | ||
| Mon., 9/30 | FR Girls Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Greenwich, St. Joseph, Brien McMahon, Trumbull, Harding | Away [Directions] | 4:00 p.m. | ED 1:15, 2 buses | |
| Tue., 10/1 | V Boys Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | 4:00 p.m. | W 5-0 | |
| Tue., 10/1 | V Girls Cross Country | Greenwich, St. Joseph, Brien McMahon, Trumbull, Harding | Away [Directions] | 4:00 p.m. | ED 1:15 | |
| Tue., 10/1 | V Field Hockey | Stamford | Home - Staples Stadium [Directions] | 6:15 p.m. | W 4-3 | |
| Tue., 10/1 | JV Field Hockey | Stamford | Home - Ginny Parker Field - Staples [Directions] | 4:45 p.m. | W 4-0 | |
| Wed., 10/2 | V Boys Water Polo | Brunswick School | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Wed., 10/2 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | L 0-1 | |
| Wed., 10/2 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | FR Girls Soccer | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | 99-85 | ED 1:45 |
| Wed., 10/2 | JV Girls Swimming and Diving | Greenwich | Home - Staples HS Pool [Directions] | 6:00 p.m. | ||
| Wed., 10/2 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/2 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Football | Stamford | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/3 | V Boys Soccer | Norwalk | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/3 | JV Boys Soccer | Norwalk | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 10/4 | V Football | Stamford | Away - Stamford High School [Directions] | 6:00 p.m. | W 41-14 | 2 buses |
| Fri., 10/4 | FR Boys Soccer | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 10/4 | V Competitive Cheerleading | Stamford | Away [Directions] | 6:00 p.m. | ||
| Fri., 10/4 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 2-0 | |
| Fri., 10/4 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | W 4-0 | |
| Fri., 10/4 | V Girls Soccer | St. Joseph | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 0-5 | |
| Fri., 10/4 | JV Girls Soccer | St. Joseph | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Girls Swimming and Diving | East Lyme | Away - East Lyme High School Pool [Directions] | 3:30 p.m. | 90-96 | ED 1:15 |
| Fri., 10/4 | V Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 10/4 | JV Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/4 | FR Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | JV Football | Stamford | Away - Stamford High School [Directions] | 10:00 a.m. | ||
| Sat., 10/5 | JV Girls Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 12:00 p.m. | ||
| Sat., 10/5 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Boys Water Polo | Canterbury | Home [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | 98-88 | |
| Mon., 10/7 | V Girls Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/7 | JV Girls Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Fairfield Ludlowe, Brien McMahon, Stamford, Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | Fairfield Ludlowe, Brien McMahon, Stamford, Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 6:00 p.m. | L 0-5 | |
| Tue., 10/8 | FR Field Hockey | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 2-0 | |
| Tue., 10/8 | V Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:30 p.m. | W 2-0 | |
| Tue., 10/8 | JV Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:30 p.m. | ||
| Tue., 10/8 | FR Girls Soccer | Trumbull | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | V Boys Soccer | Trumbull | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/9 | JV Boys Soccer | Trumbull | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | L 1-0 | |
| Wed., 10/9 | FR Boys Soccer | Trumbull | Away - JV Grass Soccer Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/9 | V Boys Water Polo | Greenwich Y | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Wed., 10/9 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | L 3-0 | |
| Wed., 10/9 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | W 3-0 | ED 2:00 |
| Wed., 10/9 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | 109-77 | ED 1:30 |
| Wed., 10/9 | JV Girls Swimming and Diving | Westhill/Stamford | Away [Directions] | TBA | ||
| Wed., 10/9 | V Girls Volleyball | Bassick | Away [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/9 | JV Girls Volleyball | Bassick | Away [Directions] | 5:30 p.m. | ||
| Wed., 10/9 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | FR Football | Fairfield Ludlowe | Home - Wrecker Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/10 | V Girls Soccer | Greenwich | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 2-0 | |
| Thu., 10/10 | JV Girls Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Football | Fairfield Ludlowe | Home - Staples Stadium [Directions] | 7:00 p.m. | W 52-23 | |
| Fri., 10/11 | FR Boys Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/11 | V Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 3-2 | |
| Fri., 10/11 | JV Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Fri., 10/11 | FR Field Hockey | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 10/11 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | 72-106 | ED 1:30 |
| Fri., 10/11 | V Girls Volleyball | Darien | Away [Directions] | 7:00 p.m. | W 3-2 | |
| Fri., 10/11 | JV Girls Volleyball | Darien | Away [Directions] | 5:30 p.m. | ||
| Fri., 10/11 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/12 | V Boys Cross Country | Wickham Park Invitational | Away | 9:40 a.m. | ||
| Sat., 10/12 | JV Football | Fairfield Ludlowe | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 3:00 p.m. | L 4-1 | |
| Sat., 10/12 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 3:00 p.m.. | T 1-1 | |
| Sat., 10/12 | V Boys Water Polo | Suffield Academy | Home - Staples HS Pool [Directions] | 1:00 p.m. | ||
| Sat., 10/12 | V Girls Cross Country | Wickham Park Invitational | Away | 9:40 a.m. | ||
| Sat., 10/12 | FR Girls Soccer | Greenwich | Away - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | JV Girls Swimming and Diving | Darien, New Canaan | Home - Staples HS Pool [Directions] | 10:00 a.m. | ||
| Mon., 10/14 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 10/15 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | W 3-2 | |
| Tue., 10/15 | JV Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | T 0-0 | |
| Tue., 10/15 | FR Boys Soccer | Darien | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/15 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | L 2-0 | |
| Tue., 10/15 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | L 2-0 | |
| Tue., 10/15 | FR Field Hockey | Wilton | Home - Staples Stadium [Directions] | 6:15 p.m. | W 2-1 | |
| Tue., 10/15 | V Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 10/15 | JV Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Tue., 10/15 | FR Girls Volleyball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | SO Football | Darien | Home [Directions] | 6:00 p.m. | ||
| Wed., 10/16 | FR Girls Soccer | Fairfield Ludlowe | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 4:00 p.m. | 82-96 | |
| Wed., 10/16 | V Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/16 | JV Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/16 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Boys Cross Country | FCIAC Championship @ Waveny Park | Away | 2:30 p.m. | ED 11:30, 2 buses | |
| Thu., 10/17 | FR Football | Danbury | Away - Danbury High School Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/17 | V Boys Soccer | Fairfield Warde | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 10/17 | JV Boys Soccer | Fairfield Warde | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 10/17 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | W 4-0 | |
| Thu., 10/17 | V Girls Cross Country | FCIAC Championship @ Waveny Park | Away | 2:30 p.m. | ED 11:30 | |
| Thu., 10/17 | V Field Hockey | Fairfield Ludlowe | Home - Staples Stadium [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 10/17 | JV Field Hockey | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | T 1-1 | |
| Thu., 10/17 | FR Field Hockey | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Football | Danbury | Home - Staples Stadium [Directions] | 7:00 p.m. | W 43-34 | |
| Fri., 10/18 | V Boys Water Polo | Horace Mann (NY) | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Girls Soccer | Darien | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 1-4 | |
| Fri., 10/18 | JV Girls Soccer | Darien | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | FR Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | W 3-0 | |
| Fri., 10/18 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Sat., 10/19 | JV Football | Danbury | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/19 | V Field Hockey | Hall | Home - Ginny Parker Field - Staples [Directions] | 12:00 p.m. | W 2-0 | |
| Sat., 10/19 | JV Field Hockey | Hall | Home - Ginny Parker Field - Staples [Directions] | 1:30 p.m. | ||
| Sat., 10/19 | JV Girls Soccer | Pomperaug | Home - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | ||
| Sat., 10/19 | JV Girls Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 10:00 a.m. | Cancelled | |
| Mon., 10/21 | V Boys Soccer | Fairfield Ludlowe | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 2-1 | |
| Mon., 10/21 | JV Boys Soccer | Fairfield Ludlowe | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 10/21 | FR Boys Soccer | Fairfield Ludlowe | Away - RLMS [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 10/21 | V Field Hockey | Danbury | Home - Staples Stadium [Directions] | 6:15 p.m. | L 1-0 | |
| Mon., 10/21 | JV Field Hockey | Danbury | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | ||
| Mon., 10/21 | FR Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-1 | |
| Mon., 10/21 | JV Girls Soccer | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Swimming and Diving | Fairfield Warde | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/21 | JV Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | FR Girls Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Cross Country | Bethel JV Tournament | Away | 4:00 p.m. | ED 1:30 | |
| Tue., 10/22 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-0 | |
| Tue., 10/22 | JV Boys Soccer | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/22 | V Girls Cross Country | Bethel JV Invitational | Away | 4:00 p.m. | ED 1:30 | |
| Wed., 10/23 | FR Boys Soccer | Westhill | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Boys Water Polo | Brunswick School | Away | 3:30 p.m. | ||
| Wed., 10/23 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 4-1 | |
| Wed., 10/23 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 10/23 | FR Field Hockey | Westhill | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/23 | JV Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/23 | FR Girls Volleyball | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | V Boys Cross Country | Danbury Freshmen Invitational | Away | 3:45 p.m. | ED 1:15 | |
| Thu., 10/24 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/24 | V Girls Cross Country | Danbury Freshmen Invitational | Away | 3:45 p.m. | ED 1:15 | |
| Thu., 10/24 | JV Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 3:30 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Trinity Catholic | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 8-0 | |
| Fri., 10/25 | V Football | New Canaan | Home - Staples Stadium [Directions] | 7:00 p.m. | L 7-43 | |
| Fri., 10/25 | V Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/25 | JV Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 3:10 p.m. | 2 buses | |
| Sat., 10/26 | JV Football | New Canaan | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/26 | V Boys Soccer | Wilton | Home - Loeffler Field - Staples HS [Directions] | 12:00 p.m. | L 2-0 | |
| Sat., 10/26 | V Boys Soccer | Wilton | Home - Loeffler Field - Staples HS [Directions] | 12:00 p.m. | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:20 a.m. | ||
| Sat., 10/26 | JV Girls Swimming and Diving | JV FCIACs | Away | 4:30 p.m. | ||
| Mon., 10/28 | V Girls Swimming and Diving | FCIAC Trials @ Greenwich HS | Away | 4:00 p.m. | ||
| Mon., 10/28 | V Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | V Girls Swimming and Diving | FCIAC Diving Finals | Away | 4:00 p.m. | ||
| Wed., 10/30 | V Girls Swimming and Diving | FCIAC Finals | Away | 4:00 p.m. | ||
| Wed., 10/30 | V Girls Volleyball | FCIAC Semi-finals vs. Darien | Away | 7:00 p.m. | ||
| Thu., 10/31 | FR Football | Trumbull | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Fri., 11/1 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ED 10:00 | |
| Fri., 11/1 | V Football | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | W 49-42 (OT) | 2 buses |
| Fri., 11/1 | V Boys Soccer | Masuk (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 3:45 p.m. | ||
| Fri., 11/1 | V Boys Water Polo | Loomis Chaffee School | Away | 4:30 p.m. | ||
| Fri., 11/1 | V Competitive Cheerleading | Trumbull | Away [Directions] | 7:00 p.m. | ||
| Fri., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ED 10:00 | |
| Sat., 11/2 | V Girls Volleyball | FCIAC Finals vs. Greenwich @ Ludlowe | Away | 4:00 p.m. | ||
| Mon., 11/4 | JV Football | Trumbull | Away - McDougall Stadium [Directions] | 3:45 p.m. | ||
| Mon., 11/4 | V Field Hockey | Class L Qualifying Round @ Amity | Away | 2:00 p.m. | ED 11:45 | |
| Mon., 11/4 | V Girls Soccer | CIAC Class LL First Round vs. Danbury | Away | 4:00 p.m. | ED 1:45 | |
| Tue., 11/5 | V Boys Soccer | Norwalk | Home [Directions] | 2:00 p.m. | W 1-0 | |
| Tue., 11/5 | V Boys Soccer | Newtown | Home [Directions] | 2:00 p.m. | W 1-0 | |
| Wed., 11/6 | V Field Hockey | Class L First Round vs. Greenwich | Away | 2:00 p.m. | ||
| Wed., 11/6 | V Girls Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Bulkeley HS [Directions] | 4:30 p.m. | ||
| Thu., 11/7 | SO Football | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/7 | FR Football | Bridgeport Central | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/7 | V Boys Soccer | Newtown | Away [Directions] | 6:00 p.m. | ||
| Thu., 11/7 | V Girls Volleyball | Class LL Second Round vs. Danbury | Home [Directions] | 5:00 p.m. | ||
| Fri., 11/8 | V Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 7:00 p.m. | W 42-26 | 2 buses |
| Fri., 11/8 | V Competitive Cheerleading | Bridgeport Central | Away [Directions] | 7:00 p.m. | ||
| Sat., 11/9 | V Boys Cross Country | New England Championship | Away - Derryfield Park-Manchester, NH [Directions] | TBA | ED 10:30 | |
| Sat., 11/9 | V Boys Soccer | Xavier | Away - Oakwood Soccer Park, Portland [Directions] | 6:00 p.m. | L 1-0 | |
| Sat., 11/9 | V Boys Water Polo | Hopkins School | Away | TBA | ||
| Sat., 11/9 | V Girls Cross Country | New England Championship | Away - Derryfield Park-Manchester, NH [Directions] | TBA | ED 10:30am | |
| Sat., 11/9 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 6:00 p.m. | ||
| Sat., 11/9 | V Girls Volleyball | CIAC CLass LL Quarterfinal vs. Simsbury at Weston HS | Home [Directions] | 4:00 p.m. | ||
| Mon., 11/11 | JV Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 11/12 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - SCSU. [Directions] | 6:00 p.m. | ||
| Thu., 11/14 | FR Football | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | ||
| Thu., 11/14 | V Girls Volleyball | Greenwich | Away [Directions] | 5:00 p.m. | ||
| Fri., 11/15 | V Football | Norwalk | Home - Staples Stadium [Directions] | 6:00 p.m. | W 48-13 | |
| Fri., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Mon., 11/18 | JV Football | Greenwich | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/21 | FR Football | Greenwich | Away - Cardinal Stadium [Directions] | 3:00 p.m. | ED 1:15 | |
| Thu., 11/28 | V Football | Greenwich | Home - Staples Stadium [Directions] | 10:00 a.m. | L 7-27 | |
| Sat., 11/30 | V Girls Basketball | Westhill (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Mon., 12/2 | V Girls Basketball | Kolbe Cathedral (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/2 | JV Girls Basketball | Kolbe Cathedral (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/3 | V Girls Basketball | Masuk (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/3 | JV Girls Basketball | Masuk (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/4 | V Boys Ice Hockey | Norwalk (Scrim.) | Home - Milford Ice Pavilion [Directions] | 7:30 p.m. | ||
| Fri., 12/6 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 5:30 p.m. | ||
| Fri., 12/6 | V Boys Ice Hockey | JBWA (Scrim.) | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | ||
| Fri., 12/6 | V Girls Basketball | Hillhouse (Scrim.) | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/6 | JV Girls Basketball | Hillhouse (Scrim.) | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Sat., 12/7 | V Boys Ice Hockey | Taconic (MA) (Scrim.) | Away | 6:30 p.m. | Pittsfield Boys and Girls Club Rink | |
| Sat., 12/7 | V Girls Ice Hockey | Tournament Game - Opponent Not Known (Scrim.) | Home - Shelton Ice Rink [Directions] | 5:30 p.m. | ||
| Sat., 12/7 | V Girls Ice Hockey | Tournament Game - Opponent Not Known (Scrim.) | Home - Terry Conners Ice Rink [Directions] | 5:30 p.m. | ||
| Sun., 12/8 | V Boys Ice Hockey | Wahconah HS | Away | 12:00 p.m. | North Adams Skating Rink | |
| Wed., 12/11 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 4:15 p.m. | ||
| Wed., 12/11 | FR Girls Basketball | Darien | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/11 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home [Directions] | 6:00 p.m. | Stamford | |
| Wed., 12/11 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home [Directions] | 8:40 p.m. | ||
| Thu., 12/12 | V Boys Basketball | Foran (Scrim.) | Away - Foran High School [Directions] | 6:00 p.m. | ||
| Fri., 12/13 | V Boys Ice Hockey | Norwalk (Scrim.) | Home - Longshore [Directions] | 6:45 p.m. | Longshore Rink | |
| Fri., 12/13 | V Boys Indoor Track | Blue and White Event | Home [Directions] | 2:45 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 3:45 p.m. | L 17-53 | ED 1:45 |
| Fri., 12/13 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 12/13 | V Girls Indoor Track | Blue and White time trials | Home [Directions] | 2:45 p.m. | ||
| Sat., 12/14 | V Boys Basketball | Ansonia (Scrim.) | Away - Ansonia High School [Directions] | 10:00 a.m. | ||
| Sat., 12/14 | V Boys Indoor Track | Blue and White Event | Home [Directions] | 9:00 a.m. | ||
| Sat., 12/14 | V Girls Ice Hockey | Darien | Away [Directions] | 6:00 p.m. | Cancelled | |
| Sat., 12/14 | V Girls Ice Hockey | Darien | Away - Darien Ice Darien Ice Rink [Directions] | 8:10 p.m. | Cancelled | |
| Sat., 12/14 | V Girls Indoor Track | Blue and White time trials | Home [Directions] | 9:00 a.m. | ||
| Wed., 12/18 | V Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 42-38 | |
| Wed., 12/18 | JV Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | ED 1:45 | |
| Wed., 12/18 | V Wrestling | Harding/Bassick/Bridgeport Central | Home - Staples Field House [Directions] | 6:00 p.m. | ||
| Wed., 12/18 | V Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 7:00 p.m. | L 25-51 | |
| Wed., 12/18 | JV Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | ||
| Thu., 12/19 | V Girls Gymnastics | Greenwich, Weston | Away - Greenwich YWCA [Directions] | 6:00 p.m. | 125.65 | |
| Fri., 12/20 | V Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 7:00 p.m. | L 58-62 | |
| Fri., 12/20 | JV Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Girls Basketball | Bassick | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 59-20 | |
| Fri., 12/20 | JV Girls Basketball | Bassick | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Girls Basketball | Trumbull | Home [Directions] | 3:45 p.m. | ||
| Fri., 12/20 | V Girls Ice Hockey | West Haven/SHA | Home - Terry Conners Ice Rink [Directions] | 8:30 p.m. | ||
| Fri., 12/20 | V Girls Ice Hockey | West Haven/SHA | Home - Terry Conners Ice Rink [Directions] | 8:30 p.m. | Stamford | |
| Fri., 12/20 | V Girls Indoor Track | New Haven Invitational | Away | TBA | ED 2:00 | |
| Sat., 12/21 | V Boys Ice Hockey | Norwich Free Academy | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 8-2 [Detailed Results] | |
| Sat., 12/21 | V Boys Indoor Track | FCIAC Qualifier #1 | Home [Directions] | 10:00 a.m. | ||
| Sat., 12/21 | V Wrestling | Fairfield Ludlowe Invitational | Away | 9:30 a.m. | ||
| Sat., 12/21 | V Girls Indoor Track | FCIAC Qualifier #1 | Home [Directions] | 10:00 a.m. | ||
| Mon., 12/23 | V Boys Ice Hockey | New Fairfield | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 4-7 [Detailed Results] | |
| Thu., 12/26 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | 4:00 p.m. | L 0-8 | |
| Fri., 12/27 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:00 p.m. | L 59-65 | |
| Fri., 12/27 | V Boys Indoor Track | Hillhouse Winter Relays | Away | 10:00 a.m. | ||
| Fri., 12/27 | V Wrestling | Westhill | Away - Westhill - New Gymnasium [Directions] | 11:00 a.m. | ||
| Fri., 12/27 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 1:00 p.m. | L 41-46 | |
| Fri., 12/27 | JV Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/28 | JV Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/28 | V Girls Indoor Track | Rhode Island Classic | Away | 2:00 p.m. | ||
| Mon., 12/30 | V Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | W 50-43 | |
| Mon., 12/30 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 1:00 p.m. | W 45-39 | |
| Mon., 12/30 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Wonderland of Ice [Directions] | 9:30 a.m. | ||
| Mon., 12/30 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Wonderland of Ice [Directions] | TBA | Stamford | |
| Wed., 1/1 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks [Directions] | 3:50 p.m. | L 2-3 | Ellington Ct |
| Sat., 1/4 | V Boys Ice Hockey | Norwich Free Academy | Away - Norwich Ice Rink [Directions] | 7:00 p.m. | W 8-4 | |
| Sat., 1/4 | V Boys Indoor Track | FCIAC Qualifier #2 | Home [Directions] | 10:00 a.m. | ||
| Sat., 1/4 | V Boys Indoor Track | Hartford Invitational | Away | TBA | Cancelled | |
| Sat., 1/4 | V Wrestling | Bunnell Duals | Away | 10:00 a.m. | ||
| Sat., 1/4 | V Girls Gymnastics | Pomperaug Invitational | Away | TBA | 126.30 | |
| Sat., 1/4 | V Girls Ice Hockey | Greenwich | Home [Directions] | 6:00 p.m. | ||
| Sat., 1/4 | V Girls Ice Hockey | Greenwich | Home [Directions] | 8:40 p.m. | ||
| Sat., 1/4 | V Girls Indoor Track | FCIAC Qualifier #2 | Home [Directions] | 10:00 a.m. | ||
| Mon., 1/6 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Mon., 1/6 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | 6:00 p.m. | 124.55 | |
| Tue., 1/7 | V Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | L 36-66 | |
| Tue., 1/7 | JV Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/7 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | L 32-73 | |
| Tue., 1/7 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/7 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/8 | V Boys Alpine Skiing | Fairfield, Cheshire, Litchfield, Farmington, Amity | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 1/8 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | W 7-4 | |
| Wed., 1/8 | V Boys Swimming and Diving | Wilton | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/8 | V Wrestling | Danbury | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/8 | V Girls Alpine Skiing | Farifield, Cheshire, Litchfield, Amity | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 1/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Norwalk Ice House [Directions] | 5:45 p.m. | ||
| Wed., 1/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away [Directions] | 6:00 p.m. | ||
| Thu., 1/9 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 37-60 | |
| Thu., 1/9 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Thu., 1/9 | V Girls Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 6:15 p.m. | W 46-30 | |
| Thu., 1/9 | JV Girls Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/9 | V Girls Gymnastics | New Milford | Away - New Milford High School [Directions] | 5:00 p.m. | 127.05 | |
| Fri., 1/10 | V Boys Basketball | Wilton | Away - Wilton Field House [Directions] | 7:00 p.m. | L 50-60 | |
| Fri., 1/10 | JV Boys Basketball | Wilton | Away - Wilton Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/10 | V Boys Swimming and Diving | Danbury | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/10 | V Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 23-55 | |
| Fri., 1/10 | JV Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/11 | V Boys Ice Hockey | Stamford | Away - Terry Conners Ice Rink [Directions] | 3:10 p.m. | W 6-2 | |
| Sat., 1/11 | V Boys Indoor Track | FCIAC Qualifier #3 | Home [Directions] | 10:00 a.m. | ||
| Sat., 1/11 | V Boys Indoor Track | SCC Coaches Invitational @ Hillhouse | Away | 9:00 a.m. | ||
| Sat., 1/11 | V Wrestling | Ellis Tech | Home - Staples H.S. Gym [Directions] | 9:30 a.m. | Cancelled | |
| Sat., 1/11 | V Girls Ice Hockey | New Canaan | Away [Directions] | 6:00 p.m. | ||
| Sat., 1/11 | V Girls Ice Hockey | New Canaan | Away - Darien Rink [Directions] | 7:40 p.m. | ||
| Sat., 1/11 | V Girls Indoor Track | FCIAC Qualifier #3 | Home [Directions] | 10:00 a.m. | ||
| Sat., 1/11 | V Girls Indoor Track | SCC Coaches Invitational @ Hillhouse | Away | 9:00 a.m. | ||
| Mon., 1/13 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 3:30 p.m. | ||
| Tue., 1/14 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | L 50-63 | |
| Tue., 1/14 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Tue., 1/14 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Tue., 1/14 | V Girls Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 47-36 | |
| Tue., 1/14 | JV Girls Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | FR Girls Basketball | Fairfield Ludlowe | Home - Staples Field House [Directions] | 3:45 p.m. | ||
| Tue., 1/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Home [Directions] | 8:20 p.m. | ||
| Wed., 1/15 | V Boys Ice Hockey | Greenwich | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | W 4-3 | |
| Wed., 1/15 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee, Fairfield Warde | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/15 | V Wrestling | Greenwich | Away - GHS Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 1/15 | V Girls Gymnastics | New Canaan, Westhill | Away - Westhill [Directions] | 5:30 p.m. | 125.75 | |
| Wed., 1/15 | V Girls Ice Hockey | Trumbull/St. Joseph | Home [Directions] | 6:00 p.m. | Stamford | |
| Fri., 1/17 | V Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 63-48 | |
| Fri., 1/17 | JV Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Boys Indoor Track | Yale Invitational | Away | 1:00 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:30 p.m. | ED 1:30 | |
| Fri., 1/17 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 29-49 | |
| Fri., 1/17 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/17 | V Girls Indoor Track | Yale Classic | Away | 1:00 p.m. | ||
| Sat., 1/18 | V Boys Ice Hockey | Ridgefield | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 5-7 | |
| Sat., 1/18 | V Boys Indoor Track | FCIAC Qualifier #4 | Home [Directions] | 10:00 a.m. | ||
| Sat., 1/18 | V Boys Indoor Track | Yale Invitational | Away | 9:00 a.m. | ||
| Sat., 1/18 | V Wrestling | New Canaan, Bunnell, Brien McMahon | Home - Staples H.S. Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/18 | V Girls Ice Hockey | Fairfield Warde | Away - Wonderland of Ice [Directions] | 1:00 p.m. | Stamford | |
| Sat., 1/18 | V Girls Ice Hockey | Fairfield Warde | Away - Wonderland of Ice [Directions] | 1:00 p.m. | ||
| Sat., 1/18 | V Girls Indoor Track | FCIAC Qualifier #4 | Home [Directions] | 10:00 a.m. | ||
| Sat., 1/18 | V Girls Indoor Track | Yale Classic | Away | 9:00 a.m. | ||
| Mon., 1/20 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 2:00 p.m. | 132.8 | |
| Mon., 1/20 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven High School [Directions] | 10:00 a.m. | ||
| Tue., 1/21 | FR Girls Basketball | Harding | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 1/22 | V Competitive Cheerleading | All FCIAC Competition | Away | 5:00 p.m. | ||
| Wed., 1/22 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 6:00 p.m. | Stamford | |
| Thu., 1/23 | V Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 7:00 p.m. | L 62-79 | |
| Thu., 1/23 | JV Boys Basketball | Harding | Away [Directions] | 5:15 p.m. | ||
| Thu., 1/23 | FR Boys Basketball | Harding | Away [Directions] | 4:00 p.m. | ||
| Thu., 1/23 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 1/24 | V Boys Swimming and Diving | Greenwich | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Sat., 1/25 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 7:15 p.m. | L 3-5 | |
| Sat., 1/25 | V Boys Indoor Track | FCIAC Western Division Championship | Home [Directions] | 2:00 p.m. | ||
| Sat., 1/25 | V Wrestling | Weston, Fairfield Prep, Brien McMahon | Home [Directions] | 9:00 a.m. | ||
| Sat., 1/25 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics [Directions] | 5:00 p.m. | 126.4 | |
| Sat., 1/25 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 1:30 p.m. | ||
| Sat., 1/25 | V Girls Ice Hockey | Darien | Home [Directions] | 6:00 p.m. | ||
| Sat., 1/25 | V Girls Indoor Track | Western Divisional Championship | Home [Directions] | 2:00 p.m. | ||
| Mon., 1/27 | V Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 39-45 | |
| Mon., 1/27 | JV Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/27 | FR Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Boys Alpine Skiing | Greenwich, Weston, Pomperaug, Darien | Away | 4:00 p.m. | ED 1:45 | |
| Tue., 1/28 | V Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 39-65 | |
| Tue., 1/28 | JV Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Girls Alpine Skiing | Greenwich, Weston, Pomperaug, Darien | Away | 4:00 p.m. | ED 1:45 | |
| Tue., 1/28 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 18-40 | |
| Tue., 1/28 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/29 | V Boys Alpine Skiing | Wilton, Glastonbury, Southington, Hand, Ridgefield | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 1/29 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | 8:00 p.m. | W 7-1 | |
| Wed., 1/29 | V Boys Indoor Track | FCIAC Championship | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 1/29 | V Boys Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/29 | V Wrestling | Stamford | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/29 | V Girls Alpine Skiing | Wilton, Glastonbury, Southington, Hand, Ridgefield | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 1/29 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | L 32-53 | |
| Wed., 1/29 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/29 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners Ice Rink [Directions] | 4:50 p.m. | ||
| Wed., 1/29 | V Girls Indoor Track | FCIAC Championship @ Hillhouse | Away | 4:00 p.m. | ED 1:45 | |
| Thu., 1/30 | V Girls Gymnastics | Wilton | Away - Wilton High School Aux. Gym [Directions] | 4:00 p.m. | 127.35 | |
| Thu., 1/30 | V Girls Ice Hockey | Masuk Coop | Away - Shelton High School [Directions] | 5:30 p.m. | ||
| Fri., 1/31 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | L 40-46 | |
| Fri., 1/31 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 44-35 | |
| Fri., 1/31 | JV Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/1 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 6:00 p.m. | T 4-4 (OT) | |
| Sat., 2/1 | V Boys Indoor Track | FCIAC JV Invitational | Home [Directions] | 10:00 a.m. | ||
| Sat., 2/1 | V Wrestling | Norwich Free Academy, Fairfield Prep | Home - Staples H.S. Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/1 | V Girls Gymnastics | Darien, New Milford | Away - DARIEN YMCA [Directions] | 2:00 p.m. | 127.95 | |
| Sat., 2/1 | V Girls Ice Hockey | Greenwich | Away [Directions] | 8:00 p.m. | stop to pick up Stamford team | |
| Tue., 2/4 | V Boys Basketball | Stamford | Away - Stamford High School [Directions] | 7:00 p.m. | L 60-77 | |
| Tue., 2/4 | JV Boys Basketball | Stamford | Away - Stamford High School [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Boys Basketball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 3:20 p.m. | W 5-4 (OT) | ED 12:45 Start at Shelton HS at 12:15, go to pick up rest of team at Staples, then head to Danbury Ice Arena. |
| Tue., 2/4 | V Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 28-41 | |
| Tue., 2/4 | JV Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 8:20 p.m. | ||
| Wed., 2/5 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home [Directions] | 6:00 p.m. | ||
| Thu., 2/6 | V Wrestling | Darien | Away - DHS - South Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | V Girls Ice Hockey | New Canaan | Home [Directions] | 8:40 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 42-49 | |
| Fri., 2/7 | JV Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Boys Swimming and Diving | Darien | Away [Directions] | 3:00 p.m. | ED 1:15 | |
| Fri., 2/7 | V Wrestling | Fairfield Warde, Norwalk, Bridgeport Central, Fitch | Away [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | L 30-40 | |
| Fri., 2/7 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/8 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 1-2 | |
| Sat., 2/8 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | ||
| Sat., 2/8 | V Wrestling | Fairfield Warde, Bridgeport Central, Norwalk | Away [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 2/8 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics [Directions] | 6:00 p.m. | 125.3 | |
| Sat., 2/8 | V Girls Ice Hockey | New Canaan | Home [Directions] | 6:00 p.m. | ||
| Sat., 2/8 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | ||
| Mon., 2/10 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 8:40 p.m. | L 0-6 | |
| Mon., 2/10 | V Boys Swimming and Diving | Trumbull | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/10 | V Wrestling | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Mon., 2/10 | V Girls Basketball | Harding | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 46-32 | |
| Mon., 2/10 | JV Girls Basketball | Harding | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/10 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 8:30 p.m. | ||
| Tue., 2/11 | V Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 7:00 p.m. | L 53-78 | |
| Tue., 2/11 | JV Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | FR Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Tue., 2/11 | V Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 33-43 | |
| Tue., 2/11 | JV Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | FR Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/12 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 4-5 (OT) | |
| Wed., 2/12 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ED 1:15 | |
| Wed., 2/12 | V Wrestling | Trumbull | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/12 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Terry Conners Ice Rink [Directions] | 3:40 p.m. | ||
| Wed., 2/12 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 6:00 p.m. | ||
| Fri., 2/14 | FR Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 2/14 | V Wrestling | FCIAC Trials @ New Canaan | Away | 4:30 p.m. | ||
| Sat., 2/15 | V Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 1:00 p.m. | L 67-88 | |
| Sat., 2/15 | JV Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/15 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/15 | V Wrestling | FCIAC Wrestlebacks @ New Canaan | Away | 10:00 a.m. | ||
| Sat., 2/15 | V Wrestling | FCIAC Finals @ New Canaan | Away | 4:00 p.m. | ||
| Sat., 2/15 | V Girls Gymnastics | FCIAC Championship @ Westhill | Away | 10:30 a.m. | 126.20 | |
| Sat., 2/15 | V Girls Ice Hockey | Fairfield Warde | Home - Terry Conners Ice Rink [Directions] | 3:10 p.m. | ||
| Sat., 2/15 | V Girls Ice Hockey | Fairfield Warde | Home [Directions] | 6:00 p.m. | Stamford | |
| Sat., 2/15 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sun., 2/16 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 1:45 p.m. | W 52-46 | |
| Sun., 2/16 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 12:00 p.m. | ||
| Mon., 2/17 | V Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 72-66 | |
| Mon., 2/17 | JV Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/17 | FR Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/17 | V Boys Ice Hockey | Tri-Town | Home - Milford Ice Pavilion [Directions] | 4:30 p.m. | W 6-1 | |
| Mon., 2/17 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 12:30 p.m. | L 45-53 | |
| Mon., 2/17 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 11:00 a.m. | ||
| Tue., 2/18 | FR Girls Basketball | New Canaan | Home - Staples Field House [Directions] | 11:00 a.m. | Cancelled | |
| Tue., 2/18 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 2:20 p.m. | ||
| Tue., 2/18 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 2:20 p.m. | ||
| Wed., 2/19 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 37-75 | |
| Wed., 2/19 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/19 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 6:00 p.m. | L 2-6 | |
| Wed., 2/19 | V Girls Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 34-46 | |
| Wed., 2/19 | JV Girls Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | FR Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Thu., 2/20 | FR Girls Basketball | Pomperaug | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/21 | V Wrestling | CIAC Class LL Championship | Away | 4:30 p.m. | ||
| Fri., 2/21 | V Girls Gymnastics | Newtown, Trumbull | Away [Directions] | 7:00 p.m. | Cancelled | |
| Sat., 2/22 | V Boys Swimming and Diving | JV FCIACS @ Greenwich HS | Away | 1:30 p.m. | ||
| Sat., 2/22 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:15 a.m. | ||
| Mon., 2/24 | V Boys Alpine Skiing | Prep, Laurelton Hall, New Canaan, Southington | Away | 4:00 p.m. | ED 1:45 | |
| Mon., 2/24 | V Boys Ice Hockey | Daniel Hand | Home - Milford Ice Pavilion [Directions] | 4:20 p.m. | L 3-7 | |
| Mon., 2/24 | V Girls Alpine Skiing | Prep, Laurelton Hall, New Canaan, Southington | Away | 4:00 p.m. | ED 1:45 | |
| Tue., 2/25 | V Boys Swimming and Diving | FCIAC Trials | Away | 4:30 p.m. | ED 1:45 | |
| Wed., 2/26 | V Boys Alpine Skiing | Barlow, Danbury, Guilford, Berlin, Weston | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 2/26 | V Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 54-41 | |
| Wed., 2/26 | JV Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/26 | FR Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/26 | V Boys Ice Hockey | Trinity Catholic | Home - Milford Ice Pavilion [Directions] | 4:00 p.m. | L 1-2 | ED 1:30 |
| Wed., 2/26 | V Boys Swimming and Diving | FCIAC Diving Finals @ Westhill HS | Away | 4:30 p.m. | ||
| Wed., 2/26 | V Girls Alpine Skiing | Barlow, Danbury, Guilford, Berlin, Weston | Away | 4:00 p.m. | ED 1:45 | |
| Wed., 2/26 | V Girls Ice Hockey | Greenwich | Away [Directions] | 6:30 p.m. | pick up Stamford near tennis courts | |
| Wed., 2/26 | V Girls Ice Hockey | Greenwich | Away [Directions] | 6:45 p.m. | ||
| Thu., 2/27 | V Boys Swimming and Diving | FCIAC Swimming Finals @ Greenwich HS | Away | 6:30 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 3/1 | V Boys Ice Hockey | Darien | Away [Directions] | 4:20 p.m. | ||
| Sat., 3/1 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Sat., 3/1 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:15 a.m. | ||
| Sat., 3/1 | V Competitive Cheerleading | @ Danbury HS | Away | 2:00 p.m. | ||
| Sat., 3/1 | V Girls Gymnastics | States | Away | 4:00 p.m. | Pomperaug HS | |
| Sat., 3/1 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Wed., 3/5 | V Boys Alpine Skiing | States | Away | 4:00 p.m. | ED 12:45 | |
| Wed., 3/5 | V Girls Alpine Skiing | States | Away | 4:00 p.m. | ED 12:45 | |
| Fri., 3/7 | V Wrestling | New England Championships | Away - Providence Career and Technical Center | 4:30 p.m. | ||
| Sat., 3/8 | V Wrestling | New England Championships | Away - Providence Career and Technical Center | 9:15 a.m. | ||
| Sat., 3/8 | V Competitive Cheerleading | States | Away | TBA | ||
| Mon., 3/10 | V Boys Ice Hockey | State Tournament | Home - Milford Ice Pavilion [Directions] | 7:30 p.m. | ||
| Wed., 3/12 | V Boys Swimming and Diving | Class LL Diving @ Hamden HS | Away | 5:30 p.m. | ||
| Thu., 3/13 | Unified Sports Basketball | Unified Sports | Away | 3:00 p.m. | 2 Wheelchairs | |
| Sat., 3/15 | V Boys Rugby | Clinic @ Ludlowe | Away | 11:00 a.m. | ||
| Sat., 3/15 | V Boys Swimming and Diving | Class LL Trials @ Hamden HS | Away | 3:30 p.m. | ||
| Wed., 3/19 | V Boys Swimming and Diving | Class Ll Finals | Away | 3:00 p.m. | ||
| Thu., 3/20 | V Boys Swimming and Diving | State Open Diving | Away | 5:30 p.m. | ||
| Sat., 3/22 | V Boys Rugby | Belmont | Home - Staples Stadium [Directions] | 11:00 a.m. | ||
| Sat., 3/22 | V Boys Swimming and Diving | State Opens | Away | 2:30 p.m. | ||
| Sat., 3/22 | V Competitive Cheerleading | New England Championship | Away | 2:30 p.m. | ||
| Sat., 3/22 | V Competitive Cheerleading | New England Championship | Away | 2:30 p.m. | ||
| Thu., 3/27 | V Girls Lacrosse | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 3:30 p.m. | ||
| Fri., 3/28 | V Softball | Brien McMahon (Scrim.) | Away - Brien McMahon HS [Directions] | 8:00 p.m. | InSports center | |
| Sat., 3/29 | V Baseball | Seymour (Scrim.) | Home - Staples HS Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 3/29 | V Boys Lacrosse | Branford, New Milford | Home - Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 3/29 | V Girls Lacrosse | Daniel Hand (Scrim.) | Away [Directions] | 1:10 p.m. | ||
| Tue., 4/1 | V Baseball | Fairfield Warde (Scrim.) | Home - Staples Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 4/1 | JV Baseball | Fairfield Warde (Scrim.) | Home - Wakeman Field [Directions] | 3:30 p.m. | ||
| Tue., 4/1 | V Softball | Shelton (Scrim.) | Away - Shelton High School Softball Field [Directions] | 3:45 p.m. | ED 2:00 | |
| Tue., 4/1 | JV Softball | Shelton (Scrim.) | Away - Shelton High School Softball Field [Directions] | 3:45 p.m. | ride with varsity | |
| Wed., 4/2 | V Baseball | Amity (Scrim.) | Away - John Janenda Baseball Field @ Amity HS [Directions] | 3:45 p.m. | ||
| Wed., 4/2 | V Boys Lacrosse | New Canaan (Scrim.) | Away - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/2 | JV Boys Lacrosse | Joel Barlow (Scrim.) | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/2 | V Co-ed Sailing | Grass Island | Away | TBA | ||
| Wed., 4/2 | V Girls Lacrosse | Loomis Chaffee School (Scrim.) | Away | 4:30 p.m. | ||
| Wed., 4/2 | V Softball | Greenwich (Scrim.) | Home - Greens Farms Elementary School [Directions] | 3:45 p.m. | ||
| Wed., 4/2 | V Girls Water Polo | Greenwich | Away [Directions] | 3:30 p.m. | ED 1:25 | |
| Thu., 4/3 | V Baseball | Bunnell (Scrim.) | Away - Bunnell Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/3 | JV Baseball | Bunnell (Scrim.) | Away - Flood M.S. [Directions] | 4:00 p.m. | ||
| Thu., 4/3 | V Boys Rugby | Darien | Away [Directions] | 4:00 p.m. | A & B | |
| Fri., 4/4 | V Baseball | Trumbull (Scrim.) | Away - Varsity Baseball Field [Directions] | 3:30 p.m. | Cancelled | |
| Fri., 4/4 | JV Baseball | Trumbull (Scrim.) | Away - JV Baseball Field [Directions] | 3:30 p.m. | Cancelled | |
| Fri., 4/4 | V Softball | Bethel (Scrim.) | Away - TBA [Directions] | 3:45 p.m. | ||
| Fri., 4/4 | JV Softball | Bethel (Scrim.) | Away - Berry School Field [Directions] | 3:45 p.m. | ride with varsity | |
| Fri., 4/4 | V Girls Tennis | Greens Farms Academy (Scrim.) | Away | 4:00 p.m. | ||
| Sat., 4/5 | V Boys Lacrosse | Darien (Scrim.) | Away - DHS Stadium Field [Directions] | 9:00 a.m. | ||
| Sat., 4/5 | JV Boys Lacrosse | Darien (Scrim.) | Away - DHS Turf #2 [Directions] | 9:00 a.m. | ||
| Sat., 4/5 | V Boys Volleyball | Fairfield Ludlowe Play Day | Away | 9:00 a.m. | ||
| Sat., 4/5 | V Softball | Berlin Round Robin Invitational | Away | 9:00 a.m. | ||
| Sat., 4/5 | V Girls Water Polo | Choate Rosemary Hall | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Mon., 4/7 | V Softball | Fairfield Ludlowe (Scrim.) | Home - Wakeman Field C [Directions] | 3:45 p.m. | ||
| Mon., 4/7 | JV Softball | Fairfield Ludlowe (Scrim.) | Home - Staples HS - Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/8 | JV Boys Golf | Darien | Away - CC of Darien [Directions] | 3:15 p.m. | ED 1:50 | |
| Tue., 4/8 | JV Boys Tennis | St. Lukes (Scrim.) | Away | 4:00 p.m. | ||
| Tue., 4/8 | JV Girls Golf | @ Par 3 | Away | TBA | ||
| Tue., 4/8 | V Girls Lacrosse | Hall (Scrim.) | Away - Hall HS Stadium (Turf Field) [Directions] | 4:30 p.m. | ||
| Wed., 4/9 | V Boys Lacrosse | Weston | Away - WHS Turf Field [Directions] | 6:00 p.m. | W 12 - 4 | |
| Wed., 4/9 | JV Boys Lacrosse | Weston | Away - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Boys Tennis | Darien | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/9 | JV Boys Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Co-ed Sailing | Indian Harbor Yacht Club | Away | TBA | ED 1:50 | |
| Wed., 4/9 | JV Girls Golf | Trumbull | Away - The Glen at Tashua Knolls [Directions] | 3:15 p.m. | ||
| Wed., 4/9 | V Girls Outdoor Track | Greenwich | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 4/9 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | FR Boys Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 4/10 | V Boys Outdoor Track | Greenwich | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | V Boys Rugby | Fairfield Prep | Home - PJ Romano Field - Saugatuck Elem School [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | V Boys Tennis | Westhill | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 4/10 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 4:00 p.m. | W 16-00 (5) | ED 2:00 |
| Thu., 4/10 | JV Softball | New Fairfield | Away - NFHS Cashman Field [Directions] | 4:00 p.m. | ride with varsity | |
| Thu., 4/10 | V Girls Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/11 | V Baseball | Danbury | Home - Staples Baseball Field [Directions] | 4:00 p.m. | W 12-3 | |
| Fri., 4/11 | JV Baseball | Danbury | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | FR Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Fri., 4/11 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 4/11 | V Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 14-12 | |
| Fri., 4/11 | JV Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Fri., 4/11 | FR Girls Lacrosse | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | V Softball | Danbury | Away - Danbury High Varsity Softball Field [Directions] | 4:00 p.m. | L 02-11 | ED 1:45 |
| Fri., 4/11 | JV Softball | Danbury | Away - Danbury High School Junior Varsity Softball Field [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 4/11 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Sat., 4/12 | V Baseball | Masuk | Home - Staples HS Baseball Field [Directions] | 3:00 p.m. | L 3-4 | |
| Sat., 4/12 | V Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 6:30 p.m. | W 11 - 2 | |
| Sat., 4/12 | JV Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 5:00 p.m. | ||
| Sat., 4/12 | V Boys Volleyball | Rhode Island Tournament @ North Kingstown High School | Away | 9:00 a.m. | 150 Fairway Dr, North Kingstown, RI | |
| Sat., 4/12 | V Girls Outdoor Track | Hammonasset Freshmen Invitational | Away | 9:00 a.m. | ||
| Sat., 4/12 | V Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Mon., 4/14 | V Baseball | Bassick | Away [Directions] | 3:00 p.m. | W 19-0 | |
| Mon., 4/14 | JV Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 3:00 p.m. | ||
| Mon., 4/14 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | 3:00 p.m. | W 7-0 | |
| Mon., 4/14 | V Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 3:00 p.m. | W 3-0 | |
| Mon., 4/14 | V Girls Tennis | Trinity Catholic | Home - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | W 7-0 | |
| Tue., 4/15 | V Boys Lacrosse | Fairfield Warde | Home - Staples Stadium [Directions] | 1:00 p.m. | W 9 - 1 | |
| Tue., 4/15 | JV Boys Lacrosse | Fairfield Warde | Home - Staples Stadium [Directions] | 11:00 a.m. | ||
| Tue., 4/15 | FR Boys Lacrosse | Danbury | Home - Wakeman Field B (turf) [Directions] | 11:00 a.m. | ||
| Tue., 4/15 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 18-1 | |
| Tue., 4/15 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 4/16 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 9-6(9) | |
| Wed., 4/16 | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 4/16 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 11:00 a.m. | W 7-0 | |
| Wed., 4/16 | JV Boys Tennis | St. Lukes | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 4/16 | V Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Wed., 4/16 | JV Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 12:30 p.m. | ||
| Wed., 4/16 | V Softball | Brien McMahon | Home - Greens Farms Elementary School [Directions] | 6:00 p.m. | W 06-02 | |
| Wed., 4/16 | JV Softball | Brien McMahon | Home - Staples HS - Softball Field [Directions] | 10:30 a.m. | ||
| Thu., 4/17 | V Baseball | Greenwich | Home - Staples Baseball Field [Directions] | 1:00 p.m. | W 2-1(9) | |
| Thu., 4/17 | JV Baseball | Greenwich | Home - Wakeman Field [Directions] | 1:00 p.m. | ||
| Thu., 4/17 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 10:00 a.m.. | ||
| Thu., 4/17 | V Boys Lacrosse | St. John The Baptist (NY) | Home - Staples Stadium [Directions] | 12:30 p.m. | W 9 to 7 | |
| Thu., 4/17 | JV Boys Lacrosse | St. John The Baptist (NY) | Home - Wakeman Field B (turf) [Directions] | 12:30 p.m. | ||
| Thu., 4/17 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Thu., 4/17 | V Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 10:45 a.m. | W 14-8 | |
| Thu., 4/17 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 12:15 p.m. | ||
| Thu., 4/17 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | 4:00 p.m. | L 05-14 | |
| Thu., 4/17 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | Cancelled | ride with varsity |
| Sat., 4/19 | V Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | 12:00 p.m. | W 7-2 | |
| Sat., 4/19 | V Boys Lacrosse | Norwalk | Home - Staples Stadium [Directions] | 1:00 p.m. | W 14 - 8 | |
| Sat., 4/19 | JV Boys Lacrosse | Norwalk | Home - Staples Stadium [Directions] | 3:00 p.m. | ||
| Sat., 4/19 | V Girls Lacrosse | Glastonbury | Away - GHS Field #12 [Directions] | 10:00 a.m. | L 13-9 | |
| Sat., 4/19 | JV Girls Lacrosse | Glastonbury | Away - GHS Field #12 [Directions] | 11:15 a.m. | ||
| Sat., 4/19 | V Girls Outdoor Track | Bloomfield Relays | Away | 10:00 a.m. | ||
| Mon., 4/21 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 2-3 | |
| Mon., 4/21 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/21 | FR Baseball | Wilton | Home - Staples HS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/21 | V Boys Golf | Bassick, Bridgeport Central, Harding | Away - Fairchild-Wheeler [Directions] | 3:15 p.m. | 156 | ED 2:00 |
| Mon., 4/21 | FR Boys Lacrosse | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/21 | JV Boys Tennis | Fairfield Ludlowe | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | JV Girls Golf | Greenwich | Away - TBA [Directions] | TBA | Cancelled | |
| Mon., 4/21 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Girls Outdoor Track | Brien McMahon, Bridgeport Central | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Softball | Wilton | Home - Wakeman Field C [Directions] | 4:00 p.m. | W 08-04 | |
| Mon., 4/21 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 4/22 | JV Boys Golf | Fairfield Warde | Home - Longshore [Directions] | 3:15 p.m. | ||
| Tue., 4/22 | V Boys Lacrosse | Greenwich | Home - Wakeman Field B (turf) [Directions] | 4:45 p.m. | L 3-5 | |
| Tue., 4/22 | JV Boys Lacrosse | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Outdoor Track | Brien McMahon, Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Tennis | Stamford | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/22 | JV Boys Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Girls Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | Ridgefield. 217. Staples 169 | ED 2:00pm |
| Tue., 4/22 | JV Girls Golf | Newtown | Away [Directions] | 3:00 p.m. | Cancelled | Rock Ridge Country Club |
| Tue., 4/22 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS Upper Grass Field [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 4/22 | V Softball | Bassick | Home - Wakeman Field C [Directions] | 4:00 p.m. | W 19-00 (5) | |
| Tue., 4/22 | V Girls Tennis | Stamford | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-0 | |
| Tue., 4/22 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Girls Water Polo | Chelsea Piers | Away | 6:00 p.m. | ||
| Wed., 4/23 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:00 p.m. | W 14-1 | |
| Wed., 4/23 | JV Baseball | Trinity Catholic | Away - Barrett Field @ Belltown Park | 4:00 p.m. | ||
| Wed., 4/23 | FR Baseball | Trinity Catholic | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | 3:15 p.m. | 160 | ED 2:00 |
| Wed., 4/23 | JV Boys Golf | Darien | Home - Longshore [Directions] | 3:15 p.m. | ||
| Wed., 4/23 | FR Boys Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/23 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 4/23 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 4/23 | JV Girls Golf | Trumbull | Away - The Glen at Tashua Knolls [Directions] | 3:15 p.m. | ||
| Wed., 4/23 | FR Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Wed., 4/23 | V Softball | Trinity Catholic | Home - Wakeman Field [Directions] | 4:00 p.m. | L 05-06 | |
| Wed., 4/23 | V Girls Tennis | Brien McMahon | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/24 | V Boys Golf | Westhill | Home - Longshore [Directions] | 3:00 p.m. | 162 | |
| Thu., 4/24 | JV Boys Golf | Fairfield Prep | Home - Longshore [Directions] | 3:15 p.m. | ||
| Thu., 4/24 | V Boys Lacrosse | Fox Lane (NY) | Home - Staples Stadium [Directions] | 5:30 p.m. | L 8 - 11 | |
| Thu., 4/24 | JV Boys Lacrosse | Fox Lane (NY) | Home - Wakeman Field B (turf) [Directions] | TBA | Cancelled | |
| Thu., 4/24 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 3:45 p.m. | ||
| Thu., 4/24 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Danbury. 194. Staples. 191 | ED 1:45 |
| Thu., 4/24 | V Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 6-9 | |
| Thu., 4/24 | JV Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | Cancelled | |
| Thu., 4/24 | V Girls Outdoor Track | Penn Relays | Away | TBA | ||
| Thu., 4/24 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | V Girls Water Polo | Greenwich | Away [Directions] | 3:30 p.m. | ED 1:30 | |
| Fri., 4/25 | V Baseball | Fairfield Warde | Home - Staples Baseball Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 4/25 | JV Baseball | Fairfield Warde | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away | 4:00 p.m. | ED 1:15 | |
| Fri., 4/25 | V Boys Tennis | Weston | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/25 | V Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 3-1 | |
| Fri., 4/25 | JV Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | ||
| Fri., 4/25 | V Co-ed Sailing | Pequot Yacht Club | Home [Directions] | 3:00 p.m. | ||
| Fri., 4/25 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | L 00-01 (8) | |
| Fri., 4/25 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | ride with varsity | |
| Sat., 4/26 | V Boys Lacrosse | Trumbull | Home - Staples Stadium [Directions] | 1:00 p.m. | W 12-5 | Sticks for Soldiers |
| Sat., 4/26 | JV Boys Lacrosse | Trumbull | Home - Staples Stadium [Directions] | 3:00 p.m. | ||
| Sat., 4/26 | FR Boys Lacrosse | St. Anthonys (NY) | Home - Staples Stadium [Directions] | 9:30 a.m. | ||
| Sat., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | ||
| Sat., 4/26 | V Co-ed Sailing | US Coast Guard Academy | Away | TBA | ||
| Sat., 4/26 | JV Girls Lacrosse | Loomis Chaffee School | Away | 11:00 a.m. | Cancelled | |
| Sat., 4/26 | FR Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 2:30 p.m. | ||
| Sat., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away | TBA | ||
| Sat., 4/26 | V Girls Water Polo | Williston and Suffield @ Suffield | Away | 12:45 p.m. | AT Bus | |
| Mon., 4/28 | V Baseball | Harding | Away - Beardsley Park - Baseball [Directions] | 4:00 p.m. | W 18-0 | |
| Mon., 4/28 | JV Baseball | Harding | Away - Seaside Park [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Boys Golf | Fairfield Ludlowe | Home - Longshore [Directions] | 3:00 p.m. | 156 | |
| Mon., 4/28 | V Boys Rugby | West Hartford Rugby | Away | 6:00 p.m. | ||
| Mon., 4/28 | V Boys Tennis | New Canaan | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/28 | JV Boys Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Ludlowe H.S. [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/28 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Ludlowe H.S. [Directions] | 5:30 p.m. | ride with varsity | |
| Mon., 4/28 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:30 p.m. | Warde 202. Staples. 180 | |
| Mon., 4/28 | JV Girls Golf | Fairfield Ludlowe | Home - Longshore [Directions] | TBA | ||
| Mon., 4/28 | FR Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Mon., 4/28 | V Girls Outdoor Track | Bassick, Danbury | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Softball | Harding | Home - Wakeman Field C [Directions] | 4:00 p.m. | W 18-00 (5) | |
| Mon., 4/28 | JV Softball | Harding | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/29 | V Boys Golf | Trinity Catholic, New Canaan | Away - Sterling Farms | 3:15 p.m. | 168 | |
| Tue., 4/29 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:15 p.m. | Smith Richardson | |
| Tue., 4/29 | V Boys Lacrosse | Ridgefield | Home - Staples Stadium [Directions] | 5:30 p.m. | L 0 - 11 | |
| Tue., 4/29 | JV Boys Lacrosse | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | V Boys Outdoor Track | Danbury, Bassick | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | ED 1:15 | |
| Tue., 4/29 | V Boys Tennis | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | W 5-1 | |
| Tue., 4/29 | JV Boys Tennis | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | V Girls Golf | Fairfield Ludlowe | Home - Longshore [Directions] | 3:00 p.m. | Ludlowe 218. Staples. 188 | ED 2:00pm |
| Tue., 4/29 | JV Girls Golf | Darien | Away - CC of Darien [Directions] | 3:00 p.m. | ||
| Tue., 4/29 | V Girls Lacrosse | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 9-10 | |
| Tue., 4/29 | JV Girls Lacrosse | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 4/29 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | L 00-14 (5) | |
| Tue., 4/29 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden field [Directions] | 4:00 p.m. | Cancelled | ride with varsity |
| Tue., 4/29 | V Girls Tennis | St. Joseph | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 4/30 | JV Boys Golf | Greenwich | Home - Longshore [Directions] | 3:15 p.m. | Cancelled | |
| Wed., 4/30 | FR Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Wed., 4/30 | V Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/30 | JV Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/30 | V Co-ed Sailing | Indian Harbor Yacht Club | Away | TBA | ||
| Wed., 4/30 | V Girls Water Polo | Hotchkiss | Home - Staples HS Pool [Directions] | 3:30 p.m. | ||
| Thu., 5/1 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 4-2 | |
| Thu., 5/1 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/1 | V Co-ed Sailing | Indian Harbor Yacht Club | Away | TBA | ||
| Thu., 5/1 | V Girls Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | Greenwich. 172 | ED 2:00pm |
| Thu., 5/1 | V Girls Lacrosse | Trumbull | Home - Staples Stadium [Directions] | 5:30 p.m. | W 16-5 | |
| Thu., 5/1 | JV Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/1 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/1 | JV Girls Tennis | Fairfield Warde | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/1 | V Girls Water Polo | Choate Rosemary Hall | Away | 4:45 p.m. | ||
| Fri., 5/2 | V Baseball | Ridgefield | Home - Staples Baseball Field [Directions] | 4:00 p.m. | W 7-4 | |
| Fri., 5/2 | JV Baseball | Ridgefield | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | FR Boys Lacrosse | Fairfield Warde | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Boys Outdoor Track | Middletown Invitational | Away | 3:30 p.m. | ED 12:30 | |
| Fri., 5/2 | V Boys Tennis | Daniel Hand | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Fri., 5/2 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Girls Outdoor Track | Middletown Invitational | Away | TBA | ED 1:15 | |
| Fri., 5/2 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | W 09-00 | |
| Fri., 5/2 | JV Girls Tennis | Harding | Away - Glenwood Park [Directions] | 4:00 p.m. | Glenwood park | |
| Sat., 5/3 | V Baseball | Fairfield Ludlowe | Home - Staples Baseball Field [Directions] | 3:00 p.m. | W 10-2 | |
| Sat., 5/3 | JV Baseball | Fairfield Ludlowe | Home - Wakeman Field [Directions] | 3:00 p.m. | ||
| Sat., 5/3 | V Boys Lacrosse | Mamaroneck (NY) | Away | TBA | L 5 - 6 | |
| Sat., 5/3 | JV Boys Lacrosse | Mamaroneck (NY) | Away | 5:00 p.m. | ||
| Sat., 5/3 | FR Boys Lacrosse | Don Bosco Tournament | Away | TBA | ||
| Sat., 5/3 | V Boys Outdoor Track | Middletown Invitational | Away | 1:00 p.m. | ||
| Sat., 5/3 | V Boys Volleyball | 4 team mini tournament | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | Cancelled | |
| Sat., 5/3 | V Boys Volleyball | 4 team mini tournament | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | Cancelled | |
| Sat., 5/3 | V Girls Outdoor Track | Middletown Invitational | Away | TBA | ||
| Sat., 5/3 | V Girls Water Polo | Hopkins School | Away | 3:00 p.m. | ||
| Sun., 5/4 | V Boys Rugby | Cheshire | Home - Staples Stadium [Directions] | 12:00 p.m. | ||
| Mon., 5/5 | V Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | W 6-5 | |
| Mon., 5/5 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | FR Baseball | New Canaan | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Boys Golf | Wilton | Away - Rolling Hills [Directions] | 3:30 p.m. | 171 | |
| Mon., 5/5 | JV Boys Golf | Wilton | Away - Rolling Hills [Directions] | 3:30 p.m. | Rolling Hills | |
| Mon., 5/5 | FR Boys Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/5 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Boys Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/5 | JV Boys Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 5:30 p.m. | ride with varsity | |
| Mon., 5/5 | V Girls Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | Danbury 196. Staples 177 | ED 2:00pm |
| Mon., 5/5 | JV Girls Golf | Darien | Home - Longshore [Directions] | 3:15 p.m. | ||
| Mon., 5/5 | V Girls Outdoor Track | Harding, Norwalk | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Girls Tennis | Ridgefield | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/5 | JV Girls Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 5/6 | FR Baseball | Fairfield Ludlowe | Away - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Outdoor Track | Norwalk, Harding | Away - Testa Field, NHS [Directions] | 4:00 p.m. | ED 2:00 | |
| Tue., 5/6 | V Boys Tennis | Bridgeport Central | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/6 | V Girls Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | Trumbull 211. Staples 172 | |
| Tue., 5/6 | JV Girls Golf | Trumbull | Home - Longshore [Directions] | 3:15 p.m. | ||
| Tue., 5/6 | V Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | L 5-10 | |
| Tue., 5/6 | JV Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 5/6 | V Softball | New Canaan | Home - Wakeman Field C [Directions] | 4:00 p.m. | L 03-04 | |
| Tue., 5/6 | JV Softball | New Canaan | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/7 | V Baseball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | W 10-1 | |
| Wed., 5/7 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | FR Baseball | Stamford | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Boys Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | 149 | |
| Wed., 5/7 | JV Boys Golf | New Canaan | Away - Longshore [Directions] | 3:15 p.m. | ||
| Wed., 5/7 | JV Boys Tennis | Scarsdale (NY) | Away | 4:15 p.m. | ||
| Wed., 5/7 | V Boys Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 5/7 | JV Boys Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 5/7 | V Girls Golf | Darien | Away - TBA [Directions] | 3:00 p.m. | Darien. 204. Staples. 181 | ED 1:50pm |
| Wed., 5/7 | JV Girls Golf | Greenwich | Away - Millbrook Country Club [Directions] | 3:15 p.m. | Milbrook CC | |
| Wed., 5/7 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | JV Girls Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Girls Water Polo | Loomis Chaffee School | Away | 3:30 p.m. | ED 1:00 | |
| Thu., 5/8 | V Boys Golf | St. Joseph | Away - St. Joseph High School [Directions] | 3:15 p.m. | 160 | |
| Thu., 5/8 | JV Boys Golf | Wilton, Darien | Home - Longshore [Directions] | 3:00 p.m. | ||
| Thu., 5/8 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:30 p.m. | W 9 to 8 | |
| Thu., 5/8 | JV Boys Lacrosse | Wilton | Away - Whitten Field [Directions] | 4:00 p.m. | ||
| Thu., 5/8 | V Boys Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | W 3-0 | ED 2:00 |
| Thu., 5/8 | JV Boys Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:30 p.m. | ride with varsity | |
| Thu., 5/8 | V Girls Lacrosse | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | W 14-8 | |
| Thu., 5/8 | JV Girls Lacrosse | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | ||
| Thu., 5/8 | FR Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/8 | V Girls Outdoor Track | Loucks Games | Away | TBA | Cancelled | |
| Thu., 5/8 | V Softball | Stamford | Home - Wakeman Field C [Directions] | 4:00 p.m. | L 01-10 | |
| Thu., 5/8 | JV Softball | Stamford | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/8 | V Girls Tennis | Danbury | Away - Danbury High School Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/9 | V Baseball | Darien | Home - Staples Baseball Field [Directions] | 4:00 p.m. | W 9-5 | |
| Fri., 5/9 | JV Baseball | Darien | Home - Wakeman Field [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 5/9 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/9 | FR Boys Lacrosse | Stamford | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 5/9 | FR Boys Lacrosse | Don Bosco Tournament | Away | TBA | Cancelled | |
| Fri., 5/9 | V Girls Outdoor Track | Loucks Games | Away | TBA | Cancelled | |
| Fri., 5/9 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | 4:00 p.m. | L 00-16 (5) | |
| Fri., 5/9 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | 4:00 p.m. | Cancelled | ride with varsity |
| Sat., 5/10 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 2:00 p.m. | W 9 - 4 | |
| Sat., 5/10 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | ||
| Sat., 5/10 | FR Boys Lacrosse | Don Bosco Tournament | Away | 1:30 p.m. | ||
| Sat., 5/10 | V Boys Outdoor Track | Greater Hartford Invitational @ Simsbuty | Away | 10:00 a.m. | ||
| Sat., 5/10 | V Girls Lacrosse | Conard | Home - Staples Stadium [Directions] | 11:00 a.m. | W 12-11 | |
| Sat., 5/10 | JV Girls Lacrosse | Conard | Home - Ginny Parker Field - Staples [Directions] | 12:30 p.m. | ||
| Sat., 5/10 | FR Girls Lacrosse | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 10:00 a.m. | ||
| Sat., 5/10 | V Girls Outdoor Track | Loucks Games | Away | TBA | ||
| Mon., 5/12 | V Baseball | St. Joseph | Away - St. Joseph High School [Directions] | 4:15 p.m. | W 5-0 | |
| Mon., 5/12 | JV Baseball | St. Joseph | Away - Madison Middle School, Trumbull [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | FR Baseball | St. Joseph | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Boys Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | 156 Warde Staples 155 | |
| Mon., 5/12 | JV Boys Golf | Greenwich | Away [Directions] | 3:00 p.m. | Greenwich CC | |
| Mon., 5/12 | FR Boys Lacrosse | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Boys Tennis | Wilton | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/12 | JV Boys Tennis | Wilton | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/12 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Mon., 5/12 | V Girls Outdoor Track | Westhill, Trumbull | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Softball | St. Joseph | Home - Wakeman Field C [Directions] | 4:00 p.m. | L 01-09 | |
| Mon., 5/12 | JV Softball | St. Joseph | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Girls Tennis | Wilton | Away - WHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/13 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | 161 | |
| Tue., 5/13 | JV Boys Golf | Greenwich | Away [Directions] | 3:00 p.m. | Cancelled | ED 1:50 |
| Tue., 5/13 | V Boys Lacrosse | Westhill | Home - Staples Stadium [Directions] | 5:30 p.m. | W 15 - 4 | |
| Tue., 5/13 | JV Boys Lacrosse | Westhill | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/13 | FR Boys Lacrosse | Danbury | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 5/13 | V Boys Outdoor Track | Trumbull, Westhill | Away - McDougall Stadium [Directions] | 4:00 p.m. | ED 1:45 | |
| Tue., 5/13 | V Boys Tennis | Trumbull | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/13 | V Girls Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | New Canaan 220 Staples. 182 | ED 2:00pm |
| Tue., 5/13 | JV Girls Golf | Fairfield Ludlowe, Fairfield Warde | Home - Longshore [Directions] | 3:24 p.m. | ||
| Tue., 5/13 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 7-19 | |
| Tue., 5/13 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 5/13 | FR Girls Lacrosse | Darien | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 5/13 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 5/14 | V Baseball | Bridgeport Central | Home - Staples Baseball Field [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 5/14 | JV Baseball | Bridgeport Central | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | FR Baseball | Ridgefield | Away - East Ridge Middle School [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | V Boys Golf | Danbury, Norwalk | Home - Longshore [Directions] | 3:00 p.m. | Norwalk 167 Danbury 162 | |
| Wed., 5/14 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | V Boys Rugby | Stamford Academy | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 5/14 | V Boys Tennis | Danbury | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/14 | V Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 5/14 | JV Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | ||
| Wed., 5/14 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Trumbull 197. Staples. 177 | |
| Wed., 5/14 | JV Girls Golf | Greenwich | Home - Longshore [Directions] | 3:15 p.m. | ||
| Wed., 5/14 | FR Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Wed., 5/14 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | 4:00 p.m. | W 16-00 (5) | |
| Wed., 5/14 | JV Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 5/14 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | ||
| Thu., 5/15 | V Baseball | Norwalk | Home - Staples Baseball Field [Directions] | 4:00 p.m. | W 6-5 | |
| Thu., 5/15 | JV Baseball | Norwalk | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Thu., 5/15 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:00 p.m. | ED 1:50 New Canaan CC | |
| Thu., 5/15 | V Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | W 5 to 4 | |
| Thu., 5/15 | JV Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/15 | V Boys Tennis | Norwalk | Away - Norwalk High Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/15 | V Girls Golf | Darien, Weston | Home - Longshore [Directions] | 3:00 p.m. | Darien. 211. Weston. 218. Staples. 168 | ED 2:00pm |
| Thu., 5/15 | V Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 17-14 | |
| Thu., 5/15 | JV Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Thu., 5/15 | V Girls Outdoor Track | JV FR/SO Meet | Away | 3:30 p.m. | ||
| Thu., 5/15 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | 4:00 p.m. | L 00-02 | |
| Thu., 5/15 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | Cancelled | ride with varsity |
| Thu., 5/15 | V Girls Tennis | Norwalk | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/15 | JV Girls Tennis | Fairfield Ludlowe | Home - Town Farms Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 5/16 | FR Boys Lacrosse | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 5/16 | V Boys Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/16 | JV Boys Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | Cancelled | ride with varsity |
| Fri., 5/16 | JV Girls Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 5/17 | V Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 1:00 p.m. | W 17 - 3 | |
| Sat., 5/17 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 3:00 p.m. | ||
| Sat., 5/17 | FR Boys Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 11:00 a.m. | ||
| Sun., 5/18 | V Boys Rugby | Fairfield Prep | Home - Staples Stadium [Directions] | 12:00 p.m. | ||
| Mon., 5/19 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | W 9-2 | |
| Mon., 5/19 | JV Baseball | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | FR Baseball | Westhill | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Boys Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | 153 | |
| Mon., 5/19 | JV Boys Golf | Greenwich | Home - Longshore [Directions] | 3:20 p.m. | ||
| Mon., 5/19 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/19 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 5/19 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | ||
| Mon., 5/19 | V Boys Volleyball | Bassick | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/19 | JV Boys Volleyball | Bassick | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/19 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:00 p.m. | Ridgefield 191. Staples 182 | ED 1:30 |
| Mon., 5/19 | JV Girls Golf | Darien | Home - Longshore [Directions] | TBA | Cancelled | |
| Mon., 5/19 | V Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | 6:00 p.m. | W 22-14 | |
| Mon., 5/19 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | ||
| Mon., 5/19 | V Girls Outdoor Track | Darien, Ridgefield | Away - DHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Softball | Westhill | Home - Wakeman Field C [Directions] | 4:00 p.m. | L 06-10 | |
| Mon., 5/19 | JV Softball | Westhill | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Girls Tennis | Greenwich | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/20 | JV Baseball | Darien | Home - Staples HS Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/20 | V Boys Golf | Trumbull, Darien | Home - Longshore [Directions] | 3:00 p.m. | 145 | |
| Tue., 5/20 | V Boys Lacrosse | Brien McMahon | Home - Staples Stadium [Directions] | 7:00 p.m. | W 10 - 5 | |
| Tue., 5/20 | JV Boys Lacrosse | Brien McMahon | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/20 | V Boys Outdoor Track | Darien, Ridgefield | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/20 | JV Girls Golf | Newtown | Away [Directions] | 3:00 p.m. | Rock Ridge CC | |
| Tue., 5/20 | V Girls Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 6:00 p.m. | W 16-8 | |
| Tue., 5/20 | JV Girls Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/20 | V Softball | Nonnewaug | Home - Greens Farms Elementary School [Directions] | 7:00 p.m. | W 06-05 | |
| Tue., 5/20 | JV Girls Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Boys Golf | Brien McMahon | Home - Longshore [Directions] | 3:00 p.m. | 146 | |
| Wed., 5/21 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:15 p.m. | Brooklawn CC | |
| Wed., 5/21 | V Boys Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/21 | JV Boys Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/21 | JV Girls Golf | Trumbull | Home - Longshore [Directions] | 3:15 p.m. | Cancelled | |
| Wed., 5/21 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Wed., 5/21 | V Girls Water Polo | Hotchkiss | Away | 4:30 p.m. | ED 1:45 | |
| Thu., 5/22 | V Boys Golf | Chappa Tournament | Home - Longshore [Directions] | TBA | ||
| Thu., 5/22 | V Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 5/22 | JV Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 5/22 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | Greenwich. 182. Staples. 180 | ED 1:50 |
| Fri., 5/23 | V Baseball | Trumbull | Home - Staples Baseball Field [Directions] | 4:00 p.m. | W 9-2 | |
| Fri., 5/23 | JV Baseball | Trumbull | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 8 - 9 | |
| Fri., 5/23 | FR Boys Lacrosse | Ridgefield | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Fri., 5/23 | V Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | V Girls Lacrosse | Greenwich | Away [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:00 p.m. | L 00-02 | |
| Fri., 5/23 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 5/23 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | ED 2:00 | |
| Sat., 5/24 | V Girls Outdoor Track | Coaches vs. Cancer Invitational | Home - Staples Stadium [Directions] | 9:00 a.m. | ||
| Mon., 5/26 | V Girls Tennis | Joel Barlow | Home - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | Cancelled | |
| Tue., 5/27 | V Baseball | Greenwich | Home [Directions] | 4:00 p.m. | ||
| Tue., 5/27 | V Boys Outdoor Track | FCIAC Championships @ Danbury | Away | 2:30 p.m. | ED 11:15 | |
| Tue., 5/27 | V Boys Tennis | Greenwich | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/27 | V Girls Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | Warde 210. Staples. 168 | ED 2:00pm |
| Tue., 5/27 | V Girls Outdoor Track | FCIAC Championship | Away | TBA | ED 11:15 | |
| Tue., 5/27 | V Softball | Trinity Catholic (Scrim.) | Away - Trinity Catholic's Smith Field | 3:45 p.m. | ||
| Wed., 5/28 | V Boys Rugby | Southington | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 5/28 | V Boys Volleyball | FCIAC Semi-Finals vs. Darien at Fairfield Ludlowe | Away | 5:00 p.m. | ||
| Wed., 5/28 | JV Girls Golf | JV FCIACs | Away | TBA | ||
| Wed., 5/28 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | W 20-8 | |
| Wed., 5/28 | FR Girls Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Thu., 5/29 | V Boys Golf | Fairfield Prep | Away - Patterson Club, Fairfield, CT [Directions] | 3:00 p.m. | 167 | Patterson Club |
| Thu., 5/29 | V Boys Outdoor Track | Hatter Freshmen Invitational @ Danbury | Away | 4:00 p.m. | ED 1:30 | |
| Thu., 5/29 | V Boys Rugby | Playoffs @ Greenwich | Away | 5:30 p.m. | ||
| Thu., 5/29 | V Boys Tennis | FCIAC Finals vs Ridgefield at Wilton | Away | 4:00 p.m. | ||
| Thu., 5/29 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:15 p.m. | Staples. 151. Wilton 197 | ED 1:45 |
| Thu., 5/29 | V Softball | Fairfield Warde (Scrim.) | Away - Fairfield Warde H.S. [Directions] | 3:45 p.m. | ||
| Fri., 5/30 | V Boys Volleyball | FCIAC Finals vs. Ridgefield at Fairfield Ludlowe | Away | 7:00 p.m. | ||
| Fri., 5/30 | V Softball | Greenwich (Scrim.) | Home - Wakeman Field C [Directions] | 3:45 p.m. | ||
| Fri., 5/30 | Unified Sports Track | @ Ludlowe | Away | 3:30 p.m. | Cancelled | ED |
| Mon., 6/2 | V Boys Golf | FCIAC Golf Championship | Away | 11:15 a.m. | ||
| Mon., 6/2 | V Boys Volleyball | Newington (Scrim.) | Home - Staples H.S. Gym [Directions] | 4:45 p.m. | ||
| Mon., 6/2 | V Girls Golf | Guimares Tournament | Away | 1:00 p.m. | ED 11:00 | |
| Mon., 6/2 | V Softball | Daniel Hand | Away - Green Hill Rd. Softball Fields [Directions] | 4:00 p.m. | L 07-09 | ED 1:30 |
| Mon., 6/2 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | W 4-3 | |
| Tue., 6/3 | V Baseball | Class LL Second Round vs. Warde/So Windsor winner | Home - Staples Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 6/3 | V Boys Golf | Holihan Invitational | Away | TBA | ||
| Tue., 6/3 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Danbury HS [Directions] | 2:30 p.m. | ED 11:45 | |
| Tue., 6/3 | V Girls Lacrosse | CIAC First Round vs. Cheshire | Away | 5:00 p.m. | ||
| Tue., 6/3 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Danbury HS [Directions] | 2:30 p.m. | ||
| Tue., 6/3 | V Girls Tennis | Ridgefield | Home [Directions] | 3:00 p.m. | W 5-2 | |
| Wed., 6/4 | V Boys Lacrosse | CIAC First Round vs. Hall HS | Away | 4:30 p.m. | ED 11:45 | |
| Wed., 6/4 | V Boys Rugby | State Tournament | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Wed., 6/4 | V Girls Golf | FCIAC Championship @ Fairchild Wheeler | Away | 9:00 a.m. | ||
| Wed., 6/4 | V Girls Tennis | CIAC Class L Semifinals @ Darien | Away | 3:00 p.m. | ED 1:15 | |
| Thu., 6/5 | V Boys Outdoor Track | CIAC Class LL Championship Part 2 | Away | 2:30 p.m. | ||
| Thu., 6/5 | V Girls Outdoor Track | CIAC Class LL Championship - Part 2 | Away | 2:30 p.m. | ||
| Fri., 6/6 | V Boys Volleyball | CIAC Class L Quarterfinal vs. Xavier/Conard winner | Home [Directions] | 4:30 p.m. | ||
| Sat., 6/7 | V Boys Lacrosse | CIAC Class L Quarterfinals vs. Simsbury | Away | 3:00 p.m. | ||
| Mon., 6/9 | V Boys Golf | CIAC Division 1 Championship | Away | 8:00 a.m. | ||
| Mon., 6/9 | V Boys Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | ED 10:00 | |
| Mon., 6/9 | V Boys Volleyball | CIAC Class L Semi-final vs. Southington | Away | 7:00 p.m. | ||
| Mon., 6/9 | V Girls Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | ED 10:00 | |
| Tue., 6/10 | V Girls Golf | CIAC Girls Golf Championship | Away - Orange Hill CC - Orange [Directions] | 7:00 a.m. | ||
| Tue., 6/10 | V Girls Golf | CIAC Girls Golf Championship | Away - Orange Hill CC - Orange [Directions] | 7:00 a.m. | ||
| Wed., 6/11 | V Boys Lacrosse | Class L Semi-final vs Amity | Away | 5:00 p.m. | ||
| Sat., 6/14 | V Boys Lacrosse | Class L Final vs. Greenwich @ Brien McMahon | Away | 1:30 p.m. | ||
| Sat., 6/14 | V Boys Outdoor Track | New England Championship | Away - Norwell (MA) HS | TBA | ||
| Sat., 6/14 | V Girls Outdoor Track | New England Championship | Away - Norwell (MA) HS | TBA | ||
| Mon., 6/16 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||
| Mon., 6/16 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||
| Tue., 6/17 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||
| Tue., 6/17 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - USCG Academy | 11:30 a.m. | ||
| Wed., 6/18 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willowbrook Park - New Britain [Directions] | 11:00 a.m. | ||
| Wed., 6/18 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||