| Westhill 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 655 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | ||
| TBA | V Boys Outdoor Track | Wilton | Away - WHS Track [Directions] | TBA | ||
| TBA | V Girls Tennis | Brien McMahon | Home - Westhill Tennis Courts [Directions] | TBA | W 4-3 | |
| Mon., 8/31 | V Girls Soccer | Joel Barlow (Scrim.) | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 8/31 | JV Girls Soccer | Joel Barlow (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/2 | V Boys Soccer | New Fairfield (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | V Football | Jonathan Law (Scrim.) | Home - Westhill Football Field [Directions] | 3:30 p.m. | ||
| Thu., 9/3 | V Girls Volleyball | staples jamboree | Away | 3:30 p.m. | ||
| Fri., 9/4 | V Girls Soccer | St. Lukes (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 9/5 | V Boys Soccer | King and Low-Heywood Thomas (Scrim.) | Away | 10:00 a.m. | ||
| Tue., 9/8 | V Boys Soccer | Shelton (Scrim.) | Away - Shelton HS Finn Stadium [Directions] | 6:30 p.m. | ||
| Tue., 9/8 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away | 3:30 p.m. | ||
| Wed., 9/9 | V Field Hockey | King and Low-Heywood Thomas (Scrim.) | Away | 4:00 p.m. | ||
| Wed., 9/9 | V Girls Soccer | Greens Farms Academy (Scrim.) | Away | 3:30 p.m. | ||
| Fri., 9/11 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | L 0-4 | |
| Fri., 9/11 | JV Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/11 | V Girls Soccer | Danbury | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 9/11 | JV Girls Soccer | Danbury | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 9/11 | V Girls Swimming and Diving | Fairfield Warde | Home - Westhill Pool [Directions] | 4:00 p.m. | Westhill 101 Fairfield Warde 76 | |
| Fri., 9/11 | V Girls Volleyball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 9/11 | FR Girls Volleyball | Fairfield Warde (Scrim.) | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 9/12 | V Football | Bridgeport Central | Home - Westhill Football Field [Directions] | 2:30 p.m. | W 27-6 | |
| Sat., 9/12 | FR Boys Soccer | Danbury | Home - Westhill Front Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 9/12 | V Field Hockey | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-1 | |
| Sat., 9/12 | JV Field Hockey | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 9/15 | V Boys Cross Country | Danbury, Wilton, Staples | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | JV Football | Bridgeport Central | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | FR Football | Bridgeport Central | Home - Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | V Boys Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | L 0-4 | |
| Tue., 9/15 | JV Boys Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | 5:45 p.m. | ||
| Tue., 9/15 | FR Boys Soccer | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | V Girls Cross Country | Danbury, Wilton, Staples | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Wed., 9/16 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 0-5 | |
| Wed., 9/16 | JV Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 9/16 | V Girls Swimming and Diving | Staples | Home - Westhill Pool [Directions] | 3:15 p.m. | Westhill 90 Staples 96 | |
| Wed., 9/16 | V Girls Volleyball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/16 | JV Girls Volleyball | Danbury | Home [Directions] | 5:30 p.m. | ||
| Wed., 9/16 | FR Girls Volleyball | Fairfield Warde (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Thu., 9/17 | FR Football | Greenwich | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/17 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 3-1 | |
| Thu., 9/17 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Thu., 9/17 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | L 0-6 | |
| Thu., 9/17 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| Thu., 9/17 | FR Field Hockey | Wilton | Home [Directions] | 4:00 p.m. | ||
| Fri., 9/18 | V Girls Soccer | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 9/18 | JV Girls Soccer | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 9/18 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | Westhill 103 Trumbull 83 | |
| Fri., 9/18 | V Girls Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 9/18 | JV Girls Volleyball | New Canaan (Scrim.) | Home [Directions] | 5:30 p.m. | ||
| Sat., 9/19 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 12:00 p.m. | L 1-5 | |
| Sat., 9/19 | JV Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 12:00 p.m. | ||
| Sat., 9/19 | FR Boys Soccer | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/21 | V Boys Cross Country | Fairfield Warde, Darien, Stamford | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Mon., 9/21 | JV Football | Greenwich | Away [Directions] | 4:00 p.m. | ||
| Mon., 9/21 | V Girls Cross Country | Fairfield Warde, Darien, Stamford | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Mon., 9/21 | V Field Hockey | Staples | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 9/21 | JV Field Hockey | Staples | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 9/21 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | Cancelled | Cancelled | |
| Mon., 9/21 | V Girls Soccer | Fairfield Warde | Home - Westhill Football Field [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 9/21 | JV Girls Soccer | Fairfield Warde | Home - Westhill Football Field [Directions] | 5:30 p.m. | ||
| Mon., 9/21 | V Girls Swimming and Diving | Ridgefield | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Mon., 9/21 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 9/21 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ||
| Mon., 9/21 | FR Girls Volleyball | Danbury | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/22 | V Boys Soccer | Trinity Catholic | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | W 5-0 | |
| Thu., 9/24 | FR Football | Trumbull | Home - Rippowam Turf Field [Directions] | 3:15 p.m. | ||
| Thu., 9/24 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 0-9 | |
| Thu., 9/24 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 9/24 | FR Field Hockey | Darien | Home [Directions] | Cancelled | Cancelled | |
| Thu., 9/24 | V Girls Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | 4:00 p.m. | W 8-2 | |
| Thu., 9/24 | V Girls Volleyball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/24 | JV Girls Volleyball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/25 | V Football | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | L 21-54 | |
| Fri., 9/25 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | T 2-2 | |
| Fri., 9/25 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 9/25 | V Girls Soccer | New Canaan | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/25 | JV Girls Soccer | New Canaan | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 9/25 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 9/25 | FR Girls Volleyball | Staples | Away [Directions] | Cancelled | Cancelled | |
| Sat., 9/26 | V Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 10:00 a.m. | L 1-2 | |
| Sat., 9/26 | JV Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 11:30 a.m. | ||
| Mon., 9/28 | JV Football | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | V Boys Soccer | Staples | Home - Westhill Football Field [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 9/28 | JV Boys Soccer | Staples | Home - Westhill Front Turf Field [Directions] | 5:15 p.m. | ||
| Mon., 9/28 | FR Boys Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | V Field Hockey | Stamford | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 9/28 | JV Field Hockey | Stamford | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 9/28 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/28 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Boys Cross Country | St. Joseph, Greenwich, Brien McMahon | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Cross Country | St. Joseph, Greenwich, Brien McMahon | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 1-4 | |
| Tue., 9/29 | JV Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/30 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | L 1-3 | |
| Wed., 9/30 | JV Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | ||
| Wed., 9/30 | FR Boys Soccer | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/30 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | L 1-4 | |
| Wed., 9/30 | JV Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 5:30 p.m. | ||
| Wed., 9/30 | FR Field Hockey | Danbury | Home [Directions] | Cancelled | Cancelled | |
| Wed., 9/30 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 9/30 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/30 | FR Girls Volleyball | Fairfield Warde | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | FR Football | New Canaan | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Girls Soccer | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 10/1 | JV Girls Soccer | Trumbull | Home - Westhill Front Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 10/2 | V Boys Soccer | Stamford | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | T 2-2 | |
| Fri., 10/2 | JV Boys Soccer | Stamford | Home - Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 10/2 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | L 1-3 | |
| Fri., 10/2 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Fri., 10/2 | FR Girls Volleyball | New Canaan | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 10/5 | V Football | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | L 12-55 | |
| Mon., 10/5 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Mon., 10/5 | V Field Hockey | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 10/5 | JV Field Hockey | Trumbull | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 10/5 | FR Field Hockey | Trumbull | Away - Indian Ledge Turf [Directions] | Cancelled | Cancelled | |
| Mon., 10/5 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 10/5 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 10/5 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 10/5 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 10/5 | FR Girls Volleyball | New Canaan | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Boys Cross Country | Ridgefield, Fairfield Ludlowe, Trumbull | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | T 2-2 | |
| Tue., 10/6 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Ridgefield, Fairfield Ludlowe, Trumbull | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | V Girls Soccer | St. Joseph | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 10/7 | JV Girls Soccer | St. Joseph | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | V Girls Volleyball | Staples | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/7 | JV Girls Volleyball | Staples | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Boys Soccer | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 10/8 | JV Boys Soccer | Fairfield Ludlowe | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | FR Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/8 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | FR Field Hockey | Fairfield Ludlowe | Home [Directions] | Cancelled | Cancelled | |
| Fri., 10/9 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:30 p.m. | L 0-2 | |
| Fri., 10/9 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 10/9 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | ||
| Fri., 10/9 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/9 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/9 | FR Girls Volleyball | Trumbull | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/10 | V Field Hockey | New Canaan | Home - Westhill Front Turf Field [Directions] | 3:00 p.m. | L 0-4 | |
| Sat., 10/10 | JV Field Hockey | New Canaan | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 10/10 | FR Field Hockey | New Canaan | Away - NCHS Track Field [Directions] | Cancelled | Cancelled | |
| Mon., 10/12 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 0-1 | |
| Mon., 10/12 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/12 | FR Boys Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | 12:00 p.m. | ||
| Mon., 10/12 | V Field Hockey | St. Joseph | Home - Westhill Front Turf Field [Directions] | 3:00 p.m. | W 2-1 | |
| Mon., 10/12 | JV Field Hockey | St. Joseph | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 10/13 | V Boys Cross Country | New Canaan, Trinity Catholic, Norwalk, Bridgeport Central | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | New Canaan, Trinity Catholic, Norwalk, Bridgeport Central | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-4 | |
| Tue., 10/13 | JV Girls Soccer | Ridgefield | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Volleyball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 10/13 | JV Girls Volleyball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | FR Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Boys Soccer | Darien | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 10/14 | JV Boys Soccer | Darien | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | FR Boys Soccer | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Girls Swimming and Diving | Danbury | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 10/14 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | FR Girls Volleyball | St. Joseph | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | FR Football | Fairfield Ludlowe | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 2-3 | |
| Thu., 10/15 | JV Field Hockey | Stamford | Away [Directions] | 5:00 p.m. | ||
| Thu., 10/15 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 10/15 | JV Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | V Boys Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/16 | JV Boys Soccer | Norwalk | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | FR Boys Soccer | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/16 | V Girls Volleyball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/16 | JV Girls Volleyball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | FR Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/17 | V Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 2:00 p.m. | L 6-7 | |
| Sat., 10/17 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 3-2 | |
| Sat., 10/17 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Sat., 10/17 | V Girls Soccer | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 3:00 p.m. | W 4-0 | |
| Sat., 10/17 | JV Girls Soccer | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 1:00 p.m. | ||
| Mon., 10/19 | JV Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | ||
| Mon., 10/19 | FR Field Hockey | Greenwich | Home [Directions] | Cancelled | Cancelled | |
| Mon., 10/19 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Mon., 10/19 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/19 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | FR Girls Volleyball | Ridgefield | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 10/20 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/21 | V Boys Soccer | Wilton | Home - Westhill Front Turf Field [Directions] | 4:15 p.m. | L 1-4 | |
| Wed., 10/21 | JV Boys Soccer | Wilton | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | FR Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:15 p.m. | ||
| Wed., 10/21 | V Girls Volleyball | Darien | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/21 | JV Girls Volleyball | Darien | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | FR Football | Norwalk | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 7:00 p.m. | L 2-3 | |
| Thu., 10/22 | JV Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:15 p.m. | ||
| Fri., 10/23 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | L 0-14 | |
| Fri., 10/23 | V Field Hockey | Ridgefield | Home - Westhill Front Turf Field [Directions] | 3:30 p.m. | L 0-2 | |
| Fri., 10/23 | JV Field Hockey | Ridgefield | Home - Westhill Front Turf Field [Directions] | 4:45 p.m. | ||
| Fri., 10/23 | V Girls Volleyball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 10/23 | JV Girls Volleyball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 10/24 | JV Football | Norwalk | Away - Testa Field, NHS [Directions] | 10:30 a.m. | ||
| Sat., 10/24 | FR Boys Soccer | New Canaan | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 10/26 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 10/26 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/26 | FR Boys Soccer | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | FR Boys Soccer | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Girls Soccer | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 10/27 | FR Girls Volleyball | Staples | Home [Directions] | 4:00 p.m. | ||
| Wed., 10/28 | V Field Hockey | Norwalk | Home - Testa Field, NHS [Directions] | 7:00 p.m. | L 0-11 | |
| Wed., 10/28 | JV Field Hockey | Norwalk | Home - Testa Field, NHS [Directions] | 5:30 p.m. | ||
| Wed., 10/28 | FR Field Hockey | Norwalk | Home - Westhill Front Turf Field [Directions] | Cancelled | Cancelled | |
| Wed., 10/28 | V Girls Volleyball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 3-2 | |
| Wed., 10/28 | JV Girls Volleyball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 10/29 | FR Football | Trinity Catholic | Home - Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | FR Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/30 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | ||
| Sat., 10/31 | V Football | Trinity Catholic | Away - Trinity Catholic Alumni Field | 1:00 p.m. | L 28-56 | |
| Sat., 10/31 | FR Boys Soccer | Stamford | Home - Westhill Front Turf Field [Directions] | Cancelled | Cancelled | |
| Mon., 11/2 | JV Football | Trinity Catholic | Away | Cancelled | Cancelled | |
| Mon., 11/2 | V Girls Volleyball | Bassick | Home [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 11/2 | JV Girls Volleyball | Bassick | Home [Directions] | 5:30 p.m. | ||
| Thu., 11/5 | FR Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Sat., 11/7 | V Football | Ridgefield | Home - Westhill Football Field [Directions] | 2:00 p.m. | L 7-45 | |
| Mon., 11/9 | JV Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Thu., 11/12 | FR Football | St. Joseph | Away - St. Joseph HS [Directions] | 3:00 p.m. | ||
| Sat., 11/14 | V Football | St. Joseph | Home - Westhill Football Field [Directions] | 1:00 p.m. | L 15-44 | |
| Mon., 11/16 | JV Football | Stamford | Home - Westhill Football Field [Directions] | 3:00 p.m. | ||
| Thu., 11/19 | FR Football | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 11/26 | V Football | Stamford | Home - Westhill Football Field [Directions] | 10:00 a.m. | W 15-0 | |
| Sat., 12/5 | V Girls Ice Hockey | FCIAC Jamboree | Away - Shelton Ice Rink | 4:00 p.m. | ||
| Wed., 12/9 | V Boys Basketball | Harding (Scrim.) | Away - Harding-Miska Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 12/12 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Terry Conners Ice Rink [Directions] | 2:10 p.m. | W 4-3 | |
| Mon., 12/14 | V Boys Basketball | New Milford (Scrim.) | Away - New Milford HS [Directions] | 4:30 p.m. | ||
| Tue., 12/15 | V Girls Basketball | St. Lukes (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 12/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 8:50 p.m. | W 5-1 | |
| Wed., 12/16 | V Wrestling | Brien McMahon | Home - Westhill New Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/16 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | 5:30 p.m. | W 2-0 | |
| Thu., 12/17 | V Boys Basketball | Hamden (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 12/19 | V Boys Basketball | Kolbe Cathedral (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 2:00 p.m. | ||
| Sat., 12/19 | V Boys Ice Hockey | EnricoFermi | Away - Enfield Twin Rinks | 4:30 p.m. | W 5-1 | |
| Sat., 12/19 | V Boys Swimming and Diving | Norwalk/Brien McMahon (Scrim.) | Away [Directions] | TBA | ||
| Sat., 12/19 | V Wrestling | Londonderry Holiday Tournament | Away | 8:00 a.m. | ||
| Sat., 12/19 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:20 p.m. | L 0-6 | Staples bus 6:30 pm separate |
| Mon., 12/21 | V Boys Basketball | Joel Barlow | Home - Main Gymnasium [Directions] | 7:00 p.m. | L 42-45 | |
| Mon., 12/21 | JV Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | FR Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 12/21 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | 8:00 p.m. | W 5-0 | |
| Mon., 12/21 | V Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 29-59 | |
| Mon., 12/21 | JV Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | FR Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 12/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | 7:30 p.m. | W 4-0 | |
| Wed., 12/23 | V Boys Basketball | Stratford | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 58-41 | |
| Wed., 12/23 | JV Boys Basketball | Stratford | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/23 | FR Boys Basketball | Stratford | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/23 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 45-30 | |
| Wed., 12/23 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/26 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 1:00 p.m. | T 3-3 | |
| Mon., 12/28 | V Boys Basketball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 79-76 | |
| Mon., 12/28 | JV Boys Basketball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 12/28 | FR Boys Basketball | Bassick | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 12/28 | V Wrestling | Norwalk | Away - Norwalk High Gym [Directions] | 9:00 a.m. | ||
| Mon., 12/28 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | 5:00 p.m. | L 21-56 | |
| Tue., 12/29 | V Boys Indoor Track | Wilton | Away [Directions] | TBA | ||
| Wed., 12/30 | V Boys Ice Hockey | Sheehan | Home - Terry Connors [Directions] | 5:50 p.m. | W 10-1 | |
| Wed., 12/30 | V Wrestling | Trumbull | Away [Directions] | 10:00 a.m. | ||
| Wed., 12/30 | V Girls Basketball | Wilton | Away - Stamford HS [Directions] | 3:00 p.m. | W 33-26 | |
| Sat., 1/2 | V Boys Ice Hockey | Masuk | Home - Terry Connors [Directions] | 2:10 p.m. | W 8-2 | |
| Sat., 1/2 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 7:00 p.m. | L 2-4 | Staples bus 5:00 pm separate bus |
| Mon., 1/4 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | L 1-5 | |
| Tue., 1/5 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 7:00 p.m. | L 56-77 | |
| Tue., 1/5 | JV Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ||
| Tue., 1/5 | FR Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Tue., 1/5 | V Wrestling | Staples | Home - Westhill New Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/5 | V Girls Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 26-42 | |
| Tue., 1/5 | JV Girls Basketball | Danbury | Home [Directions] | 5:15 p.m. | ||
| Tue., 1/5 | FR Girls Basketball | Danbury | Home [Directions] | 4:00 p.m. | ||
| Wed., 1/6 | V Boys Ice Hockey | Guilford | Home - Terry Connors [Directions] | 7:50 p.m. | T 1-1 | |
| Wed., 1/6 | V Girls Gymnastics | Staples | Home - Westhill New Gym [Directions] | 5:30 p.m. | 93.4 | |
| Wed., 1/6 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 1/7 | V Boys Basketball | Weston | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 66-42 | |
| Thu., 1/7 | JV Boys Basketball | Weston | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/7 | FR Boys Basketball | Weston | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | V Boys Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 57-54 | |
| Fri., 1/8 | JV Boys Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Boys Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | V Boys Swimming and Diving | Staples | Home - Westhill Pool [Directions] | 3:30 p.m. | Staples 102 Westhill 82 | |
| Fri., 1/8 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | L 40-73 | |
| Fri., 1/8 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/9 | V Boys Indoor Track | Staples | Away [Directions] | 10:00 a.m. | ||
| Sat., 1/9 | V Wrestling | Warde Invitational | Away | 8:30 a.m. | ||
| Mon., 1/11 | V Boys Ice Hockey | Norwalk | Home - Terry Connors [Directions] | 3:00 p.m. | W 9-3 | |
| Mon., 1/11 | V Girls Gymnastics | Trumbull | Home - Westhill New Gym [Directions] | 5:30 p.m. | 108 | |
| Tue., 1/12 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 51-66 | |
| Tue., 1/12 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Tue., 1/12 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Tue., 1/12 | V Girls Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | W 43-13 | |
| Tue., 1/12 | JV Girls Basketball | Brien McMahon | Home [Directions] | 4:00 p.m. | ||
| Tue., 1/12 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:45 p.m. | W 4-3(OT) | Staples separate bus 2:30 pm |
| Wed., 1/13 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/13 | V Wrestling | Greenwich | Home - Westhill - New Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 1/13 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 3:30 p.m. | W 3-2 | |
| Fri., 1/15 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 48-61 | |
| Fri., 1/15 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/15 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Boys Swimming and Diving | Trumbull | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/15 | V Girls Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 36-53 | |
| Fri., 1/15 | JV Girls Basketball | Fairfield Warde | Home [Directions] | Cancelled | Cancelled | |
| Fri., 1/15 | FR Girls Basketball | Fairfield Warde | Home [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Girls Ice Hockey | Northwest Catholic | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | W 3-1 | |
| Sat., 1/16 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 8:00 p.m. | L 1-4 | |
| Sat., 1/16 | V Boys Indoor Track | Staples | Away [Directions] | 10:00 a.m. | ||
| Sat., 1/16 | V Wrestling | Law PanPrez Duals | Away | 9:00 a.m. | ||
| Sat., 1/16 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 1/19 | V Boys Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 52-45 | |
| Tue., 1/19 | JV Boys Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/19 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | 5:45 p.m. | W 54-28 | |
| Tue., 1/19 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Wed., 1/20 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 6:50 p.m. | W 7-3 | |
| Wed., 1/20 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/20 | V Wrestling | Danbury | Away - Danbury HS - NEW gym [Directions] | 5:00 p.m. | ||
| Wed., 1/20 | V Girls Ice Hockey | New Canaan | Home [Directions] | 5:00 p.m. | L 0-3 | Terry Conners Rink |
| Thu., 1/21 | V Girls Gymnastics | New Milford | Away [Directions] | 5:00 p.m. | 110 | |
| Fri., 1/22 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | W 58-52 OT | |
| Fri., 1/22 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/22 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 5:00 p.m. | ||
| Fri., 1/22 | V Wrestling | Warde Quad | Away | Cancelled | Cancelled | |
| Fri., 1/22 | V Girls Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 43-29 | |
| Fri., 1/22 | JV Girls Basketball | New Canaan | Home [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | FR Girls Basketball | New Canaan | Home [Directions] | Cancelled | Cancelled | |
| Sat., 1/23 | V Boys Indoor Track | Staples | Away [Directions] | Cancelled | Cancelled | |
| Sat., 1/23 | V Boys Swimming and Diving | Glastonbury | Away - Glastonbury HS Pool [Directions] | Cancelled | Cancelled | |
| Tue., 1/26 | V Boys Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 59-45 | |
| Tue., 1/26 | JV Boys Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/26 | FR Boys Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/26 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | W 54-43 | |
| Tue., 1/26 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/26 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | Cancelled | Cancelled | |
| Wed., 1/27 | V Boys Ice Hockey | Greenwich | Home - Terry Connors [Directions] | 7:50 p.m. | L 3-6 | |
| Wed., 1/27 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/27 | V Wrestling | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 1/27 | V Girls Gymnastics | Greenwich | Home - Westhill New Gym [Directions] | 6:00 p.m. | 99.3 | |
| Wed., 1/27 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 1/28 | V Girls Ice Hockey | Branford | Home - Westport PAL Rink Longshore [Directions] | 7:30 p.m. | W 2-1 | |
| Fri., 1/29 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 40-57 | |
| Fri., 1/29 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/29 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/29 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 1/29 | V Girls Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 31-48 | |
| Fri., 1/29 | JV Girls Basketball | Trumbull | Home [Directions] | Cancelled | Cancelled | |
| Fri., 1/29 | FR Girls Basketball | Trumbull | Home [Directions] | 4:00 p.m. | ||
| Sat., 1/30 | V Boys Ice Hockey | Staples | Home - Terry Connors [Directions] | 4:00 p.m. | L 2-3 | |
| Sat., 1/30 | V Wrestling | Ridgefield Challenge | Away | 8:00 a.m. | ||
| Sat., 1/30 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | 2:10 p.m. | W 5-2 | |
| Mon., 2/1 | V Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 38-46 | |
| Mon., 2/1 | JV Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/1 | FR Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/1 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 35-75 | |
| Mon., 2/1 | JV Girls Basketball | Stamford | Away - Stamford HS [Directions] | Cancelled | Cancelled | |
| Mon., 2/1 | FR Girls Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 2/2 | V Wrestling | Ridgefield | Home - Westhill - New Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 2/2 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 8:30 p.m. | L 0-7 | Staples bus separate 6:45 pm |
| Wed., 2/3 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | W 54-52 | |
| Wed., 2/3 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ||
| Wed., 2/3 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Wed., 2/3 | V Boys Ice Hockey | Trumbull | Home - Terry Connors [Directions] | 7:20 p.m. | W 7-3 | |
| Wed., 2/3 | V Girls Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 43-48 | |
| Wed., 2/3 | JV Girls Basketball | St. Joseph | Home [Directions] | 4:00 p.m. | ||
| Wed., 2/3 | FR Girls Basketball | St. Joseph | Home [Directions] | Cancelled | Cancelled | |
| Wed., 2/3 | V Girls Gymnastics | Darien | Home - Westhill New Gym [Directions] | 5:30 p.m. | 107.4 | |
| Fri., 2/5 | V Wrestling | Warde Tri Meet | Away | 3:00 p.m. | ||
| Fri., 2/5 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/6 | V Boys Ice Hockey | Norwalk | Home - Terry Connors [Directions] | 6:30 p.m. | W 9-0 | |
| Sat., 2/6 | V Wrestling | New Fairfield Duals | Away | 8:00 a.m. | ||
| Sat., 2/6 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | 7:30 p.m. | L 1-2 | |
| Tue., 2/9 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | W 44-41 | |
| Tue., 2/9 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/9 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/9 | V Girls Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 42-57 | |
| Tue., 2/9 | JV Girls Basketball | Ridgefield | Home [Directions] | Cancelled | Cancelled | |
| Tue., 2/9 | FR Girls Basketball | Ridgefield | Home [Directions] | 4:00 p.m. | ||
| Tue., 2/9 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde, New Canaan | Away - Gymnastics Cheer Academy [Directions] | 6:30 p.m. | 101.45 | |
| Wed., 2/10 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 7:30 p.m. | W 6-2 | |
| Wed., 2/10 | V Wrestling | Stamford | Away - Stamford High Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/10 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | 4:00 p.m. | 104.1 | |
| Wed., 2/10 | V Girls Ice Hockey | Greenwich | Home [Directions] | 6:00 p.m. | L 0-1 | Terry Conners Rink |
| Thu., 2/11 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Thu., 2/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 2/12 | V Boys Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 55-45 | |
| Fri., 2/12 | JV Boys Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Boys Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Wrestling | FCIAC Tournament | Away | TBA | ||
| Fri., 2/12 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | L 39-57 | |
| Fri., 2/12 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:00 p.m. | L 0-3 | |
| Sat., 2/13 | V Wrestling | FCIAC Tournament | Away | TBA | ||
| Sat., 2/13 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 1:30 p.m. | L 33-48 | |
| Sat., 2/13 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/13 | V Girls Gymnastics | Jonathan Law | Away [Directions] | 10:30 p.m. | 103.4 | |
| Mon., 2/15 | V Boys Ice Hockey | Trinity Catholic | Home - Terry Connors [Directions] | 12:30 p.m. | W 8-1 | |
| Tue., 2/16 | V Boys Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 55-43 | |
| Tue., 2/16 | JV Boys Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/16 | FR Boys Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/16 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 3:00 p.m. | L 37-65 | |
| Tue., 2/16 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 1:30 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Ridgefield | Home - Terry Connors [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 2/17 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Thu., 2/18 | V Boys Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 56-55 | |
| Thu., 2/18 | JV Boys Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/18 | FR Boys Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/18 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 5:30 p.m. | L 1-2 | |
| Fri., 2/19 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:00 p.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Wilton | Home - Terry Connors [Directions] | 7:30 p.m. | W 4-2 | |
| Sat., 2/20 | V Boys Swimming and Diving | Wilton | Home - Westhill Pool [Directions] | 10:30 a.m.. | ||
| Sat., 2/20 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Girls Gymnastics | Ro Carlucci | Away | TBA | ||
| Mon., 2/22 | V Boys Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | L 54-63 | |
| Mon., 2/22 | JV Boys Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/22 | FR Boys Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 7:00 p.m. | W 82-58 | |
| Wed., 2/24 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/24 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/26 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 2/27 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Fri., 3/4 | V Wrestling | New England Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 3/5 | V Wrestling | New England Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Wed., 3/23 | V Baseball | Fordham Prep (NY) (Scrim.) | Away | 3:30 p.m. | ||
| Wed., 3/23 | V Softball | Bristol Central (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Wed., 3/23 | JV Softball | Bristol Central (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Sat., 3/26 | V Boys Lacrosse | Tournament Game - Opponent Not Known (Scrim.) | Home - Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Boys Lacrosse | Tournament Game - Opponent Not Known (Scrim.) | Home - Westhill Football Field [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Softball | Notre Dame-Fairfield (Scrim.) | Home - Westhill Varsity Softball Field [Directions] | 10:00 a.m. | ||
| Tue., 3/29 | V Baseball | St. Lukes (Scrim.) | Away | 3:30 p.m. | ||
| Tue., 3/29 | V Softball | Wilton (Scrim.) | Away - WHS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Girls Lacrosse | Notre Dame-Fairfield (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | JV Girls Lacrosse | Notre Dame-Fairfield (Scrim.) | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 3/31 | V Baseball | Brunswick School (Scrim.) | Away | 3:30 p.m. | ||
| Fri., 4/1 | V Baseball | Briarcliff (NY) (Scrim.) | Away | 3:30 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 12:45 p.m. | L 1-12 | |
| Sat., 4/2 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 4/2 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 1-16 | |
| Sat., 4/2 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/5 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | L 1-20 | |
| Tue., 4/5 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Baseball | Weston | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/6 | V Girls Outdoor Track | Wilton | Away - WHS Track [Directions] | 4:00 p.m. | ||
| Thu., 4/7 | V Girls Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 2-15 | |
| Thu., 4/7 | JV Girls Lacrosse | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 4/8 | V Boys Lacrosse | Trinity Catholic | Home - Westhill Football Field [Directions] | 4:30 p.m. | W 6-4 | |
| Fri., 4/8 | V Girls Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 8-12 | |
| Fri., 4/8 | JV Girls Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Sat., 4/9 | V Baseball | Jonathan Law | Home - Westhill Baseball Field [Directions] | 12:00 p.m. | W 6-0 | |
| Sat., 4/9 | JV Baseball | Jonathan Law | Home - Westhill Baseball Field [Directions] | 3:30 p.m. | ||
| Sat., 4/9 | FR Baseball | Jonathan Law | Home - Westhill Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/11 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | L 7-6 | |
| Mon., 4/11 | JV Baseball | Danbury | Away - Danbury HS Junior Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | FR Baseball | Danbury | Home - Westhill Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 4/11 | V Softball | Danbury | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | L 3-6 | |
| Mon., 4/11 | JV Softball | Danbury | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Boys Lacrosse | King and Low-Heywood Thomas | Away | 4:30 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | Wilton | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-15 | |
| Tue., 4/12 | JV Girls Lacrosse | Wilton | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 4/13 | V Baseball | Greenwich | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 18-6 | |
| Wed., 4/13 | JV Baseball | Greenwich | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Golf | Ridgefield, Stamford | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Ridgefield. 158 Westhill. 176 | |
| Wed., 4/13 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 4/13 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/13 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Boys Tennis | Danbury | Away - Danbury HS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 4/14 | V Girls Tennis | Danbury | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Fri., 4/15 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | L 2-8 | |
| Fri., 4/15 | JV Baseball | Brien McMahon | Away - Roton [Directions] | 4:00 p.m. | ||
| Fri., 4/15 | V Softball | Brien McMahon | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 14-2 | |
| Fri., 4/15 | JV Softball | Brien McMahon | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Sat., 4/16 | V Boys Lacrosse | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | 1:30 p.m. | W 15-2 | |
| Sat., 4/16 | V Girls Lacrosse | Ridgefield | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | L 1-17 | |
| Sat., 4/16 | JV Girls Lacrosse | Ridgefield | Home - Westhill Front Turf Field [Directions] | 11:30 a.m. | ||
| Mon., 4/18 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | W 9-6 | |
| Mon., 4/18 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | FR Baseball | Fairfield Warde | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | Greenwich. 162 Westhill. 174 | |
| Mon., 4/18 | V Boys Tennis | Trinity Catholic | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 4/18 | V Girls Outdoor Track | Trumbull | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Softball | Fairfield Warde | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 8-1 | |
| Mon., 4/18 | JV Softball | Fairfield Warde | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | W 7-0 | |
| Tue., 4/19 | V Boys Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | L 1-14 | |
| Tue., 4/19 | JV Boys Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | V Boys Outdoor Track | Trumbull | Home [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 4/19 | V Girls Lacrosse | Jonathan Law | Away - Jonathan Law HS Stadium [Directions] | 4:30 p.m. | W 12-11 | |
| Tue., 4/19 | JV Girls Lacrosse | Jonathan Law | Away - Jonathan Law HS Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/19 | V Softball | Norwich Free Academy | Away - Norwich Free Academy [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 4/19 | JV Softball | Norwich Free Academy | Away - Norwich Free Academy [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | V Girls Tennis | New Canaan | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Wed., 4/20 | V Baseball | Trinity Catholic | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/20 | JV Baseball | Trinity Catholic | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Boys Golf | Wilton | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Westhill. 164 Wilton. 181 | |
| Wed., 4/20 | V Softball | Trinity Catholic | Away - Westhill HS | 4:00 p.m. | W 11-3 | |
| Wed., 4/20 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/21 | V Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | L 1-2 | |
| Thu., 4/21 | JV Baseball | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | FR Baseball | New Canaan | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Golf | Trumbull, St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Trumbull. 168 Westhill. 191 St. Joseph. 192 | |
| Thu., 4/21 | V Boys Lacrosse | Stamford | Away - Stamford HS [Directions] | 7:30 p.m. | L 3-9 | |
| Thu., 4/21 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 4:30 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Staples | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 4/21 | V Girls Lacrosse | Staples | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 3-15 | |
| Thu., 4/21 | JV Girls Lacrosse | Staples | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Softball | New Canaan | Home - Westhill Varsity Softball Field [Directions] | 4:30 p.m. | W 11-4 | |
| Thu., 4/21 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Fri., 4/22 | V Boys Tennis | Greenwich | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Fri., 4/22 | JV Softball | New Canaan | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Sat., 4/23 | V Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 12:00 p.m. | W 8-0 | |
| Sat., 4/23 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:30 p.m. | L 2-14 | |
| Sat., 4/23 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:45 p.m. | ||
| Sat., 4/23 | V Girls Lacrosse | Bunnell | Home - Westhill Front Turf Field [Directions] | 1:00 p.m. | W 13-11 | |
| Sat., 4/23 | JV Girls Lacrosse | Bunnell | Home - Westhill Front Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 4/23 | V Softball | Oxford | Home - Westhill Varsity Softball Field [Directions] | 12:00 p.m. | W 13-0 | |
| Sat., 4/23 | JV Softball | Oxford | Home - Westhill Varsity Softball Field [Directions] | 2:00 p.m. | ||
| Mon., 4/25 | V Baseball | Staples | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 4/25 | JV Baseball | Staples | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Softball | Staples | Away - Wakeman Field [Directions] | 4:00 p.m. | W 10-1 | |
| Mon., 4/25 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Girls Tennis | Trumbull | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 4/26 | V Boys Golf | Norwalk, Brien McMahon | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Westhill. 169 Norwalk. 200 Brien McMahon. 224 | |
| Tue., 4/26 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | L 0-18 | |
| Tue., 4/26 | JV Boys Lacrosse | Wilton | Away - Whitten Field [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 1-19 | |
| Tue., 4/26 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | L 0-4 | |
| Wed., 4/27 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | FR Baseball | Trumbull | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Outdoor Track | Staples, Ridgefield | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 4/27 | V Girls Outdoor Track | Staples, Ridgefield | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Softball | Trumbull | Home - Westhill Varsity Softball Field [Directions] | 4:15 p.m. | W 3-0 | |
| Wed., 4/27 | JV Softball | Trumbull | Home - Roxbury Elementary School [Directions] | 4:15 p.m. | ||
| Thu., 4/28 | V Boys Tennis | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 4/28 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | L 6-12 | |
| Thu., 4/28 | JV Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | ||
| Thu., 4/28 | V Girls Tennis | St. Joseph | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 4/29 | V Baseball | Stamford | Home - Cubetta [Directions] | 7:00 p.m. | L 1-6 | |
| Fri., 4/29 | JV Baseball | Stamford | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:30 p.m. | ||
| Fri., 4/29 | V Softball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 6-5 | |
| Fri., 4/29 | JV Softball | Stamford | Home - Stamford HS [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Girls Tennis | Fairfield Warde | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Sat., 4/30 | JV Baseball | Weston | Home - Westhill Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 12:00 p.m. | L 1-11 | |
| Sat., 4/30 | JV Boys Lacrosse | Norwalk | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 5/2 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Ludlowe. 169 Westhill. 176 | |
| Mon., 5/2 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/3 | V Boys Golf | New Canaan | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | New Canaan. 154 Westhill. 168 | |
| Tue., 5/3 | V Boys Lacrosse | Ridgefield | Home - Westhill Football Field [Directions] | 5:30 p.m. | L 0-21 | |
| Tue., 5/3 | JV Boys Lacrosse | Ridgefield | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Danbury, Bridgeport Central | Away - Danbury HS Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Girls Lacrosse | Stamford | Home - Westhill Front Turf Field [Directions] | 5:15 p.m. | L 3-11 | |
| Tue., 5/3 | JV Girls Lacrosse | Stamford | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Danbury, Bridgeport Central | Away - Danbury HS Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | FR Boys Lacrosse | Joel Barlow | Home - Westhill Front Turf Field [Directions] | 5:15 p.m. | ||
| Wed., 5/4 | JV Softball | Fairfield Ludlowe | Away - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 2-3 | |
| Thu., 5/5 | JV Baseball | St. Joseph | Away - Madison MS, Trumbull [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | FR Baseball | St. Joseph | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Golf | Stamford, Trinity Catholic | Away [Directions] | 3:15 p.m. | Westhill. 188 Stamford. 231 Trinity. 211 | |
| Thu., 5/5 | V Boys Lacrosse | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 12-0 | |
| Thu., 5/5 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 6-17 | |
| Thu., 5/5 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Grass [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | W 8-6 | |
| Thu., 5/5 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 5/6 | V Boys Outdoor Track | New Britain | Away [Directions] | TBA | ||
| Fri., 5/6 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 4-15 | |
| Fri., 5/6 | JV Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 5/6 | V Girls Outdoor Track | New Britain | Away [Directions] | TBA | ||
| Sat., 5/7 | V Boys Lacrosse | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | 2:00 p.m. | L 0-13 | |
| Sat., 5/7 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 3:30 p.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | New Britain | Away [Directions] | TBA | ||
| Sat., 5/7 | V Girls Outdoor Track | New Britain | Away [Directions] | TBA | ||
| Mon., 5/9 | V Baseball | Darien | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | L 7-0 | |
| Mon., 5/9 | JV Baseball | Darien | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Golf | Darien, Stamford | Away - Wee Burn CC [Directions] | 3:15 p.m. | Darien. 158 Westhill. 178 | |
| Mon., 5/9 | V Boys Tennis | Norwalk | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/9 | V Girls Outdoor Track | Greenwich | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 6-4 | |
| Mon., 5/9 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Girls Tennis | Norwalk | Away - Norwalk HS [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/10 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | W 6-3 | |
| Tue., 5/10 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | FR Baseball | Ridgefield | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Golf | Bridgeport Central | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Westhill. 161 Central. 241 | |
| Tue., 5/10 | V Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | 5:30 p.m. | L 0-15 | |
| Tue., 5/10 | JV Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Outdoor Track | Greenwich | Home [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Girls Lacrosse | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 9-10 | |
| Tue., 5/10 | V Softball | Ridgefield | Home - Westhill Varsity Softball Field [Directions] | 4:30 p.m. | W 2-1 | |
| Tue., 5/10 | JV Softball | Ridgefield | Home - Roxbury Elementary School [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | V Baseball | Norwalk | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | L 6-7 | |
| Wed., 5/11 | JV Baseball | Norwalk | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Boys Lacrosse | Stamford | Home [Directions] | 5:15 p.m. | ||
| Wed., 5/11 | V Boys Tennis | Fairfield Ludlowe | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 5/11 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | 4:00 p.m. | W 21-2 | |
| Wed., 5/11 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/12 | V Girls Tennis | Wilton | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Fri., 5/13 | JV Baseball | Fairfield Ludlowe | Home - Rippowam MS [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | FR Boys Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Boys Tennis | Ridgefield | Away - Hardscrabble Club [Directions] | 2:30 p.m. | W 4-1 | |
| Fri., 5/13 | V Girls Tennis | Ridgefield | Home - Hardscrabble Club [Directions] | 7:00 p.m. | L 2-5 | |
| Sat., 5/14 | V Baseball | Fairfield Ludlowe | Home - Westhill Baseball Field [Directions] | 2:00 p.m. | L 2-5 | |
| Sat., 5/14 | V Baseball | Greenwich | Home - Cubeta Field [Directions] | 7:00 p.m. | W 5-2 | |
| Sat., 5/14 | V Boys Lacrosse | Brien McMahon | Home - Westhill Football Field [Directions] | 1:00 p.m. | L 1-8 | |
| Sat., 5/14 | JV Boys Lacrosse | Brien McMahon | Home - Westhill Football Field [Directions] | 2:30 p.m. | ||
| Sat., 5/14 | V Boys Tennis | Darien | Home - Westhill Tennis Courts [Directions] | 3:00 p.m. | L 3-4 | |
| Sat., 5/14 | V Softball | St. Joseph | Home - Westhill Varsity Softball Field [Directions] | 1:00 p.m. | L 2-5 | |
| Sat., 5/14 | JV Softball | St. Joseph | Home - Roxbury Elementary School [Directions] | 1:00 p.m. | ||
| Mon., 5/16 | V Baseball | Wilton | Home - Westhill Baseball Field [Directions] | 4:30 p.m. | W 1-0 | |
| Mon., 5/16 | JV Baseball | Wilton | Home - Rippowam MS [Directions] | 4:30 p.m. | ||
| Mon., 5/16 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Boys Golf | Staples, Norwalk | Away - Longshore [Directions] | 3:00 p.m. | Staples. 165 Westhill. 170 | |
| Mon., 5/16 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | L 3-14 | |
| Mon., 5/16 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Boys Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/16 | V Girls Lacrosse | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 7:00 p.m. | L 7-8 (OT) | |
| Mon., 5/16 | JV Girls Lacrosse | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 5:00 p.m. | ||
| Mon., 5/16 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | 6:30 p.m. | W 6-3 | |
| Mon., 5/16 | V Girls Tennis | Bridgeport Central | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/17 | V Boys Golf | Fairfield Warde | Home - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Westhill. 169 Warde. 171 | |
| Tue., 5/17 | V Boys Tennis | Stamford | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/17 | V Girls Lacrosse | Danbury | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 6-13 | |
| Tue., 5/17 | JV Girls Lacrosse | Danbury | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/17 | V Softball | John Jay (NY) | Away | 4:30 p.m. | W 12-3 | |
| Tue., 5/17 | V Girls Tennis | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/18 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | 4:00 p.m. | W 18-3 | |
| Wed., 5/18 | JV Baseball | Bridgeport Central | Away - Seaside Park Diamond 10 [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | FR Boys Lacrosse | Danbury | Home - Westhill Front Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Outdoor Track | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Outdoor Track | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Softball | Bridgeport Central | Home - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | W 9-0 | |
| Wed., 5/18 | JV Softball | Bridgeport Central | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Danbury. 155 Westhill. 178 | |
| Thu., 5/19 | V Softball | Seymour | Away - Seymour HS [Directions] | 4:30 p.m. | W 4-3 | |