| Westhill 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 751 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Brien McMahon | Home - Westhill Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Fairfield Warde | Home - TBA [Directions] | TBA | ||
| TBA | JV Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel HS [Directions] | TBA | ||
| TBA | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS [Directions] | TBA | ||
| TBA | FR Boys Soccer | Wilton | Home - Lione Park [Directions] | TBA | ||
| TBA | V Boys Swimming and Diving | Glastonbury | Away - Glastonbury HS Pool [Directions] | TBA | ||
| TBA | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | TBA | ||
| TBA | FR Field Hockey | Ridgefield | Home - Westhill Football Field [Directions] | TBA | ||
| TBA | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Fairfield Ludlowe | Home - TBA [Directions] | TBA | ||
| Mon., 8/27 | V Boys Soccer | Brunswick School (Scrim.) | Home - Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 8/27 | V Girls Soccer | Joel Barlow (Scrim.) | Home - Westhill Front Turf Field [Directions] | 2:30 p.m. | ||
| Mon., 8/27 | JV Girls Soccer | Joel Barlow (Scrim.) | Away - Field E (Softball) [Directions] | 2:30 p.m. | ||
| Thu., 8/30 | V Boys Soccer | Fairfield Warde (Scrim.) | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | JV Boys Soccer | Fairfield Warde (Scrim.) | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | V Girls Soccer | St. Lukes (Scrim.) | Away | L 6-0 | ||
| Fri., 8/31 | V Football | Brien McMahon (Scrim.) | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Fri., 8/31 | V Girls Soccer | Girls Soccer Jamboree | Away - Trinity Catholic HS | 5:00 p.m. | ||
| Tue., 9/4 | V Girls Soccer | Greens Farms Academy (Scrim.) | Away | 3:30 p.m. | ||
| Wed., 9/5 | V Boys Soccer | Brien McMahon (Scrim.) | Away - Pride Field (BMHS) [Directions] | 6:00 p.m. | ||
| Wed., 9/5 | V Girls Volleyball | Val Dickinson Jamboree | Away - Staples HS-Westport | 4:00 p.m. | ||
| Thu., 9/6 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | TBA | ||
| Thu., 9/6 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away | 3:45 p.m. | ||
| Fri., 9/7 | V Football | Fairfield Ludlowe | Away - Taft Field [Directions] | L 21-29 | ||
| Fri., 9/7 | FR Field Hockey | New Canaan | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | W 3-1 | ||
| Fri., 9/7 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | L 0-2 | ||
| Sat., 9/8 | JV Football | Fairfield Ludlowe | Home - J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 9/8 | FR Football | Fairfield Ludlowe | Home - J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/8 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | L 0-2 | ||
| Sat., 9/8 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 1:00 p.m. | ||
| Sat., 9/8 | FR Field Hockey | Trumbull | Home - Westhill Football Field [Directions] | 12:00 p.m. | ||
| Tue., 9/11 | V Boys Cross Country | Ridgefield, Darien, Stamford | Away - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Cross Country | Ridgefield, Darien, Stamford | Away - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 1-6 | ||
| Wed., 9/12 | V Boys Soccer | Bridgeport Central | Home - Westhill Front Turf Field [Directions] | W 3-0 | ||
| Wed., 9/12 | JV Boys Soccer | Bridgeport Central | Home - Lione Park [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | W 3-0 | ||
| Wed., 9/12 | JV Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Wed., 9/12 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | W 3-0 | ||
| Thu., 9/13 | FR Football | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Wilton | Home - Westhill Front Turf Field [Directions] | T 0-0 | ||
| Thu., 9/13 | JV Girls Soccer | Wilton | Home - Lione Park [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Boys Soccer | Wilton | Away - Allen's Field [Directions] | W 4-0 | ||
| Fri., 9/14 | JV Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Field Hockey | Greenwich | Home - Westhill Stadium [Directions] | L 0-2 | ||
| Fri., 9/14 | JV Field Hockey | Greenwich | Home - Westhill Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/14 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | Westhill 93 Danbury 73 | ||
| Fri., 9/14 | V Girls Volleyball | Bassick | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/14 | JV Girls Volleyball | Bassick | Home - Westhill - Main Gymnasium [Directions] | W 2-0 | ||
| Sat., 9/15 | V Boys Cross Country | Wilton Invitational | Away - Allen's Field | TBA | ||
| Sat., 9/15 | V Football | Norwalk | Home - J. Walter Kennedy Stadium [Directions] | L 21-48 | ||
| Sat., 9/15 | V Girls Cross Country | Wilton Invitational | Away - Allen's Field | TBA | ||
| Sat., 9/15 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | V Girls Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | W 4-1 | ||
| Sat., 9/15 | JV Girls Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 9/17 | V Boys Cross Country | New Canaan, St. Joseph, Greenwich | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | JV Football | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 5:15 p.m. | ||
| Mon., 9/17 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 3-2 | ||
| Mon., 9/17 | JV Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 5:00 p.m. | ||
| Mon., 9/17 | FR Boys Soccer | Norwalk | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Girls Cross Country | New Canaan, St. Joseph, Greenwich | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Field Hockey | Brien McMahon | Home - Westhill Stadium [Directions] | W 2-1(OT) | ||
| Mon., 9/17 | JV Field Hockey | Brien McMahon | Home - Westhill Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | V Girls Swimming and Diving | Fairfield Warde | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/17 | V Girls Volleyball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Mon., 9/17 | JV Girls Volleyball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | W 2-0 | ||
| Tue., 9/18 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-0 | ||
| Thu., 9/20 | FR Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 9/20 | V Field Hockey | Norwalk | Home - Westhill Stadium [Directions] | L 0-7 | ||
| Thu., 9/20 | JV Field Hockey | Norwalk | Home - Westhill Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/20 | FR Field Hockey | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Thu., 9/20 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | L 1-0 | ||
| Thu., 9/20 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/21 | V Boys Soccer | Danbury | Home - Westhill Front Turf Field [Directions] | L 1-5 | ||
| Fri., 9/21 | JV Boys Soccer | Danbury | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 3-0 | ||
| Fri., 9/21 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 2-0 | ||
| Fri., 9/21 | FR Girls Volleyball | Wilton | Home - Westhill - New Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 9/22 | V Boys Cross Country | Bowdoin Invitational | Away - Bowdoin Park/Wappingers Falls, NY | TBA | ||
| Sat., 9/22 | V Football | Danbury | Home - J. Walter Kennedy Stadium [Directions] | L 20-52 | ||
| Sat., 9/22 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | T 2-2 | ||
| Mon., 9/24 | JV Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | V Boys Soccer | Fairfield Warde | Home - Westhill Front Turf Field [Directions] | L 2-3 | ||
| Mon., 9/24 | JV Boys Soccer | Fairfield Warde | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | FR Boys Soccer | Fairfield Warde | Away - Fairfield Woods MS [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | V Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | W 3-0 | ||
| Mon., 9/24 | JV Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | L 1-2 | ||
| Wed., 9/26 | V Boys Soccer | Trinity Catholic | Away | W 7-0 | ||
| Wed., 9/26 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 1-3 | ||
| Wed., 9/26 | V Girls Volleyball | Danbury | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Wed., 9/26 | JV Girls Volleyball | Danbury | Home - Westhill - Main Gymnasium [Directions] | W 2-0 | ||
| Wed., 9/26 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Boys Cross Country | Wilton, Staples, Fairfield Ludlowe | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | FR Football | New Canaan | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Cross Country | Wilton, Staples, Fairfield Ludlowe | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 1-4 | ||
| Thu., 9/27 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Thu., 9/27 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | L 6-0 | ||
| Thu., 9/27 | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Swimming and Diving | Trumbull | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/28 | V Boys Soccer | St. Joseph | Home - Westhill Front Turf Field [Directions] | L 2-3 | ||
| Fri., 9/28 | JV Boys Soccer | St. Joseph | Home - Rippowam MS - Turf Field [Directions] | 4:15 p.m. | ||
| Fri., 9/28 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/28 | V Girls Volleyball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/28 | JV Girls Volleyball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | W 2-0 | ||
| Fri., 9/28 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/29 | V Football | New Canaan | Away - Dunning Stadium [Directions] | L 14-38 | ||
| Sat., 9/29 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | L 1-4 | ||
| Sat., 9/29 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | L 1-2 | ||
| Sat., 9/29 | JV Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | 3:45 p.m. | ||
| Mon., 10/1 | JV Football | New Canaan | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | V Boys Soccer | Trumbull | Home - Westhill Front Turf Field [Directions] | T 0-0 | ||
| Mon., 10/1 | JV Boys Soccer | Trumbull | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | FR Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | W 3-0 | ||
| Mon., 10/1 | JV Girls Volleyball | Trinity Catholic | Away | W 2-0 | ||
| Tue., 10/2 | V Boys Cross Country | Trumbull, Norwalk, Trinity Catholic | Away [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Cross Country | Trumbull, Norwalk, Trinity Catholic | Away [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Soccer | Staples | Home - Westhill Front Turf Field [Directions] | L 1-4 | ||
| Tue., 10/2 | JV Girls Soccer | Staples | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Field Hockey | Wilton | Home - Westhill Stadium [Directions] | L 1-8 | ||
| Wed., 10/3 | JV Field Hockey | Wilton | Home - Westhill Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/3 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Volleyball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | L 2-3 | ||
| Wed., 10/3 | JV Girls Volleyball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | W 2-0 | ||
| Wed., 10/3 | FR Girls Volleyball | St. Joseph | Away [Directions] | 4:30 p.m. | ||
| Thu., 10/4 | FR Football | Harding | Away - John L. Lewis Memorial Field @ Harding HS [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | L 0-1 | ||
| Thu., 10/4 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | FR Field Hockey | Wilton | Away [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Football | Capital/Achievement | Away - Annie Fisher Turf Field [Directions] | W 32-12 | ||
| Fri., 10/5 | V Field Hockey | Fitch | Away - Fitch HS-Baseball Field [Directions] | L 1-2 | ||
| Fri., 10/5 | JV Field Hockey | Fitch | Away - Fitch HS-Baseball Field [Directions] | Cancelled | ||
| Fri., 10/5 | V Girls Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | W 2-0 | ||
| Fri., 10/5 | JV Girls Soccer | Greenwich | Home - Rippowam MS - Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/5 | JV Girls Volleyball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | L 0-2 | ||
| Fri., 10/5 | FR Girls Volleyball | Trumbull | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/6 | FR Boys Soccer | Staples | Home - J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | ||
| Sat., 10/6 | V Girls Soccer | Trinity Catholic | Home - Westhill Front Turf Field [Directions] | W 6-1 | ||
| Mon., 10/8 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | T 2-2 | ||
| Mon., 10/8 | JV Boys Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/8 | FR Boys Soccer | Greenwich | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 10/8 | V Field Hockey | Staples | Away - Staples Stadium [Directions] | L 0-7 | ||
| Mon., 10/8 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | ||
| Mon., 10/8 | FR Field Hockey | Staples | Home - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Cross Country | Danbury, Brien McMahon, Fairfield Warde | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Cross Country | Danbury, Brien McMahon, Fairfield Warde | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | L 2-1 | ||
| Tue., 10/9 | JV Girls Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Boys Soccer | Brien McMahon | Home - Westhill Front Turf Field [Directions] | T 1-1 | ||
| Wed., 10/10 | JV Boys Soccer | Brien McMahon | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:15 p.m. | ||
| Wed., 10/10 | V Field Hockey | Darien | Home - Westhill Stadium [Directions] | L 0-6 | ||
| Wed., 10/10 | JV Field Hockey | Darien | Home - Westhill Football Field [Directions] | 5:30 p.m. | ||
| Wed., 10/10 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | W 3-1 | ||
| Wed., 10/10 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 1-2 | ||
| Thu., 10/11 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 10/11 | FR Girls Volleyball | Staples | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-1 | ||
| Fri., 10/12 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | L 0-3 | ||
| Fri., 10/12 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 10/12 | JV Girls Soccer | Stamford | Home - Westhill Front Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 10/12 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 3-2 | ||
| Fri., 10/12 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 1-2 | ||
| Fri., 10/12 | FR Girls Volleyball | Greenwich | Home - Westhill - New Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/13 | FR Boys Soccer | Fairfield Ludlowe | Home - J. Walter Kennedy Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/13 | V Girls Soccer | Stamford | Home - J. Walter Kennedy Stadium [Directions] | W 3-0 | ||
| Mon., 10/15 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 3-1 | ||
| Mon., 10/15 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | FR Boys Soccer | Stamford | Home - J. Walter Kennedy Stadium [Directions] | 4:15 p.m. | ||
| Mon., 10/15 | V Girls Soccer | Fairfield Ludlowe | Home - Westhill Front Turf Field [Directions] | L 1-2 | ||
| Mon., 10/15 | V Girls Volleyball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Mon., 10/15 | JV Girls Volleyball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | W 2-1 | ||
| Tue., 10/16 | V Field Hockey | Danbury | Home - Westhill Stadium [Directions] | L 1-2 | ||
| Tue., 10/16 | JV Field Hockey | Danbury | Home - Westhill Football Field [Directions] | 5:30 p.m. | ||
| Tue., 10/16 | V Girls Soccer | Darien | Home - Westhill Front Turf Field [Directions] | W 2-1 | ||
| Tue., 10/16 | JV Girls Soccer | Darien | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | FR Boys Soccer | Darien | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 1-3 | ||
| Wed., 10/17 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 1-2 | ||
| Wed., 10/17 | FR Girls Volleyball | Fairfield Ludlowe | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Boys Cross Country | FCIAC Championships | Away - Waveny Park-New Canaan | 2:15 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Darien | Away - DHS Stadium Field [Directions] | W 4-1 | ||
| Thu., 10/18 | JV Boys Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Girls Cross Country | FCIAC Championships | Away - Waveny Park-New Canaan | 2:15 p.m. | ||
| Thu., 10/18 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 0-6 | ||
| Fri., 10/19 | JV Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | W 3-1 | ||
| Fri., 10/19 | JV Girls Volleyball | Stamford | Away - Stamford High Aux Gym [Directions] | L 1-2 | ||
| Fri., 10/19 | FR Girls Volleyball | Stamford | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/20 | V Football | Greenwich | Home - J. Walter Kennedy Stadium [Directions] | L 0-53 | ||
| Sat., 10/20 | FR Football | Greenwich | Away - Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/20 | V Boys Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | W 5-0 | ||
| Sat., 10/20 | JV Boys Soccer | Ridgefield | Home - Westhill Front Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | V Field Hockey | Weston | Home - J. Walter Kennedy Stadium [Directions] | OT-L 1-2 | ||
| Sat., 10/20 | JV Field Hockey | Weston | Home - J. Walter Kennedy Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/20 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 12:00 p.m. | ||
| Mon., 10/22 | JV Football | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Field Hockey | Fairfield Ludlowe | Home - Westhill Stadium [Directions] | L 0-4 | ||
| Mon., 10/22 | JV Field Hockey | Fairfield Ludlowe | Home - Westhill Football Field [Directions] | 5:30 p.m. | ||
| Mon., 10/22 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | L 4-0 | ||
| Mon., 10/22 | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Swimming and Diving | St. Joseph | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/22 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-2 | ||
| Mon., 10/22 | FR Girls Volleyball | Darien | Home - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | V Boys Soccer | New Canaan | Home - Westhill Front Turf Field [Directions] | L 1-4 | ||
| Tue., 10/23 | JV Boys Soccer | New Canaan | Home - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | V Girls Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Wed., 10/24 | JV Girls Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | L 1-2 | ||
| Wed., 10/24 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/25 | FR Football | Trinity Catholic | Away - Gaglio Field | Cancelled | ||
| Fri., 10/26 | V Football | Trinity Catholic | Home - J. Walter Kennedy Stadium [Directions] | L 7-22 | ||
| Fri., 10/26 | V Girls Volleyball | New Canaan | Home - Main Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/26 | JV Girls Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | L 0-2 | ||
| Fri., 10/26 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/27 | V Boys Cross Country | CIAC Class LL Championships | Away - Wickham Park-Manchester, CT | 10:20 a.m. | ||
| Sat., 10/27 | V Girls Cross Country | CIAC Class LL Championships | Away | 10:50 a.m. | ||
| Sat., 10/27 | FR Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 1:30 p.m. | ||
| Mon., 10/29 | V Girls Swimming and Diving | FCIAC Diving Championship | Home - Westhill Pool [Directions] | 4:30 p.m. | ||
| Tue., 10/30 | FR Football | Trumbull | Home - Rippowam MS - Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 10/30 | V Girls Swimming and Diving | FCIAC Trials | Away - Greenwich HS | TBA | ||
| Tue., 10/30 | V Girls Volleyball | Staples | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Thu., 11/1 | V Girls Swimming and Diving | FCIAC Finals | Away - Greenwich HS | TBA | ||
| Thu., 11/1 | V Girls Volleyball | Darien | Away - Fairfield Ludlowe HS [Directions] | W 3-2 | ||
| Fri., 11/2 | V Boys Cross Country | CIAC Open Championships | Away - Wickham Park-Manchester, CT | 2:00 p.m. | ||
| Fri., 11/2 | V Football | Trumbull | Away - McDougall Stadium [Directions] | L 15-35 | ||
| Fri., 11/2 | V Girls Cross Country | CIAC Open Championships | Away - Wickham Park-Manchester, CT | 2:45 p.m. | ||
| Sat., 11/3 | JV Football | Trumbull | Home - J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 11/3 | V Girls Volleyball | Trumbull | Away - Fairfield Ludlowe HS [Directions] | L 3-0 | ||
| Wed., 11/7 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown HS. | 5:30 p.m. | ||
| Thu., 11/8 | FR Football | Wilton | Away [Directions] | 6:00 p.m. | ||
| Thu., 11/8 | V Girls Volleyball | Hamden | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Sat., 11/10 | V Football | Wilton | Home - J. Walter Kennedy Stadium [Directions] | L 6-13 | ||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class LL Trials | Away - East Hartford HS | 11:30 a.m. | ||
| Sat., 11/10 | V Girls Volleyball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Mon., 11/12 | JV Football | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Wed., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Southern Connecticut State Univ. | 6:00 p.m. | ||
| Wed., 11/14 | V Girls Volleyball | Amity | Away - Fairfield Warde HS [Directions] | 6:00 p.m. | ||
| Thu., 11/15 | V Girls Swimming and Diving | CIAC Open Diving Championships | Away - Middletown HS | 5:30 p.m. | ||
| Sat., 11/17 | JV Football | Stamford | Home - J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 11/17 | FR Football | Stamford | Home - J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Championships | Away - Yale University | 12:00 p.m. | ||
| Wed., 11/21 | V Football | Stamford | Away - Stamford HS [Directions] | L 0-19 | ||
| Sat., 12/1 | V Girls Ice Hockey | HS Girls Hockey Jamboree | Away - The Rinks at Shelton | 5:45 p.m. | ||
| Wed., 12/5 | V Boys Basketball | Hamden (Scrim.) | Away - HHS Gym [Directions] | 3:00 p.m. | ||
| Wed., 12/5 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton - Upper [Directions] | L 2-8 | ||
| Mon., 12/10 | V Boys Basketball | Crosby (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 12/12 | V Boys Basketball | Career Magnet (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 4:15 p.m. | ||
| Wed., 12/12 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | L 7-8 | ||
| Wed., 12/12 | V Wrestling | Darien | Home - Westhill - New Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/12 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 33-60 | ||
| Wed., 12/12 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/12 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | W 5-4 | ||
| Fri., 12/14 | V Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | L 51-56 | ||
| Fri., 12/14 | JV Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | FR Boys Basketball | Joel Barlow | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/14 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | L 22-46 | ||
| Fri., 12/14 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - SoNo Ice House [Directions] | W 4-1 | ||
| Sat., 12/15 | V Boys Indoor Track | Staples | Away - Staples HS Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/15 | V Wrestling | Londonderry Holiday Tourney | Away - Londonderry (NH) HS | TBA | ||
| Sat., 12/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | L 3-9 | 1st -4pm SHS - Exit 18 | |
| Sat., 12/15 | V Girls Indoor Track | Staples | Away - Staples HS Field House [Directions] | 10:00 a.m. | ||
| Tue., 12/18 | V Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | W 64-47 | ||
| Tue., 12/18 | JV Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 12/18 | FR Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 12/19 | V Boys Ice Hockey | West Haven Coop | Away - Bennett Rink [Directions] | L 2-5 | ||
| Wed., 12/19 | V Boys Swimming and Diving | Danbury | Home - Westhill Pool [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | V Wrestling | Norwalk | Home - Westhill - New Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/19 | V Girls Basketball | Harding | Home - Westhill - Main Gymnasium [Directions] | W 34-33 | ||
| Wed., 12/19 | JV Girls Basketball | Harding | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | L 1-6 | Myers -1:45pm WHS -2pm SHS | |
| Fri., 12/21 | V Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | W 68-59 | ||
| Fri., 12/21 | JV Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Bridgeport Central | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/21 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 62-27 | ||
| Fri., 12/21 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:30 p.m. | ||
| Sat., 12/22 | V Boys Ice Hockey | North Haven | Home - Terry Conners Ice Rink [Directions] | W 5-1 | ||
| Sat., 12/22 | V Wrestling | Trumbull, Fairfield Warde, Shelton, New Britain | Away - Auxiliary gym [Directions] | 10:00 a.m. | ||
| Thu., 12/27 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 51-70 | ||
| Thu., 12/27 | V Wrestling | Friar Bash | Away - St. Anthony's HS (NY) | TBA | ||
| Thu., 12/27 | V Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | L 34-46 | ||
| Fri., 12/28 | V Wrestling | Friar Bash | Away - St. Anthony's HS (NY) | TBA | ||
| Sat., 12/29 | V Boys Basketball | Pomperaug | Away - Staples HS-Westport [Directions] | W 58-50 | ||
| Sat., 12/29 | V Boys Ice Hockey | East Haven Coop | Home - Terry Conners Ice Rink [Directions] | L 4-7 | ||
| Sat., 12/29 | V Girls Basketball | Scarsdale (NY) | Away - Stamford HS Gym | L 22-35 | ||
| Thu., 1/3 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | L 45-83 | ||
| Thu., 1/3 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Thu., 1/3 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Thu., 1/3 | V Wrestling | Danbury | Home - Westhill - New Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 1/3 | V Girls Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | L 34-38 | ||
| Thu., 1/3 | JV Girls Basketball | Wilton | Home - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Pat Spinola Natatorium [Directions] | 3:30 p.m. | ||
| Sat., 1/5 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion [Directions] | L 4-6 | ||
| Sat., 1/5 | V Boys Indoor Track | Staples | Away - Staples HS Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/5 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS | TBA | ||
| Sat., 1/5 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | L 3-7 | 1st leave shs 6pm go to exit 18 | |
| Sat., 1/5 | V Girls Indoor Track | Staples | Away - Staples HS Field House [Directions] | 10:00 a.m. | ||
| Mon., 1/7 | V Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | L 44-51 | ||
| Mon., 1/7 | JV Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/7 | FR Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 1/7 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - SoNo Ice House [Directions] | W 7-3 | ||
| Mon., 1/7 | V Girls Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | L 13-86 | ||
| Mon., 1/7 | JV Girls Basketball | Norwalk | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/8 | V Girls Gymnastics | New Canaan, Staples | Home - Westhill - New Gymnasium [Directions] | 106.65 | ||
| Wed., 1/9 | V Boys Swimming and Diving | Darien | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 1/9 | V Wrestling | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 6:30 p.m. | ||
| Wed., 1/9 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 0-8 | Staples Buses | |
| Thu., 1/10 | V Boys Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | L 39-54 | ||
| Thu., 1/10 | JV Boys Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/10 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | W 8-5 | ||
| Thu., 1/10 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 39-51 | ||
| Thu., 1/10 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Sat., 1/12 | V Boys Indoor Track | Staples | Away - Staples HS Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/12 | V Wrestling | Law PanPrez Duals | Away - Jonathan Law HS (Milford, CT) | TBA | ||
| Sat., 1/12 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | W 8-7 | ||
| Sat., 1/12 | V Girls Indoor Track | Staples | Away - Staples HS Field House [Directions] | 10:00 a.m. | ||
| Mon., 1/14 | V Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | L 51-56 | ||
| Mon., 1/14 | JV Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | FR Boys Basketball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 1/14 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 33-60 | ||
| Mon., 1/14 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/14 | V Girls Gymnastics | New Canaan, Fairfield Ludlowe, Fairfield Warde | Away - GCA-Fairfield [Directions] | 112 | ||
| Tue., 1/15 | V Boys Swimming and Diving | Wilton | Away [Directions] | 3:40 p.m. | ||
| Wed., 1/16 | V Boys Ice Hockey | Trinity Catholic | Home - Terry Conners Ice Rink [Directions] | W 8-3 | ||
| Wed., 1/16 | V Wrestling | Staples | Away - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/16 | V Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | L 0-7 | ||
| Thu., 1/17 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | L 44-61 | ||
| Thu., 1/17 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Thu., 1/17 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Thu., 1/17 | V Girls Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | L 33-46 | ||
| Thu., 1/17 | JV Girls Basketball | Trinity Catholic | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/18 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | L 4-5 | Myers 2:15pm shs -westport 4 | |
| Sat., 1/19 | V Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | L 52-68 | ||
| Sat., 1/19 | V Boys Ice Hockey | Amity | Home - Terry Conners Ice Rink [Directions] | W 3-2 | ||
| Sat., 1/19 | V Boys Indoor Track | Wilton | Away - Wilton HS Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/19 | V Wrestling | New Milford Tournament | Away - New Milford HS | TBA | ||
| Sat., 1/19 | V Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | L 17-49 | ||
| Sat., 1/19 | V Girls Gymnastics | New Canaan, Darien | Away - Darien YMCA [Directions] | 102.35 | ||
| Sat., 1/19 | V Girls Indoor Track | Wilton | Away - Wilton HS Field House [Directions] | 9:30 a.m. | ||
| Mon., 1/21 | V Girls Gymnastics | New Canaan, Trumbull, Fairfield Ludlowe, Fairfield Warde | Away - Next Dimension Gymnastics [Directions] | Cancelled | ||
| Mon., 1/21 | V Girls Ice Hockey | Avon | Home - Terry Conners Ice Rink [Directions] | L 3-4 | ||
| Tue., 1/22 | V Boys Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | L 42-60 | ||
| Tue., 1/22 | JV Boys Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/22 | FR Boys Basketball | St. Joseph | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/22 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | L 28-60 | ||
| Tue., 1/22 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Wed., 1/23 | V Boys Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | L 0-8 | ||
| Wed., 1/23 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 4:10 p.m. | ||
| Wed., 1/23 | V Wrestling | Greenwich | Away - GHS Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 1/23 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | L 1-8 | ||
| Fri., 1/25 | V Boys Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | L 52-68 | ||
| Fri., 1/25 | JV Boys Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Boys Basketball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | W 5-0 | ||
| Fri., 1/25 | V Boys Swimming and Diving | Ridgefield | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 39-61 | ||
| Fri., 1/25 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/26 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | L 2-4 | ||
| Sat., 1/26 | V Boys Indoor Track | FCIAC Western Division Championship | Away - Staples HS Field House | 10:00 a.m. | ||
| Sat., 1/26 | V Wrestling | Ridgefield Challenge | Away - Ridgefield HS | TBA | ||
| Sat., 1/26 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | L 1-6 | ||
| Sat., 1/26 | V Girls Indoor Track | FCIAC Western Division Championship | Away - Staples HS Field House | 10:00 a.m. | ||
| Mon., 1/28 | V Girls Gymnastics | New Canaan, Wilton | Home - Westhill - New Gymnasium [Directions] | 109.5 | ||
| Mon., 1/28 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 1-8 | 6:25pm Myers | |
| Tue., 1/29 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 44-64 | ||
| Tue., 1/29 | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/29 | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/29 | V Girls Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | L 42-44 | ||
| Tue., 1/29 | JV Girls Basketball | Staples | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/29 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | L 1-8 | ||
| Thu., 1/31 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Ath. Ctr.-Hillhouse HS (New Haven) | 4:30 p.m. | ||
| Thu., 1/31 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Thu., 1/31 | V Wrestling | Ridgefield | Home - Westhill - New Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 1/31 | V Girls Gymnastics | New Canaan, Greenwich | Away - Greenwich YWCA [Directions] | 114.95 | ||
| Thu., 1/31 | V Girls Ice Hockey | Hall/Conard | Home - Terry Conners Ice Rink [Directions] | L 0-4 | ||
| Thu., 1/31 | V Girls Indoor Track | FCIAC Championships | Away - Floyd Little Ath. Ctr.-Hillhouse HS (New Haven) | 4:30 p.m. | ||
| Fri., 2/1 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | L 55-58 | ||
| Fri., 2/1 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/1 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | New Canaan | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | L 47-54 | ||
| Fri., 2/1 | JV Girls Basketball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 2/2 | V Boys Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | L 2-5 | ||
| Sat., 2/2 | V Wrestling | New Fairfield Duals | Away - New Fairfield HS | TBA | ||
| Sat., 2/2 | V Girls Basketball | Immaculate | Home - Westhill - Main Gymnasium [Directions] | W 51-46 | ||
| Sat., 2/2 | JV Girls Basketball | Immaculate | Home - Westhill - Main Gymnasium [Directions] | 11:30 a.m. | ||
| Mon., 2/4 | V Girls Ice Hockey | Branford | Home - Terry Conners Ice Rink [Directions] | L 3-4 | ||
| Tue., 2/5 | V Boys Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | W 66-59 | ||
| Tue., 2/5 | JV Boys Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Boys Basketball | Brien McMahon | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 45-37 | ||
| Tue., 2/5 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Wed., 2/6 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/6 | V Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | L 0-5 | ||
| Fri., 2/8 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 32-60 | ||
| Fri., 2/8 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Wrestling | FCIAC Tournament | Away - New Canaan HS | TBA | ||
| Fri., 2/8 | V Girls Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | L 45-53 | ||
| Fri., 2/8 | JV Girls Basketball | Fairfield Ludlowe | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | L 6-8 | Parent drop off and pick up | |
| Sat., 2/9 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | L 4-5(OT) | ||
| Sat., 2/9 | V Boys Indoor Track | CIAC Class LL Championship Meet | Away - Floyd Little Center/Hillhouse HS | 4:30 p.m. | ||
| Sat., 2/9 | V Wrestling | FCIAC Championships | Away - New Canaan HS | TBA | ||
| Sat., 2/9 | V Girls Gymnastics | FCIAC Championships | Home - Westhill - Main Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/9 | V Girls Indoor Track | CIAC Class LL Championship Meet | Away - Floyd Little Center/Hillhouse HS | 4:30 p.m. | ||
| Mon., 2/11 | JV Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | ||
| Mon., 2/11 | FR Boys Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | W 5-0 | ||
| Mon., 2/11 | JV Girls Basketball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 0-7 | 1st 5:15 Drop only - Parent pick up | |
| Wed., 2/13 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | L 61-66 | ||
| Wed., 2/13 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/13 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/13 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Terry Conners Ice Rink [Directions] | W 5-4(OT) | ||
| Wed., 2/13 | V Girls Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | L 33-44 | ||
| Wed., 2/13 | JV Girls Basketball | Darien | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/13 | V Girls Gymnastics | Ro Carlucci JV Meet | Home - Westhill - New Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/15 | V Wrestling | CIAC Class LL Tournament | Away - Trumbull HS | TBA | ||
| Fri., 2/15 | V Girls Ice Hockey | Northwest Catholic | Home - Terry Conners Ice Rink [Directions] | W 8-6 | ||
| Sat., 2/16 | V Boys Ice Hockey | St. Joseph | Home - Terry Conners Ice Rink [Directions] | W 9-4 | ||
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship Meet | Away - Floyd Little Center/Hillhouse HS | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS | TBA | ||
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Center/Hillhouse HS | 12:00 p.m. | ||
| Mon., 2/18 | V Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | L 52-77 | ||
| Mon., 2/18 | JV Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/18 | FR Boys Basketball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/18 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 1-7 | ||
| Thu., 2/21 | V Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | L 48-61 | ||
| Thu., 2/21 | JV Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/21 | FR Boys Basketball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/21 | V Boys Ice Hockey | Guilford | Home - Terry Conners Ice Rink [Directions] | W 7-3 | ||
| Thu., 2/21 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 3:30 p.m. | ||
| Fri., 2/22 | V Wrestling | State Open Tournament | Away - Floyd Little Ath. Ctr-Hillhouse HS (New Haven) | TBA | ||
| Sat., 2/23 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Terry Conners Ice Rink [Directions] | W 7-4 | ||
| Sat., 2/23 | V Wrestling | State Open Championships | Away - Floyd Little Ath. Ctr.-Hillhouse HS (New Haven) | TBA | ||
| Tue., 2/26 | V Boys Swimming and Diving | FCIAC Trials | Away - Greenwich HS | 5:30 p.m. | ||
| Wed., 2/27 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 3:30 p.m. | ||
| Wed., 2/27 | V Boys Swimming and Diving | FCIAC Diving Championship | Home - Westhill Pool [Directions] | 5:00 p.m. | ||
| Thu., 2/28 | V Boys Swimming and Diving | FCIAC Championship | Away - Greenwich HS | 6:30 p.m. | ||
| Fri., 3/1 | V Wrestling | N.E. Tournament | Away - TBA | TBA | ||
| Sat., 3/2 | V Wrestling | N.E. Championships | Away - TBA | TBA | ||
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Championship | Away - Middletown HS | 5:30 p.m. | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Trials | Away - East Hartford HS | 6:00 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class LL Championship | Away - Southern CT State University | 1:30 p.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving Championship | Away - Bulkeley HS/Hartford | 5:30 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Championship | Away - Yale University | 7:00 p.m. | ||
| Thu., 3/21 | V Boys Tennis | Hendrick Hudson (Montrose, NY) | Away | 4:00 p.m. | ||
| Fri., 3/22 | V Girls Lacrosse | Foran (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 3/23 | V Baseball | New Canaan (Scrim.) | Home - Westhill Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 3/23 | JV Baseball | New Canaan (Scrim.) | Away - Mead Park [Directions] | 9:00 a.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Jamboree/Bunnell, Stratford, Jonathon Law | Home - J. Walter Kennedy Stadium [Directions] | 9:00 a.m. | ||
| Sat., 3/23 | V Softball | Darien (Scrim.) | Away [Directions] | 10:30 a.m. | ||
| Sun., 3/24 | V Softball | Horace Greeley (NY) (Scrim.) | Home - Westhill Softball Field [Directions] | 11:00 a.m. | ||
| Mon., 3/25 | V Baseball | Briarcliff (NY) (Scrim.) | Away | 3:45 p.m. | ||
| Mon., 3/25 | V Boys Tennis | Amity (Scrim.) | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | King and Low-Heywood Thomas (Scrim.) | Away | 4:00 p.m. | ||
| Wed., 3/27 | V Baseball | Stepinac (NY) (Scrim.) | Away | 3:45 p.m. | ||
| Wed., 3/27 | V Boys Tennis | Weston (Scrim.) | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Tennis | Weston (Scrim.) | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Volleyball | Greenwich (Scrim.) | Home - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | V Girls Lacrosse | Immaculate (Scrim.) | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Baseball | Amity (Scrim.) | Away - John Janenda Baseball Field @ Amity HS [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Boys Tennis | King and Low-Heywood Thomas (Scrim.) | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 3/30 | V Baseball | Weston | Away - Wilton HS Varsity Field [Directions] | W 12-0 | ||
| Sat., 3/30 | JV Baseball | Weston | Away - Wilton HS JV Field [Directions] | 9:30 a.m. | ||
| Sat., 3/30 | V Boys Lacrosse | Immaculate | Away - Mustang Valley [Directions] | L 7-14 | ||
| Sat., 3/30 | V Boys Volleyball | Daniel Hand | Home - Westhill - Main Gymnasium [Directions] | L 0-3 | ||
| Sat., 3/30 | JV Boys Volleyball | Daniel Hand | Home - Westhill - Main Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 3/30 | V Girls Lacrosse | Avon | Home - Westhill Front Turf Field [Directions] | W 6-4 | ||
| Sat., 3/30 | V Softball | Trumbull | Home - Westhill Softball Field [Directions] | L 1-14 | ||
| Sat., 3/30 | V Softball | Norwich Free Academy | Home - West Hill HS [Directions] | L 1-14 | ||
| Sat., 3/30 | JV Softball | Trumbull | Home - Roxbury Elementary School [Directions] | 10:00 a.m. | ||
| Tue., 4/2 | V Boys Lacrosse | Darien | Away - DHS Center Oval Turf Field [Directions] | L 0-12 | ||
| Tue., 4/2 | JV Boys Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Boys Tennis | Bridgeport Central | Home - Westhill Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/2 | V Girls Lacrosse | New Canaan | Home - Westhill Front Turf Field [Directions] | L 0-18 | ||
| Tue., 4/2 | JV Girls Lacrosse | New Canaan | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | V Girls Tennis | Bridgeport Central | Away [Directions] | W 7-0 | ||
| Wed., 4/3 | V Baseball | Immaculate | Home - Westhill Baseball Field [Directions] | W 8-7 | ||
| Wed., 4/3 | JV Baseball | Immaculate | Away - Immaculate HS [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | FR Boys Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Boys Volleyball | Staples | Home - Westhill - Main Gymnasium [Directions] | L 1-3 | ||
| Wed., 4/3 | JV Boys Volleyball | Staples | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 4/4 | V Boys Lacrosse | Greenwich | Home - J. Walter Kennedy Stadium [Directions] | L 3-16 | ||
| Thu., 4/4 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 2-5 | ||
| Thu., 4/4 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | L 0-3 | ||
| Thu., 4/4 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | 4:15 p.m. | ||
| Thu., 4/4 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 10-6 | ||
| Thu., 4/4 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Thu., 4/4 | V Girls Tennis | Wilton | Home [Directions] | L 2-5 | ||
| Fri., 4/5 | JV Boys Lacrosse | Greenwich | Home - J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Fri., 4/5 | V Boys Volleyball | Danbury | Home - Westhill - Main Gymnasium [Directions] | L 0-3 | ||
| Fri., 4/5 | JV Boys Volleyball | Danbury | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 4/5 | FR Girls Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | Cancelled | ||
| Sat., 4/6 | V Baseball | Notre Dame-West Haven | Home - Westhill Baseball Field [Directions] | W 9-0 | ||
| Sat., 4/6 | JV Baseball | Notre Dame-West Haven | Home - Belltown Field [Directions] | 2:00 p.m. | ||
| Sat., 4/6 | FR Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | 2:00 p.m. | ||
| Sat., 4/6 | FR Boys Lacrosse | Brien McMahon | Away - Brien McMahon [Directions] | 1:30 p.m. | ||
| Sat., 4/6 | V Girls Lacrosse | St. Paul Catholic | Home - Westhill Front Turf Field [Directions] | W 16-7 | ||
| Mon., 4/8 | FR Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Boys Golf | New Canaan | Home - E. Gaynor Brennan Golf Course [Directions] | New Canaan. 158 Westhill. 170 | ||
| Mon., 4/8 | FR Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | W 5-2 | ||
| Mon., 4/8 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 0-3 | ||
| Mon., 4/8 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Norwalk | Home [Directions] | W 7-0 | ||
| Tue., 4/9 | V Baseball | Joel Barlow | Home - Westhill Baseball Field [Directions] | W 12-2 | ||
| Tue., 4/9 | FR Boys Lacrosse | Trumbull | Home - J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | Wilton | Home - Westhill Front Turf Field [Directions] | L 4-19 | ||
| Tue., 4/9 | JV Girls Lacrosse | Wilton | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | V Softball | Bassick | Away - Cal Ripkin Field @ longfellow Park [Directions] | W 19-2 | ||
| Wed., 4/10 | V Baseball | Bridgeport Central | Home - Westhill Baseball Field [Directions] | W 6-0 | ||
| Wed., 4/10 | JV Baseball | Bridgeport Central | Home - Belltown Field [Directions] | Cancelled | ||
| Wed., 4/10 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Fairfield Ludlowe. 175 Westhill. 195 | ||
| Wed., 4/10 | V Boys Outdoor Track | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Boys Tennis | Danbury | Home - Westhill Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/10 | V Boys Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | L 0-3 | ||
| Wed., 4/10 | JV Boys Volleyball | New Canaan | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/10 | V Girls Outdoor Track | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | W 17-0 | ||
| Wed., 4/10 | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Tennis | Danbury | Away - WCSU Tennis Courts, Westside Campus [Directions] | W 7-0 | ||
| Thu., 4/11 | V Boys Golf | Norwalk, Stamford | Away - Oak Hills G.C. [Directions] | Westhill. 162 Norwalk. 215 | ||
| Thu., 4/11 | V Boys Lacrosse | Bunnell-Stratford | Home - J. Walter Kennedy Stadium [Directions] | L 7-8 | ||
| Thu., 4/11 | JV Boys Lacrosse | Bunnell-Stratford | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Tennis | Fairfield Warde | Home - Westhill Tennis Courts [Directions] | W 4-3 | ||
| Thu., 4/11 | V Girls Lacrosse | Brien McMahon | Home - Westhill Front Turf Field [Directions] | L 7-12 | ||
| Thu., 4/11 | JV Girls Lacrosse | Brien McMahon | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/11 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | W 6-1 | ||
| Fri., 4/12 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | L 2-3 | ||
| Fri., 4/12 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | FR Baseball | Wilton | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | FR Boys Lacrosse | Stamford | Away - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Fri., 4/12 | V Boys Tennis | Joel Barlow | Home - Westhill Tennis Courts [Directions] | W 5-1 | ||
| Fri., 4/12 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | ||
| Fri., 4/12 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Softball | Wilton | Home - Westhill Softball Field [Directions] | L 2-13 | ||
| Fri., 4/12 | JV Softball | Wright Tech | Away - Scalzi Park Softball Field #3 [Directions] | 3:45 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel HS [Directions] | L 4-14 | ||
| Sat., 4/13 | V Girls Lacrosse | Bethel | Home - Westhill Front Turf Field [Directions] | W 14-10 | ||
| Sat., 4/13 | JV Girls Lacrosse | Bethel | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Sat., 4/13 | FR Girls Lacrosse | Wilton | Home [Directions] | 11:00 a.m. | ||
| Tue., 4/16 | V Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | W 12-7 | ||
| Tue., 4/16 | JV Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | FR Baseball | Norwalk | Home - Westhill Baseball Field [Directions] | 2:00 p.m. | ||
| Tue., 4/16 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | L 4-17 | ||
| Tue., 4/16 | JV Boys Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | L 7-17 | ||
| Tue., 4/16 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | V Softball | Norwalk | Home - Westhill Softball Field [Directions] | L 4-10 | ||
| Tue., 4/16 | JV Softball | Norwalk | Home - Roxbury Elementary School [Directions] | 2:00 p.m. | ||
| Tue., 4/16 | V Girls Tennis | St. Joseph | Away [Directions] | W 6-1 | ||
| Wed., 4/17 | V Baseball | Danbury | Home - Westhill Baseball Field [Directions] | L 6-13 | ||
| Wed., 4/17 | JV Baseball | Danbury | Home - Belltown Field [Directions] | 12:00 p.m. | ||
| Wed., 4/17 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Wed., 4/17 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | L 2-3 | ||
| Wed., 4/17 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 12:00 p.m. | ||
| Thu., 4/18 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 12:00 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Danbury | Home - J. Walter Kennedy Stadium [Directions] | W 8-7 | ||
| Thu., 4/18 | JV Boys Lacrosse | Danbury | Home - J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 4-14 | ||
| Thu., 4/18 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 12:30 p.m. | ||
| Mon., 4/22 | V Boys Golf | Staples | Away - Longshore [Directions] | Staples. 154 Westhill. 178 | ||
| Mon., 4/22 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | V Boys Volleyball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | L 0-3 | ||
| Mon., 4/22 | JV Boys Volleyball | Fairfield Warde | Home - Westhill - Main Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 4/22 | V Girls Outdoor Track | Greenwich, Trumbull | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Baseball | Fairfield Warde | Home - Westhill Baseball Field [Directions] | W 9-8 | ||
| Tue., 4/23 | V Boys Golf | Darien | Away - CC of Darien [Directions] | Darien. 154 Westhill 184 | ||
| Tue., 4/23 | V Boys Outdoor Track | Trumbull, Greenwich | Away - McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 0-7 | ||
| Tue., 4/23 | V Girls Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | L 9-11 | ||
| Tue., 4/23 | JV Girls Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | L 2-6 | ||
| Tue., 4/23 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Staples | Home [Directions] | L 1-6 | ||
| Wed., 4/24 | V Baseball | St. Joseph | Home - Westhill Baseball Field [Directions] | L 2-18 | ||
| Wed., 4/24 | JV Baseball | St. Joseph | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Boys Golf | Danbury | Home - E. Gaynor Brennan Golf Course [Directions] | Danbury. 176 Westhill. 183 | ||
| Wed., 4/24 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | W 6-1 | ||
| Wed., 4/24 | V Boys Tennis | Trumbull | Home - Westhill Tennis Courts [Directions] | W 4-3 | ||
| Wed., 4/24 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 1-3 | ||
| Wed., 4/24 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/24 | FR Girls Lacrosse | Fairfield Warde | Home [Directions] | 5:00 p.m. | ||
| Wed., 4/24 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | L 1-7 | ||
| Wed., 4/24 | JV Softball | St. Joseph | Away - Long Hill Administration field, Trumbull CT [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Trinity Catholic | Home [Directions] | W 7-0 | ||
| Thu., 4/25 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | W 11-0 | ||
| Thu., 4/25 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 0-7 | ||
| Thu., 4/25 | V Girls Lacrosse | St. Joseph | Home - Westhill Front Turf Field [Directions] | L 4-16 | ||
| Thu., 4/25 | JV Girls Lacrosse | St. Joseph | Home - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Softball | Trinity Catholic | Home - Westhill Softball Field [Directions] | W 13-5 | ||
| Thu., 4/25 | V Girls Tennis | Greenwich | Home [Directions] | W 4-3 | ||
| Fri., 4/26 | V Boys Lacrosse | Stamford | Home - J. Walter Kennedy Stadium [Directions] | L 11-3 | ||
| Fri., 4/26 | V Boys Volleyball | Stamford | Home - Westhill - Main Gymnasium [Directions] | W 3-0 | ||
| Fri., 4/26 | JV Boys Volleyball | Stamford | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 4/27 | V Baseball | Trumbull | Home - Westhill Baseball Field [Directions] | L 9-15 | ||
| Sat., 4/27 | JV Baseball | Trumbull | Home - Westhill Baseball Field [Directions] | 4:15 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Stamford | Home - J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | FR Boys Lacrosse | New Fairfield | Away [Directions] | Cancelled | ||
| Sat., 4/27 | V Boys Tennis | St. Joseph | Home - Westhill Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/27 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | L 2-3 | ||
| Sat., 4/27 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | Cancelled | ||
| Sat., 4/27 | FR Girls Lacrosse | New Fairfield | Home [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 0-5 | ||
| Sat., 4/27 | JV Softball | Brien McMahon | Home - TBA [Directions] | Cancelled | ||
| Sat., 4/27 | JV Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | V Baseball | Staples | Away - Staples HS Baseball Field [Directions] | W 7-2 | ||
| Mon., 4/29 | JV Baseball | Staples | Away - Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Baseball | Staples | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | L 11-6 | ||
| Mon., 4/29 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Brien McMahon | Home - Westhill Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/29 | V Boys Volleyball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | L 0-3 | ||
| Mon., 4/29 | JV Boys Volleyball | Greenwich | Home - Westhill - Main Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Danbury, Staples | Away - Staples HS [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Staples | Home - Westhill Softball Field [Directions] | L 6-13 | ||
| Mon., 4/29 | JV Softball | Staples | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | ||
| Tue., 4/30 | V Boys Golf | Stamford, Greenwich | Home - E. Gaynor Brennan Golf Course [Directions] | Greenwich. 156 Westhill. 166 | ||
| Tue., 4/30 | V Boys Outdoor Track | Staples, Danbury | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | W 4-3 | ||
| Tue., 4/30 | V Girls Lacrosse | Greenwich | Home - J. Walter Kennedy Stadium [Directions] | L 2-19 | ||
| Tue., 4/30 | JV Girls Lacrosse | Greenwich | Home - J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Fairfield Ludlowe | Home [Directions] | L 3-4 | ||
| Wed., 5/1 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | W 7-3 | ||
| Wed., 5/1 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Greenwich | Home - Westhill Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | V Boys Golf | Fairfield Warde | Home - E. Gaynor Brennan Golf Course [Directions] | Fairfield Warde. 161 Westhill. 172 | ||
| Wed., 5/1 | V Softball | Greenwich | Home - Westhill Softball Field [Directions] | L 2-25 | ||
| Wed., 5/1 | JV Softball | Greenwich | Home - Roxbury Elementary School [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 5/2 | V Baseball | Brien McMahon | Home - Westhill Baseball Field [Directions] | L 1-4 | ||
| Thu., 5/2 | V Boys Golf | Trinity Catholic, Stamford | Home - Woodway Country Club [Directions] | Westhill. 176 Stamford. 209 Trinity. 248 | ||
| Thu., 5/2 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 1-19 | ||
| Thu., 5/2 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Stamford | Away - SHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/2 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-2 | ||
| Thu., 5/2 | V Girls Tennis | Stamford | Home - Westhill Tennis Courts [Directions] | W 6-1 | ||
| Fri., 5/3 | FR Baseball | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Stamford | Home - J. Walter Kennedy Stadium [Directions] | 3:30 p.m. | ||
| Fri., 5/3 | V Boys Outdoor Track | Amity Spartan Midnight Invite | Away - Amity HS-Woodbridge, CT | 4:30 p.m. | ||
| Fri., 5/3 | V Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 1-3 | ||
| Fri., 5/3 | JV Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | V Girls Outdoor Track | Amity Spartan Midnight Invite | Away - Amity HS-Woodbridge, CT | 4:30 p.m. | ||
| Sat., 5/4 | V Boys Lacrosse | Stratford | Away - Penders Field [Directions] | W 11-7 | ||
| Sat., 5/4 | JV Boys Lacrosse | Trinity Catholic | Home - J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | FR Boys Lacrosse | New Fairfield | Home - J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | FR Girls Lacrosse | New Fairfield | Away [Directions] | 11:00 a.m. | ||
| Mon., 5/6 | V Boys Outdoor Track | Ridgefield, Bridgeport Central | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 1-6 | ||
| Mon., 5/6 | V Boys Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | L 0-3 | ||
| Mon., 5/6 | JV Boys Volleyball | Ridgefield | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | FR Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Ridgefield, Bridgeport Central | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Fairfield Ludlowe | Home - Westhill Softball Field [Directions] | L 15-2 | ||
| Mon., 5/6 | JV Softball | Fairfield Ludlowe | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Darien | Home [Directions] | L 2-5 | ||
| Tue., 5/7 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | L 4-14 | ||
| Tue., 5/7 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | FR Baseball | Fairfield Ludlowe | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Golf | St. Joseph | Home - E. Gaynor Brennan Golf Course [Directions] | Westhill. 175 St. Joseph. 188 | ||
| Tue., 5/7 | V Boys Lacrosse | Staples | Home - J. Walter Kennedy Stadium [Directions] | L 22-1 | ||
| Tue., 5/7 | JV Boys Lacrosse | Staples | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Ridgefield | Home - Westhill Tennis Courts [Directions] | L 3-4 | ||
| Tue., 5/7 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 4-3 | ||
| Wed., 5/8 | V Baseball | Stamford | Away - Cubeta Stadium [Directions] | W 6-0 | ||
| Wed., 5/8 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Baseball | Stamford | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Boys Golf | Wilton | Home - E. Gaynor Brennan Golf Course [Directions] | Wilton. 167 Westhill. 163 | ||
| Wed., 5/8 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 0-3 | ||
| Wed., 5/8 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | FR Girls Lacrosse | Staples | Home - Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Softball | Stamford | Home - Westhill Softball Field [Directions] | L 4-6 | ||
| Wed., 5/8 | JV Softball | Stamford | Home - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Golf | Ridgefield | Home - E. Gaynor Brennan Golf Course [Directions] | Westhill. 163 Ridgefield 163 | ||
| Thu., 5/9 | V Boys Lacrosse | New Canaan | Home - J. Walter Kennedy Stadium [Directions] | L 2-16 | ||
| Thu., 5/9 | JV Boys Lacrosse | New Canaan | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | New Canaan | Home - Westhill Tennis Courts [Directions] | L 1-6 | ||
| Thu., 5/9 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 4-19 | ||
| Thu., 5/9 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | Cancelled | ||
| Thu., 5/9 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | L 3-4 | ||
| Fri., 5/10 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | L 3-5 | ||
| Fri., 5/10 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Baseball | Darien | Home - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | L 0-3 | ||
| Fri., 5/10 | JV Boys Volleyball | Trumbull | Home - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Girls Lacrosse | Trumbull | Home - Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 5/10 | V Softball | Darien | Home - Westhill Softball Field [Directions] | W 71 | ||
| Fri., 5/10 | JV Softball | Wright Tech | Home [Directions] | 3:45 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | West Haven | Home - J. Walter Kennedy Stadium [Directions] | W 7-6 | ||
| Sat., 5/11 | JV Boys Lacrosse | West Haven | Home - Westhill Front Turf Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | V Girls Lacrosse | Newington | Home - J. Walter Kennedy Stadium [Directions] | W 15-8 | ||
| Sat., 5/11 | JV Girls Lacrosse | Newington | Home - Westhill Front Turf Field [Directions] | 1:30 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | Stamford | Away - Boyle Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | W 3-2 | ||
| Mon., 5/13 | JV Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:30 p.m. | ||
| Mon., 5/13 | FR Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | L 4-12 | ||
| Tue., 5/14 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | ||
| Tue., 5/14 | V Boys Outdoor Track | Stamford | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | L 8-9 | ||
| Tue., 5/14 | JV Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Outdoor Track | Stamford | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Softball | Ridgefield | Away - Tiger Ridge Softball Field (RHS) [Directions] | L 3-15 | ||
| Tue., 5/14 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Baseball | New Canaan | Home - Stamford HS [Directions] | W 6-0 | ||
| Wed., 5/15 | JV Baseball | New Canaan | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Baseball | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Golf | Stamford, Brien McMahon | Home - E. Gaynor Brennan Golf Course [Directions] | Westhill. 159 McMahon. 216 | ||
| Wed., 5/15 | FR Boys Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 0-3 | ||
| Wed., 5/15 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Girls Outdoor Track | Stamford | Away [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | W 4-2 | ||
| Thu., 5/16 | V Baseball | Ridgefield | Home - Westhill Baseball Field [Directions] | L 2-6 | ||
| Thu., 5/16 | JV Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | FR Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Golf | Trumbull | Home - E. Gaynor Brennan Golf Course [Directions] | Trumbull. 163 Westhill. 166 | ||
| Thu., 5/16 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | L 19-3 | ||
| Thu., 5/16 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 6:00 p.m. | ||
| Thu., 5/16 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 0-3 | ||
| Thu., 5/16 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Lacrosse | Jonathan Law | Home - J. Walter Kennedy Stadium [Directions] | W 13-7 | ||
| Thu., 5/16 | JV Girls Lacrosse | Jonathan Law | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | FR Boys Lacrosse | Norwalk | Home - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Sun., 5/19 | V Softball | Notre Dame-Fairfield | Home - Westhill Softball Field [Directions] | L 0-3 | ||
| Mon., 5/20 | V Boys Volleyball | Kolbe Cathedral | Home - Westhill - Main Gymnasium [Directions] | L 1-3 | ||
| Mon., 5/20 | JV Boys Volleyball | Kolbe Cathedral | Home - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 5/28 | V Baseball | Wilbur Cross | Away - Rice Field-New Haven, CT [Directions] | 3:30 p.m. | ||