| Westhill 2016-17 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 686 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | ||
| TBA | FR Boys Lacrosse | Shelton | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | ||
| TBA | FR Boys Lacrosse | Shelton | Away - Shelton HS - Lower Field [Directions] | Cancelled | Cancelled | |
| TBA | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | Cancelled | Cancelled | |
| TBA | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Vet's Park - Norwalk [Directions] | 3:30 p.m. | Junior Varsity Game | |
| TBA | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | TBA | ||
| TBA | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | TBA | ||
| TBA | JV Girls Lacrosse | Jonathan Law | Home - Westhill Front Turf Field [Directions] | TBA | ||
| TBA | JV Softball | Darien | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Wilton | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Tue., 8/30 | V Girls Soccer | St. Lukes (Scrim.) | Away | 4:30 p.m. | ||
| Thu., 9/1 | V Football | Jonathan Law (Scrim.) | Away - Lawmen Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/1 | JV Football | Jonathan Law (Scrim.) | Away [Directions] | 5:00 p.m. | ||
| Fri., 9/2 | V Field Hockey | St. Joseph (Scrim.) | Home - Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 9/2 | JV Field Hockey | St. Joseph (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 9/3 | V Boys Soccer | Stamford (Scrim.) | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 9/5 | V Girls Soccer | Joel Barlow (Scrim.) | Away - Field J (competition field) [Directions] | 11:00 a.m. | ||
| Mon., 9/5 | V Girls Volleyball | Notre Dame-Fairfield (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 9:30 a.m. | ||
| Wed., 9/7 | V Boys Soccer | Fairfield Prep (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Wed., 9/7 | V Field Hockey | King and Low-Heywood Thomas (Scrim.) | Away | 4:00 p.m. | ||
| Wed., 9/7 | V Girls Soccer | Greens Farms Academy (Scrim.) | Away | 3:30 p.m. | ||
| Wed., 9/7 | V Girls Volleyball | Jamboree at Staples | Away | 4:00 p.m. | ||
| Fri., 9/9 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 9/9 | JV Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Field Hockey | Norwalk | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | L 1-3 | |
| Fri., 9/9 | JV Field Hockey | Norwalk | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | FR Field Hockey | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away | 4:00 p.m. | ||
| Sat., 9/10 | V Football | Greenwich | Home - Westhill Football Field [Directions] | 3:00 p.m. | L 16-22 | |
| Sat., 9/10 | FR Boys Soccer | Wilton | Home - Westhill Front Turf Field [Directions] | 1:30 p.m. | ||
| Sat., 9/10 | V Girls Soccer | Wilton | Home - Westhill Front Turf Field [Directions] | 3:00 p.m. | W 7-1 | |
| Sat., 9/10 | JV Girls Soccer | Wilton | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 9/10 | V Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 11:30 a.m. | L 2-3 | |
| Sat., 9/10 | JV Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 10:00 a.m. | ||
| Mon., 9/12 | JV Football | Greenwich | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | V Boys Soccer | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 9/12 | JV Boys Soccer | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 9/12 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 1-5 | |
| Mon., 9/12 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/12 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 6:00 p.m. | W 3-2 | |
| Mon., 9/12 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:45 p.m. | ||
| Tue., 9/13 | V Boys Cross Country | Ridgefield, Greenwich, Stamford | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Cross Country | Ridgefield, Greenwich, Stamford | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | FR Field Hockey | Ridgefield | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 7-1 | |
| Wed., 9/14 | V Boys Soccer | Danbury | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 9/14 | JV Boys Soccer | Danbury | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 9/14 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | T 1-1(OT) | |
| Wed., 9/14 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | T 4-4 | |
| Wed., 9/14 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 9/14 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ||
| Wed., 9/14 | FR Girls Volleyball | Stamford | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | FR Football | Greenwich | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 7:30 p.m. | W 45-16 | |
| Fri., 9/16 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 5:00 p.m. | L 2-3 | |
| Fri., 9/16 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Fri., 9/16 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 2-3 | |
| Fri., 9/16 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Fri., 9/16 | FR Girls Volleyball | Wilton | Home - Westhill New Gym [Directions] | 4:30 p.m. | ||
| Sat., 9/17 | JV Football | Bridgeport Central | Home - Westhill Football Field [Directions] | 10:30 a.m. | ||
| Sat., 9/17 | FR Boys Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | V Girls Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | 12:30 p.m. | W 2-0 | |
| Sat., 9/17 | JV Girls Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | 2:30 p.m. | ||
| Mon., 9/19 | V Girls Volleyball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/19 | JV Girls Volleyball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 9/20 | JV Boys Soccer | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 9/21 | V Boys Cross Country | Danbury, Fairfield Warde, Fairfield Ludlowe | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Girls Cross Country | Danbury, Fairfield Warde, Fairfield Ludlowe | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:15 p.m. | W 4-2 | |
| Wed., 9/21 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Wed., 9/21 | V Girls Swimming and Diving | St. Joseph | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Girls Volleyball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 9/21 | JV Girls Volleyball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/21 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | FR Football | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/22 | JV Boys Soccer | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 9/22 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | V Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 0-4 | |
| Thu., 9/22 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | FR Field Hockey | Staples | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | W 5-3 | |
| Fri., 9/23 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/23 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 9/23 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | FR Girls Volleyball | Greenwich | Home - Westhill New Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | V Football | Trumbull | Home - Westhill Football Field [Directions] | 1:30 p.m. | L 19-49 | |
| Sat., 9/24 | V Field Hockey | Bethel | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | W 5-0 | |
| Sat., 9/24 | JV Field Hockey | Bethel | Home - Westhill Front Turf Field [Directions] | 12:00 p.m. | ||
| Mon., 9/26 | JV Football | Trumbull | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/26 | V Boys Soccer | Trinity Catholic | Away - Gaglio Field | 4:00 p.m. | W 10-1 | |
| Mon., 9/26 | V Girls Soccer | Trinity Catholic | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 7-1 | |
| Mon., 9/26 | V Girls Volleyball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/26 | JV Girls Volleyball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Boys Cross Country | Wilton, Darien | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Cross Country | Wilton, Darien | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Field Hockey | Darien | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 9/27 | JV Field Hockey | Darien | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | V Boys Soccer | New Canaan | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-1 | |
| Wed., 9/28 | JV Boys Soccer | New Canaan | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 9/28 | JV Girls Volleyball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | V Girls Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | T 1-1 | |
| Thu., 9/29 | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | W 4-2 | |
| Fri., 9/30 | V Girls Volleyball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/30 | JV Girls Volleyball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | New Canaan | Home - Westhill Football Field [Directions] | 2:30 p.m. | L 7-35 | |
| Sat., 10/1 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 3:00 p.m. | L 0-2 | |
| Sat., 10/1 | FR Boys Soccer | Staples | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Tue., 10/4 | JV Football | New Canaan | Home - Westhill Football Field [Directions] | Cancelled | Cancelled | |
| Wed., 10/5 | V Boys Cross Country | St. Joseph, Trumbull, Staples | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Wed., 10/5 | V Boys Soccer | Trumbull | Home - Westhill Football Field [Directions] | 4:00 p.m. | L 1-4 | |
| Wed., 10/5 | JV Boys Soccer | Trumbull | Home - Westhill Football Field [Directions] | 5:15 p.m. | ||
| Wed., 10/5 | FR Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/5 | V Girls Cross Country | St. Joseph, Trumbull, Staples | Away [Directions] | 4:00 p.m. | ||
| Wed., 10/5 | V Field Hockey | Danbury | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 5-1 | |
| Wed., 10/5 | JV Field Hockey | Danbury | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 10/5 | FR Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 10/5 | V Girls Swimming and Diving | Wilton | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/5 | V Girls Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 10/5 | JV Girls Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/5 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | FR Field Hockey | Trumbull | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Thu., 10/6 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/6 | JV Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 5:00 p.m. | ||
| Thu., 10/6 | FR Girls Soccer | Trumbull | Home - Westhill Front Turf Field [Directions] | Cancelled | Cancelled | |
| Fri., 10/7 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/7 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | FR Boys Soccer | Stamford | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | L 2-4 | |
| Fri., 10/7 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | ||
| Fri., 10/7 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/7 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/7 | FR Girls Volleyball | Staples | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/8 | V Field Hockey | Wilton | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | L 0-9 | |
| Sat., 10/8 | JV Field Hockey | Wilton | Home - Westhill Front Turf Field [Directions] | 12:00 p.m. | ||
| Sat., 10/8 | V Girls Soccer | Stamford | Home - Westhill Football Field [Directions] | 1:30 p.m. | W 3-0 | |
| Sat., 10/8 | JV Girls Soccer | Stamford | Home - Westhill Football Field [Directions] | 11:00 a.m. | ||
| Sat., 10/8 | V Girls Volleyball | Immaculate | Home - Westhill - Main Gymnasium [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 10/8 | JV Girls Volleyball | Immaculate | Home - Westhill - Main Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | JV Girls Volleyball | Masuk | Home - Westhill - Main Gymnasium [Directions] | Cancelled | Cancelled | |
| Mon., 10/10 | V Boys Cross Country | New Canaan, Brien McMahon, Norwalk, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | V Boys Soccer | St. Joseph | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | W 2-1 | |
| Mon., 10/10 | JV Boys Soccer | St. Joseph | Home - Westhill Front Turf Field [Directions] | 9:00 a.m. | ||
| Mon., 10/10 | V Girls Cross Country | New Canaan, Brien McMahon, Norwalk, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | V Field Hockey | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/10 | JV Field Hockey | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 10/10 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | FR Field Hockey | New Canaan | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 10/11 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 10/11 | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | FR Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | L 0-2 | |
| Thu., 10/13 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Girls Soccer | Staples | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | T 4-4 | |
| Thu., 10/13 | JV Girls Soccer | Staples | Home - Westhill Front Turf Field [Directions] | 4:45 p.m. | ||
| Thu., 10/13 | V Girls Volleyball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 1-3 | |
| Thu., 10/13 | JV Girls Volleyball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | FR Boys Soccer | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/14 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 3:30 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/14 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Stamford | Away - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/15 | V Football | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 1:30 p.m. | W 21-0 | |
| Sat., 10/15 | V Girls Soccer | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 2:00 p.m. | W 3-0 | |
| Sat., 10/15 | JV Girls Soccer | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | ||
| Sat., 10/15 | FR Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | Cancelled | Cancelled | |
| Mon., 10/17 | JV Football | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/17 | JV Field Hockey | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 0-2 | |
| Mon., 10/17 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | FR Girls Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | Cancelled | Cancelled | |
| Mon., 10/17 | V Girls Volleyball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/17 | JV Girls Volleyball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | L 1-2 | |
| Tue., 10/18 | JV Boys Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | FR Boys Soccer | Darien | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 10/19 | JV Field Hockey | Stamford | Home [Directions] | 4:45 p.m. | ||
| Wed., 10/19 | V Girls Soccer | Darien | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/19 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Wed., 10/19 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | FR Girls Volleyball | Fairfield Ludlowe | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | FR Football | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 5:00 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:15 p.m. | W 2-1 | |
| Thu., 10/20 | JV Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 5:15 p.m. | ||
| Thu., 10/20 | FR Boys Soccer | Norwalk | Home - Rippowam Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 10/20 | V Field Hockey | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | W 2-0 | |
| Thu., 10/20 | JV Field Hockey | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 4:45 p.m. | ||
| Thu., 10/20 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | W 2-1 | |
| Fri., 10/21 | JV Girls Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | Cancelled | Cancelled | |
| Fri., 10/21 | V Girls Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/21 | JV Girls Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/21 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/22 | V Football | Norwalk | Home - Westhill Football Field [Directions] | 3:00 p.m. | W 12-11 | |
| Sat., 10/22 | V Boys Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | 1:00 p.m. | L 0-1 | |
| Sat., 10/22 | JV Boys Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/24 | JV Football | Norwalk | Home - Westhill Football Field [Directions] | 3:30 p.m. | ||
| Mon., 10/24 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | FR Field Hockey | Wilton | Away - Wilton HS - Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | JV Girls Soccer | Darien | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 10/24 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Darien | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | V Field Hockey | Greenwich | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | L 1-3 | |
| Wed., 10/26 | JV Field Hockey | Greenwich | Home - Westhill Front Turf Field [Directions] | 4:45 p.m. | ||
| Wed., 10/26 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/26 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 10/26 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | FR Girls Volleyball | Trumbull | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/28 | FR Football | Trinity Catholic | Away - Gaglio Field | 4:00 p.m. | ||
| Fri., 10/28 | V Girls Swimming and Diving | Trumbull | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/29 | V Football | Trinity Catholic | Home - Westhill Football Field [Directions] | 1:30 p.m. | L 14-28 | |
| Tue., 11/1 | V Boys Soccer | Norwalk (Scrim.) | Home - Westhill Front Field [Directions] | 3:30 p.m. | ||
| Thu., 11/3 | FR Football | Ridgefield | Home - Rippowam Turf Field [Directions] | 3:30 p.m. | ||
| Fri., 11/4 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 3-55 | |
| Sat., 11/5 | JV Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 10:30 a.m. | ||
| Thu., 11/10 | FR Football | St. Joseph | Home - Rippowam Turf Field [Directions] | 3:00 p.m. | ||
| Sat., 11/12 | V Football | St. Joseph | Away - St. Joseph HS [Directions] | 1:30 p.m. | L 14-19 | |
| Mon., 11/14 | JV Football | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 11/17 | FR Football | Stamford | Home - Westhill Football Field [Directions] | 3:00 p.m. | ||
| Thu., 11/24 | V Football | Stamford | Away - Stamford HS [Directions] | 10:30 a.m. | W 29-6 | |
| Sat., 12/3 | V Girls Ice Hockey | FCIAC Jamboree | Away - Shelton Rinks | 6:00 p.m. | ||
| Sat., 12/3 | JV Girls Ice Hockey | Taft (Scrim.) | Away - The Taft School | 2:00 p.m. | ||
| Sat., 12/3 | JV Girls Ice Hockey | Taft (Scrim.) | Away - The Taft School | 2:00 p.m. | ||
| Wed., 12/7 | V Girls Ice Hockey | Farmington (Scrim.) | Home - Terry Conners Ice Rink [Directions] | 7:00 p.m. | ||
| Fri., 12/9 | V Boys Basketball | Weston (Scrim.) | Away [Directions] | 5:00 p.m. | ||
| Fri., 12/9 | V Girls Basketball | St. Lukes (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/9 | JV Girls Basketball | St. Lukes (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 12/10 | V Boys Ice Hockey | HS Hockey Jamboree | Home - Terry Connors [Directions] | 5:00 p.m. | ||
| Mon., 12/12 | V Boys Basketball | Career Magnet (Scrim.) | Home [Directions] | 5:00 p.m. | ||
| Mon., 12/12 | V Girls Basketball | Shelton | Away - Shelton HS Gym [Directions] | 6:00 p.m. | W 52-39 | |
| Mon., 12/12 | JV Girls Basketball | Shelton | Away - Shelton HS Gym [Directions] | 4:15 p.m. | ||
| Mon., 12/12 | FR Girls Basketball | Shelton | Away - Shelton HS Gym [Directions] | Cancelled | Cancelled | |
| Wed., 12/14 | V Boys Basketball | New Milford (Scrim.) | Home [Directions] | 5:00 p.m. | ||
| Wed., 12/14 | V Wrestling | Stamford | Home - Westhill - New Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/14 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:50 p.m. | Junior Varsity contest | |
| Fri., 12/16 | V Girls Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 37-47 | |
| Fri., 12/16 | JV Girls Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/16 | FR Girls Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | Cancelled | Cancelled | |
| Sat., 12/17 | V Boys Swimming and Diving | Norwalk Relays | Away | 1:00 p.m. | ||
| Sat., 12/17 | V Wrestling | Londonderry Holiday Tournament | Away | 8:00 a.m. | ||
| Sat., 12/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners Ice Rink [Directions] | 8:30 p.m. | L 1-5 | |
| Sun., 12/18 | JV Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 9:00 p.m. | Junior Varsity game | |
| Mon., 12/19 | V Boys Basketball | Hamden (Scrim.) | Away - HHS Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/20 | V Boys Swimming and Diving | Ridgefield | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 53-31 | |
| Tue., 12/20 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | King and Low-Heywood Thomas | Home - Terry Connors [Directions] | 6:20 p.m. | W 8-5 | |
| Wed., 12/21 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 4:15 p.m. | L 4-6 | |
| Thu., 12/22 | V Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:50 p.m. | L 0-7 | |
| Fri., 12/23 | V Boys Basketball | Wilton | Away [Directions] | 5:00 p.m. | L 48-78 | |
| Fri., 12/23 | JV Boys Basketball | Wilton | Away [Directions] | 3:15 p.m. | ||
| Fri., 12/23 | FR Boys Basketball | Wilton | Away [Directions] | 2:00 p.m. | ||
| Fri., 12/23 | V Girls Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | L 32-51 | |
| Fri., 12/23 | JV Girls Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 3:00 p.m. | ||
| Mon., 12/26 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Terry Connors [Directions] | 5:30 p.m. | W 10-1 | |
| Tue., 12/27 | V Boys Indoor Track | Trumbull, New Canaan, Danbury, Ridgefield | Away [Directions] | TBA | ||
| Tue., 12/27 | V Girls Indoor Track | Trumbull, Danbury, New Canaan, Ridgefield | Away - wilton [Directions] | TBA | ||
| Wed., 12/28 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Terry Connors [Directions] | 6:20 p.m. | L 1-4 | |
| Wed., 12/28 | V Girls Basketball | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | W 45-37 | |
| Thu., 12/29 | V Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 7:30 p.m. | W 62-57 | |
| Thu., 12/29 | V Wrestling | Staples, Darien, Ridgefield | Away - Staples Field House [Directions] | 12:00 p.m. | ||
| Fri., 12/30 | V Boys Basketball | Trumbull | Away [Directions] | TBA | L 46-52 | |
| Fri., 12/30 | V Boys Ice Hockey | New Fairfield | Home - Terry Connors [Directions] | 2:00 p.m. | L 1-2 | |
| Fri., 12/30 | V Wrestling | Trumbull Duals | Away | 8:00 a.m. | ||
| Fri., 12/30 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | 6:00 p.m. | L 33-63 | |
| Tue., 1/3 | V Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 73-56 | |
| Tue., 1/3 | JV Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:45 p.m. | W 49-32 | |
| Tue., 1/3 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/4 | V Wrestling | Wilton | Away [Directions] | 4:30 p.m. | ||
| Wed., 1/4 | V Girls Gymnastics | Staples, New Canaan | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | 55.5 | |
| Wed., 1/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 5:30 p.m. | L 2-5 | |
| Thu., 1/5 | V Girls Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 50-48 | |
| Thu., 1/5 | JV Girls Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 47-38 | |
| Fri., 1/6 | JV Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Indoor Track | Stamford, Ridgefield, Fairfield Warde, Trumbull | Away - staples [Directions] | 10:00 a.m. | ||
| Sat., 1/7 | V Wrestling | Warde Invitational | Away | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | Stamford, Ridgefield, Fairfield Warde, Trumbull | Away - Staples [Directions] | 10:00 a.m. | ||
| Mon., 1/9 | V Boys Ice Hockey | Guilford | Away - East Haven Ice Rink [Directions] | 5:00 p.m. | L 7-8 | |
| Mon., 1/9 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | ||
| Mon., 1/9 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Westport PAL Longshore Rink [Directions] | 6:00 p.m. | ||
| Mon., 1/9 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Westport PAL Rink Longshore [Directions] | 6:00 p.m. | Junior varsity game | |
| Tue., 1/10 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 7:00 p.m. | L 55-56(OT) | |
| Tue., 1/10 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 46-54 | |
| Tue., 1/10 | JV Girls Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | W 6-0 | |
| Wed., 1/11 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | ||
| Wed., 1/11 | V Wrestling | Danbury | Home - Westhill - New Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | 6:30 p.m. | W 10- 5 | |
| Thu., 1/12 | JV Girls Ice Hockey | New Canaan | Away - Veterans Park [Directions] | 3:30 p.m. | Junior Varsity game | |
| Fri., 1/13 | V Boys Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 39-46 | |
| Fri., 1/13 | JV Boys Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | L 42-55 | |
| Fri., 1/13 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 6:00 p.m. | L 2-8 | |
| Sat., 1/14 | V Boys Ice Hockey | South Windsor | Home - Terry Connors [Directions] | 2:00 p.m. | W 3-2 | |
| Sat., 1/14 | V Boys Indoor Track | Greenwich, St. Joseph, Bridgeport Central, Brien McMahon | Away - Staples [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | V Wrestling | Law Pan-Prez Duals | Away | 9:00 a.m. | ||
| Sat., 1/14 | V Girls Ice Hockey | Hall/Conard | Home - Terry Conners Ice Rink [Directions] | 8:10 p.m. | L 0-7 | |
| Sat., 1/14 | V Girls Indoor Track | Greenwich, St. Joseph, Bridgeport Central, Brien McMahon | Away - staples [Directions] | 10:00 a.m. | ||
| Mon., 1/16 | V Wrestling | Fordham Prep (NY) | Away | Cancelled | Cancelled | |
| Mon., 1/16 | V Girls Gymnastics | Trumbull, New Canaan | Away - Next Dimension Gymnastics [Directions] | 5:30 p.m. | 78.2 | |
| Tue., 1/17 | V Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 76-95 | |
| Tue., 1/17 | JV Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:45 p.m. | L 45-60 | |
| Tue., 1/17 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | 7:00 p.m. | W 6-4 | |
| Wed., 1/18 | V Boys Swimming and Diving | New Canaan | Home - Westhill Pool [Directions] | 3:00 p.m. | ||
| Wed., 1/18 | V Girls Gymnastics | New Canaan, Fairfield Ludlowe, Fairfield Warde | Home - Westhill - New Gymnasium [Directions] | Cancelled | Cancelled | |
| Wed., 1/18 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 3:30 p.m. | W 2-1 | |
| Fri., 1/20 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | L 54-62 | |
| Fri., 1/20 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 3:45 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Danbury | Home - Westhill Pool [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 40-26 | |
| Fri., 1/20 | JV Girls Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Darien | Home - Terry Connors [Directions] | 5:20 p.m. | L 2-3(OT) | |
| Sat., 1/21 | V Boys Indoor Track | Greenwich, Ridgefield, Danbury, Stamford | Away - Wilton [Directions] | 9:30 a.m. | ||
| Sat., 1/21 | V Boys Swimming and Diving | Glastonbury | Away - Glastonbury HS Pool [Directions] | 3:00 p.m. | ||
| Sat., 1/21 | V Wrestling | Warde Quad | Away | 4:00 p.m. | ||
| Sat., 1/21 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 3:20 p.m. | L 0-7 | |
| Sat., 1/21 | V Girls Indoor Track | Greenwich, Ridgefield, Danbury, Stamford | Away - Wilton [Directions] | 9:30 a.m. | ||
| Sun., 1/22 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 6:10 p.m. | ||
| Sun., 1/22 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 7:20 p.m. | ||
| Sun., 1/22 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 7:30 p.m. | Junior Varsity game | |
| Tue., 1/24 | V Boys Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 55-42 | |
| Tue., 1/24 | JV Boys Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | L 40-58 | |
| Tue., 1/24 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | Cancelled | Cancelled | |
| Tue., 1/24 | V Girls Gymnastics | Darien, New Canaan, Fairfield Ludlowe, Fairfield Warde | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | 95.5 | |
| Wed., 1/25 | V Boys Ice Hockey | Trinity Catholic | Home - Terry Connors [Directions] | 6:20 p.m. | W 9-3 | |
| Wed., 1/25 | V Wrestling | Norwalk | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/25 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | 7:00 p.m. | L 0-7 | |
| Thu., 1/26 | V Girls Gymnastics | Greenwich, New Canaan | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 106.95 | |
| Thu., 1/26 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | L 0-8 | |
| Fri., 1/27 | V Boys Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 46-64 | |
| Fri., 1/27 | JV Boys Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Darien | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 21-49 | |
| Fri., 1/27 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | St. Joseph | Home - Terry Connors [Directions] | 2:00 p.m. | W 3-0 | |
| Sat., 1/28 | V Boys Indoor Track | Danbury, Greenwich, Trumbull, Stamford | Away - Staples [Directions] | 2:00 p.m. | ||
| Sat., 1/28 | V Wrestling | Ridgefield Challenge | Away | 8:00 a.m. | ||
| Sat., 1/28 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 8:45 p.m. | L 1-6 | |
| Sat., 1/28 | JV Girls Ice Hockey | Choate Rosemary Hall | Away - William C. S. Remsen Arena | 2:30 p.m. | Junior Varsity game | |
| Sat., 1/28 | V Girls Indoor Track | Danbury, Greenwich, Trumbull, Stamford | Away - staples [Directions] | 2:00 p.m. | ||
| Sun., 1/29 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 12:00 p.m. | ||
| Sun., 1/29 | JV Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 7:30 p.m. | ||
| Mon., 1/30 | V Boys Ice Hockey | Scarsdale (NY) | Home - Terry Connors [Directions] | 7:50 p.m. | W 4-3 | |
| Wed., 2/1 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 7:00 p.m. | L 54-57 | |
| Wed., 2/1 | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/1 | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/1 | V Wrestling | Greenwich | Away - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 2/1 | V Girls Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 44-54 | |
| Wed., 2/1 | JV Girls Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 6:30 p.m. | L 4-5(OT) | |
| Thu., 2/2 | V Boys Indoor Track | Danbury, Greenwich, St. Joseph, Fairfield Warde | Away - Hillhouse HS [Directions] | 4:30 p.m. | ||
| Thu., 2/2 | V Girls Gymnastics | Wilton | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | 102.5 | |
| Thu., 2/2 | V Girls Indoor Track | Bridgeport Central, Danbury, Brien McMahon, Fairfield Warde | Away - Hillhouse HS [Directions] | 4:30 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | W 65-60 | |
| Fri., 2/3 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Wilton | Away [Directions] | 3:40 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 54-69 | |
| Fri., 2/3 | JV Girls Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | 8:00 p.m. | T 3-3(OT) | |
| Sat., 2/4 | V Wrestling | New Fairfield Duals | Away | 8:00 a.m. | ||
| Sat., 2/4 | V Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 2:00 p.m. | L 0-6 | |
| Mon., 2/6 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 8:30 p.m. | W 7-4 | |
| Tue., 2/7 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | W 56-48 | |
| Tue., 2/7 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Tue., 2/7 | V Wrestling | Trumbull | Away - Auxiliary gym [Directions] | 6:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 49-43 | |
| Tue., 2/7 | JV Girls Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | JV Girls Ice Hockey | New Canaan | Away - New Canaan Winter Club [Directions] | 4:15 p.m. | Junior Varsity Game | |
| Wed., 2/8 | V Boys Basketball | Prince Tech | Away - Prince Tech [Directions] | 6:30 p.m. | L 64-69 | |
| Wed., 2/8 | JV Boys Basketball | Prince Tech | Away - Prince Tech [Directions] | 5:00 p.m. | ||
| Wed., 2/8 | FR Boys Basketball | Prince Tech | Away - Prince Tech [Directions] | 3:30 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 8:30 p.m. | W 3-2 | |
| Wed., 2/8 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/8 | V Girls Ice Hockey | Branford | Home - Terry Conners Ice Rink [Directions] | 4:30 p.m. | L 0-3 | |
| Fri., 2/10 | V Boys Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 66-68 | |
| Fri., 2/10 | JV Boys Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/10 | FR Boys Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/10 | V Wrestling | FCIAC Tournament | Away | TBA | ||
| Fri., 2/10 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | W 58-52 | |
| Fri., 2/10 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | 5:30 p.m. | W 5-2 | |
| Sat., 2/11 | V Wrestling | FCIAC Tournament | Away | 9:30 a.m. | ||
| Sat., 2/11 | V Girls Gymnastics | FCIAC Championships | Away - Johnathan Law | 10:30 p.m. | ||
| Sat., 2/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | 8:10 p.m. | L 3-7 | |
| Mon., 2/13 | V Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 46-60 | |
| Mon., 2/13 | JV Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 52-57 | |
| Mon., 2/13 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | L 42-59 | |
| Wed., 2/15 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Terry Connors [Directions] | 7:30 p.m. | L 2-3 | |
| Wed., 2/15 | V Girls Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 65-52 | |
| Wed., 2/15 | JV Girls Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Girls Gymnastics | Ro Carlucci tournament | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | 5:30 p.m. | L 2-4 | |
| Fri., 2/17 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:00 p.m. | ||
| Fri., 2/17 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 7:20 p.m. | L 1-9 | |
| Sat., 2/18 | V Boys Ice Hockey | New Canaan | Home - Terry Connors [Directions] | 6:20 p.m. | L 1-3 | |
| Sat., 2/18 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | ||
| Sat., 2/18 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners Ice Rink [Directions] | 8:20 p.m. | W 6-4 | |
| Mon., 2/20 | V Boys Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 60-65 | |
| Mon., 2/20 | JV Boys Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 2:00 p.m. | L 2-6 | |
| Tue., 2/21 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 2/22 | V Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 62-57 | |
| Wed., 2/22 | JV Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 2/25 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Thu., 3/2 | V Boys Ice Hockey | East Haven Coop | Home - Terry Connors [Directions] | 7:20 p.m. | L 5-8 | |
| Fri., 3/3 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 4:00 p.m. | ||
| Sat., 3/4 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 9:00 a.m. | ||
| Tue., 3/21 | V Softball | Stamford (Scrim.) | Away - Stamford HS [Directions] | 3:45 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Westhill Jamboree | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 3/25 | V Softball | Darien (Scrim.) | Away [Directions] | 10:30 a.m. | ||
| Tue., 3/28 | V Boys Lacrosse | Immaculate (Scrim.) | Home - Westhill Football Field [Directions] | 4:15 p.m. | ||
| Tue., 3/28 | V Girls Lacrosse | Stratford/Bunnell (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Baseball | Fordham Prep (NY) (Scrim.) | Away | 5:00 p.m. | ||
| Thu., 3/30 | V Baseball | Amity (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Boys Lacrosse | Notre Dame-Fairfield (Scrim.) | Home - Westhill Football Field [Directions] | 4:15 p.m. | ||
| Thu., 3/30 | V Boys Tennis | Fairfield Prep (Scrim.) | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Girls Lacrosse | Foran (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | JV Girls Lacrosse | Foran (Scrim.) | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 3/31 | V Boys Tennis | Fairfield Prep (Scrim.) | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/3 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 4/3 | V Girls Tennis | Wilton | Home [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 4/4 | V Boys Lacrosse | North Salem (NY) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 10-1 | |
| Tue., 4/4 | V Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 2-18 | |
| Tue., 4/4 | JV Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/5 | V Boys Outdoor Track | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Boys Tennis | Bridgeport Central | Home [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/5 | V Girls Outdoor Track | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Fri., 4/7 | V Boys Lacrosse | Trinity Catholic | Away - Trinity Gaglio Field | 7:30 p.m.p.m. | W 11-6 | |
| Sat., 4/8 | V Baseball | Jonathan Law | Away - Jonathan Law HS Baseball Field [Directions] | 11:00 a.m. | W 10-1 [Detailed Results] | |
| Sat., 4/8 | JV Baseball | Jonathan Law | Away [Directions] | 11:00 a.m. | ||
| Sat., 4/8 | FR Baseball | Jonathan Law | Away - Jonathan Law HS Baseball Field [Directions] | 2:00 p.m. | ||
| Mon., 4/10 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 3:30 p.m. | L 1-0 [Detailed Results] | |
| Mon., 4/10 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 3:00 p.m. | ||
| Mon., 4/10 | FR Baseball | Wilton | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/10 | V Girls Lacrosse | Bethel | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | L 6-7 | |
| Mon., 4/10 | JV Girls Lacrosse | Bethel | Home - Westhill Front Turf Field [Directions] | 12:30 p.m. | ||
| Mon., 4/10 | V Softball | Wilton | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 3-2 | |
| Tue., 4/11 | V Boys Lacrosse | Bunnell-Stratford | Home - Westhill Football Field [Directions] | 3:45 p.m. | W 7-6 [Detailed Results] | |
| Tue., 4/11 | JV Boys Lacrosse | Bunnell-Stratford | Home - Westhill Football Field [Directions] | 5:15 p.m. | ||
| Tue., 4/11 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 6-18 | |
| Wed., 4/12 | V Baseball | Bridgeport Central | Home - Westhill Baseball Field [Directions] | 12:00 p.m. | W 17-0 [Detailed Results] | |
| Wed., 4/12 | JV Baseball | Bridgeport Central | Home - Rippowam MS [Directions] | 12:00 p.m. | ||
| Wed., 4/12 | FR Boys Lacrosse | Shelton | Home - Westhill Front Turf Field [Directions] | Cancelled | Cancelled | |
| Wed., 4/12 | V Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 4:00 p.m. | W 13-0 | |
| Wed., 4/12 | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:00 p.m. | ||
| Wed., 4/12 | V Girls Tennis | Norwalk | Home - shippan raquet club [Directions] | 1:30 p.m. | W 7-0 | |
| Thu., 4/13 | FR Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 10:00 a.m. | ||
| Thu., 4/13 | V Boys Lacrosse | Greenwich | Home - Westhill Football Field [Directions] | 5:15 p.m. | L 2-14 | |
| Thu., 4/13 | JV Boys Lacrosse | Greenwich | Home - Westhill Football Field [Directions] | 3:30 p.m. | ||
| Thu., 4/13 | V Girls Lacrosse | Newington | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | W 15-3 | |
| Thu., 4/13 | JV Girls Lacrosse | Newington | Home - Westhill Front Turf Field [Directions] | 12:30 p.m. | ||
| Fri., 4/14 | FR Boys Lacrosse | Danbury | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 4/15 | V Baseball | Joel Barlow | Home - Westhill Baseball Field [Directions] | 12:00 p.m. | W 9-2 [Detailed Results] | |
| Sat., 4/15 | JV Baseball | Joel Barlow | Home - Rippowam MS [Directions] | 12:00 p.m. | ||
| Sat., 4/15 | FR Baseball | Joel Barlow | Away [Directions] | 12:00 p.m. | ||
| Sat., 4/15 | V Softball | Norwich Free Academy | Away - Rec Dept Softball Field [Directions] | 1:00 p.m. | L 3-8 | |
| Mon., 4/17 | V Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | W 3-1 [Detailed Results] | |
| Mon., 4/17 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Baseball | Norwalk | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Tennis | Danbury | Home [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/17 | V Girls Outdoor Track | Trumbull, Ridgefield | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Softball | Norwalk | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 12-10 | |
| Mon., 4/17 | JV Softball | Norwalk | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Girls Tennis | Danbury | Away - WCSU Tennis Courts, Westside Campus [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/18 | V Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:00 p.m. | L 2-6 [Detailed Results] | |
| Tue., 4/18 | JV Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | FR Baseball | Weston | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | Greenwich. 157 Westhill 192 | |
| Tue., 4/18 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | L 18-1 | |
| Tue., 4/18 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/18 | V Boys Outdoor Track | Ridgefield, Trumbull | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Fairfield Warde | Home [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/18 | V Girls Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 12-15 | |
| Tue., 4/18 | JV Girls Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/18 | V Softball | Fryeburg (ME) | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 4/18 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 4/19 | V Baseball | Danbury | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 2-0 [Detailed Results] | |
| Wed., 4/19 | JV Baseball | Danbury | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Boys Golf | Darien | Away - CC of Darien [Directions] | 3:15 p.m. | Darien. 165 Westhill. 182 | |
| Wed., 4/19 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 4:00 p.m. | W 15-7 | |
| Wed., 4/19 | JV Softball | Danbury | Away - Hatters Park Softball Fields [Directions] | 3:45 p.m. | ||
| Thu., 4/20 | V Boys Golf | St. Joseph | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Westhill. 168 St. Joseph. 178 | |
| Thu., 4/20 | V Boys Lacrosse | Stratford | Away - Penders Field [Directions] | 7:00 p.m. | L 7-4 | |
| Thu., 4/20 | JV Boys Lacrosse | Stratford | Away - Penders Field [Directions] | 5:30 p.m. | ||
| Thu., 4/20 | V Girls Lacrosse | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 8-10 | |
| Thu., 4/20 | JV Girls Lacrosse | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 4/21 | FR Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:00 p.m. | ||
| Sat., 4/22 | V Baseball | Fairfield Warde | Home - Westhill Baseball Field [Directions] | 3:00 p.m. | W 8-0 [Detailed Results] | |
| Sat., 4/22 | JV Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 12:00 p.m. | ||
| Sat., 4/22 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 2:30 p.m. | ||
| Sat., 4/22 | V Boys Lacrosse | Danbury | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | W 6-3 | |
| Sat., 4/22 | JV Boys Lacrosse | Danbury | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Mon., 4/24 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:00 p.m. | W 13-1 [Detailed Results] | |
| Mon., 4/24 | JV Baseball | Trinity Catholic | Away - Rippowam | 4:00 p.m. | ||
| Mon., 4/24 | FR Baseball | Trinity Catholic | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | Staples. 151 Westhill. 179 | |
| Mon., 4/24 | V Boys Tennis | St. Joseph | Home [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/24 | V Softball | Trinity Catholic | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 13-1 | |
| Mon., 4/24 | JV Softball | Trinity Catholic | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Girls Tennis | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 4/25 | V Boys Lacrosse | Wilton | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | L 4-16 | |
| Tue., 4/25 | JV Boys Lacrosse | Wilton | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | Greenwich | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 5-22 | |
| Tue., 4/25 | JV Girls Lacrosse | Greenwich | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Boys Golf | New Canaan | Home - Hubbard Brennan Golf Course [Directions] | 3:00 p.m. | New Canaan. 158 Westhill. 173 | |
| Wed., 4/26 | FR Boys Lacrosse | Shelton | Away - Shelton HS - Lower Field [Directions] | Cancelled | Cancelled | |
| Wed., 4/26 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 3-12 | |
| Wed., 4/26 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Thu., 4/27 | V Boys Lacrosse | Stamford | Home - Westhill Football Field [Directions] | 5:30 p.m. | L 6-7 | |
| Thu., 4/27 | JV Boys Lacrosse | Stamford | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 4/27 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Thu., 4/27 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/27 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Thu., 4/27 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | 4:30 p.m. | W 7-1 | |
| Thu., 4/27 | JV Softball | St. Joseph | Away - Long Hill Administration field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Baseball | Trumbull | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 5-3 | |
| Fri., 4/28 | JV Baseball | Trumbull | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:15 p.m. | W 6-0 | |
| Fri., 4/28 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/29 | V Baseball | St. Joseph | Home - Westhill Baseball Field [Directions] | 12:00 p.m. | W 9-7 | |
| Sat., 4/29 | JV Baseball | St. Joseph | Home - Rippowam MS [Directions] | 12:00 p.m. | ||
| Sat., 4/29 | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 12:00 p.m. | ||
| Sat., 4/29 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 1:00 p.m. | L 5-8 | |
| Sat., 4/29 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 11:00 a.m. | ||
| Sat., 4/29 | V Boys Tennis | Trumbull | Home [Directions] | 3:00 p.m. | L 3-4 | |
| Sat., 4/29 | V Girls Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 1:00 p.m. | L 5-12 | |
| Sat., 4/29 | JV Girls Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 11:00 p.m. | ||
| Sat., 4/29 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 11:00 a.m. | L 1-2(9) | |
| Sat., 4/29 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Mon., 5/1 | V Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 8-6 | |
| Mon., 5/1 | JV Baseball | Staples | Away - Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | FR Baseball | Staples | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | Fairfield Ludlowe. 169 Westhill. 182 | |
| Mon., 5/1 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 5/1 | V Girls Lacrosse | Jonathan Law | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | W 14-11 | |
| Mon., 5/1 | V Girls Outdoor Track | Staples, Bridgeport Central | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Softball | Staples | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 9-3 | |
| Mon., 5/1 | JV Softball | Staples | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Girls Tennis | Greenwich | Home [Directions] | 4:00 p.m. | L 6-1 | |
| Tue., 5/2 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 5:30 p.m. | L 3-19 | |
| Tue., 5/2 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | Staples, Bridgeport Central | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 5/2 | V Softball | Southington | Away - Softball Varsity Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 5/2 | V Girls Tennis | Fairfield Ludlowe | Home [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 5/3 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 5/3 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | FR Baseball | Greenwich | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Westhill. 173 Norwalk. 210 | |
| Wed., 5/3 | FR Boys Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | L 9-18 | |
| Wed., 5/3 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Wed., 5/3 | V Softball | Greenwich | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 9-0 | |
| Wed., 5/3 | JV Softball | Greenwich | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Girls Tennis | Staples | Home [Directions] | 4:00 p.m. | L 2-5 | |
| Thu., 5/4 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | L 5-6 | |
| Thu., 5/4 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | FR Baseball | Fairfield Ludlowe | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Golf | Stamford, Trinity Catholic | Away - Sterling Farms [Directions] | 3:15 p.m. | Stamford. 176 Westhill. 178 Trinity. 205 | |
| Thu., 5/4 | V Boys Tennis | Brien McMahon | Home [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/4 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 13-12 | |
| Thu., 5/4 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 5/5 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 6:00 p.m. | L 3-8 | |
| Sat., 5/6 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | L 3-15 | |
| Sat., 5/6 | JV Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 2:30 p.m. | ||
| Mon., 5/8 | V Baseball | Brien McMahon | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 12-0 | |
| Mon., 5/8 | JV Baseball | Brien McMahon | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | Westhill. 176 Wilton. 196 | |
| Mon., 5/8 | V Boys Outdoor Track | Greenwich, Danbury | Away - Cardinal Stadium [Directions] | 3:45 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Ridgefield | Home [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/8 | V Girls Outdoor Track | Danbury, Greenwich | Away - Danbury HS Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 16-0 | |
| Mon., 5/8 | JV Softball | Brien McMahon | Away - Brookside Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Girls Tennis | Ridgefield | Away [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 5/9 | V Boys Golf | Ridgefield | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Ridge field. 157 Westhill. 160 | |
| Tue., 5/9 | V Boys Lacrosse | Staples | Home - Westhill Football Field [Directions] | 5:30 p.m. | L 1-19 | |
| Tue., 5/9 | JV Boys Lacrosse | Staples | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/9 | V Softball | Fairfield Ludlowe | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 5/9 | JV Softball | Fairfield Ludlowe | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Darien | Home [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 5/10 | V Baseball | Ridgefield | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 5/10 | JV Baseball | Ridgefield | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Golf | Brien McMahon | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Westhill. 162 McMahon. 233 | |
| Wed., 5/10 | JV Boys Tennis | Wilton (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | W 8-5 | |
| Wed., 5/10 | JV Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | W 3-0(9) | |
| Wed., 5/10 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 6-0 | |
| Thu., 5/11 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 10-8 | |
| Thu., 5/11 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | FR Baseball | Darien | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Stamford | Away [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 5/11 | JV Girls Lacrosse | Bethel | Home - Westhill Front Turf Field [Directions] | Cancelled | Cancelled | |
| Thu., 5/11 | V Softball | Darien | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 5/11 | V Girls Tennis | Stamford | Home [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 5/12 | FR Boys Lacrosse | Stamford | Home - Westhill Front Field [Directions] | 4:30 p.m. | ||
| Fri., 5/12 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | W 4-3 | |
| Fri., 5/12 | V Girls Tennis | Trinity Catholic | Home [Directions] | 4:00 p.m. | W 7-0 | |
| Sat., 5/13 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | L 3-9 | |
| Sat., 5/13 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 1:30 p.m. | ||
| Sat., 5/13 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 10:00 a.m. | L 8-16 | |
| Sat., 5/13 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 11:30 a.m. | ||
| Mon., 5/15 | V Baseball | Stamford | Away - Cubetta Stadium [Directions] | 4:00 p.m. | W 19-3 | |
| Mon., 5/15 | JV Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | FR Baseball | Stamford | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Boys Tennis | New Canaan | Home [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 5/15 | V Girls Outdoor Track | Stamford | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Softball | Stamford | Home - Westhill Varsity Softball Field [Directions] | 5:00 p.m. | W 1-0 | |
| Mon., 5/15 | JV Softball | Stamford | Home - Roxbury School [Directions] | 3:00 p.m. | ||
| Mon., 5/15 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 5/16 | V Boys Golf | Fairfield Warde | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Warde. 167 Westhill. 169 | |
| Tue., 5/16 | V Boys Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | L 3-18 | |
| Tue., 5/16 | JV Boys Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 5/16 | V Girls Lacrosse | King and Low-Heywood Thomas | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | ||
| Tue., 5/16 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 6:30 p.m. | W 3-2 | |
| Wed., 5/17 | V Baseball | New Canaan | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 5-4 | |
| Wed., 5/17 | JV Baseball | New Canaan | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Boys Golf | Danbury | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Danbury. 171 Westhill. 180 | |
| Wed., 5/17 | V Boys Outdoor Track | Stamford | Home - Westhill Football Field [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | V Softball | Seymour | Away - Seymour HS [Directions] | 6:30 p.m. | L 1-5 | |
| Wed., 5/17 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | V Baseball | Greenwich | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 8-5 | |
| Thu., 5/18 | V Boys Lacrosse | King and Low-Heywood Thomas | Home - Westhill Football Field [Directions] | Cancelled | Cancelled | |
| Fri., 5/19 | V Softball | Norwalk | Home - Westhill Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Tue., 5/23 | V Boys Golf | Stamford, Trumbull | Home - Hubbard Brennan Golf Course [Directions] | Cancelled | Cancelled | |
| Tue., 5/23 | V Softball | St. Joseph | Away - Sacret Heart University [Directions] | 5:00 p.m. | W 6-5 | |
| Wed., 5/24 | V Softball | Darien | Away - Sacret Heart University [Directions] | 5:00 p.m. | ||
| Sat., 6/3 | V Baseball | Staples | Home - Westhill Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 12/14 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | ||
| Thu., 12/14 | JV Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | ||