| Westhill 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 782 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | FR Baseball | Brien McMahon | Home - Rippowam Middle School [Directions] | TBA | ||
| TBA | FR Baseball | Darien | Home - Rippowam Middle School [Directions] | TBA | ||
| TBA | JV Football | Norwalk | Home - Westhill Football Field [Directions] | TBA | Cancelled | |
| TBA | V Boys Golf | Stamford, Trinity Catholic | Home - Woodway [Directions] | 1:00 p.m. | Trinity 161 Stamford 201 Westhill 177 | |
| TBA | FR Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 10:30 a.m. | ||
| TBA | JV Girls Basketball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | ||
| TBA | FR Field Hockey | Wilton | Home - Westhill Front Turf Field [Directions] | TBA | ||
| TBA | JV Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | TBA | ||
| TBA | FR Girls Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | TBA | ||
| TBA | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | TBA | ||
| TBA | JV Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Brien McMahon | Home - Roxbury Elementary School [Directions] | TBA | ||
| TBA | JV Girls Volleyball | Darien | Home - Westhill - Main Gymnasium [Directions] | TBA | Cancelled | |
| Wed., 8/28 | V Football | Newtown (Scrim.) | Away - Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | FR Football | Newtown (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Fri., 8/30 | V Girls Volleyball | Wilton (Scrim.) | Away - Wilton Field House [Directions] | 4:15 p.m. | ||
| Sat., 8/31 | V Football | @ Stratford vs. Stratford and Shleton | Away | 10:00 a.m. | ||
| Sat., 8/31 | FR Football | Darien (Scrim.) | Home - Westhill Football Field [Directions] | 10:00 a.m. | ||
| Sat., 8/31 | V Boys Soccer | Shelton (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Sat., 8/31 | JV Boys Soccer | Shelton (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Mon., 9/2 | V Football | Seymour (Scrim.) | Away - Seymour High Lower Field [Directions] | 9:00 a.m. | ||
| Tue., 9/3 | V Boys Soccer | Brookfield (Scrim.) | Away - BHS Stadium Field [Directions] | 4:30 p.m. | ||
| Tue., 9/3 | V Field Hockey | Lauralton Hall (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/3 | V Girls Soccer | Convent of Sacred Heart (Scrim.) | Away | 3:30 p.m. | ||
| Wed., 9/4 | V Football | Jonathan Law (Scrim.) | Home [Directions] | 3:30 p.m. | ||
| Wed., 9/4 | FR Football | Jonathan Law (Scrim.) | Home - Rippowam Middle School - Turf Field [Directions] | 3:30 p.m. | Early Release 1:46 | |
| Wed., 9/4 | V Field Hockey | King and Low-Heywood Thomas (Scrim.) | Away | 3:15 p.m. | ||
| Wed., 9/4 | V Girls Soccer | Greens Farms Academy (Scrim.) | Away | 3:00 p.m. | ||
| Wed., 9/4 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away | 3:15 p.m. | ||
| Sat., 9/7 | FR Field Hockey | Fairfield Ludlowe (Scrim.) | Away [Directions] | 11:00 a.m. | ||
| Sat., 9/7 | V Girls Soccer | Joel Barlow (Scrim.) | Away - Field J [Directions] | 4:00 p.m. | ||
| Sat., 9/7 | JV Girls Soccer | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 4:00 p.m. | ||
| Sat., 9/7 | V Girls Volleyball | Val Dickinson Jamboree @ Staples | Away | 9:00 a.m. | ||
| Mon., 9/9 | V Boys Soccer | St. Lukes (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Danbury, Staples, Brien McMahon, Darien | Away - Tarrywile Park [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Tue., 9/10 | V Girls Cross Country | Danbury, Staples, Brien McMahon, Darien | Away - Tarrywile Park [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Tue., 9/10 | V Field Hockey | Greenwich | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-5 | |
| Tue., 9/10 | JV Field Hockey | Greenwich | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 9/10 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | W 3-0 | |
| Tue., 9/10 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | W 2-0 | |
| Wed., 9/11 | FR Football | Norwalk | Home - Rippowam Middle School - Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/11 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | W 7-0 | |
| Thu., 9/12 | V Boys Soccer | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 4:00 p.m. | L 0-1 | Early Release @ 2:00 |
| Thu., 9/12 | V Competitive Cheerleading | Norwalk | Away [Directions] | 7:00 p.m. | ||
| Thu., 9/12 | V Girls Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | L 0-3 | |
| Thu., 9/12 | JV Girls Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/12 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/13 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | 3:00 p.m. | L 14-27 | |
| Fri., 9/13 | V Field Hockey | Stamford | Home - Westhill Front Turf Field [Directions] | 3:15 p.m. | W 4-2 | |
| Fri., 9/13 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 3:00 p.m. | W 1-0 | |
| Fri., 9/13 | JV Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 3:00 p.m. | ||
| Fri., 9/13 | V Girls Volleyball | Darien | Home - Westhill - Main Gymnasium [Directions] | 3:15 p.m. | L 0-3 | |
| Sat., 9/14 | Miscellaneous Events | uConn football | 7:00 p.m. | 2 buses | ||
| Mon., 9/16 | V Boys Soccer | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | T 2-2 | |
| Mon., 9/16 | JV Boys Soccer | Fairfield Warde | Home - Rippowam Middle School [Directions] | 4:15 p.m. | ||
| Mon., 9/16 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 5:30 p.m. | L 2-3 | |
| Mon., 9/16 | JV Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/17 | V Boys Cross Country | St. Joseph, Stamford, Norwalk | Away [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Tue., 9/17 | V Girls Cross Country | St. Joseph, Stamford, Norwalk | Away [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Tue., 9/17 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 0-1 | |
| Tue., 9/17 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/17 | V Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | L 5-0 | Early Release @ 1:46 |
| Tue., 9/17 | JV Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | Early Release at 1:46 | |
| Tue., 9/17 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | Early Release @ 1:30 | |
| Wed., 9/18 | V Boys Soccer | Darien | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | W 4-1 | |
| Wed., 9/18 | JV Boys Soccer | Darien | Home - Rippowam Middle School [Directions] | 4:15 p.m. | ||
| Wed., 9/18 | FR Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Girls Swimming and Diving | Danbury | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/18 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/19 | FR Football | Trinity Catholic | Away - Trinity Catholic Alumni Field | 4:00 p.m. | ||
| Thu., 9/19 | V Field Hockey | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 9/19 | JV Field Hockey | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 9/19 | FR Field Hockey | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | L 2-0 | Early Release @1:46 |
| Thu., 9/19 | JV Girls Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | Early Release @ 1:46 | |
| Fri., 9/20 | V Boys Soccer | Trinity Catholic | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | W 7-0 | |
| Fri., 9/20 | V Girls Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 9/20 | JV Girls Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/20 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | V Football | Trinity Catholic | Home - Westhill Football Field [Directions] | 2:00 p.m. | W 14-8 | |
| Sat., 9/21 | Band | Brien McMahon | Away [Directions] | 2:30 p.m. | ||
| Sat., 9/21 | V Competitive Cheerleading | Trinity Catholic | Home - Westhill Football Field [Directions] | 2:00 p.m. | ||
| Sat., 9/21 | V Field Hockey | Norwalk | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | W 2-0 | |
| Sat., 9/21 | JV Field Hockey | Norwalk | Home - Westhill Front Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 9/21 | FR Field Hockey | New Canaan | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 9/21 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m.. | W 1-0 | |
| Sat., 9/21 | JV Girls Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | JV Football | Trinity Catholic | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | V Boys Soccer | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | W 3-1 | |
| Mon., 9/23 | JV Boys Soccer | Trumbull | Home - Rippowam Middle School [Directions] | 4:15 p.m. | ||
| Mon., 9/23 | FR Boys Soccer | Trumbull | Away - JV Grass Soccer Field [Directions] | 4:00 p.m. | Early Release 2:00 | |
| Mon., 9/23 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 9/23 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| Mon., 9/23 | V Girls Volleyball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 9/23 | JV Girls Volleyball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | ||
| Mon., 9/23 | FR Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Fairfield Ludlowe, Greenwich, New Canaan, Trinity Catholic | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Fairfield Ludlowe, Greenwich, New Canaan, Trinity Catholic | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Soccer | Trinity Catholic | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | W 7-0 | |
| Wed., 9/25 | V Boys Soccer | Bassick | Away [Directions] | 4:00 p.m. | W 6-0 | Early Release @ 2:00 |
| Wed., 9/25 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | Early Release @ 1:46 | |
| Wed., 9/25 | V Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/25 | JV Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 9/26 | V Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | 6:00 p.m. | T 0-0 | |
| Thu., 9/26 | JV Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/26 | V Girls Soccer | Darien | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | L 3-0 | |
| Thu., 9/26 | JV Girls Soccer | Darien | Home - Rippowam Middle School [Directions] | 4:15 p.m. | ||
| Fri., 9/27 | FR Football | Staples | Away - Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/27 | V Girls Swimming and Diving | St. Joseph | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 9/27 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Fri., 9/27 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | FR Girls Volleyball | Fairfield Warde | Home [Directions] | 4:00 p.m. | ||
| Sat., 9/28 | V Boys Cross Country | Ocean State Invitational | Away | TBA | ||
| Sat., 9/28 | V Football | Staples | Home - Westhill Football Field [Directions] | 1:30 p.m. | L 14-63 | |
| Sat., 9/28 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 10:00 a.m. | L 1-2 | |
| Sat., 9/28 | JV Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 11:30 a.m. | ||
| Sat., 9/28 | FR Boys Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 9/28 | Band | Pequannock NJ | Away | 11:00 a.m. | ||
| Sat., 9/28 | V Competitive Cheerleading | Staples | Home - Westhill Football Field [Directions] | 1:30 p.m. | ||
| Sat., 9/28 | V Girls Cross Country | Ocean State Meet | Away | TBA | ||
| Mon., 9/30 | JV Football | Staples | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | V Girls Soccer | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 9/30 | JV Girls Soccer | Brien McMahon | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | V Girls Volleyball | Staples | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 9/30 | JV Girls Volleyball | Staples | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | ||
| Mon., 9/30 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Wilton, Ridgefield, Bridgeport Central | Away - Allen's Field #1 [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Tue., 10/1 | V Boys Soccer | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/1 | JV Boys Soccer | Bridgeport Central | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | FR Boys Soccer | Bridgeport Central | Away - Seaside B1 soccer field (Field is located along Atlantic St near Seaside Horsebarn). [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Wilton, Ridgefield, Bridgeport Central | Away - Allen's Field #1 [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Wed., 10/2 | V Field Hockey | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/2 | JV Field Hockey | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 10/2 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 7-1 | |
| Wed., 10/2 | JV Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 10/2 | V Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | L 0-3 | Early Release @ 1:46 |
| Wed., 10/2 | JV Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:30 p.m. | Early release at 1:46 | |
| Wed., 10/2 | FR Girls Volleyball | Danbury | Home [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Football | Brien McMahon | Home - Rippowam Middle School - Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 3-6 | |
| Thu., 10/3 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 10/3 | V Field Hockey | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 10/3 | JV Field Hockey | Trumbull | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 10/3 | FR Field Hockey | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | JV Girls Soccer | New Canaan | Away [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 10/4 | JV Girls Soccer | Trumbull | Away [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 10/4 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | Early Release @ 1:46 | |
| Fri., 10/4 | V Girls Volleyball | Bunnell | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | L 0-3 | |
| Fri., 10/4 | JV Girls Volleyball | Bunnell | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | V Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 2:00 p.m. | L 15-21 | |
| Sat., 10/5 | FR Boys Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 10/5 | Band | Newtown | Away [Directions] | 3:00 p.m. | ||
| Sat., 10/5 | V Competitive Cheerleading | Brien McMahon | Away [Directions] | 1:30 p.m. | ||
| Sat., 10/5 | FR Field Hockey | Danbury | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/7 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | Cancelled | |
| Mon., 10/7 | V Girls Volleyball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 10/7 | JV Girls Volleyball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Fairfield Warde, Bassick, Trumbull, Harding | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | JV Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Tue., 10/8 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:15 p.m. | L 0-1 | |
| Tue., 10/8 | V Girls Cross Country | Fairfield Warde, Bassick, Trumbull, Harding | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Soccer | New Canaan | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/8 | JV Girls Soccer | New Canaan | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | V Boys Soccer | Danbury | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/9 | JV Boys Soccer | Danbury | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | FR Boys Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 3:45 p.m. | Early Release 1:46 | |
| Wed., 10/9 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 0-5 | |
| Wed., 10/9 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 10/9 | V Girls Swimming and Diving | Staples | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 10/9 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/9 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | FR Football | Trumbull | Away - McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/10 | V Girls Soccer | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | W 4-0 | |
| Thu., 10/10 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | T 0-0 | |
| Fri., 10/11 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Field Hockey | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-2 | |
| Fri., 10/11 | JV Field Hockey | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 10/11 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Girls Volleyball | Wilton | Away - Wilton Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/11 | JV Girls Volleyball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | FR Girls Volleyball | Wilton | Home [Directions] | 4:00 p.m. | ||
| Sat., 10/12 | V Boys Cross Country | Wickham Park Meet | Away | TBA | ||
| Sat., 10/12 | V Football | Trumbull | Home - Westhill Football Field [Directions] | 1:30 p.m. | L 16-49 | |
| Sat., 10/12 | FR Boys Soccer | Stamford | Home - Westhill Front Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 10/12 | Band | Bridgeport Central | Away [Directions] | TBA | ||
| Sat., 10/12 | V Competitive Cheerleading | Trumbull | Home - Westhill Football Field [Directions] | 1:30 p.m. | ||
| Sat., 10/12 | V Girls Cross Country | Wickham Park Meet | Away | TBA | ||
| Sat., 10/12 | FR Field Hockey | Darien | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/14 | JV Football | Trumbull | Home - Westhill Football Field [Directions] | 11:00 a.m. | ||
| Mon., 10/14 | V Field Hockey | Bethel | Away - @ Bethel High School [Directions] | 10:00 a.m. | L 2-3 | |
| Mon., 10/14 | JV Field Hockey | Bethel | Away - @ Bethel High School [Directions] | 12:00 p.m. | ||
| Mon., 10/14 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/14 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | L 0-2 | |
| Tue., 10/15 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Tue., 10/15 | V Field Hockey | Ridgefield | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 10/15 | JV Field Hockey | Ridgefield | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/15 | JV Girls Volleyball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | ||
| Wed., 10/16 | SO Football | Stamford | Away - Stamford High School [Directions] | 4:30 p.m. | Cancelled | |
| Wed., 10/16 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Soccer | St. Joseph | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 4-1 | |
| Wed., 10/16 | JV Girls Soccer | St. Joseph | Home - Rippowam Middle School [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 10/16 | V Girls Swimming and Diving | Wilton | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 10/16 | FR Girls Volleyball | Darien | Away - DHS - South Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Boys Cross Country | FCIAC's @ Waveny Park | Away | 3:00 p.m. | ||
| Thu., 10/17 | FR Football | Bridgeport Central | Home - Rippowam Middle School - Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Boys Soccer | Wilton | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | T 1-1 | |
| Thu., 10/17 | JV Boys Soccer | Wilton | Home - Rippowam Middle School [Directions] | 4:15 p.m. | ||
| Thu., 10/17 | FR Boys Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Girls Cross Country | FCIAC's @ Waveny Park | Away | 3:30 p.m. | ||
| Fri., 10/18 | V Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 7:00 p.m. | W 38-14 | |
| Fri., 10/18 | V Competitive Cheerleading | Bridgeport Central | Away [Directions] | 7:00 p.m. | ||
| Fri., 10/18 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 7:30 p.m. | W 1-0(OT) | |
| Fri., 10/18 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | ||
| Fri., 10/18 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 1-5 | |
| Fri., 10/18 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Fri., 10/18 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | FR Girls Volleyball | Trumbull | Home [Directions] | 4:00 p.m. | ||
| Sat., 10/19 | JV Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/19 | FR Boys Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 10/19 | Band | Stamford | Away [Directions] | TBA | ||
| Sat., 10/19 | FR Field Hockey | Norwalk | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/21 | V Boys Soccer | New Canaan | Away - Dunning Stadium [Directions] | 7:00 p.m. | T 2-2 | |
| Mon., 10/21 | JV Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | FR Boys Soccer | New Canaan | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Field Hockey | Stamford | Away - Stamford High School [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/21 | JV Field Hockey | Stamford | Away - Stamford High School [Directions] | 4:30 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Staples | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/21 | JV Girls Soccer | Staples | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 6:30 p.m. | L 0-3 | |
| Mon., 10/21 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | FR Girls Volleyball | Fairfield Ludlowe | Home [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Soccer | Staples | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/22 | JV Boys Soccer | Staples | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | 5:00 p.m. | ||
| Wed., 10/23 | SO Football | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 10/23 | FR Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Field Hockey | Staples | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 10/23 | JV Field Hockey | Staples | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 10/23 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/23 | V Girls Volleyball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/23 | JV Girls Volleyball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Thu., 10/24 | JV Girls Soccer | Fairfield Warde | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | FR Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:30 p.m. | Early Release at 1:46 | |
| Fri., 10/25 | V Field Hockey | FCIAC Quarter-Finals vs. Darien | Away | 3:30 p.m. | ||
| Fri., 10/25 | V Girls Volleyball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | L 0-3 | |
| Fri., 10/25 | JV Girls Volleyball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | FR Girls Volleyball | Stamford | Away [Directions] | 4:00 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | State LL Meet @ Wickham Park | Away | 3:10 p.m. | ||
| Sat., 10/26 | V Football | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 2:00 p.m. | W 10-9 | |
| Sat., 10/26 | Band | Bridgeport Central | Away [Directions] | TBA | ||
| Sat., 10/26 | V Competitive Cheerleading | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 2:00 p.m. | ||
| Sat., 10/26 | V Girls Cross Country | State LL Meet @ Wickham Park | Away | 3:40 p.m. | ||
| Sat., 10/26 | V Girls Soccer | FCIAC Quarter-Finals @ Darien | Away | 2:00 p.m. | ||
| Sat., 10/26 | JV Girls Volleyball | Warde Jamboree | Away | 9:00 a.m. | ||
| Mon., 10/28 | JV Football | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/28 | V Girls Soccer | FCIAC Semi-Finals vs. Wilton @ Norwalk | Away | 5:00 p.m. | ||
| Mon., 10/28 | V Girls Swimming and Diving | FCIAC Trials @ Greenwich H.S. | Away | 4:00 p.m. | ||
| Tue., 10/29 | V Girls Swimming and Diving | FCIAC Diving Meet @ Westhill | Home [Directions] | 4:30 p.m. | ||
| Wed., 10/30 | V Boys Soccer | Norwalk (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | ||
| Wed., 10/30 | V Girls Swimming and Diving | FCIAC Finals @ Greenwich H.S. | Away | 4:00 p.m. | ||
| Thu., 10/31 | FR Football | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | Early Release @ 1:40 | |
| Thu., 10/31 | V Girls Volleyball | Stamford (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Fri., 11/1 | V Boys Cross Country | State Open Meet @ Wickham Park | Away | 2:00 p.m. | Cancelled | |
| Fri., 11/1 | V Girls Cross Country | State Open Meet @ Wickham Park | Away | 4:15 p.m. | ||
| Sat., 11/2 | V Football | Danbury | Home - Westhill Football Field [Directions] | 2:00 p.m. | W 23-22 | |
| Sat., 11/2 | V Boys Soccer | St. Joseph (Scrim.) | Away [Directions] | 11:00 a.m. | ||
| Sat., 11/2 | Band | Bunnell and Norwalk | Away | TBA | ||
| Sat., 11/2 | V Competitive Cheerleading | Danbury | Home - Westhill Football Field [Directions] | 1:30 p.m. | ||
| Mon., 11/4 | JV Football | Danbury | Home - Westhill Football Field [Directions] | 3:30 p.m. | ||
| Mon., 11/4 | V Field Hockey | State Tournament - Qualifying Round at Newtown | Away | 2:00 p.m. | ||
| Mon., 11/4 | V Girls Soccer | State Tournament - First Round vs. Trumbull | Home [Directions] | 2:00 p.m. | ||
| Mon., 11/4 | V Girls Volleyball | State Tournament - First Round @ Ridgefield | Away | 5:00 p.m. | ||
| Tue., 11/5 | V Boys Soccer | State Tournament - First Round @ Norwaich Free Academy | Away | 2:00 p.m. | ||
| Wed., 11/6 | SO Football | Greenwich | Away - Cardinal Stadium [Directions] | 3:30 p.m. | Cancelled | |
| Wed., 11/6 | V Field Hockey | Darien | Away [Directions] | 2:00 p.m. | ||
| Wed., 11/6 | V Girls Swimming and Diving | State LL Diving Championships @ Bulkelly H.S. | Away | 5:30 p.m. | ||
| Thu., 11/7 | FR Football | Greenwich | Home - Westhill Football Field [Directions] | 3:30 p.m. | ||
| Fri., 11/8 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | 7:00 p.m. | L 7-40 | |
| Fri., 11/8 | V Competitive Cheerleading | Greenwich | Away [Directions] | 7:00 p.m. | ||
| Sat., 11/9 | Band | Bridgeport Central | Away [Directions] | TBA | ||
| Sat., 11/9 | V Girls Swimming and Diving | LL State Meet at East Hartford H.S. | Away | 6:00 p.m. | ||
| Sun., 11/10 | Band | Allentown, PA | Away | TBA | ||
| Mon., 11/11 | JV Football | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Tue., 11/12 | V Girls Swimming and Diving | State LL Swim Championships @ SCSU | Away | 6:00 p.m. | ||
| Thu., 11/14 | SO Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | Cancelled | |
| Thu., 11/14 | FR Football | Harding | Home - Westhill Football Field [Directions] | 3:00 p.m. | Cancelled | |
| Fri., 11/15 | V Girls Swimming and Diving | State open Diving Championships @ Middletown | Away | 5:30 p.m. | ||
| Sat., 11/16 | V Football | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 1:30 p.m. | W 20-6 | |
| Sat., 11/16 | V Competitive Cheerleading | Harding | Away [Directions] | 1:30 p.m. | ||
| Sat., 11/16 | V Girls Swimming and Diving | State open Swim Championship @ Yale | Away | 12:00 p.m. | ||
| Mon., 11/18 | JV Football | Stamford | Home - Westhill Football Field [Directions] | 3:00 p.m. | ||
| Thu., 11/21 | FR Football | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 11/28 | V Football | Stamford | Home - Westhill Football Field [Directions] | 10:00 a.m. | W 40-0 | |
| Thu., 11/28 | V Competitive Cheerleading | Stamford | Home - Westhill Football Field [Directions] | 10:00 a.m. | ||
| Sat., 11/30 | V Girls Basketball | Multi-Team Scrimmage | Home - Westhill - Main Gymnasium [Directions] | 10:00 a.m. | ||
| Tue., 12/3 | V Girls Basketball | St. Lukes (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/5 | V Girls Basketball | Immaculate (Scrim.) | Away - Immaculate High School [Directions] | 4:00 p.m. | ||
| Sat., 12/7 | V Boys Basketball | Prince Tech Jamboree | Away | 10:00 p.m. | ||
| Sat., 12/7 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown High School Gymnasium [Directions] | 8:30 a.m. | ||
| Sat., 12/7 | V Girls Ice Hockey | Tournament Game - Opponent Not Known (Scrim.) | Home - Shelton Ice Rink [Directions] | 5:30 p.m. | ||
| Mon., 12/9 | V Boys Basketball | Kolbe Cathedral (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/11 | V Girls Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | W 46-22 | |
| Wed., 12/11 | JV Girls Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/11 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home [Directions] | 8:40 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | W 52-26 | |
| Fri., 12/13 | JV Girls Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 12/14 | V Wrestling | Weston, Masuk, Greenwich, Harding/Bassick/Bridgeport Central (Scrim.) | Home - Wrestling Room [Directions] | 9:00 a.m. | Cancelled | |
| Sat., 12/14 | V Girls Ice Hockey | Darien | Away - Darien Ice Darien Ice Rink [Directions] | 8:10 p.m. | Cancelled | |
| Mon., 12/16 | V Boys Basketball | Bethel (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/16 | V Boys Ice Hockey | King and Low-Heywood Thomas (Scrim.) | Away | 4:30 p.m. | ||
| Wed., 12/18 | V Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 7:00 p.m. | W 74-72 | |
| Wed., 12/18 | JV Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | V Boys Swimming and Diving | Darien | Away [Directions] | 3:00 p.m. | ||
| Wed., 12/18 | V Girls Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | W 50-41 | |
| Wed., 12/18 | JV Girls Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | FR Girls Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 12/19 | V Wrestling | Wilton | Away - Wilton Field House [Directions] | 6:00 p.m. | ||
| Fri., 12/20 | V Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 54-64 | |
| Fri., 12/20 | JV Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 12/20 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | W 47-41 | |
| Fri., 12/20 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | V Girls Ice Hockey | West Haven/SHA | Home - Terry Conners Ice Rink [Directions] | 8:30 p.m. | ||
| Sat., 12/21 | V Boys Ice Hockey | EnricoFermi | Away - Enfield Twin Rinks | 3:50 p.m. | L 5-4 | |
| Sat., 12/21 | V Boys Indoor Track | Developmental Meet @ Wilton | Away | 9:30 a.m. | ||
| Sat., 12/21 | V Wrestling | Shelton Invitational | Away | 10:00 a.m. | ||
| Sat., 12/21 | V Girls Indoor Track | Developmental Meet @ Wilton | Away | 9:30 a.m. | ||
| Thu., 12/26 | V Boys Ice Hockey | Stamford | Home - Terry Connors [Directions] | 6:30 p.m. | W 6-3 | |
| Thu., 12/26 | V Girls Basketball | Jonathan Law | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 55-31 | |
| Fri., 12/27 | V Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 7:00 p.m. | W 68-55 | |
| Fri., 12/27 | JV Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/27 | FR Boys Basketball | Bassick | Away - Bassick High School gymnasium [Directions] | 3:15p.m. | ||
| Fri., 12/27 | V Wrestling | Staples | Home - Westhill - New Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/28 | V Boys Basketball | King and Low-Heywood Thomas (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 12:00 p.m. | Cancelled | |
| Sat., 12/28 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | 5:40 p.m. | W 4-0 | |
| Sat., 12/28 | V Girls Basketball | Foran | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 51-19 | |
| Mon., 12/30 | V Boys Ice Hockey | New Milford | Home - Terry Connors [Directions] | 6:10 p.m. | L 3-7 | |
| Mon., 12/30 | V Wrestling | Trumbull McDougal Duals | Away - Westhill - New Gymnasium | 9:00 a.m. | ||
| Mon., 12/30 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Wonderland of Ice [Directions] | 9:30 a.m. | ||
| Sat., 1/4 | V Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 64-58 | |
| Sat., 1/4 | JV Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/4 | FR Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/4 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | 6:00 p.m. | L 0-6 | |
| Sat., 1/4 | V Boys Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | ||
| Sat., 1/4 | V Wrestling | Warde Invitational | Away | 10:00 a.m. | ||
| Sat., 1/4 | V Girls Ice Hockey | Greenwich | Home [Directions] | 8:40 p.m. | ||
| Sat., 1/4 | V Girls Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | ||
| Mon., 1/6 | V Boys Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 5:00 p.m. | W 51-42 | |
| Mon., 1/6 | JV Boys Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | Cancelled | |
| Mon., 1/6 | FR Boys Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 1/6 | V Girls Basketball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | L 42-71 | |
| Tue., 1/7 | V Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 58-39 | |
| Tue., 1/7 | JV Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/7 | FR Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/7 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 43-16 | |
| Tue., 1/7 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/7 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 1/8 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 6:00 p.m. | L 1-7 | |
| Wed., 1/8 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Wed., 1/8 | V Girls Gymnastics | Darien, New Canaan | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | Westhill 89.6 New Canaan 89.5 | |
| Wed., 1/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Norwalk Ice House [Directions] | 5:45 p.m. | ||
| Thu., 1/9 | V Wrestling | Greenwich | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 7:00 p.m. | W 66-62 | |
| Fri., 1/10 | JV Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | ||
| Fri., 1/10 | V Girls Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | L 39-47 | |
| Fri., 1/10 | JV Girls Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/11 | V Boys Ice Hockey | St. Joseph | Home - Terry Connors [Directions] | 5:00 p.m. | L 2-11 | |
| Sat., 1/11 | V Boys Indoor Track | Developmental Meet @ Wilton | Away | 9:30 a.m. | ||
| Sat., 1/11 | V Wrestling | Merrimack Valley, NH Tournament | Away | 9:15 a.m. | ||
| Sat., 1/11 | V Girls Ice Hockey | New Canaan | Away - Darien Rink [Directions] | 7:40 p.m. | ||
| Sat., 1/11 | V Girls Indoor Track | Developmental Meet @ Wilton | Away | 9:30 a.m. | ||
| Mon., 1/13 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 3:30 p.m. | ||
| Tue., 1/14 | V Boys Basketball | Harding | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 67-50 | |
| Tue., 1/14 | JV Boys Basketball | Harding | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | FR Boys Basketball | Harding | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | V Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | W 64-40 | |
| Tue., 1/14 | JV Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | FR Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 1/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Home [Directions] | 8:20 p.m. | ||
| Wed., 1/15 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 6:50 p.m. | L 2-6 | |
| Wed., 1/15 | V Girls Gymnastics | Staples, New Canaan | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | Staples - 125.75 Westhill - 104.8 | |
| Fri., 1/17 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | L 51-61 | |
| Fri., 1/17 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Staples | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/17 | V Wrestling | Warde Quad Meet | Away | 4:00 p.m. | ||
| Fri., 1/17 | V Girls Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | L 38-63 | |
| Fri., 1/17 | JV Girls Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Girls Gymnastics | Wilton, New Canaan | Away - Wilton High School Aux. Gym [Directions] | 5:00 p.m. | Wilton - 137.75 Westhill - 111.15 | |
| Sat., 1/18 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 5:50 p.m. | L 2-6 | |
| Sat., 1/18 | V Boys Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | ||
| Sat., 1/18 | V Girls Ice Hockey | Fairfield Warde | Away - Wonderland of Ice [Directions] | 1:00 p.m. | ||
| Sat., 1/18 | V Girls Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | ||
| Mon., 1/20 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 2:00 p.m. | L 3-4 | |
| Mon., 1/20 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven High School [Directions] | 10:00 a.m. | ||
| Thu., 1/23 | V Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 68-53 | |
| Thu., 1/23 | JV Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/23 | FR Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/23 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | W 61-52 | |
| Thu., 1/23 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/24 | V Boys Basketball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 63-43 | |
| Fri., 1/24 | JV Boys Basketball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/24 | FR Boys Basketball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | V Boys Swimming and Diving | Trumbull | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/24 | V Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 3:30 p.m. | W 47-21 | |
| Fri., 1/24 | JV Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 1/25 | V Boys Ice Hockey | Wilton | Home - Terry Connors [Directions] | 5:00 p.m. | L 2-8 | |
| Sat., 1/25 | V Boys Indoor Track | FCIAC Western Division Championships @ Staples | Away | 2:00 p.m. | ||
| Sat., 1/25 | V Boys Swimming and Diving | Glastonbury | Away - GHS Pool [Directions] | 3:00 p.m. | ||
| Sat., 1/25 | V Wrestling | Ridgefield Challenege | Away | TBA | ||
| Sat., 1/25 | V Competitive Cheerleading | Wolcott Invitational | Away | 10:00 a.m. | ||
| Sat., 1/25 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 1:30 p.m. | ||
| Sat., 1/25 | V Girls Indoor Track | FCIAC Western Division Championships @ Staples | Away | 2:00 p.m. | ||
| Mon., 1/27 | V Boys Swimming and Diving | Wilton | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Mon., 1/27 | V Competitive Cheerleading | FCIAC Partner Stunt Comp @ Ludlowe | Away | 5:00 p.m. | ||
| Mon., 1/27 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde, New Canaan | Away [Directions] | 6:30 p.m. | 98.85 | |
| Tue., 1/28 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 7:00 p.m. | W 68-56 | |
| Tue., 1/28 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Boys Ice Hockey | New Canaan | Home - Terry Connors [Directions] | 8:10 p.m. | L 1-6 | |
| Tue., 1/28 | V Girls Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | W 51-38 | |
| Tue., 1/28 | JV Girls Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/29 | V Boys Indoor Track | FCIAC Championships @ Floyd Little Athletic Center | Away | 4:30 p.m. | ||
| Wed., 1/29 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/29 | V Wrestling | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/29 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners Ice Rink [Directions] | 4:50 p.m. | ||
| Wed., 1/29 | V Girls Indoor Track | FCIAC Championships @ Floyd Little Athletic Center | Away | 4:30 p.m. | ||
| Thu., 1/30 | V Girls Gymnastics | Greenwich, New Canaan | Away - Greenwich YWCA [Directions] | 6:45 p.m. | Greenwich 125.00 Westhill 101.55 New Canaan 97.70 | |
| Thu., 1/30 | V Girls Ice Hockey | Masuk Coop | Away - Shelton High School [Directions] | 5:30 p.m. | ||
| Fri., 1/31 | V Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 78-75 ot | |
| Fri., 1/31 | JV Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | W 54-32 | |
| Fri., 1/31 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/1 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | L 2-3 (OT) | |
| Sat., 2/1 | V Wrestling | New Fairfield Duals | Away | 9:00 a.m. | ||
| Sat., 2/1 | V Wrestling | New Fairfield Duals | Away | 9:00 a.m. | ||
| Sat., 2/1 | V Competitive Cheerleading | FCIAC's @ Warde | Away | 8:00 a.m. | ||
| Tue., 2/4 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | W 70-63 | |
| Tue., 2/4 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Girls Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | W 37-35 | |
| Tue., 2/4 | JV Girls Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | FR Girls Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 2/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 8:20 p.m. | ||
| Thu., 2/6 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:45 p.m. | ||
| Thu., 2/6 | V Wrestling | New Canaan | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/6 | V Girls Ice Hockey | New Canaan | Home [Directions] | 8:40 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 65-51 | |
| Fri., 2/7 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Wrestling | Stamford | Away [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 5:45 p.m. | W 59-30 | |
| Fri., 2/7 | JV Girls Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Girls Gymnastics | New Milford | Away [Directions] | 5:00 p.m. | New Milford, 118.5 New Canaan, 95.750 Westhill, 94.950 | |
| Sat., 2/8 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 2-1 | |
| Sat., 2/8 | V Boys Indoor Track | State LL Meet @ the Floyd Little Athletic Complex | Away | 10:00 a.m. | ||
| Sat., 2/8 | V Wrestling | Stamford, Brien McMahon, Fairfield Ludlowe | Away - Stamford High School [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 2/8 | V Competitive Cheerleading | Nonnewaug H.s. Comp. | Away | 11:00 a.m. | ||
| Sat., 2/8 | V Girls Indoor Track | State LL Meet @ the Floyd Little Athletic Complex | Away | 10:00 a.m. | ||
| Mon., 2/10 | V Wrestling | Bridgeport Central | Home - Westhill - New Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 2/10 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 8:30 p.m. | ||
| Tue., 2/11 | V Girls Gymnastics | Trumbull, New Canaan | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | Trumbull - 129.75 Westhill - 105.6 New Canaan -95.40 | |
| Wed., 2/12 | V Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 62-49 | |
| Wed., 2/12 | JV Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/12 | FR Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/12 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 6:00 p.m. | W 2-1 | |
| Wed., 2/12 | V Girls Basketball | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | W 42-33 | |
| Wed., 2/12 | JV Girls Basketball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 2/12 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Terry Conners Ice Rink [Directions] | 3:40 p.m. | ||
| Fri., 2/14 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 2/14 | FR Girls Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 2/15 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 12:00 p.m. | L 40-51 | |
| Sat., 2/15 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 10:15 a.m. | ||
| Sat., 2/15 | V Wrestling | FCIAC's | Away | 9:00 a.m. | ||
| Sat., 2/15 | V Wrestling | FCIAC's | Away | TBA | ||
| Sat., 2/15 | V Girls Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 34-54 | |
| Sat., 2/15 | JV Girls Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 2/15 | V Girls Gymnastics | FCIAC Championships | Home - Westhill - Main Gymnasium [Directions] | 10:30 a.m. | 102.90 | |
| Sat., 2/15 | V Girls Ice Hockey | Fairfield Warde | Home - Terry Conners Ice Rink [Directions] | 3:10 p.m. | ||
| Mon., 2/17 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 3:30 p.m. | L 0-5 | |
| Mon., 2/17 | V Boys Indoor Track | State Open Meet @ the Floyd Little Athletic Complex | Away | 12:00 p.m. | ||
| Mon., 2/17 | V Girls Indoor Track | State Open Meet @ the Floyd Little Athletic Complex | Away | 12:00 p.m. | ||
| Tue., 2/18 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 2:20 p.m. | ||
| Wed., 2/19 | V Boys Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 75-37 | |
| Wed., 2/19 | JV Boys Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | FR Boys Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/19 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | 4:00 p.m. | L 2-8 | |
| Wed., 2/19 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 7:00 p.m. | W 46-34 | |
| Wed., 2/19 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/21 | V Boys Ice Hockey | Stamford | Home - Terry Connors [Directions] | 12:00 p.m. | W 4-3 | |
| Fri., 2/21 | V Boys Swimming and Diving | Danbury | Home - Westhill High School [Directions] | 3:30 p.m. | ||
| Fri., 2/21 | V Wrestling | State LL Meet | Away | 4:00 p.m. | ||
| Sat., 2/22 | V Wrestling | State LL Meet | Away | 9:00 a.m. | ||
| Sat., 2/22 | V Girls Basketball | FCIAC Quarter-Finals vs. Grrenwich | Home [Directions] | 12:00 p.m. | ||
| Sat., 2/22 | V Girls Gymnastics | Fairfield | Away | 4:00 p.m. | ||
| Sun., 2/23 | V Boys Ice Hockey | Norwalk | Home - Terry Connors [Directions] | 7:20 p.m. | W 8-2 | |
| Mon., 2/24 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | W 57-54 | |
| Mon., 2/24 | JV Boys Basketball | Darien | Away [Directions] | 5:15 p.m. | ||
| Mon., 2/24 | FR Boys Basketball | Darien | Away [Directions] | 4:00 p.m. | ||
| Tue., 2/25 | V Boys Swimming and Diving | FCIAC Trials @ Greenwich | Away | 4:30 p.m. | ||
| Wed., 2/26 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | W 67-63 | |
| Wed., 2/26 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Wed., 2/26 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Wed., 2/26 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | W 4-3 | |
| Wed., 2/26 | V Boys Swimming and Diving | FCIAC Diving | Home [Directions] | 4:30 p.m. | ||
| Wed., 2/26 | V Girls Ice Hockey | Greenwich | Away [Directions] | 6:45 p.m. | ||
| Thu., 2/27 | V Boys Swimming and Diving | FCIAC Championship @ Greenwich | Away | 6:00 p.m. | ||
| Fri., 2/28 | V Wrestling | State Open Meet @ The Floyd Little Athletic Complex | Away | 4:00 p.m. | ||
| Sat., 3/1 | V Boys Basketball | FCIAC Quarter-Finals vs. Stamford @ Ludlowe | Away | 5:00 p.m. | ||
| Sat., 3/1 | V Competitive Cheerleading | BEST Comp in Danbury | Away | TBA | ||
| Sat., 3/1 | V Girls Indoor Track | New England Championships in Boston | Away | 9:00 a.m. | ||
| Mon., 3/3 | V Girls Basketball | State Tournament - First Round vs. New Milford | Home [Directions] | 6:00 p.m. | ||
| Thu., 3/6 | V Girls Basketball | State Championship Second Round Game vs. Stamford | Home [Directions] | 6:00 p.m. | ||
| Fri., 3/7 | V Wrestling | New England Championships | Away | TBA | ||
| Sat., 3/8 | V Competitive Cheerleading | STATES @ Hillhouse | Away | 3:00 p.m. | ||
| Mon., 3/10 | V Boys Ice Hockey | New Fairfield | Away [Directions] | 7:40 p.m. | ||
| Mon., 3/10 | V Girls Basketball | State Quarter-Finals vs. Danbury @ Danbury | Away | 7:00 p.m. | ||
| Tue., 3/11 | V Boys Basketball | State LL Championship vs. Harding - First Round | Home [Directions] | 6:00 p.m. | ||
| Wed., 3/12 | V Boys Swimming and Diving | State LL Diving Meet @ Hampden H.S. | Away | 4:30 p.m. | ||
| Fri., 3/14 | V Girls Basketball | State LL Semi-Finals vs. South Windsor @ Kennedy H.S. | Away | 7:00 p.m. | ||
| Wed., 3/19 | V Boys Swimming and Diving | LL State Tournament @ Wesleyan University | Away | 3:00 p.m. | ||
| Thu., 3/27 | V Baseball | St. Raymond's | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 3/28 | V Boys Lacrosse | Hopkins School (Scrim.) | Home - Westhill Front Field [Directions] | 4:00 p.m. | ||
| Sat., 3/29 | V Baseball | Darien (Scrim.) | Away - DHS Baseball Varsity Field [Directions] | 10:00 a.m. | ||
| A request to make the following change(s) to the above event has been submitted by one of the schools involved, but has not yet been accepted by the other -- Change date to 03/29/15 | ||||||
| Sat., 3/29 | V Boys Lacrosse | Guilford Lax Bash | Away | 3:00 p.m. | ||
| Sat., 3/29 | V Softball | Darien Round Robin | Away | 10:00 a.m. | ||
| Sun., 3/30 | V Softball | Multi - Team Scrimmage @ Cummings | Away | 10:00 a.m. | ||
| Wed., 4/2 | V Baseball | Greenwich (Scrim.) | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/2 | V Boys Tennis | Amity (Scrim.) | Away - Amity High School [Directions] | 3:45 p.m. | ||
| Thu., 4/3 | V Boys Tennis | King and Low-Heywood Thomas (Scrim.) | Away | 4:00 p.m. | ||
| Thu., 4/3 | V Softball | New Canaan (Scrim.) | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Fri., 4/4 | V Softball | Torrington (Scrim.) | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/5 | V Baseball | New Canaan (Scrim.) | Away - Mead Park [Directions] | 12:00 a.m. | ||
| Sat., 4/5 | V Boys Lacrosse | Stamford Jamboree | Away | 8:30 a.m. | ||
| Mon., 4/7 | V Baseball | Greenwich (Scrim.) | Away - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/7 | FR Baseball | New Canaan (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Boys Tennis | Ridgefield | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 4/9 | V Softball | Masuk | Home - Westhill Varsity Softball Field [Directions] | 4:15 p.m. | L 0-2 | |
| Wed., 4/9 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/10 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | Greenwich 160 Westhill 198 | |
| Thu., 4/10 | V Boys Lacrosse | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 5:15 p.m. | L 5-7 | |
| Thu., 4/10 | JV Boys Lacrosse | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Thu., 4/10 | V Boys Outdoor Track | Danbury | Home [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Thu., 4/10 | V Girls Outdoor Track | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | Early Release at 1:46 | |
| Thu., 4/10 | V Girls Tennis | Staples | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 4/11 | V Baseball | St. Joseph | Away - St. Joseph High School [Directions] | 4:15 p.m. | W 7-6 | |
| Fri., 4/11 | JV Baseball | St. Joseph | Away - Madison Middle School, Trumbull [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | FR Baseball | St. Joseph | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | V Softball | St. Joseph | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | L 3-15 | |
| Fri., 4/11 | JV Softball | St. Joseph | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Sat., 4/12 | V Baseball | Weston | Home - Westhill Baseball Field [Directions] | 11:00 a.m. | L 3-4 | |
| Sat., 4/12 | JV Baseball | Weston | Home - Westhill Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 4/12 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 2:00 p.m. | L 1-23 | |
| Sat., 4/12 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 2:00 p.m. | ||
| Sat., 4/12 | V Girls Lacrosse | Ridgefield | Home - Westhill Front Turf Field [Directions] | 3:00 p.m. | L 7-21 | |
| Sat., 4/12 | JV Girls Lacrosse | Ridgefield | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 4/14 | V Baseball | Ridgefield | Home - Westhill Baseball Field [Directions] | 11:00 a.m. | W 5-4 | |
| Mon., 4/14 | JV Baseball | Ridgefield | Home - Westhill Baseball Field [Directions] | 2:00 p.m. | ||
| Mon., 4/14 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 11:00 a.m. | ||
| Mon., 4/14 | V Boys Lacrosse | King and Low-Heywood Thomas | Away | 3:30 p.m. | W 6-5 | |
| Mon., 4/14 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 11:00 a.m. | W 4-3 | |
| Mon., 4/14 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 11:00 a.m. | W 7-6 | |
| Mon., 4/14 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 11:00 a.m. | ||
| Mon., 4/14 | V Girls Tennis | Fairfield Warde | Home - Westhill Tennis Courts [Directions] | 11:00 a.m. | L 7-0 | |
| Tue., 4/15 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 4/15 | V Girls Lacrosse | Staples | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 18-1 | |
| Tue., 4/15 | JV Girls Lacrosse | Staples | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 4/16 | V Baseball | Wilton | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 9-0 | |
| Wed., 4/16 | JV Baseball | Wilton | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Wed., 4/16 | FR Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/16 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | 1:00 p.m. | W 16-1(5) | |
| Thu., 4/17 | V Baseball | New Canaan | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | L 5-9 | |
| Thu., 4/17 | JV Baseball | New Canaan | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Thu., 4/17 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Thu., 4/17 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | L 14-3 | |
| Thu., 4/17 | JV Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 4/17 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | W 7-1 | |
| Sat., 4/19 | V Baseball | South Windsor | Away - South Windsor High School [Directions] | 1:00 p.m. | L 2-5 | |
| Sat., 4/19 | JV Baseball | South Windsor | Away - South Windsor High School [Directions] | 1:00 p.m. | Cancelled | |
| Sat., 4/19 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 10:00 a.m. | L 2-15 | |
| Sat., 4/19 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 12:00 p.m. | ||
| Mon., 4/21 | V Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 4:00 p.m. | L 1-4 | Early Release 1:46 |
| Mon., 4/21 | JV Baseball | Danbury | Away - Danbury High School Junior Varsity Baseball Field [Directions] | 4:00 p.m. | Early Release 1:46 | |
| Mon., 4/21 | FR Baseball | Danbury | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Boys Golf | New Canaan | Home - Hubbard Brennan Golf Course [Directions] | 3:00 p.m. | New Canaan 158 Westhill 192 | |
| Mon., 4/21 | V Boys Tennis | Danbury | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 4/21 | V Softball | Danbury | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | L 4-5 | |
| Mon., 4/21 | JV Softball | Danbury | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Girls Tennis | Danbury | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/22 | FR Baseball | Stamford | Away [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Golf | Ridgefield | Home - Hubbard Brennan Golf Course [Directions] | 3:30 p.m. | Ridgefield 150 Westhill 186 | |
| Tue., 4/22 | V Boys Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | L 4-14 | |
| Tue., 4/22 | JV Boys Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Outdoor Track | Greenwich, Harding | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 6-0 | |
| Tue., 4/22 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 6:00 p.m. | L 6-18 | |
| Tue., 4/22 | JV Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/22 | V Girls Outdoor Track | Harding, Greenwich | Home [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Baseball | Harding | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 4/23 | JV Baseball | Harding | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Boys Golf | Darien | Away - TBA [Directions] | 3:15 p.m. | Darien 162 Westhill 196 | |
| Wed., 4/23 | V Softball | Harding | Away - Beardsley Park - Softball [Directions] | 4:00 p.m. | W 13-0 | |
| Wed., 4/23 | JV Softball | Harding | Away - Beardsley Park-Softball-JV [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | FR Baseball | Greenwich | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | V Boys Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | Staples 162 Westhill 180 | |
| Thu., 4/24 | V Boys Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 5:15 p.m. | L 9-3 | |
| Thu., 4/24 | JV Boys Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Thu., 4/24 | V Boys Tennis | St. Joseph | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 4/24 | V Girls Tennis | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | W 5-2 | |
| Fri., 4/25 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 4/25 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | V Boys Tennis | Norwalk | Away - Norwalk High Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/25 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 11-6 | |
| Fri., 4/25 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Fri., 4/25 | V Softball | Greenwich | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 4/25 | JV Softball | Greenwich | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | V Girls Tennis | Norwalk | Home - Westhill Tennis Courts [Directions] | 4:00 a.m. | W 7-0 | |
| Sat., 4/26 | V Boys Lacrosse | Danbury | Home - Westhill Front Field [Directions] | 2:00 p.m. | L 7-6 | |
| Sat., 4/26 | JV Boys Lacrosse | Danbury | Home - Westhill Front Field [Directions] | 12:00 p.m. | ||
| Mon., 4/28 | V Baseball | Fairfield Warde | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | L 5-9 | |
| Mon., 4/28 | JV Baseball | Fairfield Warde | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Boys Golf | St. Joseph | Away [Directions] | 3:15 p.m. | Trumbull 160 St. Joseph 180 Westhill 187 | |
| Mon., 4/28 | V Boys Tennis | Greenwich | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 4/28 | V Girls Lacrosse | Bristol Eastern | Away - Bristol Eastern High School [Directions] | 6:00 p.m. | W 12-3 | Early Release 1:30 |
| Mon., 4/28 | JV Girls Lacrosse | Bristol Eastern | Away - Bristol Eastern High School [Directions] | 4:30 p.m. | Early Release 1:30 | |
| Mon., 4/28 | V Girls Outdoor Track | New Canaan, Bridgeport Central | Away [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | W 5-1 | |
| Mon., 4/28 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/29 | V Boys Golf | Brien McMahon | Away - Oak Hills [Directions] | 3:30 p.m. | Westhill 179 McMahon 182 | |
| Tue., 4/29 | V Boys Outdoor Track | New Canaan, Bridgeport Central | Home [Directions] | 4:00 p.m. | ||
| Wed., 4/30 | V Boys Lacrosse | Brunswick School | Away | 5:30 p.m. | L 9-3 | |
| Thu., 5/1 | V Boys Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 5/2 | V Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | W 14-10 | |
| Fri., 5/2 | JV Baseball | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | FR Baseball | Norwalk | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:30 p.m. | L 11-12 | |
| Fri., 5/2 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 5:00 p.m. | ||
| Fri., 5/2 | V Softball | Norwalk | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | L 2-4 | |
| Fri., 5/2 | JV Softball | Norwalk | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Girls Tennis | Trumbull | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Sat., 5/3 | V Boys Lacrosse | St. Joseph | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | L 2-12 | |
| Sat., 5/3 | JV Boys Lacrosse | St. Joseph | Home - Westhill Front Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 5/3 | FR Boys Lacrosse | St. Joseph | Home - Westhill Front Turf Field [Directions] | 10:30 a.m. | Cancelled | |
| Sat., 5/3 | V Girls Lacrosse | Joel Barlow | Away - Field J [Directions] | 4:00 p.m. | L 5-18 | |
| Sat., 5/3 | JV Girls Lacrosse | Joel Barlow | Away - Field J [Directions] | 2:30 p.m. | ||
| Mon., 5/5 | V Baseball | Bridgeport Central | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/5 | JV Baseball | Bridgeport Central | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | FR Baseball | Stamford | Home - Belltown [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | Danbury 180 Westhill 189 | |
| Mon., 5/5 | V Boys Tennis | Darien | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/5 | V Girls Outdoor Track | Ridgefield, Fairfield Ludlowe | Away - Taft Field [Directions] | 3:45 p.m. | ||
| Mon., 5/5 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | 4:00 p.m. | W 13-0 | |
| Mon., 5/5 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/6 | V Baseball | Bassick | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 17-0 | |
| Tue., 5/6 | V Boys Golf | Fairfield Warde | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Warde 165 Westhill 187 | |
| Tue., 5/6 | V Boys Outdoor Track | Ridgefield, Fairfield Ludlowe | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Tennis | Wilton | Away - WHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 5/6 | V Girls Lacrosse | Danbury | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-16 | |
| Tue., 5/6 | JV Girls Lacrosse | Danbury | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/6 | V Softball | Bassick | Away - Went Field [Directions] | 4:00 p.m. | W 12-0 | |
| Tue., 5/6 | V Girls Tennis | Wilton | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 5/7 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 6:00 p.m. | L 1-4 | |
| Wed., 5/7 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | FR Baseball | Trumbull | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Boys Golf | Wilton | Home - Hubbard Brennan Golf Course [Directions] | 3:30 p.m. | Wilton 161 Westhill 178 | |
| Wed., 5/7 | V Girls Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 9-12 | |
| Wed., 5/7 | JV Girls Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 5/7 | V Softball | Trumbull | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 8-1 | |
| Wed., 5/7 | JV Softball | Trumbull | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Girls Tennis | Bridgeport Central | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/8 | V Boys Lacrosse | Ridgefield | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | L 1-17 | |
| Thu., 5/8 | JV Boys Lacrosse | Ridgefield | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Fri., 5/9 | JV Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 5/10 | V Boys Lacrosse | Trinity Catholic | Home - Westhill Front Turf Field [Directions] | 1:30 p.m. | W 15-4 | |
| Sat., 5/10 | JV Boys Lacrosse | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | 11:30 a.m. | ||
| Sat., 5/10 | V Girls Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 2:00 p.m. | L 2-18 | |
| Sat., 5/10 | JV Girls Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | Cancelled | |
| Mon., 5/12 | V Baseball | Stamford | Home - Cubeta [Directions] | 6:30 p.m. | W 3-2 | |
| Mon., 5/12 | JV Baseball | Stamford | Home - Westhill High School [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | FR Baseball | Stamford | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Ludlowe 160 Westhill 171 | |
| Mon., 5/12 | FR Boys Lacrosse | Stamford | Home - Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 5/12 | V Boys Tennis | Brien McMahon | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/12 | V Girls Outdoor Track | Staples, Trumbull | Home [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Softball | Stamford | Away - Cove Island Park [Directions] | 6:30 p.m. | L 3-4 | |
| Mon., 5/12 | JV Softball | Stamford | Home - Cove Island Beach Sotball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 5/13 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/13 | V Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | 5:30 p.m. | L 4-15 | |
| Tue., 5/13 | JV Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/13 | V Boys Outdoor Track | Trumbull, Staples | Away - McDougall Stadium [Directions] | 4:00 p.m. | Early Release at 1:46 | |
| Tue., 5/13 | V Boys Tennis | New Canaan | Away [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/13 | V Girls Lacrosse | Stamford | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-18 | |
| Tue., 5/13 | JV Girls Lacrosse | Stamford | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/13 | V Softball | Brien McMahon | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 9-1 | |
| Tue., 5/13 | V Girls Tennis | New Canaan | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 5/14 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 5/14 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | FR Baseball | Fairfield Ludlowe | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | V Boys Tennis | Trinity Catholic | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/14 | V Softball | Fairfield Ludlowe | Home - Westhill Varsity Softball Field [Directions] | 4:15 p.m. | W 6-5 | |
| Wed., 5/14 | JV Softball | Fairfield Ludlowe | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Thu., 5/15 | V Boys Lacrosse | Weston | Away - WHS Turf Field [Directions] | 4:00 p.m. | L 4-11 | Early Release at 1:46 |
| Thu., 5/15 | JV Boys Lacrosse | Weston | Away - WHS Stadium Field [Directions] | 5:30 p.m. | Early Release at 1:46 | |
| Thu., 5/15 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/15 | V Girls Tennis | Fairfield Ludlowe | Away - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-5 | |
| Fri., 5/16 | V Girls Outdoor Track | Stamford | Home [Directions] | 3:00 p.m. | Cancelled | |
| Sat., 5/17 | V Boys Lacrosse | Bethel | Home - Westhill Front Turf Field [Directions] | 1:30 p.m. | L 10-11 | |
| Sat., 5/17 | JV Boys Lacrosse | Bethel | Home - Westhill Front Turf Field [Directions] | 11:45 a.m. | Cancelled | |
| Sat., 5/17 | V Boys Outdoor Track | Stamford | Away - Stamford High School [Directions] | 11:30 a.m. | ||
| Sat., 5/17 | V Boys Outdoor Track | City Championship Field Events | Home [Directions] | 9:00 a.m. | ||
| Sat., 5/17 | V Girls Lacrosse | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 7-22 | |
| Sat., 5/17 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Sat., 5/17 | V Girls Outdoor Track | Stamford | Away - Stamford High School [Directions] | 11:30 a.m. | ||
| Sat., 5/17 | V Girls Outdoor Track | City Championship Field Events | Home [Directions] | 9:00 a.m. | ||
| Mon., 5/19 | V Baseball | Staples | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | L 2-9 | |
| Mon., 5/19 | JV Baseball | Staples | Home - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Boys Golf | Bassick, Bridgeport Central, Harding | Away - Fairchild-Wheeler [Directions] | 3:15 p.m. | Westhill 178 Harding 264 | |
| Mon., 5/19 | V Boys Tennis | Stamford | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/19 | V Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | L 5-20 | |
| Mon., 5/19 | FR Girls Lacrosse | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Girls Outdoor Track | Fairfield Warde, Brien McMahon | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Softball | Staples | Away - Wakeman Field C [Directions] | 4:00 p.m. | W 10-6 | |
| Mon., 5/19 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Girls Tennis | Stamford | Away [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 5/20 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Norwalk 171 Westhill 186 | |
| Tue., 5/20 | V Boys Lacrosse | Darien | Home - Westhill Front Turf Field [Directions] | 5:45 p.m. | L 2-19 | |
| Tue., 5/20 | JV Boys Lacrosse | Darien | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 5/20 | V Boys Outdoor Track | Brien McMahon, Fairfield Warde | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Tue., 5/20 | V Girls Lacrosse | Stamford | Away - Stamford High School [Directions] | 6:00 p.m. | L 1-13 [Detailed Results] | |
| Tue., 5/20 | JV Girls Lacrosse | Stamford | Away [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 5/20 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | 4:15 p.m. | W 5-2 | |
| Wed., 5/21 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | L 4-9 | |
| Wed., 5/21 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | FR Baseball | Darien | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Softball | Darien | Home - Westhill Varsity Softball Field [Directions] | 4:15 p.m. | L 0-6 | |
| Wed., 5/21 | JV Softball | Darien | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Thu., 5/22 | V Boys Lacrosse | Stamford | Away - Stamford High School [Directions] | 7:00 p.m. | L 2-8 | |
| Thu., 5/22 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:30 p.m. | ||
| Thu., 5/22 | V Boys Tennis | Wilton | Home - Old Greenwich Tennis Association [Directions] | 3:00 p.m. | ||
| Fri., 5/23 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 2:00 p.m. | L 1-4 | |
| Fri., 5/23 | JV Baseball | Trinity Catholic | Home - Westhill Baseball Field [Directions] | 2:00 p.m. | ||
| Fri., 5/23 | FR Baseball | Trinity Catholic | Home - Rippowam [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | V Softball | Trinity Catholic | Home - Westhill Varsity Softball Field [Directions] | 2:00 p.m. | W 3-1 | |
| Tue., 5/27 | V Boys Outdoor Track | FCIAC's @ Danbury H.S. | Away | 2:00 p.m. | ||
| Tue., 5/27 | V Boys Tennis | FCIAC Semi-Finals @ Ridgefield | Away | 4:00 p.m. | ||
| Tue., 5/27 | V Girls Outdoor Track | FCIAC's @ Danbury H.S. | Away | 2:00 p.m. | ||
| Tue., 5/27 | V Softball | FCIAC Quarter-Finals @ Greenwich | Away | 4:00 p.m. | ||
| Wed., 5/28 | V Softball | FCIAC Semi-Finals vs. Darien @ Sacred Heart University | Away | 3:00 p.m. | ||
| Thu., 5/29 | V Boys Golf | City Meet @ Woodway | Away | 1:00 p.m. | ||
| Thu., 5/29 | V Boys Outdoor Track | Freshmaqn Meet @ Danbury H.S. | Away | 4:00 p.m. | ||
| Fri., 5/30 | V Baseball | Trinity Catholic (Scrim.) | Home [Directions] | 3:30 p.m. | ||
| Mon., 6/2 | V Baseball | State Tournament @ Trumbull | Away | 3:30 p.m. | ||
| Mon., 6/2 | V Boys Tennis | State Tournament @ Yale | Away | 4:00 p.m. | ||
| Mon., 6/2 | V Softball | State Tournament vs. Conard | Home [Directions] | 4:00 p.m. | ||
| Tue., 6/3 | V Boys Golf | Hollohan @ CC of Darien | Away | 12:30 p.m. | ||
| Tue., 6/3 | V Boys Outdoor Track | State LL Meet @ Danbury H.S. | Away | 2:30 p.m. | ||
| Tue., 6/3 | V Boys Tennis | State Semi-Finals @ Yale | Away | 4:00 p.m. | ||
| Tue., 6/3 | V Girls Outdoor Track | State LL Meet @ Danbury H.S. | Away | 2:30 p.m. | ||
| Tue., 6/3 | V Softball | 2nd Round of the State Tournament vs. Greenwich | Away | 4:00 p.m. | ||
| Thu., 6/5 | V Boys Outdoor Track | State LL Meet @ Danbury H.S. | Away | 2:30 p.m. | ||
| Mon., 6/9 | V Boys Outdoor Track | State Open Meet @ Middletown | Away | TBA | ||
| Mon., 6/9 | V Girls Outdoor Track | State Open Meet @ Middletown | Away | TBA | ||