| Wilton 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 883 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | FR Baseball | Stamford | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | TBA | ||
| TBA | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | TBA | ||
| TBA | FR Boys Lacrosse | Fairfield Ludlowe | Home - Allen's Field [Directions] | 5:00 p.m. | ||
| TBA | FR Boys Lacrosse | Joel Barlow | Away - Field D [Directions] | TBA | ||
| TBA | V Boys Outdoor Track | Westhill | Home - WHS Track [Directions] | TBA | ||
| TBA | JV Boys Tennis | Ridgefield | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| TBA | JV Girls Basketball | New Milford | Away - New Milford HS [Directions] | 5:15 p.m. | ||
| TBA | JV Girls Basketball | Staples | Home - Nicholas Zeoli Field House [Directions] | TBA | ||
| TBA | JV Field Hockey | Stamford | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| TBA | FR Field Hockey | Darien | Home - Wilton HS - Grass Field [Directions] | 4:15 p.m. | ||
| TBA | FR Girls Lacrosse | New Fairfield | Away [Directions] | TBA | ||
| TBA | JV Girls Soccer | Staples | Home - Allen's Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Greenwich | Home - Allen's Field [Directions] | TBA | ||
| TBA | JV Girls Tennis | Greenwich | Home - Middlebrook School [Directions] | TBA | ||
| TBA | FR Girls Volleyball | Fairfield Ludlowe | Home - Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Sun., 8/30 | V Football | Wilton Jamboree | Home - Fujitani Field - Turf [Directions] | 12:30 p.m. | ||
| Sun., 8/30 | V Boys Soccer | South Kent (Scrim.) | Home - Lilly Field - Turf [Directions] | 11:30 a.m. | ||
| Sun., 8/30 | V Field Hockey | Darien Jamboree | Away | 1:00 p.m. | ||
| Mon., 8/31 | V Football | Tournament Game - Opponent Not Known (Scrim.) | Home - Fujitani Field - Turf [Directions] | 4:15 p.m. | ||
| Tue., 9/1 | V Boys Soccer | Wilton Jamboree | Home - Lilly Field - Turf [Directions] | TBA | Branford/Foran/New Milford/ND-FFLD | |
| Tue., 9/1 | V Field Hockey | Greenwich Academy (Scrim.) | Home [Directions] | 3:30 p.m. | ||
| Tue., 9/1 | V Girls Volleyball | East Haven (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 3:30 p.m. | ||
| Tue., 9/1 | JV Girls Volleyball | East Haven (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 3:30 p.m. | ||
| Tue., 9/1 | FR Girls Volleyball | East Haven (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 3:30 p.m. | ||
| Wed., 9/2 | FR Football | Brookfield (Scrim.) | Home - Wilton HS - Grass Field [Directions] | Cancelled | Cancelled | |
| Wed., 9/2 | FR Football | Brookfield (Scrim.) | Home - Wilton HS - Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/3 | V Football | Naugatuck (Scrim.) | Away [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | V Football | Naugatuck (Scrim.) | Away [Directions] | TBA | ||
| Thu., 9/3 | V Boys Soccer | South Windsor (Scrim.) | Home - Lilly Field - Turf [Directions] | 5:00 p.m. | ||
| Thu., 9/3 | V Girls Soccer | Bethel (Scrim.) | Away - Bethel HS [Directions] | 4:15 p.m. | ||
| Sat., 9/5 | V Boys Soccer | Guilford (Scrim.) | Away - Kavanaugh Turf Field at GHS [Directions] | 10:00 a.m. | ||
| Sat., 9/5 | V Girls Volleyball | Weston (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 10:00 a.m. | ||
| Tue., 9/8 | V Boys Soccer | Joel Barlow (Scrim.) | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | ||
| Tue., 9/8 | JV Boys Soccer | Staples (Scrim.) | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 9/8 | V Girls Soccer | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 5:00 p.m. | V & JV | |
| Wed., 9/9 | V Football | Norwalk (Scrim.) | Away - Testa Field, NHS [Directions] | 7:00 p.m. | ||
| Wed., 9/9 | FR Football | Norwalk (Scrim.) | Away - Nathan Hale M.S. Lower [Directions] | 5:30 p.m. | ||
| Wed., 9/9 | V Field Hockey | Greenwich (Scrim.) | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Wed., 9/9 | JV Field Hockey | Greenwich (Scrim.) | Home - Fujitani Field - Turf [Directions] | 5:15 p.m. | ||
| Wed., 9/9 | V Girls Volleyball | Fairfield Warde (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 9/9 | JV Girls Volleyball | Fairfield Warde (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 9/9 | FR Girls Volleyball | Fairfield Warde (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Fri., 9/11 | FR Girls Soccer | Darien | Home [Directions] | 4:15 p.m. | ||
| Fri., 9/11 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 9/11 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 9/12 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:00 p.m. | L 0-3 | Non League |
| Sat., 9/12 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:00 p.m. | L 1-2 | |
| Sat., 9/12 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 1:00 p.m. | W 3-1 | |
| Tue., 9/15 | V Boys Cross Country | Danbury, Westhill, Staples | Away - Tarrywile Park [Directions] | 4:00 p.m. | Wilton - 29/NC-27 WIlton - 18/RFLD - 41 Wilton - 23/St. Joseph - 36 Wilton - 15/Trinity - 50 | |
| Tue., 9/15 | V Boys Soccer | Bridgeport Central | Home - Lilly Field - Turf [Directions] | 4:15 p.m. | W 3-1 | |
| Tue., 9/15 | JV Boys Soccer | Bridgeport Central | Home - Allen's Field [Directions] | 4:15 p.m. | W 1-0 | |
| Tue., 9/15 | V Girls Cross Country | Danbury, Westhill, Staples | Away - Tarrywile Park [Directions] | 4:00 p.m. | Wilton - 21/NC - 36 Wilton - 18/Trinity - 50 WIlton - 36/RFLD - 21 Wilton - 15/St. Joseph - 50 | |
| Tue., 9/15 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 9/15 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | W 5-0 | |
| Tue., 9/15 | V Girls Swimming and Diving | New Canaan | Home - New Canaan YMCA [Directions] | 3:30 p.m. | Wilton - 82 New Canaan - 102 | Diving Only |
| Wed., 9/16 | FR Football | Brien McMahon | Home - wilton [Directions] | 7:00 p.m. | ||
| Wed., 9/16 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:30 p.m. | W 4-0 | |
| Wed., 9/16 | V Girls Swimming and Diving | New Canaan | Home - Wilton YMCA [Directions] | 4:00 p.m. | New Canaan - 102 Wilton - 82 | |
| Wed., 9/16 | V Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 7:00 p.m. | W 3-1 | |
| Wed., 9/16 | JV Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 9/16 | FR Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | W 2-1 | |
| Thu., 9/17 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | L 2-3 | |
| Thu., 9/17 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | W 2-1 | |
| Thu., 9/17 | FR Boys Soccer | Greenwich | Home - Allen's Field [Directions] | 4:15 p.m. | L 0-5 | |
| Thu., 9/17 | V Field Hockey | Westhill | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 6-0 | |
| Thu., 9/17 | JV Field Hockey | Westhill | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| Thu., 9/17 | FR Field Hockey | Westhill | Away [Directions] | Cancelled | Cancelled | |
| Fri., 9/18 | V Football | Brien McMahon | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 3-28 | |
| Fri., 9/18 | V Girls Soccer | Greenwich | Home - Lilly Field - Turf [Directions] | 3:30 p.m. | L 0-2 | |
| Fri., 9/18 | FR Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 9/18 | V Girls Volleyball | Trinity Catholic | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-3 | |
| Fri., 9/18 | JV Girls Volleyball | Trinity Catholic | Home - Nick Zeoli Field House [Directions] | 6:00 p.m. | W 2-1 | |
| Sat., 9/19 | V Boys Cross Country | Wilton Invitational | Home - Allen's Field [Directions] | 9:30 a.m. | ||
| Sat., 9/19 | V Boys Soccer | St. Joseph | Home - Lilly Field - Turf [Directions] | 3:00 p.m. | W 3-0 | |
| Sat., 9/19 | JV Boys Soccer | St. Joseph | Home - Allen's Field [Directions] | 3:00 p.m. | W 2-0 | |
| Sat., 9/19 | V Girls Cross Country | Wilton Invitational | Home [Directions] | 9:30 a.m. | ||
| Mon., 9/21 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:30 p.m. | W 1-0 | |
| Mon., 9/21 | JV Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:30 p.m. | W 3-2 | |
| Mon., 9/21 | FR Boys Soccer | Fairfield Warde | Home - Allen's Field [Directions] | 4:15 p.m. | W 2-0 | |
| Mon., 9/21 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:30 p.m. | L 1-3 | |
| Mon., 9/21 | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:30 p.m. | ||
| Mon., 9/21 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | Wilton - 83 Staples - 103 | |
| Mon., 9/21 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:30 p.m. | L 2-3 | |
| Tue., 9/22 | V Boys Cross Country | St. Joseph, Ridgefield, New Canaan, Trinity Catholic | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Tue., 9/22 | V Girls Cross Country | St. Joseph, Ridgefield, New Canaan, Trinity Catholic | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/22 | V Field Hockey | St. Joseph | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 10-0 | |
| Tue., 9/22 | JV Field Hockey | St. Joseph | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | W 9-0 | |
| Thu., 9/24 | FR Football | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/24 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 6:00 p.m. | T 1-1 | |
| Thu., 9/24 | JV Boys Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:30 p.m. | L 0-2 | |
| Thu., 9/24 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | W 2-1 | |
| Thu., 9/24 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | L 0-1 | |
| Thu., 9/24 | FR Field Hockey | Greenwich | Home - Wilton HS - Grass Field [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/24 | V Girls Soccer | Fairfield Warde | Home - Lilly Field - Turf [Directions] | 7:00 p.m. | L 0-3 | |
| Thu., 9/24 | JV Girls Soccer | Fairfield Warde | Home - Allen's Field [Directions] | 4:15 p.m. | T 1-1 | |
| Thu., 9/24 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:30 p.m. | ||
| Fri., 9/25 | V Football | Staples | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 0-37 | Youth Football Night |
| Fri., 9/25 | FR Boys Soccer | Fairfield Ludlowe | Home - Allen's Field [Directions] | 4:15 p.m. | W 1-0 | |
| Fri., 9/25 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 4:30 p.m. | ||
| Fri., 9/25 | V Girls Volleyball | Bridgeport Central | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/25 | JV Girls Volleyball | Bridgeport Central | Home - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 2-0 | |
| Sat., 9/26 | V Girls Cross Country | Bethel | Away - Bethel HS [Directions] | 9:00 a.m. | ||
| Sat., 9/26 | V Field Hockey | Lakeland/Panas (NY) | Home - Fujitani Field - Turf [Directions] | 2:00 p.m. | L 0-4 | |
| Sat., 9/26 | JV Field Hockey | Lakeland/Panas (NY) | Home - Fujitani Field - Turf [Directions] | 12:00 p.m. | W 2-1 | |
| Sat., 9/26 | V Girls Soccer | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 12:00 p.m. | L 0-1 | |
| Sat., 9/26 | JV Girls Soccer | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 10:00 a.m. | W 1-0 | |
| Mon., 9/28 | V Boys Soccer | Ridgefield | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | T 2-2 | |
| Mon., 9/28 | JV Boys Soccer | Ridgefield | Home - Allen's Field [Directions] | 4:15 p.m. | L 1-2 | |
| Mon., 9/28 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | L 1-5 | |
| Mon., 9/28 | V Field Hockey | Staples | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 9/28 | JV Field Hockey | Staples | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 9/28 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 7-1 | |
| Mon., 9/28 | V Girls Swimming and Diving | Norwalk/McMahon | Home - New Canaan YMCA [Directions] | 3:30 p.m. | Wilton - 103 Norwalk - 80 | Diving Only |
| Mon., 9/28 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Mon., 9/28 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | W 2-1 | |
| Mon., 9/28 | FR Girls Volleyball | Greenwich | Home - Nicholas Zeioli Field House [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 9/29 | V Boys Cross Country | Norwalk, Darien, Trumbull | Home - Allen's Field [Directions] | 4:00 p.m. | Wilton 36 - Darien 25 Wilton 36 - Trumbull 25 Wilton 18 - Norwalk 43 | |
| Tue., 9/29 | JV Boys Soccer | Weston | Home - Lilly Field - Turf [Directions] | 5:00 p.m. | T 0-0 | |
| Tue., 9/29 | JV Boys Soccer | Weston | Home - Lilly Field - Turf [Directions] | 5:00 p.m. | ||
| Tue., 9/29 | V Girls Cross Country | Norwalk, Darien, Trumbull | Home - Allen's Field [Directions] | 4:00 p.m. | Wilton 24 - Darien 35 Wilton 19 - Trumbull 42 | |
| Tue., 9/29 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 0-1 | |
| Tue., 9/29 | JV Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 9/29 | FR Girls Soccer | Ridgefield | Home - Allen's Field [Directions] | 4:15 p.m. | ||
| Wed., 9/30 | V Boys Soccer | Trinity Catholic | Home - Wilton HS [Directions] | 4:30 p.m. | W 6-0 | |
| Wed., 9/30 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 9/30 | V Girls Volleyball | St. Joseph | Home - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 1-3 | |
| Wed., 9/30 | JV Girls Volleyball | St. Joseph | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-2 | |
| Wed., 9/30 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:15 p.m. | W 2-1 | |
| Thu., 10/1 | FR Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | ||
| Thu., 10/1 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:15 p.m. | L 0-2 | |
| Thu., 10/1 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | T 0-0 | |
| Thu., 10/1 | FR Field Hockey | Darien | Home - Wilton HS - Grass Field [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 10/1 | V Girls Soccer | Trinity Catholic | Home - Lilly Field - Turf [Directions] | 7:00 p.m. | W 9-0 | |
| Thu., 10/1 | FR Girls Soccer | Greenwich | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 10/2 | V Boys Soccer | Danbury | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 3-2 | Soccer Homecoming |
| Fri., 10/2 | JV Boys Soccer | Danbury | Home - Allen's Field [Directions] | 4:15 p.m. | W 4-3 | |
| Fri., 10/2 | FR Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | L 0-1 | |
| Fri., 10/2 | V Girls Cross Country | Nonnewaug | Away - Nonnewaug HS [Directions] | 4:00 p.m. | ||
| Fri., 10/2 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/2 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 10/2 | FR Girls Volleyball | Fairfield Warde | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 3-1 | |
| Sat., 10/3 | V Football | Fairfield Ludlowe | Home - Fujitani Field - Turf [Directions] | 2:30 p.m. | W 17-7 | Home Coming |
| Mon., 10/5 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | W 1-0 | |
| Mon., 10/5 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:30 p.m. | ||
| Mon., 10/5 | FR Girls Soccer | Danbury | Home - Allen's Field [Directions] | 4:15 p.m. | ||
| Mon., 10/5 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:45 p.m. | L 0-3 | |
| Mon., 10/5 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:30 p.m. | L 1-2 | |
| Tue., 10/6 | V Boys Cross Country | Fairfield Warde, Bridgeport Central, Brien McMahon | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:30 p.m. | L 0-1 | |
| Tue., 10/6 | JV Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 10/6 | FR Boys Soccer | Darien | Home - Allen's Field [Directions] | 4:15 p.m. | W 3-0 | |
| Tue., 10/6 | V Girls Cross Country | Fairfield Warde, Bridgeport Central, Brien McMahon | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Field Hockey | Stamford | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/7 | V Girls Soccer | Darien | Home - Lilly Field - Turf [Directions] | 6:30 p.m. | W 1-0 | |
| Wed., 10/7 | JV Girls Soccer | Darien | Home - Allen's Field [Directions] | 4:15 p.m. | ||
| Wed., 10/7 | FR Girls Soccer | Darien | Away - Middlesex Lower Field [Directions] | 4:30 p.m. | ||
| Wed., 10/7 | V Girls Volleyball | Ridgefield | Home - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 0-3 | |
| Wed., 10/7 | JV Girls Volleyball | Ridgefield | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 10/7 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:30 p.m. | L 1-3 | |
| Thu., 10/8 | FR Football | Fairfield Warde | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Thu., 10/8 | V Boys Soccer | Trumbull | Home - Lilly Field - Turf [Directions] | 7:00 p.m. | L 0-2 | |
| Thu., 10/8 | JV Boys Soccer | Trumbull | Home - Lilly Field - Turf [Directions] | 4:45 p.m. | W 3-1 | |
| Thu., 10/8 | FR Boys Soccer | Trumbull | Away - The Pit [Directions] | 4:30 p.m. | W 4-3 | |
| Thu., 10/8 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | W 5-0 | |
| Thu., 10/8 | JV Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | W 7-0 | |
| Thu., 10/8 | FR Field Hockey | Danbury | Home - Wilton HS - Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Girls Swimming and Diving | Danbury | Home - Wilton YMCA [Directions] | 3:00 p.m. | Wilton - 92 Danbury - 70 | |
| Fri., 10/9 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | T 1-1 | |
| Fri., 10/9 | JV Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:30 p.m. | ||
| Fri., 10/9 | FR Girls Soccer | Trumbull | Home - Allen's Field [Directions] | 4:15 p.m. | ||
| Fri., 10/9 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | L 0-3 | |
| Fri., 10/9 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Sat., 10/10 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 10:00 a.m. | L 7-19 | |
| Sat., 10/10 | V Field Hockey | Norwalk | Home - Fujitani Field - Turf [Directions] | 9:00 a.m. | W 2-0 | |
| Sat., 10/10 | JV Field Hockey | Norwalk | Home - Fujitani Field - Turf [Directions] | 10:30 a.m. | ||
| Sat., 10/10 | FR Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 12:00 p.m. | ||
| Mon., 10/12 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 10/12 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 10/12 | V Field Hockey | Mamaroneck (NY) | Home - Fujitani Field - Turf [Directions] | 11:00 a.m. | L 1-2 | |
| Mon., 10/12 | JV Field Hockey | Mamaroneck (NY) | Home - Fujitani Field - Turf [Directions] | 1:00 p.m. | L 0-2 | |
| Mon., 10/12 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | Wilton - 72 Greenwich - 103 | |
| Tue., 10/13 | V Boys Cross Country | Greenwich, Fairfield Ludlowe, Stamford | Away - Greenwich Point [Directions] | 4:00 p.m. | Wilton 35 - Ludlowe - 25 Wilton 30 - Greenwich 27 Wilton 21 - Stamford 38 | |
| Tue., 10/13 | FR Boys Soccer | Stamford | Home - Allen's Field [Directions] | 4:15 p.m. | W 2-0 | |
| Tue., 10/13 | V Girls Cross Country | Greenwich, Fairfield Ludlowe, Stamford | Away - Greenwich Point [Directions] | 4:00 p.m. | Wilton 20 - Ludlowe 41 Wilton 32 - Greenwich 25 Wilton 18 - Stamford 45 | |
| Tue., 10/13 | V Girls Soccer | Stamford | Home - Lilly Field - Turf [Directions] | 6:30 p.m. | W 6-0 | |
| Tue., 10/13 | JV Girls Soccer | Stamford | Home - Allen's Field [Directions] | 4:15 p.m. | W 8-1 | |
| Tue., 10/13 | V Girls Swimming and Diving | Fairfield Ludlowe, Fairfield Warde | Home - New Canaan YMCA [Directions] | 3:30 p.m. | Wilton 98 - Ludlowe - 69 | Diving Only |
| Tue., 10/13 | V Girls Volleyball | Danbury | Home - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 0-3 | |
| Tue., 10/13 | JV Girls Volleyball | Danbury | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-0 | |
| Tue., 10/13 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:30 p.m. | W 3-2 | |
| Wed., 10/14 | V Boys Soccer | Brien McMahon | Home - Lilly Field - Turf [Directions] | 4:15 p.m. | W 4-0 | |
| Wed., 10/14 | JV Boys Soccer | Brien McMahon | Home - Allen's Field [Directions] | 4:15 p.m. | W 2-1 | |
| Wed., 10/14 | V Field Hockey | Trumbull | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 10/14 | JV Field Hockey | Trumbull | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | W 4-1 | |
| Wed., 10/14 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 10/14 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 10/14 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | L 2-1 | |
| Wed., 10/14 | FR Girls Volleyball | Darien | Home - Cider Mill School [Directions] | 4:00 p.m. | L 3-0 | |
| Thu., 10/15 | FR Football | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 4-1 | |
| Thu., 10/15 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | W 6-0 | |
| Fri., 10/16 | V Football | St. Joseph | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 0-35 | |
| Fri., 10/16 | FR Boys Soccer | Staples | Home - Allen's Field [Directions] | 4:15 p.m. | L 0-3 | |
| Fri., 10/16 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 1-2 | |
| Fri., 10/16 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/16 | FR Field Hockey | New Canaan | Home - Wilton HS - Grass Field [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/16 | FR Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Fri., 10/16 | V Girls Swimming and Diving | Fairfield Warde | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Fri., 10/16 | V Girls Volleyball | Trumbull | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-3 | |
| Fri., 10/16 | JV Girls Volleyball | Trumbull | Home - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | ||
| Fri., 10/16 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:30 p.m. | L 1-3 | |
| Sat., 10/17 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 12:00 p.m. | W 2-1 | |
| Sat., 10/17 | JV Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | ||
| Sat., 10/17 | V Girls Soccer | Staples | Home - Lilly Field - Turf [Directions] | 11:00 a.m. | W 1-0 | |
| Mon., 10/19 | V Boys Soccer | New Canaan | Home - Lilly Field - Turf [Directions] | 6:30 p.m. | W 2-1 | Senior Night |
| Mon., 10/19 | JV Boys Soccer | New Canaan | Home - Allen's Field [Directions] | 4:15 p.m. | W 1-0 | |
| Mon., 10/19 | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:30 p.m. | T 0-0 | |
| Mon., 10/19 | FR Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | L 2-3 | |
| Mon., 10/19 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Mon., 10/19 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:30 p.m. | L 0-3 | |
| Mon., 10/19 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Mon., 10/19 | FR Girls Volleyball | Stamford | Home - Nicholas Zeoli Field House [Directions] | 4:15 p.m. | W 3-1 | |
| Tue., 10/20 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 10/20 | JV Field Hockey | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | 4:30 p.m. | ||
| Tue., 10/20 | FR Field Hockey | Fairfield Ludlowe | Home - Wilton HS - Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Girls Soccer | New Canaan | Away - Conner Field [Directions] | 4:30 p.m. | L 0-1 | |
| Tue., 10/20 | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:30 p.m. | L 0-1 | |
| Tue., 10/20 | FR Girls Soccer | New Canaan | Home - Allen's Field [Directions] | 4:15 p.m. | T 0-0 | |
| Wed., 10/21 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:15 p.m. | W 4-1 | |
| Wed., 10/21 | JV Boys Soccer | Westhill | Away - Rippowam Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/21 | FR Boys Soccer | Westhill | Home - Allen's Field [Directions] | 4:15 p.m. | L 0-1 | |
| Wed., 10/21 | V Girls Volleyball | Brien McMahon | Home - Nicholas Zeoli Field House [Directions] | 4:45 p.m. | L 0-3 | |
| Wed., 10/21 | JV Girls Volleyball | Brien McMahon | Home - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | ||
| Thu., 10/22 | FR Football | Stamford | Away - Fujitani Field - Turf [Directions] | 7:00 p.m. | ||
| Thu., 10/22 | V Field Hockey | Brien McMahon | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | W 6-0 | |
| Thu., 10/22 | JV Field Hockey | Brien McMahon | Home - Fujitani Field - Turf [Directions] | 4:00 p.m. | W 6-0 | |
| Thu., 10/22 | V Girls Soccer | Westhill | Home - Lilly Field - Turf [Directions] | 7:00 p.m. | W 3-2 | Senior Night |
| Thu., 10/22 | JV Girls Soccer | Westhill | Home - Allen's Field [Directions] | 4:15 p.m. | ||
| Thu., 10/22 | FR Girls Soccer | Fairfield Ludlowe | Home - Allen's Field [Directions] | 4:15 p.m. | ||
| Thu., 10/22 | V Girls Swimming and Diving | St. Joseph | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Fri., 10/23 | V Football | Stamford | Away - Stamford HS [Directions] | 6:30 p.m. | W 30-27 | |
| Fri., 10/23 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/23 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/23 | FR Girls Volleyball | Staples | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 10/24 | JV Football | Stamford | Away - Stamford HS [Directions] | Cancelled | Cancelled | |
| Mon., 10/26 | V Boys Soccer | Norwalk | Home - Lilly Field - Turf [Directions] | 4:15 p.m. | T 0-0 | |
| Mon., 10/26 | JV Boys Soccer | Norwalk | Home - Allen's Field [Directions] | 4:15 p.m. | ||
| Mon., 10/26 | FR Boys Soccer | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:30 p.m. | L 0-3 | |
| Mon., 10/26 | FR Field Hockey | Trumbull | Away - Indian Ledge Turf [Directions] | 6:00 p.m. | ||
| Mon., 10/26 | V Girls Volleyball | New Canaan | Home - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 0-3 | Senior Night |
| Mon., 10/26 | JV Girls Volleyball | New Canaan | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Mon., 10/26 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/27 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | W 4-0 | |
| Tue., 10/27 | JV Girls Soccer | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:30 p.m. | W 7-0 | |
| Wed., 10/28 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 10/28 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/28 | FR Field Hockey | Ridgefield | Home - Wilton HS - Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/28 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 2-3 | |
| Wed., 10/28 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 10/29 | FR Football | Darien | Away - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | V Boys Soccer | Greenwich | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | L 1-2 | |
| Thu., 10/29 | FR Girls Volleyball | Westhill | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | V Football | Darien | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 7-48 | |
| Fri., 10/30 | V Field Hockey | Playdowns | Away - TBA | TBA | ||
| Fri., 10/30 | V Field Hockey | Playdowns | Away - TBA | TBA | ||
| Fri., 10/30 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 3:30 p.m. | 1:45 bus | |
| Fri., 10/30 | V Girls Volleyball | Norwalk | Home - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/30 | JV Girls Volleyball | Norwalk | Home - Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Sat., 10/31 | V Girls Swimming and Diving | JV FCIACS | Away - Greenwich H.S. | 12:00 p.m. | ||
| Mon., 11/2 | V Girls Soccer | FCIAC Semi-Finals | Home - Lilly Field - Turf [Directions] | TBA | ||
| Tue., 11/3 | V Boys Soccer | Fairfield Warde (Scrim.) | Home - Lilly Field - Turf [Directions] | 3:30 p.m. | ||
| Tue., 11/3 | V Field Hockey | FCIAC Semi-Finals | Away - New Canaan H.S. | TBA | ||
| Tue., 11/3 | V Field Hockey | FCIAC Semi-Finals | Away - New Canaan H.S. | TBA | ||
| Tue., 11/3 | V Girls Swimming and Diving | FCIAC Trials | Away - Greenwich H.S. | 4:00 p.m. | ||
| Wed., 11/4 | V Boys Soccer | FCIAC FInals | Away | TBA | ||
| Wed., 11/4 | V Girls Soccer | Tournament Game - Opponent Not Known | Away - Norwalk H.S. | TBA | ||
| Wed., 11/4 | V Girls Swimming and Diving | FCIAC Diving | Away | 4:30 p.m. | ||
| Thu., 11/5 | V Field Hockey | FCIAC Finals | Away - Brien McMahon H.S. | TBA | ||
| Thu., 11/5 | V Field Hockey | FCIAC Finals | Away - Brien McMahon H.S. | TBA | ||
| Thu., 11/5 | V Girls Swimming and Diving | FCIAC Finals | Away - Greenwich H.S. | 4:00 p.m. | ||
| Fri., 11/6 | V Boys Soccer | Ridgefield (Scrim.) | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Fri., 11/6 | V Girls Soccer | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 5:00 p.m. | ||
| Mon., 11/9 | V Girls Soccer | Westhill | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 11/10 | V Boys Soccer | Shelton | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 11/12 | FR Football | Danbury | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Thu., 11/12 | V Boys Soccer | New Milford | Away - Brookfield HS [Directions] | 2:00 p.m. | W 2-1 | |
| Thu., 11/12 | V Girls Swimming and Diving | Class L Diving | Away | 5:30 p.m. | ||
| Fri., 11/13 | V Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 7:00 p.m. | W 20-17 (OT) | |
| Fri., 11/13 | V Field Hockey | Darien | Away [Directions] | 2:00 p.m. | ||
| Fri., 11/13 | V Girls Soccer | New Canaan | Home - Lilly Field - Turf [Directions] | 3:00 p.m. | ||
| Sat., 11/14 | V Boys Soccer | Farmington | Away - Tunxis Mead Park [Directions] | 4:30 p.m. | ||
| Sat., 11/14 | V Girls Swimming and Diving | Class L Swim Trials | Away - East Hartford H.S. | 5:55 p.m. | ||
| Wed., 11/18 | V Girls Swimming and Diving | Class L Swim Finals | Away - Wesleyan University | 7:00 p.m. | ||
| Thu., 11/19 | FR Football | Trinity Catholic | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Thu., 11/19 | V Girls Swimming and Diving | Diving Open | Away - Middletown H.S. | 5:25 p.m. | ||
| Sat., 11/21 | V Girls Swimming and Diving | STATE OPEN | Away - Yale University | 12:00 p.m. | ||
| Thu., 11/26 | V Football | Trinity Catholic | Home - Wilton HS [Directions] | 10:30 a.m. | L 14-41 | |
| Sat., 12/5 | V Girls Ice Hockey | FCIAC Jamboree | Away | 4:30 p.m. | Shelton Rinks | |
| Wed., 12/9 | V Boys Ice Hockey | New Fairfield (Scrim.) | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | ||
| Wed., 12/9 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 4:15 p.m. | L 0-2 | Milford Ice Pavilion |
| Thu., 12/10 | V Boys Basketball | Immaculate (Scrim.) | Away - Immaculate HS [Directions] | 6:00 p.m. | ||
| Sat., 12/12 | V Boys Ice Hockey | Shelton Jamboree | Away | 5:15 p.m. | ||
| Sat., 12/12 | V Wrestling | Joel Barlow (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 12/12 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown HS Gymnasium [Directions] | 8:30 a.m. | ||
| Sat., 12/12 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | 12:00 p.m. | L 1-4 | Bennet Ice Rink - West Haven |
| Mon., 12/14 | V Boys Basketball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 12/15 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - So No Icehouse - Norwalk [Directions] | 8:50 p.m. | L 1-5 | |
| Wed., 12/16 | V Boys Ice Hockey | New Fairfield (Scrim.) | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | ||
| Wed., 12/16 | V Wrestling | Stamford | Away - Stamford HS [Directions] | 6:00 p.m. | ||
| Thu., 12/17 | V Boys Basketball | New Fairfield (Scrim.) | Home - Nicholas Zeoli Field House [Directions] | 5:00 p.m. | ||
| Thu., 12/17 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 4:00 p.m. | L 2-3 | Non-League |
| Fri., 12/18 | V Girls Basketball | New Milford | Away - New Milford HS [Directions] | 5:00 p.m. | W 59-18 | |
| Sat., 12/19 | V Boys Indoor Track | Reindeer Relays | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 12/19 | V Wrestling | Guilford | Away [Directions] | 9:00 a.m. | ||
| Sat., 12/19 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | 6:45 p.m. | L 1-4 | Rinks @ Shelton |
| Sat., 12/19 | V Girls Indoor Track | Reindeer Relays | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Mon., 12/21 | V Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 7:00 p.m. | L 58-71 | |
| Mon., 12/21 | JV Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | FR Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/21 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Winter Garden Rink-Ridgefield [Directions] | 5:10 p.m. | L 4-5(OT) | |
| Mon., 12/21 | V Girls Basketball | Westhill | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 59-29 | |
| Mon., 12/21 | JV Girls Basketball | Westhill | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | FR Girls Basketball | Westhill | Home - Nicholas Zeoli Field House [Directions] | Cancelled | Cancelled | |
| Mon., 12/21 | JV Girls Ice Hockey | Notre Dame-Fairfield | Home - Stamford Twin Rinks [Directions] | 3:00 p.m. | ||
| Tue., 12/22 | V Wrestling | Fairfield Warde | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 12/22 | V Wrestling | Bethel | Home - Nicholas Zeoli Field House [Directions] | 5:00 p.m. | ||
| Wed., 12/23 | V Boys Basketball | Masuk | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 67-54 | |
| Wed., 12/23 | JV Boys Basketball | Masuk | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 12/23 | FR Boys Basketball | Masuk | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 12/23 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 6:00 p.m. | L 2-11 | |
| Wed., 12/23 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:30 p.m. | W 46-35 | |
| Wed., 12/23 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 3:00 p.m. | ||
| Wed., 12/23 | V Girls Ice Hockey | Darien | Home - So No Icehouse - Norwalk [Directions] | 8:00 p.m. | L 0-10 | |
| Mon., 12/28 | V Boys Basketball | Staples | Home - Newtown HS [Directions] | 4:00 p.m. | W 57-56 | @ Newtown HS |
| Mon., 12/28 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 7:10 p.m. | L 0-8 | |
| Mon., 12/28 | V Girls Basketball | Scarsdale (NY) | Home - Stamford HS [Directions] | 3:00 p.m. | L 58-51 | @ Stamford HS |
| Wed., 12/30 | V Boys Basketball | Kolbe Cathedral | Away - Newtown HS [Directions] | 6:00 p.m. | W 69-53 | |
| Wed., 12/30 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 12/30 | JV Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | Cancelled | Cancelled | |
| Wed., 12/30 | V Boys Indoor Track | FCIAC Qualifier | Home - Nicholas Zeoli Field House [Directions] | 10:00 a.m. | NC, Danbury, Trumbull, Darien, Westhill, F. Warde, Norwalk | |
| Wed., 12/30 | V Wrestling | McDougall Duals | Away - Trumbull HS [Directions] | 9:00 a.m. | ||
| Wed., 12/30 | V Girls Basketball | Westhill | Away - Stamford HS [Directions] | 3:00 p.m. | L 26-33 | |
| Wed., 12/30 | V Girls Ice Hockey | New Canaan | Home - So No Icehouse - Norwalk [Directions] | 5:00 p.m. | L 0-8 | |
| Wed., 12/30 | V Girls Indoor Track | FCIAC Qualifier | Home - Nicholas Zeoli Field House [Directions] | 10:00 a.m. | NC, Danbury, Trumbull, Darien, Westhill, F. Warde, Norwalk | |
| Sat., 1/2 | V Boys Ice Hockey | Amity | Home - Winter Garden Rink-Ridgefield [Directions] | 8:50 p.m. | L 3-5 | |
| Sat., 1/2 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 8:30 p.m. | L 0-4 | |
| Mon., 1/4 | JV Boys Ice Hockey | Staples | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Mon., 1/4 | V Boys Indoor Track | Tournament Game - Opponent Not Known | Away - Hillhouse | 4:00 p.m. | ||
| Mon., 1/4 | V Girls Indoor Track | Tournament Game - Opponent Not Known | Away - Hillhouse | 4:00 p.m. | ||
| Wed., 1/6 | V Boys Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Brunswick, SL, LH, Darien, Fairfield, New Canaan | |
| Wed., 1/6 | V Boys Ice Hockey | John Jay (NY) | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 0-5 | |
| Wed., 1/6 | V Wrestling | Brien McMahon | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 1/6 | V Girls Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Brunswick, SL, LH, Darien, Fairfield, New Canaan | |
| Wed., 1/6 | V Girls Ice Hockey | Lauralton Hall | Home - So No Icehouse - Norwalk [Directions] | 8:00 p.m. | W 5-1 | |
| Fri., 1/8 | V Boys Basketball | Bridgeport Central | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 93-60 | |
| Fri., 1/8 | JV Boys Basketball | Bridgeport Central | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Boys Basketball | Bridgeport Central | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | V Boys Ice Hockey | Danbury | Away - Danbury Ice Arena [Directions] | 7:50 p.m. | T 3-3 | |
| Fri., 1/8 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | Wilton 102-Trumbull 52 | |
| Fri., 1/8 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 48-13 | |
| Fri., 1/8 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/9 | V Boys Indoor Track | Developmental | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | New Canaan, F. Ludlowe, Ridgefield, Danbury, F. Warde, Stamford, Norwalk | |
| Sat., 1/9 | V Wrestling | Fairfield Warde Tournament | Away | 9:00 a.m. | ||
| Sat., 1/9 | V Competitive Cheerleading | 2016 Spirit Spectacular | Away - Oxford HS | Cancelled | Cancelled | |
| Sat., 1/9 | V Girls Gymnastics | Trumbull | Away - Next Dimension [Directions] | 6:00 p.m. | 129.5 | |
| Sat., 1/9 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 4:30 p.m. | L 1-4 | |
| Sat., 1/9 | V Girls Indoor Track | Developmental | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | New Canaan, F. Ludlowe, Ridgefield, Danbury, F. Warde, Stamford, Norwalk | |
| Mon., 1/11 | V Boys Ice Hockey | Milford Coop | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 1/12 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | W 55-51 | |
| Tue., 1/12 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/12 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/12 | V Girls Basketball | Greenwich | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 55-66 | |
| Tue., 1/12 | JV Girls Basketball | Greenwich | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/12 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | 7:00 p.m. | 131.2 | @ GCA |
| Wed., 1/13 | V Boys Ice Hockey | Trumbull | Home - Winter Garden Rink-Ridgefield [Directions] | 6:40 p.m. | L 2-3(OT) | |
| Wed., 1/13 | V Wrestling | Harding/Bassick/Bridgeport Central | Away - Harding-Auxiliary Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/13 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Rink-Ridgefield [Directions] | 8:50 p.m. | L 0-7 | |
| Thu., 1/14 | V Girls Gymnastics | Staples | Home - Wilton HS Aux. Gym [Directions] | 4:00 p.m. | 130.5 | |
| Fri., 1/15 | V Boys Basketball | St. Joseph | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 64-55 | |
| Fri., 1/15 | JV Boys Basketball | St. Joseph | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/15 | FR Boys Basketball | St. Joseph | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | JV Boys Ice Hockey | Newtown/New Fairfield (Scrim.) | Away - Danbury Ice Arena [Directions] | 3:40 p.m. | ||
| Fri., 1/15 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | Wilton - 109 Norwalk - 69 | |
| Fri., 1/15 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | L 27-30 | |
| Fri., 1/15 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ||
| Fri., 1/15 | JV Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | 4:15 p.m. | ||
| Sat., 1/16 | V Boys Ice Hockey | St. Joseph | Home - Winter Garden Rink-Ridgefield [Directions] | 8:50 p.m. | L 1-6 | |
| Sat., 1/16 | V Boys Indoor Track | Developmental | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | B. Central, Danbury, St. Joe's, B. McMahon, F. Ludlowe, Darien | |
| Sat., 1/16 | V Boys Indoor Track | Tournament Game - Opponent Not Known | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/16 | V Wrestling | Daniel Hand Duals | Away | 9:00 a.m. | ||
| Sat., 1/16 | V Competitive Cheerleading | 2016 Wildcat Open | Away - Seymour HS | TBA | ||
| Sat., 1/16 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | 6:00 p.m. | L 0-2 | |
| Sat., 1/16 | V Girls Indoor Track | Developmental | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | B. Central, Danbury, St. Joe's, B. McMahon, F. Ludlowe, Darien | |
| Sat., 1/16 | V Girls Indoor Track | Tournament Game - Opponent Not Known | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Mon., 1/18 | V Boys Ice Hockey | Norwalk | Home - Winter Garden Rink-Ridgefield [Directions] | 3:10 p.m. | L 1-2(OT) | |
| Mon., 1/18 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 4:00 p.m. | 133.3 | |
| Mon., 1/18 | JV Girls Ice Hockey | New Canaan | Home - Terry Connors Ice Rink [Directions] | 12:00 p.m. | ||
| Tue., 1/19 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 78-84(OT) | |
| Tue., 1/19 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/19 | V Wrestling | Norwalk | Away - Norwalk High Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/19 | V Girls Basketball | Fairfield Warde | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 33-45 | |
| Tue., 1/19 | JV Girls Basketball | Fairfield Warde | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 1/20 | V Girls Ice Hockey | Greenwich | Home [Directions] | 8:00 p.m. | L 1-6 | |
| Fri., 1/22 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 3:30 p.m. | L 52-59 | |
| Fri., 1/22 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/22 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | V Boys Ice Hockey | Ridgefield | Home - Winter Garden Rink-Ridgefield [Directions] | 3:00 p.m. | L 1-10 | |
| Fri., 1/22 | V Boys Swimming and Diving | Greenwich | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 521 Greenwich 118 | |
| Fri., 1/22 | V Girls Basketball | Fairfield Ludlowe | Home - Nicholas Zeoli Field House [Directions] | 2:00 p.m. | W 54-41 | |
| Fri., 1/22 | JV Girls Basketball | Fairfield Ludlowe | Home - Nicholas Zeoli Field House [Directions] | 3:30 p.m. | ||
| Sat., 1/23 | V Boys Indoor Track | Developmental | Home - Nicholas Zeoli Field House [Directions] | Cancelled | Cancelled | New Canaan, F. Ludlowe, Darien, Ridgefield, McMahon, Trumbull, F. Warde |
| Sat., 1/23 | V Wrestling | Silver City Duals | Away - Platt HS | Cancelled | Cancelled | Platt High School, Meriden, CT |
| Sat., 1/23 | V Girls Indoor Track | Developmental | Home [Directions] | Cancelled | Cancelled | New Canaan, F. Ludlowe, Darien, Ridgefield, McMahon, Trumbull, F. Warde |
| Mon., 1/25 | V Girls Basketball | Norwich Free Academy | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 34-35 | |
| Mon., 1/25 | JV Girls Basketball | Norwich Free Academy | Home - Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Tue., 1/26 | V Boys Basketball | Ridgefield | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 51-39 | |
| Tue., 1/26 | JV Boys Basketball | Ridgefield | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/26 | FR Boys Basketball | Ridgefield | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/26 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 43-61 | |
| Tue., 1/26 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/26 | V Girls Gymnastics | Darien | Home - Wilton HS Aux. Gym [Directions] | 5:00 p.m. | 130.8 | |
| Wed., 1/27 | V Boys Alpine Skiing | Ski Race | Away | 4:15 p.m. | Pomperaug, Gilbert, Farmington, Staples, CA | |
| Wed., 1/27 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 0-7 | |
| Wed., 1/27 | V Wrestling | Ridgefield | Home - Nicholas Zeoli Field House [Directions] | 5:00 p.m. | ||
| Wed., 1/27 | V Girls Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Pomperaug, Gilbert, Farmington, Staples, CA | |
| Wed., 1/27 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:10 p.m. | L 0-9 | |
| Thu., 1/28 | V Boys Indoor Track | Tournament Game - Opponent Not Known | Home - Nicholas Zeoli Field House [Directions] | 5:00 p.m. | New Canaan, FFLD. Ludlow, Darien, Ridgefield, McMahon, Trumbull, FFLD. Warde | |
| Thu., 1/28 | V Girls Indoor Track | Tournament Game - Opponent Not Known | Home - Nicholas Zeoli Field House [Directions] | 5:00 p.m. | New Canaan, FFLD. Ludlow, Darien, Ridgefield, McMahon, Trumbull, FFLD. Warde | |
| Fri., 1/29 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | W 54-49 | |
| Fri., 1/29 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Fri., 1/29 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | ||
| Fri., 1/29 | V Boys Swimming and Diving | New Canaan | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 100 Danbury 64 | |
| Fri., 1/29 | V Girls Basketball | Trinity Catholic | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 51-27 | Senior Night |
| Fri., 1/29 | JV Girls Basketball | Trinity Catholic | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/29 | V Girls Gymnastics | Joel Barlow | Away - Wilton YMCA [Directions] | 6:30 p.m. | 127.35 | |
| Sat., 1/30 | V Boys Indoor Track | Eastern FCIAC Divisional Championships | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/30 | V Boys Swimming and Diving | Danbury | Home - Wilton YMCA [Directions] | 1:00 p.m. | Wilton - 100 Danbury- 64 | |
| Sat., 1/30 | V Wrestling | Ridgefield Tournament | Away | 10:00 a.m. | ||
| Sat., 1/30 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - So No Icehouse - Norwalk [Directions] | 8:50 p.m. | W 3-1 | |
| Sat., 1/30 | V Girls Indoor Track | Eastern FCIAC Divisional Championships | Home - Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Mon., 2/1 | V Boys Alpine Skiing | State Shoot Invitational | Away - Mt. Southington | TBA | ||
| Mon., 2/1 | V Boys Basketball | Danbury | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 50-69 | |
| Mon., 2/1 | JV Boys Basketball | Danbury | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Mon., 2/1 | FR Boys Basketball | Danbury | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 2/1 | JV Boys Ice Hockey | Milford Coop | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Mon., 2/1 | V Girls Alpine Skiing | State Shoot Out | Away | TBA | ||
| Mon., 2/1 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 6:00 p.m. | W 48-28 | |
| Mon., 2/1 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:30 p.m. | ||
| Mon., 2/1 | V Girls Gymnastics | New Canaan | Home - Wilton HS Aux. Gym [Directions] | 4:00 p.m. | 137.0 | Senior Night |
| Tue., 2/2 | V Wrestling | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/3 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | W 57-48 | |
| Wed., 2/3 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/3 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/3 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:10 p.m. | L 1-8 | |
| Wed., 2/3 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | Wilton - 74 Darien - 111 | |
| Wed., 2/3 | V Girls Basketball | Darien | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 35-30 | |
| Wed., 2/3 | JV Girls Basketball | Darien | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/3 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Home - Longshore Rink [Directions] | Cancelled | Cancelled | |
| Thu., 2/4 | V Boys Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Danbury, Ridgefield, Hand, Greensich, Weston, Guilford, Southington | |
| Thu., 2/4 | V Boys Indoor Track | FCIAC Championships | Away - Hillhouse | TBA | @ Hillhouse HS | |
| Thu., 2/4 | V Girls Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | ||
| Thu., 2/4 | V Girls Indoor Track | FCIAC Championships | Away - Hillhouse | TBA | ||
| Sat., 2/6 | V Wrestling | New Fairfield Duels | Away - New Fairfield HS | 8:00 a.m. | ||
| Sat., 2/6 | V Competitive Cheerleading | FCIAC Championships | Home - Nicholas Zeoli Field House [Directions] | 10:30 a.m. | ||
| Sat., 2/6 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 1:30 p.m. | L 27-35 | |
| Sat., 2/6 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/6 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - So No Icehouse - Norwalk [Directions] | 2:10 p.m. | W 4-1 | Senior Night |
| Sun., 2/7 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 4:20 p.m. | L 1-8 | |
| Mon., 2/8 | V Boys Alpine Skiing | State Shoot-Out | Away - Mt. Southington | TBA | ||
| Mon., 2/8 | V Girls Alpine Skiing | State Shoot Out | Away | TBA | ||
| Tue., 2/9 | V Wrestling | Darien | Home - Nicholas Zeoli Field House [Directions] | 6:00 p.m. | Senior Night | |
| Tue., 2/9 | FR Girls Basketball | Stamford | Home - Nicholas Zeoli Field House [Directions] | Cancelled | Cancelled | |
| Wed., 2/10 | V Boys Ice Hockey | Darien | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 0-4 | |
| Wed., 2/10 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 99 Fairfield - 69 | |
| Wed., 2/10 | V Girls Basketball | Stamford | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 28-57 | |
| Wed., 2/10 | JV Girls Basketball | Stamford | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/10 | V Girls Gymnastics | Westhill | Home - Wilton HS Aux. Gym [Directions] | 4:00 p.m. | 130.85 | |
| Thu., 2/11 | V Boys Basketball | Trumbull | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 58-66 | |
| Thu., 2/11 | JV Boys Basketball | Trumbull | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Thu., 2/11 | FR Boys Basketball | Trumbull | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Boys Basketball | Brien McMahon | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 65-48 | |
| Fri., 2/12 | JV Boys Basketball | Brien McMahon | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Boys Basketball | Brien McMahon | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Boys Ice Hockey | Trinity Catholic | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | W 7-2 | |
| Fri., 2/12 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 56-29 | |
| Fri., 2/12 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | JV Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | 4:15 p.m. | ||
| Sat., 2/13 | V Boys Indoor Track | Class L Championship | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 2/13 | V Girls Gymnastics | FCIAC Championship | Away | 10:30 a.m. | 133.6 | @ Jonathan Law HS |
| Sat., 2/13 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - So No Icehouse - Norwalk [Directions] | 8:50 p.m. | L 0-4 | |
| Sat., 2/13 | V Girls Indoor Track | Class L Championship | Away | 10:00 a.m. | ||
| Mon., 2/15 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 12:00 p.m. | L 65-73 | |
| Mon., 2/15 | V Girls Basketball | Staples | Home - Nicholas Zeoli Field House [Directions] | 12:00 p.m. | W 40-30 | |
| Mon., 2/15 | JV Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 9:40 a.m. | ||
| Wed., 2/17 | V Boys Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Amity, Hopkins, Westhill, Litchfield, Prep | |
| Wed., 2/17 | V Boys Basketball | New Canaan | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 62-47 | |
| Wed., 2/17 | JV Boys Basketball | New Canaan | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/17 | FR Boys Basketball | New Canaan | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 1-4 | Senior Night |
| Wed., 2/17 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | Wilton - 87 Staples - 99 | |
| Wed., 2/17 | V Girls Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Amity, Hopkins, Westhill, Litchfield, Prep | |
| Wed., 2/17 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | W 42-30 | |
| Wed., 2/17 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/17 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Away [Directions] | TBA | ||
| Thu., 2/18 | V Girls Gymnastics | New Milford, Fairfield Ludlowe | Away - New Milford HS [Directions] | 5:00 p.m. | 138.8 | |
| Fri., 2/19 | V Boys Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 54-62 | |
| Fri., 2/19 | JV Boys Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | ||
| Fri., 2/19 | FR Boys Basketball | Stamford | Away - Stamford HS [Directions] | Cancelled | Cancelled | |
| Fri., 2/19 | V Boys Swimming and Diving | Ridgefield | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton- 86 Ridgefield - 94 | Senior Night |
| Fri., 2/19 | V Wrestling | Bristol Central | Away - Bristol Central HS [Directions] | 2:30 p.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | 7:30 p.m. | L 2-4 | |
| Sat., 2/20 | V Boys Indoor Track | CIAC OPEN | Away - TBA | 12:00 p.m. | ||
| Sat., 2/20 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 10:30 a.m.. | Wilton - 103 Westhill/Stamford - 82 | |
| Sat., 2/20 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 28-51 | |
| Sat., 2/20 | V Girls Ice Hockey | Hall/Conard | Home - So No Icehouse - Norwalk [Directions] | 7:10 p.m. | L 0-4 | |
| Sat., 2/20 | V Girls Indoor Track | CIAC OPEN | Away - TBA | 12:00 p.m. | ||
| Mon., 2/22 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 63-54 | |
| Mon., 2/22 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/22 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/22 | V Boys Swimming and Diving | FCIAC Trials | Away - Greenwich | 3:00 p.m. | ||
| Tue., 2/23 | V Boys Alpine Skiing | Race | Away - Mt. Southington | TBA | ||
| Wed., 2/24 | V Boys Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Cheshire, Barlow, Westbrook, Glastonbury | |
| Wed., 2/24 | V Boys Basketball | Norwalk | Home - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 76-53 | Senior Night |
| Wed., 2/24 | JV Boys Basketball | Norwalk | Home - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/24 | FR Boys Basketball | Norwalk | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Boys Ice Hockey | Greenwich | Home - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 0-5 | |
| Wed., 2/24 | V Girls Alpine Skiing | Ski Race | Away - Mt. Southington | 4:15 p.m. | Cheshire, Barlow, Westbrook Glastonbury | |
| Thu., 2/25 | V Boys Swimming and Diving | FCIAC Finals | Away - Greenwich | 5:00 p.m. | 6th place | |
| Fri., 2/26 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Sat., 2/27 | V Boys Basketball | Fairfield Ludlowe | Away - Ludlow HS [Directions] | 5:00 p.m. | ||
| Sat., 2/27 | V Competitive Cheerleading | NECA | Away - TBA | TBA | ||
| Sat., 2/27 | V Girls Basketball | Kennedy | Away - Kennedy HS [Directions] | 7:00 p.m. | ||
| Sat., 2/27 | V Girls Gymnastics | States | Away - TBA | TBA | States | |
| Tue., 3/1 | V Boys Basketball | Danbury | Away - Fairfield Warde HS [Directions] | 6:30 p.m. | ||
| Tue., 3/1 | V Boys Basketball | Danbury | Away - Fairfield Warde HS [Directions] | 6:30 p.m. | ||
| Tue., 3/1 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 6:30 p.m. | W 4-1 | |
| Tue., 3/1 | V Girls Gymnastics | State Open | Away - TBA | TBA | State Open | |
| Thu., 3/3 | V Girls Basketball | Norwich Free Academy | Away - Alumni Gym [Directions] | 5:00 p.m. | ||
| Thu., 3/24 | V Baseball | Immaculate (Scrim.) | Home [Directions] | 4:15 p.m. | ||
| Thu., 3/24 | JV Baseball | Immaculate (Scrim.) | Home - JV Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 3/26 | V Boys Lacrosse | New Fairfield (Scrim.) | Away [Directions] | TBA | ||
| Sat., 3/26 | V Girls Lacrosse | Wilton Playday | Home - Lilly Field - Turf [Directions] | TBA | ||
| Sat., 3/26 | V Softball | Bristol Central (Scrim.) | Home - WHS Varsity Softball Field [Directions] | 10:30 a.m. | ||
| Tue., 3/29 | V Baseball | Darien (Scrim.) | Away - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | ||
| Tue., 3/29 | JV Baseball | Darien (Scrim.) | Away - DHS Baseball JV Field [Directions] | 4:30 p.m. | ||
| Tue., 3/29 | V Boys Tennis | Weston (Scrim.) | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Softball | Westhill (Scrim.) | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Girls Tennis | Weston (Scrim.) | Away - WHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | Bullard Havens Tech (Scrim.) | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 3/30 | V Softball | Bethel (Scrim.) | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale M.S. Upper [Directions] | 4:30 p.m. | ||
| Thu., 3/31 | V Boys Tennis | St. Lukes (Scrim.) | Home - Wilton Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 3/31 | V Softball | Immaculate (Scrim.) | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Fordham Prep (NY) (Scrim.) | Home [Directions] | 12:00 p.m. | ||
| Sat., 4/2 | JV Boys Lacrosse | Fordham Prep (NY) | Home - Whitten Field [Directions] | 12:00 p.m. | ||
| Sat., 4/2 | V Girls Lacrosse | Glastonbury | Home - Lilly Field - Turf [Directions] | 11:00 a.m. | W 11-8 | |
| Sat., 4/2 | JV Girls Lacrosse | Glastonbury | Home - Lilly Field - Turf [Directions] | 12:15 p.m. | ||
| Tue., 4/5 | V Baseball | Brookfield | Home - WHS Varsity Baseball Field [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 4/5 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | W 17-2 | |
| Tue., 4/5 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/5 | V Boys Outdoor Track | Weston | Home - WHS Track [Directions] | Cancelled | Cancelled | |
| Tue., 4/5 | V Girls Lacrosse | Ridgefield | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | L 7-8 | |
| Tue., 4/5 | JV Girls Lacrosse | Ridgefield | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Baseball | HMTCA/SMSA | Home - WHS Varsity Baseball Field [Directions] | 5:00 p.m. | W 19-1 | |
| Wed., 4/6 | V Girls Golf | New Canaan | Home - Silver Mine CC [Directions] | 3:30 p.m. | Wilton 174 New Canaan 165 | |
| Wed., 4/6 | FR Girls Lacrosse | Norwalk | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Girls Outdoor Track | Westhill | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Softball | New Fairfield | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | W 9-2 | |
| Fri., 4/8 | V Baseball | Weston | Home - Wilton HS [Directions] | 4:30 p.m. | W 5-2 | |
| Fri., 4/8 | FR Baseball | Weston | Home - JV Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 4/8 | FR Boys Lacrosse | Darien | Home - Allen's Field [Directions] | 4:30 p.m. | ||
| Fri., 4/8 | V Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Fri., 4/8 | FR Girls Lacrosse | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Softball | Weston | Away - Hurlbutt El. School, Weston [Directions] | 4:00 p.m. | W 11-1 | |
| Fri., 4/8 | V Girls Tennis | Bridgeport Central | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/8 | V Girls Tennis | Weston | Home - Wilton Tennis Courts [Directions] | 5:00 p.m. | W 4-3 | |
| Sat., 4/9 | V Baseball | Cheshire | Home - WHS Varsity Baseball Field [Directions] | 12:00 p.m. | L 1-7 | |
| Sat., 4/9 | FR Baseball | Cheshire | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 4/9 | V Boys Lacrosse | Fairfield Prep | Home - Fujitani Field - Turf [Directions] | 2:30 p.m. | W 16-6 | |
| Sat., 4/9 | JV Boys Lacrosse | Fairfield Prep | Home - Whitten Field [Directions] | 2:30 p.m. | ||
| Mon., 4/11 | JV Baseball | Cheshire | Away - Cheshire High Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Greenwich | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 4/11 | V Softball | Immaculate | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | W 6-2 | |
| Mon., 4/11 | V Girls Tennis | Greenwich | Home - Wilton Tennis Courts [Directions] | 1:00 p.m. | W 4-3 | |
| Tue., 4/12 | V Boys Lacrosse | New Canaan | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | L 2-11 | |
| Tue., 4/12 | JV Boys Lacrosse | New Canaan | Home - Whitten Field [Directions] | 5:00 p.m. | ||
| Tue., 4/12 | FR Boys Lacrosse | Greenwich | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 15-0 | |
| Tue., 4/12 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 4/13 | V Baseball | Bridgeport Central | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | W 14-0 | |
| Wed., 4/13 | JV Baseball | Bridgeport Central | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/13 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | 4:30 p.m. | W 12-3 | |
| Thu., 4/14 | FR Girls Lacrosse | Fairfield Warde | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 4/15 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 2:00 p.m. | L 1-3 | |
| Fri., 4/15 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 2:00 p.m. | ||
| Fri., 4/15 | FR Baseball | Greenwich | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 2:30 p.m. | ||
| Fri., 4/15 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 3:30 p.m. | L 10-12 | |
| Fri., 4/15 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 2:00 p.m. | ||
| Fri., 4/15 | V Softball | Greenwich | Home - WHS Varsity Softball Field [Directions] | 3:00 p.m. | W 7-1 | |
| Sat., 4/16 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 11:30 a.m. | L 11-12(OT) | |
| Sat., 4/16 | JV Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Mon., 4/18 | V Baseball | St. Joseph | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 2-3 | |
| Mon., 4/18 | JV Baseball | St. Joseph | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/18 | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Golf | Fairfield Warde | Home - Rolling Hills CC [Directions] | 3:30 p.m. | Wilton 183 Warde 197 | |
| Mon., 4/18 | JV Boys Golf | Fairfield Warde | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 4/18 | JV Boys Golf | Fairfield Warde | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 4/18 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | W 18-6 | |
| Mon., 4/18 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 4/18 | FR Boys Lacrosse | Newtown | Home - Allen's Field [Directions] | Cancelled | Cancelled | |
| Mon., 4/18 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 4/18 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | 4:30 p.m. | L 0-9 | |
| Mon., 4/18 | V Girls Tennis | Fairfield Warde | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 4/18 | JV Girls Tennis | Fairfield Warde | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | JV Boys Golf | Greenwich | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Tue., 4/19 | JV Boys Golf | Greenwich | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Tue., 4/19 | V Boys Outdoor Track | Fairfield Ludlowe | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | V Boys Tennis | Fairfield Ludlowe | Away - FLHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 4/19 | V Girls Golf | Greenwich | Home - Silver Mine CC [Directions] | 3:30 p.m. | Greenwich 168 Wilton 182 | |
| Tue., 4/19 | V Girls Lacrosse | New Canaan | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | L 10-14 | |
| Tue., 4/19 | JV Girls Lacrosse | New Canaan | Home - Lilly Field - Turf [Directions] | 4:30 p.m. | ||
| Tue., 4/19 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | V Girls Tennis | Fairfield Ludlowe | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 4/19 | JV Girls Tennis | Fairfield Ludlowe | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:30 p.m. | W 9-3 | |
| Wed., 4/20 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:30 p.m. | ||
| Wed., 4/20 | FR Baseball | Fairfield Warde | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Boys Golf | Westhill | Away - Hubbard Brennan Golf Course [Directions] | 3:15 p.m. | Wilton 181 Westhill 164 | |
| Wed., 4/20 | V Boys Lacrosse | Glastonbury | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 17-6 | |
| Wed., 4/20 | JV Boys Lacrosse | Glastonbury | Home - Fujitani Field - Turf [Directions] | 5:00 p.m. | ||
| Wed., 4/20 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 4/20 | V Softball | Fairfield Warde | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | W 8-3 | |
| Thu., 4/21 | V Boys Tennis | Ridgefield | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/21 | V Girls Golf | Fairfield Warde | Home - Silver Mine CC [Directions] | 3:30 p.m. | Wilton 173 Warde 160 | |
| Thu., 4/21 | V Girls Lacrosse | Danbury | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 14-8 | |
| Thu., 4/21 | JV Girls Lacrosse | Danbury | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Girls Outdoor Track | Fairfield Ludlowe | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Fri., 4/22 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:30 p.m. | L 2-4 | |
| Fri., 4/22 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Baseball | Fairfield Ludlowe | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Boys Lacrosse | Darien | Away - DHS Field #1 -Turf [Directions] | 4:30 p.m. | ||
| Fri., 4/22 | FR Girls Lacrosse | Darien | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Softball | Fairfield Ludlowe | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | L 1-4 | |
| Fri., 4/22 | JV Softball | Fairfield Ludlowe | Home - JV Softball Field [Directions] | Cancelled | Cancelled | |
| Sat., 4/23 | JV Baseball | Weston | Away - Revson Field, Weston [Directions] | 10:00 a.m. | ||
| Sat., 4/23 | V Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 1:00 p.m. | L 3-17 | |
| Sat., 4/23 | JV Boys Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 10:30 a.m. | ||
| Sat., 4/23 | V Softball | Brookfield | Away - BHS Softball Field [Directions] | 10:00 a.m. | L 1-2 | |
| Mon., 4/25 | V Baseball | Ridgefield | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | W 4-3 | |
| Mon., 4/25 | JV Baseball | Ridgefield | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/25 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Golf | Darien | Home - Rolling Hills CC [Directions] | 3:30 p.m. | Wilton - 179 Darien - 148 | |
| Mon., 4/25 | JV Boys Golf | Darien | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 4/25 | JV Boys Golf | Darien | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 4/25 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| Mon., 4/25 | V Boys Outdoor Track | Norwalk, Darien | Away - Testa Field, NHS [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | W 7-0 | |
| Mon., 4/25 | FR Girls Lacrosse | Weston | Home - Allen's Field [Directions] | 5:15 p.m. | ||
| Mon., 4/25 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:15 p.m. | L 2-11 | |
| Mon., 4/25 | V Girls Tennis | Trinity Catholic | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/26 | V Boys Lacrosse | Westhill | Home - Fujitani Field - Turf [Directions] | 5:30 p.m. | W 18-0 | |
| Tue., 4/26 | JV Boys Lacrosse | Westhill | Home - Whitten Field [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:30 p.m. | Wilton - 190 Ridgefield - 215 | |
| Tue., 4/26 | V Girls Lacrosse | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 13-11 | |
| Tue., 4/26 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Baseball | Trinity Catholic | Away - Cubeta Stadium | 4:30 p.m. | W 6-0 | |
| Wed., 4/27 | JV Baseball | Trinity Catholic | Away - Rippowam | 4:15 p.m. | ||
| Wed., 4/27 | V Boys Golf | Greenwich | Away - Round Hill Club [Directions] | 3:15 p.m. | Wilton - 187 Greenwich - 162 | |
| Wed., 4/27 | FR Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Wed., 4/27 | V Boys Tennis | St. Lukes | Home - Wilton Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Danbury | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/27 | JV Boys Tennis | Greenwich | Home [Directions] | 4:30 p.m. | ||
| Wed., 4/27 | JV Boys Tennis | Greenwich | Home [Directions] | 4:30 p.m. | ||
| Wed., 4/27 | FR Girls Lacrosse | New Canaan | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Softball | Trinity Catholic | Home - WHS Varsity Softball Field [Directions] | 6:30 p.m. | L 1-4 | |
| Wed., 4/27 | V Girls Tennis | Danbury | Away - Danbury HS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/27 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Golf | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:15 p.m. | Wilton - 163 McMahon - 209 | |
| Thu., 4/28 | V Boys Lacrosse | Trinity Catholic | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | W 18-0 | |
| Thu., 4/28 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 4/28 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | Wilton - 211 Danbury - 173 | |
| Thu., 4/28 | V Girls Lacrosse | Norwalk | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 15-4 | |
| Thu., 4/28 | JV Girls Lacrosse | Norwalk | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Outdoor Track | Norwalk, Darien | Away - Darien H.S. [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Tennis | Darien | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/28 | JV Girls Tennis | Darien | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Baseball | Danbury | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 3-5 | |
| Fri., 4/29 | JV Baseball | Danbury | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/29 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:30 p.m. | ||
| Fri., 4/29 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 4:30 p.m. | L 3-8 | |
| Fri., 4/29 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | Cancelled | Cancelled | |
| Sat., 4/30 | V Boys Lacrosse | John Jay (NY) | Home - Fujitani Field - Turf [Directions] | 6:30 p.m. | W 7-6 | |
| Sat., 4/30 | JV Boys Lacrosse | John Jay (NY) | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Sat., 4/30 | V Girls Lacrosse | Northport (NY) | Away | 2:30 p.m. | L 6-12 | |
| Sat., 4/30 | JV Girls Lacrosse | Northport (NY) | Away | Cancelled | Cancelled | |
| Mon., 5/2 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | L 2-8 | |
| Mon., 5/2 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:30 p.m. | ||
| Mon., 5/2 | FR Baseball | Darien | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Boys Golf | Staples | Home - Rolling Hills CC [Directions] | 3:30 p.m. | Wilton - 183 Staples - 167 | |
| Mon., 5/2 | FR Boys Lacrosse | Danbury | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | JV Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | ||
| Mon., 5/2 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| Mon., 5/2 | V Girls Outdoor Track | Fairfield Warde, Brien McMahon | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Softball | Darien | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | W 4-3(9) | |
| Tue., 5/3 | JV Boys Golf | Staples | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | JV Boys Golf | Staples | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Boys Lacrosse | St. Joseph | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | W 17-9 | |
| Tue., 5/3 | JV Boys Lacrosse | St. Joseph | Home - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Tue., 5/3 | V Girls Golf | Darien | Home - Silver Mine CC [Directions] | 3:15 p.m. | Wilton - 172 Darien - 184 | |
| Tue., 5/3 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 20-4 | |
| Tue., 5/3 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | Cancelled | Cancelled | |
| Wed., 5/4 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | Wilton - 182 New Canaan - 159 | |
| Wed., 5/4 | JV Boys Golf | New Canaan | Home - New Canaan Country Club [Directions] | 3:30 p.m. | ||
| Wed., 5/4 | FR Boys Lacrosse | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:30 p.m. | ||
| Wed., 5/4 | V Girls Outdoor Track | Darien | Away - Darien HS [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | JV Boys Golf | Staples | Home - Longshore [Directions] | 3:30 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | L 6-7(OT) | |
| Thu., 5/5 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | ||
| Thu., 5/5 | V Boys Outdoor Track | Fairfield Warde, Brien McMahon | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Tennis | Brien McMahon | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/5 | V Boys Tennis | Trumbull | Home - Wilton Tennis Courts [Directions] | 6:30 p.m. | W 7-0 | |
| Thu., 5/5 | V Girls Golf | Danbury | Home - Silver Mine CC [Directions] | 3:30 p.m. | Wilton - 185 Danbury - 170 | |
| Thu., 5/5 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | W 12-6 | |
| Thu., 5/5 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Softball | Stamford | Home - WHS Varsity Softball Field [Directions] | 6:30 p.m. | L 1-9 | |
| Thu., 5/5 | JV Softball | Stamford | Home - JV Softball Field [Directions] | Cancelled | Cancelled | |
| Thu., 5/5 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/5 | V Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 6:30 p.m. | W 4-3 | |
| Fri., 5/6 | V Boys Tennis | St. Joseph | Home - 4 Seasons Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Fri., 5/6 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | Cancelled | Cancelled | |
| Sat., 5/7 | V Baseball | Stamford | Away - Stamford HS [Directions] | 3:00 p.m. | L 2-3 | |
| Sat., 5/7 | JV Baseball | Stamford | Away [Directions] | 3:00 p.m. | ||
| Sat., 5/7 | V Boys Lacrosse | Fairfield Warde | Home - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 17-1 | Senior Night |
| Sat., 5/7 | JV Boys Lacrosse | Fairfield Warde | Home - Whitten Field [Directions] | 5:00 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | North Shore (NY) | Away | 4:30 p.m. | L 7-9 | |
| Mon., 5/9 | V Baseball | Brien McMahon | Home - WHS Varsity Baseball Field [Directions] | 7:00 p.m. | W 5-0 | |
| Mon., 5/9 | JV Baseball | Brien McMahon | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/9 | FR Baseball | Brien McMahon | Away [Directions] | Cancelled | Cancelled | |
| Mon., 5/9 | V Boys Golf | Fairfield Ludlowe | Home - Rolling Hills CC [Directions] | 3:30 p.m. | Wilton - 178 Ludlowe - 173 | |
| Mon., 5/9 | JV Boys Golf | New Canaan | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 5/9 | JV Boys Lacrosse | Fairfield Prep | Home - Whitten Field [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | JV Boys Lacrosse | Fairfield Prep | Home - Whitten Field [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | FR Boys Lacrosse | Fairfield Prep | Away - Barlow Field, Fairfield University [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | FR Boys Lacrosse | Fairfield Prep | Away - Barlow Field, Fairfield University [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Boys Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Mon., 5/9 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Girls Golf | Fairfield Ludlowe | Home [Directions] | 3:30 p.m. | Wilton - 169 Ludlowe - 202 | |
| Mon., 5/9 | V Girls Lacrosse | Sacred Heart-Hempstead (NY) | Home - Lilly Field - Turf [Directions] | 6:30 p.m. | L 8-9 | |
| Mon., 5/9 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Lilly Field - Turf [Directions] | 5:00 p.m. | ||
| Mon., 5/9 | V Girls Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:15 p.m. | W 24-6 | |
| Mon., 5/9 | JV Softball | Brien McMahon | Away - Brookside Elementary School [Directions] | Cancelled | Cancelled | |
| Mon., 5/9 | V Girls Tennis | Staples | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 5/9 | JV Girls Tennis | Ridgefield | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Baseball | Trumbull | Home - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | W 2-0 | |
| Tue., 5/10 | JV Baseball | Trumbull | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/10 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/10 | V Boys Golf | Trumbull | Home - Rolling Hills CC [Directions] | 3:30 p.m. | Wilton - 179 Trumbull - 165 Norwalk - 223 | Trumbull/Norwalk |
| Tue., 5/10 | V Boys Golf | Norwalk | Home - Rolling Hills CC [Directions] | 3:30 p.m. | Wilton - 179 Trumbull - 165 Norwalk - 223 | Trumbull/Norwalk |
| Tue., 5/10 | JV Boys Golf | Greenwich | Away - Griffith-Harris Gold Club [Directions] | 3:30 p.m. | Event Cancelled | |
| Tue., 5/10 | V Boys Tennis | New Canaan | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 5/10 | JV Boys Tennis | New Canaan | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Girls Golf | Darien | Away - CC of Darien [Directions] | 3:00 p.m. | Wilton - 217 Darien - 215 | |
| Tue., 5/10 | V Girls Lacrosse | St. Joseph | Home - Lilly Field - Turf [Directions] | 6:00 p.m. | W 18-3 | Senior Night |
| Tue., 5/10 | JV Girls Lacrosse | St. Joseph | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:30 p.m. | L 3-15 | |
| Tue., 5/10 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 5/10 | JV Girls Tennis | New Canaan | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:30 p.m. | L 0-2 | |
| Wed., 5/11 | JV Baseball | Staples | Away - Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | FR Baseball | Staples | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | 3:15 p.m. | Wilton - 173 Trinity - 187 | |
| Wed., 5/11 | V Boys Lacrosse | Yorktown (NY) | Away | 7:30 p.m. | W 11-9 | |
| Wed., 5/11 | JV Boys Lacrosse | Yorktown (NY) | Away | 4:30 p.m. | ||
| Wed., 5/11 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | V Boys Tennis | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/11 | JV Boys Tennis | Fairfield Warde | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Softball | Staples | Home - WHS Varsity Softball Field [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 5/11 | V Girls Tennis | Stamford | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | Senior Day |
| Thu., 5/12 | JV Baseball | New Canaan | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 5/12 | JV Boys Golf | Darien | Away - Woodway CC [Directions] | 3:15 p.m. | ||
| Thu., 5/12 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 11-2 | |
| Thu., 5/12 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | 5:00 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Westhill | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Thu., 5/12 | V Girls Golf | Trumbull | Home - Silver Mine CC [Directions] | 3:30 p.m. | Wilton - 170 Trumbull - 174 | |
| Thu., 5/12 | V Girls Lacrosse | Staples | Away - Staples Stadium [Directions] | 5:30 p.m. | L 10-15 | |
| Thu., 5/12 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 6:30 p.m. | W 6-2 | |
| Thu., 5/12 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | Cancelled | Cancelled | |
| Thu., 5/12 | V Girls Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/12 | JV Girls Tennis | Staples | Home - Middlebrook School [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Baseball | New Canaan | Home - WHS Varsity Baseball Field [Directions] | 2:15 p.m. | W 1-0 | |
| Fri., 5/13 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | Cancelled | Cancelled | |
| Fri., 5/13 | FR Boys Lacrosse | New Canaan | Home - Fujitani Field - Turf [Directions] | 5:00 p.m. | ||
| Fri., 5/13 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 5/14 | V Boys Lacrosse | Norwalk | Away - Testa Field [Directions] | 5:00 p.m. | W 16-8 | |
| Sat., 5/14 | JV Boys Lacrosse | Norwalk | Away - Testa Field [Directions] | 3:00 p.m. | ||
| Sat., 5/14 | V Girls Tennis | St. Joseph | Away [Directions] | 12:00 p.m. | W 7-0 | |
| Mon., 5/16 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:30 p.m. | L 0-1 | Senior Night |
| Mon., 5/16 | JV Baseball | Westhill | Away - Rippowam MS [Directions] | 4:30 p.m. | ||
| Mon., 5/16 | FR Baseball | Westhill | Home - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | JV Boys Golf | Ridgefield | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 5/16 | JV Boys Golf | Ridgefield | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 5/16 | V Boys Tennis | Norwalk | Home - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/16 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:30 p.m. | Wilton - 214 Warde - 196 | |
| Mon., 5/16 | V Girls Outdoor Track | St. Joseph | Home [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Softball | Westhill | Home - WHS Varsity Softball Field [Directions] | 6:30 p.m. | L 3-6 | Senior Night |
| Mon., 5/16 | V Girls Tennis | Norwalk | Away - Norwalk HS [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/17 | V Boys Golf | Danbury | Home - Rolling Hills CC [Directions] | 3:30 p.m. | Wilton - 184 Danbury - 169 | |
| Tue., 5/17 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | St. Joseph | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | L 6-12 | |
| Tue., 5/17 | JV Girls Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 5:30 p.m. | ||
| Tue., 5/17 | FR Girls Lacrosse | Ridgefield | Home - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Baseball | Norwalk | Home - WHS Varsity Baseball Field [Directions] | 7:00 p.m. | W 4-3 | Senior Night |
| Wed., 5/18 | JV Baseball | Norwalk | Home - JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/18 | FR Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Golf | Bridgeport Central | Away - Fairchild Wheeler Golf Course [Directions] | 3:15 p.m. | Wilton - 171 | |
| Wed., 5/18 | FR Boys Lacrosse | New Fairfield | Home - Allen's Field [Directions] | 5:00 p.m. | ||
| Wed., 5/18 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | 4:15 p.m. | W 6-5(8) | |
| Wed., 5/18 | V Girls Tennis | Staples | Away [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Boys Golf | Ridgefield | Home - Silver Spring Country Club [Directions] | 3:30 p.m. | Wilton - 175 Ridgefield - 166 | |
| Thu., 5/19 | JV Boys Golf | Ridgefield | Away - Silver Spring CC [Directions] | 3:30 p.m. | ||
| Thu., 5/19 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 5/19 | V Boys Tennis | FCIAC Tournament | Home [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Girls Golf | Staples | Home - Silver Mine CC [Directions] | 3:15 p.m. | Wilton - 172 Staples - 168 | |
| Thu., 5/19 | FR Girls Lacrosse | Greenwich | Home - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | Cancelled | Cancelled | |
| Fri., 5/20 | V Girls Lacrosse | FCIAC Tournament | Away | Cancelled | Cancelled | |
| Fri., 5/20 | V Girls Lacrosse | FCIAC Tournament | Away | Cancelled | Cancelled | |
| Fri., 5/20 | V Girls Lacrosse | FCIAC Tournament | Away | Cancelled | Cancelled | |
| Fri., 5/20 | V Girls Lacrosse | FCIAC Quarterfinals | Away | TBA | ||
| Fri., 5/20 | V Girls Tennis | FCIAC Tournament | Away | 4:00 p.m. | ||
| Sat., 5/21 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Sat., 5/21 | V Boys Lacrosse | FCIAC Quarter Finals | Away | TBA | ||
| Sat., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away [Directions] | 12:00 p.m. | ||
| Sat., 5/21 | V Girls Outdoor Track | FCIAC Championships | Away | 12:00 p.m. | ||
| Mon., 5/23 | JV Boys Golf | Fairfield Ludlowe | Home - Rolling Hills CC [Directions] | 3:30 p.m. | ||
| Mon., 5/23 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Girls Lacrosse | FCIAC Semi Finals | Away | TBA | ||
| Tue., 5/24 | V Boys Golf | St. Joseph | Away - Tashua Knolls [Directions] | 3:15 p.m. | Wilton - 169 St. Joseph - 188 | |
| Tue., 5/24 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | Wilton - 213 New Canaan - 203 | |
| Tue., 5/24 | V Softball | New Canaan (Scrim.) | Home - WHS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/24 | V Girls Tennis | FCIAC Tournament | Home - Wilton Tennis Courts [Directions] | TBA | ||
| Wed., 5/25 | V Boys Golf | Stamford | Away - E.G. Brennan [Directions] | 3:15 p.m. | Wilton - 170 Stamford - 193 | |
| Wed., 5/25 | V Boys Lacrosse | FCIAC SEMI FINALS | Away - MC MAHON HIGH SCHOOL | Cancelled | Cancelled | |
| Wed., 5/25 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Wilton - 201 Ludlowe - 228 | |
| Wed., 5/25 | V Girls Lacrosse | FCIAC Finals | Away | Cancelled | Cancelled | |
| Wed., 5/25 | V Girls Outdoor Track | 29th Freshman Meet | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Sat., 5/28 | V Boys Lacrosse | FCIAC FINALS | Away - MC MAHON HIGH SCHOOL | TBA | ||
| Sat., 5/28 | V Boys Lacrosse | PLAY IN FOR STATES | Away | TBA | ||
| Tue., 5/31 | V Baseball | Cheshire | Away - Cheshire High Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class L Championships | Away | 3:00 p.m. | ||
| Tue., 5/31 | V Girls Lacrosse | South Windsor | Away - SWHS Stadium Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class L Championship | Away - Middletown | 3:00 p.m. | ||
| Tue., 5/31 | V Softball | Fairfield Warde | Away [Directions] | 4:00 p.m. | W 4-2 | |
| Wed., 6/1 | V Baseball | Norwich Free Academy | Home - WHS Varsity Baseball Field [Directions] | 3:30 p.m. | W 3-2 | |
| Wed., 6/1 | V Baseball | Norwich Free Academy | Home - WHS Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Norwich Free Academy | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Norwich Free Academy | Home - Fujitani Field - Turf [Directions] | 4:30 p.m. | W 20-2 | |
| Wed., 6/1 | V Boys Lacrosse | 1ST ROUND STATES | Away | TBA | ||
| Wed., 6/1 | V Softball | Middletown | Away [Directions] | Cancelled | Cancelled | |
| Wed., 6/1 | V Girls Tennis | Greenwich | Away [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Girls Tennis | Greenwich | Away [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Girls Tennis | Greenwich | Away [Directions] | 3:00 p.m. | ||
| Thu., 6/2 | V Girls Lacrosse | Cheshire | Away - Cheshire High Main Game field [Directions] | 5:00 p.m. | ||
| Sat., 6/4 | V Baseball | New Milford | Away - New Milford HS [Directions] | 11:00 a.m. | ||
| Sat., 6/4 | V Boys Lacrosse | Simsbury | Away - Simsbury HS - Holden Field (turf) [Directions] | 12:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC Open | Away - New Britain | 1:30 p.m. | ||
| Wed., 6/8 | V Boys Lacrosse | CIAC SEMI FINALS | Away | TBA | ||
| Wed., 10/19 | Miscellaneous Events | College Fair | Home - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||