| Wilton 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 807 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | TBA | ||
| TBA | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | TBA | Cancelled | |
| TBA | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | ||
| TBA | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 5:00 p.m. | ||
| TBA | JV Boys Ice Hockey | JBWA | Away - Wonderland of Ice - Bridgeport [Directions] | TBA | Wonderland of Ice in Bridgeport | |
| TBA | FR Boys Lacrosse | Fairfield Ludlowe | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| TBA | FR Boys Lacrosse | New Canaan | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| TBA | FR Boys Lacrosse | Greenwich | Home - Allen's Field #2 [Directions] | TBA | ||
| TBA | JV Girls Basketball | Westhill | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Basketball | Greenwich | Home - Wilton Field House [Directions] | TBA | Cancelled | |
| TBA | FR Girls Basketball | Greenwich | Home - Wilton Field House [Directions] | TBA | ||
| TBA | FR Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | TBA | ||
| TBA | JV Girls Lacrosse | Ridgefield | Home - Lilly Field - Turf [Directions] | TBA | ||
| TBA | FR Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| TBA | FR Girls Lacrosse | Fairfield Warde | Home - Allen's Field #2 [Directions] | TBA | ||
| TBA | JV Girls Tennis | Harding | Away [Directions] | 04:30 p.m. | @ Glenwood Park | |
| TBA | JV Girls Tennis | New Canaan | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Tue., 8/27 | V Boys Soccer | Brunswick School (Scrim.) | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 8/27 | JV Boys Soccer | Brunswick School (Scrim.) | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | V Football | Weston (Scrim.) | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 8/29 | V Boys Soccer | South Windsor (Scrim.) | Home - Lilly Field - Turf [Directions] | 5:00 p.m. | ||
| Fri., 8/30 | FR Football | Bethel (Scrim.) | Away - Rockwell Field [Directions] | 4:00 p.m. | ||
| Fri., 8/30 | V Field Hockey | Lakeland/Panas (NY) (Scrim.) | Away | 4:30 p.m. | ||
| Fri., 8/30 | JV Field Hockey | Lakeland/Panas (NY) (Scrim.) | Away | 6:00 p.m. | ||
| Fri., 8/30 | V Girls Volleyball | Westhill (Scrim.) | Home - Wilton Field House [Directions] | 4:15 p.m. | ||
| Sat., 8/31 | V Football | Jamboree | Home - Fujitani Field - Turf [Directions] | 9:00 a.m. | Jamboree 10-Teams | |
| Sat., 8/31 | V Boys Soccer | Guilford (Scrim.) | Away - Bittner Park - Guilford [Directions] | 10:00 a.m. | ||
| Sat., 8/31 | V Field Hockey | Immaculate (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 8/31 | V Girls Soccer | Bethel Jamboree | Away [Directions] | 8:00 a.m. | ||
| Sat., 8/31 | JV Girls Soccer | Bethel Jamboree | Away [Directions] | 8:00 a.m. | ||
| Mon., 9/2 | V Field Hockey | Mamaroneck (NY) (Scrim.) | Away | 9:00 a.m. | ||
| Tue., 9/3 | V Boys Soccer | Joel Barlow (Scrim.) | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | ||
| Tue., 9/3 | V Field Hockey | Greenwich Academy (Scrim.) | Away | 4:30 p.m. | ||
| Tue., 9/3 | JV Field Hockey | Greenwich Academy (Scrim.) | Away | 4:30 p.m. | ||
| Tue., 9/3 | JV Field Hockey | Greenwich Academy (Scrim.) | Away | 4:30 p.m. | ||
| Tue., 9/3 | V Girls Soccer | Brookfield (Scrim.) | Home - Lilly Field-Turf Field [Directions] | 4:15 p.m. | ||
| Tue., 9/3 | JV Girls Soccer | Brookfield (Scrim.) | Home - Lilly Field-Turf Field [Directions] | 4:15 p.m. | ||
| Wed., 9/4 | V Football | Naugatuck (Scrim.) | Home - Fujitani Field - Turf [Directions] | 3:30 p.m. | ||
| Fri., 9/6 | JV Field Hockey | New Fairfield (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Sat., 9/7 | V Field Hockey | New Fairfield (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Girls Volleyball | Val Dickinson Memorial Jamboree | Away [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | JV Girls Volleyball | Val Dickinson Memorial Jamboree | Away [Directions] | 9:00 a.m. | ||
| Tue., 9/10 | V Boys Cross Country | St. Joseph, Fairfield Ludlowe, Fairfield Warde | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Brien McMahon | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 9/10 | JV Boys Soccer | Brien McMahon | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | St. Joseph, Fairfield Ludlowe, Fairfield Warde | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Field Hockey | Pomperaug | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 9/10 | JV Field Hockey | Pomperaug | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Tue., 9/10 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Wilton YMCA [Directions] | 3:40 p.m. | Won: 97-89 | |
| Tue., 9/10 | FR Girls Volleyball | Ridgefield | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Wed., 9/11 | FR Football | Ridgefield (Scrim.) | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Wed., 9/11 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 5-0 | |
| Wed., 9/11 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 9-1 | |
| Thu., 9/12 | V Football | Guilford | Away - Kavanaugh Turf Field at GHS [Directions] | 5:00 p.m. | W 21-20 | |
| Thu., 9/12 | V Boys Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 4:15 p.m. | W 4-1 | |
| Thu., 9/12 | JV Boys Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:15 p.m. | ||
| Thu., 9/12 | V Girls Soccer | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 9/12 | JV Girls Soccer | Fairfield Ludlowe | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University- Rec Plex Pool [Directions] | 3:30 p.m. | Won: 104-81 | |
| Thu., 9/12 | V Girls Volleyball | Trumbull | Home - Wilton Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/12 | JV Girls Volleyball | Trumbull | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/13 | JV Football | Guilford | Away - Kavanaugh Turf Field at GHS [Directions] | 3:30 p.m. | ||
| Fri., 9/13 | FR Boys Soccer | Danbury | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | Loss: 77-109 | |
| Mon., 9/16 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 9/16 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 9/16 | FR Girls Volleyball | Darien | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Boys Cross Country | New Canaan, Staples, Brien McMahon, Bassick, Trinity Catholic | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | New Canaan, Staples, Brien McMahon, Bassick, Trinity Catholic | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Field Hockey | Danbury | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 9/17 | JV Field Hockey | Danbury | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| Tue., 9/17 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:30 p.m. | L 1-3 | |
| Tue., 9/17 | JV Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:30 p.m. | ||
| Tue., 9/17 | FR Girls Soccer | Darien | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Swimming and Diving | Trumbull | Home - New Canaan YMCA [Directions] | 3:30 p.m. | Diving Only | |
| Wed., 9/18 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 5:00 p.m. | L 0-5 | |
| Wed., 9/18 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Wed., 9/18 | FR Boys Soccer | Greenwich | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | FR Field Hockey | Fairfield Ludlowe | Home - Wilton High School - Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Girls Swimming and Diving | Trumbull | Home - Wilton YMCA [Directions] | 3:40 p.m. | Won: 99-87 | |
| Wed., 9/18 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | L 0-5 | |
| Wed., 9/18 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Thu., 9/19 | FR Football | Staples | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Football | Staples | Away - Staples Stadium [Directions] | 7:00 p.m. | L 7-14 | |
| Fri., 9/20 | V Boys Soccer | Bridgeport Central | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/20 | JV Boys Soccer | Bridgeport Central | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | FR Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | FR Field Hockey | Trumbull | Home - Wilton High School - Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | FR Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 5:00 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Fairfield Ludlowe | Home - Wilton Field House [Directions] | 5:30 p.m. | L 1-3 | |
| Fri., 9/20 | JV Girls Volleyball | Fairfield Ludlowe | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | FR Girls Volleyball | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | V Girls Soccer | Westhill | Home - Lilly Field - Turf [Directions] | 4:00 p.m.. | L 0-1 | |
| Sat., 9/21 | JV Girls Soccer | Westhill | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | JV Football | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 9/23 | V Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 4:15 p.m. | W 3-1 | |
| Mon., 9/23 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:30 p.m. | ||
| Mon., 9/23 | FR Boys Soccer | New Canaan | Home [Directions] | 4:15 p.m. | ||
| Mon., 9/23 | V Field Hockey | Westhill | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 9/23 | JV Field Hockey | Westhill | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| Mon., 9/23 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | Loss: 72-106 | |
| Mon., 9/23 | V Girls Volleyball | St. Joseph | Home - Wilton Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/23 | JV Girls Volleyball | St. Joseph | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Trumbull, Danbury, Stamford, Harding | Away - XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Trumbull, Danbury, Stamford, Harding | Away - XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | T 2-2 | |
| Tue., 9/24 | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Boys Soccer | Staples | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | L 0-1 | |
| Wed., 9/25 | JV Boys Soccer | Staples | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | FR Boys Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 9/25 | JV Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 6:00 p.m. | ||
| Wed., 9/25 | FR Girls Volleyball | Stamford | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | FR Football | Branford | Away - Branford High School-Turf Field [Directions] | 7:00 p.m. | ||
| Thu., 9/26 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 9/26 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 9/26 | V Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:30 p.m. | T 1-1 | |
| Thu., 9/26 | JV Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 9/26 | FR Girls Soccer | Trumbull | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Boys Soccer | Bassick | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 9/27 | FR Field Hockey | Darien | Home - Wilton High School - Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 9/27 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/28 | V Boys Cross Country | Wilton Invitational | Home [Directions] | 9:30 a.m. | ||
| Sat., 9/28 | V Football | Branford | Home - Fujitani Field - Turf [Directions] | 2:30 p.m. | W 35-0 | |
| Sat., 9/28 | V Girls Cross Country | Wilton Invitational | Home [Directions] | 9:30 a.m. | ||
| Sat., 9/28 | V Field Hockey | North Haven | Away - North Haven Athletic Complex [Directions] | 10:00 a.m. | W 7-0 | |
| Sat., 9/28 | JV Field Hockey | North Haven | Away - North Haven Athletic Complex - Brook Field [Directions] | 11:30 a.m. | ||
| Mon., 9/30 | V Girls Soccer | Staples | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 9/30 | JV Girls Soccer | Staples | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | FR Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | V Girls Swimming and Diving | St. Joseph | Away - Hillcrest MS, Trumbull, CT [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | V Girls Volleyball | Norwalk | Home - Wilton Field House [Directions] | 5:30 p.m. | L 1-3 | |
| Mon., 9/30 | JV Girls Volleyball | Norwalk | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Westhill, Ridgefield, Bridgeport Central | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Soccer | Ridgefield | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 10/1 | JV Boys Soccer | Ridgefield | Home - Allen's Field #1 [Directions] | 4:15 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Westhill, Ridgefield, Bridgeport Central | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 10/1 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Tue., 10/1 | V Girls Swimming and Diving | New Canaan | Home - New Canaan YMCA [Directions] | 3:30 p.m. | Diving Only | |
| Wed., 10/2 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:15 p.m. | ||
| Wed., 10/2 | V Field Hockey | Trumbull | Away - Indian Ledge Park [Directions] | 4:30 p.m. | W 6-0 | |
| Wed., 10/2 | JV Field Hockey | Trumbull | Away - Indian Ledge Park [Directions] | 5:30 p.m. | ||
| Wed., 10/2 | V Girls Soccer | New Canaan | Home - Lilly Field- Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/2 | JV Girls Soccer | New Canaan | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | FR Girls Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Girls Swimming and Diving | New Canaan | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 10/2 | V Girls Volleyball | Harding | Home [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/2 | JV Girls Volleyball | Harding | Home [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Football | Bassick | Away [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 10/3 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:15 p.m. | W 3-1 | |
| Thu., 10/3 | JV Boys Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:15 p.m. | ||
| Thu., 10/3 | FR Boys Soccer | Fairfield Ludlowe | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Field Hockey | Ridgefield | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/3 | JV Field Hockey | Ridgefield | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Girls Swimming and Diving | Ridgefield | Home - New Canaan YMCA [Directions] | 3:30 p.m. | Diving Only | |
| Fri., 10/4 | V Football | Bassick | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | W 38-14 | |
| Fri., 10/4 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | W 2-1 | |
| Fri., 10/4 | JV Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Fri., 10/4 | FR Girls Soccer | Ridgefield | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Girls Swimming and Diving | Ridgefield | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Fri., 10/4 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:15 p.m. | L 1-3 | |
| Fri., 10/4 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:45 p.m. | ||
| Fri., 10/4 | FR Girls Volleyball | New Canaan | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | JV Football | Bassick | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | Cancelled | |
| Mon., 10/7 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/7 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | FR Girls Volleyball | Greenwich | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Greenwich, Darien, Norwalk | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 3:00 p.m. | T 1-1 | |
| Tue., 10/8 | JV Boys Soccer | Norwalk | Away - Nathan Hale Middle School [Directions] | 3:00 p.m. | ||
| Tue., 10/8 | FR Boys Soccer | Norwalk | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | Greenwich, Darien, Norwalk | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/8 | JV Field Hockey | Norwalk | Away - NHS Grass Field [Directions] | 5:30 p.m. | ||
| Tue., 10/8 | FR Field Hockey | Norwalk | Home - Wilton High School - Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Soccer | Danbury | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/8 | JV Girls Soccer | Danbury | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | V Boys Soccer | Darien | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | T 1-1 | |
| Wed., 10/9 | JV Boys Soccer | Darien | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | FR Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | FR Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/9 | V Girls Volleyball | Fairfield Warde | Home - Wilton Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/9 | JV Girls Volleyball | Fairfield Warde | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Wed., 10/9 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | FR Football | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | V Field Hockey | Stamford | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 10/10 | JV Field Hockey | Stamford | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| Thu., 10/10 | V Girls Soccer | Brien McMahon | Home - Lilly Field-Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 10/10 | JV Girls Soccer | Brien McMahon | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Football | St. Joseph | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 20-44 | |
| Fri., 10/11 | V Boys Soccer | Trinity Catholic | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/11 | V Girls Volleyball | Westhill | Home - Wilton Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/11 | JV Girls Volleyball | Westhill | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | FR Girls Volleyball | Westhill | Away [Directions] | 4:00 p.m. | ||
| Sat., 10/12 | V Field Hockey | South Windsor | Away - South Windsor H.S. [Directions] | 11:00 a.m.. | W 4-0 | |
| Sat., 10/12 | JV Field Hockey | South Windsor | Away - South Windsor H.S. [Directions] | 12:30 p.m. | ||
| Mon., 10/14 | JV Football | St. Joseph | Away - St. Joseph High School [Directions] | 1:00 p.m. | ||
| Tue., 10/15 | V Boys Soccer | New Canaan | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 10/15 | JV Boys Soccer | New Canaan | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | FR Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Field Hockey | Staples | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | W 2-0 | |
| Tue., 10/15 | JV Field Hockey | Staples | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | FR Field Hockey | Staples | Away - Staples Stadium [Directions] | 6:15 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 10/15 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Tue., 10/15 | FR Girls Volleyball | Staples | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Soccer | Greenwich | Home - Lilly Field- Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/16 | JV Girls Soccer | Greenwich | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | FR Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 10/16 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 10/16 | V Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/16 | JV Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:30 p.m. | ||
| Wed., 10/16 | FR Girls Volleyball | Danbury | Home - Cider Mill School [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Boys Cross Country | FCIAC Championship | Away | 2:00 p.m. | ||
| Thu., 10/17 | FR Football | Fairfield Warde | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:15 p.m. | T 1-1 | |
| Thu., 10/17 | JV Boys Soccer | Westhill | Away - Rippowam Middle School [Directions] | 4:15 p.m. | ||
| Thu., 10/17 | FR Boys Soccer | Westhill | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Girls Cross Country | FCIAC Championship | Away | 2:00 p.m. | Waveny Park, New Canaan | |
| Thu., 10/17 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 10/17 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/17 | FR Field Hockey | Greenwich | Home - Wilton High School - Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | FR Girls Soccer | Fairfield Warde | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | L 21-35 | |
| Fri., 10/18 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Girls Volleyball | Brien McMahon | Home - Wilton Field House [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/18 | JV Girls Volleyball | Brien McMahon | Home - Wilton Field House [Directions] | 4:30 p.m. | ||
| Sat., 10/19 | JV Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 10:00 a.m. | Cancelled | |
| Sat., 10/19 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 2:30 p.m. | W 1-0 | |
| Mon., 10/21 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | W 3-2 | |
| Mon., 10/21 | JV Boys Soccer | Trumbull | Away - Varsity Grass Soccer Field [Directions] | 5:30 p.m. | ||
| Mon., 10/21 | FR Boys Soccer | Trumbull | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Field Hockey | New Canaan | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 1-0 | Senior Night |
| Mon., 10/21 | JV Field Hockey | New Canaan | Home - Fujitani Field - Turf [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | FR Field Hockey | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Trinity Catholic | Home - Wilton High School [Directions] | 4:00 p.m. | W 8-1 | |
| Mon., 10/21 | V Girls Volleyball | Bassick | Home [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/21 | JV Girls Volleyball | Bassick | Home [Directions] | 4:30 p.m. | ||
| Tue., 10/22 | FR Field Hockey | Danbury | Away - Danbury High School Grass Field [Directions] | 4:15 p.m. | ||
| Tue., 10/22 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | W 7-0 | |
| Wed., 10/23 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | L 0-4 | |
| Wed., 10/23 | FR Boys Soccer | Fairfield Warde | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/23 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/24 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:15 p.m. | ||
| Thu., 10/24 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 7-1 | |
| Thu., 10/24 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Stamford | Home - Lilly Field - Turf [Directions] | 7:00 p.m. | W 7-0 | Senior Night |
| Thu., 10/24 | JV Girls Soccer | Stamford | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Football | Trumbull | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 28-32 | |
| Fri., 10/25 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | CIAC Class L Championship | Away | 2:05 p.m. | Wickham Park | |
| Sat., 10/26 | FR Football | Trumbull | Away - McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/26 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 12:00 p.m. | W 2-0 | |
| Sat., 10/26 | V Girls Cross Country | Class L Championship | Away | 2:35 p.m. | Wickham Park | |
| Sat., 10/26 | V Field Hockey | Fairfield Ludlowe | Home - Fujitani Field - Turf [Directions] | 3:30 p.m. | W 7-0 | |
| Sat., 10/26 | V Girls Soccer | Fairfield Warde | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/26 | V Girls Soccer | Fairfield Warde | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/28 | JV Football | Trumbull | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Mon., 10/28 | V Boys Soccer | Greenwich | Away [Directions] | 7:00 p.m. | L 5-2 | |
| Mon., 10/28 | V Girls Soccer | Westhill | Home - Norwalk HS [Directions] | 5:00 p.m. | W 2-0 | |
| Mon., 10/28 | V Girls Swimming and Diving | FCIAC Swim Trials | Away [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | V Field Hockey | Fairfield Warde | Home - Brien McMahon HS [Directions] | 5:00 p.m. | ||
| Tue., 10/29 | V Girls Swimming and Diving | FCIAC Diving Finals | Away [Directions] | 4:30 p.m. | ||
| Wed., 10/30 | V Girls Soccer | St. Joseph | Away [Directions] | 4:30 p.m. | ||
| Wed., 10/30 | V Girls Swimming and Diving | FCIAC Swimming Finals | Away [Directions] | 4:00 p.m. | ||
| Thu., 10/31 | FR Football | Darien | Home - Fujitani Field - Turf [Directions] | 5:00 p.m. | ||
| Fri., 11/1 | V Boys Cross Country | CIAC Open Championship | Away | 2:00 p.m. | Wickham Park | |
| Fri., 11/1 | V Girls Cross Country | CIAC Open Championship | Away | 2:45 p.m. | ||
| Sat., 11/2 | V Football | Darien | Away - DHS Stadium Field [Directions] | 1:30 p.m. | L 14-40 | |
| Mon., 11/4 | JV Football | Darien | Away - DHS Stadium Field [Directions] | 3:00 p.m. | ||
| Thu., 11/7 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Fri., 11/8 | V Football | New Canaan | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 7-35 | |
| Sat., 11/9 | V Boys Cross Country | New England Championship | Away | TBA | Derry Park, Manchester,NH | |
| Sat., 11/9 | V Girls Cross Country | New England Championship | Away | TBA | Derry Park, Manchester,NH | |
| Mon., 11/11 | JV Football | New Canaan | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 11/14 | FR Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Fri., 11/15 | V Football | Ridgefield | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | L 13-21 | |
| Mon., 11/18 | JV Football | Trinity Catholic | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 11/21 | FR Football | Trinity Catholic | Home - Fujitani Field- Turf [Directions] | 4:00 p.m. | ||
| Sat., 11/23 | JV Football | Ridgefield | Home - Fujitani Field - Turf [Directions] | 10:00 a.m. | Cancelled | |
| Thu., 11/28 | V Football | Trinity Catholic | Away - Trinity Catholic Alumni Field | 10:00 a.m. | W 26-7 | |
| Mon., 12/2 | V Girls Basketball | Newtown (Scrim.) | Home - Wilton Field House [Directions] | 6:00 p.m. | ||
| Sat., 12/7 | V Boys Basketball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 2:00 p.m. | ||
| Sat., 12/7 | V Boys Ice Hockey | Cheshire (Scrim.) | Away - Wesleyan University Ice Rink [Directions] | 11:15 a.m. | ||
| Sat., 12/7 | V Wrestling | Ridgefield (Scrim.) | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 8:30 a.m. | ||
| Sat., 12/7 | V Girls Basketball | Joel Barlow (Scrim.) | Home - Wilton High School Field House [Directions] | 9:30 a.m. | ||
| Sat., 12/7 | V Girls Ice Hockey | Girls HS Jamboree | Away | TBA | Rinks @ Shelton | |
| Mon., 12/9 | V Girls Basketball | New Fairfield (Scrim.) | Away [Directions] | 4:15 p.m. | ||
| Wed., 12/11 | V Boys Basketball | Derby (Scrim.) | Home - Wilton Field House [Directions] | 4:30 p.m. | ||
| Wed., 12/11 | V Boys Ice Hockey | Amity (Scrim.) | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | ||
| Wed., 12/11 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | W 48-39 | |
| Wed., 12/11 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/11 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - SoNo Ice House [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 12/12 | V Boys Basketball | New Fairfield (Scrim.) | Home - Wilton High School Field House [Directions] | 5:30 p.m. | ||
| Fri., 12/13 | V Boys Basketball | Joel Barlow (Scrim.) | Home - Wilton Field House [Directions] | 4:30 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 7:00 p.m. | W 48-43 | |
| Fri., 12/13 | JV Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:15 p.m. | ||
| Fri., 12/13 | FR Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:15 p.m. | ||
| Mon., 12/16 | V Girls Ice Hockey | Hall/Conard | Away [Directions] | 7:00 p.m. | L 5-3 | West Hartford |
| Wed., 12/18 | V Boys Basketball | Darien | Home - Wilton Field House [Directions] | 7:00 p.m. | W 58-42 | |
| Wed., 12/18 | JV Boys Basketball | Darien | Home - Wilton Field House [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Boys Basketball | Darien | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home [Directions] | 3:40 p.m. | ||
| Wed., 12/18 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | W 46-40 | |
| Wed., 12/18 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | V Girls Ice Hockey | Fairfield Warde | Home - SoNo Ice House [Directions] | 5:50 p.m. | W 2-0 | |
| Thu., 12/19 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks [Directions] | 3:30 p.m. | L 2-3(OT) | |
| Thu., 12/19 | V Wrestling | Westhill | Home - Wilton Field House [Directions] | 6:00 p.m. | ||
| Fri., 12/20 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | L 60-65 | |
| Fri., 12/20 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Girls Basketball | New Canaan | Home - Wilton Field House [Directions] | 7:00 p.m. | W 49-32 | |
| Fri., 12/20 | JV Girls Basketball | New Canaan | Home - Wilton Field House [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Girls Basketball | New Canaan | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Sat., 12/21 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | 4:00 p.m. | T 3-3 | |
| Sat., 12/21 | V Boys Indoor Track | Danbury, Ridgefield, Trumbull, New Canaan | Home - Wilton Field House [Directions] | 9:30 a.m. | Westhill, Norwalk | |
| Sat., 12/21 | V Wrestling | Guilford Tournament | Away | 9:00 a.m. | ||
| Sat., 12/21 | JV Wrestling | Trumbull | Away [Directions] | 9:00 a.m. | ||
| Sat., 12/21 | V Girls Ice Hockey | Hamden Coop | Home - SoNo Ice House [Directions] | 12:00 p.m. | L 0-6 | |
| Sat., 12/21 | V Girls Indoor Track | Danbury, Ridgefield, Trumbull, New Canaan | Home - Wilton Field House [Directions] | 9:30 a.m. | Westhill, Norwalk | |
| Sun., 12/22 | JV Boys Ice Hockey | Trumbull (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Mon., 12/23 | V Boys Ice Hockey | Milford Coop | Home - Winter Garden Rink-Ridgefield [Directions] | 6:20 p.m. | T 2-2 | |
| Mon., 12/23 | V Girls Basketball | Masuk | Home - Wilton High School Field House [Directions] | 7:00 p.m. | W 34-33 | |
| Mon., 12/23 | JV Girls Basketball | Masuk | Home - Wilton High School Field House [Directions] | 5:15 p.m. | ||
| Mon., 12/23 | FR Girls Basketball | Masuk | Home - Wilton High School Field House [Directions] | 3:30 p.m. | ||
| Thu., 12/26 | JV Boys Ice Hockey | Milford JV Tournament | Away | 2:45 p.m. | ||
| Fri., 12/27 | V Boys Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | 6:00 p.m. | W 62-53 | |
| Fri., 12/27 | JV Boys Ice Hockey | Milford JV Tournament | Away | TBA | ||
| Sat., 12/28 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 12:00 p.m. | L 0-5 | |
| Sat., 12/28 | V Wrestling | Fairfield Warde, Bridgeport Central, Harding/Bassick/Bridgeport Central, Shelton | Home - Wilton Field House [Directions] | 10:00 a.m. | ||
| Mon., 12/30 | V Boys Basketball | University | Away [Directions] | 6:00 p.m. | W 69-64 | |
| Mon., 12/30 | JV Boys Basketball | Newtown | Home - Wilton High School Field House [Directions] | 1:00 p.m. | ||
| Mon., 12/30 | V Girls Basketball | New Milford | Away - New Milford High School [Directions] | 7:00 p.m. | W 47-45 | |
| Mon., 12/30 | JV Girls Basketball | New Milford | Away - New Milford High School [Directions] | 5:15 p.m. | ||
| Mon., 12/30 | FR Girls Basketball | New Milford | Away - New Milford High School [Directions] | 3:30 p.m. | ||
| Sat., 1/4 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 8:35 p.m. | L 1-3 | |
| Sat., 1/4 | V Boys Indoor Track | Darien, Ridgefield, Fairfield Warde, St. Joseph | Home - Wilton Field House [Directions] | 9:30 a.m. | Stamford, Norwalk | |
| Sat., 1/4 | V Wrestling | Warde Invitational | Away | 9:00 a.m. | ||
| Sat., 1/4 | V Girls Ice Hockey | Hall/Conard | Home - So No Icehouse - Norwalk [Directions] | 4:50 p.m. | L 6-1 | |
| Sat., 1/4 | V Girls Indoor Track | Darien, Ridgefield, Fairfield Warde, St. Joseph | Home - Wilton Field House [Directions] | 9:30 a.m. | Stamford, Norwalk | |
| Mon., 1/6 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:00 p.m. | L 43-51 | |
| Mon., 1/6 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | Cancelled | |
| Mon., 1/6 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Cancelled | |
| Mon., 1/6 | V Boys Swimming and Diving | Ridgefield | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Mon., 1/6 | V Girls Basketball | Westhill | Home - Wilton Field House [Directions] | 4:00 p.m. | W 71-42 | |
| Tue., 1/7 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | W 59-56 | |
| Tue., 1/7 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Tue., 1/7 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Tue., 1/7 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | 4:20 p.m. | ||
| Tue., 1/7 | V Girls Basketball | Trinity Catholic | Home - Wilton Field House [Directions] | 7:00 p.m. | W 65-32 | |
| Tue., 1/7 | JV Girls Basketball | Trinity Catholic | Home - Wilton Field House [Directions] | 5:15 p.m. | ||
| Wed., 1/8 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 4-7 | |
| Wed., 1/8 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/8 | V Wrestling | Norwalk | Away - Norwalk High Gym [Directions] | 7:30 p.m. | ||
| Wed., 1/8 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - SoNo Ice House [Directions] | 5:45 p.m. | W 7-2 | |
| Fri., 1/10 | V Boys Basketball | Staples | Home - Wilton Field House [Directions] | 7:00 p.m. | W 60-50 | |
| Fri., 1/10 | JV Boys Basketball | Staples | Home - Wilton Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Staples | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/10 | JV Boys Ice Hockey | Greenwich | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Fri., 1/10 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 7:00 p.m. | W 55-23 | |
| Fri., 1/10 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/11 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 4:20 p.m. | W 4-3 | |
| Sat., 1/11 | V Boys Indoor Track | Danbury, Greenwich, Fairfield Ludlowe, St. Joseph | Home - Wilton Field House [Directions] | 9:30 a.m. | Brein McMahon, Westhill, Stamford | |
| Sat., 1/11 | V Wrestling | Farmington Duals | Away | 9:00 a.m. | ||
| Sat., 1/11 | V Girls Ice Hockey | Greenwich | Away [Directions] | 6:30 p.m. | W 2-1 | |
| Sat., 1/11 | V Girls Indoor Track | Danbury, Greenwich, Fairfield Ludlowe, St. Joseph | Home - Wilton Field House [Directions] | 9:30 a.m. | Brein McMahon, Westhill, Stamford | |
| Mon., 1/13 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | 7:30 p.m. | T 2-2 (OT) | |
| Tue., 1/14 | V Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 7:00 p.m. | W 84-71 | |
| Tue., 1/14 | JV Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | FR Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | V Girls Basketball | St. Joseph | Home - Wilton Field House [Directions] | 7:00 p.m. | W 47-42 | |
| Tue., 1/14 | JV Girls Basketball | St. Joseph | Home - Wilton Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | FR Girls Basketball | St. Joseph | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | V Girls Gymnastics | Darien | Home - Wilton High School Aux. Gym [Directions] | 4:00 p.m. | 132.65, Darien 119.0 | |
| Wed., 1/15 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:10 p.m. | L 0-5 | |
| Wed., 1/15 | V Girls Ice Hockey | Darien | Home - SoNo Ice House [Directions] | 6:00 p.m. | L 8-0 | |
| Fri., 1/17 | V Boys Basketball | Trumbull | Home - Wilton Field House [Directions] | 7:00 p.m. | L 70-79 | |
| Fri., 1/17 | JV Boys Basketball | Trumbull | Home [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Trumbull | Home [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | W 47-43 | |
| Fri., 1/17 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Girls Gymnastics | New Canaan, Westhill | Home - Wilton High School Aux. Gym [Directions] | 5:00 p.m. | 137.75, Westhill 111.15, New Canaan 102.85 | |
| Sat., 1/18 | V Boys Ice Hockey | Trinity Catholic | Home - Winter Garden Rink-Ridgefield [Directions] | 8:50 p.m. | L 1-7 | |
| Sat., 1/18 | V Boys Indoor Track | Fairfield Warde, Trumbull, Fairfield Warde, New Canaan | Home - Wilton Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/18 | V Wrestling | New Milford Invitational | Away | 9:00 a.m. | ||
| Sat., 1/18 | V Girls Ice Hockey | New Canaan | Home - SoNo Ice House [Directions] | 3:45 p.m. | T 1-1 | |
| Sat., 1/18 | V Girls Indoor Track | Fairfield Warde, Trumbull, Fairfield Warde, New Canaan | Home - Wilton Field House [Directions] | 9:30 a.m. | ||
| Mon., 1/20 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | 11:00 a.m. | L 1-2 | Cantebury School |
| Mon., 1/20 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 6:00 p.m. | L 4-2 | |
| Wed., 1/22 | V Boys Ice Hockey | Darien | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 1-5 | |
| Wed., 1/22 | V Wrestling | Brien McMahon | Home - Wilton Field House [Directions] | 6:00 p.m. | Cancelled | |
| Thu., 1/23 | V Boys Basketball | Stamford | Away - Stamford High School [Directions] | 7:00 p.m. | L 47-67 | |
| Thu., 1/23 | JV Boys Basketball | Stamford | Away - Stamford High School [Directions] | 5:15 p.m. | ||
| Thu., 1/23 | FR Boys Basketball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 1/23 | V Girls Gymnastics | Fairfield Warde | Home - clear location [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 1/23 | V Girls Gymnastics | Fairfield Ludlowe | Home - Wilton High School Aux. Gym [Directions] | 4:00 p.m. | 139.4, Ludlowe 139.0, Warde 133.65 | |
| Fri., 1/24 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | L 38-63 | |
| Fri., 1/24 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | V Boys Indoor Track | FCIAC Eastern Division Championships | Home - Wilton Field House [Directions] | 5:00 p.m. | [Detailed Results] | |
| Fri., 1/24 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/24 | V Girls Basketball | Greenwich | Away - Greenwich [Directions] | 4:00 p.m. | W 49-40 | |
| Fri., 1/24 | V Girls Indoor Track | FCIAC Eastern Division Championships | Home - Wilton Field House [Directions] | 5:00 p.m. | ||
| Sat., 1/25 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/25 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | 5:00 p.m. | W 8-2 | |
| Sat., 1/25 | V Boys Indoor Track | FCIAC Central Division Championships | Home - Wilton Field House [Directions] | 2:00 p.m. | ||
| Sat., 1/25 | V Wrestling | Ridgefield Challenge | Away | 9:00 a.m. | ||
| Sat., 1/25 | V Girls Indoor Track | FCIAC Central Division Championships | Home - Wilton Field House [Directions] | 2:00 p.m. | ||
| Mon., 1/27 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:30 p.m. | ||
| Mon., 1/27 | V Girls Basketball | Stamford | Home - Wilton Field House [Directions] | 7:00 p.m. | L 50-55 | |
| Mon., 1/27 | JV Girls Basketball | Stamford | Home - Wilton Field House [Directions] | 5:15 p.m. | ||
| Mon., 1/27 | FR Girls Basketball | Stamford | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Bridgeport Central | Home - Wilton Field House [Directions] | 7:00 p.m. | L 65-70 | |
| Tue., 1/28 | JV Boys Basketball | Bridgeport Central | Home - Wilton Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Boys Basketball | Bridgeport Central | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | W 54-17 | |
| Tue., 1/28 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Girls Gymnastics | Trumbull, Darien | Home - Wilton High School Aux. Gym [Directions] | 5:00 p.m. | 133.05, Trumbull 135.8 | |
| Tue., 1/28 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away [Directions] | 7:45 p.m. | W 7-2 | Rinks at Shelton |
| Wed., 1/29 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 2-5 | |
| Wed., 1/29 | V Boys Indoor Track | FCIAC Championships | Away | 5:00 p.m. | Floyd Little Athletic Center, New Haven, CT | |
| Wed., 1/29 | V Boys Swimming and Diving | Danbury | Home [Directions] | 3:40 p.m. | ||
| Wed., 1/29 | V Wrestling | Fairfield Ludlowe | Home - Wilton Field House [Directions] | 5:00 p.m. | ||
| Wed., 1/29 | V Girls Ice Hockey | Fairfield Warde | Away [Directions] | 6:00 p.m. | W 4-3 | |
| Wed., 1/29 | V Girls Indoor Track | FCIAC Championships | Away | 5:00 p.m. | Floyd Little Athletic Center, New Haven, CT | |
| Thu., 1/30 | V Girls Gymnastics | Staples | Home - Wilton High School Aux. Gym [Directions] | 4:00 p.m. | 133.9, Staples 127.35 | |
| Fri., 1/31 | V Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 7:00 p.m. | W 69-46 | |
| Fri., 1/31 | JV Boys Basketball | Harding | Away [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | Harding | Away [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | JV Boys Ice Hockey | New Canaan | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Harding | Home - Wilton Field House [Directions] | 5:30 p.m. | W 65-29 | |
| Fri., 1/31 | JV Girls Basketball | Harding | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | FR Girls Basketball | Harding | Home - Wilton Field House [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 2/1 | V Boys Ice Hockey | Stamford | Away - Terry Conners Ice Rink [Directions] | 8:10 p.m. | W 5-4 | |
| Sat., 2/1 | V Wrestling | Masuk, Darien, Bristol Central, Greenwich | Home - Wilton Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/1 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - SoNo Ice House [Directions] | 3:45 p.m. | W 6-1 | |
| Tue., 2/4 | V Boys Swimming and Diving | Greenwich | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Tue., 2/4 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away [Directions] | 8:20 p.m. | W 6-5 | |
| Thu., 2/6 | V Boys Swimming and Diving | New Canaan | Home - Wiltom YMCA [Directions] | 3:40 p.m. | ||
| Thu., 2/6 | V Wrestling | Stamford | Away - Stamford High Aux Gym [Directions] | 6:00 p.m. | ||
| Thu., 2/6 | V Girls Gymnastics | Joel Barlow, Weston | Home - Wilton High School Aux. Gym [Directions] | 5:00 p.m. | 134.8, Weston 115.05, Joel Barlow 82.1 | |
| Fri., 2/7 | V Boys Basketball | Norwalk | Home - Wilton Field House [Directions] | 7:00 p.m. | W 60-56 | |
| Fri., 2/7 | JV Boys Basketball | Norwalk | Home [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Norwalk | Home [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Boys Ice Hockey | Trumbull | Home - Winter Garden Rink-Ridgefield [Directions] | 6:30 p.m. | W 4-2 | Senior Night |
| Fri., 2/7 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:45 p.m. | W 50-43 | |
| Fri., 2/7 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:00 p.m. | 131.85, Greenwich 125.85 | |
| Sat., 2/8 | V Wrestling | New Canaan, Trumbull, Ridgefield | Away - NCHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/8 | V Girls Ice Hockey | Greenwich | Home - SoNo Ice House [Directions] | 12:00 p.m. | W 5-3 | |
| Tue., 2/11 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 62-74 | |
| Tue., 2/11 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Tue., 2/11 | V Wrestling | Darien | Away - DHS - South Gym [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 2/11 | V Girls Basketball | Brien McMahon | Home - Wilton Field House [Directions] | 5:45 p.m. | W 63-26 | |
| Tue., 2/11 | JV Girls Basketball | Brien McMahon | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 2/11 | FR Girls Basketball | Joel Barlow | Away - Lower Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/12 | V Boys Ice Hockey | Norwalk | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | W 8-1 | |
| Wed., 2/12 | JV Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | 4:20 p.m. | ||
| Wed., 2/12 | V Boys Swimming and Diving | Darien | Away - YMCA pool [Directions] | 3:00 p.m. | ||
| Fri., 2/14 | V Boys Basketball | Fairfield Warde | Home - Wilton Field House [Directions] | 5:45 p.m. | W 66-48 | |
| Fri., 2/14 | JV Boys Basketball | Fairfield Warde | Home [Directions] | 4:00 p.m. | ||
| Fri., 2/14 | FR Boys Basketball | Fairfield Warde | Home [Directions] | 4:00 p.m. | ||
| Fri., 2/14 | V Wrestling | FCIAC Tournament | Away | 4:30 p.m. | ||
| Fri., 2/14 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:45 p.m. | L 36-41 | |
| Fri., 2/14 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/14 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/15 | V Wrestling | FCIAC Tournament | Away | 4:30 p.m. | ||
| Sat., 2/15 | V Girls Gymnastics | FCIAC Championship | Away [Directions] | 10:30 a.m. | ||
| Sat., 2/15 | V Girls Gymnastics | FCIAC Championships | Away [Directions] | TBA | 130.95 | |
| Sat., 2/15 | V Girls Ice Hockey | New Canaan | Away [Directions] | 8:10 p.m. | L 5-1 | |
| Mon., 2/17 | V Boys Basketball | Fairfield Ludlowe | Home - Wilton Field House [Directions] | 7:00 p.m. | W 58-52 | |
| Mon., 2/17 | JV Boys Basketball | Fairfield Ludlowe | Home [Directions] | 5:15 p.m. | ||
| Mon., 2/17 | FR Boys Basketball | Fairfield Ludlowe | Home [Directions] | 4:00 p.m. | ||
| Mon., 2/17 | JV Boys Ice Hockey | JBWA | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Mon., 2/17 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | L 46-49 | |
| Mon., 2/17 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/17 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/17 | V Girls Ice Hockey | West Haven/SHA | Home - SoNo Ice House [Directions] | 3:10 p.m. | W 8-7 | |
| Wed., 2/19 | V Boys Ice Hockey | Ridgefield | Home - Winter Garden Rink-Ridgefield [Directions] | 5:10 p.m. | L 0-1 (OT) | |
| Wed., 2/19 | V Girls Basketball | Bassick | Home - Wilton Field House [Directions] | 5:45 p.m. | W 56-15 | |
| Wed., 2/19 | JV Girls Basketball | Bassick | Home - Wilton Field House [Directions] | 4:00 p.m. | ||
| Wed., 2/19 | V Girls Ice Hockey | Simsbury | Away [Directions] | 5:10 p.m. | Cancelled | |
| Thu., 2/20 | V Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 7:00 p.m. | W 60-47 | |
| Thu., 2/20 | JV Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/20 | FR Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/20 | V Girls Gymnastics | New Milford, Fairfield Ludlowe | Away [Directions] | 5:00 p.m. | 130.15, new Milford 122.55 | |
| Fri., 2/21 | V Girls Ice Hockey | Darien | Away [Directions] | 6:00 p.m. | W 7-0 | |
| Sat., 2/22 | V Boys Ice Hockey | St. Joseph | Home - Winter Garden Rink-Ridgefield [Directions] | 12:50 p.m. | L 3-7 | |
| Sat., 2/22 | V Boys Swimming and Diving | JV FCIAC's | Away [Directions] | 1:30 p.m. | ||
| Sat., 2/22 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 8:50 p.m. | L 3-2 | |
| Mon., 2/24 | V Boys Basketball | Ridgefield | Home - Wilton Field House [Directions] | 7:00 p.m. | L 37-65 | |
| Mon., 2/24 | JV Boys Basketball | Ridgefield | Home [Directions] | 5:15 p.m. | ||
| Mon., 2/24 | FR Boys Basketball | Ridgefield | Home [Directions] | 4:00 p.m. | ||
| Tue., 2/25 | V Boys Swimming and Diving | FCIAC Trials | Away [Directions] | 4:30 p.m. | ||
| Wed., 2/26 | V Boys Basketball | Danbury | Home - Wilton Field House [Directions] | 7:00 p.m. | W 64-55 | Senior Night |
| Wed., 2/26 | JV Boys Basketball | Danbury | Home [Directions] | 5:15 p.m. | ||
| Wed., 2/26 | FR Boys Basketball | Danbury | Home [Directions] | 4:00 p.m. | ||
| Wed., 2/26 | V Boys Ice Hockey | Greenwich | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 0-6 | |
| Wed., 2/26 | V Boys Swimming and Diving | FCIAC Diving | Away [Directions] | 4:30 p.m. | ||
| Thu., 2/27 | V Boys Swimming and Diving | FCIAC Finals | Away [Directions] | 6:30 p.m. | ||
| Sat., 3/1 | V Girls Gymnastics | CIAC Class Championship | Away [Directions] | TBA | ||
| Sat., 3/1 | V Girls Gymnastics | Class Championships | Away | TBA | ||
| Sat., 3/8 | V Girls Gymnastics | CIAC Open Championship | Away [Directions] | TBA | ||
| Sat., 3/8 | V Girls Gymnastics | CIAC Open Championships | Away | TBA | ||
| Thu., 3/13 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 3/15 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 6:15 p.m. | ||
| Sat., 3/15 | V Girls Gymnastics | Regional Championships | Away | TBA | ||
| Wed., 3/19 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 7:15 p.m. | ||
| Thu., 3/20 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/22 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Thu., 3/27 | V Baseball | Immaculate (Scrim.) | Home - WHS Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Sat., 3/29 | V Boys Lacrosse | Ridgefield (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 3/29 | V Girls Lacrosse | Wilton Playday | Home - Lilly Field - Turf [Directions] | 9:00 a.m. | ||
| Tue., 4/1 | V Baseball | Darien (Scrim.) | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/2 | V Baseball | Brien McMahon (Scrim.) | Home - WHS Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/2 | V Boys Lacrosse | Glastonbury (Scrim.) | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Thu., 4/3 | V Softball | Immaculate (Scrim.) | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/5 | V Baseball | Kennedy (Scrim.) | Home - WHS Varsity Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/5 | V Girls Lacrosse | New Canaan Playday | Away | TBA | ||
| Wed., 4/9 | V Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:00 p.m. | L 4-7 | |
| Wed., 4/9 | JV Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Boys Lacrosse | Norwalk | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 15-7 | |
| Wed., 4/9 | JV Boys Lacrosse | Norwalk | Home - Fujitani Field - Turf [Directions] | 5:00 p.m. | ||
| Wed., 4/9 | V Boys Tennis | Fairfield Warde | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 4/9 | JV Boys Tennis | Fairfield Warde | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Girls Lacrosse | Trumbull | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 18-3 | |
| Wed., 4/9 | JV Girls Lacrosse | Trumbull | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Girls Outdoor Track | Darien, Weston | Away [Directions] | 4:00 p.m. | Lost to Darien 36-109 | @ Weston HS |
| Wed., 4/9 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | 3:00 p.m. | L 7-12 | Non-League |
| Wed., 4/9 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Wed., 4/9 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods Middle School Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | V Baseball | Brookfield | Home - WHS Varsity Baseball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 4/10 | FR Baseball | Brookfield | Away - BHS Baseball Field [Directions] | 4:30 p.m. | ||
| Thu., 4/10 | FR Boys Lacrosse | Joel Barlow | Home - Allen's Field #1 [Directions] | 4:30 p.m. | ||
| Thu., 4/10 | V Boys Outdoor Track | Darien | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | Loss 65-85 | |
| Thu., 4/10 | V Boys Tennis | Norwalk | Away - Norwalk High Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/10 | V Girls Golf | Fairfield Ludlowe, Trumbull | Home - Silvermine Golf Club [Directions] | 3:15 p.m. | Wilton - 198 Ludlow - 183 Trumbull - 190 Wilton - loss | |
| Thu., 4/10 | V Girls Tennis | Norwalk | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/11 | V Baseball | Darien | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 1-8 | |
| Fri., 4/11 | JV Baseball | Darien | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/11 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | ||
| Fri., 4/11 | FR Boys Lacrosse | Darien | Home - Allen's Field #1 [Directions] | 4:30 p.m. | ||
| Fri., 4/11 | V Girls Lacrosse | New Canaan | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 9-8 | |
| Fri., 4/11 | JV Girls Lacrosse | New Canaan | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | FR Girls Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | 4:30 p.m. | L 0-12 | |
| Sat., 4/12 | V Boys Lacrosse | Mercer Island (WA) | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 15-12 | |
| Sat., 4/12 | V Softball | Norwalk | Home - WHS Varsity Softball Field [Directions] | 11:00 a.m. | L 1-6 | Non-League |
| Mon., 4/14 | V Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | L 0-8 | |
| Mon., 4/14 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/14 | FR Baseball | New Canaan | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/14 | V Boys Tennis | Stamford | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/14 | V Girls Lacrosse | Garden City (NY) | Home - Lilly Field - Turf [Directions] | 12:00 p.m. | L 5-16 | |
| Mon., 4/14 | V Softball | New Canaan | Home - WHS Varsity Softball Field [Directions] | 1:00 p.m. | L 4-11 | |
| Mon., 4/14 | V Girls Tennis | Stamford | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/15 | V Boys Lacrosse | New Canaan | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 8-14 | |
| Wed., 4/16 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | L 0-9 | |
| Wed., 4/16 | JV Baseball | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | ||
| Wed., 4/16 | FR Baseball | Westhill | Home - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/16 | JV Boys Lacrosse | New Canaan | Home - Fujitani Field - Turf [Directions] | 3:00 p.m. | ||
| Wed., 4/16 | V Boys Tennis | Weston | Home - WHS Tennis Courts [Directions] | 1:00 p.m. | W 6-1 | |
| Wed., 4/16 | V Girls Lacrosse | Ridgefield | Home - Lilly Field - Turf [Directions] | 12:30 p.m. | W 13-4 | |
| Wed., 4/16 | V Softball | Westhill | Home - WHS Varsity Softball Field [Directions] | 1:00 p.m. | L 1-16(5) | |
| Thu., 4/17 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:00 p.m. | W 9-2 | |
| Thu., 4/17 | JV Baseball | Trinity Catholic | Home - Wilton [Directions] | 12:00 p.m. | ||
| Thu., 4/17 | FR Baseball | Trinity Catholic | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 12:00 p.m. | ||
| Thu., 4/17 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 6:00 p.m. | L 7-18 | |
| Thu., 4/17 | JV Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/17 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Thu., 4/17 | V Boys Tennis | Bridgeport Central | Home - WHS Tennis Courts [Directions] | 2:30 p.m. | W 7-0 | |
| Thu., 4/17 | V Softball | Trinity Catholic | Home - WHS Varsity Softball Field [Directions] | 1:00 p.m. | L 5-11 | |
| Thu., 4/17 | V Girls Tennis | Bridgeport Central | Home [Directions] | 2:30 p.m. | W 7-0 | |
| Sat., 4/19 | V Boys Lacrosse | John Jay (NY) | Away | 7:00 p.m. | L 8-12 | |
| Sat., 4/19 | JV Boys Lacrosse | John Jay (NY) | Away | 4:00 p.m. | ||
| Sat., 4/19 | V Girls Lacrosse | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 12:00 p.m. | W 14-6 | |
| Sat., 4/19 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 10:00 a.m. | ||
| Mon., 4/21 | V Baseball | Staples | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | W 3-2 | |
| Mon., 4/21 | JV Baseball | Staples | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/21 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/21 | V Boys Golf | Darien | Home - Rolling Hills [Directions] | 3:00 p.m. | Tie 173 | |
| Mon., 4/21 | V Boys Golf | Fairfield Ludlowe | Home - Rolling Hills [Directions] | TBA | Won 173-178 | |
| Mon., 4/21 | JV Boys Golf | Greenwich | Home - Rolling Hills [Directions] | TBA | ||
| Mon., 4/21 | V Girls Outdoor Track | St. Joseph, Ridgefield | Away - Ridgefield HS [Directions] | 3:30 p.m. | ||
| Mon., 4/21 | V Softball | Staples | Away - Wakeman Field C [Directions] | 4:00 p.m. | L 4-8 | |
| Tue., 4/22 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:15 p.m. | L 7-20 | |
| Tue., 4/22 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:15 p.m. | ||
| Tue., 4/22 | FR Boys Lacrosse | St. Anthonys (NY) | Home - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Outdoor Track | St. Joseph, Ridgefield | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/22 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:30 p.m. | Loss 233-207 | |
| Tue., 4/22 | V Girls Lacrosse | Norwalk | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 18-2 | |
| Tue., 4/22 | JV Girls Lacrosse | Norwalk | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | FR Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Girls Tennis | Darien | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 4/22 | JV Girls Tennis | Darien | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Baseball | St. Joseph | Away - St. Joseph High School [Directions] | 4:30 p.m. | L 2-6 | |
| Wed., 4/23 | JV Baseball | St. Joseph | Away - Madison Middle School, Trumbull [Directions] | 4:30 p.m. | ||
| Wed., 4/23 | FR Baseball | St. Joseph | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/23 | V Boys Golf | St. Joseph, New Canaan | Away - Tashua Knolls, Trumbull [Directions] | 3:15 p.m. | Wilton - 175 St. Joseph - 193 | |
| Wed., 4/23 | FR Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Wed., 4/23 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | W 11-5 | |
| Wed., 4/23 | JV Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/23 | V Softball | St. Joseph | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | L 0-12 | |
| Wed., 4/23 | JV Softball | St. Joseph | Home - JV Softball Field [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 4/24 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | 3:15 p.m. | Wilton 168 Trinity 176 | |
| Thu., 4/24 | V Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:30 p.m. | L 6-17 | |
| Thu., 4/24 | JV Boys Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:30 p.m. | ||
| Thu., 4/24 | V Boys Tennis | Greenwich | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Thu., 4/24 | JV Boys Tennis | Greenwich | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | V Girls Golf | Darien | Away - Woodway CC [Directions] | 3:00 p.m. | Wilton 231 Darien 208 | |
| Thu., 4/24 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:30 p.m. | L 4-15 | |
| Thu., 4/24 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Thu., 4/24 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Fri., 4/25 | V Baseball | Trumbull | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 0-8 | |
| Fri., 4/25 | JV Baseball | Trumbull | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/25 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 4/25 | FR Boys Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:30 p.m. | ||
| Fri., 4/25 | FR Girls Lacrosse | Darien | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| Sat., 4/26 | V Girls Lacrosse | Northport (NY) | Away | 3:00 p.m. | W 10-9 | |
| Sat., 4/26 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Mon., 4/28 | V Baseball | Stamford | Away - Stamford High School [Directions] | 4:30 p.m. | W 4-0 | |
| Mon., 4/28 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:30 p.m. | ||
| Mon., 4/28 | FR Baseball | Stamford | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/28 | V Boys Tennis | Fairfield Ludlowe | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 4/28 | JV Boys Tennis | Fairfield Ludlowe | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Girls Outdoor Track | Greenwich, Trumbull | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | Greenwich - 81 Wilton - 64 Trumbull - 84 Wilton - 61 | |
| Mon., 4/28 | V Softball | Stamford | Home - WHS Varsity Softball Field [Directions] | 7:00 p.m. | L 3-11 | |
| Mon., 4/28 | JV Softball | Stamford | Home - JV Softball Field [Directions] | 4:00 p.m. | Cancelled | |
| Mon., 4/28 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Mon., 4/28 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | FR Baseball | Greenwich | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | V Boys Lacrosse | Trinity Catholic | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | W 17-0 | |
| Tue., 4/29 | JV Boys Lacrosse | Bridgeport Central | Home - Whitten Field [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | FR Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/29 | V Boys Outdoor Track | Greenwich, Trumbull | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | Danbury - 203 Wilton - 229 | |
| Tue., 4/29 | V Girls Lacrosse | Newtown | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 10-4 | |
| Tue., 4/29 | JV Girls Lacrosse | Newtown | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | V Softball | Greenwich | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | L 2-12 | |
| Wed., 4/30 | V Boys Golf | Bassick, Bridgeport Central, Harding | Away - Fairchild-Wheeler [Directions] | 3:15 p.m. | Wilton - 166 Harding - 257 | |
| Thu., 5/1 | V Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | W 2-1(9) | |
| Thu., 5/1 | V Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 13-5 | |
| Thu., 5/1 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:30 p.m. | ||
| Thu., 5/1 | V Boys Tennis | New Canaan | Home - WHS Tennis Courts [Directions] | 4:30 p.m. | W 4-3 | |
| Thu., 5/1 | JV Boys Tennis | New Canaan | Home - Middlebrook School [Directions] | 4:30 p.m. | ||
| Thu., 5/1 | V Girls Golf | New Canaan | Home - Silvermine Golf Club [Directions] | 3:15 p.m. | Wilton-189 New Canaan-199 | |
| Thu., 5/1 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 5/2 | V Baseball | Bridgeport Central | Home - WHS Varsity Baseball Field [Directions] | 7:00 p.m. | W 8-2 | |
| Fri., 5/2 | JV Baseball | Bridgeport Central | Home - JV Baseball Field [Directions] | 4:15 p.m. | Cancelled | |
| Fri., 5/2 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Fri., 5/2 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Girls Lacrosse | St. Joseph | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 17-1 | |
| Fri., 5/2 | JV Girls Lacrosse | St. Joseph | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | FR Girls Lacrosse | Trumbull | Away - Varsity Grass Field [Directions] | 4:30 p.m. | ||
| Fri., 5/2 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | 4:00 p.m. | W 5-2 | |
| Fri., 5/2 | V Girls Tennis | Ridgefield | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 5/2 | JV Girls Tennis | Ridgefield | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Sat., 5/3 | V Boys Lacrosse | St. Anthonys (NY) | Home - Fujitani Field - Turf [Directions] | 3:00 p.m. | L 6-15 | |
| Sat., 5/3 | JV Boys Lacrosse | St. Anthonys (NY) | Home [Directions] | 12:30 p.m. | ||
| Mon., 5/5 | V Baseball | Harding | Away - Beardsley Park - Baseball [Directions] | 4:30 p.m. | W 22-2 | |
| Mon., 5/5 | JV Baseball | Harding | Away - Seaside Park [Directions] | 4:30 p.m. | ||
| Mon., 5/5 | V Boys Golf | Staples | Home - Rolling Hills [Directions] | 3:30 p.m. | Wilton-184 Staples-171 | |
| Mon., 5/5 | JV Boys Golf | Staples | Home - Rolling Hills [Directions] | 3:30 p.m. | ||
| Mon., 5/5 | FR Boys Lacrosse | Danbury | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/5 | V Girls Outdoor Track | Fairfield Warde, Bridgeport Central | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Softball | Harding | Home - WHS Varsity Softball Field [Directions] | 7:00 p.m. | W 17-3 | |
| Mon., 5/5 | V Girls Tennis | Trumbull | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/6 | V Boys Golf | Trumbull | Home - Rolling Hills [Directions] | 3:30 p.m. | Wilton - 195 Trumbull - 164 | |
| Tue., 5/6 | V Boys Lacrosse | St. Joseph | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 14-12 | |
| Tue., 5/6 | JV Boys Lacrosse | St. Joseph | Home - Whiten Field [Directions] | 5:00 p.m. | ||
| Tue., 5/6 | FR Boys Lacrosse | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Outdoor Track | Fairfield Warde, Bridgeport Central | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Tennis | Westhill | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 5/6 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | W 10-5 | |
| Tue., 5/6 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 5/6 | V Girls Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/6 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Boys Golf | Westhill | Away - Hubbard Brennan Golf Course [Directions] | 3:30 p.m. | Wilton-161 Westhill-178 | |
| Wed., 5/7 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | ||
| Wed., 5/7 | JV Girls Tennis | Greenwich | Home [Directions] | 4:00 p.m. | ||
| Thu., 5/8 | V Baseball | Norwalk | Home - WHS Varsity Baseball Field [Directions] | 6:30 p.m. | W 1-0 | |
| Thu., 5/8 | JV Baseball | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:30 p.m. | Cancelled | |
| Thu., 5/8 | FR Baseball | Norwalk | Away - City Hall Field [Directions] | 4:30 p.m. | Cancelled | |
| Thu., 5/8 | JV Boys Golf | Staples, Darien | Away - Longshore [Directions] | 3:00 p.m. | ||
| Thu., 5/8 | V Boys Lacrosse | Staples | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | L 8-9 | |
| Thu., 5/8 | JV Boys Lacrosse | Staples | Home - Whitten Field [Directions] | 4:00 p.m. | ||
| Thu., 5/8 | V Girls Golf | Fairfield Warde | Home - Silvermine Golf Club [Directions] | 3:15 p.m. | Wilton - 195 Warde - 179 | |
| Thu., 5/8 | V Girls Golf | Ridgefield | Home - Silver Mine CC [Directions] | 3:30 p.m. | Wilton - 195 Ridgefield - 169 | Non League |
| Thu., 5/8 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 8-13 | |
| Thu., 5/8 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 5/9 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 5/10 | V Boys Lacrosse | Brien McMahon | Home - Fujitani Field - Turf [Directions] | 3:00 p.m. | L 9-10(OT) | |
| Sat., 5/10 | JV Boys Lacrosse | Brien McMahon | Home - Fujitani Field - Turf [Directions] | 5:00 p.m. | ||
| Sat., 5/10 | V Girls Lacrosse | Sacred Heart-Hempstead (NY) | Away | 1:00 p.m. | L 9-11 | |
| Sat., 5/10 | FR Girls Lacrosse | Weston | Home - Lilly Field - Turf [Directions] | 10:00 a.m. | ||
| Sat., 5/10 | V Girls Tennis | St. Joseph | Home - WHS Tennis Courts [Directions] | 2:00 p.m. | W 7-0 | |
| Mon., 5/12 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 4-12 | |
| Mon., 5/12 | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | 4:30 p.m. | ||
| Mon., 5/12 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:45 p.m. | Wilton-167 New Canaan - 159 | |
| Mon., 5/12 | JV Boys Golf | New Canaan | Home - Rolling Hills [Directions] | 3:15 p.m. | ||
| Mon., 5/12 | JV Boys Golf | Darien | Home - Rolling Hills [Directions] | 3:30 p.m. | ||
| Mon., 5/12 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Mon., 5/12 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | Cancelled | |
| Mon., 5/12 | V Girls Outdoor Track | Bassick, New Canaan | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Softball | Brien McMahon | Home - WHS Varsity Softball Field [Directions] | 7:00 p.m. | W 3-2 | |
| Mon., 5/12 | V Girls Tennis | Staples | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 5/13 | V Boys Golf | Fairfield Warde | Home - Rolling Hills [Directions] | 3:15 p.m. | Wilton - 180 Warde - 184 | |
| Tue., 5/13 | JV Boys Golf | Fairfield Warde | Home - Rolling Hills [Directions] | TBA | ||
| Tue., 5/13 | V Boys Lacrosse | Yorktown (NY) | Away | 7:00 p.m. | L 6-13 | |
| Tue., 5/13 | JV Boys Lacrosse | Yorktown (NY) | Away | 4:30 p.m. | ||
| Tue., 5/13 | V Boys Outdoor Track | New Canaan, Bassick | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Tue., 5/13 | V Boys Tennis | Danbury | Home - Wilton High School [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/13 | JV Boys Tennis | Ridgefield | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Tue., 5/13 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Wilton - 240 Ludlow - 219 | |
| Tue., 5/13 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:30 p.m. | W 20-3 | |
| Tue., 5/13 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Tue., 5/13 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | 4:30 p.m. | L 1-7 | |
| Tue., 5/13 | V Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/14 | V Baseball | Fairfield Warde | Home - WHS Varsity Baseball Field [Directions] | 7:00 p.m. | W 1-0 | |
| Wed., 5/14 | JV Baseball | Fairfield Warde | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/14 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:30 p.m. | ||
| Wed., 5/14 | V Boys Golf | Greenwich | Away - Roundhill Country Club [Directions] | 3:15 p.m. | Wilton - 171 Greenwich - 148 | |
| Wed., 5/14 | JV Boys Golf | Greenwich | Away - TBA [Directions] | 3:15 p.m. | ||
| Wed., 5/14 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 10-9(OT) | |
| Wed., 5/14 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 5/14 | FR Boys Lacrosse | St. Joseph | Away [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 5/14 | V Boys Tennis | St. Joseph | Away - St. Joseph High School [Directions] | 5:15 p.m. | W 7-0 | |
| Wed., 5/14 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | L 8-17 | |
| Wed., 5/14 | JV Girls Tennis | Staples | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Thu., 5/15 | V Baseball | Fairfield Ludlowe | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 2-4 | |
| Thu., 5/15 | JV Baseball | Fairfield Ludlowe | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 5/15 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:30 p.m. | ||
| Thu., 5/15 | V Boys Golf | Brien McMahon, Stamford | Away - Oak Hills [Directions] | 3:30 p.m. | Wilton - 160 McMahon - 186 Stamford - 211 | |
| Thu., 5/15 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | W 7-0 | |
| Thu., 5/15 | V Girls Golf | Greenwich | Home - Silvermine Golf Club [Directions] | 3:15 p.m. | Wilton - 206 Greenwich - 151 | |
| Thu., 5/15 | V Girls Lacrosse | Stamford | Away - Stamford High School [Directions] | 4:30 p.m. | W 15-3 | |
| Thu., 5/15 | JV Girls Lacrosse | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | ||
| Thu., 5/15 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:30 p.m. | L 4-14 | |
| Thu., 5/15 | V Girls Tennis | Trinity Catholic | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/15 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | ||
| Fri., 5/16 | V Boys Lacrosse | Fairfield Warde | Home - Fujitani Field - Turf [Directions] | 6:30 p.m. | L 8-9(OT) | |
| Fri., 5/16 | JV Boys Lacrosse | Fairfield Warde | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Fri., 5/16 | V Girls Tennis | Danbury | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Sat., 5/17 | FR Girls Lacrosse | Greenwich | Home - Lilly Field - Turf [Directions] | 10:00 a.m. | ||
| Sat., 5/17 | JV Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Mon., 5/19 | V Baseball | Bassick | Away [Directions] | 4:30 p.m. | W 17-0 | |
| Mon., 5/19 | V Boys Golf | Norwalk | Home - Rolling Hills [Directions] | 3:15 p.m. | Wilton - 170 Norwalk - 186 | |
| Mon., 5/19 | V Boys Golf | Danbury | Home - Rolling Hills [Directions] | 3:15 p.m. | Wilton - 170 Danbury - 179 | |
| Mon., 5/19 | FR Boys Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 4:30 p.m. | ||
| Mon., 5/19 | V Boys Tennis | Brien McMahon | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/19 | FR Girls Lacrosse | New Canaan | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Girls Outdoor Track | Danbury, Stamford | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Softball | Bassick | Home - WHS Varsity Softball Field [Directions] | 7:00 p.m. | W 15-0 | |
| Mon., 5/19 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/20 | V Boys Golf | Ridgefield | Home - Silver Spring CC [Directions] | TBA | Wilton - 164 Ridgefield - 147 | |
| Tue., 5/20 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:15 p.m. | ||
| Tue., 5/20 | FR Boys Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Tue., 5/20 | V Boys Outdoor Track | Stamford, Danbury | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/20 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | ||
| Tue., 5/20 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | Wilton - 247 New Canaan - 233 | |
| Tue., 5/20 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:30 p.m. | W 13-8 | |
| Tue., 5/20 | JV Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | ||
| Tue., 5/20 | FR Girls Lacrosse | Ridgefield | Home - Allen's Field #2 [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Baseball | Ridgefield | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 0-3 | |
| Wed., 5/21 | JV Baseball | Ridgefield | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/21 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:30 p.m. | ||
| Wed., 5/21 | V Boys Golf | Stamford | Home - Rolling Hills [Directions] | 3:15 p.m. | Cancelled | |
| Wed., 5/21 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | 3:15 p.m. | Cancelled | |
| Wed., 5/21 | JV Boys Tennis | Greenwich | Home - Middlebrook School [Directions] | 4:30 p.m. | ||
| Wed., 5/21 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | L 2-11 | |
| Wed., 5/21 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | L 4-3 | |
| Thu., 5/22 | JV Boys Golf | Darien, New Canaan | Away - Woodway CC [Directions] | 3:15 p.m. | ||
| Thu., 5/22 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 5/22 | V Boys Tennis | Westhill | Away - Old Greenwich Tennis Association [Directions] | 3:00 p.m. | L 1-4 | |
| Thu., 5/22 | V Girls Golf | Darien | Home - Silvermine Golf Club [Directions] | 3:15 p.m. | Wilton - 180 Darien - 172 | |
| Thu., 5/22 | FR Girls Lacrosse | Greenwich | Home - Allen's Field #2 [Directions] | 4:30 p.m. | ||
| Thu., 5/22 | V Softball | Danbury | Away - Danbury High Varsity Softball Field [Directions] | 4:30 p.m. | L 0-4 | |
| Fri., 5/23 | V Baseball | Danbury | Home - WHS Varsity Baseball Field [Directions] | 2:00 p.m. | L 0-3 | |
| Fri., 5/23 | JV Baseball | Danbury | Home - JV Baseball Field [Directions] | 2:00 p.m. | ||
| Fri., 5/23 | FR Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 5/23 | V Boys Lacrosse | FCIAC 1/4 Finals | Home - Fujitani Field - Turf [Directions] | TBA | ||
| Fri., 5/23 | V Girls Lacrosse | Danbury | Home - Lilly Field - Turf [Directions] | 2:00 p.m. | W 12-3 | |
| Mon., 5/26 | V Boys Lacrosse | FCIAC Semi Finals | Away | TBA | Cancelled | |
| Tue., 5/27 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:00 p.m. | Wilton - 217 Ridgefield - 180 | |
| Tue., 5/27 | JV Girls Tennis | Harding | Home - Middlebrook School [Directions] | 4:30 p.m. | ||
| Thu., 5/29 | V Girls Golf | Staples | Home - Silvermine Golf Club [Directions] | 3:15 p.m. | Wilton - 197 Staples - 151 | |
| Sat., 5/31 | V Girls Tennis | Branford | Home [Directions] | 10:00 a.m. | W 7-0 | |
| Mon., 6/2 | V Baseball | Glastonbury | Away - Riverfront Field, Glastonbury [Directions] | 3:30 p.m. | ||
| Mon., 6/2 | V Girls Tennis | Lauralton Hall | Away [Directions] | 3:00 p.m. | ||
| Tue., 6/3 | V Girls Lacrosse | Guilford | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||