| Staples 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1163 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Wed., 8/23 | V Football | Fairfield Prep, TBA, Newtown, Wilton (Scrim.) | Away - Fairfield University-Barlow Field [Directions] | 3:00 p.m. | 1:15 PM | |
| Thu., 8/24 | FR Football | Fairfield Prep, Fairfield Ludlowe, Wilton (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 8/25 | Miscellaneous Events | Varsity football combined practice with Shelton High School | Home - Shelton HS-High School - Finn Stadium [Directions] | 5:00 p.m. | 3:15 PM | |
| Mon., 8/28 | V Boys Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Red Turf Field 2 | 4:00 p.m. | 2:45 PM | |
| Mon., 8/28 | V Girls Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Red Turf Field 2 | 10:00 a.m. | 8:45 AM | |
| Mon., 8/28 | FR Girls Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Grens Farm Academy Field 5 Grass | 10:00 a.m. | 8:45 AM | |
| Tue., 8/29 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 8/29 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Tammaro Field | 4:30 p.m. | ||
| Tue., 8/29 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Tammaro Field | 4:30 p.m. | 3:00 PM | |
| Tue., 8/29 | JV Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Stadium | 4:30 p.m. | 3:00 PM | |
| Wed., 8/30 | FR Football | Shelton (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 8/31 | V Football | Bunnell (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 8/31 | V Boys Golf | Ridgefield | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 8/31 | JV Boys Golf | Ridgefield | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 8/31 | V Boys Soccer | Fairfield Prep (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 8/31 | V Girls Soccer | Bethel (Scrim.) | Away - Bethel HS-MS Turf Soccer Field [Directions] | 4:00 p.m. | 2:20 PM, Dismiss 2:10 PM | |
| Thu., 8/31 | JV Girls Soccer | Bethel (Scrim.) | Away - Bethel HS-Rockwell Field [Directions] | 4:00 p.m. | 2:20 PM, Dismiss 2:10 PM | |
| Sat., 9/2 | V Boys Soccer | Wethersfield, Kingswood-Oxford, Tolland (Scrim.) | Away - Wethersfield HS-Cottone Field [Directions] | 10:00 a.m. | 7:45 AM | |
| Sat., 9/2 | V Girls Soccer | Blue and white intersquad game | Home - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | V Girls Volleyball | Wilton, King and Low-Heywood Thomas, Naugatuck, Northwest Catholic, St. Joseph | Away - Wilton HS-Nicholas Zeoli Field House | 9:00 a.m. | 7:30 AM | |
| Sat., 9/2 | Miscellaneous Events | Field Hockey Play day @ Sacred Heart Greenwich | Home - TBA [Directions] | 9:00 a.m. | 8:30 AM | |
| Mon., 9/4 | V Girls Soccer | Newtown (Scrim.) | Away - Newtown HS-Blue and Gold Stadium [Directions] | 10:00 a.m. | 8:15 AM | |
| Tue., 9/5 | V Field Hockey | Greenwich Academy (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Wed., 9/6 | V Boys Golf | Fairfield Prep | Home - Longshore Golf Course [Directions] | 3:20 p.m. | ||
| Wed., 9/6 | JV Boys Golf | Fairfield Prep | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/7 | FR Football | West Haven | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Thu., 9/7 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 2:15 PM, Dismiss 2:00 PM (JV/V going on same bus) | |
| Thu., 9/7 | JV Boys Golf | Trumbull | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Thu., 9/7 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | W 6-2 | 5:30 PM | |
| Thu., 9/7 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | Postponed | 4:00 PM | |
| Thu., 9/7 | FR Field Hockey | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Thu., 9/7 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | L 3-1 | 2:45 PM, Dismiss 2:30 PM (V/JV going together) | |
| Thu., 9/7 | JV Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM (V/JV going together) | |
| Fri., 9/8 | V Football | West Haven | Home - Staples HS-Staples Stadium [Directions] | L 23-33 | ||
| Fri., 9/8 | V Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Fri., 9/8 | JV Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/8 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Sat., 9/9 | V Boys Cross Country | Wilton Invitational - Boys Cross Country - Allen's Meadow | Away - Wilton HS | 9:00 a.m. | 7:00 AM; 2 Buses | |
| Sat., 9/9 | JV Football | Stratford | Home - Staples HS-Staples Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | V Girls Cross Country | Wilton Invitational - Girls Cross Country - Wilton High School | Away - Allen's Meadow | 9:00 a.m. | 7:00 AM | |
| Sat., 9/9 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | W 3-2 | 6:35 PM | |
| Sat., 9/9 | FR Girls Soccer | Ridgefield | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 10:00 a.m. | ||
| Mon., 9/11 | V Field Hockey | St. Joseph | Home - Staples HS-Ginny Parker Field [Directions] | W 7-0 | ||
| Mon., 9/11 | JV Field Hockey | St. Joseph | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Mon., 9/11 | V Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 3-0 | ||
| Mon., 9/11 | JV Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 9/11 | V Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | L 3-0 | ||
| Mon., 9/11 | JV Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | FR Girls Volleyball | Fairfield Warde | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Ridgefield, Fairfield Ludlowe, Greenwich | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:15 PM | |
| Tue., 9/12 | V Boys Golf | Danbury | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 9/12 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | W 2-0 | 5:00 PM | |
| Tue., 9/12 | JV Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | T 0-0 | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 9/12 | FR Boys Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Ridgefield, Fairfield Ludlowe, Greenwich | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:15 PM | |
| Tue., 9/12 | V Girls Swimming and Diving | Ridgefield | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | V Boys Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | Postponed | ||
| Wed., 9/13 | V Field Hockey | Westhill | Home - Staples HS-Ginny Parker Field [Directions] | W 10-0 | ||
| Wed., 9/13 | JV Field Hockey | Westhill | Home - Staples HS-Ginny Parker Field [Directions] | 5:45 p.m. | ||
| Wed., 9/13 | FR Field Hockey | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM | |
| Wed., 9/13 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | W 1-0 | 2:45 PM, Dismiss 2:30 PM | |
| Wed., 9/13 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | 4:10 PM | |
| Wed., 9/13 | V Girls Volleyball | Weston | Home - Staples HS-Staples Gym [Directions] | W 3-2 | ||
| Wed., 9/13 | JV Girls Volleyball | Weston | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | FR Girls Volleyball | Weston | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | Miscellaneous Events | Leadership Council Meeting | Home - Staples HS [Directions] | 7:30 p.m. | ||
| Thu., 9/14 | V Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | W 42-3 | ||
| Thu., 9/14 | FR Football | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 3:30 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Thu., 9/14 | V Boys Golf | Brien McMahon | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Brien McMahon | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 1-0 | ||
| Thu., 9/14 | JV Boys Soccer | Brien McMahon | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | 4:00 PM | |
| Thu., 9/14 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | T 0-0 | 2:30 PM | |
| Thu., 9/14 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Sat., 9/16 | Miscellaneous Events | Rosh Hashanah | Home - Staples HS [Directions] | TBA | ||
| Mon., 9/18 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | 4:00 PM | |
| Mon., 9/18 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 2-0 | 5:00 PM | |
| Mon., 9/18 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | 3:00 PM | |
| Tue., 9/19 | V Boys Cross Country | Danbury, Fairfield Warde, St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Golf | Westhill | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Norwalk | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 3-0 | ||
| Tue., 9/19 | JV Boys Soccer | Norwalk | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 9/19 | V Girls Cross Country | Danbury, Fairfield Warde, St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/19 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | W 4-1 | 2:15 PM, Dismiss 2:00 PM | |
| Tue., 9/19 | JV Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | 4:00 PM | |
| Tue., 9/19 | FR Field Hockey | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Boys Golf | New Canaan | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/20 | JV Boys Golf | New Canaan | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/20 | V Girls Soccer | Stamford | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 5-1 | ||
| Wed., 9/20 | JV Girls Soccer | Stamford | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Wed., 9/20 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:15 PM, Dismiss 1:00 PM | |
| Wed., 9/20 | Miscellaneous Events | Back To School Night-Grades 9 & 10 | Home - Staples HS [Directions] | 6:30 p.m. | ||
| Thu., 9/21 | FR Football | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 6:00 p.m. | 3:15 PM | |
| Thu., 9/21 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM (jv/v going together) | |
| Thu., 9/21 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM (JV/V GOING TOGETHER) | |
| Thu., 9/21 | V Boys Soccer | Stamford | Home - Staples HS-Wakeman Field B (turf) [Directions] | T 1-1 | ||
| Thu., 9/21 | JV Boys Soccer | Stamford | Away - Trinity Catholic-Alumni Field [Directions] | 4:30 p.m. | 2:45 PM | |
| Thu., 9/21 | FR Boys Soccer | Stamford | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Thu., 9/21 | V Field Hockey | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | W 10-0 | ||
| Thu., 9/21 | JV Field Hockey | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Thu., 9/21 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Cancelled | 2:45 PM | |
| Fri., 9/22 | V Football | Southington | Away - Southington HS-3 TURF FIELD [Directions] | W 34-27 | 3:15 PM, Dismiss 2:15 PM | |
| Fri., 9/22 | JV Boys Soccer | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM (going together with girls freshman soccer) | |
| Fri., 9/22 | V Boys Water Polo | Suffield Academy | Away - Suffield Academy | 4:00 p.m. | 1:15 PM, Dismiss 1:00 PM | |
| Fri., 9/22 | V Sideline Cheerleading | Football @ Southington | Away - Southington HS-3 TURF FIELD | 7:00 p.m. | 5:00 PM | |
| Fri., 9/22 | V Girls Soccer | Darien | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 4-0 | ||
| Fri., 9/22 | JV Girls Soccer | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM (going together with Boys JV soccer) | |
| Fri., 9/22 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | 1:15 PM, Dismiss 1:00 PM | |
| Fri., 9/22 | V Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Fri., 9/22 | JV Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Sat., 9/23 | V Boys Cross Country | Bowdoin Park XC Classic - Boys Cross Country | Away - Bowdoin Park-Wappingers Falls, NY | 10:00 a.m. | 6:30 AM; 2 Buses | |
| Sat., 9/23 | JV Football | Southington | Home - Staples HS-Staples Stadium [Directions] | 11:00 a.m. | ||
| Sat., 9/23 | V Girls Cross Country | Bowdin Invitational Girls Cross Country | Away - Bowdoin Park-Wappingers Falls, NY | 10:00 a.m. | 6:30 AM | |
| Sat., 9/23 | V Field Hockey | Ridge (NJ) | Home - The Proving Grounds-Field #1 [Directions] | W 2-1 | ||
| Sun., 9/24 | V Field Hockey | Gwynedd Mercy Academy (PA) | Home - The Proving Grounds-Field #1 [Directions] | L 1-2 | ||
| Mon., 9/25 | Miscellaneous Events | Yom Kippur | Home - Staples HS [Directions] | TBA | ||
| Tue., 9/26 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | 1:30 PM, Dismiss 1:15 PM | |
| Tue., 9/26 | V Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 2-0 | ||
| Tue., 9/26 | JV Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Tue., 9/26 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | Postponed | 2:15 PM | |
| Tue., 9/26 | V Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | 2:15 PM (J/v going together) | |
| Tue., 9/26 | JV Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:00 p.m. | ||
| Tue., 9/26 | V Girls Volleyball | Harding | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Tue., 9/26 | JV Girls Volleyball | Harding | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/27 | V Boys Cross Country | New Canaan, Trumbull, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM; 2 Buses | |
| Wed., 9/27 | V Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:30 p.m. | 2:00 PM | |
| Wed., 9/27 | JV Boys Golf | Darien | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/27 | V Girls Cross Country | New Canaan, Trumbull, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM | |
| Wed., 9/27 | FR Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM | |
| Wed., 9/27 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | T 2-2 | 2:15 PM, Dismiss 2:00 PM (v/jv going together) | |
| Wed., 9/27 | JV Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM (jv/v going together) | |
| Wed., 9/27 | FR Girls Soccer | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | W 3-0 | 2:15 PM, Dismiss 2:00 PM (JV/V going together) | |
| Wed., 9/27 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM (JV/V going together) | |
| Wed., 9/27 | Miscellaneous Events | Back To School Night-Grades 11 & 12 | Home - Staples HS [Directions] | 6:30 p.m. | ||
| Thu., 9/28 | FR Football | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/28 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | 2:15 PM, Dismiss 2:00 PM (jv/v going together) | |
| Thu., 9/28 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Thu., 9/28 | V Boys Soccer | Greenwich | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 2-0 | ||
| Thu., 9/28 | JV Boys Soccer | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Boys Soccer | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 5:00 p.m. | 3:30 PM | |
| Thu., 9/28 | V Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | W 7-0 | ||
| Thu., 9/28 | JV Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Thu., 9/28 | FR Girls Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/29 | FR Girls Soccer | Wilton | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Fri., 9/29 | V Girls Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Fri., 9/29 | JV Girls Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 49-0 | 10:15 AM | |
| Sat., 9/30 | V Boys Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 4-0 | ||
| Sat., 9/30 | JV Boys Soccer | Wilton | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Sat., 9/30 | FR Boys Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | Postponed | 9:45 AM | |
| Sat., 9/30 | V Sideline Cheerleading | Football@ Westhill | Away - Westhill HS | 1:00 p.m. | 11:45 AM | |
| Sat., 9/30 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 10-0 | 9:30 AM | |
| Sat., 9/30 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 9:00 a.m. | 7:30 AM | |
| Sat., 9/30 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | L 1-0 | 5:00 PM | |
| Sat., 9/30 | JV Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 9:00 a.m. | 2:45 PM | |
| Sat., 9/30 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 9:30 a.m. | 7:30 AM | |
| Sat., 9/30 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 9:00 a.m. | 7:45 AM | |
| Mon., 10/2 | V Boys Cross Country | Fairfield Ludlowe, Fairfield Warde, Trumbull | Away - Hoyden's Hill Open Space-Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | JV Football | Westhill | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/2 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | T 1-1 | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 10/2 | FR Boys Soccer | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Girls Cross Country | Fairfield Ludlowe, Fairfield Warde, Trumbull | Away - Hoyden's Hill Open Space-Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | OT-L 2-3 | 2:30 PM, Dismiss 2:15 PM (jv/v going together) | |
| Mon., 10/2 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/v going together) | |
| Mon., 10/2 | FR Field Hockey | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Bridgeport Central, Darien, Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Golf | Greenwich | Away - Round Hill Country Club [Directions] | 3:00 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Tue., 10/3 | V Girls Cross Country | Bridgeport Central, Darien, Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Bridgeport Central | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 7-0 | ||
| Tue., 10/3 | V Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Tue., 10/3 | JV Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | 3:15 PM | |
| Wed., 10/4 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Wed., 10/4 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | 2:00 PM, Dismiss 1:45 PM (jv/v going together) | |
| Wed., 10/4 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | W 5-0 | 4:45 PM | |
| Wed., 10/4 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium (Bridgeport) [Directions] | 4:30 p.m. | 3:00 PM | |
| Wed., 10/4 | V Field Hockey | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | W 6-1 | ||
| Wed., 10/4 | JV Field Hockey | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Wed., 10/4 | FR Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:30 p.m. | 4:10 PM | |
| Thu., 10/5 | V Boys Golf | Chappa Tournament | Home - Longshore Golf Course [Directions] | TBA | ||
| Thu., 10/5 | V Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 2-0 | ||
| Thu., 10/5 | JV Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | Cancelled | 2:30 PM | |
| Thu., 10/5 | V Girls Swimming and Diving | Westhill/Stamford | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 10/5 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | 2:30 PM, Dismiss 2:15 PM (JV/V going together) | |
| Thu., 10/5 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM (JV/V going together) | |
| Thu., 10/5 | FR Girls Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/6 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 3-0 | 4:30 PM | |
| Fri., 10/6 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Grass Utility Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 10/6 | FR Boys Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Girls Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/7 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 12:30 PM (JV/ Varsity going together) | |
| Sat., 10/7 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 3:30 p.m. | 12:30 PM (JV/ Varsity going together) | |
| Mon., 10/9 | V Boys Golf | Fairfield Ludlowe | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 10/9 | JV Boys Golf | Fairfield Ludlowe | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 10/9 | V Girls Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 3-1 | ||
| Mon., 10/9 | JV Girls Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:30 p.m. | 3:15 PM | |
| Mon., 10/9 | V Girls Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | L 0-3 | ||
| Mon., 10/9 | JV Girls Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/10 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:15 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Tue., 10/10 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 0-2 | 5:30 PM | |
| Tue., 10/10 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/10 | FR Boys Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | FR Girls Soccer | Bethel | Away - Bethel HS-Rockwell Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 10/11 | V Boys Cross Country | Wilton, Brien McMahon, Stamford | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 1:45 PM; 2 Buses | |
| Wed., 10/11 | FR Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 3:45 p.m. | 2:30 PM | |
| Wed., 10/11 | V Boys Water Polo | Suffield Academy | Home - Staples HS-Staples High School Pool [Directions] | Cancelled | ||
| Wed., 10/11 | V Girls Cross Country | Wilton, Brien McMahon, Stamford | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 1:45 PM | |
| Wed., 10/11 | V Girls Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 3:45 p.m. | 1:45 PM | |
| Wed., 10/11 | V Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Wed., 10/11 | JV Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | Miscellaneous Events | Leadership Council Meeting | Home - Staples HS [Directions] | 7:30 p.m. | ||
| Thu., 10/12 | FR Football | Wilton | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/12 | V Boys Soccer | Harding | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 6-0 | ||
| Thu., 10/12 | V Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | W 10-0 | ||
| Thu., 10/12 | JV Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Thu., 10/12 | FR Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | Postponed | 2:30 PM | |
| Thu., 10/12 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | W 2-1 | 3:45 PM | |
| Thu., 10/12 | JV Girls Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 10/12 | FR Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | FR Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 10/13 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | W 3-0 | 2:45 PM, Dismiss 2:30 PM (JV/ Varsity going together) | |
| Fri., 10/13 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM (JV/v going together) | |
| Sat., 10/14 | V Football | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | W 29-22 | 11:30 AM | |
| Sat., 10/14 | V Boys Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 1-0 | ||
| Sat., 10/14 | JV Boys Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 10:30 a.m. | ||
| Sat., 10/14 | V Boys Water Polo | Hopkins School | Away - Hopkins School | Cancelled | 1:30 PM | |
| Sat., 10/14 | V Sideline Cheerleading | Football @ Wilton | Away - Wilton HS | 2:00 p.m. | 12:45 PM | |
| Sat., 10/14 | JV Field Hockey | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | Postponed | ||
| Sat., 10/14 | FR Field Hockey | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 10:00 a.m. | 8:30 AM | |
| Mon., 10/16 | JV Football | Wilton | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/16 | V Boys Golf | Practice | Home - Tashua Knolls Golf Course [Directions] | 3-5 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Mon., 10/16 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 7-2 | 2:15 PM, Dismiss 2:00 PM | |
| Mon., 10/16 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Mon., 10/16 | FR Girls Soccer | Danbury | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 0-3 | 3:15 PM (JV/ Varsity going together) | |
| Mon., 10/16 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | 3:15 PM (JV/ Varsity going together) | |
| Mon., 10/16 | FR Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Danbury | Home - Staples HS-Wakeman Field B (turf) [Directions] | T 0-0 | ||
| Tue., 10/17 | JV Boys Soccer | Danbury | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/17 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 1-0 | 2:30 PM, Dismiss 2:15 AM | |
| Tue., 10/17 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | 4:00 PM | |
| Tue., 10/17 | FR Field Hockey | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | Miscellaneous Events | The Holahan - Woodway Golf Course - Boys V Golf | Home - TBA [Directions] | 12:00 p.m. | 11:00 AM | |
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:30 PM, Dismiss 12:00 PM | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | JV Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:00 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Wed., 10/18 | V Boys Water Polo | Choate Rosemary Hall, Hamden Hall | Away - Choate School | 4:30 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Wed., 10/18 | JV Boys Water Polo | Choate Rosemary Hall, Hamden Hall | Away - Choate School | 6:30 p.m. | TBA (JV/V going together) | |
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:30 PM, Dismiss 12:00 PM | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Soccer | St. Joseph | Home - Staples HS-Wakeman Field B (turf) [Directions] | T 1-1 | ||
| Wed., 10/18 | JV Girls Soccer | St. Joseph | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Girls Swimming and Diving | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 3-0 | 2:40 PM, Dismiss 2:25 PM (JV/ Varsity going together) | |
| Wed., 10/18 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 2:40 PM, Dismiss 2:25 PM (JV/ Varsity going together) | |
| Wed., 10/18 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | TBA | |
| Thu., 10/19 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | W 5-2 | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 10/19 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 4-0 | 2:15 PM, Dismiss 2:00 PM | |
| Thu., 10/19 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | 3:45 PM | |
| Thu., 10/19 | V Girls Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | L 1-3 | TBA | |
| Thu., 10/19 | JV Girls Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | TBA | |
| Thu., 10/19 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 4:45 PM | |
| Fri., 10/20 | V Football | Stamford | Home - Staples HS-Staples Stadium [Directions] | W 21-10 | ||
| Fri., 10/20 | V Field Hockey | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | W 2-1 | ||
| Sat., 10/21 | JV Football | Newtown | Home - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/21 | FR Girls Soccer | New Canaan, Trumbull | Away - Conner Field, New Cannan [Directions] | Postponed | 9:30 AM | |
| Mon., 10/23 | FR Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Westhill | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 7-0 | ||
| Mon., 10/23 | JV Girls Soccer | Westhill | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Tue., 10/24 | V Boys Cross Country | WIlton JV Invitational | Away - Allen's Meadow-XC Course | 4:00 p.m. | ||
| Tue., 10/24 | V Boys Golf | CIAC Division I Fall Championship | Away - Stanley GC | 8:30 a.m. | 5:30 AM | |
| Tue., 10/24 | V Boys Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | W 4-3 | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/24 | JV Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Tue., 10/24 | FR Boys Soccer | Westhill | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Tue., 10/24 | V Girls Cross Country | Wilton JV Invitational | Away - Allen's Meadow-XC Course | 4:00 p.m. | TBA | |
| Tue., 10/24 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | W 2-1 | 3:15 PM | |
| Tue., 10/24 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | 4:45 PM | |
| Tue., 10/24 | V Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | W 3-0 | 3:15 PM (JV/ Varsity going together) | |
| Tue., 10/24 | JV Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 4:45 p.m. | 3:15 PM (JV/ Varsity going together) | |
| Wed., 10/25 | V Girls Swimming and Diving | Trumbull | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 1-3 | 2:30 PM, Dismiss 2:15 PM, Return 7:15 PM (JV/ Varsity going together) | |
| Wed., 10/25 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | 2:45 PM, Dismiss 2:30 PM (JV/ Varsity going together) | |
| Wed., 10/25 | FR Girls Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 4-2 | FCIAC Tournament-Quarterfinals | |
| Thu., 10/26 | Miscellaneous Events | Freshman Girls and Boys XC Meet - Terry While Park - Danbury | Home - TBA [Directions] | 3:00 p.m. | 1:45 PM (dismiss at 1:15pm) | |
| Fri., 10/27 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 51-0 | 4:15 PM | |
| Fri., 10/27 | V Boys Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 4-1 | FCIAC Quarterfinals | |
| Fri., 10/27 | V Sideline Cheerleading | Football @ Danbury | Away - Danbury HS-Stadium turf field | 7:00 p.m. | 5:30 PM | |
| Fri., 10/27 | V Field Hockey | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | W 7-3 | FCIAC Quarterfinals | |
| Fri., 10/27 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 3-2 | 3:00 PM (JV/ Varsity going together) | |
| Fri., 10/27 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | 3:00 PM (JV/ Varsity going together) | |
| Fri., 10/27 | FR Girls Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/28 | JV Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 9:30 a.m. | 7:30 AM | |
| Mon., 10/30 | JV Football | Danbury | Home - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | ||
| Mon., 10/30 | V Boys Golf | New England Boys Golf Championship | Away - Mohegan Sun Golf Club | 9:00 a.m. | 5:30 AM | |
| Mon., 10/30 | V Boys Soccer | Stamford | Home - Fairfield Ludlowe HS-Taft Field [Directions] | L 2-1 | 3:15 PM, Return 6:30 PM | FCIAC Tournament-Semifinals |
| Mon., 10/30 | V Field Hockey | Ridgefield | Home - Brien McMahon HS-Casagrande Field [Directions] | Cancelled | 5:00 PM, Return 8:15 PM | FCIAC Tournament-Semifinals |
| Mon., 10/30 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:00 p.m. | 3:15 PM, Return 6:15 PM | FCIAC Tournament-Quarterfinals |
| Mon., 10/30 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | 3:15 PM | |
| Tue., 10/31 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 3:15 p.m. | ||
| Tue., 10/31 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 2:30 p.m. | ||
| Wed., 11/1 | V Field Hockey | Ridgefield | Home - Brien McMahon HS-Casagrande Field [Directions] | W 3-2 | 5:00 PM | |
| Wed., 11/1 | V Girls Soccer | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | W 2-0 | 5:00 PM, Return 8:30 PM | |
| Wed., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:30 p.m. | 3:00 PM | |
| Thu., 11/2 | FR Football | Darien | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/2 | V Boys Water Polo | Greenwich Country Day | Away - Greenwich YMCA-YMCA Pool | 3:00 p.m. | 1:30 PM, Dismiss 1:15 PM | |
| Fri., 11/3 | V Football | Trumbull | Home - Staples HS-Staples Stadium [Directions] | W 35-18 | ||
| Fri., 11/3 | V Boys Water Polo | Greenwich Country Day | Home - Staples HS-Staples High School Pool [Directions] | 3:15 p.m. | ||
| Fri., 11/3 | V Field Hockey | Darien | Away - Wilton HS-Fuijitani Field -Turf [Directions] | L 0-3 | 12:00 PM | FCIAC Tournament-Finals |
| Fri., 11/3 | V Girls Soccer | St. Joseph | Away - New Canaan HS-Dunning Stadium [Directions] | L 4-3 | 12:00 PM | FCIAC Tournament-Finals |
| Sat., 11/4 | JV Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | 9:00 AM | |
| Sat., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 3:30 p.m. | 12:30 PM, Return 5:00 PM | |
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | 10:30 AM | |
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | 11:00 AM, Dismiss 10:30 AM | |
| Tue., 11/7 | V Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | L 2-1 | CIAC Tournament-First Round | |
| Tue., 11/7 | V Girls Volleyball | Newington | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | CIAC Tournament-First Round | |
| Wed., 11/8 | V Boys Water Polo | Boys Varsity Water Polo vs CT Water Polo Premier | Home - Staples HS-Staples High School Pool [Directions] | 6:00 p.m. | ||
| Wed., 11/8 | V Field Hockey | Hamden | Home - Staples HS-Ginny Parker Field [Directions] | W 10-0 | CIAC Tournament-First Round | |
| Wed., 11/8 | V Girls Soccer | Hall | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | CIAC Tournament-Second Round | |
| Thu., 11/9 | FR Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 3:30 p.m. | 1:45 PM, Dismiss 1:15 PM | |
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/9 | V Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 6:00 p.m. | 3:00 PM, Dismiss 2:45 PM | CIAC Tournament-Second Round |
| Fri., 11/10 | V Football | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | W 49-3 | ||
| Fri., 11/10 | V Field Hockey | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | W 2-1 | CIAC Tournament-Quarterfinals | |
| Fri., 11/10 | V Girls Soccer | Greenwich | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | CIAC Tournament-Quarterfinals | |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | 1:45 PM | |
| Mon., 11/13 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 3:00 p.m. | 1:00 PM, Dismiss 12:45 PM | |
| Tue., 11/14 | V Field Hockey | Glastonbury | Home - Amity Regional HS-Field Hockey Field [Directions] | W 2-0 | 2:15 PM | CIAC Tournament-Semifinals |
| Tue., 11/14 | V Girls Soccer | St. Joseph | Away - Fairfield Warde HS-Stadium [Directions] | 6:30 p.m. | 4:45 PM, Return 8:00 PM | CIAC Tournament-Semifinals |
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/18 | V Field Hockey | Darien | Away - Wethersfield HS-Cottone Field [Directions] | W 3-1 | CIAC Tournament-Finals | |
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | 10:30 AM | |
| Mon., 11/20 | JV Football | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | ||
| Thu., 11/23 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 24-13 | 6:45 AM | |
| Thu., 11/23 | V Sideline Cheerleading | Thanksgiving game at Greenwich | Away - Greenwich HS | 10:00 a.m. | 8:45 AM | |
| Mon., 11/27 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Tue., 11/28 | V Football | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | W 13-12 | CIAC Tournament-Quarterfinals | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Tue., 11/28 | V Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Tue., 11/28 | Miscellaneous Events | Girls Ice Hockey @ Dorothy Hamill Ice Rink | Home - DO NOT USE Staples High -Dorthy Hamill Ice Rink [Directions] | 4:00 p.m. | 3:00 PM | |
| Wed., 11/29 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Thu., 11/30 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 12/1 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Sat., 12/2 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | ||
| Sat., 12/2 | V Co-ed Squash | Boys and Girls Varsity Squash vs Capitol Squash | Away - DO NOT USE Staples High -Trinity College | 10:00 a.m. | 8:30 AM | |
| Sat., 12/2 | V Girls Ice Hockey | Rinks of Shelton Jambo | Away - Not Listed-Rinks At Shelton | 4:30 p.m. | 2:05 PM (2:05 at WHS - 2:30 at SHS -> pick up Staples at Exit 18.) | |
| Sun., 12/3 | V Football | Southington | Home - Staples HS-Staples Stadium [Directions] | W 41-0 | CIAC Tournament-Semifinals | |
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Mon., 12/4 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Tue., 12/5 | V Boys Basketball | Foran (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/5 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Tue., 12/5 | V Girls Basketball | Weston (Scrim.) | Away - Weston HS-Gym (New) [Directions] | 5:15 p.m. | 3:45 PM, Return 6:30 PM | |
| Tue., 12/5 | JV Girls Squash | Girls JV Squash vs City Squash | Away - DO NOT USE Staples High -City Squash | 6:00 p.m. | ||
| Tue., 12/5 | Miscellaneous Events | Staples Athletics College Recruiting Seminar | Home - Staples HS [Directions] | 7:00 p.m. | ||
| Wed., 12/6 | V Boys Ice Hockey | Guilford (Scrim.) | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 5:15 p.m. | 2:45 PM, Dismiss 2:30 PM | |
| Wed., 12/6 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 7-0 | 7:50 Start | |
| Thu., 12/7 | V Boys Basketball | Notre Dame-Fairfield (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/7 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 12/8 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 12/8 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 3-0 | 1:45 PM (1:40 at SHS- 1:55 at WHS Staples on separate bus from Staples HS) | |
| Fri., 12/8 | Miscellaneous Events | Girls Hockey - Ridgefield Winter Garden | Home - Winter Garden Ice Arena [Directions] | 2:55 p.m. | 1:45 PM | |
| Sat., 12/9 | V Football | West Haven | Home - CCSU-Football Field [Directions] | W 21-20 | CIAC Tournament-Finals | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Wrestling | Bunnell, Shelton (Scrim.) | Home - Staples HS-Field House [Directions] | 8:00 a.m. | ||
| Sat., 12/9 | V Girls Indoor Track | Hillhouse Developmental Meet | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:00 AM | |
| Sat., 12/9 | Miscellaneous Events | Boys Ice Hockey - Jamboree at the Rinks in Shelton | Home - Sports Center of Connecticut-Lower [Directions] | 4:15 p.m. | 2:00 PM, Return 6:30 PM | |
| Mon., 12/11 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Mon., 12/11 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms Ice Rink-Ice Rink [Directions] | W 5-0 | 12:30 PM (Coach Bus to pick up at SHS - 12:30 -> exit 18 Staples) | |
| Mon., 12/11 | V Girls Squash | Girls Varsity Squash vs Darien Squash | Away - DO NOT USE Staples High -MS Squash SONO | 7:30 p.m. | ||
| Tue., 12/12 | V Boys Basketball | Holy Cross (Scrim.) | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 5:00 p.m. | 3:00 PM | |
| Tue., 12/12 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Tue., 12/12 | V Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | W 70 - 29 | 3:45 PM, Return 8:15 PM (JV/V going together) | |
| Tue., 12/12 | JV Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 5:30 p.m. | 3:45 PM, Return 8:15 PM (JV/V going together) | |
| Tue., 12/12 | FR Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM | |
| Tue., 12/12 | Miscellaneous Events | DO NOT ADD ON ANYMORE AWAY GAMES DUE TO BUS AVAILABILTY | Home - TBA [Directions] | TBA | ||
| Wed., 12/13 | V Boys Basketball | Notre Dame-West Haven (Scrim.) | Away - Notre Dame HS-Gym [Directions] | Cancelled | 2:45 PM | |
| Wed., 12/13 | V Boys Ice Hockey | Masuk | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 5-4(OT) | ||
| Wed., 12/13 | V Wrestling | Norwalk | Home - Staples HS-Field House [Directions] | 7:00 p.m. | ||
| Wed., 12/13 | V Girls Basketball | Sheehan | Home - Staples HS-Staples Gym [Directions] | L 56 - 42 | ||
| Wed., 12/13 | JV Girls Basketball | Sheehan | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/13 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-0 | ||
| Thu., 12/14 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 12/15 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 12/15 | V Boys Swimming and Diving | Trumbull | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 12/15 | V Girls Basketball | Bethel | Home - Staples HS-Staples Gym [Directions] | W 47 - 37 | ||
| Fri., 12/15 | JV Girls Basketball | Bethel | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Bridgeport Central, Fairfield Ludlowe, St. Joseph | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Greenwich, Stamford, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 12/16 | V Wrestling | Lancer Invitational | Away - Waterford HS-Francis X. Sweeney Field House | 10:00 a.m. | 6:30 AM | |
| Sat., 12/16 | V Girls Indoor Track | Bridgeport Central, Fairfield Ludlowe, St. Joseph | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Girls Indoor Track | Jambar Coaches HOF Invitational | Away - New Balance Track and Field Center | 8:30 a.m. | 6:00 AM | |
| Sat., 12/16 | V Girls Indoor Track | Greenwich, Stamford, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Mon., 12/18 | V Boys Basketball | Newtown | Home - Staples HS-Staples Gym [Directions] | W 73-57 | ||
| Mon., 12/18 | JV Boys Basketball | Newtown | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/18 | FR Boys Basketball | Newtown | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/18 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Mon., 12/18 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 3-0 | 5:40 PM (1 bus pick up at SHS (SHS/WHS) Staples transportation from Staples) | |
| Mon., 12/18 | Miscellaneous Events | Girls Ice Hockey @ Darien Ice Rink | Home - DO NOT USE Staples High -Darien Ice Rink [Directions] | 6:30 p.m. | 5:30 PM | |
| Tue., 12/19 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Tue., 12/19 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | 3:00 PM, Return 6:15 PM | |
| Wed., 12/20 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | W 3-1 | 5:30 PM | |
| Wed., 12/20 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-1 | ||
| Thu., 12/21 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Thu., 12/21 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | 4:30 PM, Return 8:00 PM | |
| Fri., 12/22 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | L 2-3 | 1:45 PM, Dismiss 1:30 PM, Return 6:00 PM | |
| Fri., 12/22 | V Girls Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | L 31-57 | ||
| Fri., 12/22 | JV Girls Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/22 | FR Girls Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/23 | V Wrestling | Trumbull, Brookfield/Shepaug, Conard, Ridgefield, Westhill | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | 7:15 AM, Return 3:00 PM | |
| Sat., 12/23 | JV Wrestling | Norwalk, Fairfield Warde, St. Joseph | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 9:30 a.m. | ||
| Sat., 12/23 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-1 | ||
| Wed., 12/27 | V Boys Basketball | West Haven | Home - Immaculate HS-Immaculate Gym [Directions] | W 62-51 | ||
| Wed., 12/27 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Away - Enfield Twin Rinks-Rink 2 [Directions] | L 3-5 | 1:00 PM | |
| Wed., 12/27 | V Wrestling | Simsbury, Bloomfield Weaver, Coventry (RI), East Hartford, Essex (VT), Jonathan Law, Middletown, Minnechaug (MA), Somers, Westfield (MA) | Away - Simsbury HS-Gym 2 | 9:30 p.m. | 6:00 AM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Wed., 12/27 | V Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | L 51-69 | 12:00 PM | |
| Wed., 12/27 | JV Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | Postponed | ||
| Wed., 12/27 | Miscellaneous Events | Girls Ice Hockey @ Dorothy Hamill Rink | Home - DO NOT USE Staples High -Dorthy Hamill Ice Rink [Directions] | 4:00 p.m. | 3:15 PM | |
| Fri., 12/29 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | W 64-52 | ||
| Fri., 12/29 | V Wrestling | Bristol Central, Conard, Wethersfield | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 8:30 a.m. | 6:30 AM | |
| Fri., 12/29 | JV Wrestling | Trumbull, Brien McMahon, Darien, Fairfield Warde, Greenwich, Masuk, TBA, New Canaan, New Fairfield, New Milford, Newtown, Ridgefield, Simsbury, Stamford, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Fri., 12/29 | V Girls Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | L 34-65 | ||
| Fri., 12/29 | JV Girls Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | Cancelled | 11:15 AM (JV/V varsity) | |
| Sat., 12/30 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 0-3 | 12:00 PM, Return 4:00 PM | |
| Tue., 1/2 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Wed., 1/3 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | L 3-6 | 6:10 PM | |
| Wed., 1/3 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 4:45 PM | |
| Wed., 1/3 | V Wrestling | Wilton | Home - Staples HS-Field House [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | W 63-20 | ||
| Wed., 1/3 | JV Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | FR Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 5-2 | ||
| Thu., 1/4 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Thu., 1/4 | V Girls Gymnastics | Greenwich, Norwalk | Away - Greenwich YWCA [Directions] | 136.2 | 4:15 PM | |
| Fri., 1/5 | V Boys Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | L 48-46 | ||
| Fri., 1/5 | JV Boys Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 3-4(OT) | TBA | |
| Fri., 1/5 | V Boys Swimming and Diving | New Canaan | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 37-38 | 4:00 PM | |
| Fri., 1/5 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 1/5 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Fri., 1/5 | V Girls Indoor Track | The Hispanic Games | Away - New Balance Track and Field Center | 5:00 p.m. | 1:00 PM | |
| Fri., 1/5 | Miscellaneous Events | DO NOT ADD ON ANYMORE AWAY GAMES DUE TO MAX BUSES OUT | Home - TBA [Directions] | TBA | ||
| Sat., 1/6 | V Boys Indoor Track | Bridgeport Central, St. Joseph, Trumbull | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Boys Indoor Track | Brien McMahon, Greenwich, Stamford, Westhill | Home - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 1/6 | V Wrestling | Bristol Central Invitational | Away - Bristol Central HS-Charles C. Marsh Gymnasium | 9:00 a.m. | 5:45 AM (JV/V going together) | |
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 1/6 | JV Wrestling | Bristol Eastern, Avon, Berlin, Branford, Bristol Central, East Hartford, Enfield, Farmington, Guilford, Ledyard, Middletown, New Fairfield, New Milford, Plainville, Pomperaug Coop, Ridgefield, Terryville-Thomaston, Wethersfield, Hall | Away - Bristol Eastern HS-Gym | 9:00 a.m. | 5:45 AM (JV/ V going together) | |
| Sat., 1/6 | V Girls Indoor Track | Bridgeport Central, St. Joseph, Trumbull | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Girls Indoor Track | Brien McMahon, Greenwich, Stamford, Westhill | Home - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 1/6 | Miscellaneous Events | BOYS INDOOR TRACK ELM CITY COACHES INVITATIONAL | Home - Hillhouse HS [Directions] | 9:00 a.m. | 7:00 AM, Return 12:00 PM | |
| Sun., 1/7 | V Co-ed Squash | Boys and Girls Varsity Squash vs Squash Haven | Away - DO NOT USE Staples High -Yale University- Brady Squash Center | Postponed | 10:30 AM | |
| Mon., 1/8 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Mon., 1/8 | JV Girls Squash | Briarcliff (NY) | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Mon., 1/8 | Miscellaneous Events | Boys JV Squash at BNX | Home - TBA [Directions] | 7:00 p.m. | ||
| Tue., 1/9 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | W 53-45 | 4:15 PM, Return 8:15 PM (JV/V going together) | |
| Tue., 1/9 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 3:45 p.m. | 4:15 PM, Return 8:15 PM (JV/V going together) | |
| Tue., 1/9 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | Postponed | 3:00 PM, Return 5:15 PM | |
| Tue., 1/9 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Tue., 1/9 | V Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | L 55-50 | ||
| Tue., 1/9 | JV Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/9 | FR Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | Postponed | ||
| Wed., 1/10 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Staples HS-Staples High School Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/10 | V Wrestling | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | 5:15 PM, Return 8:45 PM | |
| Wed., 1/10 | V Girls Gymnastics | Foran, New Canaan | Home - Staples HS-Westport YMCA [Directions] | 134.05 | ||
| Wed., 1/10 | V Girls Ice Hockey | Hamden Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 2-1 | ||
| Thu., 1/11 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:45-5 p.m. | 2:45 PM, Dismiss 2:45 AM | |
| Thu., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 3-1 | 6:00 PM (6:00 at Stamford HS-> pick up Staples at Exit 18.) | |
| Thu., 1/11 | V Girls Squash | Girls Varsity Squash vs Bronxville | Away - DO NOT USE Staples High -Lifetime Fitness , Westchester | 8:00 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | W 67-52 | ||
| Fri., 1/12 | JV Boys Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 1/12 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 52-29 | 3:00 PM, Return 6:45 PM (jv/v going together) | |
| Fri., 1/12 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 3:00 PM, Return 6:40 PM (jv/ v going together) | |
| Fri., 1/12 | V Girls Indoor Track | YaleTrack Meet | Away - Yale University-Coxe Cage | 4:00 p.m. | 2:30 PM, Dismiss 2:10 PM (girls and boys going together on the return) | |
| Fri., 1/12 | Miscellaneous Events | Boys indoor track - Yale track meet | Home - Yale University-Coxe Cage [Directions] | 1:30 p.m. | 11:45 AM | |
| Fri., 1/12 | Miscellaneous Events | DO NOT ADD ON ANYMORE AWAY GAMES DUE TO MAX BUSES OUT | Home - TBA [Directions] | TBA | ||
| Sat., 1/13 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 3-4 | ||
| Sat., 1/13 | V Boys Indoor Track | Bridgeport Central, Danbury, Darien, Greenwich, St. Joseph, Stamford, Westhill | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | V Wrestling | Fairfield Prep, Guilford, Foran, Maloney, Northwestern, Simsbury, Stratford, Westhill | Home - Staples HS-Staples Gym [Directions] | 8:45 a.m. | ||
| Sat., 1/13 | V Girls Gymnastics | Trumbull, Norwalk | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 130.75 | 2:45 PM | |
| Sat., 1/13 | V Girls Gymnastics | St. Joseph, Norwalk | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 4:30 p.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Bridgeport Central, Danbury, Darien, Greenwich, St. Joseph, Stamford, Westhill | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Mon., 1/15 | V Boys Basketball | St. Bernard | Home - Staples HS-Staples Gym [Directions] | L 70-59 | ||
| Mon., 1/15 | JV Boys Basketball | St. Bernard | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Mon., 1/15 | FR Boys Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 2:45 p.m. | ||
| Mon., 1/15 | FR Boys Basketball | St. Bernard | Home - Staples HS-Staples Gym [Directions] | Postponed | ||
| Mon., 1/15 | V Boys Ice Hockey | Milford Coop | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 5-2 | ||
| Wed., 1/17 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | W 7-3 | 6:45 PM, Return 10:40 PM | |
| Wed., 1/17 | V Wrestling | Fairfield Ludlowe | Home - Staples HS-Field House [Directions] | 6:00 p.m. | ||
| Wed., 1/17 | FR Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | Postponed | 2:30 PM | |
| Wed., 1/17 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Wed., 1/17 | Miscellaneous Events | CO ED SKING RACE 1 | Home - Mt. Southingon Ski Area [Directions] | 3:30 p.m. | 2:00 PM (BOYS AND GIRLS GOING TOGETHER) | |
| Thu., 1/18 | V Boys Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | L 78-71 OT | ||
| Thu., 1/18 | JV Boys Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/18 | FR Boys Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/18 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Thu., 1/18 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 61-46 | 3:30 PM, Return 7:30 PM (JV/V going together) | |
| Thu., 1/18 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | 3:30 PM, Return 7:30 PM (JV/V going together) | |
| Thu., 1/18 | V Girls Gymnastics | Darien | Home - Staples HS-Westport YMCA [Directions] | 135.1 | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 p.m. | ||||||
| Thu., 1/18 | Miscellaneous Events | Boys V Squash at New Canaan | Home - TBA [Directions] | 8:00 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | L 60-57 | 4:00 PM, Return 8:15 PM (JV/V going together) | |
| Fri., 1/19 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | 4:00 PM, Return 8:15 PM (JV/V going together) | |
| Fri., 1/19 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 5:15 PM | |
| Fri., 1/19 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 1/19 | V Girls Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | L 42-49 | ||
| Fri., 1/19 | JV Girls Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | New Milford | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 1-5 | ||
| Sat., 1/20 | V Boys Indoor Track | Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/20 | V Wrestling | SNITKIN DUALS | Away - Norwich Free Academy-Alumni Gym | 10:00 a.m. | 7:00 AM | |
| Sat., 1/20 | V Competitive Cheerleading | NIGHTHAWK CHEER CLASSIC | Away - Not Listed-North Haven HS | 4:00 p.m. | 2:00 PM | |
| Sat., 1/20 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-1 | 7:50 Start time | |
| Sat., 1/20 | V Girls Indoor Track | Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/20 | V Girls Squash | Girls Varsity Squash vs GFA | Away - Greens Farms Academy | 4:00 p.m. | ||
| Sat., 1/20 | Miscellaneous Events | Boys indoor track - SCC COACHES INVITATIONAL - HILLHOUSE | Home - Hillhouse HS [Directions] | 9:00 a.m. | 7:00 AM | |
| Sat., 1/20 | Miscellaneous Events | Boys V Squash at GFA | Home - TBA [Directions] | 4:00 p.m. | ||
| Sun., 1/21 | JV Girls Squash | Girls JV Squash vs Darien Squash | Away - DO NOT USE Staples High -MS Squash SONO | 4:30 p.m. | ||
| Mon., 1/22 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Mon., 1/22 | JV Girls Squash | Girls JV Squash Vs Rye ( black) | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Mon., 1/22 | Miscellaneous Events | CO ED SKING RACE # 2 | Home - Mt. Southingon Ski Area [Directions] | 3:30 p.m. | 2:00 PM (EARLY DISMISSAL 1:50PM) | |
| Tue., 1/23 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 61-45 | 4:00 PM, Return 8:15 PM (JV/V going together) | |
| Tue., 1/23 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | 4:00 PM, Return 8:15 PM (JV/V going together) | |
| Tue., 1/23 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM, Return 5:15 PM | |
| Tue., 1/23 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Tue., 1/23 | V Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | W 64-46 | ||
| Tue., 1/23 | JV Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Girls Squash | Girls Varsity Squash vs New Canaan | Away - Chelsea Piers - -Gym | 7:00 p.m. | ||
| Tue., 1/23 | Miscellaneous Events | Boys JV Squash at Darien | Home - TBA [Directions] | 8:00 p.m. | ||
| Tue., 1/23 | Miscellaneous Events | DO NOT ADD ANYMORE AWAY GAMES DUE TO # OF BUSES OUT | Home - TBA [Directions] | TBA | ||
| Wed., 1/24 | V Boys Ice Hockey | SCW Knights | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 4-3(OT) | ||
| Wed., 1/24 | V Wrestling | Darien | Away - Darien HS-DHS South Gym [Directions] | 5:00 p.m. | 3:15 PM, Return 6:30 PM | |
| Wed., 1/24 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 2-0 | ||
| Wed., 1/24 | Miscellaneous Events | CO ED SKING RACE #3 | Home - Mt. Southingon Ski Area [Directions] | 3:30 p.m. | 2:00 PM (BOYS AND GIRLS GOING TOGETHER -EARLY DISMISSAL 1:50PM) | |
| Wed., 1/24 | Miscellaneous Events | Boys Varsity Squash at Rye | Home - TBA [Directions] | 7:00 p.m. | ||
| Thu., 1/25 | V Girls Gymnastics | Stamford, Westhill | Home - Staples HS-Westport YMCA [Directions] | 135.7 | ||
| Fri., 1/26 | V Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | W 57-49 | ||
| Fri., 1/26 | JV Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 1/26 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 48-31 | 4:15 PM (JV/V are going together) | |
| Fri., 1/26 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | 4:15 PM, Return 8:15 PM (JV/V are going together) | |
| Fri., 1/26 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 3:00 PM, Return 5:15 PM | |
| Fri., 1/26 | Miscellaneous Events | County Ball Ludlowe, Warde and Barlow Juniors | Home - TBA [Directions] | TBA | ||
| Sat., 1/27 | V Boys Indoor Track | FCIAC West Divisionals | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/27 | V Wrestling | TFC Kevin Miller Tourney | Away - East Hartford HS | 9:30 a.m. | 6:30 AM | |
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, New Milford, St. Joseph, Stamford, Trumbull, Westhill, Weston, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Sat., 1/27 | V Competitive Cheerleading | LUDLOWE CHEER OPEN | Away - Fairfield Ludlowe HS-Gym 1 | 11:00 a.m. | 9:45 AM | |
| Sat., 1/27 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 7-2 | ||
| Sat., 1/27 | V Girls Indoor Track | FCIAC West Divisionals | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/27 | Miscellaneous Events | GIRLS ICE HOCKEY - STAMFORD HIGH SCHOOL - 3:15 BUS PICK UP AT SHS | Home - TBA [Directions] | TBA | TBA | |
| Sat., 1/27 | Miscellaneous Events | County Ball SHS, Weston and Wilton | Home - TBA [Directions] | TBA | ||
| Mon., 1/29 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 4-3 | 1:45 PM | |
| Mon., 1/29 | Miscellaneous Events | COED SKI - makeup race | Home - Mt. Southingon Ski Area [Directions] | 3:15 p.m. | 2:00 PM (BOYS AND GIRLS GOING TOGETHER) | |
| Mon., 1/29 | Miscellaneous Events | Leadership Council Meeting | Home - Staples HS [Directions] | 7:00 p.m. | ||
| Tue., 1/30 | V Boys Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | W 76-68 | ||
| Tue., 1/30 | JV Boys Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Tue., 1/30 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 5:00 p.m. | 3:15 PM | |
| Tue., 1/30 | JV Wrestling | Fairfield Warde, Fairfield Ludlowe | Away - Fairfield Warde HS-Small Gym [Directions] | 5:00 p.m. | 3:00 PM, Return 7:00 PM | |
| Tue., 1/30 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 40-31 | 3:45 PM (jv/v going together) | |
| Tue., 1/30 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | 3:45 PM (jv/v going together) | |
| Tue., 1/30 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | W 3-1 | 3:00 PM (3:00 at Stamford HS-> pick up Staples at Exit 18.) | |
| Tue., 1/30 | Miscellaneous Events | Boys JV Squash at home vs New Canaan | Home - TBA [Directions] | 8:15 p.m. | ||
| Tue., 1/30 | Miscellaneous Events | DO NOT ADD ANYMORE AWAY GAMES DUE TO # OF BUSES OUT | Home - TBA [Directions] | TBA | ||
| Wed., 1/31 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Wed., 1/31 | V Wrestling | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:00 p.m. | 1:30 PM, Dismiss 1:10 PM, Return 4:30 PM | |
| Wed., 1/31 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 7-3 | 2:15 PM (2:15 from Stamford HS Staples transportation from Staples HS) | |
| Wed., 1/31 | Miscellaneous Events | Girls Ice Hockey @ Ridgefield Garden | Home - Winter Garden Ice Arena [Directions] | 3:30 p.m. | 2:30 PM | |
| Wed., 1/31 | Miscellaneous Events | COED SKI RACE #4 | Home - Mt. Southingon Ski Area [Directions] | 3:30 p.m. | 2:00 PM (BOYS AND GIRLS GOING TOGETHER - EARLY DISMISSAL 1:50PM) | |
| Wed., 1/31 | Miscellaneous Events | Boys Varsity Squash at Greenwich | Home - TBA [Directions] | 7:30 p.m. | ||
| Thu., 2/1 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | W 67-40 | 4:30 PM, Return 8:15 PM (JV/V going together) | |
| Thu., 2/1 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | 4:30 PM, Return 8:15 PM (JV/V going together) | |
| Thu., 2/1 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | 3:15 PM, Return 5:15 PM | |
| Thu., 2/1 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Thu., 2/1 | V Girls Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | W 61-39 | ||
| Thu., 2/1 | JV Girls Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/1 | FR Girls Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/1 | V Girls Gymnastics | Fairfield Warde, Norwalk, Wilton | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 138.80 | ||
| Thu., 2/1 | V Girls Squash | Girls Varsity Squash vs Rye | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Thu., 2/1 | Miscellaneous Events | FCIAC Boys and Girls Indoor Track Championships | Home - Floyd Little Athletic Center-Field House [Directions] | 4:00 p.m. | 2:30 PM, Return 5:45 PM | |
| Thu., 2/1 | Miscellaneous Events | DO NOT ADD ANYMORE AWAY GAMES DUE TO # OF BUSES OUT | Home - TBA [Directions] | TBA | ||
| Fri., 2/2 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Fri., 2/2 | V Boys Swimming and Diving | Darien | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | Miscellaneous Events | Boys Varsity Squash vs Fairfield A | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Fri., 2/2 | Miscellaneous Events | Red and White Ball for SHS, WESTON and WIlton Seniors | Home - TBA [Directions] | TBA | ||
| Sat., 2/3 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 1-6 | ||
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-0 | ||
| Sat., 2/3 | Miscellaneous Events | FCIAC Boys and Girls Indoor Track JV/Last Chance Qualifier | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/3 | Miscellaneous Events | Boys Varsity Squash vs Scars | Home - Chelsea Piers - -Gym [Directions] | 7:00 p.m. | ||
| Sat., 2/3 | Miscellaneous Events | RED and WHITE BALL FOR LUDLOWE/WARDE AND BARLOW SENIORS | Home - TBA [Directions] | TBA | ||
| Mon., 2/5 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Mon., 2/5 | JV Girls Squash | Girls JV Squash vs Rye ( Red) | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Mon., 2/5 | Miscellaneous Events | CO-ED VARSITY SKI TEAM - QUALIFIERS | Home - Mt. Southingon Ski Area [Directions] | 3:15 p.m. | 2:00 PM | |
| Tue., 2/6 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 57-43 | 4:15 PM, Return 8:15 PM (JV/V going together) | |
| Tue., 2/6 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | 4:15 PM, Return 8:00 PM (JV/V going together) | |
| Tue., 2/6 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | 3:00 PM, Dismiss TBA, Return 5:15 PM (JV/V going together) | |
| Tue., 2/6 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Tue., 2/6 | V Wrestling | Fairfield Warde | Home - Staples HS-Field House [Directions] | 6:30 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | L 46-39 | ||
| Tue., 2/6 | JV Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Girls Gymnastics | Wilton, Norwalk | Away - Wilton HS-Aux Gym [Directions] | 135.15 | 3:15 PM | |
| Tue., 2/6 | Miscellaneous Events | St. Joe's University vs Boston University - in the stadium | Home - Staples HS [Directions] | 4:30 p.m. | ||
| Tue., 2/6 | Miscellaneous Events | Boys JV Squash Vs Briar Boys | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Tue., 2/6 | Miscellaneous Events | DO NOT ADD ANYMORE AWAY GAMES DUE TO # OF BUSES OUT | Home - TBA [Directions] | TBA | ||
| Wed., 2/7 | V Boys Ice Hockey | Newington Coop | Away - Newington-Blue Rink [Directions] | L 0-3 | 1:15 PM, Dismiss 1:00 PM | |
| Wed., 2/7 | V Boys Swimming and Diving | Westhill/Stamford | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 3-1 | 5:00 PM (Pick up at Stamford HS) | |
| Wed., 2/7 | Miscellaneous Events | National Signing Day Ceremony | Home - Staples HS [Directions] | 3:00 p.m. | ||
| Wed., 2/7 | Miscellaneous Events | CO-ED SKI TEAM - RACE #5 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 2:00 PM | |
| Wed., 2/7 | Miscellaneous Events | Girls Ice Hockey at Darien Ice Rink | Home - DO NOT USE Staples High -Darien Ice Rink [Directions] | 5:30 p.m. | 4:45 PM | |
| Wed., 2/7 | Miscellaneous Events | Boys Varsity Squash vs CS Boys Inter at Intensity | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Thu., 2/8 | V Boys Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | V Girls Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | Miscellaneous Events | BOYS AND GIRLS INDOOR TRACK - CLASS LL CIAC CHAMPIONSHIPS | Home - Hillhouse HS [Directions] | 4:00 p.m. | 2:00 PM | |
| Thu., 2/8 | Miscellaneous Events | Varsity Girls Squash at home vs Greenwich | Home - Intensity Fitness [Directions] | 8:15 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 51-44 | 4:30 PM, Return 8:15 PM (JV/V going together) | |
| Fri., 2/9 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | 4:30 PM, Return 8:15 PM (JV/V going together) | |
| Fri., 2/9 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 3:00 PM, Return 5:15 PM | |
| Fri., 2/9 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:40 PM | |
| Fri., 2/9 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | 2:15 PM, Dismiss 2:00 PM | |
| Fri., 2/9 | V Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | W 44-42 | ||
| Fri., 2/9 | JV Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | FR Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | Miscellaneous Events | DO NOT ADD ANYMORE AWAY GAMES DUE TO # OF BUSES OUT | Home - TBA [Directions] | TBA | ||
| Sat., 2/10 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 0-4 | ||
| Sat., 2/10 | V Competitive Cheerleading | HATTER FEST CHEER COMPETITION | Away - Danbury HS-Main Gym | 10:00 a.m. | 8:00 AM | |
| Sat., 2/10 | V Girls Gymnastics | FCIAC Championship | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 132.25 | ||
| Sat., 2/10 | V Girls Ice Hockey | Southington Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 6-2 | 6:10 start Vs. Avon | |
| Sat., 2/10 | Miscellaneous Events | BOYS VARSITY WRESTLING - FCIAC'S | Home - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | 8:15 AM | |
| Sun., 2/11 | Miscellaneous Events | Girls and Boys Varsity Squash at Squash Haven | Home - TBA [Directions] | 1:00 p.m. | ||
| Mon., 2/12 | V Boys Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | L 55-39 | ||
| Mon., 2/12 | JV Boys Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Mon., 2/12 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | W 50-44 | 3:30 PM, Return 7:15 PM (JV/v going together) | |
| Mon., 2/12 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | 3:30 PM, Return 7:15 PM (JV/v going together) | |
| Mon., 2/12 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Cancelled | 2:45 PM, Dismiss 2:30 PM, Return 5:15 PM | |
| Mon., 2/12 | JV Girls Squash | Girls JV Squash vs Rye ( Gray) | Home - Intensity Fitness [Directions] | 8:15 a.m. | ||
| Mon., 2/12 | Miscellaneous Events | CO-ED SKI TEAM - PRACTICE NIGHT | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 2:00 PM | |
| Wed., 2/14 | V Boys Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | W 58-49 | ||
| Wed., 2/14 | JV Boys Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 3-2(OT) | 6:15 PM | |
| Wed., 2/14 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | 4:00 PM, Return 8:15 PM (JV/v going together) | |
| Wed., 2/14 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | 4:00 PM, Return 8:15 PM (JV/v going together) | |
| Wed., 2/14 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:00 PM, Return 5:15 PM | |
| Wed., 2/14 | V Girls Gymnastics | Norwalk | Home - Westport YMCA [Directions] | 134.55 | ||
| Wed., 2/14 | Miscellaneous Events | Boys Varsity Squash vs City SQ at Msquash Port Chester | Home - TBA [Directions] | 8:00 p.m. | ||
| Thu., 2/15 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Fri., 2/16 | V Boys Basketball | Bassick | Home - Staples HS-Staples Gym [Directions] | W 84-42 | ||
| Fri., 2/16 | JV Boys Basketball | Bassick | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/16 | FR Boys Basketball | Bassick | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/16 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | Miscellaneous Events | BOYS AND GIRLS INDOOR TRACK CIAC OPEN | Home - Hillhouse HS [Directions] | 12:00 p.m. | 9:45 AM | |
| Sat., 2/17 | Miscellaneous Events | FCIAC Girls Basketball Quarterfinals | Home - Staples HS-Staples Gym [Directions] | TBA | ||
| Mon., 2/19 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 71-69 | 4:15 PM, Return 8:10 PM (JV/V going together) | |
| Mon., 2/19 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | 4:15 PM, Return 8:15 PM (JV/V going together) | |
| Mon., 2/19 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 3:00 PM, Return 5:15 PM | |
| Mon., 2/19 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 0-4 | TBA | |
| Wed., 2/21 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 65-41 | 4:00 PM, Return 8:15 PM (JV/V going together) | |
| Wed., 2/21 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | 4:00 PM, Return 8:15 PM (JV/V going together) | |
| Wed., 2/21 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM | |
| Wed., 2/21 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | L 3-5 | 3:15 PM | |
| Wed., 2/21 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 2-1 | 6:20 PM | |
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Fri., 2/23 | Miscellaneous Events | Boys and Girls Squash - HS Nationals Specter Center, Philadelphia 2/23/24-2/25/24 | Home - TBA [Directions] | TBA | ||
| Sat., 2/24 | V Boys Basketball | Wilton | Home - Fairfield Warde HS-Gym [Directions] | 4:00 p.m. | 2:00 PM | |
| Sat., 2/24 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | T 3-3(OT) | 2:10 PM | |
| Sat., 2/24 | V Competitive Cheerleading | SPIRIT SPECTACULAR | Away - Oxford HS-Main Gym | TBA | 7:30 AM | |
| Sat., 2/24 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Jonathan Law | 1:00 p.m. | 11:30 AM | |
| Tue., 2/27 | V Boys Basketball | Ridgefield | Away - Wilton HS-Wilton Field House [Directions] | 7:15 p.m. | ||
| Tue., 2/27 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Tue., 2/27 | Miscellaneous Events | CO-ED SKI TEAM - QUALIFIERS | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 2:00 PM | |
| Tue., 2/27 | Miscellaneous Events | Sailing Regotta #! | Home - TBA [Directions] | TBA | TBA | |
| Wed., 2/28 | V Girls Basketball | Mercy | Away - Mercy HS-Gym [Directions] | L 35-61 | 4:00 PM | |
| Thu., 2/29 | V Boys Basketball | Trumbull | Away - Wilton HS-Wilton Field House [Directions] | 7:00 p.m. | 5:00 PM, Return 7:45 PM | |
| Thu., 2/29 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | TBA | |
| Thu., 2/29 | V Co-ed Alpine Skiing | State Championships | Home - Mt. Southingon Ski Area [Directions] | TBA | 12:45 PM, Dismiss 12:30 PM | |
| Thu., 2/29 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Fri., 3/1 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:50 PM | |
| Sat., 3/2 | V Girls Ice Hockey | Darien | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 2-1 | 3:15 PM (Bus will pick up at Stamford HS 3:15 -> To Exit 18 to pick up Staples) | |
| Sat., 3/2 | Miscellaneous Events | CHEER COMP - STATES | Home - trumbull high school [Directions] | 3:00 p.m. | 1:45 PM | |
| Sat., 3/2 | Miscellaneous Events | 36 th annual New England Interscholastic Indoor track and field championships - Boys and girls indoor track | Home - Reggie Lewis Center [Directions] | 4:00 p.m. | 11:30 AM | |
| Mon., 3/4 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Bethel HS-Danbury Ice Arena- Patriot Rink [Directions] | L 2-3 | ||
| Mon., 3/4 | V Boys Ice Hockey | CIAC Div III First Round | Away - Higher Seed | TBA | ||
| Tue., 3/5 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | 2:50 PM | |
| Wed., 3/6 | V Girls Ice Hockey | New Canaan | Away - Quinnipiac University-TD Bank Sports Center [Directions] | 7:00 p.m. | 3:30 PM (Bus Departs SHS 3:30 -> Stops at Exits 18 for Staples -> Quinnipiac) | |
| Thu., 3/7 | V Boys Basketball | East Catholic | Away - East Catholic HS-Gym [Directions] | L 53-67 | ||
| Thu., 3/7 | V Boys Ice Hockey | CIAC Div III Quarterfinal | Away - Site TBA | TBA | ||
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 3/7 | Miscellaneous Events | Unified Basketball Tournament | Home - Fairfield Ludlowe HS-Gym 1 [Directions] | 4:00 p.m. | 3:00 PM | |
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Sun., 3/10 | V Boys Rugby | (D1)- VARSITY BOYS RUGBY VS Pelham High School | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | ||
| Sun., 3/10 | JV Boys Rugby | (D2) JV BOYS RUGBY VS PELHAM HIGH SCHOOL | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Mon., 3/11 | V Boys Ice Hockey | CIAC Div III Semifinal | Away - Site TBA | TBA | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Ice Hockey | CIAC Div III Final | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Sat., 3/16 | Miscellaneous Events | WIN TOURNAMENT SHS- NO FIELDS INDOORS/OUTDOORS AVAILABLE FOR PRACTICE OR GAMES | Home - TBA [Directions] | TBA | ||
| Wed., 3/20 | V Baseball | Jonathan Law (Scrim.) | Away - Jonathan Law HS-Baseball Field [Directions] | 3:45 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 3/20 | V Boys Lacrosse | Deerfield Academy (MA) (Scrim.) | Away - Farmington Sports Arena | 3:15 p.m. | ||
| Wed., 3/20 | V Boys Lacrosse | Deerfield Academy (MA) (Scrim.) | Away - Farmington Sports Arena | TBA | 1:00 PM | |
| Thu., 3/21 | FM Boys Rugby | Trumbull (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 5:15 p.m. | ||
| Fri., 3/22 | V Baseball | Fairfield Prep (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Fri., 3/22 | V Girls Tennis | Weston (Scrim.) | Away - Weston HS-WHS Tennis Courts [Directions] | 3:30 p.m. | 3:00 PM, Return 5:30 PM | |
| Sat., 3/23 | V Boys Lacrosse | Jamboree on stadium field, center and upper ovals. | Away - Darien HS-[CIAC] Willow Brook Park | 8:00 a.m. | 7:30 AM, Return 1:00 PM | |
| Sat., 3/23 | JV Boys Lacrosse | Darien, Salisbury School (Scrim.) | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 8:00 a.m. | 7:30 AM, Return 12:30 PM | |
| Sat., 3/23 | FR Boys Lacrosse | Don Bosco (NJ) (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sat., 3/23 | V Girls Lacrosse | GIRLS LAX PLAY DAY | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 3/23 | Miscellaneous Events | BOYS VOLLEYBALL - DARIEN PLAY DAY | Home - TBA [Directions] | 8:30 a.m. | 7:00 AM | |
| Mon., 3/25 | V Baseball | Trumbull (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Softball | Notre Dame-Fairfield (Scrim.) | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Tue., 3/26 | V Baseball | Weston (Scrim.) | Away - Weston HS-Revson #1 (Varsity) [Directions] | 3:45 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM | |
| Tue., 3/26 | V Girls Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:00 p.m. | 3:30 PM, Return 6:15 PM | |
| Wed., 3/27 | V Baseball | Masuk (Scrim.) | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 1:50 PM | |
| Wed., 3/27 | V Boys Lacrosse | Fairfield Ludlowe (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 3/27 | JV Boys Lacrosse | Stamford (Scrim.) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | V Co-ed Sailing | Daniel Hand, Guilford, Xavier | Away - Pettipaug Yacht Club [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM | |
| Wed., 3/27 | V Girls Lacrosse | Greens Farms Academy (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Softball | Naugatuck (Scrim.) | Away - Naugatuck HS-Softball Diamond [Directions] | 3:30 p.m. | 1:45 PM, Dismiss 1:30 PM | |
| Thu., 3/28 | V Boys Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 7:30 PM (jv/v going together) | |
| Thu., 3/28 | JV Boys Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | 2:30 PM, Dismiss 2:15 PM (JV/V going together) | |
| Thu., 3/28 | FM Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 7:00 PM | |
| Thu., 3/28 | V Softball | Joel Barlow (Scrim.) | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Fri., 3/29 | Miscellaneous Events | Good Friday | Home - Staples HS [Directions] | TBA | ||
| Sat., 3/30 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 1:00 p.m. | 11:15 AM | |
| Sat., 3/30 | JV Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Sat., 3/30 | FR Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 3/30 | JV Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 12:00 p.m. | 9:15 AM | |
| Sat., 3/30 | V Softball | Sacred Heart Academy | Home - Staples HS-Wakeman Field [Directions] | 12:00 p.m. | ||
| Sat., 3/30 | JV Softball | Sacred Heart Academy | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Sat., 3/30 | JV Softball | Trumbull | Home - Staples HS-Wakeman Field [Directions] | 1:30 p.m. | ||
| Sat., 3/30 | V Girls Tennis | Branford | Away - Branford HS-Tennis Courts [Directions] | 11:00 a.m. | 9:30 AM | |
| Sat., 3/30 | V Girls Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | 1:00 p.m. | ||
| Sat., 3/30 | JV Girls Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | 2:15 p.m. | ||
| Mon., 4/1 | V Boys Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | JV Boys Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/1 | V Girls Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | 2:00 PM, Dismiss 1:45 PM, Return 5:45 PM | |
| Tue., 4/2 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | 3:00 PM, Return 5:45 PM | |
| Wed., 4/3 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | 3:00 PM, Return 7:00 PM (jv/v going together) | |
| Wed., 4/3 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | 3:00 PM, Return 7:00 PM (jv/v going together) | |
| Thu., 4/4 | V Boys Lacrosse | Stepinac (NY) | Home - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | ||
| Thu., 4/4 | JV Boys Lacrosse | Stepinac (NY) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Thu., 4/4 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM (jv / v going together) | |
| Thu., 4/4 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/v going together) | |
| Thu., 4/4 | V Co-ed Sailing | Regatta # 2 | Away - Grass Island | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM | |
| Thu., 4/4 | FR Girls Lacrosse | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Girls Rugby | Fairfield Ludlowe, North Haven | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Baseball | Greenwich | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Fri., 4/5 | JV Baseball | Greenwich | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Fri., 4/5 | FR Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM | |
| Fri., 4/5 | V Boys Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | 2:10 PM, Dismiss 2:00 PM, Return 7:30 PM (jv/v going together) | |
| Fri., 4/5 | V Boys Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM, Return 5:30 PM | |
| Sat., 4/6 | V Baseball | Amity | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 4/6 | JV Baseball | Amity | Home - Staples HS-Wakeman Field [Directions] | 1:00 p.m. | ||
| Sat., 4/6 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 10:30 a.m. | 8:45 AM | |
| Sat., 4/6 | V Boys Lacrosse | Rye (NY) | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Sat., 4/6 | JV Boys Lacrosse | Rye (NY) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 12:30 p.m. | ||
| Sat., 4/6 | FR Boys Lacrosse | Chaminade (NY) (Scrim.) | Away - Chaminade-OTT FIELD | 1:00 p.m. | 10:30 AM | |
| Sat., 4/6 | V Boys Outdoor Track | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Masuk | Home - Staples HS-Ginny Parker Field [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | JV Girls Lacrosse | Masuk | Home - Staples HS-Ginny Parker Field [Directions] | 1:30 p.m. | ||
| Sat., 4/6 | V Girls Outdoor Track | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | ||
| Mon., 4/8 | V Boys Lacrosse | Fairfield Warde | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/8 | JV Boys Lacrosse | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 5:00 p.m. | 3:15 PM, Return 5:15 PM | |
| Mon., 4/8 | V Boys Tennis | Ridgefield | Home - Staples HS-Staples Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Mon., 4/8 | JV Boys Tennis | Ridgefield | Home - Staples HS-Town Farms Tennis Courts [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Boys Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 6:00 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/v going together) | |
| Mon., 4/8 | JV Boys Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 5:00 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/v going together) | |
| Mon., 4/8 | FR Girls Lacrosse | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Softball | Stamford | Home - Staples HS-Wakeman Field [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 5:00 p.m. | 3:15 PM (v/jv going together) | |
| Mon., 4/8 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 5:00 p.m. | 3:15 PM (v/jv going together) | |
| Tue., 4/9 | V Boys Outdoor Track | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM, Return 5:30 PM | |
| Tue., 4/9 | JV Boys Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Tue., 4/9 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM | |
| Tue., 4/9 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM | |
| Tue., 4/9 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | 3:45 PM, Return 6:30 PM | |
| Tue., 4/9 | V Girls Outdoor Track | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Tennis | New Canaan | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | JV Girls Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Water Polo | vs Greenwich Aquatics | Home - Staples HS-Staples High School Pool [Directions] | 5:00 p.m. | ||
| Wed., 4/10 | V Baseball | Norwalk | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | JV Baseball | Norwalk | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | 3:00 PM, Return 5:45 PM | |
| Wed., 4/10 | V Boys Rugby | Fairfield Ludlowe | Home - Staples HS-Staples Stadium [Directions] | 5:45 p.m. | ||
| Wed., 4/10 | FM Boys Rugby | Fairfield Ludlowe | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/10 | V Softball | Norwalk | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM | |
| Wed., 4/10 | Miscellaneous Events | D1 BOYS V RUGBY VS FAIRFIELD RUGBY CLUB | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/11 | JV Boys Lacrosse | St. Joseph | Home - Staples HS-Wakeman Field B (turf) [Directions] | Postponed | ||
| Thu., 4/11 | JV Boys Rugby | vs Aspetuck Rugby Club | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/11 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | Postponed | 2:30 PM | |
| Thu., 4/11 | V Girls Lacrosse | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | JV Girls Lacrosse | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Thu., 4/11 | V Girls Rugby | North Haven | Away - North Haven Athletic Complex-All-Purpose Field [Directions] | 5:00 p.m. | 3:00 PM | |
| Fri., 4/12 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 4/12 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/v going together) | |
| Sat., 4/13 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 3:00 p.m. | 1:15 PM | |
| Sat., 4/13 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | 3:15 PM | |
| Sat., 4/13 | FR Boys Lacrosse | Chaminade (NY) (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/13 | V Girls Lacrosse | East Lyme | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | ||
| Sat., 4/13 | JV Girls Lacrosse | East Lyme | Home - Staples HS-Ginny Parker Field [Directions] | 3:00 p.m. | ||
| Sat., 4/13 | V Girls Outdoor Track | Hillhouse Freshman Sophmore Novice meet -GIRLS OUTDOOR TRACK - | Away - Hillhouse HS | 10:00 a.m. | 7:00 AM | |
| Mon., 4/15 | V Baseball | New Canaan | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | JV Baseball | New Canaan | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | 3:00 PM, Return 5:30 PM | |
| Mon., 4/15 | JV Boys Lacrosse | Chaminade (NY) | Away - Jackson Avenue School-Gym | 2:15 p.m. | 11:45 AM | |
| Mon., 4/15 | V Boys Tennis | Norwalk | Home - Staples HS-Staples Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Mon., 4/15 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | 2:30 PM (JV/V GOING TOGETHER ( VACATION WEEK)) | |
| Mon., 4/15 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | 2:30 PM (JV/V GOING TOGETHER ( VACATION WEEK)) | |
| Mon., 4/15 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/15 | V Girls Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM, Return 5:30 PM | |
| Tue., 4/16 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 2:00 p.m. | 11:30 AM (jv/v going together) | |
| Tue., 4/16 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 2:00 p.m. | 11:15 AM (jv/v going together) | |
| Tue., 4/16 | FR Baseball | Ridgefield | Home - Staples HS-Baseball Diamond [Directions] | 2:00 p.m. | ||
| Tue., 4/16 | V Boys Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 5:30 p.m. | 2:15 PM | |
| Tue., 4/16 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM | |
| Tue., 4/16 | V Softball | Ridgefield | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | Postponed | 2:30 PM | |
| Tue., 4/16 | V Girls Tennis | Stamford | Home - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 4/17 | JV Baseball | Brien McMahon | Away - Roton MS [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 4/17 | FR Baseball | Brien McMahon | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/17 | FR Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | V Boys Tennis | Brien McMahon | Home - Staples HS-Staples Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Wed., 4/17 | V Boys Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | JV Boys Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/17 | JV Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-Turf field | 3:30 p.m. | 1:45 PM | |
| Wed., 4/17 | V Softball | Brien McMahon | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 10:00 a.m. | 3:00 PM, Return 5:30 PM | |
| Thu., 4/18 | V Boys Lacrosse | Wilton | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/18 | JV Boys Lacrosse | Wilton | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | JV Girls Lacrosse | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Thu., 4/18 | JV Softball | Brien McMahon | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Fri., 4/19 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM (jv/ v going together) | |
| Fri., 4/19 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM (jv/ v) | |
| Fri., 4/19 | FR Baseball | Norwalk | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 4/19 | FR Boys Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 12:30 p.m. | 9:15 AM (JV/V GOING TOGETHER ( VACATION WEEK)) | |
| Fri., 4/19 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 11:00 a.m. | 9:15 AM (JV/V GOING TOGETHER ( VACATION WEEK)) | |
| Fri., 4/19 | V Softball | Norwalk | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | Miscellaneous Events | BOYS OUTDOOR TRACK - CT. DISTANCE FESTIVAL @ HALL HIGH SCHOOL | Home - TBA [Directions] | 4:00 p.m. | 2:30 PM | |
| Sat., 4/20 | V Boys Lacrosse | Bishop Guertin (NH) | Away - Stellos Stadium-Bishop Guertin HS | 1:30 p.m. | 8:00 AM | |
| Sat., 4/20 | V Girls Lacrosse | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 11:00 a.m. | 9:00 AM | |
| Sat., 4/20 | JV Softball | Norwalk | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Sat., 4/20 | Miscellaneous Events | BOYS OUTDOOR TRACK - HILLHOUSE INVITATIONAL | Home - Hillhouse HS-Bowen Field [Directions] | 10:00 a.m. | 7:45 AM | |
| Mon., 4/22 | V Baseball | Stamford | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | JV Baseball | Stamford | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | FR Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 4/22 | V Boys Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Mon., 4/22 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 5:00 PM | |
| Mon., 4/22 | V Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | 1:55 PM, Dismiss 1:45 PM | |
| Mon., 4/22 | JV Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | Cancelled | 12:00 PM | |
| Mon., 4/22 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 3:30 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 5:45 PM (jv/ v goin together) | |
| Mon., 4/22 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | Postponed | 2:15 PM, Return 5:45 PM (jv/v going together) | |
| Tue., 4/23 | V Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | 4:15 PM, Return 7:15 PM | |
| Tue., 4/23 | JV Boys Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:00 PM | |
| Tue., 4/23 | V Boys Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Wilton | Home - Staples HS-Staples Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Tue., 4/23 | JV Boys Tennis | Wilton | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Volleyball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | JV Boys Volleyball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | Postponed | ||
| Tue., 4/23 | V Girls Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | JV Girls Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:00 PM | |
| Tue., 4/23 | V Girls Lacrosse | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM, Return 5:30 PM (jv/v going together) | |
| Tue., 4/23 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM, Return 5:30 PM (jv/v going together) | |
| Tue., 4/23 | V Girls Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:00 p.m. | 3:00 PM, Return 6:15 PM | |
| Wed., 4/24 | V Baseball | Darien | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | JV Baseball | Darien | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | 3:00 PM, Return 5:30 PM | |
| Wed., 4/24 | FR Boys Lacrosse | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | V Boys Rugby | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Wed., 4/24 | JV Boys Rugby | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | 5:15 p.m. | ||
| Wed., 4/24 | FM Boys Rugby | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Lacrosse | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 4:30 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 7:15 PM (JV/V GOING TOGETHER) | |
| Wed., 4/24 | JV Girls Lacrosse | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 6:15 p.m. | 2:35 PM, Dismiss 2:30 PM, Return 7:15 PM (jv/ GOING TOGETHER) | |
| Wed., 4/24 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 5:00 PM | |
| Wed., 4/24 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 5:30 PM (JV/V GOING TOGETHER) | |
| Thu., 4/25 | V Boys Lacrosse | Don Bosco (NJ) | Away - Don Bosco Prep School-Stadium Turf | 6:00 p.m. | 3:00 PM | |
| Thu., 4/25 | JV Boys Lacrosse | Don Bosco (NJ) | Away - Don Bosco Prep School-Stadium Turf | 4:15 p.m. | 1:30 PM, Dismiss 1:15 PM | |
| Thu., 4/25 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 7-0 [Detailed Results] | 3:15 PM | |
| Thu., 4/25 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | 3:15 PM, Return 5:30 PM | |
| Thu., 4/25 | V Girls Golf | Darien | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | JV Girls Golf | Darien | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | V Girls Rugby | Darien, Simsbury | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/25 | V Girls Tennis | Bridgeport Central | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | Miscellaneous Events | Penn Relays - Franklin Field, University of Pennslyvania - Girls Varsity Outdoor track | Home - TBA [Directions] | TBA | ||
| Fri., 4/26 | V Baseball | Greenwich | Away - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/v going) | |
| Fri., 4/26 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Fri., 4/26 | FR Baseball | Greenwich | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | 3:45 PM, Return 6:30 PM | |
| Fri., 4/26 | FR Girls Lacrosse | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Softball | Greenwich | Home - Greens Farms Elementary School-Softball Field [Directions] | 7:00 p.m. | ||
| Fri., 4/26 | JV Softball | Greenwich | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Sat., 4/27 | V Baseball | Morgan | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 4/27 | JV Baseball | Morgan | Home - Staples HS-Wakeman Field [Directions] | 1:00 p.m. | ||
| Sat., 4/27 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | 9:00 AM | |
| Sat., 4/27 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 11:00 a.m. | 9:00 AM | |
| Sat., 4/27 | V Boys Outdoor Track | O' Grady Relay | Away - Danbury HS-Stadium Track | 9:00 a.m. | 7:00 AM | |
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 12:30 p.m. | ||
| Sat., 4/27 | JV Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Girls Lacrosse | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/27 | JV Girls Lacrosse | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/27 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 1:00 p.m. | 10:45 AM | |
| Sat., 4/27 | Miscellaneous Events | 41st O'Grady's Day 2 - Girls Varsity Outdoor Track | Home - Danbury HS [Directions] | 9:00 a.m. | 7:00 AM (girls and boys track going together) | |
| Mon., 4/29 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/v going together) | |
| Mon., 4/29 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | 2:30 PM, Dismiss 2:15 PM (jv/ v) | |
| Mon., 4/29 | FR Baseball | Wilton | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | 3:00 PM, Return 5:30 PM | |
| Mon., 4/29 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Mon., 4/29 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Mon., 4/29 | V Softball | Wilton | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | JV Softball | Wilton | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Mon., 4/29 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | JV Girls Tennis | Fairfield Warde | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:15 PM, Return 6:00 PM | |
| Tue., 4/30 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | W 5-2 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM, Return 5:00 PM (jv/v going together) | |
| Tue., 4/30 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 5:00 PM (JV/V going together) | |
| Tue., 4/30 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Tue., 4/30 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Tue., 4/30 | V Girls Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/30 | JV Girls Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/30 | FR Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-2nd Field | 3:30 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 4:30 PM | |
| Tue., 4/30 | V Girls Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:15 PM | |
| Tue., 4/30 | V Girls Tennis | Fairfield Ludlowe | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Girls Tennis | Fairfield Ludlowe | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | Bridgeport Central | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | JV Boys Rugby | Southington | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:30 PM, Return 6:00 PM | |
| Wed., 5/1 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM | |
| Wed., 5/1 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM | |
| Wed., 5/1 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Wed., 5/1 | JV Softball | Bridgeport Central | Away - Bridgeport Central HS-Softball Diamond 2 [Directions] | Postponed | 2:30 PM, Dismiss 2:15 PM (JV/V GOING TOGETHER) | |
| Wed., 5/1 | V Girls Tennis | Darien | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | New Canaan | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Trumbull | Home - Staples HS-Staples Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Thu., 5/2 | JV Boys Tennis | Trumbull | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | JV Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/2 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | 2:10 PM, Dismiss 1:55 PM, Return 5:45 PM | |
| Thu., 5/2 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 5:15 PM | |
| Thu., 5/2 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | 3:30 PM, Return 6:30 PM | |
| Thu., 5/2 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM (jv/v going together) | |
| Thu., 5/2 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM (jv/v going together) | |
| Fri., 5/3 | V Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | Postponed | 3:00 PM, Return 5:30 PM | |
| Fri., 5/3 | FR Boys Lacrosse | Ridgefield | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | JV Boys Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Fri., 5/3 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 4:00 PM | |
| Fri., 5/3 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM (JV/V GOING TOGETHER) | |
| Fri., 5/3 | V Girls Water Polo | Hopkins School | Away - Hopkins School-Hopkins | 4:15 p.m. | 1:45 PM | |
| Fri., 5/3 | Miscellaneous Events | BOYS OUTDOOR TRACK - FRESHMEN AND SOPHMORES- MIDDLETOWN INVITATIONAL | Home - Middletown HS-Track [Directions] | 3:30 p.m. | 1:00 PM | |
| Sat., 5/4 | JV Baseball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | V Boys Lacrosse | St. Johns Prep (MA) | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Sat., 5/4 | JV Boys Lacrosse | West Haven | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 5/4 | FR Boys Lacrosse | St. Anthonys (NY) | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Sat., 5/4 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | W 6-1 [Detailed Results] | 3:00 PM, Return 6:00 PM | |
| Sat., 5/4 | V Boys Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 11:00 a.m. | ||
| Sat., 5/4 | JV Boys Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 12:30 p.m. | ||
| Sat., 5/4 | V Girls Lacrosse | Joel Barlow | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Sat., 5/4 | JV Girls Lacrosse | Joel Barlow | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Org-Jake Spartan Invitational- Amity Regional High School | Away - Amity Regional HS-Amity HS Track | 9:00 a.m. | 7:00 AM | |
| Sat., 5/4 | JV Softball | Fairfield Ludlowe | Away - Fairfield Warde HS-Softball Diamond [Directions] | 10:00 a.m. | 2:30 PM, Dismiss 2:15 PM (JV/V GOING TOGETHER) | |
| Sat., 5/4 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 12:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM (JV/V GOING TOGETHER) | |
| Sat., 5/4 | Miscellaneous Events | BOYS OUTDOOR TRACK - VARSITY - MIDDLETOWN INVITATIONAL | Home - Middletown HS-Middletown HS [Directions] | 12:00 p.m. | 9:30 AM | |
| Sun., 5/5 | Miscellaneous Events | V & JV Boys Rugby at Georgetown Prep | Home - Georgetown Preparatory School [Directions] | 12:00 p.m. | ||
| Sun., 5/5 | Miscellaneous Events | Boys Rugby D1 and D2 Georgetown Prep (MD) | Home - TBA [Directions] | 12:00 p.m. | ||
| Mon., 5/6 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | 3:00 PM, Return 5:30 PM | |
| Mon., 5/6 | FR Boys Lacrosse | Wilton | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 6:30 PM | |
| Mon., 5/6 | V Boys Tennis | Danbury | Home - Staples HS-Staples Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 5/6 | JV Boys Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Mon., 5/6 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM, Return 5:00 PM | |
| Mon., 5/6 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 6:30 PM | |
| Mon., 5/6 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:15 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 5:30 PM (JV/V GOING TOGETHER) | |
| Mon., 5/6 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 5/6 | JV Girls Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Baseball | Fairfield Ludlowe | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | JV Baseball | Fairfield Ludlowe | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | Westhill | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | Westhill | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 3:00 PM | |
| Tue., 5/7 | V Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | 3:45 PM, Return 6:30 PM | |
| Tue., 5/7 | JV Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 5:15 PM | |
| Tue., 5/7 | V Girls Tennis | St. Joseph | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Girls Tennis | St. Joseph | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | Miscellaneous Events | Signing Day | Home - Staples HS [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 6:00 p.m. | 3:30 PM, Return 7:30 PM | |
| Wed., 5/8 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM | |
| Wed., 5/8 | FR Baseball | Trumbull | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/8 | V Boys Lacrosse | Glastonbury | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Wed., 5/8 | JV Boys Lacrosse | Glastonbury | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | FR Boys Lacrosse | Stamford | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Wed., 5/8 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Wed., 5/8 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | 2:00 PM, Dismiss 1:45 PM, Return 5:00 PM | |
| Wed., 5/8 | FR Girls Lacrosse | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Trumbull | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | JV Softball | Trumbull | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Thu., 5/9 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:00 PM | |
| Thu., 5/9 | FM Boys Rugby | Stamford Rugby Club | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM | |
| Thu., 5/9 | JV Boys Tennis | Wilton | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | 2:25 PM, Dismiss 2:15 PM, Return 5:00 PM | |
| Thu., 5/9 | V Girls Lacrosse | Cheshire | Away - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | 3:30 PM | |
| Thu., 5/9 | JV Girls Lacrosse | Cheshire | Away - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 5/9 | V Girls Outdoor Track | THE LOUCKS GAMES DAY 1 - GIRLS VARSITY OUTDOOR TRACK - WHITE PLAINS HIGH SCHOOL | Away - White Plains HS | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Thu., 5/9 | V Girls Tennis | Westhill | Home - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | JV Girls Tennis | Wilton | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | FR Girls Lacrosse | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Girls Outdoor Track | THE LOUCKS GAMES DAY 2 - GIRLS VARSITY OUTDOOR TRACK - WHITE PLAINS HIGH SCHOOL | Away - White Plains HS | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM | |
| Fri., 5/10 | Miscellaneous Events | BOYS JV RUGBY VS CITY OF BPT RUGBY ACADEMY (COBRA) | Home - TBA [Directions] | 5:30 p.m. | 3:15 PM, Return 6:00 PM | |
| Sat., 5/11 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:15 PM | |
| Sat., 5/11 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 2:00 p.m. | 12:00 PM | |
| Sat., 5/11 | V Boys Tennis | Avon | Home - Staples HS-Staples Tennis Courts [Directions] | 11:30 a.m. | ||
| Sat., 5/11 | V Girls Lacrosse | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 1:30 p.m. | ||
| Sat., 5/11 | JV Girls Lacrosse | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | THE LOUCKS GAMES DAY 3 - GIRLS VARSITY OUTDOOR TRACK - WHITE PLAINS HIGH SCHOOL | Away - White Plains HS | 9:00 a.m. | 6:00 AM | |
| Sat., 5/11 | V Girls Rugby | Fairfield Ludlowe, Ridgefield | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 9:30 a.m. | 8:15 AM | |
| Sat., 5/11 | V Softball | Danbury | Home - Staples HS-Wakeman Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | JV Softball | Danbury | Home - Staples HS-Wakeman Field [Directions] | 1:45 p.m. | ||
| Sat., 5/11 | Miscellaneous Events | BOYS OUTDOOR TRACK - CT. FROSHMORE INVITATIONAL - WILLOW BROOK PARK IN NEW BRITAIN | Home - TBA [Directions] | 10:00 a.m. | 7:00 AM | |
| Sat., 5/11 | Miscellaneous Events | BOYS OUTDOOR TRACK - GREATER HARTFORD INVITATIONAL - DAY 2 | Home - East Hartford HS-Track [Directions] | 9:00 a.m. | 6:30 AM | |
| Mon., 5/13 | V Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Baseball | St. Joseph | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | 2:25 PM, Dismiss 2:15 PM, Return 5:25 PM | |
| Mon., 5/13 | FR Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | 3:45 p.m. | 2:00 PM | |
| Mon., 5/13 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 6:00 PM | |
| Mon., 5/13 | V Boys Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:30 PM | |
| Mon., 5/13 | FR Girls Lacrosse | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 5:30 PM | |
| Mon., 5/13 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:15 PM | FCIAC Tournament-Quarterfinals |
| Mon., 5/13 | JV Girls Tennis | Darien | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | 8:15 AM | |
| Tue., 5/14 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 4:00 p.m. | 8:30 AM (jv/v goinhg together) | |
| Tue., 5/14 | FR Baseball | Danbury | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | Brunswick School | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | Brunswick School | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | FM Boys Rugby | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 5:30 p.m. | ||
| Tue., 5/14 | V Boys Tennis | Wilton | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | FCIAC Tournament-Quarterfinals | |
| Tue., 5/14 | V Girls Golf | New Canaan | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | JV Girls Golf | New Canaan | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | V Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | 3:45 PM, Return 6:45 PM | |
| Tue., 5/14 | JV Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:00 PM | |
| Tue., 5/14 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM, Return 5:30 PM | |
| Tue., 5/14 | JV Softball | St. Joseph | Away - St. Joseph HS-Long Hill, Admin Field [Directions] | Cancelled | 2:15 PM, Return 5:30 PM | |
| Tue., 5/14 | JV Girls Tennis | Ridgefield | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 5:00 PM | |
| Wed., 5/15 | JV Boys Rugby | Darien | Away - MMS Upper Field-MMS Upper [Directions] | 4:30 p.m. | 3:00 PM, Return 5:45 PM (Darien Varsity ( D1) vs SHS JV (D2)) | |
| Wed., 5/15 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Wed., 5/15 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:10 PM, Return 6:30 PM (JV/V GOING TOGETHER) | |
| Wed., 5/15 | FR Girls Lacrosse | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Baseball | Westhill | Away - Allen's Meadow [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | 3:00 PM, Return 5:30 PM | |
| Thu., 5/16 | V Boys Outdoor Track | Bridgeport Central | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:30 p.m. | 3:00 PM | FCIAC Tournament-Semifinals |
| Thu., 5/16 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 2:15 PM, Dismiss 2:00 PM, Return 5:30 PM (jv/v going together) | |
| Thu., 5/16 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 2:15 PM, Return 5:30 PM (JV and V going together) | |
| Thu., 5/16 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | 3:15 PM, Return 6:15 PM | FCIAC Tournament-Quarterfinals |
| Thu., 5/16 | FR Girls Lacrosse | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Outdoor Track | Bridgeport Central | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Rugby | Simsbury, Ridgefield | Away - Holden Field-Turf [Directions] | 6:00 p.m. | 3:00 PM | |
| Fri., 5/17 | V Baseball | Greenwich | Away - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | 12:00 PM | FCIAC Tournament-Quarterfinals |
| Fri., 5/17 | V Boys Rugby | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 5/17 | JV Boys Rugby | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Fri., 5/17 | V Softball | Hamden | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Sat., 5/18 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 12:00 p.m. | 10:00 AM | FCIAC Tournament-Quarterfinals |
| Sat., 5/18 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 12:00 p.m. | FCIAC Tournament-Quarterfinals | |
| Sat., 5/18 | JV Boys Volleyball | Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, Ridgefield, Shelton | Away - Fairfield Ludlowe HS-Main Gym | 8:45 a.m. | ||
| Sat., 5/18 | Miscellaneous Events | Junior Prom | Home - Staples HS [Directions] | 7:00 p.m. | ||
| Mon., 5/20 | V Baseball | Trumbull | Away - Scalzi Park-Cubeta Stadium [Directions] | 7:00 p.m. | 12:00 PM | FCIAC Tournament-Semifinals |
| Mon., 5/20 | FM Boys Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Mon., 5/20 | JV Boys Tennis | Greenwich | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Girls Golf | Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 5/20 | JV Girls Golf | Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/21 | JV Baseball | Westhill | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Tue., 5/21 | FR Baseball | Westhill | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Tue., 5/21 | V Boys Lacrosse | New Canaan | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | 2:45 PM, Dismiss 2:15 PM, Return 5:30 PM | FCIAC Tournament-Semifinals |
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Tue., 5/21 | V Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 6:00 p.m. | 3:00 PM | |
| Tue., 5/21 | V Girls Golf | Ridgefield | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/21 | JV Girls Golf | Ridgefield | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/21 | V Girls Lacrosse | St. Joseph (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 2:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Wed., 5/22 | FR Baseball | Fairfield Prep | Home - Staples HS-Wakeman Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Softball | Westhill (Scrim.) | Home - Staples HS-Wakeman Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/23 | V Boys Lacrosse | Darien | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | 5:00 PM, Return 8:00 PM | FCIAC Tournament-Finals |
| Thu., 5/23 | V Softball | Bethel (Scrim.) | Home - Staples HS-Wakeman Softball Field [Directions] | Cancelled | ||
| Fri., 5/24 | V Boys Tennis | Hamden | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | CIAC Tournament-First Round | |
| Fri., 5/24 | V Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | CIAC Tournament-First Round | |
| Fri., 5/24 | V Girls Tennis | New Britain | Home - Staples HS-Staples Tennis Courts [Directions] | 12:00 p.m. | CIAC Tournament-First Round | |
| Sat., 5/25 | V Girls Tennis | Cheshire | Away - Cheshire HS-Tennis Courts [Directions] | 12:00 p.m. | 12:00 PM | CIAC Tournament-Second Round |
| Mon., 5/27 | Miscellaneous Events | Memorial Day | Home - Staples HS [Directions] | TBA | ||
| Tue., 5/28 | V Baseball | Hamden | Away - Hamden HS-HHS Baseball Field [Directions] | 3:30 p.m. | 1:15 PM, Dismiss 1:00 PM | CIAC Tournament-First Round |
| Tue., 5/28 | V Boys Tennis | Trumbull | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | CIAC Tournament-Quarterfinals | |
| Tue., 5/28 | V Girls Golf | Trumbull | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | JV Girls Golf | Trumbull | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | V Girls Lacrosse | Glastonbury | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | CIAC Tournament-First Round | |
| Tue., 5/28 | V Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | 3:00 p.m. | 1:00 PM, Dismiss 12:45 PM, Return 5:00 PM | CIAC Tournament-First Round |
| Tue., 5/28 | V Girls Tennis | Maloney | Away - Maloney HS-Tennis Courts [Directions] | 3:00 p.m. | 12:30 PM, Dismiss 12:00 PM | |
| Wed., 5/29 | V Baseball | New Milford | Home - Staples HS-Baseball Diamond [Directions] | 3:30 p.m. | CIAC Tournament-Second Round | |
| Wed., 5/29 | V Boys Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | CIAC Tournament-First Round | |
| Wed., 5/29 | V Boys Outdoor Track | CIAC Class LL Outdoor Track Championships | Away - Willowbrook Park | 4:00 p.m. | 1:00 PM | |
| Wed., 5/29 | V Boys Tennis | Fairfield Prep | Away - Fairfield University-Walsh Athletic Center - Tennis Courts [Directions] | 3:45 p.m. | 12:00 PM | CIAC Tournament-Semifinals |
| Wed., 5/29 | V Girls Outdoor Track | CIAC Class LL Outdoor Track Championships | Away - Willowbrook Park | 4:00 p.m. | 1:00 PM | |
| Wed., 5/29 | V Girls Tennis | South Windsor | Away - South Windsor HS-Wapping Tennis Courts [Directions] | 3:30 p.m. | 12:00 PM | CIAC Tournament-Semifinals |
| Wed., 5/29 | Miscellaneous Events | Froshmore Boys Rugby at Fairfield Prep | Home - TBA [Directions] | 5:30 p.m. | 3:30 PM | |
| Thu., 5/30 | V Boys Tennis | Greenwich | Home - Wilton HS-Wilton HS tennis courts [Directions] | 1:00 p.m. | CIAC Tournament-Finals | |
| Thu., 5/30 | V Girls Tennis | Greenwich | Home - Wilton HS-Wilton HS tennis courts [Directions] | 3:30 p.m. | CIAC Tournament-Finals | |
| Thu., 5/30 | Miscellaneous Events | INCOMING 9TH GRADE - BOYS AND GIRLS XC MEETING AT THE STADIUM | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 5/31 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | 3:15 PM, Return 6:15 PM | CIAC Tournament-Quarterfinals |
| Sat., 6/1 | V Baseball | Newtown | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 6/1 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 12:30 p.m. | CIAC Tournament-Quarterfinals | |
| Sat., 6/1 | Miscellaneous Events | SHS SENIOR PROM | Home - Staples HS [Directions] | TBA | ||
| Mon., 6/3 | V Boys Rugby | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | State Tournament-Semifinals | |
| Tue., 6/4 | V Baseball | Fairfield Warde | Away - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 3:30 p.m. | 12:00 PM | CIAC Tournament-Semifinals |
| Sat., 6/8 | V Baseball | Amity | Away - Palmer Field-Baseball Diamond [Directions] | 12:00 p.m. | CIAC Tournament-Finals | |
| Sat., 6/8 | V Boys Rugby | Greenwich | Home - Southern CT State University-Stadium [Directions] | 3:00 p.m. | State Tournament-Finals | |
| Mon., 6/10 | Miscellaneous Events | Graduation | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||