| Staples 2016-17 Athletic Events Schedule | |||||||
|---|---|---|---|---|---|---|---|
| 1252 Events Listed || Go Back || | |||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Bus Time | Note |
| TBA | JV Baseball | Bridgeport Central | Home - Wakeman Field [Directions] | TBA | |||
| TBA | JV Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | TBA | |||
| TBA | FR Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | TBA | |||
| TBA | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Cancelled | Cancelled | 2:00/5:00 | ED 1:45pm |
| TBA | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | TBA | 5:45/9:00 | Danbury Ice Rink | |
| TBA | FR Boys Soccer | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | TBA | |||
| TBA | JV Boys Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | TBA | |||
| TBA | JV Girls Golf | Fairfield Warde | Away - South Pine Creek- Par 3 [Directions] | 3:15 p.m. | 2:10/5:00 | ED 2:00, Par 3 | |
| TBA | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Vet's Park - Norwalk [Directions] | 3:30 p.m. | Junior Varsity Game | ||
| TBA | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | TBA | |||
| TBA | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | 4:00/6:30 | ||
| TBA | JV Girls Lacrosse | Westhill | Home - Ginny Parker Field - Staples [Directions] | TBA | |||
| TBA | JV Girls Lacrosse | Norwalk | Home - Ginny Parker Field - Staples [Directions] | TBA | |||
| TBA | FR Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| TBA | JV Softball | Darien | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | |||
| TBA | JV Softball | Norwalk | Home - Staples HS - Softball Field [Directions] | TBA | |||
| TBA | JV Softball | Fairfield Ludlowe | Away - Tom Haydon Field [Directions] | TBA | |||
| TBA | JV Girls Tennis | Trumbull | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Sun., 8/28 | V Field Hockey | Darien (Scrim.) | Away - DHS Stadium Field [Directions] | 3:00 p.m. | 1:30/4:00 | ||
| Mon., 8/29 | V Football | Scrimmage vs. New Canaan and Hand HS | Home - Staples Stadium [Directions] | 5:00 p.m. | |||
| Tue., 8/30 | V Boys Soccer | Fairfield Prep (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | |||
| Thu., 9/1 | FR Football | New Canaan and Norwalk | Away | 4:30 p.m. | 3:30/5:30 | ||
| Thu., 9/1 | V Boys Soccer | Kent School (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Thu., 9/1 | V Field Hockey | Bethel (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Thu., 9/1 | V Girls Soccer | Bloomfield (Scrim.) | Away - Phil Rubin Stadium [Directions] | 5:00 p.m. | 2:30/6:00 | ||
| Fri., 9/2 | V Football | Fairfield Prep (Scrim.) | Home - Staples Stadium [Directions] | 4:15 p.m. | |||
| Fri., 9/2 | V Girls Soccer | Glastonbury (Scrim.) | Away - GHS Field #4 [Directions] | 3:45 p.m. | 1:00/6:00 | ||
| Fri., 9/2 | JV Girls Soccer | Glastonbury (Scrim.) | Away - GHS Field #12 [Directions] | 3:45 p.m. | ride with varsity | ||
| Sat., 9/3 | V Boys Soccer | Wethersfield Jamboree | Away | 10:00 a.m. | 7:45am/12:00 | ||
| Sat., 9/3 | JV Boys Soccer | Shelton Jamboree | Away | 3:00 p.m. | 1:15 | ||
| Sat., 9/3 | V Girls Soccer | Conard Jamboree | Away | 9:10 a.m. | 7:00am/11:00 | ||
| Mon., 9/5 | V Boys Soccer | Martin Luther King HS | Home - Wakeman Field B (turf) [Directions] | 12:30 p.m. | |||
| Tue., 9/6 | V Girls Soccer | Weston (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 3:45 p.m. | |||
| Tue., 9/6 | JV Girls Soccer | Weston (Scrim.) | Home - Wakeman Field E (grass) [Directions] | 3:45 p.m. | |||
| Tue., 9/6 | FR Girls Soccer | Weston (Scrim.) | Home - Wakeman Field A [Directions] | 3:45 p.m. | |||
| Wed., 9/7 | V Field Hockey | Greens Farms Academy (Scrim.) | Away | 3:30 p.m. | 2:30/5:00 | ||
| Wed., 9/7 | V Girls Soccer | Pomperaug (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 5:00 p.m. | |||
| Wed., 9/7 | JV Girls Soccer | Pomperaug (Scrim.) | Home - Wakeman Field E (grass) [Directions] | 5:00 p.m. | |||
| Wed., 9/7 | V Girls Volleyball | Val Dickerson Jamboree | Home - Staples Field House [Directions] | 3:30 p.m. | |||
| Thu., 9/8 | FR Girls Soccer | St. Lukes (Scrim.) | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | |||
| Fri., 9/9 | V Boys Cross Country | Blue and White Trials | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Fri., 9/9 | V Football | Brien McMahon | Home - Staples Stadium [Directions] | 7:00 p.m. | W 38-13 | ||
| Fri., 9/9 | V Boys Soccer | Trinity Catholic | Home - Staples High [Directions] | 4:00 p.m. | W 6-0 | ||
| Fri., 9/9 | V Girls Cross Country | Blue and White Trials | Home - Staples Stadium [Directions] | 2:45 p.m. | |||
| Fri., 9/9 | V Field Hockey | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 5-0 | ||
| Fri., 9/9 | JV Field Hockey | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Fri., 9/9 | V Girls Volleyball | Amity | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 2-3 | ||
| Fri., 9/9 | JV Girls Volleyball | Amity | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Sat., 9/10 | FR Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 10:00 a.m. | 8:30/11:00 | ||
| Sat., 9/10 | V Field Hockey | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 6-0 | ||
| Sat., 9/10 | JV Field Hockey | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Sat., 9/10 | FR Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | 8:15/11:00 | ||
| Sat., 9/10 | V Girls Soccer | Trinity Catholic | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 12-1 | ||
| Mon., 9/12 | V Boys Soccer | Danbury | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 2-1 | ||
| Mon., 9/12 | JV Boys Soccer | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 0-0 | ||
| Mon., 9/12 | FR Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | W 4-0 | 4:00/7:00 | |
| Mon., 9/12 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | W 2-0 | 2:00/5:00 | ED 1:45 |
| Mon., 9/12 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 | |
| Mon., 9/12 | V Girls Volleyball | Joel Barlow | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-2 | ||
| Mon., 9/12 | JV Girls Volleyball | Joel Barlow | Home [Directions] | 5:30 p.m. | |||
| Mon., 9/12 | Miscellaneous Events | Frosh FH practice | Home - Staples Stadium [Directions] | 6:30 p.m. | |||
| Tue., 9/13 | V Boys Cross Country | Danbury, Darien, Norwalk | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Tue., 9/13 | V Girls Cross Country | Danbury, Darien, Norwalk | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Tue., 9/13 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 8-0 | 5:30/8:00 | |
| Tue., 9/13 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | 4:00/6:30 | ||
| Tue., 9/13 | FR Field Hockey | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Tue., 9/13 | FR Girls Soccer | Danbury | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Wed., 9/14 | SO Football | Darien | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Wed., 9/14 | V Boys Soccer | Trumbull | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 0-0 | ||
| Wed., 9/14 | JV Boys Soccer | Trumbull | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 2-1 | ||
| Wed., 9/14 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Wed., 9/14 | JV Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Thu., 9/15 | FR Football | Danbury | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Thu., 9/15 | FR Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | Cancelled | Cancelled | 2:30/5:00 | |
| Thu., 9/15 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 8-0 | 2:30/5:00 | |
| Thu., 9/15 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | 3:30/6:30 | ||
| Thu., 9/15 | FR Field Hockey | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Thu., 9/15 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | T 1-1 | 5:00/8:00 | |
| Thu., 9/15 | JV Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Thu., 9/15 | FR Girls Soccer | Trumbull | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Fri., 9/16 | V Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 7:00 p.m. | W 36-7 | 4:00/9:00 | 2 buses |
| Fri., 9/16 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | L 1-0 | 2:30/5:00 | |
| Fri., 9/16 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | W 2-1 | 2:30/5:00 | |
| Fri., 9/16 | FR Boys Soccer | Stamford | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 4-1 | ||
| Fri., 9/16 | V Competitive Cheerleading | Danbury | Away [Directions] | 7:00 p.m. | 5:00/9:00 | ||
| Fri., 9/16 | V Girls Swimming and Diving | Greenwich | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Fri., 9/16 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | W 3-0 | 2:30/5:00 | |
| Fri., 9/16 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ride with varsity | ||
| Fri., 9/16 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Sat., 9/17 | V Boys Cross Country | Stratton Brook Invitational @ Stratton Brook Park | Away | 9:00 a.m. | 8:00am | ||
| Sat., 9/17 | JV Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 10:00 a.m. | 8:00/11:30 | ||
| Sat., 9/17 | V Girls Cross Country | Stratton Brook Invitaional | Away | 9:30 a.m. | 8:000am | ||
| Sat., 9/17 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | W 5-0 | 3:30 | |
| Sat., 9/17 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | 5:00/7:30 | shuttle with varsity | |
| Mon., 9/19 | V Girls Soccer | Stamford | Home - Wakeman Field B (turf) [Directions] | 5:00 p.m. | W 8-0 | ||
| Mon., 9/19 | JV Girls Soccer | Stamford | Home - Wakeman Field B (turf) [Directions] | 3:30 p.m. | |||
| Mon., 9/19 | V Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Mon., 9/19 | JV Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Mon., 9/19 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Mon., 9/19 | Miscellaneous Events | Frosh FH practice | Home - Staples Stadium [Directions] | 6:30 p.m. | |||
| Tue., 9/20 | V Boys Cross Country | New Canaan, Wilton, Stamford, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00/5:00 2 buses | ED 1:30 | |
| Tue., 9/20 | V Boys Soccer | Ridgefield | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 0-0 | ||
| Tue., 9/20 | JV Boys Soccer | Ridgefield | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 2-0 | ||
| Tue., 9/20 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | W 5-2 | 2:30/5:00 | |
| Tue., 9/20 | V Girls Cross Country | New Canaan, Wilton, Stamford, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:30 | |
| Wed., 9/21 | SO Football | New Canaan | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Wed., 9/21 | V Field Hockey | St. Joseph | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 14-0 | ||
| Wed., 9/21 | JV Field Hockey | St. Joseph | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Wed., 9/21 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 1-2 | 4:00/7:00 | |
| Wed., 9/21 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Wed., 9/21 | FR Girls Soccer | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Wed., 9/21 | V Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 2-3 | ||
| Wed., 9/21 | JV Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Wed., 9/21 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Thu., 9/22 | FR Football | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | 4:30/7:00 | ||
| Thu., 9/22 | V Boys Soccer | Bridgeport Central | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 7-1 | ||
| Thu., 9/22 | JV Boys Soccer | Bridgeport Central | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | T 2-2 | ||
| Thu., 9/22 | V Field Hockey | Westhill | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 4-0 | ||
| Thu., 9/22 | JV Field Hockey | Westhill | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Thu., 9/22 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Thu., 9/22 | FR Girls Volleyball | Stamford | Home - Staples Field House [Directions] | 4:00 p.m. | |||
| Fri., 9/23 | V Football | Wilton | Home - Staples Stadium [Directions] | 7:00 p.m. | W 42-6 | Homecoming | |
| Fri., 9/23 | FR Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 9/23 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | 2:30/5:00 | |
| Fri., 9/23 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 3:30 p.m. | L 0-3 | 2:00/5:00 | |
| Fri., 9/23 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ride with varsity | ||
| Sat., 9/24 | V Boys Cross Country | Bowdoin Park Classic, Wappinger Falls NY | Away | 10:00 a.m. | 7:15am | ||
| Sat., 9/24 | JV Football | Wilton | Home - Staples Stadium [Directions] | 10:00 a.m. | |||
| Sat., 9/24 | JV Girls Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 10:30 a.m. | |||
| Mon., 9/26 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | T 0-0 | 2:45/5:30 | |
| Mon., 9/26 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | T 1-1 | 3:00/5:30 | |
| Mon., 9/26 | FR Boys Soccer | Greenwich | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 2-0 | ||
| Mon., 9/26 | V Girls Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 1-3 | ||
| Mon., 9/26 | JV Girls Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Mon., 9/26 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Mon., 9/26 | Miscellaneous Events | Frosh FH practice | Home - Staples Stadium [Directions] | 6:30 p.m. | |||
| Tue., 9/27 | V Boys Cross Country | Greenwich, Brien McMahon, Fairfield Ludlowe | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Tue., 9/27 | V Girls Cross Country | Greenwich, Brien McMahon, Fairfield Ludlowe | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Tue., 9/27 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | W 2-1 | 2:30/5:00 | |
| Tue., 9/27 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | 4:00/6:30 | ||
| Tue., 9/27 | FR Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Tue., 9/27 | V Girls Soccer | Greenwich | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 9-0 | ||
| Tue., 9/27 | JV Girls Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Tue., 9/27 | JV Girls Swimming and Diving | Greenwich | Away [Directions] | 7:15 p.m. | 5:45/8:15 | ||
| Wed., 9/28 | SO Football | Greenwich | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Wed., 9/28 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 2-0 | 2:30/5:00 | |
| Wed., 9/28 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | W 4-2 | 2:30/5:00 | |
| Wed., 9/28 | V Boys Water Polo | Canterbury | Away - Loomis Chaffe School | 4:30 p.m. | 2:00/5:30 | ||
| Wed., 9/28 | V Boys Water Polo | Loomis Chaffee School | Away | 5:30 p.m. | |||
| Wed., 9/28 | FR Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | 2:30/5:00 | ||
| Wed., 9/28 | V Girls Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Wed., 9/28 | JV Girls Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Thu., 9/29 | FR Football | Fairfield Warde | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Thu., 9/29 | V Girls Soccer | St. Joseph | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 1-2 | ||
| Thu., 9/29 | JV Girls Soccer | St. Joseph | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Fri., 9/30 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | W 35-6 | 4:00/9:00 | 2 buses |
| Fri., 9/30 | JV Boys Soccer | Westhill | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-2 | ||
| Fri., 9/30 | JV Boys Water Polo | Greenwich Tournament | Away | TBA | 5:30/8:30 | ||
| Fri., 9/30 | V Competitive Cheerleading | Fairfield Warde | Away [Directions] | 7:00 p.m. | 5:30/9:00 | ||
| Fri., 9/30 | V Field Hockey | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | T 0-0 | ||
| Fri., 9/30 | JV Field Hockey | Wilton | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Fri., 9/30 | FR Field Hockey | Wilton | Away - Wilton HS - Grass Field [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 9/30 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | L 0-3 | 2:10/6:00 | ED 1:55 |
| Fri., 9/30 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ride with varsity | ED 1:155 | |
| Fri., 9/30 | FR Girls Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | |||
| Fri., 9/30 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Sat., 10/1 | JV Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 10:00 a.m. | 8:30/11:30 | ||
| Sat., 10/1 | V Boys Soccer | Westhill | Home - Loeffler Field - Staples HS [Directions] | 3:00 p.m. | W 2-0 | ||
| Sat., 10/1 | FR Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 11:00 a.m. | W 5-0 | 10:15/12:00 | |
| Sat., 10/1 | JV Boys Water Polo | Greenwich Tournament | Away | TBA | Yes | ||
| Sat., 10/1 | JV Girls Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 11:00 a.m. | |||
| Sun., 10/2 | JV Boys Water Polo | Greenwich Tournament | Away | TBA | Yes | ||
| Wed., 10/5 | V Boys Cross Country | St. Joseph, Westhill, Trumbull | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:00/6:00 2 buses | ED 1:30 | |
| Wed., 10/5 | V Boys Soccer | Brien McMahon | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 5-0 | ||
| Wed., 10/5 | JV Boys Soccer | Brien McMahon | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-0 | ||
| Wed., 10/5 | V Girls Cross Country | St. Joseph, Westhill, Trumbull | Away [Directions] | 4:00 p.m. | 2:00/6:00 | ED 1:30 | |
| Wed., 10/5 | V Girls Swimming and Diving | Fairfield Warde | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Wed., 10/5 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | L 2-3 | 2:30/5:00 | |
| Wed., 10/5 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ride with varsity | ||
| Wed., 10/5 | FR Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | |||
| Thu., 10/6 | V Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 3-0 | ||
| Thu., 10/6 | JV Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Thu., 10/6 | FR Field Hockey | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Thu., 10/6 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:15 p.m. | W 3-0 | 5:30/8:00 | |
| Thu., 10/6 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | 4:15 | shuttle with varsity | |
| Fri., 10/7 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | W 2-0 | 3:30/6:00 | |
| Fri., 10/7 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | W 1-0 | 2:30 | shuttle with varsity |
| Fri., 10/7 | FR Boys Soccer | Fairfield Ludlowe | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 2-1 | ||
| Fri., 10/7 | V Girls Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Fri., 10/7 | JV Girls Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Fri., 10/7 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Sat., 10/8 | V Boys Cross Country | Wickham Park Invitational | Away | 9:40 p.m. | 6:45am | ||
| Sat., 10/8 | V Football | Norwich Free Academy | Away - NFA Turf Field [Directions] | 1:00 p.m. | L 14-33 | 9:00/3:00 | |
| Sat., 10/8 | V Competitive Cheerleading | Norwich Free Academy | Away [Directions] | 1:00 p.m. | 10:00/3:00 | ||
| Sat., 10/8 | V Girls Cross Country | Wickham Park Invitaional | Away | 9:40 p.m. | 6:45am | ||
| Sat., 10/8 | V Girls Soccer | Fairfield Ludlowe | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-1 | ||
| Sat., 10/8 | JV Girls Soccer | Fairfield Ludlowe | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Sat., 10/8 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:00 p.m. | |||
| Sat., 10/8 | JV Girls Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 11:00 a.m. | |||
| Sat., 10/8 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Mon., 10/10 | V Boys Cross Country | Fairfield Warde, Ridgefield | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:00/5:30 2 buses | ED 1:45 | |
| Mon., 10/10 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:30 p.m. | T 1-1 | 6:00/8:30 | |
| Mon., 10/10 | JV Boys Soccer | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:30 p.m. | T 1-1 | 3:00/5:30 | |
| Mon., 10/10 | V Boys Water Polo | Choate Rosemary Hall | Away | 4:00 p.m. | 2:00/6:00 | ED 1:45 | |
| Mon., 10/10 | JV Boys Water Polo | Choate Rosemary Hall | Away | 5:00 p.m. | ride with varsity | ||
| Mon., 10/10 | V Girls Cross Country | Fairfield Warde, Ridgefield | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:00/5:30 | ED 1:30 | |
| Mon., 10/10 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | W 3-0 | 2:30/5:00 | |
| Mon., 10/10 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | 4:00/6:30 | ||
| Mon., 10/10 | FR Girls Soccer | Masuk | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Mon., 10/10 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:15/4:30 | ED 1:00 | |
| Tue., 10/11 | V Girls Soccer | Norwalk | Home - Loeffler Field - Staples HS [Directions] | 3:00 p.m. | W 8-1 | ||
| Tue., 10/11 | JV Girls Soccer | Norwalk | Home - Wakeman Field E (grass) [Directions] | 3:00 p.m. | |||
| Thu., 10/13 | FR Football | Stamford | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Thu., 10/13 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | T 0-0 | 2:30/5:00 | |
| Thu., 10/13 | JV Boys Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Thu., 10/13 | FR Boys Soccer | Darien | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-0 | ||
| Thu., 10/13 | V Boys Water Polo | Hopkins School | Home - Staples HS Pool [Directions] | 3:30 p.m. | |||
| Thu., 10/13 | V Boys Water Polo | Horace Mann (NY) | Home - Staples HS Pool [Directions] | 4:30 p.m. | |||
| Thu., 10/13 | JV Boys Water Polo | Horace Mann (NY) | Home - Staples HS Pool [Directions] | 5:30 p.m. | |||
| Thu., 10/13 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | T 1-1 | 2:30/5:00 | |
| Thu., 10/13 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | 4:00/6:30 | ||
| Thu., 10/13 | FR Field Hockey | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Thu., 10/13 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 3:30 p.m. | T 4-4 | 1:45/4:30 | ED 1:30 |
| Thu., 10/13 | JV Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:45 p.m. | 3:00/5:45 | ||
| Thu., 10/13 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 | |
| Thu., 10/13 | V Girls Volleyball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | L 2-3 | ||
| Thu., 10/13 | JV Girls Volleyball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Fri., 10/14 | V Football | Stamford | Away - Stamford HS [Directions] | 6:00 p.m. | W 42-13 | 3:30/8:00 | 2 buses |
| Fri., 10/14 | V Boys Water Polo | Greenwich Tournament | Away | 6:00 p.m. | 4:00/7:00 | ||
| Fri., 10/14 | V Competitive Cheerleading | Stamford | Away [Directions] | 6:00 p.m. | 4:00/8:00 | ||
| Fri., 10/14 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | 2:30/5:00 | |
| Fri., 10/14 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | ||
| Fri., 10/14 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | |||
| Sat., 10/15 | V Boys Soccer | New Canaan | Home - Loeffler Field - Staples HS [Directions] | 1:30 p.m. | W 2-1 | ||
| Sat., 10/15 | V Boys Water Polo | Greenwich Tournament | Away | 10:00 a.m. | 8:30am/1:00pm | ||
| Sat., 10/15 | V Girls Soccer | Darien | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-0 | ||
| Sat., 10/15 | JV Girls Soccer | Darien | Home - Wakeman Field B (turf) [Directions] | 4:15 p.m. | |||
| Sat., 10/15 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Mon., 10/17 | JV Football | Stamford | Away - Stamford HS [Directions] | 5:00 p.m.. | 3:00/6:30 | ||
| Mon., 10/17 | JV Boys Soccer | New Canaan | Away - Saxe MS [Directions] | 4:00 p.m. | W 1-0 | 2:30/5:00 | |
| Mon., 10/17 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Mon., 10/17 | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Mon., 10/17 | FR Girls Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Mon., 10/17 | V Girls Swimming and Diving | Trumbull | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Mon., 10/17 | JV Girls Swimming and Diving | Trumbull | Home - Staples HS Pool [Directions] | 3:30 p.m. | |||
| Mon., 10/17 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | W 3-0 | 2:30/6:00 | |
| Mon., 10/17 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | ride with varsity | ||
| Tue., 10/18 | V Field Hockey | Fairfield Warde | Home - Staples Stadium [Directions] | 6:30 p.m. | W 2-0 | ||
| Tue., 10/18 | JV Field Hockey | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | |||
| Tue., 10/18 | V Girls Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | W 3-0 | 2:30/5:00 | |
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship @ Waveny Park | Away | 2:15 p.m. | 11:45am | ED 11:15 | |
| Wed., 10/19 | V Boys Water Polo | Brunswick School | Home - Staples HS Pool [Directions] | 3:00 p.m. | |||
| Wed., 10/19 | V Boys Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 5:00 p.m. | |||
| Wed., 10/19 | JV Boys Water Polo | Brunswick School | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Wed., 10/19 | JV Boys Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 6:00 p.m. | |||
| Wed., 10/19 | V Girls Cross Country | FCIAC Championship @ Waveny Park | Away | 2:15 p.m. | 11:45 | ED 11:15 | |
| Wed., 10/19 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 3:30 p.m. | 1:30/5:00 | ED 1:15 | |
| Wed., 10/19 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | W 3-1 | 2:30/5:00 | |
| Wed., 10/19 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ride with varsity | ||
| Wed., 10/19 | FR Girls Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | |||
| Thu., 10/20 | FR Football | Ridgefield | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Thu., 10/20 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 6:00 p.m. | T 1-1 | 4:30/7;00 | |
| Thu., 10/20 | JV Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Thu., 10/20 | FR Boys Soccer | Wilton | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 4-2 | ||
| Thu., 10/20 | V Field Hockey | Danbury | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 9-0 | ||
| Thu., 10/20 | JV Field Hockey | Danbury | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Thu., 10/20 | FR Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 10/21 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 7-42 | 4:00/9:00 2 buses | 2 buses |
| Fri., 10/21 | V Boys Water Polo | Choate Rosemary Hall | Home - Staples HS Pool [Directions] | 4:45 p.m. | |||
| Fri., 10/21 | JV Boys Water Polo | Choate Rosemary Hall | Home - Staples HS Pool [Directions] | 5:45 p.m. | |||
| Fri., 10/21 | V Competitive Cheerleading | Ridgefield | Away [Directions] | 7:00 p.m. | 4:45/9:00 | ||
| Fri., 10/21 | V Girls Soccer | Wilton | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-0 | ||
| Fri., 10/21 | JV Girls Soccer | Wilton | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Fri., 10/21 | FR Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 10/21 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Staples HS Pool [Directions] | 2:30 p.m. | 1:45/4:15 | ED 1:30 | |
| Fri., 10/21 | V Girls Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-2 | ||
| Fri., 10/21 | JV Girls Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | |||
| Fri., 10/21 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Sat., 10/22 | JV Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 10:30 a.m. | 8:30/12:00 | ||
| Sat., 10/22 | V Boys Water Polo | Brunswick School | Away | 10:00 a.m. | 8:30am/12:00pm | ||
| Sat., 10/22 | JV Boys Water Polo | Brunswick School | Away | 11:00 a.m. | |||
| Mon., 10/24 | V Boys Soccer | Fairfield Warde | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 2-0 | ||
| Mon., 10/24 | JV Boys Soccer | Fairfield Warde | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 1-0 | ||
| Mon., 10/24 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | W 1-0 | 2:30/5:00 | |
| Mon., 10/24 | V Girls Volleyball | Weston | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-2 | ||
| Mon., 10/24 | JV Girls Volleyball | Weston | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Mon., 10/24 | FR Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Tue., 10/25 | V Boys Cross Country | JV Invitational | Away | Cancelled | Cancelled | Yes | |
| Tue., 10/25 | V Girls Cross Country | JV Invitational | Away | Cancelled | Cancelled | Yes | |
| Tue., 10/25 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 5-0 | 5:30/6:00 | |
| Tue., 10/25 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | 4:00 | shuttle with varsity | |
| Tue., 10/25 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | T 1-1 | 5:30/8:00 | |
| Tue., 10/25 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Tue., 10/25 | FR Girls Soccer | Fairfield Warde | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Wed., 10/26 | SO Football | New Canaan | Home [Directions] | 6:00 p.m. | |||
| Wed., 10/26 | FR Boys Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-0 | ||
| Wed., 10/26 | V Boys Water Polo | Hotchkiss | Away | 3:00 p.m. | 1:00/5:00 | ED 12:45 | |
| Wed., 10/26 | JV Boys Water Polo | Hotchkiss | Away | 4:00 p.m. | ED 12:45 | ||
| Wed., 10/26 | FR Girls Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 10/26 | V Girls Swimming and Diving | Westhill/Stamford | Home - Staples HS Pool [Directions] | 3:30 p.m. | |||
| Wed., 10/26 | JV Girls Swimming and Diving | Westhill/Stamford | Home - Staples HS Pool [Directions] | 3:30 p.m. | |||
| Wed., 10/26 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 6:15 p.m. | L 2-3 | 3:00/7:15 | |
| Wed., 10/26 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ride with varsity | ||
| Wed., 10/26 | FR Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | |||
| Fri., 10/28 | V Boys Soccer | Greenwich | Away [Directions] | 3:30 p.m. | L 2-1 | 1:30/4:30 | ED 1:20 |
| Fri., 10/28 | V Field Hockey | FCIAC Quarter Finals | Home - Ginny Parker Field - Staples [Directions] | 3:30 p.m. | |||
| Fri., 10/28 | V Girls Soccer | FCIAC Quarter Finals vs. Darien | Home - Loeffler Field - Staples HS [Directions] | 3:30 p.m. | |||
| Fri., 10/28 | V Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 0-3 | ||
| Fri., 10/28 | JV Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Fri., 10/28 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 3:10 p.m. | 11:00am | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 3:40 p.m. | 11:00 | ||
| Sat., 10/29 | JV Girls Swimming and Diving | JV FCIAC @ Greenwich HS | Away | 1:30 p.m. | 11:00/3:30 | ||
| Tue., 11/1 | V Boys Cross Country | Danbury Freshmen Invitational | Away | 4:00 p.m. | 1:45 | ED 1:15 | |
| Tue., 11/1 | V Girls Cross Country | Danbury Freshmen Invitational | Away | 4:00 p.m. | ED 1:15 | ||
| Tue., 11/1 | V Field Hockey | FCIAC Semi-finals vs Darien at Brien McMahon HS | Away | 7:30 p.m. | 5:45/8:30 | ||
| Tue., 11/1 | V Girls Soccer | FCIAC Semi-finals vs Ridgefield @ Wilton HS | Away | 7:00 p.m. | 5:15/8:00 | ||
| Tue., 11/1 | V Girls Swimming and Diving | FCIAC Swimming Trials | Away | 4:00 p.m. | 2:00 | ||
| Tue., 11/1 | V Girls Volleyball | FCIAC Quarter Finals vs Ridgefield | Away | 5:00 p.m. | 3:00/6:00 | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championship | Away | 4:00 p.m. | |||
| Thu., 11/3 | FR Football | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30/6:00 | ||
| Thu., 11/3 | V Boys Soccer | Joel Barlow (Scrim.) | Away - Field J (competition field) [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Thu., 11/3 | V Field Hockey | FCIAC Championship vs Wilton @ Brien McMahon | Away | 7:00 p.m. | 5:15/8:00 | ||
| Thu., 11/3 | V Girls Swimming and Diving | FCIAC Championship Finals | Away | 6:30 p.m. | 3:45/8:30 | ||
| Fri., 11/4 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | 10:00 | ED 9:30 | |
| Fri., 11/4 | V Football | St. Joseph | Home - Staples Stadium [Directions] | 7:00 p.m. | L 17-24 | ||
| Fri., 11/4 | V Boys Water Polo | Loomis Chaffee School | Home - Staples HS Pool [Directions] | 4:30 p.m. | |||
| Fri., 11/4 | JV Boys Water Polo | Loomis Chaffee School | Home - Staples HS Pool [Directions] | 5:45 p.m. | |||
| Fri., 11/4 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | 10:30 | ED 10:00 | |
| Sat., 11/5 | JV Football | St. Joseph | Home - Staples Stadium [Directions] | 10:00 a.m. | |||
| Sat., 11/5 | V Boys Water Polo | Hotchkiss | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Sat., 11/5 | JV Boys Water Polo | Hotchkiss | Home [Directions] | 5:00 p.m. | |||
| Mon., 11/7 | V Girls Volleyball | Class LL First Round vs. Simsbury | Away | 6:00 p.m. | 3:00/6:00 | ||
| Tue., 11/8 | V Boys Soccer | South Windsor | Away - SWHS Stadium Turf Field [Directions] | 2:00 p.m. | W 1-0 | 10:30am/3:00pm | |
| Wed., 11/9 | V Field Hockey | Class L First Round | Home - Ginny Parker Field - Staples [Directions] | 2:00 p.m. | |||
| Wed., 11/9 | V Girls Soccer | CIAC Class LL First Round vs. New Canaan | Home - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | |||
| Thu., 11/10 | SO Football | Darien | Home - @ Staples [Directions] | 5:30 p.m. | |||
| Thu., 11/10 | FR Football | Darien | Away - DHS Stadium East Turf Field [Directions] | 3:00 p.m. | 1:30/4:30 | ED 1:15 | |
| Thu., 11/10 | V Boys Soccer | New Milford | Away - New Milford HS [Directions] | 2:00 p.m. | W 2-0 | 11:15/3:00 | ED 11:15 |
| Thu., 11/10 | V Girls Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS | 4:30 p.m. | |||
| Thu., 11/10 | V Girls Volleyball | Class LL Second Round vs Stamford | Away | 6:00 p.m. | 4:15/7:00 | ||
| Fri., 11/11 | V Football | Darien | Home - Staples Stadium [Directions] | 7:00 p.m. | L 0-27 | ||
| Fri., 11/11 | V Field Hockey | Class L Quarterfinals vs. Wilton | Home [Directions] | 2:00 p.m. | ED 12:45 | ||
| Fri., 11/11 | V Girls Soccer | Class LL Second Round vs. McMahon | Home - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | ED 12:45 | ||
| Sat., 11/12 | V Boys Cross Country | New England Championship | Away - Ponaganset HS (RI) [Directions] | TBA | |||
| Sat., 11/12 | V Boys Soccer | Farmington | Away [Directions] | 2:00 p.m. | L 1-0 | 10:30/3:00 | |
| Sat., 11/12 | V Girls Cross Country | New England Championship | Away - Ponaganset HS (RI) [Directions] | TBA | |||
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 6:00 p.m. | 2:00/8:00 | ||
| Mon., 11/14 | V Girls Soccer | Class LL Quarterfinals vs Glastonbury | Away | 2:00 p.m. | 10:30/3:00 | ||
| Wed., 11/16 | V Field Hockey | Class L Semi-finals vs. Enfield @ Watertown | Away | 4:00 p.m. | 1:30/5:00 | ED 1:15 | |
| Wed., 11/16 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 6:00 p.m. | 2:00/7:00 | ED 1:45 | |
| Thu., 11/17 | FR Football | Greenwich | Home - Staples Stadium [Directions] | 6:00 p.m. | |||
| Fri., 11/18 | JV Football | Greenwich | Away - Cardinal Stadium [Directions] | 3:00 p.m. | 1:45/4:00 | ED 1:30 | |
| Fri., 11/18 | V Girls Swimming and Diving | CIAC Open Diving | Away - Bulkeley HS [Directions] | 5:30 p.m. | |||
| Sat., 11/19 | V Field Hockey | Class L Finals vs. Darien at Wethersfield HS | Away | 10:00 a.m. | 7:45am/11:00am | ||
| Sat., 11/19 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | 8:30am/12:00 | ||
| Thu., 11/24 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | L 10-37 | 7:00am/12:00 | 2 buses |
| Thu., 11/24 | V Competitive Cheerleading | Greenwich | Away [Directions] | 10:00 a.m. | 7:45/12:00 | ||
| Sat., 12/3 | V Girls Ice Hockey | FCIAC Jamboree | Away - Shelton Rinks | 6:00 p.m. | 4:15 pm | ||
| Sat., 12/3 | JV Girls Ice Hockey | Taft (Scrim.) | Away - The Taft School | 2:00 p.m. | 12:00 pm | ||
| Sat., 12/3 | JV Girls Ice Hockey | Taft (Scrim.) | Away - The Taft School | 2:00 p.m. | 12:00 pm | ||
| Tue., 12/6 | V Girls Basketball | Norwalk (Scrim.) | Away - Norwalk High Gym [Directions] | 5:15 p.m. | 4:00pm/6:15 | ||
| Tue., 12/6 | V Girls Squash | New Haven @ Yale | Away | 3:45 p.m. | 2:30/4:45 | ||
| Wed., 12/7 | V Boys Ice Hockey | Lyman Hall (Scrim.) | Home - Milford Ice Pavilion [Directions] | 4:15 p.m. | 2:15/5:15 | ||
| Wed., 12/7 | V Boys Squash | New Haven @ Yale | Away | 5:30 p.m. | 4:00pm/6:30 | ||
| Wed., 12/7 | V Girls Ice Hockey | Farmington (Scrim.) | Home - Terry Conners Ice Rink [Directions] | 7:00 p.m. | |||
| Thu., 12/8 | V Girls Basketball | Kolbe Cathedral (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Thu., 12/8 | JV Girls Basketball | Kolbe Cathedral (Scrim.) | Home - Staples H.S. Gym [Directions] | TBA | |||
| Fri., 12/9 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 5:00 p.m. | 3:45/6:00 | ||
| Fri., 12/9 | V Boys Indoor Track | Blue and White Trials | Home [Directions] | 2:45 p.m. | |||
| Fri., 12/9 | V Boys Squash | Greens Farms Academy | Away | 5:00 p.m. | |||
| Fri., 12/9 | V Girls Indoor Track | Blue and White Trials | Home - Staples Field House [Directions] | 3:00 p.m. | |||
| Fri., 12/9 | V Girls Squash | Greens Farms Academy | Away | 4:00 p.m. | |||
| Sat., 12/10 | V Boys Ice Hockey | Shelton Jamboree | Away | 6:30 p.m. | 4:15/8:30 | ||
| Sat., 12/10 | V Boys Indoor Track | Blue and White Trials | Home [Directions] | 9:00 a.m. | |||
| Sat., 12/10 | V Girls Indoor Track | Blue and White Trials | Home - Staples Field House [Directions] | 9:00 a.m. | |||
| Mon., 12/12 | V Boys Ice Hockey | East Haven Coop (Scrim.) | Away - DiLungo Rink [Directions] | 3:30 p.m. | 1:15/4:30 | ED 1:00 | |
| Mon., 12/12 | V Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | W 43=28 | ||
| Mon., 12/12 | V Girls Squash | Darien | Home - Chelsea Piers [Directions] | 8:30 p.m. | |||
| Tue., 12/13 | V Boys Basketball | Stratford (Scrim.) | Home - Staples H.S. Gym [Directions] | 3:00 p.m. | |||
| Wed., 12/14 | V Boys Basketball | Foran (Scrim.) | Away - Edna L. Fraser Gymnasium [Directions] | 5:30 p.m. | 4:00/6:30 | ||
| Wed., 12/14 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavilion [Directions] | 3:00 p.m. | 1:30/4:00 | ED 1:15 | |
| Wed., 12/14 | V Wrestling | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 6:00 p.m. | 4:30/7:00 | ||
| Wed., 12/14 | V Girls Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | W 54-33 | ||
| Wed., 12/14 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:50 p.m. | Junior Varsity contest | ||
| Thu., 12/15 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:30pm | 2:40/5:30 | ||
| Thu., 12/15 | V Wrestling | Practice | Home - Weston HS [Directions] | 3:00pm | 2:30/5:00 | ||
| Thu., 12/15 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Fri., 12/16 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:30pm | 2:40/5:30 | ||
| Fri., 12/16 | V Girls Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 7:15 p.m. | W 39-31 | ||
| Fri., 12/16 | JV Girls Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:45 p.m. | |||
| Fri., 12/16 | FR Girls Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | |||
| Sat., 12/17 | V Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 3:00 p.m. | W 59-49 | ||
| Sat., 12/17 | V Boys Ice Hockey | Branford | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 4-3 | ||
| Sat., 12/17 | V Boys Indoor Track | Qualifier #1 - Greenwich, Darien, Warde, Ludlowe, Stamford, Central, St Joe's | Home - Staples Field House [Directions] | 1:00 p.m. | |||
| Sat., 12/17 | V Wrestling | Ludlowe Invitational | Away | 9:00 a.m. | 7:30am/12:00 | ||
| Sat., 12/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners Ice Rink [Directions] | 8:30 p.m. | L 1-5 | ||
| Sat., 12/17 | V Girls Indoor Track | Bishop Laughlin games @ Queens Bridge AC | Away | 8:00 a.m. | 6am | ||
| Sat., 12/17 | V Girls Indoor Track | Qualifier #1 - Greenwich, Darien, Warde, Ludlowe, Stamford, Central, St Joe's | Home - Staples Field House [Directions] | 1:00 p.m. | |||
| Sun., 12/18 | JV Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 9:00 p.m. | Junior Varsity game | ||
| Mon., 12/19 | V Boys Basketball | Darien | Away - Trumbull H.S. [Directions] | 5:30 p.m. | L 64-71 | 4:00/8:00 | |
| Mon., 12/19 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:30-5:30pm | 2:40/5:30 | ||
| Mon., 12/19 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | TBA | 2:45/7:00 | 2 buses | |
| Mon., 12/19 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Tue., 12/20 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:30-5:30pm | 2:40/5:30 | ||
| Tue., 12/20 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Tue., 12/20 | V Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 45-39 | ||
| Tue., 12/20 | JV Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Tue., 12/20 | FR Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | |||
| Wed., 12/21 | V Boys Ice Hockey | New Fairfield | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 4-5 [Detailed Results] | ||
| Wed., 12/21 | V Boys Squash | Bronxville (NY) | Home - Chelsea Piers [Directions] | 9:00 p.m. | |||
| Wed., 12/21 | V Wrestling | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | 5:30/8:00 | ||
| Wed., 12/21 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Wed., 12/21 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 4:15 p.m. | L 4-6 | 2:15 pm | |
| Thu., 12/22 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 9:00-10:45pm | 7:00/10:45pm | ||
| Thu., 12/22 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 5:00 p.m. | 3:30/6:00 | ||
| Thu., 12/22 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Thu., 12/22 | V Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:50 p.m. | L 0-7 | ||
| Fri., 12/23 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | L 51-58 | 4:00/8:00 | |
| Fri., 12/23 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ride with varsity | ||
| Fri., 12/23 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 3:45 p.m. | 2:30/5:00 | ||
| Fri., 12/23 | V Boys Ice Hockey | Woodstock Academy | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 0-3 | ||
| Fri., 12/23 | V Girls Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 2:00 p.m. | W 46-31 | ||
| Fri., 12/23 | JV Girls Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 12:30 p.m. | |||
| Mon., 12/26 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms Rink [Directions] | 1:00 p.m. | L 4-7 | 10:00/2:00 | @ Avon Old Farms, AT Bus |
| Mon., 12/26 | JV Boys Ice Hockey | Daniel Hand | Home - Milford Ice Pavilion [Directions] | 6:15 p.m. | |||
| Tue., 12/27 | V Boys Basketball | Kolbe Cathedral | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 60-57 | ||
| Tue., 12/27 | JV Boys Ice Hockey | Lyman Hall | Home - Milford Ice Pavilion [Directions] | 2:45 p.m. | |||
| Tue., 12/27 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 8:15-10:00am | 7:00/10:00am | ||
| Tue., 12/27 | V Boys Indoor Track | Rhode Island Classic | Away | Cancelled | Cancelled | ||
| Wed., 12/28 | JV Boys Ice Hockey | Guilford | Home - Milford Ice Pavilion [Directions] | 4:30 p.m. | |||
| Wed., 12/28 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 8:15-9:30am | 7:00/10:00am | ||
| Wed., 12/28 | V Girls Basketball | Manchester | Home - Staples H.S. Gym [Directions] | 2:00 p.m. | W 49-40 | ||
| Wed., 12/28 | V Girls Gymnastics | Greenwich, Joel Barlow | Away - Greenwich YWCA [Directions] | 3:00 p.m. | 125.6 | 1:30/4:00 | |
| Thu., 12/29 | V Boys Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 62-81 | ||
| Thu., 12/29 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 8:15-9:30am | 7:00/10:00am | ||
| Thu., 12/29 | V Boys Indoor Track | Hillhouse Winter Relays | Away | 9:00 a.m. | 7:00am | ||
| Thu., 12/29 | V Wrestling | Darien, Ridgefield, Westhill | Home - Staples Field House [Directions] | 12:00 p.m. | Staples 78 Darien 3, Staples 18 Westhill 63, Staples 42 Ridgefield 39 | ||
| Thu., 12/29 | V Girls Indoor Track | 17th Marine Corps Classic @ 168th St Armory | Away | 8:00 a.m. | 6:00am | ||
| Fri., 12/30 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 8:15-9:30am | 7:00/10:00am | ||
| Mon., 1/2 | V Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | 5:00 p.m. | L 1-8 | 1:30/4:00 | @ Pomphrett School AT Bus |
| Tue., 1/3 | V Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 58-44 | ||
| Tue., 1/3 | JV Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Tue., 1/3 | FR Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Tue., 1/3 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:30pm | 2:40/5:30 | ||
| Tue., 1/3 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | TBA | 2:45/7:00 | ||
| Tue., 1/3 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Tue., 1/3 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 7:00 p.m. | L 44-57 | 4:00/8:00 | |
| Tue., 1/3 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ride with varsity | ||
| Tue., 1/3 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 3:45 p.m. | 2:15/5:00 | ED 2:00 | |
| Wed., 1/4 | V Boys Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Wed., 1/4 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:45pm | 2:40/5:30 | ||
| Wed., 1/4 | V Boys Squash | Darien | Home - Chelsea Piers [Directions] | 9:00 p.m. | |||
| Wed., 1/4 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Wed., 1/4 | V Wrestling | Trumbull | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | Trumbull 58 Staples 15 | ||
| Wed., 1/4 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Wed., 1/4 | V Girls Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Wed., 1/4 | V Girls Gymnastics | Westhill, New Canaan | Away - Westhill - New Gymnasium [Directions] | 5:30 p.m. | 120 | 3:45/6:00 | |
| Wed., 1/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 5:30 p.m. | L 2-5 | 4:30 pm | |
| Thu., 1/5 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Thu., 1/5 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 37-46 | 4:00/8:00 | |
| Thu., 1/5 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ride with varsity | ||
| Thu., 1/5 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Fri., 1/6 | V Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 73-89 | ||
| Fri., 1/6 | JV Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Fri., 1/6 | FR Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Fri., 1/6 | JV Boys Ice Hockey | East Catholic | Away - Champions Skating Center/Cromwell [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 | |
| Fri., 1/6 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 1/6 | V Boys Indoor Track | Dartmouth Relays | Away | Cancelled | Cancelled | ||
| Fri., 1/6 | V Boys Swimming and Diving | Westhill/Stamford | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Fri., 1/6 | V Girls Indoor Track | Dartmouth Relays | Away | TBA | |||
| Sat., 1/7 | V Boys Indoor Track | Qualifier #2 - Ridgefield, Warde, Trumbull, Ludlowe, Norwalk, Stamford, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 1/7 | V Boys Indoor Track | Dartmouth Relays | Away | Cancelled | Cancelled | ||
| Sat., 1/7 | V Boys Indoor Track | Dartmouth Relays | Away | Cancelled | Cancelled | ||
| Sat., 1/7 | V Wrestling | Warde Invitational | Away | 9:00 a.m. | 7:30am/12:00 | ||
| Sat., 1/7 | V Girls Gymnastics | Pomperaug Invitational @ Pomperaug | Away - Pomperaug | Cancelled | Cancelled | 8:15am | |
| Sat., 1/7 | V Girls Indoor Track | Qualifier #2 - Ridgefield, Warde, Trumbull, Ludlowe, Norwalk, Stamford, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 1/7 | V Girls Indoor Track | Dartmouth Relays | Away | TBA | |||
| Mon., 1/9 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:30-5:50pm | 2:40/5:30 | ||
| Mon., 1/9 | V Boys Swimming and Diving | Wilton | Away [Directions] | 3:40 p.m. | 2:15/5:00 | ED 2:00 | |
| Mon., 1/9 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | TBA | 2:45/7:00 | ||
| Mon., 1/9 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Mon., 1/9 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | |||
| Mon., 1/9 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Westport PAL Longshore Rink [Directions] | 6:00 p.m. | |||
| Mon., 1/9 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Westport PAL Rink Longshore [Directions] | 6:00 p.m. | Junior varsity game | ||
| Mon., 1/9 | V Girls Squash | Rye (NY) | Home - Chelsea Piers [Directions] | 8:30 p.m. | |||
| Tue., 1/10 | V Boys Basketball | Wilton | Away [Directions] | 7:00 p.m. | L 41-77 | 4:00/8:00 | |
| Tue., 1/10 | JV Boys Basketball | Wilton | Away [Directions] | 5:15 p.m. | ride with varsity | ||
| Tue., 1/10 | FR Boys Basketball | Wilton | Away [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Tue., 1/10 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:30pm | 2:40/5:30 | ||
| Tue., 1/10 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Tue., 1/10 | V Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | W 45-44 | ||
| Tue., 1/10 | JV Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | |||
| Tue., 1/10 | FR Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | Cancelled | Cancelled | ||
| Tue., 1/10 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | 4:00 p.m. | 125.95 | 2:45/5:00 | |
| Wed., 1/11 | V Boys Ice Hockey | St. Joseph | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 2-5 | ||
| Wed., 1/11 | V Wrestling | Norwalk | Away - Norwalk High Gym [Directions] | 4:30 p.m. | Norwalk 18 Staples 54 | 3:15/5:30 | |
| Wed., 1/11 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Wed., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | 6:30 p.m. | W 10- 5 | ||
| Thu., 1/12 | V Boys Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Thu., 1/12 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:30pm | 2:40/5:30 | ||
| Thu., 1/12 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | 2:00/4:30 | ED 1:45 | |
| Thu., 1/12 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Thu., 1/12 | V Girls Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Thu., 1/12 | JV Girls Ice Hockey | New Canaan | Away - Veterans Park [Directions] | 3:30 p.m. | Junior Varsity game | ||
| Fri., 1/13 | V Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 50-52 | ||
| Fri., 1/13 | JV Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Fri., 1/13 | FR Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Fri., 1/13 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 1/13 | V Boys Indoor Track | McReavy Invitational @ Wesleyan Univ | Away | Cancelled | Cancelled | 1:45 | ED 1:15 |
| Fri., 1/13 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 31-54 | 4:00/8:00 | |
| Fri., 1/13 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ride with varsity | ||
| Fri., 1/13 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 1/13 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 6:00 p.m. | L 2-8 | 2:15 pm | |
| Fri., 1/13 | V Girls Indoor Track | East Coast Classic | Away | Cancelled | Cancelled | 1:00pm/8:00 | |
| Sat., 1/14 | V Boys Ice Hockey | Darien | Home - Milford Ice Pavilion [Directions] | 1:00 p.m. | L 0-5 | ||
| Sat., 1/14 | V Boys Indoor Track | Qualifier #3 - Greenwich, Ridgefield, Danbury, MaMahon, Central, Westhill, St Joe's | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 1/14 | V Boys Indoor Track | Shoreline Coaches Invitational | Away | 9:00 a.m. | 7:00am/3:00pm | Hillhouse | |
| Sat., 1/14 | V Wrestling | Staples Duals vs. BMHS, Fairfield Prep, Weston, New Haven, Greenwich | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | Staples 62 New Haven 18, Staples 49 Weston 21, Staples 39 Fairfield Prep 42, Staples 19 Greenwich 56 | ||
| Sat., 1/14 | V Competitive Cheerleading | Hatterfest | Away | TBA | 7:15/1:00 | ||
| Sat., 1/14 | V Girls Ice Hockey | Hall/Conard | Home - Terry Conners Ice Rink [Directions] | 8:10 p.m. | L 0-7 | ||
| Sat., 1/14 | V Girls Indoor Track | Qualifier #3 - Greenwich, Ridgefield, Danbury, MaMahon, Central, Westhill, St Joe's | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 1/14 | V Girls Indoor Track | East Coast Classic | Away | Cancelled | Cancelled | 6am | |
| Mon., 1/16 | JV Boys Ice Hockey | New Fairfield | Home - Milford Ice Pavilion [Directions] | 1:00 p.m. | |||
| Mon., 1/16 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:30-5:30pm | 2:15/5:30 | ||
| Tue., 1/17 | V Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 70-47 | ||
| Tue., 1/17 | JV Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Tue., 1/17 | FR Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Tue., 1/17 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:30pm | 2:40/5:30 | ||
| Tue., 1/17 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:45 p.m. | W 60-27 | 2:30/6:30 | |
| Tue., 1/17 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ride with varsity | ||
| Wed., 1/18 | V Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | 6:00 p.m. | L 4-5 | 3:00/7:00 | @ Wesleyan College AT Bus |
| Wed., 1/18 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 | |
| Wed., 1/18 | V Wrestling | Wilton | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | Staples 34 Wilton 39 | ||
| Wed., 1/18 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 3:30 p.m. | W 2-1 | ||
| Thu., 1/19 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:30pm | 2:40/5:30 | ||
| Thu., 1/19 | V Girls Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 52-42 | ||
| Thu., 1/19 | JV Girls Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | |||
| Fri., 1/20 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 2:30 p.m. | L 71-77(OT) | 12:45/5:00 | |
| Fri., 1/20 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ride with varsity | ||
| Fri., 1/20 | JV Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | 8:10 p.m. | 5:30pm/9:00 | AT bus start at Milford Ice Pavilion got to ENfield, return to Milford, then Staples. | |
| Fri., 1/20 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 1/20 | V Boys Indoor Track | Yale Invitational | Away | 1:00 p.m. | 2 buses 11:00am and 1:00pm | ||
| Fri., 1/20 | V Boys Squash | Hopkins School | Away | 4:30 p.m. | 3:00/5:30 | ||
| Fri., 1/20 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 1/20 | V Girls Indoor Track | Yale Classic | Away | 1:00 a.m. | |||
| Fri., 1/20 | V Girls Squash | Hopkins School | Away | 4:30 p.m. | 3:00/5:30 | ||
| Sat., 1/21 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 9:00 a.m. | 7:30am/10:00 | ||
| Sat., 1/21 | V Boys Indoor Track | Qualifier #4 - Darien, Warde, New Canaan, Trumbull, Ludlowe, Norwalk, McMahon | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 1/21 | V Boys Indoor Track | Yale Invitational | Away | 9:00 a.m. | Yes | ||
| Sat., 1/21 | V Boys Indoor Track | SCC Coaches Invitational | Away | 9:00 a.m. | 7:00am | ||
| Sat., 1/21 | V Wrestling | John Chacho Duals vs. BMHS, Fairfield Prep, Masuk, Shelton, Mamaroneck, NY, Norwalk | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | Staples 45 Norwalk 36, Staples 48 Masuk 34, Staples 63 Mamaroneck 12, Staples 21 Shelton 57 | ||
| Sat., 1/21 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 10:30 a.m. | 8:45am/11:30 | ||
| Sat., 1/21 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 3:20 p.m. | L 0-7 | ||
| Sat., 1/21 | V Girls Indoor Track | Qualifier #4 - Darien, Warde, New Canaan, Trumbull, Ludlowe, Norwalk, McMahon | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 1/21 | V Girls Indoor Track | Yale Classic | Away | 9:00 a.m. | |||
| Sat., 1/21 | V Girls Indoor Track | SCC Coaches Invitational @ Floyd Little AC | Away | TBA | 12:00 | ||
| Sun., 1/22 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 6:10 p.m. | |||
| Sun., 1/22 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 7:20 p.m. | |||
| Sun., 1/22 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 7:30 p.m. | Junior Varsity game | ||
| Mon., 1/23 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Mon., 1/23 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | TBA | 2:45/7:00 | ||
| Mon., 1/23 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Tue., 1/24 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 7:00 p.m. | W 59-50 | 4:00/8:00 | |
| Tue., 1/24 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:00 p.m. | ride with varsity | ||
| Tue., 1/24 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Tue., 1/24 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Tue., 1/24 | V Girls Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | L 44-72 | ||
| Tue., 1/24 | JV Girls Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | |||
| Tue., 1/24 | V Girls Squash | St. Lukes | Away | 3:45 p.m. | 2:30/4:45 | ||
| Wed., 1/25 | V Boys Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Wed., 1/25 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | L 2-6 | 6:00/9:00 | @ Wonderland of Ice |
| Wed., 1/25 | V Boys Squash | Fairfield | Home - Chelsea Piers [Directions] | 7:00 p.m. | |||
| Wed., 1/25 | V Boys Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Wed., 1/25 | V Wrestling | Stamford | Away - Stamford High Aux Gym [Directions] | 6:00 p.m. | 4:30/7:00 | ||
| Wed., 1/25 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Wed., 1/25 | V Girls Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Wed., 1/25 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | 7:00 p.m. | L 0-7 | 4:30 pm | |
| Thu., 1/26 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Thu., 1/26 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Thu., 1/26 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | 6:30 p.m. | 124.750 | 5:30/7:30 | |
| Thu., 1/26 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | L 0-8 | 6:30 pm | |
| Fri., 1/27 | V Boys Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 48-61 | ||
| Fri., 1/27 | JV Boys Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Fri., 1/27 | FR Boys Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Fri., 1/27 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 1/27 | V Wrestling | Greens Farms Academy | Away | 6:00 p.m. | 4:30/7:00 | ||
| Fri., 1/27 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Fri., 1/27 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | W 50-30 | 3:00/6:00 | |
| Fri., 1/27 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ride with varsity | ||
| Sat., 1/28 | V Boys Ice Hockey | New Canaan | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 1-6 | ||
| Sat., 1/28 | V Boys Indoor Track | FCIAC West Division Championship | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 1/28 | V Boys Indoor Track | New Balance Indoor Grand Prix @ Lewis Center | Away | Cancelled | Cancelled | Yes | |
| Sat., 1/28 | V Wrestling | Highlander Invitational @ Portland HS | Away | 9:00 a.m. | 7:00am/12:00 | ||
| Sat., 1/28 | V Girls Gymnastics | Trumbull, Darien | Away - Next Dimension Gymnastics [Directions] | 6:00 p.m. | 121.05 | 4:30/7:00 | |
| Sat., 1/28 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 8:45 p.m. | L 1-6 | ||
| Sat., 1/28 | JV Girls Ice Hockey | Choate Rosemary Hall | Away - William C. S. Remsen Arena | 2:30 p.m. | Junior Varsity game | ||
| Sat., 1/28 | V Girls Indoor Track | FCIAC West Division Championship | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sun., 1/29 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 12:00 p.m. | |||
| Sun., 1/29 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 7:30 p.m. | |||
| Mon., 1/30 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | TBA | 2:45/7:00 | ||
| Mon., 1/30 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Mon., 1/30 | V Girls Squash | New Canaan | Home - Chelsea Piers [Directions] | 8:30 p.m. | |||
| Tue., 1/31 | JV Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | Cancelled | Cancelled | 2:00/5:20 | ED 1:45 |
| Tue., 1/31 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Tue., 1/31 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Wed., 2/1 | V Boys Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Wed., 2/1 | V Boys Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 57-54 | ||
| Wed., 2/1 | JV Boys Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Wed., 2/1 | FR Boys Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Wed., 2/1 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 6:10 p.m. | W 4-2 | 4:00/7:00 | |
| Wed., 2/1 | V Boys Squash | Rye (NY) | Home - Chelsea Piers [Directions] | 8:00 p.m. | |||
| Wed., 2/1 | V Wrestling | Brien McMahon | Home - Staples Field House [Directions] | 6:00 p.m. | |||
| Wed., 2/1 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Wed., 2/1 | V Girls Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Wed., 2/1 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 54-44 | 4:00/8:00 | |
| Wed., 2/1 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ride with varsity | ||
| Wed., 2/1 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 6:30 p.m. | L 4-5(OT) | ||
| Thu., 2/2 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championship @Hillhouse HS | Away | 4:00 p.m. | 1:45 | ED 1:15 | |
| Thu., 2/2 | V Boys Squash | St. Lukes | Away | 4:30 p.m. | 2:45/5:30 | ||
| Thu., 2/2 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Thu., 2/2 | V Girls Indoor Track | FCIAC Championship @ Hillhouse | Away | 4:00 p.m. | 1:30pm | ||
| Fri., 2/3 | V Boys Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | W 55-47 | 4:00/8:00 | |
| Fri., 2/3 | JV Boys Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | ride with varsity | ||
| Fri., 2/3 | FR Boys Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 2/3 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 2/3 | V Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 44-70 | ||
| Fri., 2/3 | JV Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Fri., 2/3 | FR Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Sat., 2/4 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | T 3-3(OT) | ||
| Sat., 2/4 | V Boys Indoor Track | FCIAC JV Invitational | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Sat., 2/4 | JV Wrestling | 2017 Southern CT JV Wrestling Championships | Away | 9:30 a.m. | 7:45am/1:00 | Fairfield Ludlowe HS | |
| Sat., 2/4 | V Competitive Cheerleading | FCIACS | Away | 9:00 a.m. | 7:15/1:00 | ||
| Sat., 2/4 | V Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 2:00 p.m. | L 0-6 | ||
| Sat., 2/4 | V Girls Indoor Track | FCIAC JV Championship | Home - Staples Field House [Directions] | 10:00 a.m. | |||
| Mon., 2/6 | V Boys Ice Hockey | Trinity Catholic | Away - Wonderland Bridgeport | 4:45 p.m. | L 6-7(OT) | 3:00/6:00 | |
| Mon., 2/6 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | TBA | 2:45/7:00 | ||
| Mon., 2/6 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Mon., 2/6 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 8:30 p.m. | W 7-4 | ||
| Mon., 2/6 | V Girls Squash | New Canaan B | Home - Chelsea Piers [Directions] | 8:30 p.m. | |||
| Tue., 2/7 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | L 38-52 | 4:00/8:00 | |
| Tue., 2/7 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ride with varsity | ||
| Tue., 2/7 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Tue., 2/7 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:00 p.m. | L 0-7 | 1:45/5:00 | ED 1:30 |
| Tue., 2/7 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Tue., 2/7 | V Wrestling | Fairfield Warde | Away - Fairfield Warde Small Gym [Directions] | 6:00 p.m. | 4:00/7:00 | ||
| Tue., 2/7 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Tue., 2/7 | V Girls Basketball | Darien | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 52-63 | ||
| Tue., 2/7 | JV Girls Basketball | Darien | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Tue., 2/7 | JV Girls Ice Hockey | New Canaan | Away - New Canaan Winter Club [Directions] | 4:15 p.m. | Junior Varsity Game | ||
| Wed., 2/8 | V Boys Squash | New Canaan | Home - Chelsea Piers [Directions] | 7:00 p.m. | |||
| Wed., 2/8 | V Boys Swimming and Diving | New Canaan | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Wed., 2/8 | V Wrestling | Practice | Home - Weston HS [Directions] | 3:00pm | 2:45/5:00 | ||
| Wed., 2/8 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Wed., 2/8 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 126.65 | 4:30/7:30 | |
| Wed., 2/8 | V Girls Ice Hockey | Branford | Home - Terry Conners Ice Rink [Directions] | 4:30 p.m. | L 0-3 | ||
| Thu., 2/9 | JV Boys Ice Hockey | Norwalk | Away [Directions] | 3:15 p.m. | 2:00/4:15 | Veterans Rink | |
| Thu., 2/9 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Thu., 2/9 | V Co-ed Squash | Practice | Home - Intensity 490 Westport Ave, Norwalk, CT 06851 [Directions] | 3:00pm | 2:15 drop only | ||
| Fri., 2/10 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 2/10 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Staples HS Pool [Directions] | 4:00 p.m. | |||
| Fri., 2/10 | V Wrestling | FCIAC Championship @ NCHS | Away | Cancelled | Cancelled | 1:30 | ED 1:15 |
| Sat., 2/11 | V Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 2:00 p.m. | W 69-55 | ||
| Sat., 2/11 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 8:50 p.m. | L 0-7 | 6:30/9:50 | |
| Sat., 2/11 | V Wrestling | FCIAC Championship @ NCHS | Away | 8:00 a.m. | 7:00am/1:00pm | ||
| Sat., 2/11 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | L 39-61 | 2:00/6:00 | |
| Sat., 2/11 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 2:30 p.m. | 12:45 pm | ||
| Sat., 2/11 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 1:00 p.m. | 11:30/2:00 | ||
| Sat., 2/11 | V Girls Gymnastics | FCIAC Championship @ Jonathan Law | Away | 10:30 a.m. | 123 | 8:30/12:30 | |
| Sat., 2/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | 8:10 p.m. | L 3-7 | ||
| Mon., 2/13 | V Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 57-50 | ||
| Mon., 2/13 | JV Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | |||
| Mon., 2/13 | FR Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 3:45 p.m. | |||
| Mon., 2/13 | JV Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 4:00 p.m. | 2:40/5:30 | Shelton Ice Rink | |
| Mon., 2/13 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Mon., 2/13 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | W 52-23 | 4:00/8:00 | |
| Mon., 2/13 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:00 p.m. | ride with varsity | ||
| Mon., 2/13 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Tue., 2/14 | V Boys Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Tue., 2/14 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Tue., 2/14 | V Wrestling | Practice | Home - Greenwich HS [Directions] | 3:00pm | 2:45 | ||
| Tue., 2/14 | V Girls Alpine Skiing | Mt Southington | Away | TBA | 1:45/7:00 | ||
| Tue., 2/14 | V Girls Gymnastics | New Milford, Pomperaug | Away - New Milford HS [Directions] | 5:00 p.m. | 128.05 | 3:15/6:00 | |
| Wed., 2/15 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | 8:15 p.m. | W 3-1 | 5:15/9:15 | @ Northford Ice Pavilion AT Bus |
| Wed., 2/15 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:30pm | ED 1:15 | |
| Wed., 2/15 | V Wrestling | Practice | Home - Wilton HS [Directions] | 3:00pm | 2:45 | ||
| Wed., 2/15 | V Girls Gymnastics | Ro Carlucci Invitational @ Westhill | Away | 5:00 p.m. | 3:45/6:30 | ||
| Wed., 2/15 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | 5:30 p.m. | L 2-4 | ||
| Wed., 2/15 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:30/8:00 | ED 1:15 | |
| Thu., 2/16 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 2/17 | JV Boys Ice Hockey | Norwalk | Away [Directions] | 3:30 p.m. | 2:00/4:30 | Veterans Rink | |
| Fri., 2/17 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 2/17 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:00 p.m. | 1:30/9:00 | ||
| Fri., 2/17 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 7:20 p.m. | L 1-9 | ||
| Sat., 2/18 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 1-2(OT) | ||
| Sat., 2/18 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | 7:00am/12:00 | ||
| Sat., 2/18 | V Competitive Cheerleading | Battle at Fairfield Univ | Away | TBA | 8:40am | ||
| Sat., 2/18 | V Girls Basketball | Trumbull | Away [Directions] | 1:45 p.m. | 12:00/2:30 | @ Norwalk | |
| Sat., 2/18 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners Ice Rink [Directions] | 8:20 p.m. | W 6-4 | ||
| Mon., 2/20 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | L 49-54 | 4:00/8:00 | |
| Mon., 2/20 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ride with varsity | ||
| Mon., 2/20 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Mon., 2/20 | V Boys Ice Hockey | North Branford | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 4-6 | ||
| Mon., 2/20 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:30pm | ||
| Mon., 2/20 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:30 | ||
| Tue., 2/21 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Wed., 2/22 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | L 57-66 | 4:00/8:00 | |
| Wed., 2/22 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ride with varsity | ||
| Wed., 2/22 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 2/22 | V Boys Ice Hockey | Norwalk | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | W 4-3 | ||
| Thu., 2/23 | JV Boys Ice Hockey | East Catholic | Home - Milford Ice Pavilion [Directions] | 4:10 p.m. | |||
| Fri., 2/24 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Fri., 2/24 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 12:45/9:00 | ||
| Sat., 2/25 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | 3:30 p.m. | W 5-3 | 1:00/4:30 | @ West Haven |
| Sat., 2/25 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | 6:45am/10:00 | ||
| Sat., 2/25 | V Girls Gymnastics | Class L Gymnastics @ Pomperaug | Away | 9:00 a.m. | 7:15am | ||
| Mon., 2/27 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Tue., 2/28 | JV Boys Ice Hockey | Norwalk | Home - Milford Ice Pavilion [Directions] | 4:10 p.m. | |||
| Tue., 2/28 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Trials @ Greenwich HS | Away | 4:30 p.m. | 2:00 | Ed 1:55 | |
| Tue., 2/28 | V Girls Basketball | Stamford | Away [Directions] | 7:00 p.m. | 5:00/8:00 | ||
| Wed., 3/1 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10-5:10pm | 2:40/5:30 | ||
| Wed., 3/1 | V Boys Swimming and Diving | FCIAC Diving Finals @ Westhill | Away | 4:30 p.m. | |||
| Thu., 3/2 | V Boys Alpine Skiing | States | Away | 3:00 p.m. | 10:45/6:30 | ||
| Thu., 3/2 | V Boys Swimming and Diving | FCIAC Finals at Greenwich | Away | 6:00 p.m. | 4:00pm | ||
| Thu., 3/2 | V Girls Alpine Skiing | States | Away | TBA | 10:45/6:30 | ||
| Fri., 3/3 | V Boys Basketball | Fairfield Warde (Scrim.) | Away [Directions] | 3:00 p.m. | 3:00/5:00 | ||
| Fri., 3/3 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 4:00 p.m. | |||
| Sat., 3/4 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | 6 am | ||
| Sat., 3/4 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 9:00 a.m. | |||
| Sat., 3/4 | V Competitive Cheerleading | States | Away | TBA | 2:30 | Floyd Little AC | |
| Sat., 3/4 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | |||
| Mon., 3/6 | V Boys Basketball | East Hartford | Away [Directions] | 6:00 p.m. | 3:15/7:00 | ||
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Hamden HS [Directions] | 5:30 p.m. | |||
| Fri., 3/10 | V Boys Indoor Track | New Balance Indoor Nationals | Away | TBA | |||
| Fri., 3/10 | V Girls Indoor Track | New Balance Indoor Nationals | Away | TBA | |||
| Sat., 3/11 | V Boys Indoor Track | New Balance Indoor Nationals | Away | TBA | |||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford HS | 3:30 p.m. | 11:00am | ||
| Sat., 3/11 | V Girls Indoor Track | New Balance Indoor Nationals | Away | TBA | |||
| Sun., 3/12 | V Boys Indoor Track | New Balance Indoor Nationals | Away | TBA | |||
| Sun., 3/12 | V Girls Indoor Track | New Balance Indoor Nationals | Away | TBA | |||
| Mon., 3/13 | Unified Sports Basketball | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | 2:30 | 2 wheelchairs plus 23 pax | |
| Tue., 3/14 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | 2:30pm | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | |||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | |||
| Tue., 3/21 | V Softball | Darien (Scrim.) | Away - DHS Baseball JV Field [Directions] | 3:30 p.m. | 2:15/5:00 | ||
| Wed., 3/22 | ALL Boys Golf | Practice | Home - The Rinks at Shelton [Directions] | 2:45pm | 2:45pm | ||
| Fri., 3/24 | ALL Boys Golf | Practice | Home - The Rinks at Shelton [Directions] | 2:45pm | 2:45pm | ||
| Fri., 3/24 | V Boys Lacrosse | Somers (NY) (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | |||
| Fri., 3/24 | V Boys Rugby | Fairfield Ludlowe/Warde | Home - Staples Stadium [Directions] | 8:00 p.m. | |||
| Fri., 3/24 | JV Boys Rugby | Fairfield Ludlowe/Warde | Home - Staples Stadium [Directions] | 6:30 p.m. | |||
| Fri., 3/24 | FR Boys Rugby | Fairfield Prep | Home - Staples Stadium [Directions] | 5:00 p.m. | |||
| Sat., 3/25 | V Boys Lacrosse | Cheshire (Scrim.) | Home - Staples Stadium [Directions] | 12:30 p.m. | |||
| Sat., 3/25 | V Girls Lacrosse | Wilton (Scrim.) | Away [Directions] | 9:10 a.m. | 7:30am/12:00 | ||
| Sat., 3/25 | V Softball | New Milford (Scrim.) | Away - Danbury Sports Dome [Directions] | 4:00 p.m. | 2:15/6:00 | ||
| Tue., 3/28 | V Baseball | Windsor (Scrim.) | Away [Directions] | 3:30 p.m. | Yes | ED 1:45 | |
| Tue., 3/28 | V Boys Lacrosse | Fairfield Ludlowe (Scrim.) | Away - Taft Field [Directions] | 5:00 p.m. | 3:30/6:00 | ||
| Tue., 3/28 | JV Boys Lacrosse | Fairfield Ludlowe (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Tue., 3/28 | V Girls Lacrosse | Greens Farms Academy (Scrim.) | Away | 3:45 p.m. | 2:30pm/5:00pm | ||
| Wed., 3/29 | V/JV Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45pm | 2:45pm | ||
| Wed., 3/29 | V Co-ed Sailing | STAM, DHS | Home - Cedar Point Yacht Club [Directions] | 3:00 p.m. | Yes | ||
| Thu., 3/30 | V Baseball | East Catholic (Scrim.) | Away [Directions] | 3:30 p.m. | 2:00 | Sportsplex N Branford | |
| Thu., 3/30 | V/JV Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45pm | 2:45pm | ||
| Thu., 3/30 | V Boys Volleyball | Fairfield Warde (Scrim.) | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Thu., 3/30 | V Co-ed Sailing | Practice | Home - Greenwich Academy [Directions] | 3:45 | 2:20/5:00 | ||
| Thu., 3/30 | V Girls Lacrosse | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 4:45 p.m. | 2:30/5:00 | ||
| Thu., 3/30 | V Softball | Westhill (Scrim.) | Away [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 3/31 | V Boys Rugby | Fairfield Prep | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Sat., 4/1 | V Boys Lacrosse | Bronxville (NY) | Home - Staples Stadium [Directions] | 11:00 a.m. | L 12-6 | ||
| Sat., 4/1 | JV Boys Lacrosse | Bronxville (NY) | Home - Staples Stadium [Directions] | 1:00 p.m. | |||
| Sat., 4/1 | FR Boys Lacrosse | Hopkins School (Scrim.) | Away | 11:00 a.m. | 9:00am/12:00 | ||
| Sat., 4/1 | V Girls Lacrosse | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 10:00 a.m. | W 17-5 | ||
| Sat., 4/1 | JV Girls Lacrosse | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 11:30 a.m. | |||
| Mon., 4/3 | V/JV Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:20pm | 2:20pm | ||
| Mon., 4/3 | JV Boys Rugby | Fairfield Prep | Away [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Mon., 4/3 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | W 7-0 | 2:30/4:15 | |
| Mon., 4/3 | V Girls Outdoor Track | New Canaan | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Mon., 4/3 | V Softball | Masuk | Away - Masuk HS Softball Field [Directions] | 4:15 p.m. | L 2-3 | 2:30/5:00 | |
| Mon., 4/3 | V Girls Tennis | Trinity Catholic | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Tue., 4/4 | V Boys Lacrosse | Danbury | Home - Staples Stadium [Directions] | 5:30 p.m. | W 17-1 | ||
| Tue., 4/4 | JV Boys Lacrosse | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Tue., 4/4 | JV Boys Tennis | Wilton | Home - Town Farms Tennis Courts [Directions] | Cancelled | Cancelled | ||
| Tue., 4/4 | V Girls Lacrosse | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 18-4 | ||
| Tue., 4/4 | JV Girls Tennis | Wilton | Away [Directions] | Cancelled | Cancelled | 2:45/5:00 | |
| Wed., 4/5 | V/JV Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45pm | 2:45pm | ||
| Wed., 4/5 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 4/5 | V Boys Tennis | Danbury | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Wed., 4/5 | V Boys Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Wed., 4/5 | JV Boys Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Wed., 4/5 | V Co-ed Sailing | GA, FLHS | Home - Cedar Point Yacht Club [Directions] | 3:00 p.m. | |||
| Wed., 4/5 | V Girls Lacrosse | Greens Farms Academy (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 3:45 p.m. | |||
| Wed., 4/5 | JV Girls Lacrosse | Greens Farms Academy (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | TBA | |||
| Wed., 4/5 | FR Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | |||
| Thu., 4/6 | V Co-ed Sailing | BS, GFA, RHS | Away | Cancelled | Cancelled | 2:20 | |
| Thu., 4/6 | V Girls Water Polo | Greenwich | Away [Directions] | 3:00 p.m. | 1:45/5:00 | ED 1:30 | |
| Thu., 4/6 | JV Girls Water Polo | Greenwich | Away [Directions] | 3:00 p.m. | ED 1:30 | ||
| Fri., 4/7 | V Boys Rugby | Hudson Catholic School NJ | Home - Staples Stadium [Directions] | 5:00 p.m. | |||
| Fri., 4/7 | JV Boys Rugby | Hudson Catholic School NJ | Home - Staples Stadium [Directions] | 6:30 p.m. | |||
| Fri., 4/7 | V Boys Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Fri., 4/7 | JV Boys Tennis | Fairfield Warde | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Fri., 4/7 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | 2:30/6:00 | |
| Fri., 4/7 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ride with varsity | ||
| Fri., 4/7 | V Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | W 12-11 | 3:30/7:00 | |
| Fri., 4/7 | JV Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 4/7 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 4/7 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Fri., 4/7 | V Girls Water Polo | Choate Rosemary Hall | Home - Staples HS Pool [Directions] | 3:30 p.m. | |||
| Sat., 4/8 | V Baseball | Newtown | Home - Staples HS Baseball Field [Directions] | 3:00 p.m. | L 0-3 | ||
| Sat., 4/8 | JV Baseball | Amity | Home - Wakeman Field [Directions] | 10:30 a.m. | |||
| Sat., 4/8 | JV Baseball | Newtown | Home - Wakeman Field [Directions] | 3:00 p.m. | |||
| Sat., 4/8 | FR Baseball | Amity | Away - John Janenda Baseball Field @ Amity HS [Directions] | 1:00 p.m. | 11:00/2:30 | ||
| Sat., 4/8 | FR Boys Rugby | Xavier | Away [Directions] | Cancelled | Cancelled | ||
| Sat., 4/8 | V Girls Outdoor Track | Bloomfield Invitational | Away | 8:00 a.m. | 7:00am/5:00pm | ||
| Sat., 4/8 | V Girls Tennis | Joel Barlow | Away - Tennis Courts [Directions] | 2:00 p.m. | W 7-0 | 12:30/3:00 | |
| Mon., 4/10 | V Baseball | Trinity Catholic | Home - Staples HS Baseball Field [Directions] | 1:00 p.m. | W 7-0 | ||
| Mon., 4/10 | JV Baseball | Trinity Catholic | Away - Rippowam | 1:00 p.m. | 11:30/3:00 | ||
| Mon., 4/10 | FR Baseball | Trinity Catholic | Home - Wakeman Field [Directions] | 1:00 p.m. | |||
| Mon., 4/10 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 2:00 p.m. | W 7-0 | 1:00 | |
| Mon., 4/10 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 2:00 p.m. | Share with varsity | ||
| Mon., 4/10 | V Boys Volleyball | Southington | Away - West Gym [Directions] | 1:00 p.m. | W 3-0 | ||
| Mon., 4/10 | JV Boys Volleyball | Southington | Away - West Gym [Directions] | 12:00 p.m. | |||
| Mon., 4/10 | V Softball | Trinity Catholic | Home - Wakeman Field [Directions] | 1:00 p.m. | W 8-1 | ||
| Mon., 4/10 | JV Softball | Trinity Catholic | Home - Staples HS - Softball Field [Directions] | 1:00 p.m. | |||
| Mon., 4/10 | V Girls Tennis | Wilton | Home - Staples HS-Tennis Courts [Directions] | 12:00 p.m. | W 6-1 | ||
| Tue., 4/11 | V Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 1:00 p.m. | L 0-10 | 11:30/2:30 | |
| Tue., 4/11 | V Boys Lacrosse | Trinity Catholic | Away - Trinity Gaglio Field | 4:00 p.m. | W 18-1 | 2:30/5:00 | |
| Tue., 4/11 | JV Boys Lacrosse | Trinity Catholic | Away | Cancelled | Cancelled | Yes | |
| Tue., 4/11 | FR Boys Lacrosse | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Tue., 4/11 | V Boys Tennis | Fairfield Prep | Home - Staples HS-Tennis Courts [Directions] | 12:00 p.m. | W 7-0 | ||
| Tue., 4/11 | V Girls Lacrosse | Westhill | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 18-6 | ||
| Tue., 4/11 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | 12:00 p.m. | L 3-8 | 10:30/1:30 | |
| Tue., 4/11 | V Girls Tennis | Norwalk | Home - Staples HS-Tennis Courts [Directions] | 10:00 a.m. | W 7-0 | ||
| Wed., 4/12 | V Baseball | Danbury | Home - Staples HS Baseball Field [Directions] | 1:00 p.m. | W 7-6 | ||
| Wed., 4/12 | JV Baseball | Danbury | Home - Wakeman Field [Directions] | 1:00 p.m. | |||
| Wed., 4/12 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 11:00 a.m. | 9:15/12:00 | ||
| Wed., 4/12 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 11:00 a.m. | W 5-2 | 9:15/12:00 | |
| Wed., 4/12 | JV Softball | Danbury | Away - Hatters Park Softball Fields [Directions] | 11:00 a.m. | |||
| Thu., 4/13 | V Baseball | Fairfield Warde | Home - Staples HS Baseball Field [Directions] | 1:00 p.m. | W 4-3 | ||
| Thu., 4/13 | JV Baseball | Fairfield Warde | Home - Wakeman Field [Directions] | 1:00 p.m. | |||
| Thu., 4/13 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Thu., 4/13 | V Boys Lacrosse | Kellenberg Memorial (NY) | Away | 11:00 a.m. | W 7-5 | 7:30/12:00 | 1400 Glenn Curtiss Blvd; Uniondale, NY |
| Thu., 4/13 | JV Boys Lacrosse | Kellenberg Memorial | Away | 11:00 a.m. | 7:30am | ||
| Thu., 4/13 | FR Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | 8:00/11:00 | ||
| Thu., 4/13 | V Girls Lacrosse | Darien | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 8-19 | ||
| Thu., 4/13 | JV Girls Lacrosse | Darien | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Thu., 4/13 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | L 0-3 | 2:30/5:00 | |
| Sat., 4/15 | V Baseball | Amity | Away - John Janenda Baseball Field @ Amity HS [Directions] | 2:00 p.m. | L 0-4 | 11:45/4:00 | |
| Sat., 4/15 | V Boys Lacrosse | Newtown | Home - Staples Stadium [Directions] | 1:00 p.m. | W 8 - 2 | ||
| Sat., 4/15 | JV Boys Lacrosse | Newtown | Home - Staples Stadium [Directions] | 3:00 p.m. | |||
| Sat., 4/15 | V Girls Outdoor Track | Hillhouse FR/SO Invitational | Away | 10:00 a.m. | 8:00am | ||
| Mon., 4/17 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:30 p.m. | L 1-5 | 3:15/6:00 | |
| Mon., 4/17 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:30 p.m. | 3:15/5:00 | ||
| Mon., 4/17 | FR Baseball | Wilton | Home - Staples HS Baseball Field [Directions] | 4:30 p.m. | |||
| Mon., 4/17 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | Staples - 172 Wilton - 179 | 2:20/5:00 | |
| Mon., 4/17 | JV Boys Golf | Wilton | Away [Directions] | TBA | |||
| Mon., 4/17 | FR Boys Lacrosse | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Mon., 4/17 | V Boys Tennis | Trumbull | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Mon., 4/17 | V Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Mon., 4/17 | JV Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Mon., 4/17 | V Girls Outdoor Track | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2:00 | ||
| Mon., 4/17 | V Softball | Wilton | Home - Wakeman Field [Directions] | 4:30 p.m. | L 4-10 | ||
| Mon., 4/17 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Tue., 4/18 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 6 - 7 | 2:00/5:00 | ED 1:45 |
| Tue., 4/18 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 | |
| Tue., 4/18 | V Boys Outdoor Track | Darien | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Tue., 4/18 | V Boys Tennis | Bridgeport Central | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Tue., 4/18 | V Co-ed Sailing | Stamford and Darien | Home [Directions] | 4:00 p.m. | |||
| Tue., 4/18 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:00 p.m. | Staples 191 Ridgefield 197 | 2:00/5:00 | ED 1:45 |
| Tue., 4/18 | JV Girls Golf | Ridgefield | Away [Directions] | 3:00 p.m. | |||
| Tue., 4/18 | V Girls Lacrosse | St. Joseph | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 18-4 | ||
| Tue., 4/18 | JV Girls Lacrosse | St. Joseph | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Tue., 4/18 | JV Softball | Wilton | Home - Staples HS - Softball Field [Directions] | 4:30 p.m. | |||
| Tue., 4/18 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Tue., 4/18 | JV Girls Tennis | Wilton | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Wed., 4/19 | V Baseball | Trumbull | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 9-3 | ||
| Wed., 4/19 | JV Baseball | Trumbull | Home - Wakeman Field [Directions] | 4:00 p.m. | |||
| Wed., 4/19 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Wed., 4/19 | V Boys Golf | St. Joseph | Away [Directions] | 3:15 p.m. | Staples - 165 St. Joes - 177 | 2:30/5:00 | |
| Wed., 4/19 | JV Boys Golf | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | 3:15 p.m. | 2:30 | ||
| Wed., 4/19 | FR Boys Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 4/19 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | L 0-3 | 2:30/6:00 | |
| Wed., 4/19 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | ||
| Wed., 4/19 | V Co-ed Sailing | Prep and Greenwich | Away | 4:00 p.m. | 2:20/4:30 | Grass Island | |
| Wed., 4/19 | FR Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | |||
| Wed., 4/19 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:15 p.m. | L 1-13 | 2:45/5:00 | |
| Wed., 4/19 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | |||
| Thu., 4/20 | V Boys Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | Staples - 147 Warde - 182 | ||
| Thu., 4/20 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Cancelled | Cancelled | ||
| Thu., 4/20 | V Boys Lacrosse | Fox Lane (NY) | Away | 5:00 p.m. | W 13-8 | 3:00/6:00 | |
| Thu., 4/20 | JV Boys Lacrosse | Fox Lane (NY) | Away | 5:00 p.m. | 3:00/6:00 | ||
| Thu., 4/20 | V Boys Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | 2:30/6:00 2 buses | ||
| Thu., 4/20 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | 2:00/5:00 | |
| Thu., 4/20 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | 2:45/5:30 | ||
| Thu., 4/20 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | Staples 198 Greenwich 186 | 2:00/5:30 | ED 1:45 |
| Thu., 4/20 | JV Girls Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | |||
| Thu., 4/20 | V Girls Lacrosse | Conard | Away - Conard HS Stadium [Directions] | 4:00 p.m. | L 11-12 | 2:00/5:00 | ED 1:45 |
| Thu., 4/20 | JV Girls Lacrosse | Conard | Away - Conard HS North Field [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 | |
| Thu., 4/20 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Thu., 4/20 | V Girls Tennis | Greenwich | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Thu., 4/20 | JV Girls Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Fri., 4/21 | V Boys Rugby | Ridgefield | Away [Directions] | 4:30 p.m. | 2:30PM/6:00 | ||
| Fri., 4/21 | JV Boys Rugby | Ridgefield | Away [Directions] | 6:00 p.m. | |||
| Fri., 4/21 | V Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Fri., 4/21 | JV Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Sat., 4/22 | V Baseball | Bridgeport Central | Home - Staples HS Baseball Field [Directions] | 11:00 a.m. | W 23-1 | ||
| Sat., 4/22 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 12:00 p.m. | W 12-5 | 10:30/1:00 | |
| Sat., 4/22 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 2:00 p.m. | 2:30/5:00 | ||
| Sat., 4/22 | FR Boys Lacrosse | St. Anthonys (NY) | Away | 11:00 a.m. | 8:00am | 275 Wolf Hill Rd Huntington Station, NY 11747 | |
| Sat., 4/22 | FR Boys Rugby | Fordham Prep (NY) | Home - Staples Stadium [Directions] | 10:00 a.m. | |||
| Sat., 4/22 | V Co-ed Sailing | O'Day Qualifier | Away | 9:00 a.m. | 6:20am | Hotchkiss School 10 pax | |
| Sat., 4/22 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 12:00 p.m. | L 9-10 | 10:30/1:00 | Shuttle with JV |
| Sat., 4/22 | JV Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 10:30 a.m. | 9:00am/11:30am | ||
| Sat., 4/22 | V Girls Outdoor Track | 12th Annual Viking Invitational | Away | 8:00 a.m. | |||
| Sat., 4/22 | V Girls Water Polo | Hotchkiss | Home - Staples HS Pool [Directions] | 3:00 p.m. | |||
| Sun., 4/23 | V Co-ed Sailing | O'Day Qualifier | Away | 9:00 a.m. | 6:20am | Connecticut College 10 pax | |
| Mon., 4/24 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | W 14-2 | 2:45/5:00 | |
| Mon., 4/24 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Mon., 4/24 | FR Baseball | Greenwich | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | |||
| Mon., 4/24 | V Boys Golf | Westhill | Home - Longshore [Directions] | 3:00 p.m. | Staples - 151 Westhill - 179 | ||
| Mon., 4/24 | FR Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | 2:30/5:00 | ||
| Mon., 4/24 | V Boys Tennis | Norwalk | Home - Staples HS [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Mon., 4/24 | V Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Mon., 4/24 | JV Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Mon., 4/24 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:30 p.m. | Staples 194 Danbury 216 | 2:00/5:00 | ED 1:45 |
| Mon., 4/24 | V Girls Outdoor Track | Trumbull, Danbury | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30/6:00 | ||
| Mon., 4/24 | V Softball | Greenwich | Home - Wakeman Field [Directions] | 4:00 p.m. | W 8-1 | ||
| Mon., 4/24 | JV Softball | Greenwich | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | |||
| Tue., 4/25 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | L 8-16 | 2:30/5:00 | |
| Wed., 4/26 | V Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | L 0-1 | 2:45/5:00 | |
| Wed., 4/26 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | 3:15 p.m. | Staples - 165 Trinity - 203 | 2:20/5:00 | ED 2:05 |
| Wed., 4/26 | V Boys Lacrosse | New Canaan | Home - Staples Stadium [Directions] | 5:30 p.m. | L 14-15 DOT | ||
| Wed., 4/26 | JV Boys Lacrosse | New Canaan | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Wed., 4/26 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | W 3-0 | 2:30/6:00 | |
| Wed., 4/26 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ride with varsity | ||
| Wed., 4/26 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | 2:10/5:00 | ED 2:00 | |
| Wed., 4/26 | FR Girls Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 3:30 p.m. | 1:45/4:30 | ED 1:30 | |
| Wed., 4/26 | V Girls Tennis | Glastonbury | Away - East Hartford Tennis Club [Directions] | 3:45 p.m. | W 5-2 | 1:30/5:00 | ED 1:15 |
| Thu., 4/27 | JV Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 3:30 p.m. | 2:45/5:00 | ||
| Thu., 4/27 | V Boys Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | Staples-145 Danbury-169 | ||
| Thu., 4/27 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:00 p.m. | Yes | BROOKLAWN CC | |
| Thu., 4/27 | V Boys Rugby | Simsbury | Home - Staples Stadium [Directions] | 5:00 p.m. | |||
| Thu., 4/27 | JV Boys Rugby | Simsbury | Home - Staples Stadium [Directions] | 6:30 p.m. | |||
| Thu., 4/27 | V Boys Tennis | Westhill | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Thu., 4/27 | V Co-ed Sailing | FLHS, GA | Away | 3:00 p.m. | Yes | Pequote Yacht Club | |
| Thu., 4/27 | JV Girls Golf | Greenwich | Away [Directions] | Cancelled | Cancelled | ||
| Thu., 4/27 | V Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 4:00 p.m. | W 16-5 | 2:30/5:00 | |
| Thu., 4/27 | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:00 p.m. | |||
| Thu., 4/27 | V Girls Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 3:00 p.m. | |||
| Thu., 4/27 | JV Girls Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 3:00 p.m. | |||
| Fri., 4/28 | V Baseball | Brien McMahon | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 13-3 | ||
| Fri., 4/28 | JV Baseball | Brien McMahon | Home - Wakeman Field [Directions] | 4:00 p.m. | |||
| Fri., 4/28 | FR Boys Lacrosse | Don Bosco Tournament | Away | 6:30 p.m. | 4:00 AT bus | 492 Franklin Turnpike, Ramsey, NJ 07446 | |
| Fri., 4/28 | V Boys Outdoor Track | Dan O'Grady Relays | Away | 4:00 p.m. | 3:30 | ED 1:30 | |
| Fri., 4/28 | V Boys Tennis | Brien McMahon | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Fri., 4/28 | V Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Fri., 4/28 | JV Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Fri., 4/28 | V Girls Lacrosse | Rye (NY) | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | W 17-5 | ||
| Fri., 4/28 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away | 5:00 p.m. | ride with boys | ||
| Fri., 4/28 | V Softball | Brien McMahon | Away - Wakeman Field C [Directions] | 4:00 p.m. | W 17-3 | ||
| Fri., 4/28 | JV Softball | Brien McMahon | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | |||
| Fri., 4/28 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Fri., 4/28 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | 4:00 p.m. | 2:30/4:30 | ||
| Sat., 4/29 | FR Baseball | Norwalk | Home - Staples HS - Baseball Field [Directions] | 10:00 a.m. | |||
| Sat., 4/29 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | L 9 - 10 | 2:30/5:00 | |
| Sat., 4/29 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Sat., 4/29 | FR Boys Lacrosse | Don Bosco Tournament | Away | 2:30 p.m. | 12:00 AT bus | ||
| Sat., 4/29 | V Boys Outdoor Track | Dan O'Grady Relays | Away | 9:00 a.m. | 7:00am | ||
| Sat., 4/29 | V Co-ed Sailing | CT States | Away | 8:30 a.m. | 7:45am | US Coast Guard Academy | |
| Sat., 4/29 | V Co-ed Sailing | Herreshoff Qualifier | Away | 8:30 a.m. | US Coast Guard Academy | ||
| Sat., 4/29 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | W 17-5 | 4:00/6:30 | |
| Sat., 4/29 | JV Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Sat., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away | 8:00 a.m. | 6:00am | Danbury | |
| Sat., 4/29 | V Softball | Norwalk | Home - Wakeman Field [Directions] | 4:00 p.m. | L 3-10 | ||
| Sat., 4/29 | V Girls Water Polo | Suffield and Williston @ Suffield | Away | 3:00 p.m. | 12:30 | ||
| Sun., 4/30 | V Co-ed Sailing | Herreshoff Qualifier | Away | 8:30 a.m. | Yes | SailMaine and Tabor | |
| Mon., 5/1 | V Baseball | Westhill | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | L 6-8 | ||
| Mon., 5/1 | JV Baseball | Westhill | Home - Wakeman Field [Directions] | 4:00 p.m. | |||
| Mon., 5/1 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Mon., 5/1 | V Boys Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | Staples-151 Ridgefield 162 | ||
| Mon., 5/1 | JV Boys Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | |||
| Mon., 5/1 | FR Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:30 p.m. | 2:30/5:00 | ||
| Mon., 5/1 | V Boys Tennis | Stamford | Away [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Mon., 5/1 | V Co-ed Sailing | Brunswick | Away | 3:00 p.m. | 2:20 | ||
| Mon., 5/1 | FR Girls Lacrosse | Darien | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | |||
| Mon., 5/1 | V Girls Outdoor Track | Bridgeport Central, Westhill | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Mon., 5/1 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | L 3-9 | 2:30/5:00 | |
| Mon., 5/1 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | |||
| Mon., 5/1 | V Girls Tennis | Stamford | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Tue., 5/2 | V Baseball | Harding | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 18-5 | ||
| Tue., 5/2 | V Boys Lacrosse | Darien | Home - Staples Stadium [Directions] | 5:30 p.m. | L 19-4 | ||
| Tue., 5/2 | JV Boys Lacrosse | Darien | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Tue., 5/2 | V Boys Outdoor Track | Westhill, Bridgeport Central | Away - Westhill Football Field [Directions] | 4:00 p.m. | |||
| Tue., 5/2 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | ||
| Tue., 5/2 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | |||
| Tue., 5/2 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Staples 187, Trumbull 191 | 2:05/5:15 | ED 2:00 |
| Tue., 5/2 | JV Girls Golf | Trumbull | Away [Directions] | 3:30 p.m. | ED 2:00 | ||
| Tue., 5/2 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 6:00 p.m. | W 13-7 | 4:30/7:00 | shuttle with JV |
| Tue., 5/2 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | 2:30 | shuttle with varsity | |
| Tue., 5/2 | FR Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | |||
| Tue., 5/2 | V Softball | Ridgefield | Home - Wakeman Field [Directions] | 4:30 p.m. | L 2-3 | ||
| Tue., 5/2 | JV Softball | Ridgefield | Home - Staples HS - Softball Field [Directions] | 4:30 p.m. | |||
| Tue., 5/2 | JV Girls Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Wed., 5/3 | V Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 18-0 | 2:45/5:00 | |
| Wed., 5/3 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Wed., 5/3 | FR Baseball | Stamford | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | |||
| Wed., 5/3 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Staples - 162 Ludlowe - 169 | 2:30/5:00 | |
| Wed., 5/3 | V Boys Outdoor Track | Danbury, Trumbull | Home - Staples H.S. [Directions] | 4:00 p.m. | |||
| Wed., 5/3 | V Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 0-3 | ||
| Wed., 5/3 | JV Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Wed., 5/3 | V Co-ed Sailing | BS, GFA | Home - Cedar Point Yacht Club [Directions] | 3:00 p.m. | |||
| Wed., 5/3 | JV Girls Golf | Fairfield Ludlowe, Fairfield Warde | Away - South Pine Creek- Par 3 [Directions] | 3:15 p.m. | 2:10/5:00 | Par 3, ED 2:00 | |
| Wed., 5/3 | V Softball | Stamford | Home - Wakeman Field [Directions] | 4:00 p.m. | L 1-14 | ||
| Wed., 5/3 | JV Softball | Stamford | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | |||
| Wed., 5/3 | V Girls Tennis | Westhill | Away [Directions] | 4:00 p.m. | W 6-1 | 2:30/5:00 | |
| Wed., 5/3 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Thu., 5/4 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | L 3-4 | 2:45/5:00 | |
| Thu., 5/4 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Thu., 5/4 | FR Baseball | Darien | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | |||
| Thu., 5/4 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | 2:20 | New Canaan Country Club | |
| Thu., 5/4 | V Boys Lacrosse | St. Joseph | Home - Staples Stadium [Directions] | 7:00 p.m. | W 12-5 | ||
| Thu., 5/4 | JV Boys Lacrosse | St. Joseph | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | |||
| Thu., 5/4 | V Boys Tennis | Ridgefield | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Thu., 5/4 | JV Boys Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Thu., 5/4 | V Co-ed Sailing | Stam, DHS | Away | 3:00 p.m. | Yes | Stamford Yacht Club | |
| Thu., 5/4 | V Girls Golf | Wilton, Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | Staples 183, Wilton 211 | ED 2:00 | |
| Thu., 5/4 | V Girls Lacrosse | Stamford | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | W 17-6 | ||
| Thu., 5/4 | JV Girls Lacrosse | Stamford | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Thu., 5/4 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | 2:00/5:00 | ED 1:45 |
| Thu., 5/4 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 5/5 | V Boys Outdoor Track | Middletown Invitational (FR & Soph) | Away | Cancelled | Cancelled | 1:30 | ED 1:00 |
| Fri., 5/5 | V Boys Outdoor Track | Irv Black Invitational | Away | Cancelled | Cancelled | 1:30 | ED 1:00 |
| Fri., 5/5 | V Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 5:00 p.m. | |||
| Fri., 5/5 | JV Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 6:30 p.m. | |||
| Fri., 5/5 | FR Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 3:30 p.m. | |||
| Fri., 5/5 | V Girls Outdoor Track | Middletown Invitational | Away | Cancelled | Cancelled | 12:30 | ED |
| Fri., 5/5 | V Girls Water Polo | Loomis Chaffee School | Away | 4:30 p.m. | 2:30/5:30 | ||
| Sat., 5/6 | V Boys Lacrosse | Stamford | Home - Staples Stadium [Directions] | 1:00 p.m. | W 19-2 | ||
| Sat., 5/6 | JV Boys Lacrosse | Stamford | Home - Staples Stadium [Directions] | 3:30 p.m. | |||
| Sat., 5/6 | FR Boys Lacrosse | Don Bosco Tournament | Away | TBA | 8:30am | ||
| Sat., 5/6 | V Boys Outdoor Track | Irv Black Invitational | Away | Cancelled | Cancelled | 8:00am | |
| Sat., 5/6 | V Boys Outdoor Track | Middletown Invitational (varsity) | Away | 1:00 p.m. | |||
| Sat., 5/6 | V Co-ed Sailing | NESSA Women's Championship (Herreshoff Regatta) Day 1 | Away | 2:00 p.m. | Edgewood Yacht Club Cranston RI | ||
| Sat., 5/6 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 3:00 p.m. | W 11-10 | 1:30 | Shuttle with JV |
| Sat., 5/6 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:30 p.m. | 3:00/5:30 | shuttle with varsity | |
| Sat., 5/6 | V Girls Outdoor Track | Middletown Invitational | Away | 1:00 p.m. | 10:30 | ||
| Sat., 5/6 | V Girls Tennis | Darien | Home - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | W 4-3 | ||
| Sat., 5/6 | V Girls Water Polo | Hopkins School | Home - Staples HS Pool [Directions] | 3:00 p.m. | |||
| Sun., 5/7 | V Co-ed Sailing | NESSA Women's Championship (Herreshoff Regatta) Day 2 | Away | 9:15 a.m. | |||
| Sun., 5/7 | V Softball | Darien | Home - Wakeman Field [Directions] | 1:00 p.m. | L 0-6 | ||
| Mon., 5/8 | V Baseball | Ridgefield | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 2-1 | ||
| Mon., 5/8 | JV Baseball | Ridgefield | Home - Wakeman Field [Directions] | 4:00 p.m. | |||
| Mon., 5/8 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Mon., 5/8 | V Boys Golf | Norwich Free Academy Wildcat Tournament | Away | 12:00 p.m. | Staples Front - 167 | 9:30/4:00 | ED 9:15 |
| Mon., 5/8 | JV Boys Golf | Ridgefield | Away [Directions] | TBA | 1:40 | ED 1:25 Ridgefield Golf Course | |
| Mon., 5/8 | FR Boys Lacrosse | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | |||
| Mon., 5/8 | V Boys Tennis | New Canaan | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | ||
| Mon., 5/8 | JV Boys Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Mon., 5/8 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | W 3-1 | 2:00/6:00 | ED 1:45 |
| Mon., 5/8 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ride with varsity | ED 1:45 | |
| Mon., 5/8 | V Girls Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | Staples 207, Danbury 223 | ED 2:00 | |
| Mon., 5/8 | JV Girls Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | |||
| Mon., 5/8 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | 2:30/5:00 | ||
| Mon., 5/8 | V Girls Outdoor Track | Stamford, Ridgefield | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Mon., 5/8 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | L 3-5 | 2:30/5:00 | |
| Mon., 5/8 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | |||
| Mon., 5/8 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Tue., 5/9 | V Boys Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | Staples - 155 New Canaan - 155 | ||
| Tue., 5/9 | JV Boys Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | |||
| Tue., 5/9 | V Boys Lacrosse | Westhill | Away - Westhill Football Field [Directions] | 5:30 p.m. | W 18-1 | 3:45/6:30 | |
| Tue., 5/9 | JV Boys Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 3:45 p.m. | 2:30/5:00 | ||
| Tue., 5/9 | FR Boys Lacrosse | Stamford | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | |||
| Tue., 5/9 | V Boys Outdoor Track | Stamford, Ridgefield | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Tue., 5/9 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | Staples 201, New Canaan 179 | 2:30/5:00 | |
| Tue., 5/9 | JV Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | ED 1:45 | ||
| Tue., 5/9 | FR Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | |||
| Tue., 5/9 | JV Girls Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Wed., 5/10 | V Baseball | New Canaan | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 5-2 | ||
| Wed., 5/10 | JV Baseball | New Canaan | Home - Wakeman Field [Directions] | 4:00 p.m. | |||
| Wed., 5/10 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Wed., 5/10 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Staples - 152 Norwalk - 196 | 2:30/5:00 | |
| Wed., 5/10 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 5/10 | V Boys Rugby | Fairfield Ludlowe/Warde | Away | 7:00 p.m. | 5:15/8:00 | @ Warde | |
| Wed., 5/10 | JV Boys Rugby | Fairfield Ludlowe/Warde | Away | TBA | |||
| Wed., 5/10 | V Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | 2:30/4:30 | |
| Wed., 5/10 | V Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | L 0-3 | ||
| Wed., 5/10 | JV Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Wed., 5/10 | V Co-ed Sailing | GHS, Prep, RHS | Away | 3:00 p.m. | 2:20 | ||
| Wed., 5/10 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | L 3-5 | 2:30/5:00 | |
| Wed., 5/10 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | |||
| Wed., 5/10 | V Girls Tennis | Weston | Home - Staples HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | ||
| Wed., 5/10 | V Girls Water Polo | Choate Rosemary Hall | Away | 3:30 p.m. | 1:45 | ED 1:30 | |
| Thu., 5/11 | JV Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2:30pm/5:00pm | ||
| Thu., 5/11 | V Boys Outdoor Track | Loucks Games | Away | Cancelled | Cancelled | ||
| Thu., 5/11 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Thu., 5/11 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | |||
| Thu., 5/11 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-0 | 2:30/6:00 | |
| Thu., 5/11 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ride with varsity | ||
| Thu., 5/11 | V Co-ed Sailing | BS, GFA | Away | 3:30 p.m. | 2:20 | ||
| Thu., 5/11 | V Girls Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | Staples 191, Greenwich 177 | ED 2:00 | |
| Thu., 5/11 | JV Girls Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | |||
| Thu., 5/11 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 10-15 | 2:00/5:00 | ED 1:45 |
| Thu., 5/11 | JV Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | 3:30/6:30 | ||
| Thu., 5/11 | FR Girls Lacrosse | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | |||
| Thu., 5/11 | V Girls Tennis | Fairfield Ludlowe | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Thu., 5/11 | JV Girls Tennis | Fairfield Ludlowe | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Fri., 5/12 | V Boys Outdoor Track | Loucks Games | Away | Cancelled | Cancelled | ||
| Fri., 5/12 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | W 3-1 | 2:30/6:00 | |
| Fri., 5/12 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | ride with varsity | ||
| Fri., 5/12 | V Co-ed Sailing | ISSA Mallory Doublehanded Championship | Away | TBA | MIT | ||
| Fri., 5/12 | V Girls Outdoor Track | Loucks Games | Away | 3:00 p.m. | 1:00pm | White Plains HS | |
| Sat., 5/13 | V Boys Lacrosse | St. Anthonys (NY) | Away | 10:00 a.m. | W Forfeit | 7:15am | |
| Sat., 5/13 | JV Boys Lacrosse | St. Anthonys (NY) | Away | 10:00 a.m. | 7:15am | ||
| Sat., 5/13 | V Boys Outdoor Track | Greater Hartford | Away | 9:00 a.m. | 6:30am | ||
| Sat., 5/13 | FR Boys Rugby | Fairfield Prep | Home - Staples Stadium [Directions] | 10:00 a.m. | |||
| Sat., 5/13 | V Co-ed Sailing | Fairfield Cup | Away | 9:00 a.m. | Pequot Yacht Club | ||
| Sat., 5/13 | V Co-ed Sailing | ISSA Mallory Doublehanded Championship | Away | TBA | MIT | ||
| Sat., 5/13 | V Girls Outdoor Track | Loucks Games | Away | 8:00 a.m. | 7:00am | ||
| Sun., 5/14 | V Co-ed Sailing | ISSA Mallory Doublehanded Championship | Away | TBA | MIT | ||
| Mon., 5/15 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | W 5-4 | 2:45/5:00 | |
| Mon., 5/15 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Mon., 5/15 | FR Baseball | Fairfield Ludlowe | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | |||
| Mon., 5/15 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | Staples - 166 Darien - 162 | 2:10/5:00 | ED 2:00 |
| Mon., 5/15 | JV Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | |||
| Mon., 5/15 | V Boys Tennis | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 7-0 | 2:30/5:00 | |
| Mon., 5/15 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | W 3-0 | 2:30/6:00 | |
| Mon., 5/15 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | ride with varsity | ||
| Mon., 5/15 | V Girls Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | Staples 197, Darien 208 | ED 2:00 | |
| Mon., 5/15 | JV Girls Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | |||
| Mon., 5/15 | FR Girls Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Mon., 5/15 | V Girls Outdoor Track | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | 2:00/6:00 | ED 1:45 | |
| Mon., 5/15 | V Softball | Fairfield Ludlowe | Home - Wakeman Field [Directions] | 4:00 p.m. | W 3-2 | ||
| Mon., 5/15 | JV Softball | Fairfield Ludlowe | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | |||
| Mon., 5/15 | V Girls Tennis | St. Joseph | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ||
| Tue., 5/16 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 15-1 | 5:30/8:00 | shuttle with JV |
| Tue., 5/16 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | 3:30 | Shuttle with varsity | |
| Tue., 5/16 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Tue., 5/16 | V Boys Outdoor Track | Greenwich | Home - Staples Stadium [Directions] | 4:00 p.m. | |||
| Tue., 5/16 | V Co-ed Sailing | FCSL Women's Championship | Away | 3:00 p.m. | IHYC | ||
| Tue., 5/16 | V Girls Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | Staples 188, Trumbull 200 | ED 2:00 | |
| Tue., 5/16 | JV Girls Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | |||
| Tue., 5/16 | V Girls Lacrosse | Danbury | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 21-8 | ||
| Tue., 5/16 | JV Girls Lacrosse | Danbury | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | |||
| Tue., 5/16 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Tue., 5/16 | V Girls Tennis | Danbury | Away - WCSU Tennis Courts, Westside Campus [Directions] | 2:30 p.m. | W 7-0 | 9:00/12:00 | ED 1:45 |
| Tue., 5/16 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 5/17 | V Baseball | St. Joseph | Away - Harbor Yard [Directions] | 4:30 p.m. | W 21-4 | 2:45/5:00 | |
| Wed., 5/17 | JV Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Wed., 5/17 | FR Baseball | St. Joseph | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | |||
| Wed., 5/17 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | 3:15 p.m. | Staples - 151 Stamford - 205 | 2:20/5:30 | ED 2:05 |
| Wed., 5/17 | JV Boys Golf | Fairfield Prep | Home - Longshore [Directions] | 3:00 p.m. | |||
| Wed., 5/17 | JV Boys Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Wed., 5/17 | V Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Wed., 5/17 | JV Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | |||
| Wed., 5/17 | V Softball | St. Joseph | Home - Wakeman Field [Directions] | 4:00 p.m. | L 5-16 | ||
| Wed., 5/17 | JV Softball | St. Joseph | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | |||
| Wed., 5/17 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | 2:45/5:00 | ||
| Wed., 5/17 | Unified Sports Track | Fairfield Ludlowe | Away [Directions] | 3:00 p.m. | 1:50 | ||
| Thu., 5/18 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Staples - 156 Trumbull - 153 | 2:10/5:00 | ED 2:00 |
| Thu., 5/18 | FR Boys Lacrosse | Ridgefield | Home - Wakeman Field E (grass) [Directions] | Cancelled | Cancelled | ||
| Thu., 5/18 | V Boys Tennis | Quarterfinals vs Fairfield Ludlowe | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | |||
| Thu., 5/18 | JV Boys Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | |||
| Thu., 5/18 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | 2:30/6:00 | |
| Thu., 5/18 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ride with varsity | ||
| Thu., 5/18 | V Girls Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | Staples 198, FFLD Warde 175 | ED 2:00 | |
| Thu., 5/18 | JV Girls Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | |||
| Thu., 5/18 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 5:30 p.m. | 4:00/6:30 | ||
| Thu., 5/18 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 4:00 p.m. | W 11-3 | 2:00/5:00 | ED 1:45 |
| Fri., 5/19 | V Baseball | FCIAC Quarterfinals vs Darien | Home - Staples Baseball Field [Directions] | 4:00 p.m. | |||
| Fri., 5/19 | FR Boys Lacrosse | New Fairfield | Home - Wakeman Field E (grass) [Directions] | 5:00 p.m. | |||
| Fri., 5/19 | V Boys Outdoor Track | Hatter Freshmen Invitational | Away | 4:00 p.m. | 2:00/10:00 | ED 1:30 | |
| Fri., 5/19 | V Boys Outdoor Track | Dream Invitational | Away | 8:00 p.m. | |||
| Fri., 5/19 | V Co-ed Sailing | FCSL Silver Cup | Away | 3:00 p.m. | 2:00 | IHYC ED 1:45 | |
| Fri., 5/19 | V Girls Lacrosse | FCIAC Quarterfinals vs Wilton | Away | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 5/19 | V Girls Outdoor Track | Dream Invitational | Away | 8:00 p.m. | 6:00pm | Danbury HS | |
| Fri., 5/19 | V Girls Tennis | FCIAC Semi-finals vs. New Canaan | Home [Directions] | 2:00 p.m. | |||
| Fri., 5/19 | V Girls Tennis | FCIAC Semi-finals vs New Canaan | Home - Staples HS-Tennis Courts [Directions] | 2:00 p.m. | ED 12:45 | ||
| Sat., 5/20 | V Boys Lacrosse | FCIAC Quarterfinals vs Ridgefield | Away | 2:00 p.m. | 11:30/3:00 | ||
| Sat., 5/20 | V Co-ed Sailing | FCSL Gold Cup | Away | 9:00 a.m. | IHYC | ||
| Mon., 5/22 | FR Boys Lacrosse | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | |||
| Mon., 5/22 | JV Girls Golf | Greenwich | Home - Longshore [Directions] | Cancelled | Cancelled | ||
| Mon., 5/22 | V Girls Lacrosse | FCIAC Semi-Finals vs Darien @ Norwalk HS | Away | 7:00 p.m. | 5:30/8:00 | ||
| Tue., 5/23 | V Boys Golf | Greenwich | Away - Stanwich Country Club [Directions] | 3:15 p.m. | Staples - 170 Greenwich - 161 | 2:00/5:00 | ED 1:50 |
| Tue., 5/23 | JV Boys Golf | Greenwich | Home - Longshore [Directions] | 3:15 p.m. | |||
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Championship | Away | TBA | 12:15/6:00 | ||
| Tue., 5/23 | V Boys Tennis | FCIAC Semi-final vs Darien/Westhill Winner | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | |||
| Tue., 5/23 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:00 p.m. | Staples 201, FFLD Warde 175 | 2:05/5:00 | ED 2:00 |
| Tue., 5/23 | JV Girls Golf | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | 3:15 p.m. | 2:10/5:00 | Par 3 | |
| Tue., 5/23 | V Girls Tennis | FCIAC Finals vs Darien @ Wilton | Away | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 5/24 | V Boys Golf | Brien McMahon | Home - Longshore [Directions] | 3:00 p.m. | Staples - 140 McMahon - 211 | ||
| Wed., 5/24 | JV Boys Golf | Brien McMahon | Home - Longshore [Directions] | 3:00 p.m. | |||
| Wed., 5/24 | V Boys Tennis | FCIAC Finals vs. Ne Canaan @ Wilton | Away | 4:00 p.m. | 2:30/5:00 | ||
| Wed., 5/24 | V Boys Volleyball | Darien | Away [Directions] | 7:00 p.m. | L 0-3 | 5:30/8:00 | |
| Wed., 5/24 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson [Directions] | 3:00 p.m. | Staples 181, FFLD Ludlowe 231 | 2:00 | Smith Richardson |
| Wed., 5/24 | JV Girls Golf | JV FCIAC Tournament | Away | 3:00 p.m. | 2:10 | ||
| Wed., 5/24 | V Girls Outdoor Track | FCIAC Championship | Away | 3:00 p.m. | 12:30 | Danbury HS | |
| Thu., 5/25 | V Boys Golf | Chappa Tournament | Away | 8:00 a.m. | |||
| Thu., 5/25 | V Girls Golf | Fairfield Ludlowe | Home - Longshore [Directions] | Cancelled | Cancelled | ED 2:00 | |
| Thu., 5/25 | V Girls Lacrosse | Greenwich (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | Cancelled | Cancelled | ||
| Fri., 5/26 | JV Boys Tennis | Ridgefield (Scrim.) | Away [Directions] | 4:00 p.m. | 2:30/5:00 | ||
| Fri., 5/26 | V Co-ed Sailing | ISSA Baker Team Race Championship | Away | TBA | Norfolk VA | ||
| Fri., 5/26 | V Co-ed Sailing | ISSA National Invitational Tournament | Away | TBA | IHYC | ||
| Sat., 5/27 | V Baseball | Westhill (Scrim.) | Away [Directions] | 3:00 p.m. | 2:00 | ||
| Sat., 5/27 | V Baseball | Westhill (Scrim.) | Away [Directions] | 3:00 p.m. | 2:00 | ||
| Sat., 5/27 | V Baseball | Westhill (Scrim.) | Away [Directions] | 3:00 p.m. | 2:00 | ||
| Sat., 5/27 | FR Boys Rugby | Freshmen Tournament | Away | 10:00 a.m. | @ Prep | ||
| Sat., 5/27 | V Boys Tennis | CIAC playoffs | Away | 9:00 a.m. | 9:00/5:00 | ||
| Sat., 5/27 | V Co-ed Sailing | ISSA Baker Team Race Championship | Away | TBA | Norfolk Va | ||
| Sat., 5/27 | V Co-ed Sailing | ISSA National Invitational Tournament | Away | TBA | IHYC | ||
| Sat., 5/27 | V Softball | Westhill (Scrim.) | Away [Directions] | Cancelled | Cancelled | 9:30am/12:00 | |
| Sat., 5/27 | V Girls Tennis | CIAC First Round vs. Bristol Central/Newtown winner | Home - Staples HS-Tennis Courts [Directions] | 12:30 p.m. | |||
| Sun., 5/28 | V Co-ed Sailing | ISSA Baker Team Race Championship | Away | TBA | Norfolk, VA | ||
| Sun., 5/28 | V Co-ed Sailing | ISSA National Invitational Tournament | Away | TBA | IHYC | ||
| Tue., 5/30 | V Baseball | CIAC First Round vs Cheshire | Home - Staples Baseball Field [Directions] | 3:30 p.m. | ED 1:45 | ||
| Tue., 5/30 | V Boys Golf | Hollohan Tournament @ CC of Darien | Away | 11:30 p.m. | 10:30 | ||
| Tue., 5/30 | V Boys Tennis | CIAC Playoffs | Away | 2:00 p.m. | 11:30/5:00 | ||
| Tue., 5/30 | V Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | W 13-12 | 3:00/6:00 | |
| Tue., 5/30 | V Girls Tennis | CIAC Class L Quarterfinals vs. Wilton | Home - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | |||
| Wed., 5/31 | V Baseball | CIAC Class LL Second Round vs. Wilton | Away | 4:00 p.m. | Yes | ||
| Wed., 5/31 | V Boys Lacrosse | CIAC First Round vs Greenwich | Away | 4:30 p.m. | 2:30/5:30 | ||
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Manchester HS [Directions] | 3:00 p.m. | 11:15 | ED 11:00 | |
| Wed., 5/31 | V Boys Tennis | CIAC Playoffs | Away | 3:00 p.m. | ED 1:45 | ||
| Wed., 5/31 | V Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | ||
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Manchester HS [Directions] | 3:00 p.m. | ride with boys | ED 11:00 | |
| Wed., 5/31 | V Girls Tennis | CIAC Class L Semi-finals vs. Southington/Greenwich winner | Home - Staples HS-Tennis Courts [Directions] | 3:00 p.m. | |||
| Thu., 6/1 | V Boys Golf | FCIAC Finals @ Fairchild Wheeler | Away | 12:30 p.m. | 10:30 | ||
| Thu., 6/1 | V Boys Outdoor Track | CIAC Class LL Championship | Away | 12:00 p.m. | 10:15 | ||
| Thu., 6/1 | V Girls Golf | FCIAC Championship @ Fairchild Wheeler | Away | 9:00 a.m. | 7:30am/1:00 | ||
| Thu., 6/1 | V Girls Lacrosse | CIAC Class L Quarterfinals vs Greenwich | Away | 5:00 p.m. | 3:00/6:00 | ||
| Thu., 6/1 | V Girls Outdoor Track | CIAC Class LL Championship | Away | 1:00 p.m. | |||
| Thu., 6/1 | V Girls Tennis | CIAC Finals vs Glastonbury | Away | 3:00 p.m. | 1:00/4:30 | ||
| Fri., 6/2 | V Boys Volleyball | CIAC Class L Quarterfinals vs Ridgefield | Away | 6:00 p.m. | 4:00/7:00 | ||
| Sat., 6/3 | V Baseball | CIAC Class LL Quarterfinals vs Westhill | Away | 2:00 p.m. | 12:00/3:00 | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 10:30 | ED 10:30 | |
| Mon., 6/5 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ride with boys | ED 10:30 | |
| Tue., 6/6 | V Boys Golf | CIAC Div. I Championship | Away - Fairview Farms - Harwinton [Directions] | 7:30 a.m. | 5:30am/12:30 | ||
| Tue., 6/6 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | 6:45am/1:30pm | ||
| Wed., 6/7 | V Baseball | Class LL Semi-finals vs.Ridgefield @ Municipal Stadium Waterbury | Away | 3:30 p.m. | 1:00/4:30 | ED 12:25 | |
| Sat., 6/10 | V Baseball | Class LL Finals vs.Amity HS @ Palmer Field Middletown | Away | 12:00 p.m. | 9:30/1:30 | ||
| Sat., 6/10 | V Boys Outdoor Track | New England Championship | Away - Norwell (MA) HS [Directions] | TBA | |||
| Sat., 6/10 | V Girls Outdoor Track | New England Championship | Away - Norwell (MA) HS [Directions] | TBA | |||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | |||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | |||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | |||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | |||
| Wed., 6/21 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | |||
| Wed., 6/21 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | |||
| Sun., 11/26 | V Boys Cross Country | NXN Northeast Regionals | Away | 9:00 a.m. | 8:00am | ||
| Thu., 12/14 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | |||
| Thu., 12/14 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | |||
| Thu., 5/17 | V Girls Tennis | FCIAC Quarterfinals vs. Ridgefield | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | |||