| Staples 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 892 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Masuk | Home - Wakeman Field [Directions] | 1:00 p.m. | ||
| TBA | FR Baseball | Xavier | Away - Xavier H.S. [Directions] | TBA | 10:30/2:30 | |
| TBA | FR Football | New Canaan | Away - Dunning Stadium [Directions] | TBA | 3:30/6:30 | |
| TBA | FR Boys Lacrosse | New Canaan | Home - Wakeman Field E (grass) [Directions] | TBA | ||
| TBA | V Boys Outdoor Track | Brien McMahon | Home - Staples Stadium [Directions] | TBA | ||
| TBA | JV Boys Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | TBA | ||
| TBA | V Boys Water Polo | Suffield Academy | Home - Staples HS Pool [Directions] | 4:00 p.m. | 2:00pm/6:30 | ED 1:45 JV match to follow at 5:30 |
| TBA | JV Boys Water Polo | Suffield Academy | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| TBA | JV Field Hockey | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | TBA | 1:30/4:00 | ED 1:15 |
| TBA | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | TBA | 4:00/6:30 | |
| TBA | JV Field Hockey | Darien | Away - Darien HS [Directions] | Cancelled | 2:30/5:00 | |
| TBA | FR Field Hockey | Greenwich | Home - Ginny Parker Field - Staples [Directions] | TBA | ||
| TBA | FR Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 2:00 p.m. | 12:00/3:00 | |
| TBA | V Girls Outdoor Track | FCIAC Championship | Away | 2:30 p.m. | Yes | |
| TBA | V Girls Outdoor Track | Brien McMahon | Home - Staples Stadium [Directions] | TBA | ||
| TBA | JV Girls Soccer | Brien McMahon | Home - Wakeman Field E (grass) [Directions] | TBA | ||
| TBA | JV Softball | Fairfield Warde | Home - Staples HS - Softball Field [Directions] | TBA | ||
| TBA | JV Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:00 p.m. | 1:30/4:00 | |
| TBA | JV Girls Tennis | Trumbull | Home - Town Farms Tennis Courts [Directions] | TBA | ||
| TBA | JV Girls Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | TBA | ||
| Fri., 9/8 | V Football | Bridgeport Central | Home - Staples Stadium [Directions] | W 52-0 | ||
| Fri., 9/8 | V Boys Soccer | Trinity Catholic | Home - Loeffler Field - Staples HS [Directions] | W 3-0 | ||
| Fri., 9/8 | V Field Hockey | Brien McMahon | Home - Ginny Parker Field - Staples [Directions] | W 6-2 | ||
| Fri., 9/8 | JV Field Hockey | Brien McMahon | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Fri., 9/8 | V Girls Volleyball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | W 3-2 | 2:30/6:00 | |
| Fri., 9/8 | JV Girls Volleyball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 4:00 p.m. | ride with varsity | |
| Sat., 9/9 | V Girls Soccer | Trinity Catholic | Away - Gaglio Field | W 6-0 | 12:00/3:00 | |
| Mon., 9/11 | JV Football | Bridgeport Central | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 9/11 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | T 0-0 | 2:00/5:00 | ED 1:45 |
| Mon., 9/11 | JV Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | W 2-1 | 2:00/5:00 | ED 1:45 |
| Mon., 9/11 | FR Boys Soccer | Danbury | Home - Wakeman Field B (turf) [Directions] | W 7-0 | ||
| Mon., 9/11 | FR Field Hockey | Danbury | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | FR Girls Soccer | Wilton | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Wilton, Stamford, St. Joseph | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Water Polo | Greenwich | Away [Directions] | 4:00 p.m. | 2:30/6:00 | |
| Tue., 9/12 | JV Boys Water Polo | Greenwich | Away [Directions] | 5:00 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Wilton, Stamford, St. Joseph | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 2-0 | 2:00/5:00 | ED 1:45 |
| Tue., 9/12 | JV Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:30 p.m. | 3:30/6:30 | |
| Tue., 9/12 | V Girls Soccer | Danbury | Home - Loeffler Field - Staples HS [Directions] | W 5-0 | ||
| Tue., 9/12 | JV Girls Soccer | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | FR Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 |
| Wed., 9/13 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | T 3-3 | 2:30/5:00 | |
| Wed., 9/13 | JV Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | W 4-0 | 2:30/5:00 | |
| Wed., 9/13 | FR Boys Soccer | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | W 7-1 | ||
| Wed., 9/13 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 2-3 | 2:30/5:00 | |
| Wed., 9/13 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 9/13 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | FR Football | Westhill | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/14 | V Girls Soccer | Fairfield Warde | Home - Loeffler Field - Staples HS [Directions] | W 2-0 | ||
| Thu., 9/14 | JV Girls Soccer | Fairfield Warde | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 9/15 | V Football | Wilton | Away - Fujitani Field - Turf [Directions] | W 49-3 | 4:00/9:00 | |
| Fri., 9/15 | FR Boys Soccer | Wilton | Away - Allen's Field [Directions] | W 3-0 | 2:30/5:00 | |
| Fri., 9/15 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 9/15 | V Girls Volleyball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Fri., 9/15 | JV Girls Volleyball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Sat., 9/16 | V Boys Cross Country | Stratton Brook Invitational | Away | 9:00 a.m. | 8:30am | 2 buses |
| Sat., 9/16 | JV Football | Wilton | Away - Fujitani Field - Turf [Directions] | 10:00 a.m. | 8:30/11:30 | |
| Sat., 9/16 | V Boys Soccer | Wilton | Home - Loeffler Field - Staples HS [Directions] | W 4-0 | ||
| Sat., 9/16 | JV Boys Soccer | Wilton | Home - Loeffler Field - Staples HS [Directions] | W 8-0 | ||
| Sat., 9/16 | V Boys Water Polo | Chelsea Piers | Away | 2:00 p.m. | 1:00pm/4:00pm | |
| Sat., 9/16 | JV Boys Water Polo | Chelsea Piers | Away | 3:00 p.m. | ||
| Sat., 9/16 | V Girls Cross Country | Wilton Invitational | Away | 9:00 a.m. | 7:30am | |
| Sat., 9/16 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 1-4 | 9:30/12:30 | |
| Sat., 9/16 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | 8:00/11:00 | |
| Sat., 9/16 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | W 2-0 | 2:30/5:00 | |
| Sat., 9/16 | JV Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 9/16 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 1:00 p.m. | ||
| Mon., 9/18 | FR Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 9/18 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 1-3 | 2:00/6:00 | ED 1:45 |
| Mon., 9/18 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ride with varsity | ED 1:45 |
| Mon., 9/18 | FR Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | New Canaan, Norwalk, Darien, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00/5:00 | 2 buses ED 1:30 |
| Tue., 9/19 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | L 1-0 | 5:00/7:00 | |
| Tue., 9/19 | JV Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | L 3-2 | 2:30/5:00 | |
| Tue., 9/19 | FR Boys Soccer | Trumbull | Home - Wakeman Field E (grass) [Directions] | W 6-2 | ||
| Tue., 9/19 | V Girls Cross Country | New Canaan, Norwalk, Darien, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:30 |
| Tue., 9/19 | V Field Hockey | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | W 4-1 | ||
| Tue., 9/19 | JV Field Hockey | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 9/19 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 9/19 | V Girls Soccer | Trumbull | Home - Loeffler Field - Staples HS [Directions] | L 1-2 | ||
| Tue., 9/19 | JV Girls Soccer | Trumbull | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Swimming and Diving | East Lyme | Away - East Lyme HS Pool [Directions] | 3:30 p.m. | 1:30/5:00 | ED 1:15 |
| Tue., 9/19 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-0 | 2:30/6:00 | |
| Tue., 9/19 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Tue., 9/19 | FR Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | FR Girls Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 3:00 p.m. | ||
| Fri., 9/22 | V Girls Soccer | Bridgeport Central | Home - Loeffler Field - Staples HS [Directions] | W 6-0 | ||
| Fri., 9/22 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Sat., 9/23 | V Boys Cross Country | Bowdoin Park Classic | Away | 10:00 a.m. | 7:00am | Wappinger Falls, NY |
| Sat., 9/23 | V Football | Brien McMahon | Away - Brien McMahon HS [Directions] | W 44-7 | 11:30/3:30 | |
| Sat., 9/23 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | L 3-0 | 10:15/1:00 | |
| Sat., 9/23 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 5-1 | 8:30 shuttle with varsity | |
| Sat., 9/23 | V Boys Water Polo | Chelsea Piers | Home - Staples HS Pool [Directions] | 2:00 p.m. | ||
| Sat., 9/23 | JV Boys Water Polo | Chelsea Piers | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Sat., 9/23 | V Competitive Cheerleading | Brien McMahon | Away [Directions] | 1:30 p.m. | 11:45/3:30 | |
| Sat., 9/23 | V Field Hockey | Stamford | Home - Ginny Parker Field - Staples [Directions] | W 5-0 | ||
| Sat., 9/23 | JV Field Hockey | Stamford | Home - Ginny Parker Field - Staples [Directions] | 9:00 a.m. | ||
| Sat., 9/23 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 5:00 p.m. | Event | |
| Mon., 9/25 | JV Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:45 p.m. | 2:30/5:00 | |
| Mon., 9/25 | V Boys Soccer | Greenwich | Home - Loeffler Field - Staples HS [Directions] | W 1-0 | ||
| Mon., 9/25 | JV Boys Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | L 2-0 | ||
| Mon., 9/25 | FR Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | L 4-0 | 2:30/5:00 | |
| Mon., 9/25 | V Girls Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/25 | JV Girls Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Mon., 9/25 | V Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Mon., 9/25 | JV Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Mon., 9/25 | FR Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 9/26 | V Boys Cross Country | Danbury, Westhill | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Danbury, Westhill | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Field Hockey | Trumbull | Home - Ginny Parker Field - Staples [Directions] | W 8-1 | ||
| Tue., 9/26 | JV Field Hockey | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 9/26 | FR Field Hockey | Trumbull | Away - Indian Ledge Park [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 9/26 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | W 4-1 | 2:30/5:00 | |
| Tue., 9/26 | JV Girls Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | 2:30/5:00 | |
| Tue., 9/26 | FR Girls Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Wed., 9/27 | V Boys Soccer | Norwalk | Home - Loeffler Field - Staples HS [Directions] | W 1-0 | ||
| Wed., 9/27 | JV Boys Soccer | Norwalk | Home - Wakeman Field E (grass) [Directions] | T 1-1 | ||
| Wed., 9/27 | FR Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | L 3-0 | 2:30/5:00 | |
| Wed., 9/27 | V Boys Water Polo | Canterbury and Loomis Chaffe | Away | 3:30 p.m. | 1:45/5:00 | ED 1:30, game @ Canterbury |
| Wed., 9/27 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 0-3 | 2:30/6:00 | |
| Wed., 9/27 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 9/27 | FR Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Football | Wilton | Away - Fujitani Field - Turf [Directions] | 7:00 p.m. | 5:00/8:00 | |
| Thu., 9/28 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 3-0 | 6:00/8:00 | |
| Thu., 9/28 | JV Girls Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | 4:00 shuttle with varsity | |
| Thu., 9/28 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University- Rec Plex Pool [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 9/28 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 3-0 | 2:30/5:00 | |
| Thu., 9/28 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Fri., 9/29 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | W 9-0 | 1:30/4:00 | ED 1:15 |
| Fri., 9/29 | FR Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 3:00 p.m. | ||
| Sat., 9/30 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 1:00 p.m. | ||
| Mon., 10/2 | FR Field Hockey | Westhill | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Girls Soccer | Brien McMahon | Home - Loeffler Field - Staples HS [Directions] | L 0-1 | ||
| Mon., 10/2 | V Girls Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | L 2-3 | ||
| Mon., 10/2 | JV Girls Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/2 | FR Girls Volleyball | Greenwich | Away - Western MS [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Tue., 10/3 | V Boys Cross Country | Greenwich, Fairfield Ludlowe, Ridgefield | Away - Greenwich Point [Directions] | 4:30 p.m. | 1:45/5:30 | 2 buses ED 1:15 |
| Tue., 10/3 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | W 2-1 | 5:00/7:30 | |
| Tue., 10/3 | JV Boys Soccer | Brien McMahon | Away - BMHS Field 2 [Directions] | W 7-3 | 3:00 shuttle with varsity | |
| Tue., 10/3 | FR Boys Soccer | Brien McMahon | Home - Wakeman Field E (grass) [Directions] | L 2-1 | ||
| Tue., 10/3 | V Girls Cross Country | Greenwich, Fairfield Ludlowe, Ridgefield | Away - Greenwich Point [Directions] | 4:30 p.m. | 1:45/5:30 | ED 1:15 |
| Tue., 10/3 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | W 6-0 | 2:30/5:00 | |
| Tue., 10/3 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | 4:00/6:30 | |
| Tue., 10/3 | V Girls Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Girls Soccer | Westhill | Home - Loeffler Field - Staples HS [Directions] | W 7-2 | ||
| Wed., 10/4 | JV Girls Soccer | Westhill | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Girls Volleyball | Norwalk | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Wed., 10/4 | JV Girls Volleyball | Norwalk | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/5 | FR Football | Norwalk | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/5 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | W 4-0 | 2:30/5:00 | |
| Thu., 10/5 | JV Boys Soccer | Westhill | Away - Rippowam MS - Turf Field [Directions] | T 1-1 | 2:30/5:00 | |
| Thu., 10/5 | FR Boys Soccer | Westhill | Home - Wakeman Field E (grass) [Directions] | L 4-2 | ||
| Thu., 10/5 | V Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | W 4-1 | ||
| Thu., 10/5 | JV Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Thu., 10/5 | FR Girls Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:00 p.m. | 2:30/5:00 | Wolf Park Great Hollow Lake Field |
| Thu., 10/5 | V Girls Swimming and Diving | Trumbull | Home - Staples Pool [Directions] | 4:00 p.m. | 2:30/5:00 55pax | |
| Fri., 10/6 | V Football | Ridgefield | Home - Staples Stadium [Directions] | L 20-24 | Homecoming | |
| Fri., 10/6 | JV Boys Soccer | Stamford | Home - Wakeman Field E (grass) [Directions] | W 5-1 | ||
| Fri., 10/6 | V Boys Water Polo | Horace Mann (NY) | Away | 4:00 p.m. | 2:00pm/6:00 | |
| Fri., 10/6 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 7-0 | 2:30/5:00 | |
| Fri., 10/6 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 10/6 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 1-3 | 2:30/6:00 | |
| Fri., 10/6 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ride with varsity | |
| Sat., 10/7 | V Boys Cross Country | Wickham Park Invitational | Away | 9:40 a.m. | 6:45am | 2 buses |
| Sat., 10/7 | JV Football | Ridgefield | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | V Boys Soccer | Stamford | Home - Loeffler Field - Staples HS [Directions] | L 1-0 | ||
| Sat., 10/7 | FR Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 5-0 | 2:30/5:00 | |
| Sat., 10/7 | V Girls Cross Country | Wickham Park Invitational | Away | 9:40 a.m. | 6:45am | |
| Sat., 10/7 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 1:00 p.m. | ||
| Mon., 10/9 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | L 0-1 | 2:30/5:00 | |
| Mon., 10/9 | JV Girls Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:30 p.m. | 3:00/5:30 | |
| Tue., 10/10 | V Boys Cross Country | Trumbull, Brien McMahon, Fairfield Warde | Away [Directions] | 4:00 p.m. | 2:00/5:00 | 2 buses ED 1:30 |
| Tue., 10/10 | V Boys Soccer | Darien | Home - Loeffler Field - Staples HS [Directions] | L 1-0 | ||
| Tue., 10/10 | JV Boys Soccer | Darien | Home - Wakeman Field E (grass) [Directions] | W 6-0 | ||
| Tue., 10/10 | FR Boys Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | W 2-1 | 2:30/5:00 | |
| Tue., 10/10 | V Girls Cross Country | Trumbull, Brien McMahon, Fairfield Warde | Away [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:30 |
| Tue., 10/10 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | OT-L 1-2 | 2:30 shuttle with varsity | |
| Wed., 10/11 | V Boys Water Polo | Hopkins School | Away | 3:30 p.m. | 1:45/4:30 | ED 1:30 varsity only |
| Wed., 10/11 | FR Girls Soccer | Danbury | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Girls Swimming and Diving | Danbury | Home - Staples HS Pool [Directions] | 6:00 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-2 | 2:30/6:00 | |
| Wed., 10/11 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 10/11 | FR Girls Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | T 0-0 | 2:00/5:00 | ED 1:45 |
| Thu., 10/12 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | W 3-0 | 2:00/5:00 | ED 1:45 |
| Thu., 10/12 | FR Boys Soccer | Ridgefield | Home - Wakeman Field E (grass) [Directions] | T 1-1 | ||
| Thu., 10/12 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | L 0-2 | 5:15/8:00 | |
| Thu., 10/12 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 5:30 p.m. | 4:00 shuttle with varsity | |
| Thu., 10/12 | FR Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | V Girls Soccer | Ridgefield | Home - Loeffler Field - Staples HS [Directions] | W 2-0 | ||
| Thu., 10/12 | JV Girls Soccer | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Football | Darien | Home - Staples Stadium [Directions] | L 6-32 | ||
| Fri., 10/13 | V Boys Water Polo | Cardinal Tournament | Away | 6:00 p.m. | 4:00/7:00 | |
| Fri., 10/13 | FR Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 10/13 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | W 3-2 | ||
| Fri., 10/13 | JV Girls Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/13 | FR Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 10/14 | V Boys Water Polo | Cardinal Tournament | Away | TBA | Yes | |
| Sat., 10/14 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | W 2-0 | 11:00/1:30 | |
| Sat., 10/14 | FR Girls Soccer | Fairfield Ludlowe | Home - Loeffler Field - Staples HS [Directions] | 1:30 p.m. | ||
| Sat., 10/14 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 1:00 p.m. | ||
| Mon., 10/16 | JV Football | Darien | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/16 | V Boys Soccer | Fairfield Ludlowe | Home - Loeffler Field - Staples HS [Directions] | T 0-0 | ||
| Mon., 10/16 | JV Boys Soccer | Fairfield Ludlowe | Home - Wakeman Field E (grass) [Directions] | W 3-0 | ||
| Mon., 10/16 | FR Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | W 4-1 | 2:30/5:00 | |
| Mon., 10/16 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 10/16 | V Girls Volleyball | Darien | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Mon., 10/16 | JV Girls Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/16 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 10/17 | V Field Hockey | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | W 2-0 | ||
| Tue., 10/17 | JV Field Hockey | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 10/17 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 10/18 | V Boys Water Polo | Choate Rosemary Hall | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | JV Boys Water Polo | Choate Rosemary Hall | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Wed., 10/18 | JV Girls Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:30 p.m. | 3:15/5:30 | |
| Wed., 10/18 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 4:00 p.m. | 2:30/5:00 55pax | |
| Wed., 10/18 | JV Girls Swimming and Diving | Westhill/Stamford | Away [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 10/18 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 3-2 | 3:30/8:00 | |
| Wed., 10/18 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | ride with varsity | |
| Wed., 10/18 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 10/19 | FR Football | St. Joseph | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/19 | V Field Hockey | Darien | Home - Ginny Parker Field - Staples [Directions] | W 2-1 | ||
| Thu., 10/19 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 10/20 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | W 27-0 | 4:00/9:00 | |
| Fri., 10/20 | V Boys Soccer | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | W 2-0 | 2:30/5:00 | |
| Fri., 10/20 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | L 2-1 | 2:30/5:00 | |
| Fri., 10/20 | FR Boys Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | W 8-0 | ||
| Fri., 10/20 | V Boys Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | JV Boys Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Fri., 10/20 | V Competitive Cheerleading | Norwalk | Away [Directions] | 7:00 p.m. | 5:00/9:00 | |
| Fri., 10/20 | V Girls Soccer | New Canaan | Home - Loeffler Field - Staples HS [Directions] | W 1-0 | ||
| Fri., 10/20 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 4:30 p.m. | 2:30/5:00 55pax | |
| Fri., 10/20 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 4:30 p.m. | ride with varsity | |
| Fri., 10/20 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | W 3-1 | ||
| Fri., 10/20 | JV Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/20 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples Field House [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Sat., 10/21 | FR Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 10/21 | Miscellaneous Events | PAL Football | Home - Staples Stadium [Directions] | 5:00 p.m. | Event | |
| Mon., 10/23 | V Boys Cross Country | Sub-varsity meet at Wilton | Away | 4:00 p.m. | 2:00pm | ED 1:30 |
| Mon., 10/23 | JV Football | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | 4:00/7:00 | |
| Mon., 10/23 | V Boys Soccer | St. Joseph | Home - Loeffler Field - Staples HS [Directions] | W 3-1 | ||
| Mon., 10/23 | JV Boys Soccer | St. Joseph | Home - Wakeman Field E (grass) [Directions] | W 9-0 | ||
| Mon., 10/23 | FR Field Hockey | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | W 3-0 | 2:30 | |
| Mon., 10/23 | JV Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 10/23 | FR Girls Volleyball | Weston | Away - WHS Old Gymnasium [Directions] | 3:30 p.m. | ride with JV | |
| Tue., 10/24 | V Girls Cross Country | Sub-varsity meet at Wilton | Away | 4:00 p.m. | 2:00 | ED 1:30 Allen's Meadow |
| Wed., 10/25 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 5-2 | 1:30 | ED 1:20 |
| Wed., 10/25 | JV Field Hockey | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | Cancelled | ||
| Wed., 10/25 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | T 1-1 | 2:30/5:00 | |
| Wed., 10/25 | JV Girls Soccer | St. Joseph | Away [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 10/25 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-1 | 2:30/6:30 | |
| Wed., 10/25 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 10/25 | FR Girls Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Darien | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Fri., 10/27 | V Football | Fairfield Warde | Home - Staples Stadium [Directions] | W 24-14 | ||
| Fri., 10/27 | V Boys Water Polo | Hopkins School | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | JV Boys Water Polo | Hopkins School | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Fri., 10/27 | V Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | L 0-3 | ||
| Fri., 10/27 | JV Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 10/28 | JV Football | Fairfield Warde | Home - Staples Stadium [Directions] | Cancelled | ||
| Mon., 10/30 | JV Football | Greenwich | Home - Staples Stadium [Directions] | Cancelled | ||
| Tue., 10/31 | JV Field Hockey | Greenwich Academy | Away | 3:30 p.m. | 2:30/4:30 | |
| Thu., 11/2 | FR Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m.. | 2:30/5:00 | |
| Thu., 11/2 | V Boys Water Polo | Choate Rosemary Hall | Away | 5:00 p.m. | 3:00pm | JV to follow at 6pm |
| Thu., 11/2 | JV Field Hockey | Sacred Heart Academy | Home - Ginny Parker Field - Staples [Directions] | 3:45 p.m. | ||
| Fri., 11/3 | V Boys Water Polo | Loomis Chaffee School | Away | 4:30 p.m. | 2:30/5:30 | |
| Sat., 11/4 | V Football | St. Joseph | Away [Directions] | L 9-49 | 9:00/2:00 | |
| Sat., 11/4 | JV Boys Water Polo | Hotchkiss | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Sat., 11/4 | V Competitive Cheerleading | St. Joseph | Away [Directions] | 12:00 p.m. | 9:30/2:00 | |
| Mon., 11/6 | JV Football | St. Joseph | Away [Directions] | 3:00 p.m. | 1:45/5:00 | |
| Thu., 11/9 | FR Football | Trumbull | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Fri., 11/10 | V Football | Stamford | Away - Stamford HS [Directions] | W 42-0 | 3:00/8:00 | |
| Fri., 11/10 | V Competitive Cheerleading | Stamford | Away [Directions] | 6:00 p.m. | 4:00/8:00 | |
| Sat., 11/18 | JV Football | Greenwich | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/18 | FR Football | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | 8:00/12:00 | |
| Thu., 11/23 | V Football | Greenwich | Home - Staples Stadium [Directions] | L 14-31 | ||
| Wed., 12/13 | V Wrestling | Greenwich | Away - GHS Gymnasium [Directions] | 5:00 p.m. | 3:00/6:00 | |
| Wed., 12/13 | V Girls Ice Hockey | Avon | Home - Terry Conners Ice Rink [Directions] | L 0-2 | ||
| Thu., 12/14 | V Girls Basketball | Bethel | Away - Bethel HS [Directions] | L 43-53 | 4:00/8:00 | |
| Thu., 12/14 | JV Girls Basketball | Bethel | Away - Bethel HS [Directions] | 5:15 p.m. | ride with varsity | |
| Fri., 12/15 | V Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | W 48-38 | ||
| Fri., 12/15 | JV Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/15 | FR Girls Basketball | New Canaan | Home - Staples Field House [Directions] | 4:00 p.m. | ||
| Sat., 12/16 | V Boys Indoor Track | FCAIC Qualifier #1 St. Joe's, Ridgefield, Trumbull, Greenwich, Stamford, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Wrestling | Ludlowe Invitational | Away | 10:00 a.m. | 7:00/1:00 | |
| Sat., 12/16 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | L 4 to 1 | 2:45 pm | |
| Sat., 12/16 | V Girls Indoor Track | FCIAC Developmental meet #1 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Girls Indoor Track | AT&T Coaches Hall of Fame | Away | 12:00 p.m. | 10:00am | New Balance Center |
| Mon., 12/18 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Center, Cromwell [Directions] | L 2-4 | 2:20 pm | |
| Tue., 12/19 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | W 55-51 | 4:00/8:00 | |
| Tue., 12/19 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ride with varsity | |
| Tue., 12/19 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 12/20 | V Boys Basketball | Bullard Havens Tech | Home - Staples H.S. Gym [Directions] | W 54-46 | ||
| Wed., 12/20 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | T 3-3(OT) | 6:00/10:00 | @ Northford |
| Wed., 12/20 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | 1:45/4:15 | ED 1:30 |
| Wed., 12/20 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | L 3-9 | ||
| Thu., 12/21 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 12/22 | V Boys Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | L 49-58 | ||
| Fri., 12/22 | JV Boys Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/22 | FR Boys Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | W 61-50 | 2:30/6:30 | |
| Fri., 12/22 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ride with varsity | |
| Fri., 12/22 | V Girls Gymnastics | Greenwich, Innovation | Away - Greenwich YWCA [Directions] | 125.2 | 4:00/7:00 | |
| Sat., 12/23 | V Boys Ice Hockey | Daniel Hand | Home - Milford Ice Pavilion [Directions] | W 4-3 | ||
| Wed., 12/27 | V Boys Basketball | Kolbe Cathedral | Home - Wilton HS [Directions] | L 48-69 | 3:00pm/6:00 | |
| Wed., 12/27 | V Boys Ice Hockey | Norwich Free Academy | Away - Norwich Free Academy [Directions] | W 9-2 | 1:30/6:30 | |
| Wed., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away - Hillhouse | 11:30 a.m. | 9:15am | |
| Wed., 12/27 | V Wrestling | Danbury, Darien, Norwalk | Away - Danbury HS - NEW gym [Directions] | 10:00 a.m. | 8:00/12:00 | |
| Wed., 12/27 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Warde Main Gym [Directions] | W 51-45 | 11:00/2:00 | |
| Thu., 12/28 | V Girls Basketball | Fairfield Warde | Away - Fairfield Ludlowe H.S. [Directions] | W 57-52 | Yes | |
| Fri., 12/29 | V Boys Basketball | Newtown | Away [Directions] | L 55-64 | Yes | |
| Fri., 12/29 | V Wrestling | Maloney, New Britain | Away - Maloney HS [Directions] | 10:00 a.m. | 7:45am/12:00 | |
| Fri., 12/29 | V Girls Indoor Track | Marine Corp Holiday Classic | Away | 9:00 a.m. | 6:30am | New Balance Center |
| Sat., 12/30 | V Boys Ice Hockey | Amity | Home - Milford Ice Pavilion [Directions] | W 3-2 | ||
| Tue., 1/2 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 1-4 | 2:30 pm | |
| Wed., 1/3 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 43-77 | 4:00pm/8:00pm | |
| Wed., 1/3 | JV Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ride with varsity | |
| Wed., 1/3 | FR Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 1/3 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | L 0-4 | 4:15/8:30 | @ Dilungo Rink EH |
| Wed., 1/3 | V Girls Basketball | Danbury | Home - Staples H.S. Gym [Directions] | W 51-42 | ||
| Wed., 1/3 | JV Girls Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/3 | FR Girls Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Girls Indoor Track | Elm City Relays | Away | 4:00 p.m. | 2:00pm | |
| Fri., 1/5 | JV Girls Squash | Rye | Away | 5:00 p.m. | 3:30/7:00 | Yale University, Payne Whitney Gym |
| Sat., 1/6 | V Boys Ice Hockey | Masuk | Home - Milford Ice Pavilion [Directions] | W 3-1 | ||
| Sat., 1/6 | V Boys Indoor Track | FCIAC Qualifier #2 Greenwich, Danbury, St Joe's, McMahon, Trumbull, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Boys Indoor Track | US Army Hispanic Games | Away - Armory | 8:30 a.m. | Yes | |
| Sat., 1/6 | V Wrestling | Warde Invitational | Away | 10:00 a.m. | 8:00/12:00 | |
| Sat., 1/6 | V Girls Gymnastics | Pomperaug Invitational | Away | 124.95 | 8:00am | |
| Sat., 1/6 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Terry Conners Ice Rink [Directions] | L 1-2 | ||
| Sat., 1/6 | V Girls Indoor Track | FCIAC Developmental meet #2 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Girls Indoor Track | Elm City Relays | Away | 9:00 a.m. | 7:00am | Hillhouse |
| Mon., 1/8 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 58-74 | 4:00pm/8:00pm | |
| Mon., 1/8 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Mon., 1/8 | FR Boys Basketball | Fairfield Warde | Away [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 1/9 | V Boys Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Tue., 1/9 | V Boys Basketball | Wilton | Home - Staples H.S. Gym [Directions] | L 65-86 | ||
| Tue., 1/9 | JV Boys Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Girls Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Tue., 1/9 | V Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 51-34 | 4:00/8:00 | |
| Tue., 1/9 | JV Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ride with varsity | |
| Tue., 1/9 | FR Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 3:45 p.m. | 2:30/5:00 | |
| Wed., 1/10 | V Boys Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Wed., 1/10 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | W 3-2(OT) | 4:00/8:00 | |
| Wed., 1/10 | V Boys Swimming and Diving | Ridgefield | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/10 | V Girls Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Wed., 1/10 | V Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | W 54-27 | ||
| Wed., 1/10 | JV Girls Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/10 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 124 | 4:30/7:30 | |
| Wed., 1/10 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | W 8-2 | ||
| Thu., 1/11 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | L 41-55 | 4:00pm/8:00pm | |
| Thu., 1/11 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Thu., 1/11 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 1/11 | V Wrestling | Trumbull | Away - Auxiliary gym [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Fri., 1/12 | V Boys Squash | New Haven | Away | 4:30 p.m. | ride with girls | Yale University, Payne Whitney Gym |
| Fri., 1/12 | JV Boys Squash | New Haven | Away | 4:30 p.m. | ride with girls | |
| Fri., 1/12 | V Boys Swimming and Diving | Trumbull | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | L 53-30 | ||
| Fri., 1/12 | JV Girls Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Girls Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Gymnastics | Westhill, New Canaan | Away - Westhill - New Gymnasium [Directions] | 123.25 | 3:30/6:30 | |
| Fri., 1/12 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | L 2-7 | 2:15 pm | |
| Fri., 1/12 | V Girls Squash | New Haven | Away | 4:30 p.m. | Yes | Yale University Payne Whitney Gym |
| Fri., 1/12 | JV Girls Squash | New Haven | Away | 4:30 p.m. | ride with varsity | |
| Sat., 1/13 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | W 6-1 | 6:00/9:30 | |
| Sat., 1/13 | V Boys Indoor Track | FCIAC Qualifier #3 Ridgefield, Norwalk, Trumbull, Warde, New Canaan, Westhill, Stamford | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invitational | Away - Hillhouse | 2:00 p.m. | 11:30 | |
| Sat., 1/13 | V Wrestling | Staples Duals | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | V Competitive Cheerleading | Hatterfest | Away | 10:00 a.m. | 7am | |
| Sat., 1/13 | V Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | L 1-5 | ||
| Sat., 1/13 | V Girls Indoor Track | FCIAC Developmental meet #3 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | SCC Invitational | Away | 9:00 a.m. | 7:00am | Hillhouse HS |
| Mon., 1/15 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | W 8-6 | 10:15 am | |
| Tue., 1/16 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | W 8-1 | 3:30/8:30 | |
| Tue., 1/16 | V Girls Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | W 66-22 | ||
| Tue., 1/16 | JV Girls Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/16 | FR Girls Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/17 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | L 69-82 | 4:00pm/8:00pm | |
| Wed., 1/17 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Wed., 1/17 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 1/17 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:30/4:00 | ED 1:15 |
| Wed., 1/17 | V Wrestling | Westhill | Away - Westhill - New Gymnasium [Directions] | 5:30 p.m. | 3:00/6:00 | |
| Wed., 1/17 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners Ice Rink [Directions] | L 1-4 | ||
| Thu., 1/18 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | W 4-1 | 5:00/10:00 | |
| Fri., 1/19 | V Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | W 51-39 | ||
| Fri., 1/19 | JV Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Boys Indoor Track | Yale Invitational | Away | 1:00 p.m. | 11:00 & 1:00 | 2 buses, different start times |
| Fri., 1/19 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | W 67-17 | 4:00/8:00 | |
| Fri., 1/19 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ride with varsity | |
| Fri., 1/19 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 1/19 | V Girls Indoor Track | Yale Classic Invitational | Away | 12:00 p.m. | 10:00am | |
| Sat., 1/20 | V Boys Indoor Track | FCIAC Qualifer #4 Stamford, St Joe's, Darien, Greenwich, Danbury, McMahon | Home [Directions] | 10:00 a.m. | ||
| Sat., 1/20 | V Boys Indoor Track | Yale Invitational | Away | 9:00 a.m. | Yes | |
| Sat., 1/20 | V Wrestling | John Chacho Duals | Home - Staples H.S. Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/20 | V Competitive Cheerleading | Wildcat Open | Away - Seymour HS | 11:00 a.m. | 7:15am | |
| Sat., 1/20 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | L 1-2 | ||
| Sat., 1/20 | V Girls Indoor Track | FCIAC Developmental Meet #4 | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | Yale Classic Invitational | Away | 8:00 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | SCC Invitational | Away | TBA | 7:00am | Hillhouse |
| Tue., 1/23 | V Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | L 60-62 | ||
| Tue., 1/23 | JV Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | L 47-64 | 3:00/6:30 | |
| Tue., 1/23 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Tue., 1/23 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | 127.55 | 2:30/5:00 | |
| Wed., 1/24 | V Boys Ice Hockey | Lyman Hall | Home - Milford Ice Pavilion [Directions] | L 1-4 | no bus needed | |
| Wed., 1/24 | V Boys Swimming and Diving | Greenwich | Home - Staples HS Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/24 | V Wrestling | Stamford | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/24 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | L 0-3 | ||
| Thu., 1/25 | V Boys Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Thu., 1/25 | V Girls Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Thu., 1/25 | V Girls Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | W 56-45 | ||
| Thu., 1/25 | JV Girls Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/25 | FR Girls Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/25 | V Girls Gymnastics | Westhill, New Canaan, Trumbull | Away [Directions] | 125 | 3:45/7:00 | |
| Fri., 1/26 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 49-59 | 4:00pm/8:00pm | |
| Fri., 1/26 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ride with varsity | |
| Fri., 1/26 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 1/26 | V Wrestling | Westport Town Crown | Away | TBA | 2:30/4:00 | GFA |
| Fri., 1/26 | V Girls Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | W 53-34 | ||
| Fri., 1/26 | JV Girls Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/27 | V Boys Ice Hockey | Trinity Catholic | Home - Milford Ice Pavilion [Directions] | W 5-3 | no bus needed | |
| Sat., 1/27 | V Wrestling | Highlander Invitational | Away - Portland HS | 9:00 a.m. | 6:15am | |
| Sat., 1/27 | V Girls Gymnastics | Foran, Trumbull | Away - Next Dimension Gymnastics [Directions] | Cancelled | 4:30/8:00 | |
| Sat., 1/27 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 0-7 | ||
| Mon., 1/29 | V Boys Squash | Hopkins School | Away | 4:00 p.m. | 3:00/6:00 | |
| Mon., 1/29 | V Girls Squash | Hopkins School | Away | 4:00 p.m. | ride with boys | |
| Tue., 1/30 | V Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | W 68-51 | 4:00pm/8:00pm | |
| Tue., 1/30 | JV Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | 5:15 p.m. | ride with varsity | |
| Tue., 1/30 | FR Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 1/30 | V Girls Basketball | Westhill | Home - Staples H.S. Gym [Directions] | W 62-33 | ||
| Tue., 1/30 | JV Girls Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/31 | V Boys Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Wed., 1/31 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Milford Ice Pavilion [Directions] | W 9-6 | no bus needed | |
| Wed., 1/31 | V Boys Squash | St. Lukes | Away | 4:45 p.m. | 3:00/6:30 | |
| Wed., 1/31 | JV Boys Squash | St. Lukes | Away | 4:45 p.m. | ride with varsity | |
| Wed., 1/31 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | 1:45/4:15 | ED 1:30 |
| Wed., 1/31 | V Wrestling | Ridgefield | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/31 | V Girls Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Wed., 1/31 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners Ice Rink [Directions] | W 2-0 | ||
| Thu., 2/1 | V Boys Basketball | Stamford | Home - Staples H.S. Gym [Directions] | L 57-83 | ||
| Thu., 2/1 | JV Boys Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/1 | FR Boys Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/1 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | L 40-56 | 4:00/8:00 | |
| Thu., 2/1 | JV Girls Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | ride with varsity | |
| Thu., 2/1 | FR Girls Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 2/2 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Pat Spinola Natatorium [Directions] | 3:30 p.m. | 1:45/4:15 | ED 1:30 |
| Sat., 2/3 | V Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | L 38-73 | ||
| Sat., 2/3 | JV Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 3-6 | 6:00/9:30 | |
| Sat., 2/3 | JV Wrestling | Ludlowe JV Tournament | Away | 9:00 a.m. | 7:30am | |
| Sat., 2/3 | V Competitive Cheerleading | FCIAC | Away - Wilton HS | 11:30 a.m. | 7:45am | |
| Sat., 2/3 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | 129.85 | 12:30/3:00 | |
| Sat., 2/3 | V Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | L 1-5 | ||
| Tue., 2/6 | V Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | L 55-67 | ||
| Tue., 2/6 | JV Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Darien | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Wrestling | Fairfield Warde | Home - Staples Field House [Directions] | 6:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | L 36-47 | 2:30/6:30 | |
| Tue., 2/6 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Tue., 2/6 | V Girls Gymnastics | Fairfield Ludlowe | Away - Gymnastics & Cheer Academy [Directions] | 121.65 | 6:00/8:00 | |
| Tue., 2/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | W 5-3 | ||
| Thu., 2/8 | V Boys Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Thu., 2/8 | V Boys Swimming and Diving | Wilton | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Thu., 2/8 | V Girls Alpine Skiing | Race | Away - Mt Southington | 4:30 p.m. | 2:00pm | ED 1:45 |
| Fri., 2/9 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 59-77 | 4:00pm/8:00pm | |
| Fri., 2/9 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Fri., 2/9 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 2/9 | V Boys Swimming and Diving | Danbury | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | L 56-49 OT | ||
| Fri., 2/9 | JV Girls Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | FR Girls Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | T 4-4(OT) | 5:45/9:30 | |
| Sat., 2/10 | V Competitive Cheerleading | Warde Winter Challenge | Away - Fairfield Warde HS | TBA | 8:15am | |
| Sat., 2/10 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 1-7 | ||
| Mon., 2/12 | V Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | W 64-51 | ||
| Mon., 2/12 | JV Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | W 54-53 OT | 4:00/8:00 | |
| Mon., 2/12 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ride with varsity | |
| Mon., 2/12 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 2/14 | V Boys Ice Hockey | Greenwich | Home - Milford Ice Pavilion [Directions] | L 0-5 | no bus needed | |
| Wed., 2/14 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | W 4-3(OT) | ||
| Fri., 2/16 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | W 3-2 | 3:00 pm | |
| Sat., 2/17 | V Boys Ice Hockey | Ridgefield | Home - Milford Ice Pavilion [Directions] | L 1-2 | no bus needed | |
| Mon., 2/19 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | W 67-50 | 1:45/6:00pm | |
| Mon., 2/19 | JV Boys Basketball | New Canaan | Away [Directions] | 3:15 p.m. | ride with varsity | |
| Mon., 2/19 | FR Boys Basketball | New Canaan | Away [Directions] | 1:00 p.m. | 11:30/2:00 | |
| Tue., 2/20 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | W 1-0 | 1:30/5:30 | @ Northford |
| Wed., 2/21 | V Boys Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | L 49-61 | ||
| Wed., 2/21 | JV Boys Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/22 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavilion [Directions] | W 9-1 | no bus needed | |
| Tue., 2/27 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Milford Ice Pavilion [Directions] | T 2-2(OT) | no bus needed | |
| Sat., 3/3 | V Competitive Cheerleading | States | Away - Hillhouse HS | TBA | 7:00am/12:00 | |
| Sat., 3/24 | FR Boys Rugby | Pelham | Away | 3:30 p.m. | 12:30/3:30 | |
| Wed., 3/28 | FR Boys Rugby | Fairfield Warde | Away [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 3/29 | V Boys Rugby | Fairfield Prep | Away [Directions] | 4:00 p.m. | 2:30/6:00 | |
| Sat., 3/31 | V Boys Lacrosse | Bronxville (NY) | Away | W 10-8 | 9:00am/12:00pm | |
| Sat., 3/31 | JV Boys Rugby | Fairfield Prep | Away - Fairfield Prep [Directions] | 11:00 a.m. | 9:30/12:00 | |
| Sat., 3/31 | V Softball | Joel Barlow | Home - Wakeman Field [Directions] | L 1-3 | ||
| Wed., 4/4 | V Boys Lacrosse | Brien McMahon | Home - Staples Stadium [Directions] | W 15-2 | ||
| Wed., 4/4 | JV Boys Lacrosse | Brien McMahon | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Wed., 4/4 | V Boys Rugby | Simsbury | Away [Directions] | 6:15 p.m. | 3:30 | |
| Wed., 4/4 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-0 | 2:30/6:00 | |
| Wed., 4/4 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | ride with varsity | |
| Wed., 4/4 | FR Girls Lacrosse | Trumbull | Away - New Turf Field [Directions] | W 11-5 | 2:30/5:00 | |
| Thu., 4/5 | V Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | W 19-3 | 2:30/5:00 | |
| Thu., 4/5 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:30 p.m. | 4:00/6:30 | |
| Thu., 4/5 | FR Boys Rugby | Fairfield Prep | Away [Directions] | 4:30 p.m. | 3:00 | |
| Thu., 4/5 | V Boys Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | W 5-2 | 2:30/5:00 | separate return buses |
| Thu., 4/5 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | 2:30/5:00 | separate return buses |
| Thu., 4/5 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Staples 221, Ludlowe 204 (L) | 2:10/5:00 | |
| Thu., 4/5 | V Girls Lacrosse | Brien McMahon | Home - Ginny Parker Field - Staples [Directions] | W 17-2 | ||
| Thu., 4/5 | JV Girls Lacrosse | Brien McMahon | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 4/5 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/5 | JV Girls Tennis | Fairfield Warde | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/6 | FR Boys Lacrosse | Greenwich | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Fri., 4/6 | V Boys Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Fri., 4/6 | JV Boys Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/6 | FR Girls Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | 2:30/5:00 | |
| Fri., 4/6 | V Girls Water Polo | Greenwich | Away [Directions] | 3:00 p.m. | 1:15pm/4:00 | ED 1:00 |
| Sat., 4/7 | V Baseball | Xavier | Home - Staples Baseball Field [Directions] | W 5-3 | ||
| Sat., 4/7 | JV Baseball | Xavier | Home - Long Lots Elementary [Directions] | 1:00 p.m. [Detailed Results] | ||
| Sat., 4/7 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 13-1 | 4:00/7:00 | |
| Sat., 4/7 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Sat., 4/7 | FR Boys Lacrosse | St. Anthonys (NY) | Home - Staples Stadium [Directions] | 1:00 p.m. | ||
| Sat., 4/7 | V Girls Outdoor Track | Hamonnasset (FR) Invitational | Away - Hand HS | Cancelled | 7:00am | |
| Sat., 4/7 | V Softball | Masuk | Home - Wakeman Field [Directions] | L 0-12 | ||
| Sat., 4/7 | V Girls Water Polo | Choate Rosemary Hall | Away | 3:00 p.m. | 1:00pm/4:00 | |
| Mon., 4/9 | V Baseball | Trinity Catholic | Home - Staples Baseball Field [Directions] | W 11-4 | ||
| Mon., 4/9 | JV Baseball | Trinity Catholic | Home - Long Lots Field [Directions] | 4:00 p.m. | ||
| Mon., 4/9 | V Boys Tennis | Fairfield Prep | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/9 | V Boys Tennis | Wilton | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/9 | V Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Mon., 4/9 | JV Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/9 | V Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | W 5-2 | 2:30/5:00 | |
| Tue., 4/10 | V Boys Lacrosse | Fairfield Warde | Home - Staples Stadium [Directions] | W 10-5 | ||
| Tue., 4/10 | JV Boys Lacrosse | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/10 | FR Boys Lacrosse | Ridgefield | Home - Wakeman Field E (grass) [Directions] | Cancelled | ||
| Tue., 4/10 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | W 14-3 | 2:30/5:00 | |
| Tue., 4/10 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | 3:45/6:30 | |
| Wed., 4/11 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | W 8-2 | 2:00/5:30 | |
| Wed., 4/11 | JV Baseball | Danbury | Away - Westerner Baseball Field, Rogers Park [Directions] | 3:45 p.m. | 2:00/5:30 | |
| Wed., 4/11 | FR Baseball | Danbury | Home - Staples Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/11 | V Boys Volleyball | Southington | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Wed., 4/11 | JV Boys Volleyball | Southington | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Wed., 4/11 | V Softball | Danbury | Home - Wakeman Field [Directions] | W 5-3 | ||
| Wed., 4/11 | JV Softball | Danbury | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/12 | V Boys Lacrosse | Norwalk | Home - Staples Stadium [Directions] | W 18-2 | ||
| Thu., 4/12 | JV Boys Lacrosse | Norwalk | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 4/12 | V Softball | Fairfield Ludlowe | Home - Wakeman Field [Directions] | L 3-16 | ||
| Fri., 4/13 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | W 10-4 | 10:30/1:30 | |
| Fri., 4/13 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 12:00 p.m. | 10:30/1:30 | |
| Fri., 4/13 | FR Baseball | Fairfield Warde | Home - Staples Baseball Field [Directions] | 12:00 p.m. | ||
| Fri., 4/13 | FR Boys Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 4/13 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 7-19 | 4:30/8:00 | |
| Fri., 4/13 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 4/13 | V Softball | Fairfield Warde | Home - Wakeman Field [Directions] | L 2-11 | ||
| Sat., 4/14 | V Boys Lacrosse | Kellenberg Memorial (NY) | Home - Staples Stadium [Directions] | W 9-3 | ||
| Sat., 4/14 | JV Boys Lacrosse | Kellenberg Memorial (NY) | Home - Wakeman Field B (turf) [Directions] | 1:00 p.m. | ||
| Sat., 4/14 | V Girls Water Polo | Hotchkiss | Home - Staples HS Pool [Directions] | Cancelled | ||
| Sat., 4/14 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 4:30 p.m. | ||
| Mon., 4/16 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | W 3-0 | 2:30/6:00 | |
| Mon., 4/16 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 4/16 | V Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | L 6-13 | ||
| Mon., 4/16 | JV Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Mon., 4/16 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | 3:30 p.m. | 2:30/5:00 | |
| Tue., 4/17 | V Baseball | Wilton | Home - Staples Baseball Field [Directions] | W 12-1 (6) | ||
| Tue., 4/17 | JV Baseball | Wilton | Home - Wakeman Field [Directions] | 4:30 p.m. | ||
| Tue., 4/17 | V Boys Golf | Trinity Catholic | Home - Longshore [Directions] | Staples 153 Trinity 207 | ||
| Tue., 4/17 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:15 p.m. | 2:15/5:00 | |
| Tue., 4/17 | V Boys Lacrosse | Greenwich | Home - Staples Stadium [Directions] | L 6-9 | ||
| Tue., 4/17 | JV Boys Lacrosse | Greenwich | Home - Wakeman Field B (turf) [Directions] | 5:00 p.m. | ||
| Tue., 4/17 | V Boys Outdoor Track | Ridgefield, Trumbull | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 1:45/6:00 | 2 buses |
| Tue., 4/17 | V Boys Tennis | Bridgeport Central | Away - Central H.S. Tennis Courts [Directions] | W 7-0 | 2:30/5:00 | |
| Tue., 4/17 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | W 15-3 | 2:30/5:00 | |
| Tue., 4/17 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | 3:00/5:00 | |
| Tue., 4/17 | FR Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 4/17 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | L 7-8 | 2:30/5:30 | |
| Tue., 4/17 | V Girls Tennis | Bridgeport Central | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/18 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | L 8-2 | 2:45/5:30 | |
| Wed., 4/18 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Wed., 4/18 | FR Baseball | Trumbull | Home - Staples Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/18 | V Boys Golf | Westhill | Away - Hubbard Brennan Golf Course [Directions] | Staples 164 Westhill 169 | 2:00/4:30 | |
| Wed., 4/18 | JV Boys Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 4/18 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Wed., 4/18 | V Boys Tennis | Danbury | Away - Danbury HS Tennis Courts [Directions] | W 7-0 | 2:00/5:00 | ED 1:45 |
| Wed., 4/18 | V Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-0 | 2:30/6:00 | |
| Wed., 4/18 | JV Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | Cancelled | ride with varsity | |
| Wed., 4/18 | V Co-ed Sailing | Greenwich | Away - Indian Harbor [Directions] | 4:00 p.m. | 2:15/5:00 | |
| Wed., 4/18 | FR Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Wed., 4/18 | V Girls Outdoor Track | Trumbull, Ridgefield | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30/6:00 | |
| Wed., 4/18 | V Softball | Trumbull | Home - Wakeman Field [Directions] | L 0-11 | ||
| Wed., 4/18 | JV Softball | Trumbull | Home - Staples HS - Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/18 | JV Girls Tennis | Fairfield Ludlowe | Home - Town Farms Tennis Courts [Directions] | 3:30 p.m. | ||
| Wed., 4/18 | V Girls Water Polo | Sacred Heart Academy | Home - Staples HS Pool [Directions] | 4:30 p.m. | ||
| Thu., 4/19 | JV Boys Lacrosse | Bronxville (NY) | Away | 5:00 p.m. | 2:30/6:00 | |
| Thu., 4/19 | FR Boys Rugby | Harvey School (NY) | Away | 5:00 p.m. | 3:00/6:00 | |
| Thu., 4/19 | V Girls Golf | Darien | Away - Woodway CC [Directions] | Staples 210, Darien 228 (W) | 2:00/5:00 | |
| Fri., 4/20 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | W 13-1 | 2:45/5:30 | |
| Fri., 4/20 | JV Baseball | Bridgeport Central | Away - Beardsley #1 [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Fri., 4/20 | FR Boys Lacrosse | Stamford | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Fri., 4/20 | V Boys Outdoor Track | New Haven Invitational | Away | Cancelled | 1:45/6:00 | ED 1:15 |
| Fri., 4/20 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 4-3 | 2:30/5:00 | |
| Fri., 4/20 | JV Boys Tennis | Wilton | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/20 | V Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Fri., 4/20 | JV Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/20 | V Softball | Bridgeport Central | Home - Wakeman Field [Directions] | W 22-3 | ||
| Fri., 4/20 | JV Softball | Bridgeport Central | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/20 | V Girls Tennis | Trumbull | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Fri., 4/20 | V Girls Water Polo | Loomis Chaffee School | Home - Staples HS Pool [Directions] | 5:00 p.m. | ||
| Sat., 4/21 | V Baseball | Masuk | Home - Staples HS Baseball Field [Directions] | L 2-4 | ||
| Sat., 4/21 | FR Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 12:00 p.m. | 10:30/1:30 | |
| Sat., 4/21 | V Boys Lacrosse | Trumbull | Home - Staples Stadium [Directions] | W 7-1 | ||
| Sat., 4/21 | JV Boys Lacrosse | Trumbull | Home - Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 4/21 | V Boys Outdoor Track | New Haven Invitational | Away | 10:00 a.m. | 7:45am | |
| Sat., 4/21 | JV Boys Rugby | Simsbury | Away [Directions] | 2:45 p.m. | 12:45/3:45 | |
| Sat., 4/21 | V Girls Lacrosse | Ridgefield | Home - Staples Stadium [Directions] | L 8-12 | ||
| Sat., 4/21 | JV Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Sat., 4/21 | V Girls Outdoor Track | New Haven Invitational | Away | 10:00 a.m. | 7:30am | |
| Sat., 4/21 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | W 4-3 | 9:15/12:30 | ED 1:45 |
| Sat., 4/21 | V Girls Water Polo | New Haven Hydras | Away - Albertus Magnus | 5:30 p.m. | 3:30/6:30 | |
| Sat., 4/21 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 12:00 p.m. | ||
| Mon., 4/23 | V Baseball | Greenwich | Home - Staples Baseball Field [Directions] | W 7-2 | ||
| Mon., 4/23 | JV Baseball | Greenwich | Home - Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 4/23 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:30 p.m. | 2:45/5:30 | |
| Mon., 4/23 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Staples 163 Trumbull 170 | 2:00/4:30 | |
| Mon., 4/23 | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Mon., 4/23 | V Boys Tennis | Norwalk | Home - Staples HS-Tennis Courts [Directions] | W 5-2 | ||
| Mon., 4/23 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-0 | 2:30/6:00 | |
| Mon., 4/23 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ride with varsity | |
| Mon., 4/23 | V Girls Golf | Trumbull | Home - Longshore [Directions] | Staples 198, Trumbull 204 (W) | ||
| Mon., 4/23 | JV Girls Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | ||
| Mon., 4/23 | FR Girls Lacrosse | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Mon., 4/23 | V Girls Outdoor Track | Stamford, Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/23 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | W 8-6 | 2:30/5:30 | |
| Mon., 4/23 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ride with varsity | |
| Mon., 4/23 | V Girls Tennis | Norwalk | Away - Norwalk HS [Directions] | W 7-0 | 2:30/5:00 | |
| Tue., 4/24 | V Baseball | Harding | Away - Beardsley Park - Baseball [Directions] | W 17-6 | 2:45/5:30 | |
| Tue., 4/24 | V Boys Golf | Fairfield Ludlowe | Home - Longshore [Directions] | Staples 149 Ludlowe 153 | ||
| Tue., 4/24 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:00 p.m. | 2:15/5:00 | smith richardson |
| Tue., 4/24 | V Boys Outdoor Track | Stamford, Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/24 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | 2:30/5:00 | |
| Tue., 4/24 | V Girls Golf | St. Joseph, Trumbull | Away - Tashua Knolls, Trumbull [Directions] | Staples 193, St Joes 283 (W) | 2:10/5:00 | |
| Tue., 4/24 | V Girls Lacrosse | New Canaan | Home - Ginny Parker Field - Staples [Directions] | L 6-17 | ||
| Tue., 4/24 | JV Girls Lacrosse | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 4/24 | V Softball | Greenwich | Home - Wakeman Field [Directions] | W 14-9 | ||
| Tue., 4/24 | JV Softball | Greenwich | Home - Staples HS - Softball Field [Directions] | 4:30 p.m. | ||
| Tue., 4/24 | V Girls Tennis | Brien McMahon | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/24 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Wed., 4/25 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | 2:45/5:30 | |
| Wed., 4/25 | V Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | W 3-1 | ||
| Wed., 4/25 | JV Boys Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/25 | FR Girls Lacrosse | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 4/25 | V Girls Water Polo | Suffield Academy | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Thu., 4/26 | V Baseball | Norwalk | Home - Staples Baseball Field [Directions] | W 12-2 | ||
| Thu., 4/26 | JV Baseball | Norwalk | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Thu., 4/26 | FR Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Thu., 4/26 | V Boys Golf | Stamford | Home - Longshore [Directions] | Staples 151 Stamford 205 | ||
| Thu., 4/26 | JV Boys Golf | Greens Farms Academy | Home - Longshore [Directions] | 3:00 p.m. | ||
| Thu., 4/26 | V Boys Lacrosse | Ridgefield | Home - Staples Stadium [Directions] | W 8 - 7 OT | ||
| Thu., 4/26 | JV Boys Lacrosse | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 4/26 | V Boys Tennis | Westhill | Away - Cummings Park Tennis Courts [Directions] | W 5-2 | 2:30/5:00 | |
| Thu., 4/26 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Staples 201,Ridgefield 191(L) | 2:00/5:00 | ed 1:45 |
| Thu., 4/26 | JV Girls Golf | Ridgefield | Away [Directions] | 3:00 p.m. | ride with varsity | ED 1:45 |
| Thu., 4/26 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | W 8-5 | 4:00/7:00 | |
| Thu., 4/26 | JV Softball | Norwalk | Away - Naramake School [Directions] | 5:30 p.m. | ride with varsity | |
| Thu., 4/26 | V Girls Tennis | Westhill | Home - Staples HS-Tennis Courts [Directions] | W 6-1 | ||
| Fri., 4/27 | FR Baseball | Brien McMahon | Home - Staples Baseball Field [Directions] | Cancelled | ||
| Fri., 4/27 | FR Boys Lacrosse | Darien | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Fri., 4/27 | V Boys Outdoor Track | Dan O'Grady Relays | Away | 4:00 p.m. | 3:45/7:00 | |
| Fri., 4/27 | V Boys Rugby | Aspetuck | Home [Directions] | 5:00 p.m. | ||
| Fri., 4/27 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | W 3-0 | 2:00/6:00 | ED 1:45 |
| Fri., 4/27 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ride with varsity | |
| Fri., 4/27 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | Cancelled | 3:00pm | |
| Fri., 4/27 | V Girls Water Polo | Greenwich | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Sat., 4/28 | V Baseball | Brien McMahon | Away - Pride Field At BMHS [Directions] | L 7-3 | 11:30/2:30 | |
| Sat., 4/28 | JV Baseball | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 10:00 a.m. | 8:30/11:30 | |
| Sat., 4/28 | FR Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 12:00 p.m. | 10:30/1:30 | |
| Sat., 4/28 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | L 6 - 11 | 5:00/8:00 | |
| Sat., 4/28 | JV Boys Lacrosse | Wilton | Away - Whitten Field [Directions] | 4:30 p.m. | 3:00/5:30 | |
| Sat., 4/28 | V Boys Outdoor Track | Dan O'Grady Relays | Away | 9:00 a.m. | 7:00am | |
| Sat., 4/28 | JV Boys Rugby | Fordham Prep (NY) | Home - Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/28 | FR Boys Rugby | Xavier | Away [Directions] | Cancelled | Yes | |
| Sat., 4/28 | JV Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | 10:00 a.m. | 8:30am/11:00am | |
| Sat., 4/28 | V Co-ed Sailing | US Coast Guard | Away | 9:00 a.m. | 8:00/4:00 | |
| Sat., 4/28 | V Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | W 16-4 | ||
| Sat., 4/28 | JV Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Sat., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 8:00 a.m. | 6:00am | |
| Sat., 4/28 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | W 6-1 | 10:30/1:00 | |
| Sat., 4/28 | JV Girls Tennis | Weston | Home - Staples HS-Tennis Courts [Directions] | 12:30 p.m. | ||
| Sat., 4/28 | V Girls Water Polo | Suffield Academy | Away | 3:15 p.m. | 12:00 | |
| Mon., 4/30 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | W 9-0 | 2:45/5:30 | |
| Mon., 4/30 | JV Baseball | Westhill | Away - Rippowam MS [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Mon., 4/30 | FR Baseball | Westhill | Home - Staples Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/30 | JV Boys Golf | Greens Farms Academy | Away - Birchwood CC | 3:30 p.m. | 2:30/5:30 | |
| Mon., 4/30 | V Boys Tennis | Stamford | Home - Staples HS-Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/30 | V Boys Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Mon., 4/30 | JV Boys Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/30 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Staples 227,NC 180(L) | 2:30/5:00 | |
| Mon., 4/30 | V Girls Outdoor Track | Danbury, Westhill | Away - Danbury HS Stadium [Directions] | 4:00 p.m. | 2:00 | 1:30 ED |
| Mon., 4/30 | V Softball | Westhill | Home - Wakeman Field [Directions] | W 11-4 | ||
| Mon., 4/30 | JV Softball | Westhill | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/30 | V Girls Tennis | Stamford | Away - Stamford HS [Directions] | W 6-1 | 2:30/5:00 | |
| Tue., 5/1 | V Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | Staples 184 Warde 189 | 2:00/4:30 | |
| Tue., 5/1 | V Boys Outdoor Track | Danbury, Westhill | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Boys Tennis | Darien | Home - Staples HS-Tennis Courts [Directions] | W 4-3 | ||
| Tue., 5/1 | JV Boys Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Girls Golf | Darien | Home - Longshore [Directions] | Staples 194, Darien 208 (W) | ||
| Tue., 5/1 | JV Girls Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | ||
| Tue., 5/1 | V Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | L 5-10 | ||
| Tue., 5/1 | JV Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 5/1 | V Softball | Brien McMahon | Home - Wakeman Field [Directions] | W 8-3 | ||
| Tue., 5/1 | JV Softball | Brien McMahon | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 2-5 | 2:30/5:00 | |
| Tue., 5/1 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Tue., 5/1 | V Girls Water Polo | Sacred Heart Academy | Home - Staples HS Pool [Directions] | 4:30 p.m. | ||
| Wed., 5/2 | V Baseball | Stamford | Home - Staples Baseball Field [Directions] | W 9-0 | ||
| Wed., 5/2 | JV Baseball | Stamford | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 5/2 | FR Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Wed., 5/2 | V Boys Golf | Ridgefield | Away - Silver Spring GC [Directions] | Staples 163 Ridgefield 174 | 1:30/4:30 | |
| Wed., 5/2 | JV Boys Golf | Greenwich | Away [Directions] | 3:00 p.m. | 2:30/5:00 | |
| Wed., 5/2 | JV Boys Lacrosse | New Canaan | Away - WTT2 [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 5/2 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 3-0 | 2:30/6:00 | |
| Wed., 5/2 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ride with varsity | |
| Wed., 5/2 | V Girls Golf | Fairfield Warde | Home - Longshore [Directions] | Staples 202,Warde 168(L) | ||
| Wed., 5/2 | JV Girls Golf | Fairfield Warde | Home - Longshore [Directions] | 3:30 p.m. | ||
| Wed., 5/2 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 5/2 | V Softball | Stamford | Away - Stamford HS [Directions] | L 0-8 | 2:30/5:30 | |
| Wed., 5/2 | JV Softball | Stamford | Away - Cummings Park [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 5/2 | V Girls Tennis | Danbury | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/3 | V Boys Golf | Norwalk | Home - Longshore [Directions] | Staples 147 Norwalk 198 | ||
| Thu., 5/3 | JV Boys Rugby | Greenwich | Away - Greenwich HS Field 7 [Directions] | 4:30 p.m. | 2:30pm/6:00 | |
| Thu., 5/3 | FR Boys Rugby | Greenwich | Away - Cos Cob Park [Directions] | 4:30 p.m. | 2:30/6:00 | |
| Thu., 5/3 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 4-2 | 2:30/5:00 | |
| Thu., 5/3 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 5/3 | V Girls Golf | Greenwich | Away - Milbrook Country Club [Directions] | Staples 207,Greenwich 188 (L) | 2:30/5:00 | |
| Thu., 5/3 | JV Girls Golf | New Canaan | Home - Longshore [Directions] | 3:15 p.m. | ||
| Thu., 5/3 | JV Girls Golf | New Canaan | Home - Long Shore [Directions] | Cancelled | ride with varsity | ED 1:45 |
| Thu., 5/3 | V Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | W 19-6 | 2:30/5:00 | |
| Thu., 5/3 | JV Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | 3:30/6:00 | |
| Thu., 5/3 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/3 | V Girls Tennis | Ridgefield | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/3 | JV Girls Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/4 | V Baseball | Darien | Home - Staples Baseball Field [Directions] | W 7-1 | ||
| Fri., 5/4 | JV Baseball | Darien | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 5/4 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Fri., 5/4 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Fri., 5/4 | V Boys Outdoor Track | Amity Midnight Invitational | Away | 5:00 p.m. | ||
| Fri., 5/4 | V Boys Rugby | Fairfield Warde | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/4 | V Boys Tennis | Trinity Catholic | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Fri., 5/4 | V Boys Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Fri., 5/4 | JV Boys Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/4 | V Girls Outdoor Track | Middletown Invitational | Away | 3:00 p.m. | 1:00/8:00 | |
| Fri., 5/4 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | W 9-3 | 2:30/5:30 | |
| Fri., 5/4 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | Cancelled | ride with varsity | |
| Fri., 5/4 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | 2:45/5:00 | |
| Fri., 5/4 | V Girls Water Polo | W-WP | Home [Directions] | 4:00 p.m. | ||
| Sat., 5/5 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | L 6 to 10 | 5:30/8:00 | |
| Sat., 5/5 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | 3:30/5:00 | |
| Sat., 5/5 | V Boys Outdoor Track | Middletown Invitational | Away - Middletown HS | 1:00 p.m. | 10:30am | |
| Sat., 5/5 | V Girls Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | W 10-4 | 5:00/7:30 | |
| Sat., 5/5 | JV Girls Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:00 p.m. | 3:30/6:00 | |
| Sat., 5/5 | V Girls Outdoor Track | Middletown Invitational | Away - Middletown HS | 12:00 p.m. | 10:30am | |
| Sat., 5/5 | V Girls Water Polo | Hopkins School | Home - Staples HS Pool [Directions] | 3:00 p.m. | ||
| Mon., 5/7 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 2-3 | 2:45/5:30 | |
| Mon., 5/7 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Mon., 5/7 | FR Baseball | Ridgefield | Home - Staples Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/7 | V Boys Golf | Norwich Free Academy Wildcat Tournament | Away | Xavier 297 Killingly 314 Staples 324 | 9:30am | ED 9:15 |
| Mon., 5/7 | V Boys Lacrosse | St. Anthonys (NY) | Home - Staples Stadium [Directions] | L 8 - 18 | ||
| Mon., 5/7 | JV Boys Lacrosse | St. Anthonys (NY) | Home - Wakeman Field B (turf) [Directions] | Cancelled | ||
| Mon., 5/7 | FR Boys Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:00/5:00 | |
| Mon., 5/7 | V Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/7 | JV Boys Tennis | Fairfield Ludlowe | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/7 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | W 3-0 | 2:30/6:00 | |
| Mon., 5/7 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Mon., 5/7 | V Girls Golf | Wilton | Home - Longshore [Directions] | Staples 194,Wilton 215 (W) | ||
| Mon., 5/7 | V Girls Outdoor Track | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | 2:30/6:00 | |
| Mon., 5/7 | V Softball | Ridgefield | Home - Wakeman Field [Directions] | W 5-2 | ||
| Mon., 5/7 | JV Softball | Ridgefield | Home - Staples HS - Softball Field [Directions] | 4:30 p.m. | ||
| Mon., 5/7 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | 2:30/5:00 | |
| Mon., 5/7 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Tue., 5/8 | JV Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | 2:15/5:00 | Darien CC |
| Tue., 5/8 | V Boys Outdoor Track | Norwalk | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/8 | V Boys Tennis | Weston | Home - Staples HS-Tennis Courts [Directions] | W 4-3 | ||
| Tue., 5/8 | V Girls Golf | Danbury | Home - Longshore [Directions] | Staples 194, Danbury 221 (W) | ||
| Tue., 5/8 | JV Girls Golf | Danbury | Home - Longshore [Directions] | 3:30 p.m. | ||
| Tue., 5/8 | V Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | L 11-15 | 5:00/8:00 | |
| Tue., 5/8 | JV Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | 5:15 p.m. | 3:30/6:30 | |
| Tue., 5/8 | FR Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 5/8 | V Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | W 5-2 | 2:30/5:00 | |
| Tue., 5/8 | JV Girls Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 3:15 p.m. | ||
| Wed., 5/9 | V Baseball | Fairfield Ludlowe | Home - Staples Baseball Field [Directions] | W 12-2 (5) | ||
| Wed., 5/9 | JV Baseball | Fairfield Ludlowe | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 5/9 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Wed., 5/9 | V Boys Golf | Wilton | Home - Longshore [Directions] | Staples 144 Wilton 170 | ||
| Wed., 5/9 | JV Boys Golf | Wilton | Home - Longshore [Directions] | 3:30 p.m. | ||
| Wed., 5/9 | FR Boys Lacrosse | Trumbull | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 5/9 | V Boys Tennis | Greenwich | Home - Staples HS-Tennis Courts [Directions] | W 4-3 | ||
| Wed., 5/9 | V Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | W 3-1 | ||
| Wed., 5/9 | JV Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/9 | V Co-ed Sailing | Fairfield Warde | Away - Pequot Yacht Club, Southport [Directions] | 4:00 p.m. | 2:15/5:00 | |
| Wed., 5/9 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | L 8-6 | 2:30/5:30 | |
| Wed., 5/9 | JV Softball | Fairfield Ludlowe | Away - Tom Haydon Field [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 5/9 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | W 7-0 | 2:30/5:00 | |
| Wed., 5/9 | V Girls Water Polo | Hopkins, Choate | Away | 2:30 p.m. | 1:00/3:30 | |
| Thu., 5/10 | V Boys Golf | Danbury, Trumbull | Away - Richter Park Golf Course [Directions] | Staples 164 Danbury 188 | 2:00/4:30 | |
| Thu., 5/10 | V Boys Lacrosse | Westhill | Home - Staples Stadium [Directions] | W 15-0 | ||
| Thu., 5/10 | JV Boys Lacrosse | Westhill | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Boys Outdoor Track | Loucks Games | Away | TBA | ||
| Thu., 5/10 | FR Boys Rugby | Aspetuck | Away - Stowe Field Shelton | 3:30 p.m. | 3:00/5:00 | |
| Thu., 5/10 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | W 7-0 | 2:30/5:00 | |
| Thu., 5/10 | JV Boys Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Girls Golf | Fairfield Ludlowe | Home - Longshore [Directions] | Staples 195, Ludlowe 183 (L) | ||
| Thu., 5/10 | JV Girls Golf | Fairfield Ludlowe | Home - Longshore [Directions] | 3:30 p.m. | Yes | |
| Thu., 5/10 | V Girls Lacrosse | Greenwich | Home - Staples Stadium [Directions] | L 9-11 | ||
| Thu., 5/10 | JV Girls Lacrosse | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Girls Tennis | New Canaan | Home - Staples HS-Tennis Courts [Directions] | W 5-2 | ||
| Fri., 5/11 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Fri., 5/11 | V Boys Outdoor Track | Irv Black Invitational | Away | 3:30 p.m. | 1:00 | |
| Fri., 5/11 | V Boys Rugby | Greenwich | Away [Directions] | 4:00 p.m. | 2:45/6:00 | JV to follow |
| Fri., 5/11 | V Boys Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Fri., 5/11 | JV Boys Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | Cancelled | ||
| Fri., 5/11 | FR Girls Lacrosse | Darien | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Fri., 5/11 | V Girls Outdoor Track | Loucks Games | Away - White Plains HS | 3:00 p.m. | 1:00pm | |
| Sat., 5/12 | V Boys Outdoor Track | Irv Black Invitational | Away | 10:00 a.m. | 7:30am | |
| Sat., 5/12 | JV Boys Rugby | New Rochelle (NY) | Home - Staples Stadium [Directions] | Cancelled | ||
| Sat., 5/12 | V Girls Outdoor Track | Loucks Games | Away - White Plains HS | 8:00 a.m. | 7:00am | |
| Mon., 5/14 | V Baseball | New Canaan | Away - Mead Park [Directions] | W 12-3 | 2:45/5:30 | |
| Mon., 5/14 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Mon., 5/14 | FR Baseball | New Canaan | Home - Staples Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/14 | V Boys Golf | Greenwich | Home - Longshore [Directions] | Staples 150 Greenwich 146 | ||
| Mon., 5/14 | JV Boys Golf | Fairfield Prep | Home - Longshore [Directions] | 3:00 p.m. | ||
| Mon., 5/14 | V Boys Outdoor Track | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/14 | V Boys Tennis | St. Joseph | Home - Staples HS-Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/14 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Mon., 5/14 | V Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Mon., 5/14 | JV Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Mon., 5/14 | JV Girls Golf | Fairfield Warde | Away - South Pine Creek- Par 3 [Directions] | 3:15 p.m. | Yes | Par 3 |
| Mon., 5/14 | JV Girls Lacrosse | Rye (NY) | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Mon., 5/14 | V Softball | New Canaan | Home - Wakeman Field [Directions] | L 0-5 | ||
| Mon., 5/14 | V Girls Tennis | St. Joseph | Away - St. Joseph HS [Directions] | W 7-0 | 2:30/5:00 | |
| Tue., 5/15 | V Baseball | St. Joseph | Home - Staples Baseball Field [Directions] | W 7-1 | ||
| Tue., 5/15 | V Boys Golf | St. Joseph | Home - Longshore [Directions] | Staples 147 St. Joseph 171 | ||
| Tue., 5/15 | V Co-ed Sailing | Indian Harbor Yacht Club | Away | TBA | 1:00 | ED 12:45 |
| Wed., 5/16 | JV Boys Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 5/16 | V Boys Lacrosse | Mamaroneck (NY) | Away | W 14-13 2OT | 2:30/5:30 | ED 2:00 |
| Wed., 5/16 | JV Boys Lacrosse | Mamaroneck (NY) | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Wed., 5/16 | V Boys Volleyball | Stamford | Away - Stamford HS [Directions] | W 3-0 | 2:30/6:00 | |
| Wed., 5/16 | JV Boys Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ride with varsity | |
| Wed., 5/16 | FR Girls Lacrosse | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Thu., 5/17 | V Boys Golf | Darien | Home - Longshore [Directions] | Staples 143 Darien 138 | ||
| Thu., 5/17 | JV Boys Golf | New Canaan | Home - Longshore [Directions] | 3:30 p.m. | ||
| Thu., 5/17 | V Boys Volleyball | Rockville | Home - Staples H.S. Gym [Directions] | W 3-0 | ||
| Thu., 5/17 | JV Boys Volleyball | Rockville | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 5/17 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | Staples 185,Wilton 193 (W) | 2:00/5:00 | |
| Thu., 5/17 | JV Girls Golf | Greenwich | Away - Milbrook Golf Club [Directions] | 3:45 p.m. | 2:20 | Millbrook CC |
| Thu., 5/17 | V Girls Outdoor Track | Greenwich | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 5/18 | FR Boys Lacrosse | Wilton | Home - Wakeman Field E (grass) [Directions] | 4:15 p.m. | ||
| Fri., 5/18 | V Boys Outdoor Track | Dream Invitational | Away | 8:00 p.m. | ||
| Fri., 5/18 | JV Boys Tennis | Weston | Home - Town Farms Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 5/18 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 18-2 | 2:00/5:00 | |
| Fri., 5/18 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | Cancelled | 4:00/7:00 | |
| Fri., 5/18 | V Girls Outdoor Track | Dream Invitational | Away - Danbury HS | Cancelled | 3:00pm | |
| Fri., 5/18 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | L 2-10 | 2:30/5:30 | |
| Fri., 5/18 | JV Softball | St. Joseph | Away - Long Hill Administration field, Trumbull CT [Directions] | 4:00 p.m. | ride with varsity | |
| Sat., 5/19 | FR Boys Rugby | Fordham Prep (NY) | Home - Staples Stadium [Directions] | 12:30 p.m. | ||
| Mon., 5/21 | JV Baseball | St. Joseph | Home - Wakeman Field [Directions] | Cancelled | ||
| Mon., 5/21 | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | Cancelled | 2:45/5:30 | |
| Mon., 5/21 | V Girls Golf | Ridgefield | Home - Longshore [Directions] | Staples 201,Ridgefield 186(L) | ||
| Mon., 5/21 | JV Girls Golf | Ridgefield | Home - Longshore [Directions] | 3:30 p.m. | ||
| Tue., 5/22 | V Boys Golf | New Canaan, Danbury | Away - Country Club of New Canaan [Directions] | Staples 166 New Canaan 168 | 2:30/4:30 | |
| Tue., 5/22 | JV Boys Golf | Greenwich | Home - Longshore [Directions] | 3:30 p.m. | ||
| Wed., 5/23 | V Boys Golf | Brien McMahon | Home - Longshore [Directions] | Staples 141 McMahon 216 | ||
| Wed., 5/23 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Cancelled | 2:00/5:00 | ED 1:50 |
| Wed., 5/23 | FR Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | 2:30/5:00 | |
| Wed., 5/23 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Staples 217,Warde 180 (L) | Yes | |
| Tue., 5/29 | JV Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | 2:15/5:00 | |
| Tue., 5/29 | V Girls Golf | New Canaan | Away - Fairchild Wheeler [Directions] | Staples 206, NC 177 (L) | 1:40 | ED 1:30 |
| Tue., 5/29 | Unified Sports Track | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | 2:30 | wheelchair bus for 1, must stay |