| Stamford 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 810 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Thu., 8/25 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Ludlowe 153, Stamford 202 | 1:30 PM | |
| Sat., 8/27 | V Football | Westhill (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Mon., 8/29 | V Boys Golf | Darien | Home - Stamford High-Sterling Farms Golf Course [Directions] | Darien 164, Stamford 205 | ||
| Tue., 8/30 | V Boys Golf | Fairfield Warde | Home - Stamford High-Sterling Farms Golf Course [Directions] | Warde 150, Stamford 201 | ||
| Wed., 8/31 | V Boys Soccer | New Canaan (Scrim.) | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | 5:00 PM | |
| Wed., 8/31 | JV Boys Soccer | New Canaan (Scrim.) | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 8/31 | V Girls Soccer | Stratford (Scrim.) | Away - Penders Field-Penders Field - Stratford [Directions] | 4:00 p.m. | ||
| Thu., 9/1 | FR Football | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:00 p.m. | 3:00 PM | |
| Thu., 9/1 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | Ridgefield 161, Stamford 198 | 2:00 PM | |
| Thu., 9/1 | V Girls Volleyball | Greenwich (Scrim.) | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | 2:45 PM | |
| Fri., 9/2 | V Football | Norwalk (Scrim.) | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | 3:45 PM (2 buses) | |
| Sat., 9/3 | V Boys Soccer | Bethel (Scrim.) | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 10:30 a.m. | ||
| Sat., 9/3 | V Boys Soccer | Seymour (Scrim.) | Home - Amity Regional HS-Amity High School - Field # 2 [Directions] | 11:00 a.m. | ||
| Sat., 9/3 | V Boys Soccer | Daniel Hand (Scrim.) | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 9:30 a.m. | ||
| Sat., 9/3 | V Field Hockey | Norwalk Play Day - Field Hockey | Away - Not Listed-Norwalk HS | 9:30 a.m. | 8:00 AM | |
| Sat., 9/3 | V Girls Soccer | JLHS Girls Soccer Jamboree | Away - Jonathan Law HS-Lawmen Stadium | 8:30 a.m. | 7:15 AM | |
| Sat., 9/3 | V Girls Volleyball | Joel Barlow (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 9/6 | V Boys Soccer | Bethel (Scrim.) | Away - Bethel HS-Rourke Field [Directions] | Cancelled | 4:20 PM | |
| Tue., 9/6 | V Girls Volleyball | Wright Tech (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 9/6 | JV Girls Volleyball | Wright Tech (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 9/7 | V Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | FR Football | Wilbur Cross | Home - Stamford HS-Boyle Stadium [Directions] | W 14-12 | ||
| Thu., 9/8 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | L 2-1 | 2:15 PM | |
| Thu., 9/8 | JV Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Thu., 9/8 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 3-0 | 2:30 PM | |
| Thu., 9/8 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 9/9 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | L 8-1 | 2:15 PM | |
| Fri., 9/9 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 9/9 | V Girls Swimming and Diving | Staples | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/9 | V Girls Volleyball | Shelton | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-2 | ||
| Sat., 9/10 | V Football | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | W 41-12 | 10:00 AM (2 buses) | |
| Sat., 9/10 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 9:30 a.m. | 8:00 AM | |
| Sat., 9/10 | V Competitive Cheerleading | Wilber Cross | Away - Not Listed | 1:00 p.m. | 11:00 AM | |
| Sat., 9/10 | V Girls Volleyball | Foran | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-1 | ||
| Mon., 9/12 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | Staples 153, Stamford 171 | 1:45 PM | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/3, Time to 3:15 p.m. | ||||||
| Mon., 9/12 | V Field Hockey | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | W 4-3 | ||
| Mon., 9/12 | JV Field Hockey | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/12 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | L 3-0 | 2:30 PM | |
| Mon., 9/12 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | 2:30 PM | |
| Tue., 9/13 | V Boys Golf | New Canaan | Home - Stamford High-Sterling Farms Golf Course [Directions] | New Canaan 166, Stamford 204 | ||
| Tue., 9/13 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 3-0 | ||
| Tue., 9/13 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 6:00 p.m. | ||
| Tue., 9/13 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/14 | V Boys Cross Country | St. Joseph, Fairfield Ludlowe | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/14 | V Girls Cross Country | St. Joseph, Fairfield Ludlowe | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/14 | V Field Hockey | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | L 8-0 | ||
| Wed., 9/14 | JV Field Hockey | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 2-0 | 2:15 PM | |
| Wed., 9/14 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/14 | V Girls Swimming and Diving | Danbury | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | Harding | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Wed., 9/14 | JV Girls Volleyball | Harding | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 9/15 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Danbury 157, Stamford 203 | 1:30 PM | |
| Thu., 9/15 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 2-1 | 4:45 PM | |
| Thu., 9/15 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 9/16 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 27-54 | 3:45 PM (2 buses) | |
| Fri., 9/16 | FR Football | Somers (NY) | Away - Not Listed | W 14-7 | 2:30 PM | |
| Fri., 9/16 | FR Boys Soccer | Fairfield Warde | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Fri., 9/16 | V Competitive Cheerleading | At Danbury HS | Away - Not Listed-Danbury HS | 7:00 p.m. | 5:00 PM | |
| Fri., 9/16 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/16 | V Girls Volleyball | Weston | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/16 | JV Girls Volleyball | Weston | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Wilton XC invitational | Away - Not Listed-Allen Meadow Park, Wilton HS | 9:30 a.m. | 8:00 AM | |
| Sat., 9/17 | JV Football | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | W 40-0 | ||
| Sat., 9/17 | V Girls Cross Country | Wilton XC invitational | Away - Not Listed-Allen Meadow Park, Wilton HS | 9:30 a.m. | 8:00 AM | |
| Sat., 9/17 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 4-0 | 9:45 AM (.) | |
| Sat., 9/17 | JV Field Hockey | Westhill | Away - Westhill HS-Front Turf [Directions] | 12:30 p.m. | 9:45 AM (.) | |
| Sat., 9/17 | V Girls Soccer | Fairfield Warde | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 5-1 | ||
| Sat., 9/17 | JV Girls Soccer | Fairfield Warde | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 1:00 p.m. | ||
| Mon., 9/19 | V Boys Golf | Greenwich | Home - Stamford High-Sterling Farms Golf Course [Directions] | Greenwich 154, Stamford 180 | ||
| Mon., 9/19 | V Boys Soccer | Wilton | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 2-0 | ||
| Mon., 9/19 | JV Boys Soccer | Wilton | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Mon., 9/19 | FR Boys Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 9/20 | V Boys Cross Country | Fairfield Warde, Greenwich, Norwalk | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:00 PM | |
| Tue., 9/20 | V Boys Golf | Wilton | Home - Stamford High-Sterling Farms Golf Course [Directions] | Wilton 164, Stamford 184 | ||
| Tue., 9/20 | V Girls Cross Country | Fairfield Warde, Greenwich, Norwalk | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:00 PM | |
| Tue., 9/20 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | L 0-7 | 3:15 PM | |
| Tue., 9/20 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | 3:15 PM | |
| Tue., 9/20 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | L 3-0 | 3:30 PM | |
| Tue., 9/20 | JV Girls Soccer | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/21 | V Boys Golf | Trumbull | Home - Stamford High-Sterling Farms Golf Course [Directions] | Trumbull 162, Stamford 195 | ||
| Thu., 9/22 | FR Football | Manchester | Home - Stamford HS-Boyle Stadium [Directions] | L 30-8 | ||
| Thu., 9/22 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 1-0 | 5:15 PM | |
| Thu., 9/22 | JV Boys Soccer | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | 3:15 PM | |
| Thu., 9/22 | FR Boys Soccer | New Canaan | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Thu., 9/22 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 3-0 | 2:15 PM | |
| Thu., 9/22 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Thu., 9/22 | FR Girls Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 9/23 | V Field Hockey | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | L 3-1 | ||
| Fri., 9/23 | JV Field Hockey | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | V Girls Soccer | New Canaan | Home - Stamford HS-SHS Upper Soccer Field [Directions] | T 1-1 | ||
| Fri., 9/23 | JV Girls Soccer | New Canaan | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick up) | |
| Sat., 9/24 | V Football | Manchester | Home - Stamford HS-Boyle Stadium [Directions] | W 27-21 (OT) | ||
| Sat., 9/24 | V Boys Soccer | Harding | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 6-1 | ||
| Sat., 9/24 | V Girls Volleyball | Bassick | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Sat., 9/24 | JV Girls Volleyball | Bassick | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:30 a.m. | ||
| Mon., 9/26 | JV Football | Bullard/Kolbe | Away - Bullard Havens Tech-Football Field [Directions] | W 47-0 | 2:00 PM | |
| Wed., 9/28 | V Boys Cross Country | New Canaan, Westhill, Wilton | Away - Waveny Park [Directions] | 4:30 p.m. | 3:15 PM | |
| Wed., 9/28 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | McMahon 175, Stamford 186 | 2:00 PM | |
| Wed., 9/28 | V Boys Soccer | Ridgefield | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 2-1 | ||
| Wed., 9/28 | JV Boys Soccer | Ridgefield | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Wed., 9/28 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/28 | V Girls Cross Country | New Canaan, Westhill, Wilton | Away - Waveny Park [Directions] | 4:30 p.m. | 3:15 PM | |
| Wed., 9/28 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 2-1 | 2:15 PM | |
| Wed., 9/28 | JV Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 5:30 p.m. | 2:15 PM | |
| Wed., 9/28 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 3-0 | 2:15 PM | |
| Wed., 9/28 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/28 | V Girls Swimming and Diving | Wilton | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 3-2 | ||
| Wed., 9/28 | JV Girls Volleyball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | 3:00 PM | |
| Thu., 9/29 | FR Football | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | V Boys Golf | Westhill | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/29 | V Girls Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Thu., 9/29 | JV Girls Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 9/29 | FR Girls Volleyball | Danbury | Away - Danbury HS-New gym [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 9/30 | V Boys Soccer | Trumbull | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 3-2 | ||
| Fri., 9/30 | JV Boys Soccer | Trumbull | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Fri., 9/30 | FR Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 9/30 | V Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | W 2-0 | 3:30 PM | |
| Fri., 9/30 | JV Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:30 p.m. | 3:30 PM | |
| Fri., 9/30 | V Girls Swimming and Diving | Trumbull | Away - Bridgeport Univ Pool-Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | L 29-41 | ||
| Sat., 10/1 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | L 6-1 | 1:00 PM | |
| Sat., 10/1 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 5:00 p.m. | 1:00 PM | |
| Sat., 10/1 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 3-1 | 12:45 PM | |
| Sat., 10/1 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 2:30 p.m. | 12:45 PM | |
| Sat., 10/1 | FR Girls Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/3 | V Boys Cross Country | Ridgefield, Brien McMahon, Danbury | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Mon., 10/3 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 19-6 | 3:00 PM | |
| Mon., 10/3 | V Girls Cross Country | Ridgefield, Brien McMahon, Danbury | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Mon., 10/3 | V Field Hockey | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | L 6-1 | ||
| Mon., 10/3 | JV Field Hockey | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/3 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | 2:30 PM | |
| Thu., 10/6 | V Boys Golf | Chappa Invitational - Long Shore | Away - Not Listed-Longshore Golf Course | 9:30 a.m. | 8:45 AM, Dismiss 8:00 AM | |
| Thu., 10/6 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 1-0 | 4:45 PM | |
| Thu., 10/6 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 5:00 p.m. | 3:00 PM | |
| Thu., 10/6 | FR Boys Soccer | Fairfield Ludlowe | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Thu., 10/6 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 3-0 | ||
| Thu., 10/6 | JV Girls Volleyball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 10/7 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 0-2 | 2:45 PM | |
| Fri., 10/7 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | 2:45 PM | |
| Fri., 10/7 | V Girls Soccer | Fairfield Ludlowe | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 0-3 | ||
| Fri., 10/7 | JV Girls Soccer | Fairfield Ludlowe | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:10 PM (Parent Pick up) | |
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational | Away - Not Listed-Wickham Park | TBA | 6:45 AM | |
| Sat., 10/8 | V Boys Soccer | Brien McMahon | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 1-0 | ||
| Sat., 10/8 | JV Boys Soccer | Brien McMahon | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/8 | V Competitive Cheerleading | Light the Night - Leukemia Walk - Calf Pasture Beach - Norwalk | Away - Not Listed | 5:00 p.m. | 3:30 PM | |
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational | Away - Not Listed-Wickham Park | TBA | 6:45 AM | |
| Sat., 10/8 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | L 3-0 | 10:45 AM | |
| Sat., 10/8 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 2:00 p.m. | 10:45 AM | |
| Mon., 10/10 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | L 2-0 | 2:00 PM | |
| Mon., 10/10 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | 2:00 PM | |
| Mon., 10/10 | FR Boys Soccer | Staples | Home - Stamford HS-SHS Upper Soccer Field [Directions] | Postponed | 3:15 PM (Parent Pick Up) | |
| Mon., 10/10 | V Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 3-2 | ||
| Mon., 10/10 | JV Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Mon., 10/10 | FR Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Tue., 10/11 | V Boys Cross Country | Staples, Darien, Trumbull | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | 2:20 PM | |
| Tue., 10/11 | V Boys Golf | Norwalk | Home - Stamford High-Sterling Farms Golf Course [Directions] | Norwalk 187, Stamford 188 | ||
| Tue., 10/11 | V Girls Cross Country | Staples, Darien, Trumbull | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | 2:20 PM | |
| Tue., 10/11 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 0-7 | 3:45 PM | |
| Tue., 10/11 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | 3:45 PM | |
| Tue., 10/11 | V Girls Soccer | Staples | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 1-4 | ||
| Tue., 10/11 | JV Girls Soccer | Staples | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | FR Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 6-0 | 5:00 PM | |
| Wed., 10/12 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | Westhill 155, Stamford 169 | TBA | |
| Wed., 10/12 | V Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | L 4-1 | 2:45 PM | |
| Wed., 10/12 | FR Boys Soccer | Westhill | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Wed., 10/12 | V Girls Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 3-0 | ||
| Wed., 10/12 | JV Girls Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/12 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Postponed | 2:45 PM | |
| Thu., 10/13 | V Girls Soccer | Westhill | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 1-0 | ||
| Thu., 10/13 | JV Girls Soccer | Westhill | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick up) | |
| Fri., 10/14 | V Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | L 14-42 | 4:00 PM (2 Buses) | |
| Fri., 10/14 | V Boys Soccer | Norwalk | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 5-1 | ||
| Fri., 10/14 | JV Boys Soccer | Norwalk | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Fri., 10/14 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | 2:00 PM | |
| Fri., 10/14 | V Competitive Cheerleading | At Trumbull HS | Away - Not Listed-Trumbull | 7:00 p.m. | 5:00 PM | |
| Fri., 10/14 | V Field Hockey | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | L 7-0 | ||
| Fri., 10/14 | JV Field Hockey | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Ridgefield | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 3-0 | 2:15 PM | |
| Fri., 10/14 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | 2:15 PM | |
| Fri., 10/14 | FR Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/15 | JV Football | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | L 18-12 | ||
| Sat., 10/15 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 4-2 | 2:30 PM | |
| Sat., 10/15 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Postponed | 12:30 PM | |
| Sat., 10/15 | FR Girls Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/17 | V Boys Golf | Holohan | Away - Not Listed-Wee Burn CC | 11:15 a.m. | TBA (Parent driven) | |
| Mon., 10/17 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | L 4-0 | 2:30 PM | |
| Mon., 10/17 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 10/17 | FR Boys Soccer | Darien | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Mon., 10/17 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | L 0-9 | 2:15 PM | |
| Mon., 10/17 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | 2:15 PM | |
| Mon., 10/17 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | L 3-0 | 2:45 PM | |
| Mon., 10/17 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | 2:45 PM | |
| Mon., 10/17 | FR Girls Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | St. Joe's 164, Stamford 193 | 1:45 PM | |
| Tue., 10/18 | V Girls Soccer | Darien | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 2-0 | ||
| Tue., 10/18 | JV Girls Soccer | Darien | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:30 PM | |
| Wed., 10/19 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:30 PM | |
| Wed., 10/19 | V Field Hockey | Immaculate | Home - Stamford HS-Boyle Stadium [Directions] | L 2-3 | ||
| Wed., 10/19 | JV Field Hockey | Immaculate | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/19 | V Girls Swimming and Diving | St. Joseph | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 3-0 | 3:00 PM | |
| Wed., 10/19 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | 3:00 PM | |
| Thu., 10/20 | FR Football | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | L 26-6 | ||
| Thu., 10/20 | V Boys Soccer | Bridgeport Central | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 6-1 | ||
| Thu., 10/20 | JV Boys Soccer | Bridgeport Central | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Fri., 10/21 | V Field Hockey | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | W 1-0 | ||
| Fri., 10/21 | JV Field Hockey | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | W 2-0 | 3:15 PM | |
| Fri., 10/21 | V Girls Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/21 | JV Girls Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 10/21 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | 3:15 PM | |
| Sat., 10/22 | V Football | Staples | Home - Stamford HS-Boyle Stadium [Directions] | L 7-42 | ||
| Sat., 10/22 | JV Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 12:00 p.m. | 10:45 AM | |
| Sat., 10/22 | V Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | L 3-1 | 7:30 AM | |
| Sat., 10/22 | JV Girls Soccer | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 10:00 a.m. | 7:30 AM | |
| Sat., 10/22 | FR Girls Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 4-0 | 3:00 PM | |
| Mon., 10/24 | JV Boys Soccer | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:15 p.m. | 3:00 PM | |
| Mon., 10/24 | FR Boys Soccer | Greenwich | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick Up) | |
| Mon., 10/24 | JV Field Hockey | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | 2:45 PM | |
| Mon., 10/24 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 2:30 PM | |
| Mon., 10/24 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | 2:30 PM | |
| Mon., 10/24 | FR Girls Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Field Hockey | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | W 3-0 | ||
| Tue., 10/25 | JV Field Hockey | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 7-1 | ||
| Wed., 10/26 | FR Football | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | L 15-6 | ||
| Wed., 10/26 | JV Girls Soccer | Greenwich | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM (Parent Pick up) | |
| Thu., 10/27 | V Girls Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Thu., 10/27 | JV Girls Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/28 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | L 0-3 | 3:00 PM | |
| Fri., 10/28 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | 3:00 PM | |
| Fri., 10/28 | FR Girls Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | Class LL Championship | Away - Not Listed-Wickham Park | 10:30 a.m. | 7:15 AM | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:45 a.m. | ||
| Sat., 10/29 | V Football | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | W 27-13 | ||
| Sat., 10/29 | V Girls Cross Country | Class LL Championship | Away - Not Listed-Wickham Park | 10:00 a.m. | 7:15 AM | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:10 a.m. | ||
| Sat., 10/29 | JV Girls Swimming and Diving | Greenwich, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 10:15 a.m. | ||
| Sat., 10/29 | JV Girls Swimming and Diving | Greenwich, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 10:15 a.m. | ||
| Sat., 10/29 | JV Girls Volleyball | Fairfield Warde, Fairfield Ludlowe, Greenwich, TBA, Newtown, Trumbull, Westhill | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | 7:00 AM | |
| Mon., 10/31 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | L 28-6 | 1:40 PM | |
| Tue., 11/1 | V Boys Golf | CIAC Division I Championship | Away - Stanley GC | 9:00 a.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championship | Home - Westhill HS-Westhill Pool [Directions] | 5:00 p.m. | ||
| Wed., 11/2 | V Girls Volleyball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 11/3 | FR Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 14-8 | 2:15 PM | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/4 | V Field Hockey | Norwalk (Scrim.) | Away - Norwalk HS-Testa Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Fri., 11/4 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Sat., 11/5 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | L 13-17 | 10:30 AM (2 buses) | |
| Sat., 11/5 | V Competitive Cheerleading | @ St. Joes | Away - Not Listed-St. Joes | 1:30 p.m. | 11:30 AM | |
| Mon., 11/7 | JV Football | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | L 21-14 | ||
| Mon., 11/7 | V Field Hockey | Newtown | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Tue., 11/8 | V Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 6:00 p.m. | 3:30 PM | |
| Thu., 11/10 | FR Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | L 12-8 | 1:30 PM | |
| Thu., 11/10 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Sat., 11/12 | V Football | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | L 10-49 | ||
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 11:15 a.m. | ||
| Wed., 11/16 | V Girls Swimming and Diving | CIAC Class LL Final | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | JV Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | W 34-22 | ||
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Thu., 11/24 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 33-6 | 8:30 AM | |
| Thu., 11/24 | V Competitive Cheerleading | Thanksgiving at Westhill | Away - Not Listed-Westhill HS | 10:00 a.m. | 9:00 AM | |
| Wed., 11/30 | V Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | 3:45 PM (Bus coming from Staples HS pick up at SHS) | |
| Sat., 12/3 | V Girls Basketball | Danbury Jamboree | Away - Not Listed-Danbury | TBA | 10:45 AM | |
| Tue., 12/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 (OT) | ||
| Sat., 12/10 | V Boys Basketball | Windsor High Jamboree | Away - Not Listed-Windsor HS | 12:00 p.m. | 10:30 AM | |
| Sat., 12/10 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Upper Rink [Directions] | L 3-0 | 2:15 PM ((with stop for Staples at Exit 18)) | |
| Mon., 12/12 | V Girls Basketball | Saddle River Day (NJ) (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/13 | V Boys Basketball | Hamden (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | L 2-5 | ||
| Wed., 12/14 | V Girls Basketball | Scarsdale (NY) | Away - Scarsdale Senior HS | L 41-35 | 3:15 PM | |
| Wed., 12/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 9-0 | ||
| Fri., 12/16 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | W 5-4 | ||
| Sat., 12/17 | V Boys Indoor Track | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | 12:15 PM | |
| Sat., 12/17 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | 6:45 AM | |
| Sat., 12/17 | V Girls Basketball | Pomperaug | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 28-36 | ||
| Sat., 12/17 | JV Girls Basketball | Pomperaug | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Sat., 12/17 | FR Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/17 | V Girls Ice Hockey | Avon | Away - Newington-Blue Rink [Directions] | L 5-0 | 1:45 PM ((with stop for Staples at Exit 18)) | |
| Sat., 12/17 | V Girls Indoor Track | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | 12:15 PM | |
| Tue., 12/20 | V Girls Basketball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | L 44-43 | 2:30 PM | |
| Tue., 12/20 | JV Girls Basketball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 5:00 p.m. | 2:30 PM | |
| Wed., 12/21 | V Boys Basketball | North Haven | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 65-40 | ||
| Wed., 12/21 | JV Boys Basketball | North Haven | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/21 | V Wrestling | New Canaan | Home - Stamford HS-SHS Aux Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 64-58 | 3:15 PM | |
| Thu., 12/22 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | 3:15 PM | |
| Thu., 12/22 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-Stadium [Directions] | 3:30 p.m. | 1:30 PM (1:30 Pick up ay WHS -> 1:45 pick up SHS student Lot -> pick up at Exit #18 ->Wonderland rink) | |
| Tue., 12/27 | V Boys Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | W 47-46 | 3:00 PM, Dismiss TBA (27th - Stamford vs B-port Central - 4pm - Bus at 3pm 29th - Stamford vs TBD - Bus TBD) | |
| Wed., 12/28 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 9-3 | ||
| Wed., 12/28 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-3 | ||
| Thu., 12/29 | V Boys Basketball | Bethel | Away - Westhill HS-Main Gym [Directions] | W 59-34 | ||
| Thu., 12/29 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-LIberty Rink [Directions] | W 7-2 | ||
| Thu., 12/29 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | W 3-1 | 9:45 AM ((with stop for Staples at Exit 18)) | |
| Fri., 12/30 | V Wrestling | Darien, Danbury, Staples | Away - Darien HS-DHS South Gym [Directions] | 10:00 a.m. | 8:15 AM | |
| Fri., 12/30 | V Girls Basketball | Southington | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 60-35 | ||
| Fri., 12/30 | JV Girls Basketball | Southington | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 1/3 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 49-36 | 3:30 PM | |
| Tue., 1/3 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | 3:30 PM | |
| Tue., 1/3 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | Cancelled | 2:15 PM | |
| Wed., 1/4 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 9-2 | ||
| Wed., 1/4 | V Boys Swimming and Diving | Staples | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/4 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | 4:30 PM | |
| Wed., 1/4 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-2 | ||
| Thu., 1/5 | V Girls Gymnastics | Westhill, Darien, New Canaan | Away - Westhill HS-New Gym [Directions] | 93.88 | TBA (Parent drop off and pick up at Westhill HS) | |
| Fri., 1/6 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 61-54 | 4:30 PM | |
| Fri., 1/6 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | 2:15 PM | |
| Fri., 1/6 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 1/6 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Girls Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 49-35 | ||
| Fri., 1/6 | JV Girls Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | FR Girls Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-3 | ||
| Sat., 1/7 | V Boys Indoor Track | The Bethel 8 Invitational | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | 12:45 AM | |
| Sat., 1/7 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | 6:45 AM | |
| Sat., 1/7 | V Girls Indoor Track | The Bethel 8 Invitational | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | 12:45 AM | |
| Mon., 1/9 | V Girls Gymnastics | Westhill, Greenwich | Away - Westhill HS-New Gym [Directions] | 108.2 | TBA (Parent drop off and pick up at Westhill HS) | |
| Tue., 1/10 | V Boys Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 65-60 | ||
| Tue., 1/10 | JV Boys Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 51-28 | 2:30 PM | |
| Tue., 1/10 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 1/11 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 7-1 | ||
| Wed., 1/11 | V Wrestling | Fairfield Warde | Home - Stamford HS-SHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-1 | ||
| Thu., 1/12 | V Boys Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 52-71 | ||
| Thu., 1/12 | JV Boys Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/12 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 52-43 | 4:30 PM | |
| Thu., 1/12 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Thu., 1/12 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 1/13 | V Boys Swimming and Diving | Darien | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | L 3-1 | 3:45 PM (Bus coming from Staples HS pick up at SHS) | |
| Sat., 1/14 | V Boys Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 70-38 | ||
| Sat., 1/14 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 1-6 | ||
| Sat., 1/14 | V Boys Indoor Track | Staples, Darien, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | 8:15 AM | |
| Sat., 1/14 | V Girls Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 51-36 | ||
| Sat., 1/14 | V Girls Indoor Track | Staples, Darien, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | 8:15 AM | |
| Sat., 1/14 | Unified Sports Basketball | Westhill | Home - Stamford HS-SHS Aux Gym [Directions] | 1:45 p.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | East Haven Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-2 | ||
| Tue., 1/17 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 69-71 | 4:00 PM | |
| Tue., 1/17 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | 2:30 PM | |
| Tue., 1/17 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 1/17 | V Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 45-53 | ||
| Tue., 1/17 | JV Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Wrestling | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | 3:15 PM | |
| Wed., 1/18 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 3-2 | TBA (Parent pick up /drop off at Darien Ice House Separate Staples bus from Westport) | |
| Thu., 1/19 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 5-2 | ||
| Thu., 1/19 | V Girls Gymnastics | Staples, Norwalk, Westhill | Away - Staples HS-Westport YMCA [Directions] | 103.65 | 5:15 PM (Pick up and Drop off at Stamford HS) | |
| Fri., 1/20 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | W 63-60 | 4:00 PM | |
| Fri., 1/20 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Fri., 1/20 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 1/20 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 40-36 | ||
| Fri., 1/20 | JV Girls Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Girls Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | T 2-2 | 1:45 PM (1:45 from SHS with pick up at WHS at 2:00 -- Seperate bus from Westport for Staples --) | |
| Sat., 1/21 | V Boys Indoor Track | Staples, Darien, Norwalk | Away - Staples HS-Field House [Directions] | 10:00 a.m. | 8:15 AM | |
| Sat., 1/21 | V Boys Indoor Track | U.S. Army Officials Hall of Fame Invitational | Away - Not Listed-Armory Athletic Center, NYC, New York | 8:00 a.m. | 6:30 AM | |
| Sat., 1/21 | JV Wrestling | Patton JV Tournament | Away - Danbury HS-Main Gym | 9:30 a.m. | 7:00 AM | |
| Sat., 1/21 | V Competitive Cheerleading | Nighthawk Cheer Classic @ North Haven HS | Away - Not Listed-North Haven HS | TBA | 12:45 PM | |
| Sat., 1/21 | V Girls Gymnastics | Trumbull, Westhill | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 55.95 | 4:15 PM (Pick up and drop off at Stamford HS) | |
| Sat., 1/21 | V Girls Gymnastics | St. Joseph, Westhill | Away - St. Joseph HS-Next Dimensions [Directions] | 55.95 | 4:15 PM (Pick up and Drop off at Stamford HS) | |
| Sat., 1/21 | V Girls Indoor Track | Staples, Darien, Norwalk | Away - Staples HS-Field House [Directions] | 10:00 a.m. | 8:15 AM | |
| Sat., 1/21 | V Girls Indoor Track | U.S. Army Officials Hall of Fame Invitational | Away - Not Listed-Armory Athletic Center, NYC, New York | 8:00 a.m. | 6:30 AM | U.S. Army Officials Hall of Fame Invitational |
| Mon., 1/23 | V Girls Gymnastics | Westhill, Wilton | Away - Westhill HS-New Gym [Directions] | 113.05 | TBA (Parent Drop off and Pick up at Westhill HS) | |
| Mon., 1/23 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-2 | ||
| Tue., 1/24 | V Boys Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 48-51 | ||
| Tue., 1/24 | JV Boys Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 50-39 | 2:45 PM | |
| Tue., 1/24 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | 2:45 PM | |
| Wed., 1/25 | V Boys Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 6-3 | ||
| Wed., 1/25 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/25 | V Wrestling | St. Joseph | Home - Stamford HS-SHS Aux Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/25 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Fri., 1/27 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | L 49-50 | 5:00 PM | |
| Fri., 1/27 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | 2:45 PM | |
| Fri., 1/27 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 2:45 PM | |
| Fri., 1/27 | V Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 44-35 | ||
| Fri., 1/27 | JV Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Trumbull | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-0 | ||
| Sat., 1/28 | V Wrestling | Norwalk JV Invite | Away - Not Listed-Norwalk HS | 9:00 a.m. | 7:30 AM | |
| Sat., 1/28 | JV Wrestling | Neil Godleski Wrestling Tournament | Away - Norwalk HS-Tom Scarso Gymnasium | 9:00 a.m. | 7:30 AM | |
| Sat., 1/28 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 6-0 | 7:20 PM (Separate Staples bus from Westport) | |
| Sun., 1/29 | V Wrestling | Queen of the Mat at Foran HS | Away - Not Listed-Foran HS | 1:00 p.m. | TBA (This is a parent drop off and pick up event) | |
| Mon., 1/30 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Tue., 1/31 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | W 36-25 | 4:45 PM | |
| Tue., 1/31 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | 2:45 PM | |
| Tue., 1/31 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 1/31 | V Girls Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 34-27 | ||
| Tue., 1/31 | JV Girls Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Girls Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | W 4-2 | ||
| Wed., 2/1 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 2/1 | V Wrestling | Fairfield Ludlowe | Home - Stamford HS-SHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/1 | V Girls Gymnastics | Fairfield Ludlowe, Westhill | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 118.9 | 5:00 PM (Bus Pick up and Drop off at Stamford HS) | |
| Wed., 2/1 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-0 | ||
| Thu., 2/2 | V Boys Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 55-49 | ||
| Thu., 2/2 | JV Boys Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | 2:00 PM | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Thu., 2/2 | JV Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 8:00 p.m. | 6:45 PM | |
| Thu., 2/2 | V Girls Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, Norwalk, Ridgefield, St. Joseph, Staples, Trumbull, Westhill, Wilton | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | 2:00 PM | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Fri., 2/3 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | W 62-33 | 4:15 PM | |
| Fri., 2/3 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | 2:15 PM | |
| Fri., 2/3 | FR Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | 2:15 PM | |
| Sat., 2/4 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | L 50-60 | 3:30 PM | |
| Sat., 2/4 | JV Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 3:00 p.m. | 3:30 PM | |
| Sat., 2/4 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | W 7-0 | ||
| Sat., 2/4 | V Wrestling | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 2/4 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 11:00 a.m. | 9:00 AM | |
| Sat., 2/4 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 4-3 | ||
| Mon., 2/6 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | W 8-1 | ||
| Tue., 2/7 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 54-44 | 4:00 PM | |
| Tue., 2/7 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Tue., 2/7 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Tue., 2/7 | V Wrestling | Ridgefield | Away - Ridgefield HS-Aux Gym [Directions] | 6:00 p.m. | 4:00 PM | |
| Tue., 2/7 | V Girls Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 50-42 | ||
| Tue., 2/7 | JV Girls Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Girls Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Staples | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 5-2 | ||
| Wed., 2/8 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 1-0 | ||
| Thu., 2/9 | V Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | L 46-44 | 2:15 PM | |
| Thu., 2/9 | JV Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Thu., 2/9 | Unified Sports Basketball | Westhill | Away - Westhill HS-New Gym [Directions] | 3:00 p.m. | 2:15 PM (2 Buses) | |
| Fri., 2/10 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | 2:45 PM | |
| Fri., 2/10 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Fri., 2/10 | V Boys Swimming and Diving | Danbury | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/10 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:00 p.m. | 2:30 PM | |
| Fri., 2/10 | JV Girls Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Wilton | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 7-0 | ||
| Sat., 2/11 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/11 | V Wrestling | FCIAC Finals | Away - Not Listed-New Canaan | TBA | 8:00 AM | |
| Sat., 2/11 | V Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | L 26-53 | 9:00 AM | |
| Sat., 2/11 | JV Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 12:30 p.m. | 9:00 AM | |
| Sat., 2/11 | FR Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 11:00 a.m. | 9:00 AM | |
| Sat., 2/11 | V Competitive Cheerleading | Watertown Cheer Open | Away - Not Listed-Watertown | TBA | 7:45 AM | |
| Sat., 2/11 | V Girls Gymnastics | FCIACs | Away - Not Listed-GCA Gymnastics | 10:00 a.m. | 8:30 AM | |
| Sat., 2/11 | V Girls Ice Hockey | Simsbury | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 2-1 | ||
| Sat., 2/11 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 75-72 3OT | ||
| Mon., 2/13 | JV Boys Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 24-40 | 4:00 PM | |
| Mon., 2/13 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Mon., 2/13 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 2/15 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 46-45 | 5:00 PM | |
| Wed., 2/15 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | 2:45 PM | |
| Wed., 2/15 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Wed., 2/15 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 5-4 | ||
| Wed., 2/15 | V Girls Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 48-45 | Senior Knight | |
| Wed., 2/15 | JV Girls Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Girls Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/17 | V Wrestling | CIAC LL Championship | Away - Trumbull | 4:00 p.m. | 11:30 AM | |
| Fri., 2/17 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | L 3-0 | 5:00 PM ((with stop for Staples at Exit 18)) | |
| Sat., 2/18 | V Boys Ice Hockey | Hall | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-1 | ||
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC LL Championship | Away - Trumbull | 10:30 a.m. | 8:00 AM | |
| Sat., 2/18 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 1-0 | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 72-47 | ||
| Mon., 2/20 | JV Boys Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 2:30 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | North Haven | Away - Northford-Red [Directions] | L 2-1 | ||
| Wed., 2/22 | V Boys Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 42-53 | ||
| Wed., 2/22 | JV Boys Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/22 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:40 p.m. | 6:15 PM | |
| Thu., 2/23 | Unified Sports Basketball | Vs, Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:00 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | 11:00 AM | |
| Sat., 2/25 | V Boys Basketball | Danbury | Away - Fairfield Warde HS-Gym [Directions] | 12:00 p.m. | 10:00 AM | |
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | TBA (Parent Provided Transportation) | |
| Sat., 2/25 | V Competitive Cheerleading | Oxford Spirit Spectacular | Away - Not Listed-Oxford | 9:30 a.m. | 8:15 AM | |
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | ||
| Mon., 2/27 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:00 p.m. | 2:45 PM | |
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Wed., 3/1 | V Girls Ice Hockey | Simsbury | Away - Simsbury - ISCC-NHL [Directions] | 5:00 p.m. | 12:45 PM (Coach Bus - Depart WHS at 12:45 to SHS. Depart SHS at 1:05 to Exit 18 then to Simsbury. Return trip with drop at Exit 18 (if needed) and SHS only.) | |
| Thu., 3/2 | V Boys Ice Hockey | Wilton | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | ||
| Thu., 3/2 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 4:00 p.m. | 12:30 PM (Pick up At WHS at 12:30. -> Pick up at SHS at 12:45 -> Stop at Staples -> Newington) | |
| Thu., 3/2 | Unified Sports Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:15 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | Greenwich, Danbury, Darien, Farfield Ludlowe/Warde, Fairfield Warde, TBA, New Canaan, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Sat., 3/4 | V Boys Ice Hockey | Trumbull | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | ||
| Sat., 3/4 | V Competitive Cheerleading | State Open Championships | Away - Not Listed-Floyd Little Athletic Center | 9:00 p.m. | 7:45 AM | |
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Tue., 3/7 | V Boys Basketball | SMSA | Away - SMSA-Gym [Directions] | 6:30 p.m. | 3:30 PM | |
| Tue., 3/7 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | ||
| Thu., 3/9 | V Boys Basketball | Guilford | Away - Guilford HS-Aux gym at GHS [Directions] | 6:30 p.m. | 3:00 PM | |
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/10 | V Boys Ice Hockey | Woodstock Academy | Away - Koeppel Community Sports Center - Trinity College-Albert Creighton Williams '64 Rink [Directions] | 6:00 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 4:30 p.m. | ||
| Mon., 3/13 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:30 p.m. | 3:45 PM | |
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Cornerstone Pool | 1:30 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Sat., 3/18 | V Competitive Cheerleading | New England Regionals | Home - Not Listed [Directions] | TBA | TBA | |
| Thu., 3/23 | V Softball | Weston (Scrim.) | Away - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 3/24 | V Baseball | Greenwich (Scrim.) | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Newtown (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 10:20 a.m. | 8:15 AM, Dismiss TBA | |
| Sat., 3/25 | V Boys Lacrosse | Amity (Scrim.) | Home - Shelton HS-Finn Stadium [Directions] | 11:10 a.m. | 8:15 AM, Dismiss TBA | |
| Sat., 3/25 | V Boys Lacrosse | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 9:30 a.m. | 8:15 AM, Dismiss TBA | |
| Sat., 3/25 | V Softball | TBA | Away - TBA | Cancelled | 8:45 AM | |
| Sat., 3/25 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS - Softball - JV Field [Directions] | Cancelled | ||
| Sun., 3/26 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 9:00 a.m. | 7:45 AM (JV & V) | |
| Sun., 3/26 | JV Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 9:00 a.m. | 7:45 AM (JV & V) | |
| Sun., 3/26 | V Girls Lacrosse | New Milford/Danbury Girls Lacrosse Preseason Play Day (first game at 9:30) | Away - New Milford HS-Joe Wiser Stadium - NMHS | 9:00 a.m. | 7:45 AM | |
| Sun., 3/26 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | W 9-6 | 9:45 AM | |
| Tue., 3/28 | V Baseball | Wright Tech (Scrim.) | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 3/28 | V Girls Lacrosse | Newtown (Scrim.) | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 3/29 | JV Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:15 p.m. | 2:30 PM (JV & V) | |
| Wed., 3/29 | FR Baseball | Norwalk (Scrim.) | Away - City Hall Field [Directions] | 4:15 p.m. | 2:30 PM (JV & V) | |
| Wed., 3/29 | V Softball | Bunnell (Scrim.) | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 4:15 p.m. | 2:30 PM | |
| Thu., 3/30 | V Baseball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Sat., 4/1 | V Boys Lacrosse | Foran (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/1 | FR Boys Lacrosse | Conard | Home - Stamford HS-Upper Lacrosse Field [Directions] | 12:00 p.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Rockville | Home - Stamford HS-Boyle Stadium [Directions] | W 15-5 | ||
| Sun., 4/2 | V Baseball | Cheshire | Home - Stamford HS-SHS Baseball Diamond [Directions] | L 0-1 | ||
| Mon., 4/3 | V Baseball | New Milford | Away - New Milford HS-Baseball Varsity Field - NMHS [Directions] | W 6-3 | 2:30 PM (JV & V) | |
| Mon., 4/3 | JV Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | L 5-13 | 2:30 PM (JV & V) | |
| Mon., 4/3 | FR Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/3 | V Girls Lacrosse | Weston | Home - Stamford HS-Boyle Stadium [Directions] | L 5-17 | ||
| Mon., 4/3 | JV Girls Lacrosse | Weston | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/3 | V Softball | New Fairfield | Home - Stamford HS-SHS Softball Diamond [Directions] | W 13-3 | ||
| Tue., 4/4 | V Boys Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | W 21-2 | ||
| Tue., 4/4 | JV Boys Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 4:15 p.m. | ||
| Tue., 4/4 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 4/4 | V Softball | Lauralton Hall | Away - Lauralton Hall-Softball Varsity Diamond [Directions] | L 8-4 | 2:30 PM | |
| Wed., 4/5 | V Baseball | Weston | Home - Stamford HS-SHS Baseball Diamond [Directions] | L 13-11 | ||
| Wed., 4/5 | JV Baseball | Weston | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | W 10-3 | ||
| Wed., 4/5 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | L 0-3 | 2:00 PM | |
| Thu., 4/6 | V Boys Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | L 13-6 | ||
| Thu., 4/6 | JV Boys Lacrosse | Brien McMahon | Home - Stamford HS-Upper Lacrosse Field [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Postponed | 3:15 PM | |
| Thu., 4/6 | V Boys Volleyball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-1 | ||
| Thu., 4/6 | JV Boys Volleyball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-2 | ||
| Thu., 4/6 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 10-8 | 2:30 PM | |
| Thu., 4/6 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:15 p.m. | 2:30 PM | |
| Sat., 4/8 | V Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 4-1 | ||
| Sat., 4/8 | JV Baseball | Greenwich | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | L 7-14 | ||
| Sat., 4/8 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 15-5 | 9:00 AM | |
| Sat., 4/8 | JV Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 12:30 p.m. | 10:30 AM | |
| Sat., 4/8 | V Girls Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | W 14-5 | ||
| Sat., 4/8 | JV Girls Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/8 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | L 8-0 | 8:45 AM | |
| Sat., 4/8 | JV Softball | Amity | Away - Amity Regional HS-CENTER FIELD [Directions] | Cancelled | 8:45 AM | |
| Mon., 4/10 | V Baseball | Norwalk | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 10-9 | ||
| Mon., 4/10 | JV Baseball | Norwalk | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | L 3-4 | ||
| Mon., 4/10 | FR Boys Lacrosse | Staples | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Vs Staples #2 | |
| Mon., 4/10 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:30 PM | |
| Mon., 4/10 | V Softball | Staples | Home - Stamford HS-SHS Softball Diamond [Directions] | W 7-3 | ||
| Mon., 4/10 | V Girls Tennis | St. Joseph | Home - Stamford HS-SHS Tennis Courts [Directions] | L 3 [Detailed Results] | ||
| Tue., 4/11 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 19-7 | 3:15 PM | |
| Tue., 4/11 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | 3:15 PM | |
| Tue., 4/11 | V Boys Outdoor Track | Westhill | Away - Westhill HS-Upper Grass Field [Directions] | 3:00 p.m. | 2:00 PM | |
| Tue., 4/11 | V Boys Tennis | Brien McMahon | Home - Stamford HS-SHS Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Tue., 4/11 | V Boys Volleyball | HMTCA | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Tue., 4/11 | V Girls Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | L 1-16 | ||
| Tue., 4/11 | JV Girls Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/11 | V Girls Outdoor Track | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | 2:00 PM | Jump and Field Events Only |
| Tue., 4/11 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | L 3 [Detailed Results] | 2:30 PM | |
| Wed., 4/12 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | 3:45 PM | |
| Wed., 4/12 | V Boys Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | Running events only | |
| Wed., 4/12 | V Girls Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | Running events only | |
| Wed., 4/12 | V Softball | Fairfield Warde | Home - Stamford HS-SHS Softball Diamond [Directions] | W 7-6 | ||
| Thu., 4/13 | V Boys Tennis | Danbury | Home - Stamford HS-SHS Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Thu., 4/13 | V Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 2-3 | ||
| Thu., 4/13 | JV Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-2 | ||
| Thu., 4/13 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | W 7 [Detailed Results] | 2:30 PM | |
| Fri., 4/14 | V Baseball | St. Joseph | Home - Stamford HS-SHS Baseball Diamond [Directions] | L 11-1 | ||
| Fri., 4/14 | JV Baseball | St. Joseph | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | W 9-5 | ||
| Fri., 4/14 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:30 p.m. | 2:30 PM (Varsity Softball and Fr. Baseball are sharing a bus to St. Joes) | |
| Fri., 4/14 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | 2:45 PM | |
| Fri., 4/14 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | W 12-6 | 1:45 PM | |
| Fri., 4/14 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | Cancelled | 1:45 PM | |
| Fri., 4/14 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | L 21-2 | 2:30 PM (Varsity Softball and Fr. Baseball are sharing a bus to St. Joes) | |
| Sat., 4/15 | V Boys Lacrosse | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | W 14-3 | 10:00 AM | |
| Sat., 4/15 | JV Boys Lacrosse | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 1:30 p.m. | 11:30 AM | |
| Sat., 4/15 | JV Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 10:30 a.m. | 8:45 AM | |
| Mon., 4/17 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | W 7-0 | 2:30 PM (JV & V) | |
| Mon., 4/17 | JV Baseball | Brien McMahon | Away - City Hall Field [Directions] | W 8-1 | 2:30 PM (JV & V) | |
| Mon., 4/17 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/17 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | L 1-6 [Detailed Results] | 2:30 PM | |
| Mon., 4/17 | JV Boys Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | L 2-1 | 2:45 PM | |
| Mon., 4/17 | V Softball | Brien McMahon | Home - Stamford HS-SHS Softball Diamond [Directions] | W 7-1 | ||
| Tue., 4/18 | V Boys Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | L 16-3 | ||
| Tue., 4/18 | JV Boys Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 4/18 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | L 8-9 | 2:30 PM | |
| Tue., 4/18 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:30 p.m. | 2:30 PM | |
| Tue., 4/18 | V Girls Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 4/18 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | L 1 [Detailed Results] | 2:30 PM | |
| Wed., 4/19 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | L 2-1 | 2:30 PM (JV & V) | |
| Wed., 4/19 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | L 11-13 | 2:30 PM (JV & V) | |
| Wed., 4/19 | FR Baseball | Danbury | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 3-1 | 2:30 PM | |
| Wed., 4/19 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 2-0 | 2:30 PM | |
| Wed., 4/19 | V Softball | Danbury | Home - Stamford HS-SHS Softball Diamond [Directions] | W 6-3 | ||
| Wed., 4/19 | JV Softball | Danbury | Home - Cummings Park Field #4-Stamford JV Softball at Cummings Park [Directions] | 4:00 p.m. | 2:45 PM | |
| Wed., 4/19 | V Girls Tennis | Fairfield Warde | Home - Stamford HS-SHS Tennis Courts [Directions] | L 2 [Detailed Results] | ||
| Thu., 4/20 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | L 2-5 [Detailed Results] | 3:00 PM | |
| Thu., 4/20 | V Girls Tennis | New Canaan | Home - Stamford HS-SHS Tennis Courts [Directions] | L 00 [Detailed Results] | ||
| Fri., 4/21 | V Baseball | Fairfield Warde | Home - Stamford HS-SHS Baseball Diamond [Directions] | L 16-2 | ||
| Fri., 4/21 | JV Baseball | Fairfield Warde | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | L 1 - 13 | ||
| Fri., 4/21 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 4/21 | FR Boys Lacrosse | Fairfield Warde | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 4/21 | V Boys Tennis | Wilton | Home - Stamford HS-SHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Fri., 4/21 | V Boys Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 1-3 | ||
| Fri., 4/21 | JV Boys Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-2 | ||
| Fri., 4/21 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | W 9-8 | 2:30 PM | |
| Sat., 4/22 | V Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | L 9-5 | 8:45 AM | |
| Sat., 4/22 | JV Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 9:00 a.m. | 7:30 AM | |
| Sat., 4/22 | V Girls Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | W 15-5 | ||
| Sat., 4/22 | JV Girls Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/22 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 10:00 a.m. | 8:15 AM | |
| Mon., 4/24 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | W 1-0 | 2:30 PM (JV & V) | |
| Mon., 4/24 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | L 5 - 7 | 2:30 PM (JV & V) | |
| Mon., 4/24 | FR Baseball | Wilton | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | 3:15 PM | |
| Mon., 4/24 | V Boys Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/24 | V Boys Tennis | Ridgefield | Home - Stamford HS-SHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Mon., 4/24 | V Boys Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Mon., 4/24 | JV Boys Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-2 | ||
| Mon., 4/24 | V Girls Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/24 | V Softball | Wilton | Home - Troy Complex-Diamond 1 [Directions] | L 5-4 | ||
| Mon., 4/24 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | L 2 [Detailed Results] | 2:30 PM | |
| Tue., 4/25 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Mastroni Field [Directions] | W 16-12 | 3:00 PM | |
| Tue., 4/25 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Mastroni Field [Directions] | 7:00 p.m. | 4:30 PM | |
| Tue., 4/25 | V Boys Tennis | Trumbull | Home - Stamford HS-SHS Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Tue., 4/25 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | L 3-2 | 2:30 PM (JV & Varsity together) | |
| Tue., 4/25 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 6:30 p.m. | 2:30 PM (JV & V together) | |
| Tue., 4/25 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | W 5 [Detailed Results] | 2:30 PM | |
| Wed., 4/26 | FR Boys Lacrosse | Greenwich | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Tier #2 Greenwich | |
| Wed., 4/26 | V Boys Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 2-3 | ||
| Wed., 4/26 | JV Boys Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-2 | ||
| Thu., 4/27 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | L 9-8 | 5:00 PM | |
| Thu., 4/27 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | 3:00 PM | |
| Thu., 4/27 | V Girls Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | W 9-8 | ||
| Thu., 4/27 | JV Girls Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/28 | V Baseball | Ridgefield | Away - Governor Field [Directions] | L 10-0 | 2:30 PM (JV and V together) | |
| Fri., 4/28 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | W 13 - 5 | 2:30 PM (JV and V together) | |
| Fri., 4/28 | FR Baseball | Ridgefield | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Boys Lacrosse | Westhill | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 4/28 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 0-3 | 3:00 PM | |
| Fri., 4/28 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 2-0 | 3:00 PM | |
| Fri., 4/28 | V Softball | Ridgefield | Home - Stamford HS-SHS Softball Diamond [Directions] | L 4-2 | ||
| Fri., 4/28 | JV Softball | Ridgefield | Home - Cummings Park Field #4-Stamford JV Softball at Cummings Park [Directions] | 4:30 p.m. | 2:45 PM | |
| Sat., 4/29 | V Boys Lacrosse | Immaculate | Away - Immaculate HS [Directions] | W 7-1 | 11:00 AM | |
| Sat., 4/29 | V Girls Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | W 15-2 | 9:00 AM | |
| Sat., 4/29 | JV Softball | Wilton | Home - Stamford HS-SHS Softball Diamond [Directions] | Postponed | ||
| Mon., 5/1 | V Boys Lacrosse | Brookfield | Home - Stamford HS-Boyle Stadium [Directions] | W 10-5 | ||
| Mon., 5/1 | JV Boys Lacrosse | Brookfield | Home - Stamford HS-Upper Lacrosse Field [Directions] | Cancelled | ||
| Mon., 5/1 | FR Boys Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | 5:00 p.m. | 2:30 PM | |
| Mon., 5/1 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | L 2-5 [Detailed Results] | 2:30 PM | |
| Mon., 5/1 | V Boys Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Mon., 5/1 | JV Boys Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-2 | ||
| Mon., 5/1 | V Softball | Trumbull | Home - Stamford HS-SHS Softball Diamond [Directions] | L 2-8 | ||
| Mon., 5/1 | JV Softball | Trumbull | Home - Cummings Park Field #4-Stamford JV Softball at Cummings Park [Directions] | 4:00 p.m. | 2:45 PM | |
| Mon., 5/1 | V Girls Tennis | Staples | Home - Stamford HS-SHS Tennis Courts [Directions] | L 00 [Detailed Results] | ||
| Tue., 5/2 | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 5/2 | V Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 18-7 | 2:45 PM | |
| Tue., 5/2 | JV Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | 2:45 PM | |
| Tue., 5/2 | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 5/3 | V Baseball | Fairfield Ludlowe | Home - Stamford HS-SHS Baseball Diamond [Directions] | L 8-0 | ||
| Wed., 5/3 | JV Baseball | Fairfield Ludlowe | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | L 2 - 6 | ||
| Wed., 5/3 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:30 p.m. | 2:30 PM (JV Softball and Freshman Baseball share a bus to same location) | |
| Wed., 5/3 | FR Boys Lacrosse | Wilton | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Wilton Team #2 | |
| Wed., 5/3 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | L 1-6 [Detailed Results] | 3:00 PM | |
| Wed., 5/3 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | L 1-3 | 2:30 PM | |
| Wed., 5/3 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | L 2-0 | 2:30 PM | |
| Wed., 5/3 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | L 0-16 | 2:30 PM (Varsity only) | |
| Wed., 5/3 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden Field [Directions] | 4:30 p.m. | 2:30 PM (JV Softball and Freshman Baseball share a bus to same location) | |
| Wed., 5/3 | V Girls Tennis | Westhill | Home - Stamford HS-SHS Tennis Courts [Directions] | L 3 [Detailed Results] | ||
| Thu., 5/4 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | L 7-6 | 2:30 PM (JV & V) | |
| Thu., 5/4 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | L 5 - 6 | 2:30 PM (Jv and V together) | |
| Thu., 5/4 | FR Baseball | Trumbull | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Tennis | Norwalk | Home - Stamford HS-SHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Thu., 5/4 | V Girls Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | W 12-7 | ||
| Thu., 5/4 | JV Girls Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | W 6 [Detailed Results] | 2:45 AM | |
| Fri., 5/5 | V Baseball | Staples | Home - Stamford HS-SHS Baseball Diamond [Directions] | L 8-0 | ||
| Fri., 5/5 | JV Baseball | Staples | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | L 1 - 11 | ||
| Fri., 5/5 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | Postponed | 2:30 PM | |
| Fri., 5/5 | FR Boys Lacrosse | Newtown | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 5/5 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | 2:30 PM | |
| Fri., 5/5 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 2:45 PM | |
| Fri., 5/5 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 2-0 | 2:45 PM | |
| Fri., 5/5 | V Softball | Staples | Away - Greens Farms Elementary School-Softball Field [Directions] | L 6-7 | 4:30 PM | |
| Fri., 5/5 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | Postponed | 2:30 PM (JV & V) | |
| Sat., 5/6 | V Baseball | New Canaan | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 11-6 | ||
| Sat., 5/6 | JV Baseball | New Canaan | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | L 10 - 24 | ||
| Sat., 5/6 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | Postponed | 9:30 AM | |
| Sat., 5/6 | V Boys Lacrosse | Masuk | Home - Stamford HS-Boyle Stadium [Directions] | W 9-4 | ||
| Sat., 5/6 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | Cancelled | 12:00 PM (Parent drop off and pick up at WHS) | |
| Sat., 5/6 | V Girls Tennis | Fairfield Ludlowe | Home - Stamford HS-SHS Tennis Courts [Directions] | L 00 [Detailed Results] | ||
| Sun., 5/7 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | L 6-1 | TBA (Parent Drop off and Pick up) | |
| Mon., 5/8 | V Baseball | Westhill | Home - Cubeta Stadium [Directions] | L 7-4 | ||
| Mon., 5/8 | JV Baseball | Westhill | Home - Cubeta Stadium [Directions] | L 3 - 7 | 2:15 PM (A bus will be provided to get the JV team Cubeta and will be provided to anyone that wants to take it back to the school after the JV (should they not wish to stay for the varsity game).) | |
| Mon., 5/8 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Mon., 5/8 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Mon., 5/8 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:45 PM | |
| Mon., 5/8 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | L 0-3 | 2:45 PM | |
| Mon., 5/8 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | L 2-0 | 2:45 PM | |
| Mon., 5/8 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 0-20 | 2:30 PM | |
| Mon., 5/8 | JV Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | 2:30 PM | |
| Mon., 5/8 | V Girls Tennis | Darien | Home - Stamford HS-SHS Tennis Courts [Directions] | L 00 [Detailed Results] | ||
| Tue., 5/9 | V Boys Lacrosse | Darien | Home - Stamford HS-Boyle Stadium [Directions] | L 19-1 | ||
| Tue., 5/9 | JV Boys Lacrosse | Darien | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | 3:00 PM | |
| Tue., 5/9 | V Boys Tennis | Bridgeport Central | Home - Stamford HS-SHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Tue., 5/9 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | 3:00 PM | |
| Tue., 5/9 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 6 [Detailed Results] | 2:30 PM | |
| Wed., 5/10 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | L 9-3 | 4:00 PM | |
| Wed., 5/10 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | L 2 - 9 | 2:30 PM | |
| Wed., 5/10 | FR Baseball | Norwalk | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Boys Lacrosse | Trumbull | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Trumbull Team #2 | |
| Wed., 5/10 | V Boys Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 1-3 | ||
| Wed., 5/10 | V Softball | Norwalk | Home - Troy Complex-Diamond 1 [Directions] | L 6-2 | ||
| Wed., 5/10 | JV Softball | Norwalk | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Baseball | Darien | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 6-5 | ||
| Thu., 5/11 | JV Baseball | Darien | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | L 4 - 12 | ||
| Thu., 5/11 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | 2:30 PM (V Softball and Fr Baseball) | |
| Thu., 5/11 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 12-7 | 4:00 PM | |
| Thu., 5/11 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 5/11 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | L 1-6 [Detailed Results] | 3:15 PM | |
| Thu., 5/11 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | L 0-3 | 2:45 PM | |
| Thu., 5/11 | V Girls Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | L 10-18 | Senior Knight | |
| Thu., 5/11 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | W 3-1 | 2:30 PM (V Softball and Fr Baseball) | |
| Thu., 5/11 | V Girls Tennis | Greenwich | Home - Stamford HS-SHS Tennis Courts [Directions] | L 00 [Detailed Results] | ||
| Sat., 5/13 | V Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | L 4-8 | ||
| Sat., 5/13 | JV Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Sat., 5/13 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | L 8-11 | 12:00 PM | |
| Sat., 5/13 | JV Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 1:30 p.m. | 12:00 PM | |
| Mon., 5/15 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | W 12-0 | 2:30 PM | |
| Mon., 5/15 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Ludlowe Team #2 | |
| Mon., 5/15 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 0-3 | 2:30 PM | |
| Mon., 5/15 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 2-1 | 2:30 PM | |
| Mon., 5/15 | V Softball | Bridgeport Central | Home - Troy Complex-Diamond 1 [Directions] | W 20-0 | ||
| Tue., 5/16 | V Boys Lacrosse | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | L 10-7 | ||
| Tue., 5/16 | JV Boys Lacrosse | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 5/16 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 11-5 | 4:15 PM | |
| Tue., 5/16 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 5/16 | V Girls Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 5/17 | V Baseball | Greenwich | Home - Cubeta Stadium [Directions] | W 3-0 | ||
| Wed., 5/17 | JV Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:00 p.m. | 2:45 PM (V Softball & Fr Baseball) | |
| Wed., 5/17 | V Boys Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Wed., 5/17 | JV Boys Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-2 | ||
| Wed., 5/17 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | W 14-0 | 3:00 PM | |
| Wed., 5/17 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | 3:00 PM (JV on their own bus due to off site game) | |
| Thu., 5/18 | FR Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/18 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 1-19 | 2:30 PM | |
| Thu., 5/18 | JV Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Sat., 5/20 | V Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | L 0-3 | 9:00 AM | |
| Sat., 5/20 | JV Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | L 2-1 | 9:00 AM | |
| Tue., 5/23 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:30 p.m. | 2:30 PM | |
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Track Championship | Away - Danbury HS-Danbury HS Stadium | 2:30 p.m. | 12:00 PM | |
| Tue., 5/23 | V Girls Outdoor Track | FCIAC Track Championship | Away - Danbury HS-DHS Stadium | 2:30 p.m. | 12:00 PM | |
| Wed., 5/24 | V Baseball | Fairfield Ludlowe (Scrim.) | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 5/24 | V Softball | New Canaan (Scrim.) | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Fri., 5/26 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 5/26 | V Girls Lacrosse | South Windsor | Home - Stamford HS-Boyle Stadium [Directions] | W 11-5 | ||
| Sat., 5/27 | V Boys Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | W 9-8 | 11:00 AM | |
| Tue., 5/30 | V Baseball | South Windsor | Away - Nevers Road Park-Rotary Field (90 ft. - Lighted) [Directions] | L 4-3 | 2:00 PM | |
| Tue., 5/30 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 5/30 | V Softball | Maloney | Away - Dunn Sports Complex-Dunn Sports Complex (pinwheel) [Directions] | W 7-6 | 3:00 PM | |
| Wed., 5/31 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 23-2 | 4:30 PM | |
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | 7:30 AM | |
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | 7:30 AM | |
| Wed., 5/31 | V Softball | Danbury | Home - Stamford HS-SHS Softball Diamond [Directions] | L 4-3 | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||