| Stamford 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 517 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 | V Girls Soccer | Stratford (Scrim.) | Away - Penders Field-Penders Field - Stratford [Directions] | 4:00 p.m. | ||
| 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. | ||
| Wed., 9/7 | V Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | L 2-1 | 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 | |
| Fri., 9/9 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | L 8-1 | 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 | 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 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | L 3-0 | 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 | ||
| 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 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 2-0 | 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 | ||
| 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 | |
| Fri., 9/16 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 27-54 | 3:45 PM (2 buses) | |
| 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 | ||
| 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 | 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 | V Girls Soccer | Fairfield Warde | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 5-1 | ||
| 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 | ||
| 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 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | L 3-0 | 3:30 PM | |
| Wed., 9/21 | V Boys Golf | Trumbull | Home - Stamford High-Sterling Farms Golf Course [Directions] | Trumbull 162, Stamford 195 | ||
| Thu., 9/22 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 1-0 | 5:15 PM | |
| Thu., 9/22 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 3-0 | 2:15 PM | |
| Fri., 9/23 | V Field Hockey | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | L 3-1 | ||
| Fri., 9/23 | V Girls Soccer | New Canaan | Home - Stamford HS-SHS Upper Soccer Field [Directions] | T 1-1 | ||
| 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 | ||
| 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 | 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 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 3-0 | 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 | ||
| 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 | ||
| Fri., 9/30 | V Boys Soccer | Trumbull | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 3-2 | ||
| Fri., 9/30 | V Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | W 2-0 | 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 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 3-1 | 12:45 PM | |
| 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 | 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 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| 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 | 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 | ||
| Fri., 10/7 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 0-2 | 2:45 PM | |
| Fri., 10/7 | V Girls Soccer | Fairfield Ludlowe | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 0-3 | ||
| 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 | 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 | |
| Mon., 10/10 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | L 2-0 | 2:00 PM | |
| Mon., 10/10 | V Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 3-2 | ||
| 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 | V Girls Soccer | Staples | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 1-4 | ||
| 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 | V Girls Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 3-0 | ||
| Thu., 10/13 | V Girls Soccer | Westhill | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 1-0 | ||
| 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 | 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 | 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 | |
| Sat., 10/15 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 4-2 | 2:30 PM | |
| 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 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | L 0-9 | 2:15 PM | |
| Mon., 10/17 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | L 3-0 | 2:45 PM | |
| 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 | ||
| 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 | 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 | |
| Thu., 10/20 | V Boys Soccer | Bridgeport Central | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 6-1 | ||
| Fri., 10/21 | V Field Hockey | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | W 1-0 | ||
| 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 | ||
| Sat., 10/22 | V Football | Staples | Home - Stamford HS-Boyle Stadium [Directions] | L 7-42 | ||
| Sat., 10/22 | V Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | L 3-1 | 7:30 AM | |
| Mon., 10/24 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 4-0 | 3:00 PM | |
| Mon., 10/24 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 2:30 PM | |
| Tue., 10/25 | V Field Hockey | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | W 3-0 | ||
| Tue., 10/25 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 7-1 | ||
| Thu., 10/27 | V Girls Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/28 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | L 0-3 | 3:00 PM | |
| 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. | ||
| 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 | |
| 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 | 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 | 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. | ||
| 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 | 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 | |
| Wed., 12/21 | V Boys Basketball | North Haven | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 65-40 | ||
| 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 | |
| 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 | ||
| Tue., 1/3 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 49-36 | 3:30 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 | 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 | ||
| 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 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 51-28 | 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 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 52-43 | 4:30 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 | V Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 45-53 | ||
| 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 | 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 | 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 | 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 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 50-39 | 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 | V Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 44-35 | ||
| 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 | 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 | V Girls Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 34-27 | ||
| 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 | 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 | 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 | |
| Sat., 2/4 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | L 50-60 | 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 | 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 | ||
| 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 | Unified Sports Basketball | Westhill | Away - Westhill HS-New Gym [Directions] | 3:00 p.m. | 2:15 PM (2 Buses) | |
| 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 | |
| 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 | 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 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 24-40 | 4:00 PM | |
| Wed., 2/15 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 46-45 | 5:00 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 | |
| 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 | 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 | 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 | 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 | 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 | 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 | V Girls Lacrosse | Weston | Home - Stamford HS-Boyle Stadium [Directions] | L 5-17 | ||
| 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 | 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 | 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 | V Boys Volleyball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-1 | ||
| Thu., 4/6 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 10-8 | 2:30 PM | |
| Sat., 4/8 | V Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 4-1 | ||
| Sat., 4/8 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 15-5 | 9:00 AM | |
| Sat., 4/8 | V Girls Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | W 14-5 | ||
| Sat., 4/8 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | L 8-0 | 8:45 AM | |
| Mon., 4/10 | V Baseball | Norwalk | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 10-9 | ||
| 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 | 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 | 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 | 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 | 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 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | W 12-6 | 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 | |
| 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 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | L 1-6 [Detailed Results] | 2:30 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 | 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 | 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 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 3-1 | 2:30 PM | |
| Wed., 4/19 | V Softball | Danbury | Home - Stamford HS-SHS Softball Diamond [Directions] | W 6-3 | ||
| 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 | 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 | 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 | V Girls Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | W 15-5 | ||
| Mon., 4/24 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | W 1-0 | 2:30 PM (JV & V) | |
| 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 | 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 | 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 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | W 5 [Detailed Results] | 2:30 PM | |
| Wed., 4/26 | V Boys Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 2-3 | ||
| Thu., 4/27 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | L 9-8 | 5:00 PM | |
| Thu., 4/27 | V Girls Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | W 9-8 | ||
| Fri., 4/28 | V Baseball | Ridgefield | Away - Governor Field [Directions] | L 10-0 | 2:30 PM (JV and V together) | |
| Fri., 4/28 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 0-3 | 3:00 PM | |
| Fri., 4/28 | V Softball | Ridgefield | Home - Stamford HS-SHS Softball Diamond [Directions] | L 4-2 | ||
| 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 | |
| Mon., 5/1 | V Boys Lacrosse | Brookfield | Home - Stamford HS-Boyle Stadium [Directions] | W 10-5 | ||
| 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 | V Softball | Trumbull | Home - Stamford HS-SHS Softball Diamond [Directions] | L 2-8 | ||
| 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 | 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 | 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 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | L 0-16 | 2:30 PM (Varsity only) | |
| 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 | 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 | 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 | 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 | V Softball | Staples | Away - Greens Farms Elementary School-Softball Field [Directions] | L 6-7 | 4:30 PM | |
| Sat., 5/6 | V Baseball | New Canaan | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 11-6 | ||
| Sat., 5/6 | V Boys Lacrosse | Masuk | Home - Stamford HS-Boyle Stadium [Directions] | W 9-4 | ||
| 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 | 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 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 0-20 | 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 | 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 | 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 | ||
| Thu., 5/11 | V Baseball | Darien | Home - Stamford HS-SHS Baseball Diamond [Directions] | W 6-5 | ||
| Thu., 5/11 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 12-7 | 4:00 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 | 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 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | L 8-11 | 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 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 0-3 | 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 | 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 | 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 | V Boys Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Wed., 5/17 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | W 14-0 | 3:00 PM | |
| Thu., 5/18 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 1-19 | 2:30 PM | |
| Sat., 5/20 | V Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | L 0-3 | 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. | ||