| Staples 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 542 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Bus Time (Company) | Note |
| TBA | JV Baseball | Masuk | Away - Wolfe Park [Directions] | 12:00 p.m. | 10:30/1:30 | |
| TBA | JV Boys Golf | Greenwich | Away [Directions] | TBA | 2:00 | ED 1:50 |
| TBA | FR Boys Lacrosse | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| TBA | V Boys Outdoor Track | Irv Black Invitational @ Willowbrook Park | Away | 3:30 p.m. | 1:00 | ED 12:30 |
| TBA | V Boys Outdoor Track | Hatter Freshmen Invitational | Away | 4:00 p.m. | 2:00 | ED 1:30 |
| TBA | V Co-ed Sailing | FLHS, Stamford, MHS | Away | TBA | 2:15/5:45 | Pequot Yacht Club |
| TBA | V Girls Gymnastics | Westhill, New Canaan | Away [Directions] | 5:30 p.m. | 4:00/6:30 | |
| TBA | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | TBA | 2:45/5:00 | |
| TBA | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | TBA | p/u 2:30, d/o 6:00 | |
| TBA | V Girls Water Polo | Chelsea Piers | Away | 6:45 p.m. | 4:45 | |
| Tue., 9/9 | V Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | 2:10/5:00 | ED 2:00 |
| Tue., 9/9 | JV Field Hockey | Danbury | Away - Danbury High School Grass Field [Directions] | 5:30 p.m. | 3:30/6:30 | |
| Wed., 9/10 | V Boys Water Polo | Brunswick School | Away | 4:00 p.m. | 2:30/5:30 | JV to follow |
| Wed., 9/10 | V Girls Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | 4:00 p.m. | 2:30/5:00 | |
| Wed., 9/10 | JV Girls Soccer | Harding | Away - Seaside Park [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Wed., 9/10 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | 2:45/6:00 | |
| Wed., 9/10 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:15 p.m. | ride with varsity | |
| Thu., 9/11 | FR Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Fri., 9/12 | FR Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 9/12 | V Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 5:30 p.m. | 2:30/6:00 | |
| Fri., 9/12 | JV Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ride with varsity | |
| Sat., 9/13 | V Boys Cross Country | Invitational | Away | TBA | 7:00am | |
| Sat., 9/13 | V Boys Water Polo | Darien | Away [Directions] | 3:30 p.m. | 2:15 | |
| Sat., 9/13 | FR Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | Cancelled | 9:45/12:00 | |
| Mon., 9/15 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | 2:45/6:00 | |
| Mon., 9/15 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | ride with varsity | |
| Tue., 9/16 | V Boys Cross Country | New Canaan, Trinity Catholic, Norwalk, Brien McMahon | Away - Waveny Park [Directions] | 4:00 p.m. | 1:45 | ED 1:15, 2 buses |
| Tue., 9/16 | V Boys Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 6:00 p.m. | 3:30/7:00 | |
| Tue., 9/16 | JV Boys Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 6:00 p.m. | 4:15/7:00 | |
| Tue., 9/16 | V Girls Cross Country | New Canaan, Trinity Catholic, Norwalk, Brien McMahon | Away - Waveny Park [Directions] | 4:00 p.m. | 1:45/5:00 | ED 1:15 2 buses |
| Tue., 9/16 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:00 p.m. | 2:10/5:00 | ED 2:00 |
| Wed., 9/17 | FR Girls Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 9/17 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 9/18 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | 5:00/8:00 | |
| Thu., 9/18 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | 4:00/6:30 | |
| Fri., 9/19 | V Football | Wilton | Away - Fujitani Field - Turf [Directions] | 7:00 p.m. | 5:00/9:00 | 2 buses |
| Fri., 9/19 | V Competitive Cheerleading | Wilton | Away [Directions] | 7:00 p.m. | 5:30/8:30 | |
| Fri., 9/19 | FR Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 5:00 p.m. | 3:00/6:00 | |
| Fri., 9/19 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 9/20 | V Boys Cross Country | Stratton Brook Invitational | Away | 9:00 a.m. | 8:00am | |
| Sat., 9/20 | V Girls Cross Country | Stratton Brook Invitational | Away | 9:00 a.m. | 8:00am | 2 buses |
| Sat., 9/20 | JV Girls Swimming and Diving | Greenwich | Away [Directions] | 11:00 a.m. | 9:30/12:00 | |
| Mon., 9/22 | JV Football | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Mon., 9/22 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | 3:45/7:00 | |
| Mon., 9/22 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 9/22 | V Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | 2:45/6:00 | |
| Mon., 9/22 | JV Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | ride with varsity | |
| Tue., 9/23 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:15 p.m. | 5:45/8:15 | |
| Tue., 9/23 | JV Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 5:15 p.m. | 4:15 | shuttle with varsity |
| Tue., 9/23 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:50/5:00 | |
| Tue., 9/23 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Tue., 9/23 | JV Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:00 p.m. | 3:00/5:00 | |
| Tue., 9/23 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | 2:45/6:00 | |
| Tue., 9/23 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Wed., 9/24 | FR Football | Westhill | Away - Rippowam Middle School - Turf Field [Directions] | 3:00 p.m. | 2:00/4:00 | ED 1:45 |
| Wed., 9/24 | V Girls Swimming and Diving | Wilton | Away - Allen's Field [Directions] | 3:00 p.m. | 2:00/4:00 | ED 1:50 |
| Fri., 9/26 | V Boys Water Polo | Greenwich | Away [Directions] | TBA | Yes | |
| Fri., 9/26 | FR Field Hockey | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | 2:50/5:00 | |
| Fri., 9/26 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 9/26 | JV Girls Soccer | Bassick | Away [Directions] | 4:00 p.m. | 3:00/5:00 | |
| Sat., 9/27 | V Boys Water Polo | Greenwich | Away [Directions] | TBA | Yes | |
| Sun., 9/28 | V Boys Water Polo | Greenwich | Away [Directions] | TBA | Yes | |
| Mon., 9/29 | FR Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 9/30 | V Boys Cross Country | Fairfield Ludlowe, Ridgefield, Bassick, Trumbull, Bridgeport Central | Away [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:30 2 buses |
| Tue., 9/30 | FR Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 9/30 | V Girls Cross Country | Fairfield Ludlowe, Ridgefield, Bassick, Trumbull, Bridgeport Central | Away [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:30 2 buses |
| Wed., 10/1 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Wed., 10/1 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Thu., 10/2 | FR Football | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 10/2 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 5:00 p.m. | 3:30/6:00 | |
| Thu., 10/2 | JV Field Hockey | Norwalk | Away - NHS Grass Field [Directions] | 3:30 p.m. | 2:30 | Shuttle with varsity |
| Thu., 10/2 | FR Girls Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 10/2 | FR Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 10/6 | FR Boys Soccer | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 10/6 | JV Girls Swimming and Diving | Greenwich | Away [Directions] | TBA | 2:30/5:00 | |
| Mon., 10/6 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 10/7 | V Boys Cross Country | St. Joseph, Danbury, Darien | Away - St. Joseph High School [Directions] | 4:00 p.m. | 1:45/5:00 | ED 1:15 2 buses |
| Tue., 10/7 | V Girls Cross Country | St. Joseph, Danbury, Darien | Away [Directions] | 4:00 p.m. | 1:45/5:00 | ED 1:15 2 buses |
| Tue., 10/7 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Wed., 10/8 | V Field Hockey | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Wed., 10/8 | JV Field Hockey | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | d/o 4:00, d/o 6:30 | |
| Wed., 10/8 | V Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | p/u 2:10/d/o 6:00 | ED 1:55 |
| Wed., 10/8 | JV Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:30 p.m. | ride with varsity | ED 1:55 |
| Thu., 10/9 | V Girls Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Thu., 10/9 | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Fri., 10/10 | V Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | d/0 5:00, p/u 8:00 | 2 buses |
| Fri., 10/10 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 3:45 p.m. | 2:15/5:00 | ED 2:00 |
| Fri., 10/10 | JV Boys Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 3:45 p.m. | p/u 2:30,d/o 5:00 | |
| Fri., 10/10 | V Boys Water Polo | Horace Mann (NY) | Away | 5:00 p.m. | 2:30 | JV to Follow |
| Fri., 10/10 | V Competitive Cheerleading | Fairfield Ludlowe | Away [Directions] | 7:00 p.m. | 5:30/8:30 | |
| Fri., 10/10 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | 4:00 p.m. | 2:50/5:00 | |
| Fri., 10/10 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | ride with varsity | |
| Sat., 10/11 | V Boys Cross Country | Wickham Park Invitational | Away | 9:40 a.m. | 7:00am | |
| Sat., 10/11 | V Boys Water Polo | Suffield | Away [Directions] | 3:30 p.m. | 1:30/5:00 | |
| Mon., 10/13 | JV Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 6:30 p.m. | 5:00/7:30 | |
| Mon., 10/13 | FR Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Tue., 10/14 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 |
| Tue., 10/14 | JV Girls Soccer | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | 2:15/5:00 | ED 2:00 |
| Wed., 10/15 | FR Boys Soccer | Greenwich | Away - GHS Field 7 [Directions] | 4:30 p.m. | p/u 3:00,d/o 5:30 | |
| Wed., 10/15 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | 2:50/5:00 | |
| Wed., 10/15 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | p/u 1:45, d/o 4:00 | ED 1:30 |
| Wed., 10/15 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Fri., 10/17 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Fri., 10/17 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | 3:45/6:30 | |
| Fri., 10/17 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 |
| Fri., 10/17 | V Girls Volleyball | Wilton | Away - Wilton High School Field House [Directions] | 5:30 p.m. | 3:00/6:00 | |
| Fri., 10/17 | JV Girls Volleyball | Wilton | Away - Wilton High School Field House [Directions] | 4:30 p.m. | ride with varsity | |
| Sat., 10/18 | V Football | Danbury | Away - Danbury High School Stadium [Directions] | 1:30 p.m. | 11:30/3:00 | |
| Sat., 10/18 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:15/5:00 | |
| Sat., 10/18 | JV Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 10/18 | V Competitive Cheerleading | Danbury | Away [Directions] | 1:30 p.m. | 11:30/3:00 | |
| Mon., 10/20 | V Boys Cross Country | FCIAC Championship @ Waveny Park | Away | 2:15 p.m. | 12:00/3:30 | ED 11:30 2 buses |
| Mon., 10/20 | JV Football | Danbury | Away - Danbury High School Stadium [Directions] | 3:45 p.m. | 2:30/5:00 | |
| Mon., 10/20 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | 5:15/8:00 | |
| Mon., 10/20 | JV Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Mon., 10/20 | V Girls Cross Country | FCIAC Championship @ Waveny Park | Away | 2:15 p.m. | 12:00/3:30 | ED 11:30 2 buses |
| Mon., 10/20 | FR Girls Soccer | Fairfield Ludlowe | Away - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Mon., 10/20 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | 2:00/4:15 | |
| Mon., 10/20 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | p/u 2:30,d/o 6:00 | |
| Mon., 10/20 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ride with varsity | |
| Tue., 10/21 | V Boys Cross Country | Bethel JV Invitational | Away | Cancelled | 2:00 | ED 1:30 1 bus |
| Tue., 10/21 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 10/21 | V Girls Cross Country | Bethel JV Invitational | Away | Cancelled | 2:00/5:00 | ED 1:30 |
| Tue., 10/21 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:00 | |
| Tue., 10/21 | JV Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Wed., 10/22 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 6:00 p.m. | 4:30/7:00 | |
| Wed., 10/22 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:30 p.m. | 3:15 | shuttle with varsity |
| Wed., 10/22 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 10/23 | V Boys Cross Country | Danbury Freshmen Invitational | Away | 3:45 p.m. | 2:00 | ED 1:30 |
| Thu., 10/23 | V Girls Cross Country | Danbury Freshmen Invitational | Away | 3:45 p.m. | 2:00/5:00 | ED 1:30 |
| Thu., 10/23 | JV Girls Soccer | Westhill | Away - Rippowam Middle School [Directions] | Cancelled | 2:45/5:00 | |
| Fri., 10/24 | V Football | New Canaan | Away - Dunning Stadium [Directions] | 7:00 p.m. | 5:00/9:00 | |
| Fri., 10/24 | V Boys Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 5:30 p.m. | 3:15/6:30 | |
| Fri., 10/24 | V Boys Water Polo | Choate Rosemary Hall | Away | 4:00 p.m. | 2:00/6:00 | |
| Fri., 10/24 | V Competitive Cheerleading | New Canaan | Away [Directions] | 7:00 p.m. | 5:30/8:30 | |
| Fri., 10/24 | FR Field Hockey | Wilton | Away - Allen's Field [Directions] | 5:00 p.m. | 2:50/5:00 | |
| Fri., 10/24 | FR Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 10/25 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 1:00 p.m. | 9:30am | |
| Sat., 10/25 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 1:00 p.m. | 9:30am | |
| Sat., 10/25 | JV Girls Swimming and Diving | JV SWIMMING FCIAC | Away | 4:00 p.m. | 2:00 | |
| Mon., 10/27 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Mon., 10/27 | V Boys Soccer | Greenwich | Away [Directions] | 5:00 p.m. | 3:15/6:00 | |
| Mon., 10/27 | FR Field Hockey | Ridgefield | Away [Directions] | Cancelled | 2:50/5:00 | |
| Mon., 10/27 | V Girls Soccer | New Canaan | Away [Directions] | 5:00 p.m. | 3:15/6:00 | |
| Tue., 10/28 | V Field Hockey | FCIAC Semi-final vs. Darien @ Brien McMahon | Away | 7:00 p.m. | 5:15/8:00 | |
| Tue., 10/28 | V Girls Swimming and Diving | FCIAC Trials @ Greenwich | Away | 4:00 p.m. | 2:00/6:00 | ED 1:45 |
| Wed., 10/29 | SO Football | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | 2:00 | |
| Wed., 10/29 | V Girls Soccer | Fairfield Warde | Away [Directions] | 4:30 p.m. | 2:45/5:30 | |
| Thu., 10/30 | FR Football | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | p/u 3:30, d/o 6:30 | |
| Thu., 10/30 | V Girls Swimming and Diving | FCIAC Finals @ Greenwich | Away | 4:00 p.m. | 2:00/6:00 | ED 1:45 |
| Fri., 10/31 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | 10:30 | ED 10:30 |
| Fri., 10/31 | V Boys Water Polo | Loomis Chaffee School | Away | 4:30 p.m. | 2:30/6:30 | JV to follow at 5:45 |
| Fri., 10/31 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | 10:30 | ED 10:30 |
| Sat., 11/1 | V Boys Water Polo | Hopkins School | Away | 10:30 a.m. | 9:00am | |
| Mon., 11/3 | V Boys Soccer | East Hartford | Away [Directions] | 4:00 p.m. | 1:00 | ED 12:45 |
| Mon., 11/3 | V Boys Water Polo | Hotchkiss | Away | 4:30 p.m. | 1:45 | ED 1:30 |
| Mon., 11/3 | V Girls Volleyball | Class LL First Round vs. Trumbull | Away | 3:30 p.m. | 2:00 | ED 1:45 |
| Wed., 11/5 | V Boys Soccer | West Haven | Away [Directions] | 6:30 p.m. | 4:00 | |
| Wed., 11/5 | V Boys Water Polo | Hopkins School | Away | Cancelled | 1:45/4:30 | |
| Thu., 11/6 | FR Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | p/u 2:30,d/o 5:30 | |
| Fri., 11/7 | V Boys Soccer | Darien | Away [Directions] | 2:00 p.m. | 11:45/3:00 | ED 11:45 |
| Fri., 11/7 | V Field Hockey | CIAC Class L Quarterfinals vs. Glastonbury | Away | 2:00 p.m. | 11:45 | ED 11:30 |
| Sat., 11/8 | V Boys Cross Country | New England Championship | Away - Wickham Park - East Hartford [Directions] | TBA | 8:00am | |
| Sat., 11/8 | V Girls Cross Country | New England Championship | Away - Wickham Park - East Hartford [Directions] | 11:00 a.m. | 8:00am | |
| Sat., 11/8 | V Girls Soccer | CIAC Class LL Quarterfinal vs. Glastonbury | Away | 2:00 p.m. | 11:00/3:00 | |
| Sat., 11/8 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 6:00 p.m. | 2:30/8:00 | |
| Wed., 11/12 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan Univ. [Directions] | 7:00 p.m. | 3:30/9:00 | |
| Fri., 11/14 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | 5:00/9:00 | |
| Fri., 11/14 | V Competitive Cheerleading | Norwalk | Away [Directions] | 7:00 p.m. | 5:30/8:30 | |
| Sat., 11/15 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:30 p.m. | 5:00/9:30 | |
| Thu., 11/27 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | 8:00am/12:00pm | 2 buses |
| Thu., 11/27 | V Competitive Cheerleading | Greenwich | Away [Directions] | 10:00 a.m. | 8:00am/11:30 | |
| Fri., 12/12 | V Girls Basketball | Westhill | Away [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Fri., 12/12 | FR Girls Basketball | Westhill | Away [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Sat., 12/13 | JV Girls Ice Hockey | Fairfield Warde | Away [Directions] | 3:00 p.m. | 1:30 pm | |
| Wed., 12/17 | V Boys Ice Hockey | Northeastern Shamrocks | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | 2:45/7:00 | Bus to leave Staples at 3:00 |
| Wed., 12/17 | V Boys Swimming and Diving | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 12/17 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 8:30 p.m. | 6:30/9:30 | small bus is OK |
| Wed., 12/17 | JV Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 8:30 p.m.p.m. | 6:30 pm | |
| Thu., 12/18 | V Girls Gymnastics | Greenwich, Weston | Away [Directions] | 6:30 p.m. | 4:30/7:30 | |
| Thu., 12/18 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford [Directions] | 8:30 p.m. | 6:00 pm | |
| Thu., 12/18 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford [Directions] | 8:30 p.m. | TBA | |
| Thu., 12/18 | JV Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford [Directions] | 8:30 p.m. | 6:30 pm | |
| Fri., 12/19 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Fri., 12/19 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:45 | Shuttle with varsity |
| Fri., 12/19 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 5:30 p.m. | 3:15/6:30 | |
| Fri., 12/19 | V Girls Indoor Track | New Haven Invitational @ Floyd Little Center | Away | Cancelled | Yes | |
| Sat., 12/20 | V Boys Ice Hockey | Norwich Free Academy | Away - Norwich Ice Rink [Directions] | 5:15 p.m. | 2:15/6:15 | Bus to leave Staples at 2:30 |
| Sat., 12/20 | V Wrestling | Ludlowe Invitational | Away | 9:00 a.m. | 7:30/7:30 | |
| Mon., 12/22 | V Girls Basketball | Stamford | Away - Stamford High School [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Mon., 12/22 | FR Girls Basketball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 12/23 | V Boys Ice Hockey | Wethersfield | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | 5:30/9:00 | Bus to leave Staples at 5:45 |
| Tue., 12/23 | V Wrestling | Bridgeport Central | Away - Cafe [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 12/27 | V Boys Ice Hockey | Westhill/Stamford | Away [Directions] | 5:40 p.m. | 3:15/6:40 | Bus to leave Staples at 3:30 |
| Sat., 12/27 | V Boys Indoor Track | Hillhouse Winter Relays | Away | 10:00 a.m. | 7:45 | |
| Sat., 12/27 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 12:00 p.m. | 10:30/1:00 | |
| Sat., 12/27 | V Girls Indoor Track | Rhode Island Classic @ Providence Career & Tech HS | Away | 8:00 a.m. | yes | 12/26/14 Activity bus - leave Staples at 12:30, drop at Providence Biltmore, 11 Dorrance Street, Providence, RI, Driver returns to Connecticut 12/27/14 Charter # 155784 Leave Biltmore at 7:00am, go to Providence Career and Tech HS, 41 Fricker Street, Prov |
| Mon., 12/29 | V Boys Basketball | Wilton | Away - Wilton High School Field House [Directions] | 7:00 p.m. | TBA | |
| Mon., 12/29 | V Girls Basketball | Greenwich | Away [Directions] | TBA | 11:30 | |
| Tue., 12/30 | V Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | 2:00 p.m. | 10:30/3:00 | Bus to leave Staples at 10:45 |
| Tue., 12/30 | V Wrestling | Danbury, New Canaan, Fairfield Ludlowe | Away [Directions] | 9:00 a.m. | 7:00am/1:00pm | |
| Thu., 1/1 | V Boys Ice Hockey | Norwich Free Academy | Home - Longshore [Directions] | 6:00 p.m. | 3:45/7:00 | Bus to leave Staples at 4:00 |
| Sat., 1/3 | V Wrestling | Bunnell Duals | Away | 10:00 a.m. | 8:30am | |
| Sat., 1/3 | V Girls Gymnastics | Pomperaug Invitational | Away | 9:00 a.m. | 7:00am | |
| Tue., 1/6 | V Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Tue., 1/6 | FR Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 1/7 | V Boys Alpine Skiing | Greenwich, Amity, Wilton, Glastonbury | Away | 4:00 p.m. | 2:15 | ED 2:00 |
| Wed., 1/7 | V Girls Ice Hockey | Greenwich | Away [Directions] | 8:30 p.m. | 6:30 pm | |
| Wed., 1/7 | JV Girls Ice Hockey | Greenwich | Away [Directions] | 8:30 p.m. | 7:00 pm | |
| Fri., 1/9 | V Boys Basketball | Fairfield Warde | Away [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Fri., 1/9 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | 2:45 | Shuttle with varsity |
| Sat., 1/10 | V Boys Ice Hockey | New Canaan | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | 5:30/9:00 | Bus to leave at 5:45 |
| Sat., 1/10 | V Girls Gymnastics | Trumbull, Wilton | Away - Next Dimension Gymnastics [Directions] | 6:00 p.m. | 4:30/7:00 | |
| Sat., 1/10 | V Girls Indoor Track | SCC Invitational Floyd Little Center | Away | 9:00 a.m. | 7:00am | extra large bus please |
| Tue., 1/13 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | 3:45/8:00 | |
| Tue., 1/13 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 1/14 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | 5:45/9:30 | Bus to leave Staples at 6:00 |
| Thu., 1/15 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 4:30/7:30 | |
| Fri., 1/16 | V Boys Indoor Track | Yale Invitational | Away | 1:00 p.m. | 10:45 | |
| Fri., 1/16 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | 1:45/4:30 | ED 1:30 |
| Fri., 1/16 | V Girls Basketball | Wilton | Away - Wilton High School Field House [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Fri., 1/16 | FR Girls Basketball | Wilton | Away - Wilton High School Field House [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 1/16 | V Girls Indoor Track | Yale Invitational @ Cox Cage | Away | 12:00 p.m. | 11:00am | |
| Fri., 1/16 | V Girls Indoor Track | East Coast Classic @ Providence Career & Tech HS | Away | Cancelled | 1:00pm | Activity bus if possible |
| Sat., 1/17 | V Boys Ice Hockey | Stamford | Home - Milford Ice Pavilion [Directions] | 3:00 p.m. | 12:30/4:00 | Bus to leave Staples at 12:45 |
| Sat., 1/17 | V Boys Indoor Track | Yale Invitational | Away | 9:00 a.m. | 8:00 | |
| Sat., 1/17 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Ice Rink [Directions] | 8:30 p.m. | 6:30 pm | |
| Sat., 1/17 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Ice Rink [Directions] | 8:30 p.m. | 6:30 pm | |
| Sat., 1/17 | V Girls Indoor Track | East Coast Classic @ Providence Career & Tech HS | Away | Cancelled | 6:00am | activity bus if possible |
| Mon., 1/19 | V Girls Ice Hockey | Daniel Hand Coop | Away - Daniel Hand [Directions] | 3:45 p.m. | 1:30 pm | |
| Mon., 1/19 | JV Girls Ice Hockey | Daniel Hand Coop | Away - Daniel Hand [Directions] | 3:45 p.m. | 1:45 PM | |
| Tue., 1/20 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:00 p.m. | 1:45/5:00 | Early Dismissal 1:45, Bus to leave Staples at 2:00 |
| Tue., 1/20 | V Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | 4:00/8:00 | |
| Wed., 1/21 | V Boys Alpine Skiing | Darien, Farmington, Pomperaug, Ridgefield | Away | 4:00 p.m. | 2:15 | ED 2:00 |
| Wed., 1/21 | V Wrestling | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | 4:15/7:00 | |
| Thu., 1/22 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 |
| Thu., 1/22 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | 2:30/6:30 | |
| Thu., 1/22 | V Girls Gymnastics | Wilton, Darien | Away - Wilton High School Aux. Gym [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Fri., 1/23 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 4:00 p.m. | 1:30/5:00 | Early Dismissal 1:30, Bus to leave Staples at 1:45 |
| Fri., 1/23 | V Girls Gymnastics | Oxford, Newtown, Pomperaug | Away - Kinetic Kids--Oxford [Directions] | 7:00 p.m. | 5:15/8:00 | |
| Sat., 1/24 | V Girls Indoor Track | SCC Invitational @ Floyd Athletic Center | Away | Cancelled | 12:15 | |
| Sun., 1/25 | V Boys Indoor Track | SCC Coaches Invitational | Away | 9:00 a.m. | 6:45 | |
| Wed., 1/28 | V Boys Alpine Skiing | Fairfield, Cheshire, Litchfield, Hopkins | Away | 4:00 p.m. | 2:15 | ED 2:00 |
| Wed., 1/28 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | 3:45/8:00 | |
| Wed., 1/28 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 1/28 | V Wrestling | Stamford | Away - Stamford High Aux Gym [Directions] | 6:00 p.m. | 4:15/7:00 | |
| Wed., 1/28 | JV Girls Ice Hockey | Darien | Away [Directions] | 7:40 p.m. | 5:30 pm | |
| Thu., 1/29 | V Competitive Cheerleading | ALl FCIAC & Partner Stunt Competition | Away | 6:00 p.m. | 3:15/8:00 | |
| Fri., 1/30 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Fri., 1/30 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30 | Shuttle with varsity |
| Fri., 1/30 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Sat., 1/31 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | 5:45/9:00 | Bus to leave Staples at 6:00 |
| Sat., 1/31 | V Competitive Cheerleading | 1st Annual Battle at St Joe's | Away | 12:00 p.m. | 8:15 | |
| Tue., 2/3 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | 5:45 p.m. | 2:30/6:45 | |
| Tue., 2/3 | V Girls Gymnastics | Pomperaug, Nonnewaug | Away - Auxiliary Gym [Directions] | 6:00 p.m. | 4:00pm | |
| Wed., 2/4 | V Boys Ice Hockey | Norwalk | Home - Milford Ice Pavilion [Directions] | 4:00 p.m. | 1:30/5:00 | Early Dismissal 1:30, Bus to leave Staples at 1:45 |
| Wed., 2/4 | V Wrestling | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 3:15/6:00 | |
| Thu., 2/5 | V Boys Alpine Skiing | Fairfield Prep, Westbrook, Branford, Westhill, Gilbert, New Canaan, St Luke | Away | 4:00 p.m. | 2:15 | ED 2:00 |
| Thu., 2/5 | V Boys Indoor Track | FCIAC Championship @ Hillhouse | Away | 4:30 p.m. | 2:00 | ED 1:30 |
| Thu., 2/5 | V Girls Indoor Track | FCIAC Championship @ Hillhouse | Away | 4:30 p.m. | 2:00pm | |
| Fri., 2/6 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Fri., 2/6 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 2/6 | V Girls Gymnastics | New Milford | Away - New Milford High School [Directions] | 5:00 p.m. | 3:00/6:00 | |
| Sat., 2/7 | V Boys Ice Hockey | St. Joseph | Home - Milford Ice Pavilion [Directions] | 3:00 p.m. | 12:45/4:00 | Bus to leave at 1:00 |
| Sat., 2/7 | V Competitive Cheerleading | 2015 FCIAC Varsity and JV Cheerleading Competition | Away | 11:00 a.m. | 8:15/2:30 | |
| Sat., 2/7 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away [Directions] | 11:50 a.m.m. | 10:00 am | |
| Tue., 2/10 | V Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 7:00 p.m. | 3:45/8:00 | |
| Tue., 2/10 | FR Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 2/10 | V Boys Ice Hockey | Trinity Catholic | Home - Milford Ice Pavilion [Directions] | 4:15 p.m. | 1:30/5:15 | Bus to leave Staples |
| Tue., 2/10 | V Girls Gymnastics | Fairfield Warde, Fairfield Ludlowe | Away - Gymnastics & Cheer Academy [Directions] | 6:30 p.m. | 5:15/8:00 | |
| Wed., 2/11 | V Boys Ice Hockey | Darien | Home - Milford Ice Pavilion [Directions] | 4:00 p.m. | 1:15/5:00 | Early Dismissal 1:15, Bus to leave at 1:30 |
| Wed., 2/11 | V Girls Gymnastics | Westhill | Away - Westhill - New Gymnasium [Directions] | 5:30 p.m. | 4:00pm/6:30 | |
| Wed., 2/11 | JV Girls Ice Hockey | New Canaan | Away [Directions] | 6:00 p.m. | 4:30 pm | |
| Thu., 2/12 | V Boys Alpine Skiing | Barlow, Danbury, Southington, Guilford, Cheshire Academy, Weston | Away | 4:00 p.m. | 2:15 | ED 2:00 |
| Thu., 2/12 | V Girls Basketball | Bassick | Away [Directions] | 3:30 p.m. | 2:15/4:30 | |
| Fri., 2/13 | V Wrestling | FCIAC Championship @ New Canaan | Away | 4:00 p.m. | 1:00pm | |
| Fri., 2/13 | FR Girls Basketball | Bassick | Away [Directions] | Cancelled | 2:30/5:00 | |
| Sat., 2/14 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:30 p.m. | 1:00 | |
| Sat., 2/14 | V Wrestling | FCIAC Championship @ New Canaan | Away | 9:00 a.m. | 7:00am | |
| Sat., 2/14 | V Girls Gymnastics | FCIAC CHampionship | Away | 10:30 a.m. | 8:15 | |
| Sat., 2/14 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:30 p.m. | 1:00 | |
| Mon., 2/16 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Mon., 2/16 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:30 p.m. | 2:20/5:00 | |
| Mon., 2/16 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 3:10 p.m. | 12:30/4:10 | Bus to leave Staples at 12:45 |
| Wed., 2/18 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Wed., 2/18 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 2:30 | Shuttle with varsity |
| Thu., 2/19 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavilion [Directions] | 4:15 p.m. | 1:30/7:30 | Bus to leave Staples at 1:45 |
| Fri., 2/20 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:00 p.m. | 2:00 | |
| Fri., 2/20 | JV Girls Ice Hockey | Masuk Coop | Away - Shelton Ice rink [Directions] | 4:20 p.m. | 2:30 pm | |
| Sat., 2/21 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury [Directions] | 11:50 a.m. | 8:45/1:00 | Bus to leave Staples at 9:15 |
| Sat., 2/21 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | 7:30 | |
| Sat., 2/21 | JV Boys Swimming and Diving | JV FCIAC Championship @ Greenwich HS | Away | 1:30 p.m. | 11:00/3:00 | |
| Sat., 2/21 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | 7:15 am | |
| Sat., 2/21 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | 7:30am | |
| Mon., 2/23 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 7:00 p.m. | 4:00/8:00 | |
| Mon., 2/23 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | 2:30 | Shuttle with varsity |
| Tue., 2/24 | V Boys Swimming and Diving | FCIAC Trials @ Greenwich HS | Away | 4:30 p.m. | 2:15 | ED 2:00 |
| Wed., 2/25 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 7:15 p.m. | 4:30/8:15 | Bus to leave Staples at 4:45 |
| Thu., 2/26 | V Boys Swimming and Diving | FCIAC Finals | Away | 6:30 p.m. | 4:00/8:30 | |
| Fri., 2/27 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | 11:30 | ED 11:00 |
| Fri., 2/27 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 12:30/6:00 | |
| Fri., 2/27 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | 11:00am | coach bus |
| Sat., 2/28 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | 7:15am | |
| Sat., 2/28 | V Competitive Cheerleading | Best Cheerleading Competition | Away | 3:30 p.m. | 12:45 | |
| Sat., 2/28 | V Girls Gymnastics | States @ Pomperaug | Away | TBA | 11:15 | |
| Wed., 3/4 | V Girls Basketball | Career Magnet | Away [Directions] | 7:00 p.m. | 4:45/8:00 | |
| Fri., 3/6 | V Wrestling | New England Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | Yes | |
| Sat., 3/7 | V Competitive Cheerleading | Class LL State Competition | Away [Directions] | 4:00 p.m. | 12:45 | |
| Mon., 3/9 | V Boys Alpine Skiing | States | Away | TBA | 10:45 | ED 10:30 |
| Mon., 3/9 | V Boys Basketball | Class LL CIAC First Round vs. Hillhouse HS | Away | 7:00 p.m. | 4:15/8:00 | |
| Mon., 3/9 | V Boys Ice Hockey | Division III Ice Hockey vs Barlow | Home - Milford Ice Pavilion [Directions] | 7:00 p.m. | 4:30/8:00 | |
| Mon., 3/9 | V Girls Alpine Skiing | States | Away | TBA | 10:45 | ED 10:30 |
| Thu., 3/12 | V Boys Ice Hockey | Division III Quarterfinal vs. EOS/Tolland @ West Haven Rink | Away | 6:00 p.m. | 2:30/7:00 | |
| Sat., 3/14 | V Boys Indoor Track | New Balance Indoor Nationals | Away | TBA | 1:00/7:00 | 8:00am |
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Class LL Qualifying | Away - Hamden HS [Directions] | 3:30 p.m. | 12:00 | |
| Tue., 3/17 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | 3:30 | |
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | 12:00 | |
| Wed., 4/1 | V Girls Water Polo | Greenwich | Away [Directions] | 3:00 p.m. | 1:30 | ED 1:20 |
| Thu., 4/2 | V Boys Rugby | Ridgefield | Away [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Tue., 4/7 | V Co-ed Sailing | Make up regatta at Grass Island | Away | 4:00 p.m. | 2:15/6:00 | |
| Wed., 4/8 | FR Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | 4:00 p.m. | 2:30pm/5:00pm | |
| Wed., 4/8 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:15 p.m. | 5:30/8:15 | |
| Wed., 4/8 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | 3:45/6:30 | |
| Wed., 4/8 | V Co-ed Sailing | GHS, RCDS, DHS | Away | 3:00 p.m. | 2:15/5:45 | Grass Island |
| Wed., 4/8 | V Girls Tennis | Norwalk | Away - Norwalk High School [Directions] | 4:00 p.m. | 2:30pm/5:00pm | |
| Wed., 4/8 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Thu., 4/9 | V Boys Rugby | Fairfield Prep | Away [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Thu., 4/9 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | 2:00/5:00 | ED 1:45 |
| Fri., 4/10 | V Boys Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | 4:00 p.m. | 2:30pm/6:00pm | |
| Fri., 4/10 | V Softball | Nonnewaug | Away - Nonnewaug High School Field [Directions] | 4:00 p.m. | 2:00pm/5:00pm | |
| Sat., 4/11 | V Boys Volleyball | Southington | Away - Southington High School [Directions] | 6:00 p.m. | 3:00pm | |
| Sat., 4/11 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 11:30 a.m. | 10:00/12:30 | Shuttle with JV |
| Sat., 4/11 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 10:00 a.m. | 8:45am | Shuttle with varsity |
| Sat., 4/11 | V Girls Outdoor Track | Daniel Hand Freshmen Invitational | Away | Cancelled | 6:30am | |
| Mon., 4/13 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 12:00 p.m. | 10:30/1:30 | |
| Mon., 4/13 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 12:00 p.m. | 10:30/1:30 | |
| Mon., 4/13 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | 2:00 p.m. | 2:30pm/5:00pm | |
| Mon., 4/13 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 2:00 p.m. | 2:30pm/5:00pm | Share bus with varsity |
| Tue., 4/14 | V Baseball | Masuk | Away - John Giampaolo Field @ Masuk [Directions] | 1:00 p.m. | 11:15/2:30 | |
| Tue., 4/14 | V Boys Lacrosse | St. John The Baptist (NY) | Away | 4:00 p.m. | 12:00 | |
| Tue., 4/14 | V Boys Tennis | Westhill | Away [Directions] | 2:30 p.m. | 1:45/3:30 | |
| Wed., 4/15 | FR Baseball | Stamford | Away [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Wed., 4/15 | FR Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 4/15 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | 2:30/6:00 | |
| Wed., 4/15 | V Softball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 4/16 | V Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | 2:30/5:00 | |
| Thu., 4/16 | JV Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | 4:00/7:00 | |
| Fri., 4/17 | FR Baseball | St. Joseph | Away - St. Joseph High School [Directions] | 1:00 p.m. | 11:30/2:00 | |
| Fri., 4/17 | V Girls Outdoor Track | New York Relays | Away | Cancelled | 1:00/8:00 | |
| Fri., 4/17 | JV Softball | St. Joseph | Away - St. Joseph High School [Directions] | Cancelled | 12:30/5:00 | |
| Sat., 4/18 | FR Boys Lacrosse | St. Anthonys (NY) | Away | 11:00 a.m. | 8:30am/12:00 | |
| Sat., 4/18 | V Girls Outdoor Track | New York Relays | Away | 9:00 a.m. | 6:00am | |
| Mon., 4/20 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 4/20 | JV Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | 4:00/6:30 | |
| Tue., 4/21 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Tue., 4/21 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Tue., 4/21 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | 2:00/5:00 | ED 1:45 |
| Tue., 4/21 | V Girls Outdoor Track | Norwalk, Stamford | Away - Staples H.S. [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 4/21 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 4/21 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:45pm/5:00pm | |
| Wed., 4/22 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | 2:30/5:00 | |
| Wed., 4/22 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30/6:00 | |
| Wed., 4/22 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | Yes | Ride with varsity |
| Wed., 4/22 | FR Girls Lacrosse | Trumbull | Away - Indian Ledge Turf Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 4/23 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Thu., 4/23 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Thu., 4/23 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 4/23 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | p/u 5:00 @ Dwight Elem. | Ride with varsity to meet, separate buses for return |
| Thu., 4/23 | V Boys Volleyball | Newington | Away - Richard Rogalski Gymnasium @ Newington High School [Directions] | 5:30 p.m. | Yes | Ride with JV |
| Thu., 4/23 | JV Boys Volleyball | Newington | Away - Richard Rogalski Gymnasium @ Newington High School [Directions] | 4:30 p.m. | 2:30/6:00 | |
| Thu., 4/23 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | 2:30/5:00 | |
| Thu., 4/23 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 6:00 p.m. | 4:15/7:00 | |
| Thu., 4/23 | JV Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:30 p.m. | 3:00 | Shuttle with varsity |
| Thu., 4/23 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Thu., 4/23 | V Girls Water Polo | Greenwich | Away [Directions] | 3:00 p.m. | 1:30pm | ED 1:20 |
| Fri., 4/24 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Fri., 4/24 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away | 4:00 p.m. | 1:45 | ED 1:15 |
| Fri., 4/24 | V Girls Water Polo | Hopkins School | Away | 4:30 p.m. | 2:30/5:30 | |
| Sat., 4/25 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 12:00 p.m. | 10:00 | shuttle with JV |
| Sat., 4/25 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 2:00 p.m. | 12:30/3:00 | shuttle with varsity |
| Sat., 4/25 | V Boys Outdoor Track | O'Grady Relays @ Danbury HS | Away | 9:00 a.m. | 7:00am | |
| Sat., 4/25 | V Boys Rugby | Pegasi (Fairfield Town Team) | Away [Directions] | 6:30 p.m. | 5:00pm/8:00pm 2 buses | |
| Sat., 4/25 | JV Girls Lacrosse | Conard | Away - Conard HS South Field [Directions] | 12:00 p.m. | 10:00/2:30 | |
| Mon., 4/27 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | 1:45/4:30 | ED 1:30 |
| Mon., 4/27 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Mon., 4/27 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 4/27 | V Girls Outdoor Track | Ridgefield, Fairfield Warde | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:00/6:00 | ED 1:30 |
| Mon., 4/27 | V Softball | Harding | Away - Beardsley Park - Softball [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Mon., 4/27 | V Girls Tennis | Stamford | Away [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 4/28 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | 2:10/4:30 | ED 2:00 |
| Tue., 4/28 | V Boys Outdoor Track | Fairfield Warde, Ridgefield | Away [Directions] | 4:00 p.m. | 2:15/5:00 | ED 1:45 |
| Tue., 4/28 | JV Girls Golf | Greenwich | Away [Directions] | 3:15 p.m. | 2:15 | |
| Tue., 4/28 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | 5:30/8:00 | |
| Wed., 4/29 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 5:00 p.m. | 3:15/6:00 | |
| Wed., 4/29 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 4/29 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | 2:30/6:00 | |
| Wed., 4/29 | V Co-ed Sailing | Greenwich Academy, FLHS | Away | 3:00 p.m. | 2:15/5:45 | Indian harbor Yacht Club |
| Wed., 4/29 | JV Girls Golf | Fairfield Ludlowe | Away [Directions] | 3:30 p.m. | 2:15 | South Pine Creek |
| Wed., 4/29 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Wed., 4/29 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | 2:30/5:00 | |
| Wed., 4/29 | V Girls Water Polo | Hotchkiss | Away | 4:00 p.m. | 1:30 | ED 1:20 |
| Thu., 4/30 | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Thu., 4/30 | JV Boys Golf | Darien | Away - Woodway CC [Directions] | 3:00 p.m. | 2:00/5:00 | ED 1:50 |
| Thu., 4/30 | V Boys Lacrosse | Fox Lane (NY) | Away | 7:15 p.m. | 5:00/8:15 | |
| Thu., 4/30 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 4/30 | V Girls Water Polo | Choate Rosemary Hall | Away | 4:00 p.m. | 2:00pm | ED 1:50 |
| Fri., 5/1 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Fri., 5/1 | JV Baseball | Ridgefield | Away - East Ridge Middle School - South [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Fri., 5/1 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 5/1 | FR Boys Lacrosse | Don Bosco (NJ) | Away | 4:00 p.m. | 2:00 | 492 Franklin Turnpike, Ramsey NJ |
| Fri., 5/1 | V Boys Outdoor Track | Middletown Invitational | Away | 3:30 p.m. | 1:00pm | ED 12:30 |
| Sat., 5/2 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:30 p.m. | 3:00/5:00 | shuttle with JV |
| Sat., 5/2 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 2:30 p.m. | 1:00/3:30 | |
| Sat., 5/2 | FR Boys Lacrosse | Don Bosco Tournament | Away | 1:00 p.m. | 10:30am | |
| Sat., 5/2 | V Boys Outdoor Track | Middletown Invitational | Away | 1:00 p.m. | 10:30 | |
| Sat., 5/2 | V Girls Outdoor Track | Middletown Invitational | Away | TBA | 10:30 | |
| Sun., 5/3 | V Co-ed Sailing | US Coast Guard Academy | Away | TBA | Yes | |
| Mon., 5/4 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 6:00 p.m. | 4:30/7:30 | |
| Mon., 5/4 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Mon., 5/4 | V Boys Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | 2:10/6:00 | ED 1:55 |
| Mon., 5/4 | FR Girls Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 5/4 | V Girls Tennis | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 5/4 | V Girls Water Polo | Suffield Academy | Away | 4:00 p.m. | 1:30 | |
| Tue., 5/5 | V Boys Golf | Westhill | Away - E. Gaynor Brennan [Directions] | 3:00 p.m. | 2:00/4:30 | ED 1:45 |
| Tue., 5/5 | JV Boys Golf | Ridgefield, Byram Hills (NY) | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:00 p.m. | 2:00 | ED 1:50 |
| Tue., 5/5 | V Boys Outdoor Track | St. Joseph, Harding | Away - St. Joseph High School [Directions] | 3:45 p.m. | 1:45/6:00 | ED 1:15 |
| Tue., 5/5 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 5/5 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | 4:00/6:30 | |
| Tue., 5/5 | V Girls Tennis | Fairfield Warde | Away [Directions] | 4:00 p.m. | 2:45/5:00 | Share with JV, separate buses to return |
| Tue., 5/5 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods Middle School Courts [Directions] | 4:00 p.m. | 2:45/5:00 | Go with varsity, separate return |
| Wed., 5/6 | FR Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:00 p.m. | 2:30/5:00 | |
| Wed., 5/6 | FR Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Wed., 5/6 | V Softball | Trinity Catholic | Away - Trinity Catholic's Smith Field | 4:30 p.m. | 2:30/5:30 | |
| Wed., 5/6 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Thu., 5/7 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | 4:00/7:00 | |
| Thu., 5/7 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | 2:45/5:30 | |
| Thu., 5/7 | V Boys Outdoor Track | Louckes Games | Away | Cancelled | TBA | |
| Thu., 5/7 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | 1:45/5:00 | ED 1:30 |
| Thu., 5/7 | JV Girls Golf | Fairfield Warde | Away [Directions] | 3:30 p.m. | 2:15 | South Pine Creek |
| Thu., 5/7 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | 4:00/6:30 | shuttle with JV |
| Thu., 5/7 | JV Girls Lacrosse | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | 2:30 | Shuttle with Varsity |
| Thu., 5/7 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 5/7 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Fri., 5/8 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Fri., 5/8 | FR Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:00 p.m. | 3:00/5:00 | |
| Fri., 5/8 | FR Boys Lacrosse | Don Bosco Tournament | Away | Cancelled | 2:00pm | |
| Fri., 5/8 | V Boys Outdoor Track | Louckes Games | Away | TBA | 1:00 | Additional meet may be held on 5/9 |
| Fri., 5/8 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Fri., 5/8 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | 2:45/5:00 | |
| Sat., 5/9 | FR Boys Lacrosse | Don Bosco Tournament | Away | TBA | 10:30am | |
| Sat., 5/9 | V Boys Outdoor Track | Greater Hartford Invitational @ Simsbury | Away | 9:30 a.m. | 7:15am | |
| Sat., 5/9 | V Boys Rugby | Aspetuck Rugby Club | Away | 3:00 p.m. | 1:30/4:30 2 buses | 306 Umpawaug Rd Redding CT |
| Mon., 5/11 | V Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 4:00 p.m. | 2:00pm/5:30pm | ED 1:45 |
| Mon., 5/11 | JV Baseball | Danbury | Away - Danbury High School Junior Varsity Baseball Field [Directions] | 4:00 p.m. | 2:00/5:30 | ED 1:45 |
| Mon., 5/11 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Mon., 5/11 | V Boys Tennis | Bridgeport Central | Away - Central H.S. Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Mon., 5/11 | V Girls Outdoor Track | New Canaan, Fairfield Ludlowe | Away - NCHS Track Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 5/12 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:15 p.m. | 2:20/5:00 | |
| Tue., 5/12 | V Boys Tennis | Danbury | Away - Danbury High School Tennis Courts [Directions] | 4:00 p.m. | 2:10/5:00 | ED 2:00 |
| Tue., 5/12 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | 2:00/5:00 | ED 1:45 |
| Tue., 5/12 | FR Girls Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 6:00 p.m. | 4:00/7:00 | |
| Tue., 5/12 | V Girls Water Polo | Chelsea Piers | Away | TBA | 5:00/7:00 | |
| Wed., 5/13 | V Boys Golf | Fairfield Warde, Westhill | Away - Brooklawn Country Club [Directions] | 3:15 p.m. | 2:10/5:30 | ED 2:00 |
| Wed., 5/13 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:00 p.m. | 2:20/5:00 | |
| Wed., 5/13 | V Boys Tennis | Fairfield Prep | Away - Walsh Athletic Center Courts, Fairfield University [Directions] | 4:00 p.m. | 2:30/5:15 | |
| Wed., 5/13 | V Co-ed Sailing | GFA, DHS, Stamford | Away | 3:00 p.m. | 2:15/5:45 | Pequot Yacht Club |
| Wed., 5/13 | V Softball | Bassick | Away [Directions] | 4:00 p.m. | 2:30/5:30 | |
| Thu., 5/14 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Thu., 5/14 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | 2:00/5:00 | ED 1:45 |
| Thu., 5/14 | FR Girls Lacrosse | Greenwich Academy | Away | 5:00 p.m. | 3:00/6:00 | |
| Fri., 5/15 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Fri., 5/15 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | 2:45/5:30 | |
| Fri., 5/15 | V Boys Outdoor Track | Dream Invitational @ Danbury | Away | 7:00 p.m. | 5:00pm | |
| Fri., 5/15 | V Boys Rugby | Stamford Academy | Away | 4:00 p.m. | 2:30/5:30 2 buses | Lione Park, 325 Stillwater Ave, Stamford |
| Fri., 5/15 | V Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:45 p.m. | 2:30/5:00 | |
| Fri., 5/15 | JV Boys Tennis | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | p/u 5:00 | ride with varsity, separate bus to return to Staples |
| Fri., 5/15 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | 2:10/6:00 | ED 1:55 |
| Fri., 5/15 | FR Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | 3:00/5:30 | |
| Sat., 5/16 | V Co-ed Sailing | Silver Cup | Away | TBA | 7:00am | Indian Harbor |
| Mon., 5/18 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Mon., 5/18 | JV Baseball | Bridgeport Central | Away - Seaside Park Diamond 10 [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Mon., 5/18 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | 1:45/4:45 | ED 1:30 |
| Mon., 5/18 | JV Boys Golf | Wilton | Away [Directions] | 4:30 p.m. | 3:15/6:30 | |
| Mon., 5/18 | V Boys Tennis | Trumbull | Away - Tashua Knolls Tennis/Golf Course [Directions] | 6:00 p.m. | 4:30/7:00 | |
| Mon., 5/18 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Mon., 5/18 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | 2:30/5:00 | |
| Mon., 5/18 | V Girls Outdoor Track | Greenwich, Darien | Away - Cardinal Stadium [Directions] | 4:00 p.m. | 2:30/6:00 | |
| Tue., 5/19 | FR Baseball | Fairfield Country Day School | Away | 3:30 p.m. | 2:45/5:00 | |
| Tue., 5/19 | V Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | 1:45/5:00 | ED 1:30 |
| Tue., 5/19 | V Boys Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | 3:30/5:00 | |
| Tue., 5/19 | JV Boys Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 5/19 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 5/19 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Tue., 5/19 | V Boys Volleyball | Bridgeport Central | Away - Bassick High School [Directions] | 5:00 p.m. | 3:30pm/6:00pm | |
| Tue., 5/19 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | 2:10/5:00 | ED 1:55 |
| Tue., 5/19 | JV Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 5:30 p.m. | 4:00/6:30 | |
| Wed., 5/20 | V Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | 2:45pm/5:30pm | |
| Wed., 5/20 | JV Boys Golf | Brien McMahon | Away [Directions] | 3:00 p.m. | 2:20/5:00 | Oak Hill GC |
| Wed., 5/20 | V Boys Outdoor Track | Darien, Greenwich | Away - DHS Track [Directions] | 4:00 p.m. | 2:00/6:00 | ED 1:30 |
| Wed., 5/20 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | 2:00/4:30 | ED 1:45 |
| Thu., 5/21 | FR Boys Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | 2:30/5:30 | |
| Thu., 5/21 | V Boys Rugby | Greenwich | Away [Directions] | 4:45 p.m. | 2:30/6:00 2 buses | |
| Thu., 5/21 | FR Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 3:30 p.m. | 2:25/4:30 | |
| Thu., 5/21 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 5/22 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | 2:30/5:00 | |
| Fri., 5/22 | V Boys Lacrosse | FCIAC Quarterfinals vs Darien | Away | 4:00 p.m. | 2:30/5:00 | |
| Tue., 5/26 | V Boys Golf | Holahan Tournament | Away | TBA | 10:50/5:00 | ED 10:35 |
| Tue., 5/26 | V Boys Outdoor Track | FCIAC Championships @ Danbury | Away | 2:30 p.m. | 11:45 | ED 11:15 |
| Tue., 5/26 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | 1:45/5:00 | ED 1:30 |
| Tue., 5/26 | V Girls Outdoor Track | FCIAC Championship @ Danbury HS | Away | 2:30 p.m. | 11:45 | ED 11:15 |
| Wed., 5/27 | V Baseball | FCIAC Semi-finals @ Harbor Yard | Away | 7:00 p.m. | 4:30/8:30 | |
| Wed., 5/27 | V Boys Golf | Darien, Wilton | Away - CC of Darien [Directions] | 3:15 p.m. | 2:00/4:45 | ED 1:45 |
| Wed., 5/27 | V Boys Volleyball | FCIAC Semi-finals @ Fairfield Ludlowe HS | Away | 5:00 p.m. | 3:30/8:00 | |
| Wed., 5/27 | V Girls Tennis | FCIAC Finals @ Wilton HS | Away | 4:00 p.m. | 2:30/5:00 | |
| Wed., 5/27 | Unified Sports Track | Fairfield Ludlowe | Away [Directions] | 3:00 p.m. | 2:00 | 2 wheelchair buses |
| Thu., 5/28 | V Boys Tennis | FCIAC Finals Vs Greenwich @ Wilton HS | Away | 4:00 p.m. | 2:30/5:00 | |
| Fri., 5/29 | V Baseball | FCIAC Semi-finals @ Harbor Yard | Away | 4:00 p.m. | 1:30/5:30 | ED 1:00 |
| Sat., 5/30 | V Boys Tennis | State Tournament @ Hall HS | Away | TBA | 7:30am/6:00pm | |
| Sun., 5/31 | JV Boys Rugby | Aspetuck Rugby Club | Away | 2:30 p.m. | 1:45/5:00 | |
| Mon., 6/1 | V Boys Rugby | Playoffs vs. Ridgefield | Home - PJ Romano Field - Saugatuck Elem School [Directions] | 3:00 p.m. | 2:00/5:00 | ED 1:45 |
| Mon., 6/1 | V Boys Tennis | Class LL at Yale | Away | 10:30 a.m. | 8:30 | |
| Mon., 6/1 | V Boys Tennis | States at Yale | Away | 10:30 a.m. | 8:30 | |
| Mon., 6/1 | V Girls Tennis | Class L First Round vs. Trumbull | Home - Trumbull Racquet Club [Directions] | 2:00 p.m. | 1:15 | ED 1:00 |
| Tue., 6/2 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 2:30 p.m. | 11:45 | ED 11:15 |
| Tue., 6/2 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 2:30 p.m. | 11:45 | ED 11:15 |
| Tue., 6/2 | V Girls Tennis | CIAC Quarterfinal @ Trumbull Racquet Club | Home [Directions] | 3:00 p.m. | 2:00/4:00 | ED 1:45 |
| Wed., 6/3 | V Boys Golf | FCIAC Finals @ Fairchild Wheeler | Away | TBA | Yes | |
| Wed., 6/3 | V Boys Lacrosse | CIAC First Round vs. Fairfield Ludlowe | Away | 7:00 p.m. | 5:00/8:00 | |
| Wed., 6/3 | V Girls Golf | FCIAC Championship | Away | TBA | Yes | |
| Wed., 6/3 | V Softball | Class LL First Round vs. Trumbull | Away | 4:00 p.m. | 2:30/5:00 | |
| Wed., 6/3 | V Girls Tennis | Class L Semi Final vs. Glastonbury | Away | 3:00 p.m. | 12:30 | ED 12:15 |
| Thu., 6/4 | V Boys Outdoor Track | FR Invitational @ Danbury HS | Away | 4:00 p.m. | 2:00/5:30 | ED 1:30 |
| Thu., 6/4 | V Girls Lacrosse | Class L Quarterfinal vs. Darien | Away | 4:00 p.m. | 2:20/6:00 | |
| Fri., 6/5 | V Girls Tennis | Class L Final vs. FLHS/Darien winner @ Wilton HS | Away | 3:00 p.m. | 1:45 | ED 1:30 |
| Sat., 6/6 | V Boys Lacrosse | Class L Quarterfinals vs. Glastonbury | Away | 3:00 p.m. | 12:00/4:00 | |
| Mon., 6/8 | V Boys Golf | CIAC Div. I Championship | Away - Timberlin GC - Kensington [Directions] | 7:00 a.m. | 6:45am.4:00pm | |
| Mon., 6/8 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 10:45 | ED 10:15 |
| Tue., 6/9 | V Girls Golf | CIAC Girls Golf Championship | Away - Orange Hill CC - Orange [Directions] | 7:00 a.m. | 6:45am/1:00pm | |
| Wed., 6/10 | V Baseball | Class LL vs. Norwalk @ Muzzy Field | Away | 3:30 p.m. | 12:00/5:00 | ED |
| Sat., 6/13 | V Baseball | Class LL Finals vs. Amity at Palmer Field, Middletown CT | Away | 12:00 p.m. | 9:30am | |
| Tue., 6/16 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park | 11:30 a.m. | Yes | |
| Wed., 6/17 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | Yes | |