| Staples 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 603 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Sat., 8/31 | V Football | TBA | Away - TBA | Cancelled | ||
| Tue., 9/3 | V Boys Soccer | Fairfield Prep (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | 2:30 PM, Return 5:00 PM | |
| Tue., 9/3 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 4:00 p.m. | 2:30 PM, Return 5:15 PM | |
| Thu., 9/5 | V Boys Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:30 p.m. | 3:00 PM, Return 5:30 PM | |
| Fri., 9/6 | V Boys Cross Country | Blue and White Time Trials | Home - Staples HS-Staples Stadium [Directions] | 2:45 p.m. | ||
| Fri., 9/6 | V Girls Cross Country | Blue and White Time Trials | Home - Staples HS-Staples Stadium [Directions] | 2:45 p.m. | ||
| Sat., 9/7 | V Boys Soccer | Wethersfield, Kingswood-Oxford, Tolland (Scrim.) | Away - Wethersfield HS-Cottone Field [Directions] | 9:00 a.m. | 7:30 AM, Return 2:00 PM | |
| Sat., 9/7 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart | 9:00 a.m. | 7:30 AM, Return 10:15 AM; 1 Bus | |
| Mon., 9/9 | V Field Hockey | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 4:00 p.m. | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Mon., 9/9 | V Girls Volleyball | Stratford (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | New Canaan, St. Joseph, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 5:30 PM; 2 Buses | |
| Tue., 9/10 | V Boys Soccer | Glastonbury | Away - Glastonbury HS-CFC Park, Bethany, CT [Directions] | 4:30 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Glastonbury (Scrim.) | Away - Glastonbury HS-CFC Park, Bethany, CT [Directions] | 4:30 p.m. | 2:30 PM, Return 5:30 PM; 1 Bus | |
| Tue., 9/10 | V Girls Cross Country | New Canaan, St. Joseph, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 5:30 PM; 1 Bus | |
| Tue., 9/10 | V Field Hockey | Greens Farms Academy | Away - Greens Farm Academy-Field 5 | 3:45 p.m. | 2:30 PM, Return 4:30 PM; 1 Bus | |
| Tue., 9/10 | V Girls Soccer | Weston (Scrim.) | Away - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | 5:30 PM, Return 8:00 PM; 1 Bus | |
| Wed., 9/11 | V Girls Soccer | Bethel (Scrim.) | Away - Bethel HS-Rourke Field [Directions] | 4:00 p.m. | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Thu., 9/12 | V Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | 2:15 PM, Dismiss TBA, Return 5:00 PM | |
| Fri., 9/13 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | L 13-14 | 4:00 PM, Return 9:00 PM; 2 Buses | |
| Fri., 9/13 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | W 4-1 | 2:30 PM, Return 5:00 PM | |
| Fri., 9/13 | V Sideline Cheerleading | Football vs. Stamford | Away - Not Listed | 7:00 p.m. | 5:30 PM, Return 9:00 PM; 1 Bus (Destination: Stamford HS) | |
| Fri., 9/13 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | W 3-2 | 2:30 PM (ride with varsity) | |
| Sat., 9/14 | V Boys Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | 9:00 a.m. | 6:30 AM, Return 1:00 PM | |
| Sat., 9/14 | V Boys Water Polo | Boys Varsity Water Polo vs Greenwich Aquatics | Home - Staples HS-Staples High School Pool [Directions] | 2:00 p.m. | ||
| Sat., 9/14 | V Girls Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | 9:00 a.m. | 6:30 AM, Return 1:00 PM | |
| Sat., 9/14 | V Girls Soccer | Bridgeport Central | Home - Staples HS-Loeffler Field - Staples HS [Directions] | W 5-0 | ||
| Mon., 9/16 | V Boys Cross Country | Danbury, Stamford, Trinity Catholic | Home - Tarrywile Park [Directions] | 4:00 p.m. | 1:30 PM, Dismiss 1:00 PM, Return 5:30 PM; 2 Buses | |
| Mon., 9/16 | V Boys Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | L 1-0 | 1:45 PM, Dismiss 1:40 PM, Return 4:45 PM; 1 Bus | |
| Mon., 9/16 | V Girls Cross Country | Danbury, Stamford, Trinity Catholic | Home - Tarrywile Park [Directions] | 4:00 p.m. | 1:30 PM, Dismiss 1:00 PM, Return 5:30 PM; 2 Buses | |
| Mon., 9/16 | V Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | W 2-1 | ||
| Tue., 9/17 | V Girls Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | W 7-0 | ||
| Wed., 9/18 | V Boys Soccer | Trinity Catholic | Home - Staples HS-Loeffler Field - Staples HS [Directions] | W 6-0 | ||
| Wed., 9/18 | V Field Hockey | Darien | Home - Staples HS-Ginny Parker Field [Directions] | L 3-1 | ||
| Wed., 9/18 | V Girls Swimming and Diving | Danbury | Home - Staples HS-Staples High School Pool [Directions] | Staples 102 Danbury 71 | ||
| Wed., 9/18 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 3-2 | 2:00 PM, Dismiss 1:45 PM, Return 6:00 PM; 1 Bus (JV will ride with varsity) | |
| Thu., 9/19 | V Girls Soccer | Trinity Catholic | Away - Trinity Catholic-Gaglio Field | W 8-0 | 2:30 PM, Return 5:00 PM | |
| Fri., 9/20 | V Boys Soccer | Norwalk | Home - Staples HS-Loeffler Field - Staples HS [Directions] | W 1-0 | ||
| Fri., 9/20 | V Boys Water Polo | Suffield Academy | Away - Suffield Academy-Pool | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 5:30 PM; 1 Bus | |
| Fri., 9/20 | V Girls Volleyball | Trinity Catholic | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Sat., 9/21 | V Football | New Britain | Home - Norwalk HS-Testa Field, NHS [Directions] | W 14-8 | 4:00 PM, Return 9:00 PM; 2 Buses | |
| Sat., 9/21 | V Sideline Cheerleading | Football vs New Britain | Home - Norwalk HS-Testa Field, NHS [Directions] | 7:00 p.m. | 5:30 PM, Return 9:00 PM; 1 Bus | |
| Sat., 9/21 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 9-2 | 11:00 AM; 1 Bus (Shuttle with JV) | |
| Mon., 9/23 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:40 PM, Return 5:00 PM; 1 Bus | |
| Tue., 9/24 | V Boys Cross Country | Darien, Fairfield Warde, Norwalk | Home - Fairfield Warde HS-Stadium [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 6:00 PM; 2 Buses | |
| Tue., 9/24 | V Boys Soccer | Trumbull | Away - Trumbull HS-New Turf Field [Directions] | T 2-2 | 4:00 PM, Return 6:30 PM; 1 Bus | |
| Tue., 9/24 | V Girls Cross Country | Darien, Fairfield Warde, Norwalk | Home - Fairfield Warde HS-Stadium [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 6:00 PM; 1 Bus | |
| Tue., 9/24 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 2-0 | 2:30 PM, Return 5:00 PM; 1 Bus (Shuttle with JV) | |
| Tue., 9/24 | V Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | W 3-1 | ||
| Wed., 9/25 | V Boys Water Polo | Loomis Chaffee School, Westminster | Home - Staples HS-Staples High School Pool [Directions] | 3:00 p.m. | ||
| Wed., 9/25 | V Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 6-3 | ||
| Thu., 9/26 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 1-0 | 5:00 PM, Return 8:00 PM; 1 Bus | |
| Thu., 9/26 | V Field Hockey | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | W 4-0 | ||
| Thu., 9/26 | V Girls Volleyball | Trumbull | Away - Trumbull HS-Gym [Directions] | L 0-3 | TBA (JV will ride with varsity) | |
| Fri., 9/27 | V Boys Water Polo | Horace Mann (NY) | Home - Staples HS-Staples High School Pool [Directions] | 3:00 p.m. | ||
| Fri., 9/27 | V Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 2-0 | ||
| Sat., 9/28 | V Boys Cross Country | Bowdoin Park Classic | Away - Bowdoin Park | 10:00 a.m. | 7:00 AM, Return 2:00 PM | |
| Sat., 9/28 | V Football | Ridgefield | Home - Norwalk HS-Testa Field, NHS [Directions] | L 0-7 | 3:00 PM, Return 8:00 PM; 2 Buses | |
| Sat., 9/28 | V Sideline Cheerleading | Football vs. Ridgefield | Home - Norwalk HS-Testa Field, NHS [Directions] | 6:00 p.m. | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Sat., 9/28 | V Girls Cross Country | Bowdoin Park Classic | Away - Stratton Brook State Park | 10:00 a.m. | 7:00 AM, Return 2:00 PM; 1 Bus | |
| Sat., 9/28 | V Field Hockey | Danbury | Away - Danbury HS-Broadview MS [Directions] | W 8-0 | 11:00 AM, Return 2:00 PM | |
| Sat., 9/28 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 1-3 | 2:30 PM, Return 6:00 PM; 1 Bus | |
| Tue., 10/1 | V Boys Cross Country | Fairfield Ludlowe, Ridgefield, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 5:30 PM; 2 Buses | |
| Tue., 10/1 | V Boys Soccer | Greenwich | Home - Staples HS-Loeffler Field - Staples HS [Directions] | W 1-0 | ||
| Tue., 10/1 | V Girls Cross Country | Fairfield Ludlowe, Ridgefield, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 5:30 PM; 1 Bus | |
| Tue., 10/1 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 2-0 | 2:30 PM, Return 5:30 PM | |
| Tue., 10/1 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 0-3 | TBA (JV will ride with varsity) | |
| Wed., 10/2 | V Boys Water Polo | Horace Mann (NY) | Away - Horace Mann School | 4:00 p.m. | 2:30 PM, Return 6:00 PM | |
| Wed., 10/2 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 7-0 | 2:30 PM, Return 5:30 PM | |
| Wed., 10/2 | V Girls Swimming and Diving | St. Joseph | Home - Staples HS-Staples High School Pool [Directions] | Staples 98
St Josephs 74 [Detailed Results] | ||
| Thu., 10/3 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 2-1 | 5:00 PM, Return 7:30 PM (Shuttle with JV) | |
| Thu., 10/3 | V Girls Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | L 0-3 | ||
| Fri., 10/4 | V Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 35-7 | 4:15 PM, Return 9:00 PM; 2 Buses | |
| Fri., 10/4 | V Sideline Cheerleading | Football vs Brien McMahon | Away - Not Listed | 7:00 p.m. | 5:30 PM, Return 9:00 PM; 1 Bus (Destination: Brien McMahon HS) | |
| Fri., 10/4 | V Field Hockey | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | W 6-0 | ||
| Fri., 10/4 | V Girls Soccer | Brien McMahon | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 5-0 | ||
| Fri., 10/4 | V Girls Swimming and Diving | Wilton | Home - Staples HS-Staples High School Pool [Directions] | Wilton 107 Staples 79 | ||
| Sat., 10/5 | V Boys Soccer | Fairfield Ludlowe | Home - Staples HS-Loeffler Field - Staples HS [Directions] | T 0-0 | ||
| Sat., 10/5 | V Boys Water Polo | Boys Varsity Water Polo vs CPAC | Home - Staples HS-Staples High School Pool [Directions] | 2:00 p.m. | ||
| Sat., 10/5 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 3-2 | TBA (JV will ride with varsity) | |
| Mon., 10/7 | V Boys Cross Country | Greenwich, Brien McMahon, Wilton | Away - Greenwich Point [Directions] | 4:00 p.m. | 1:45 PM, Return 5:30 PM; 2 Buses | |
| Mon., 10/7 | V Girls Cross Country | Greenwich, Brien McMahon, Wilton | Away - Greenwich Point [Directions] | 4:00 p.m. | 1:45 PM, Return 5:30 PM; 1 Bus | |
| Mon., 10/7 | V Field Hockey | Stamford | Home - Staples HS-Ginny Parker Field [Directions] | W 10-0 | ||
| Mon., 10/7 | V Girls Soccer | Fairfield Ludlowe | Away - Tomlinson MS-Turf Field [Directions] | W 1-0 | 3:00 PM, Return 5:30 PM | |
| Mon., 10/7 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | 1:30 PM, Dismiss 1:15 PM, Return 4:15 PM; 1 Bus | |
| Mon., 10/7 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | L 0-3 | ||
| Thu., 10/10 | V Field Hockey | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | W 5-0 | ||
| Thu., 10/10 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Gym [Directions] | W 3-0 | TBA (JV will ride with varsity) | |
| Fri., 10/11 | V Boys Water Polo | Cardinal Tournament | Away - Greenwich HS-Pool | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM, Return 6:00 PM; 1 Bus | |
| Sat., 10/12 | V Boys Soccer | Stamford | Home - Staples HS-Loeffler Field - Staples HS [Directions] | L 2-0 | ||
| Sat., 10/12 | V Boys Water Polo | Cardinal Tournament | Away - Greenwich HS-Pool | 10:30 a.m. | 8:00 AM, Return 4:00 PM; 1 Bus | |
| Sat., 10/12 | V Field Hockey | Longmeadow (MA) | Home - Staples HS-Ginny Parker Field [Directions] | W 5-1 | ||
| Sat., 10/12 | V Girls Volleyball | Girls Volleyball Fall Brawl | Away - RHAM HS-RHAM MS | TBA | 6:30 AM, Return 4:00 PM; 1 Bus | |
| Sat., 10/12 | Miscellaneous Events | Adult Rugby | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sun., 10/13 | Miscellaneous Events | PAL Football | Home - Staples HS-Staples Stadium [Directions] | 11:30 a.m. | ||
| Mon., 10/14 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | W 8-0 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Mon., 10/14 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Staples HS-Staples High School Pool [Directions] | Staples 98 Norwalk 82 | ||
| Tue., 10/15 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:00 p.m. | 11:30 AM, Dismiss 11:00 AM, Return 6:00 PM; 2 Buses | |
| Tue., 10/15 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | T 0-0 | 2:00 PM, Dismiss 1:45 PM, Return 5:00 PM; 1 Bus | |
| Tue., 10/15 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:00 p.m. | 11:30 AM, Return 6:00 PM; 1 Bus | |
| Tue., 10/15 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | W 10-0 | 2:30 PM, Return 6:00 PM | |
| Tue., 10/15 | V Girls Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | W 3-2 | ||
| Wed., 10/16 | V Boys Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | 5:00 p.m. | ||
| Wed., 10/16 | V Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | T 0-0 | ||
| Wed., 10/16 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | 2:05 PM, Dismiss 2:00 PM, Return 5:30 PM; 1 Bus | |
| Thu., 10/17 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | L 3-1 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Thu., 10/17 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 3-1 | TBA (JV will ride with varsity) | |
| Fri., 10/18 | V Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | L 20-53 | 4:00 PM, Return 9:00 PM; 2 Buses | |
| Fri., 10/18 | V Sideline Cheerleading | Sideline Cheerleading to North Haven | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | 5:00 PM, Return 9:00 PM; 1 Bus | |
| Fri., 10/18 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 9-0 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Fri., 10/18 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | W 3-0 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Sat., 10/19 | V Boys Soccer | St. Joseph | Home - Staples HS-Loeffler Field - Staples HS [Directions] | W 1-0 | ||
| Sat., 10/19 | V Field Hockey | Branford | Home - Staples HS-Ginny Parker Field [Directions] | W 3-0 | ||
| Sun., 10/20 | Miscellaneous Events | PAL Football | Home - Staples HS-Staples Stadium [Directions] | 11:30 a.m. | ||
| Mon., 10/21 | V Field Hockey | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | W 5-0 | ||
| Mon., 10/21 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | T 1-1 | 2:00 PM, Dismiss 1:45 PM, Return 5:00 PM; 1 Bus | |
| Mon., 10/21 | V Girls Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | W 3-2 | ||
| Tue., 10/22 | V Boys Cross Country | Wilton JV Invitational | Away - Allen's Meadow | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 6:00 PM; 1 Bus | |
| Tue., 10/22 | V Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | W 2-0 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Tue., 10/22 | V Girls Cross Country | Wilton JV Invitational | Away - Allen's Meadow | 4:00 p.m. | 2:00 PM, Dismiss 1:30 PM, Return 5:30 PM; 1 Bus | |
| Wed., 10/23 | V Girls Soccer | Westhill | Home - Staples HS-Loeffler Field - Staples HS [Directions] | W 7-0 | ||
| Wed., 10/23 | V Girls Swimming and Diving | Ridgefield | Home - Staples HS-Staples High School Pool [Directions] | Staples 93
Ridgefield 93 [Detailed Results] | ||
| Wed., 10/23 | V Girls Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | W 3-1 | ||
| Thu., 10/24 | V Boys Cross Country | Hatter Freshmen Invitational | Away - Danbury HS | 4:00 p.m. | 1:45 PM, Dismiss 1:15 PM, Return 5:30 PM; 1 Bus | |
| Thu., 10/24 | V Boys Soccer | New Canaan | Away - New Canaan HS-WTT #1 [Directions] | W 3-1 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Thu., 10/24 | V Girls Cross Country | Hatter Freshmen Invitational | Away - Danbury HS | 4:00 p.m. | 1:45 PM, Dismiss 1:15 PM, Return 5:30 PM; 1 Bus | |
| Fri., 10/25 | V Football | New Canaan | Home - Staples HS-Staples Stadium [Directions] | L 21-41 | ||
| Fri., 10/25 | V Boys Water Polo | Choate Rosemary Hall | Away - Choate Rosemary Hall | 4:30 p.m. | 2:00 PM, Dismiss 1:45 PM, Return 6:30 PM; 1 Bus | |
| Fri., 10/25 | V Field Hockey | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | W 3-1 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Fri., 10/25 | V Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field B (turf) [Directions] | W 1-0 | ||
| Fri., 10/25 | V Girls Swimming and Diving | Westhill/Stamford | Home - Staples HS-Staples High School Pool [Directions] | Staples 99 Westhill 82 | ||
| Fri., 10/25 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 0-3 | 12:00 PM | |
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class LL Divisional Championship | Away - Wickham Park | 3:45 p.m. | ||
| Sat., 10/26 | V Boys Water Polo | Suffield Academy | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class LL Divisional Championship | Away - Wickham Park | 3:10 p.m. | ||
| Sat., 10/26 | Miscellaneous Events | PAL Football | Home - Staples HS-Staples Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/26 | Miscellaneous Events | Adult Rugby | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Mon., 10/28 | V Boys Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | T 1-1 | ||
| Mon., 10/28 | V Girls Swimming and Diving | Fairfield Warde | Home - Staples HS-Staples High School Pool [Directions] | Staples 95 Warde 84 | ||
| Tue., 10/29 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 4-2 | 5:30 PM, Return 8:00 PM; 1 Bus | |
| Tue., 10/29 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | W 3-0 | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Tue., 10/29 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | L 1-3 | TBA (JV will ride with varsity) | |
| Wed., 10/30 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest MS-Pool [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:50 PM, Return 5:00 PM; 1 Bus | |
| Thu., 10/31 | V Boys Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | W 1-0 | 1:30 PM, Return 4:30 PM; 1 Bus | |
| Thu., 10/31 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | W 3-2 | 3:00 PM, Return 5:30 PM (JV will ride with varsity) | |
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Football | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | L 24-35 | 4:30 PM, Return 9:00 PM; 2 Buses | |
| Fri., 11/1 | V Boys Water Polo | Loomis Chaffee School | Away - Loomis Chaffee School | 3:00 p.m. | 1:30 PM, Dismiss 1:15 PM, Return 5:00 PM; 1 Bus | |
| Fri., 11/1 | V Sideline Cheerleading | Football vs. Wilton | Away - Not Listed | 7:00 p.m. | 5:15 PM, Return 9:00 PM; 1 Bus (Destination: Wilton HS) | |
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/1 | V Field Hockey | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | W 2-0 | ||
| Fri., 11/1 | V Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | 3:00 p.m. | ||
| Fri., 11/1 | V Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | W 3-0 | ||
| Sat., 11/2 | V Girls Swimming and Diving | FCIAC Girls Swimming Trials | Away - Greenwich HS-Pool | 4:30 p.m. | 2:15 PM, Dismiss 1:45 PM, Return 6:00 PM; 1 Bus | |
| Mon., 11/4 | V Field Hockey | Ridgefield | Home - Brien McMahon HS-Stadium [Directions] | W 3-1 | 5:00 PM, Return 8:00 PM; 1 Bus | |
| Mon., 11/4 | V Girls Soccer | New Canaan | Home - Wilton HS Varsity Field [Directions] | 5:00 p.m. | 3:00 PM, Return 6:00 PM | |
| Mon., 11/4 | V Girls Swimming and Diving | FCIAC Diving | Away - New Canaan HS | 5:30 p.m. | 3:00 PM, Dismiss TBA, Return 7:30 PM; 1 Bus | |
| Tue., 11/5 | V Boys Soccer | Fairfield Warde | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 11/5 | V Boys Soccer | Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 4-1 | 5:15 PM, Return 7:30 PM; 1 Bus | |
| Tue., 11/5 | V Girls Swimming and Diving | FCIAC Girls Swimming Championships | Away - Greenwich HS-Pool | 6:30 p.m. | 3:30 PM, Return 8:30 PM; 1 Bus | |
| Tue., 11/5 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | 4:00 PM, Return 5:00 PM | |
| Thu., 11/7 | V Field Hockey | Darien | Home - Brien McMahon HS-Stadium [Directions] | T 0-0 | 4:00 PM, Return 7:00 PM | |
| Thu., 11/7 | V Girls Soccer | St. Joseph | Home - Wilton HS-Lilly Field - Turf [Directions] | 5:00 p.m. | ||
| Thu., 11/7 | V Girls Soccer | St. Joseph | Home - Wilton HS-Lilly Field - Turf [Directions] | Cancelled | 3:15 PM, Return 6:00 PM | |
| Fri., 11/8 | V Football | Fairfield Warde | Home - Staples HS-Staples Stadium [Directions] | L 7-12 | ||
| Mon., 11/11 | V Boys Soccer | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | W 3-0 | ||
| Mon., 11/11 | V Girls Volleyball | Newtown | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 11/13 | V Boys Soccer | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | W 3-2 | ||
| Wed., 11/13 | V Field Hockey | New Milford | Home - Staples HS-Ginny Parker Field [Directions] | 2:00 p.m. | ||
| Wed., 11/13 | V Girls Swimming and Diving | CIAC Girls Class LL Diving Championship | Away - Middletown HS-Pool | 5:30 p.m. | ||
| Thu., 11/14 | V Girls Soccer | Brien McMahon | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Fri., 11/15 | V Boys Soccer | Trumbull | Away - Trumbull HS-New Turf Field [Directions] | L 2-1 | ||
| Sat., 11/16 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | L 0-50 | 8:00 AM, Return 1:00 PM | |
| Sat., 11/16 | V Sideline Cheerleading | Football vs. St Joseph | Away - Not Listed | 11:00 a.m. | 9:30 AM, Return 1:00 PM; 1 Bus (Destination: St Joseph HS) | |
| Sat., 11/16 | V Field Hockey | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 12:00 p.m. | ||
| Sat., 11/16 | V Girls Soccer | Farmington | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Girls Class LL Trials | Away - East Hartford HS-Pool | 11:30 a.m. | ||
| Tue., 11/19 | V Field Hockey | Norwalk | Home - Weston HS-WHS Stadium Field [Directions] | 6:30 p.m. | 5:00 PM, Return 7:30 PM | |
| Tue., 11/19 | V Girls Soccer | Glastonbury | Home - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | 3:15 PM, Return 7:00 PM | |
| Tue., 11/19 | V Girls Swimming and Diving | CIAC Girls Class LL Finals | Away - Bad-Site Wesleyan University-Freeman Athletic Center | 7:00 p.m. | ||
| Thu., 11/21 | V Girls Swimming and Diving | CIAC Girls State Open Diving | Away - Middletown HS-Pool | 5:30 p.m. | ||
| Sat., 11/23 | V Field Hockey | Darien | Away - Wethersfield HS-Cottone Field [Directions] | 2:00 p.m. | 11:15 AM, Return 3:00 PM | |
| Sat., 11/23 | V Field Hockey | Darien | Away - Wethersfield HS-Cottone Field [Directions] | 2:00 p.m. | ||
| Sun., 11/24 | V Girls Swimming and Diving | CIAC Girls State Open Swimming | Away - Yale | 2:00 p.m. | ||
| Thu., 11/28 | V Football | Greenwich | Home - Staples HS-Staples Stadium [Directions] | L 14-38 | ||
| Thu., 12/5 | V Boys Ice Hockey | Newington Coop (Scrim.) | Home - Milford Ice Pavillion-Ice Rink [Directions] | 5:15 p.m. | ||
| Sat., 12/7 | V Boys Ice Hockey | North Haven (Scrim.) | Home - Longshore Rink @ Westport-PAL Rink @ Longshore [Directions] | 3:00 p.m. | ||
| Sat., 12/7 | V Girls Ice Hockey | Wilton/Norwalk/McMahon (Scrim.) | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:00 p.m. | ||
| Tue., 12/10 | V Boys Basketball | Stratford (Scrim.) | Away - Stratford HS-Gym [Directions] | 3:30 p.m. | 2:30 PM, Return 5:00 PM; 1 Bus | |
| Tue., 12/10 | V Girls Basketball | Kolbe Cathedral (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/11 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 10-4 | ||
| Thu., 12/12 | V Boys Basketball | Foran (Scrim.) | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 6:30 p.m. | 4:30 PM, Return 7:30 PM; 1 Bus | |
| Thu., 12/12 | V Girls Basketball | Norwalk (Scrim.) | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:00 p.m. | 3:30 PM, Return 6:00 PM | |
| Sat., 12/14 | V Boys Basketball | Jonathan Law (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/14 | V Boys Ice Hockey | JBWA (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:45 p.m. | 3:30 PM, Return 8:30 PM (Stop in Milford) | |
| Sat., 12/14 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 6-1 | ||
| Wed., 12/18 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 1-2 | ||
| Wed., 12/18 | V Wrestling | Stamford | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/18 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 7-2 | ||
| Thu., 12/19 | V Girls Basketball | Bethel | Away - Bethel HS-Gym [Directions] | L 44-49 | 2:30 PM, Return 7:00 PM; 1 Bus | |
| Fri., 12/20 | V Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | W 63-45 | ||
| Fri., 12/20 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | L 7-3 | TBA | Staples provided bus |
| Sat., 12/21 | V Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | W 63-50 | 11:00 AM, Return 3:00 PM; 1 Bus | |
| Sat., 12/21 | V Boys Ice Hockey | East Haven Coop | Away - East Haven HS-Veterans Rink [Directions] | L 2-4 | 10:30 AM, Return 3:15 PM (Stop at Milford Ice pavilion coming and going to East Haven) | |
| Sat., 12/21 | V Wrestling | Lancer Invitational 2019-2020 | Away - Waterford HS - official -Francis X. Sweeney Field House | 10:00 a.m. | 6:30 AM, Return 6:00 PM | |
| Mon., 12/23 | V Boys Basketball | Weston | Home - Staples HS-Staples Gym [Directions] | W 73-49 | ||
| Mon., 12/23 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 58-46 | 4:15 PM, Return 7:00 PM | |
| Fri., 12/27 | V Boys Basketball | Pomperaug | Home - Newtown HS-Gym [Directions] | W 77-70 | ||
| Fri., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away - Floyd Little Athletic Center | 12:00 p.m. | 9:45 AM, Return 5:00 PM | |
| Fri., 12/27 | V Wrestling | Danbury | Away - Danbury HS-New Gym [Directions] | 12:00 p.m. | 10:00 AM, Return 1:30 PM | |
| Fri., 12/27 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 57-42 | 11:30 AM, Dismiss TBA | |
| Sat., 12/28 | V Boys Ice Hockey | Amity | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 1-5 | ||
| Sat., 12/28 | V Wrestling | Danbury, Bacon Academy, Bethel, Bristol Eastern, Brookfield, Coventry, Darien, East Haven, Enfield, Abbott Tech, New Canaan, New Milford, Newington, Northfield Mt. Hampton (MA), Norwalk, Putnam Vo-Tech (MA), Ridgefield, Stamford, Wilton | Away - Danbury HS | 10:00 a.m. | 6:45 AM, Return 7:00 PM | |
| Sat., 12/28 | V Girls Basketball | Fairfield Warde | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 56-26 | ||
| Mon., 12/30 | V Boys Basketball | Westhill | Home - Newtown HS-Gym [Directions] | W 73-30 | 1:00 PM, Dismiss TBA | |
| Mon., 12/30 | V Wrestling | ENFIELD DUALS | Away - Enfield HS-EHS GYM - MAIN | 7:00 a.m. | 6:15 AM, Return 4:00 PM | |
| Mon., 12/30 | V Girls Ice Hockey | Avon | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-2 | ||
| Fri., 1/3 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | W 79-55 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Fri., 1/3 | V Girls Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | W 68-13 | ||
| Fri., 1/3 | V Girls Indoor Track | 26th Hispanic Games | Away - Armory Track | 5:00 p.m. | 2:30 PM, Dismiss TBA, Return 10:00 PM | |
| Sat., 1/4 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 6-0 | ||
| Sat., 1/4 | V Boys Indoor Track | FCIAC Qualifier #1 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/4 | V Boys Indoor Track | Elm City Coaches Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 6:45 AM, Return 2:00 PM | |
| Sat., 1/4 | V Boys Indoor Track | Hispanic Games | Away - Armory Track | TBA | TBA | |
| Sat., 1/4 | V Wrestling | Warde Wrestling Invitational | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | 6:45 AM, Return 5:00 PM | |
| Sat., 1/4 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | L 6-5 | 6:30 PM (1st Student - 6:30 - Stamford Only - Staples provides own bus) | |
| Sat., 1/4 | V Girls Indoor Track | FCIAC Qualifier #1 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/4 | V Girls Indoor Track | Elm City Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 7:00 AM, Return 2:00 PM | |
| Tue., 1/7 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 70-58 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Tue., 1/7 | V Girls Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | W 59-44 | ||
| Wed., 1/8 | V Boys Alpine Skiing | Ski race #1 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 6:00 PM | |
| Wed., 1/8 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 1-6 | 5:10 PM, Return 9:20 PM | |
| Wed., 1/8 | V Wrestling | Trumbull | Away - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | 4:00 PM, Return 7:00 PM | |
| Wed., 1/8 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 0-9 | ||
| Fri., 1/10 | V Boys Basketball | Trinity Catholic | Home - Staples HS-Staples Gym [Directions] | W 66-59 | ||
| Fri., 1/10 | V Boys Indoor Track | Yale Invitational | Away - Yale University-Coxe Cage | 1:00 p.m. | 11:00 AM, Dismiss 10:30 AM, Return 6:00 PM | |
| Fri., 1/10 | V Girls Basketball | Trinity Catholic | Away - Trinity Catholic-Gym | W 58-42 | 2:00 PM, Dismiss 1:55 PM, Return 5:00 PM; 1 Bus | |
| Fri., 1/10 | V Girls Gymnastics | Greenwich, Norwalk | Away - Greenwich YWCA [Directions] | 128.50 | 4:00 PM, Return 7:00 PM | |
| Fri., 1/10 | V Girls Indoor Track | 38th Yale Interscholastic Classic | Away - Yale University-Bellizzi Asian Studies Academy | 1:00 p.m. | ||
| Sat., 1/11 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-LIberty Rink [Directions] | W 5-3 | 5:50 PM, Return 9:25 PM | |
| Sat., 1/11 | V Boys Indoor Track | FCIAC Qualifier #2 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/11 | V Boys Indoor Track | Yale Invitational | Away - Yale University-Coxe Cage | 9:00 a.m. | TBA | |
| Sat., 1/11 | V Wrestling | John Chacho Dual Tournament (4 mats) | Home - Staples HS-Staples Gym [Directions] | 8:45 a.m. | ||
| Sat., 1/11 | V Girls Gymnastics | Pomperaug Invitational | Away - Pomperaug HS-Main Gym | 123.7 | 8:00 AM, Return 3:00 PM | |
| Sat., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 9-5 | 4:00 PM (1st Student - 4pm – Stop at Exit 18 – Shelton Ice Rink) | |
| Sat., 1/11 | V Girls Indoor Track | FCIAC Qualifier #2 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/11 | V Girls Indoor Track | 38th Yale Interscholastic Classic | Away - Yale University-Bellizzi Asian Studies Academy | 8:30 a.m. | ||
| Mon., 1/13 | V Boys Swimming and Diving | Wilton | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Mon., 1/13 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-Stadium [Directions] | L 5-3 | 2:30 PM (2:30 - Bob - Stop at Exit 16 - Wonderland) | |
| Tue., 1/14 | V Boys Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | W 71-36 | ||
| Tue., 1/14 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 43-35 | 5:15 PM, Return 8:15 PM; 1 Bus | |
| Tue., 1/14 | V Girls Gymnastics | Fairfield Ludlowe, Foran | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 129.9 | ||
| Tue., 1/14 | V Girls Gymnastics | Fairfield Warde | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 5:00 PM, Return 8:00 PM | |
| Wed., 1/15 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | L 0-3 | 6:10 PM, Return 10:15 PM | |
| Wed., 1/15 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 3:30 p.m. | 2:00 PM, Dismiss 1:45 PM, Return 4:30 PM | |
| Wed., 1/15 | V Wrestling | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | 2:45 PM, Return 6:00 PM | |
| Thu., 1/16 | V Boys Alpine Skiing | Ski race #2 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 6:00 PM | |
| Thu., 1/16 | V Boys Alpine Skiing | Wilton, Lauralton Hall, Cheshire Academy, Fairfield Prep, Woodstock Academy | Away - Southington Ski Mountain | 4:30 p.m. | ||
| Thu., 1/16 | V Girls Alpine Skiing | Ski race #2 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | TBA, Dismiss 1:30 PM | |
| Thu., 1/16 | V Girls Alpine Skiing | Wilton, Lauralton Hall, Cheshire Academy, Fairfield Prep, Woodstock Academy | Away - Southington Ski Mountain | 4:30 p.m. | ||
| Fri., 1/17 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 59-71 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Fri., 1/17 | V Boys Ice Hockey | Ridgefield | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 1-4 | ||
| Fri., 1/17 | V Girls Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | L 40-44 | ||
| Fri., 1/17 | V Girls Gymnastics | Westhill, New Canaan, Norwalk, Stamford | Away - Westhill HS-New Gym [Directions] | 129.55 | 3:30 PM, Return 6:00 PM | |
| Fri., 1/17 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 6-5 OT | 4:15 PM (1st Student - 4:15 – stop at Exit 18 - Shelton Ice Rink) | |
| Sat., 1/18 | V Boys Indoor Track | FCIAC Qualifier #3 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/18 | V Boys Indoor Track | New Balance Games | Away - Armory Track | TBA | ||
| Sat., 1/18 | V Wrestling | New Milford Wrestling Tournament | Away - New Milford HS-Main Gym - NMHS | Cancelled | 6:15 AM, Return 6:00 PM | |
| Sat., 1/18 | V Competitive Cheerleading | Seymour High School Wildcat Open | Away - Seymour HS | 9:00 a.m. | 7:00 AM, Return 1:00 PM | |
| Sat., 1/18 | V Girls Indoor Track | FCIAC Qualifier #3 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/18 | V Girls Indoor Track | SCC Invitational | Away - Floyd Little Athletic Center | TBA | 7:00 AM, Dismiss TBA, Return 7:30 PM | |
| Tue., 1/21 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 58-63 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Tue., 1/21 | V Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | W 67-62(ot) | ||
| Wed., 1/22 | V Boys Alpine Skiing | Ski race #3 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 6:00 PM | |
| Wed., 1/22 | V Boys Ice Hockey | Trinity Catholic | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 6-2 | ||
| Wed., 1/22 | V Boys Indoor Track | SCC Coaches Invitational | Away - Floyd Little Athletic Center | 2:00 p.m. | 1:45 PM, Return 7:00 PM | |
| Wed., 1/22 | V Boys Swimming and Diving | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/22 | V Wrestling | Greenwich | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/22 | V Girls Alpine Skiing | Ski race #3 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | TBA, Dismiss 1:30 PM | |
| Thu., 1/23 | V Girls Gymnastics | TBA, Trumbull | Away - TBA | 6:00 p.m. | 4:15 PM, Return 7:45 PM | |
| Thu., 1/23 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 1-5 | ||
| Fri., 1/24 | V Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | W 65-47 | ||
| Fri., 1/24 | V Boys Indoor Track | H - K Invitational | Away - Floyd Little Athletic Center | 3:00 p.m. | 12:45 PM, Dismiss 12:15 PM, Return 8:00 PM | |
| Fri., 1/24 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 6:00 p.m. | 4:30 PM, Return 7:30 PM | |
| Fri., 1/24 | V Girls Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | W 60-44 | ||
| Sat., 1/25 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 4-5 | ||
| Sat., 1/25 | V Boys Indoor Track | Hillhouse Classic | Away - Floyd Little Athletic Center | 10:00 a.m. | 7:45 AM, Return 3:00 PM | |
| Sat., 1/25 | V Boys Indoor Track | FCIAC Qualifier #4 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/25 | V Wrestling | Carl Snitkin Memorials Duals | Away - Norwich Free Academy-Alumni Gym | 9:45 a.m. | 6:30 AM, Return 4:30 PM | |
| Sat., 1/25 | V Girls Indoor Track | FCIAC Qualifier #4 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/25 | V Girls Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:00 AM, Dismiss TBA, Return 3:00 PM | |
| Mon., 1/27 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 84-62 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Mon., 1/27 | V Girls Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | W 69-26 | ||
| Mon., 1/27 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | L 4-5 OT | 1:45 PM (1st student – 1:45- Wintergarden Ice rink - Staples provides own bus) | |
| Tue., 1/28 | V Girls Gymnastics | Wilton | Away - Wilton HS-Aux Gym [Directions] | 138.75 | 3:00 PM, Return 5:30 PM | |
| Wed., 1/29 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 0-7 | 3:10 PM, Return 7:15 PM | |
| Wed., 1/29 | V Boys Swimming and Diving | Westhill/Stamford | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/29 | V Wrestling | Westhill | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 3:30 PM, Return 6:00 PM | |
| Wed., 1/29 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena-Red Rink [Directions] | L 2-6 | 2:15 PM (1st Student - 2:15 – stop at Exit 18 – Newington Ice Rink) | |
| Thu., 1/30 | V Boys Alpine Skiing | Ski race #4 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 6:00 PM | |
| Thu., 1/30 | V Boys Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | L 59-52 | ||
| Thu., 1/30 | V Boys Swimming and Diving | Danbury | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Thu., 1/30 | V Girls Alpine Skiing | Ski race #4 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | TBA, Dismiss 1:30 PM | |
| Thu., 1/30 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 60-45 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Fri., 1/31 | Miscellaneous Events | Red & White Charity Ball | Home - TBA [Directions] | 7:00 p.m. | ||
| Sat., 2/1 | V Boys Indoor Track | Western Division Championship | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/1 | V Wrestling | T.F.C. Kevin Miller Duals | Away - East Hartford HS | 9:30 a.m. | 6:45 AM, Return 4:30 PM | |
| Sat., 2/1 | V Competitive Cheerleading | Fairfield Ludlowe High School 2nd Annual Open | Away - Fairfield Ludlowe HS | 9:00 a.m. | TBA, Return 1:00 PM | |
| Sat., 2/1 | V Girls Gymnastics | Trumbull, Foran, Norwalk, St. Joseph | Away - Next Dimension [Directions] | 126.5 | 5:00 PM, Return 7:30 PM | |
| Sat., 2/1 | V Girls Indoor Track | Western Division Championship | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/1 | Miscellaneous Events | County Assembly Charity Ball | Home - TBA [Directions] | 7:00 p.m. | ||
| Mon., 2/3 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | L 2-3(OT) | 6:00 PM, Return 10:00 PM | |
| Mon., 2/3 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | 1:30 PM, Dismiss 1:15 PM, Return 4:30 PM | |
| Mon., 2/3 | V Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | W 73-55 | 2:30 PM, Return 6:00 PM; 1 Bus | |
| Tue., 2/4 | V Girls Gymnastics | New Milford, Norwalk | Away - New Milford HS-Small Gym - NMHS [Directions] | 138.95 | 3:00 PM, Return 6:00 PM | |
| Tue., 2/4 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Champions - Cromwell-Lower Rink [Directions] | L 1-3 | 2:30 PM (Bob - 2:30 at SHS - Stop Exit 18) | |
| Wed., 2/5 | V Boys Ice Hockey | Masuk | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 5-2 | ||
| Wed., 2/5 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 4:30 PM | |
| Wed., 2/5 | V Wrestling | Darien | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/6 | V Boys Alpine Skiing | Ski race #5 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | 1:45 PM, Dismiss 1:30 PM, Return 6:00 PM | |
| Thu., 2/6 | V Boys Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | W 72-70 | ||
| Thu., 2/6 | V Boys Indoor Track | FCIAC Championships | Away - Norwalk HS-Testa Field | 4:30 p.m. | ||
| Thu., 2/6 | V Wrestling | Fairfield Warde, Fitch, Ridgefield, Shelton | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | 2:30 PM, Return 6:00 PM | |
| Thu., 2/6 | V Girls Alpine Skiing | Ski race #5 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | TBA, Dismiss 1:30 PM | |
| Thu., 2/6 | V Girls Basketball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | W 60-31 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Thu., 2/6 | V Girls Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Sat., 2/8 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 2-4 | 4:10 PM, Return 8:15 PM | |
| Sat., 2/8 | V Boys Indoor Track | Darien, Fairfield Ludlowe | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/8 | V Competitive Cheerleading | FCIAC Cheerleading Competition | Away - TBA | 9:00 a.m. | 7:00 AM, Return 1:00 PM | |
| Sat., 2/8 | V Girls Gymnastics | Darien, Norwalk | Away - Darien YMCA [Directions] | 132.6 | 3:00 PM, Return 6:00 PM | |
| Sat., 2/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 10-5 | ||
| Mon., 2/10 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 62-51 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Mon., 2/10 | V Boys Swimming and Diving | Ridgefield | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/10 | V Girls Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | W 44-32 | ||
| Mon., 2/10 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 8-0 | ||
| Tue., 2/11 | V Wrestling | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/12 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | T 1-1 | 4:00 PM, Return 8:45 PM (Stop in Milford on the way to Shelton and on the return) | |
| Wed., 2/12 | V Boys Swimming and Diving | Trumbull | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/12 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-Blue [Directions] | W 3-1 | 1:30 PM (BOB - 1:30 from SHS - Stop @ exit 18) | |
| Thu., 2/13 | V Boys Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | W 86-65 | ||
| Thu., 2/13 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 39-24 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Fri., 2/14 | V Wrestling | FCIAC's | Away - New Canaan HS-Main Gym | 4:30 p.m. | 2:30 PM, Return 6:00 PM | |
| Sat., 2/15 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | W 3-0 | 12:15 PM, Return 5:00 PM (Stop in Milford on the way to Northford and on the return) | |
| Sat., 2/15 | V Wrestling | FCIAC Wrestling Championship | Away - New Canaan HS-Main Gym | 10:00 a.m. | 2:30 PM, Return 6:00 PM | |
| Sat., 2/15 | V Girls Gymnastics | FCIAC Championships | Away - Westhill HS-Main Gym | 10:00 a.m. | 8:00 AM, Return 2:00 PM | |
| Sat., 2/15 | V Girls Gymnastics | FCIAC Gymnastics Championship | Away - Westhill HS-New Gym | 125.05 | ||
| Mon., 2/17 | V Boys Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | L 71-75 | ||
| Mon., 2/17 | V Boys Ice Hockey | New Milford | Away - Canterbury School-Ice Rink [Directions] | L 0-3 | 5:15 PM, Return 10:00 PM | |
| Mon., 2/17 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 49-24 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Mon., 2/17 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 1-5 | ||
| Wed., 2/19 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 66-57 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Wed., 2/19 | V Boys Ice Hockey | Greenwich | Home - Milford Ice Pavillion-Ice Rink [Directions] | L 0-4 | ||
| Wed., 2/19 | V Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | W 73-34 | ||
| Fri., 2/21 | V Wrestling | CIAC Class LL Divisional Championship | Away - Trumbull HS-Gym | 3:00 p.m. | ||
| Sat., 2/22 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | L 1-4 | 12:45 PM, Return 5:00 PM | |
| Sat., 2/22 | V Wrestling | CIAC Class LL Divisional Championship | Away - Trumbull HS-Gym | 9:00 a.m. | ||
| Sat., 2/22 | V Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Sat., 2/22 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Mon., 2/24 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | L 61-64 | 4:00 PM, Return 8:00 PM; 1 Bus | |
| Mon., 2/24 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 5-4 | ||
| Tue., 2/25 | V Girls Basketball | Greenwich | Home - Trumbull HS-Gym [Directions] | 6:00 p.m. | 4:00 PM, Return 7:15 PM | |
| Wed., 2/26 | V Boys Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | W 72-65 | ||
| Wed., 2/26 | V Boys Ice Hockey | Milford Coop | Home - Milford Ice Pavillion-Ice Rink [Directions] | W 1-0 | ||
| Thu., 2/27 | V Girls Basketball | Ridgefield | Home - Trumbull HS [Directions] | 7:00 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 3:00 p.m. | ||
| Sat., 2/29 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 12:00 p.m. | 10:15 AM, Return 1:00 PM | |
| Sat., 2/29 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 9:00 a.m. | ||
| Sat., 2/29 | V Competitive Cheerleading | NECA or Oxford | Away - TBA | 9:00 a.m. | 7:00 AM, Return 1:00 PM | |
| Sat., 2/29 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium | 9:00 a.m. | 7:00 AM, Return 1:00 PM | |
| Mon., 3/2 | V Girls Basketball | Kennedy | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 3/3 | V Boys Swimming and Diving | FCIAC Swimming Trials | Away - Greenwich HS-Pool | 5:30 p.m. | 2:30 PM, Return 8:00 PM | |
| Wed., 3/4 | V Boys Swimming and Diving | FCIAC Diving Championship | Away - Westhill HS-Westhill Pool | 4:30 p.m. | 2:30 PM, Return 7:00 PM | |
| Thu., 3/5 | V Boys Swimming and Diving | FCIAC Boys Swim Finals | Away - Greenwich HS-Pool | 6:30 p.m. | 4:30 PM, Return 9:00 PM | |
| Thu., 3/5 | V Girls Basketball | Wilbur Cross | Home - Staples HS-Staples Gym [Directions] | 6:30 p.m. | ||
| Fri., 3/6 | V Boys Basketball | Foran (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 3/7 | V Competitive Cheerleading | State Cheerleading Competition | Away - TBA | 9:00 a.m. | 7:00 AM, Return 1:00 PM | |
| Sat., 3/7 | V Girls Gymnastics | CIAC State Open Championship | Away - New Milford HS-Main Gym - NMHS | Postponed | ||
| Mon., 3/9 | V Boys Ice Hockey | Hall | Away - Veterans Memorial Ice Rink West Hartford CT-Ice Rink [Directions] | 7:20 p.m. | 2:15 PM, Return 9:45 PM | |
| Mon., 3/9 | V Girls Basketball | Glastonbury | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Tue., 3/10 | V Boys Basketball | Enfield | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Boys Class LL Diving Championship | Away - Middletown HS-MHS Pool | Cancelled | ||
| Sat., 3/14 | V Boys Rugby | Fordham Prep (NY) | Away - Fordham Prep School | Cancelled | ||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Boys Class LL Trials | Away - East Hartford HS-Pool | Cancelled | ||
| Sat., 3/14 | V Competitive Cheerleading | Team of the Year Cheerleading Competition | Away - TBA | Cancelled | 7:00 AM, Return 1:00 PM | |
| Tue., 3/17 | V Boys Swimming and Diving | CIAC Boys Class LL Finals | Away - Wesleyan University-Pool | Cancelled | ||
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Boys State Open Diving | Away - Bulkeley HS-Pool | Cancelled | ||
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Boys State Open Swimming | Away - Yale | Cancelled | ||
| Sat., 3/21 | V Competitive Cheerleading | Regional Cheerleading Competition | Away - TBA | Cancelled | 7:00 AM, Return 1:00 PM | |
| Sun., 3/22 | V Boys Rugby | St. Anthonys (NY) | Away - St. Anthony's HS | Cancelled | 11:00 AM | |
| Thu., 3/26 | V Boys Lacrosse | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Stadium [Directions] | Cancelled | 2:45 PM, Return 5:30 PM | |
| Fri., 3/27 | V Baseball | Weston (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 3/28 | V Boys Rugby | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Sat., 3/28 | V Girls Lacrosse | Bishop Guertin (NH), Cheshire, Fairfield Ludlowe, Greenwich, TBA, Pleasantville (NY), Weston | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Sat., 3/28 | V Girls Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | Cancelled | ||
| Sun., 3/29 | V Softball | Pomperaug (Scrim.) | Away - Danbury Sports Dome [Directions] | Cancelled | ||
| Mon., 3/30 | V Baseball | Trumbull (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 3/31 | V Baseball | Fairfield Warde (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/1 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | Cancelled | 2:30 PM, Return 5:30 PM | |
| Wed., 4/1 | V Boys Lacrosse | Glastonbury (Scrim.) | Away - Glastonbury HS-Field 1 [Directions] | Cancelled | 2:30 PM, Return 6:00 PM | |
| Wed., 4/1 | V Boys Volleyball | Shelton (Scrim.) | Away - Shelton HS-High School - Murray Gymnasium [Directions] | Cancelled | 3:00 PM, Return 6:00 PM | |
| Wed., 4/1 | V Girls Lacrosse | Fairfield Warde (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Wed., 4/1 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Staples HS-Staples High School Pool [Directions] | Cancelled | ||
| Thu., 4/2 | V Girls Rugby | Southington | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Fri., 4/3 | V Boys Rugby | Simsbury | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Fri., 4/3 | V Girls Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | Cancelled | ||
| Sat., 4/4 | V Baseball | Notre Dame-West Haven | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 4/4 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | Cancelled | TBA, Return 8:00 PM | |
| Sat., 4/4 | V Girls Outdoor Track | All American Classic | Away - New Kent HS | Cancelled | TBA | |
| Sat., 4/4 | V Softball | Masuk | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Mon., 4/6 | V Boys Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Tue., 4/7 | V Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | Cancelled | 2:30 PM, Return 5:15 PM | |
| Tue., 4/7 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Tue., 4/7 | V Girls Lacrosse | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Tue., 4/7 | V Girls Tennis | Bridgeport Central | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/8 | V Baseball | Masuk | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/8 | V Boys Lacrosse | Conestoga (PA) | Away - University of Pennsylvania | Cancelled | 8:00 AM, Return 2:30 PM | |
| Wed., 4/8 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | Cancelled | 2:00 PM, Return 5:00 PM | |
| Wed., 4/8 | V Girls Tennis | Danbury | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/9 | V Baseball | Amity | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Thu., 4/9 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Cancelled | 3:00 PM, Return 5:30 PM | |
| Thu., 4/9 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | 2:45 PM, Return 5:15 PM | |
| Fri., 4/10 | V Boys Golf | Brien McMahon | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Mon., 4/13 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Mon., 4/13 | V Boys Golf | Stamford | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | Cancelled | ||
| Mon., 4/13 | V Boys Tennis | Trinity Catholic | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/13 | V Softball | Bridgeport Central | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Mon., 4/13 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | Cancelled | 2:30 PM, Return 5:00 PM | |
| Tue., 4/14 | V Boys Golf | Trinity Catholic | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Tue., 4/14 | V Boys Outdoor Track | Norwalk | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 4/14 | V Boys Tennis | Norwalk | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/14 | V Girls Golf | Darien | Away - Country Club of Darien [Directions] | Cancelled | 2:10 PM, Return 5:00 PM | |
| Tue., 4/14 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Cancelled | 2:30 PM, Return 5:30 PM | |
| Tue., 4/14 | V Girls Outdoor Track | Norwalk | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 4/14 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Wed., 4/15 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | Cancelled | 2:00 PM, Return 5:30 PM | |
| Wed., 4/15 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:05 PM | |
| Wed., 4/15 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | Cancelled | 2:30 PM, Return 6:00 PM | |
| Wed., 4/15 | V Girls Golf | Darien | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Wed., 4/15 | V Softball | Danbury | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Wed., 4/15 | V Girls Tennis | Trumbull | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/16 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | Cancelled | ||
| Thu., 4/16 | V Boys Lacrosse | Cold Spring Harbor (NY) | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Thu., 4/16 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | Cancelled | 2:10 PM, Return 5:00 PM | |
| Thu., 4/16 | V Girls Lacrosse | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Thu., 4/16 | V Softball | St. Joseph | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Fri., 4/17 | V Baseball | Trinity Catholic | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 4/17 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Sat., 4/18 | V Baseball | Hall | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 4/18 | V Boys Lacrosse | Bishop Guertin (NH) | Away - Brown University | Cancelled | 8:30 AM, Return 3:00 PM | |
| Sat., 4/18 | V Boys Outdoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | Cancelled | 7:45 AM, Return 3:00 PM | |
| Sat., 4/18 | V Girls Outdoor Track | Viking International | Away - Walt Whitman HS | Cancelled | TBA | |
| Mon., 4/20 | V Baseball | Norwalk | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 4/20 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Mon., 4/20 | V Boys Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Mon., 4/20 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Mon., 4/20 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/21 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Cancelled | 2:45 PM, Return 5:30 PM | |
| Tue., 4/21 | V Boys Outdoor Track | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 4/21 | V Boys Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/21 | V Girls Golf | Danbury | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Tue., 4/21 | V Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Tue., 4/21 | V Girls Outdoor Track | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 4/21 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Wed., 4/22 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | 2:30 PM, Return 5:30 PM | |
| Wed., 4/22 | V Boys Golf | Fairfield Warde | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Wed., 4/22 | V Boys Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | ||
| Wed., 4/22 | V Boys Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Wed., 4/22 | V Softball | Trumbull | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Thu., 4/23 | V Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Thu., 4/23 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:05 PM | |
| Thu., 4/23 | V Girls Golf | Fairfield Warde | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Thu., 4/23 | V Girls Outdoor Track | Penn Relays | Away - University of Pennsylvania | Cancelled | TBA | |
| Thu., 4/23 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | Cancelled | TBA | |
| Thu., 4/23 | V Girls Tennis | Brien McMahon | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/24 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | Cancelled | 2:30 PM, Return 5:30 PM | |
| Fri., 4/24 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | Cancelled | 1:00 PM, Dismiss 12:30 PM, Return 5:45 PM | |
| Fri., 4/24 | V Boys Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Fri., 4/24 | V Girls Lacrosse | Guilford | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Fri., 4/24 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | Cancelled | TBA | |
| Fri., 4/24 | V Softball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Sat., 4/25 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | Cancelled | 5:15 PM, Return 8:00 PM | |
| Sat., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | Cancelled | 7:00 AM, Return 1:00 PM | |
| Sat., 4/25 | V Girls Lacrosse | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Mon., 4/27 | V Baseball | Greenwich | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Lacrosse | Pleasantville (NY) | Away - Pleasantville HS-N:1 | Cancelled | 2:30 PM, Return 5:45 PM | |
| Mon., 4/27 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Mon., 4/27 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Tue., 4/28 | V Boys Golf | Norwalk | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Tue., 4/28 | V Boys Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 4/28 | V Girls Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Tue., 4/28 | V Girls Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Wed., 4/29 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | Cancelled | 2:30 PM, Return 5:30 PM | |
| Wed., 4/29 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | Cancelled | 2:30 PM, Return 6:00 PM | |
| Wed., 4/29 | V Softball | Brien McMahon | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Thu., 4/30 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Cancelled | 2:00 PM, Return 5:00 PM | |
| Thu., 4/30 | V Boys Tennis | Stamford | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/30 | V Girls Golf | Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Thu., 4/30 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Cancelled | 4:00 PM, Return 7:00 PM | |
| Thu., 4/30 | V Girls Rugby | Fairfield | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Thu., 4/30 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Fri., 5/1 | V Baseball | Fairfield Ludlowe | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 5/1 | V Boys Outdoor Track | Middletown Invitational FR & SO | Away - Middletown HS | Cancelled | 1:00 PM, Dismiss 12:30 PM, Return 6:30 PM | |
| Fri., 5/1 | V Boys Rugby | Fairfield | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Fri., 5/1 | V Boys Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Fri., 5/1 | V Girls Outdoor Track | Middletown Invitational FR/SO | Away - Middletown HS | Cancelled | TBA | |
| Fri., 5/1 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | Cancelled | 2:00 PM, Return 5:00 PM | |
| Sat., 5/2 | V Boys Lacrosse | Rye (NY) | Away - Rye HS | Cancelled | 5:00 PM, Return 8:30 PM | |
| Sat., 5/2 | V Boys Outdoor Track | Middletown Invitational Varsity | Away - Middletown HS | Cancelled | 10:30 AM, Return 4:00 PM | |
| Sat., 5/2 | V Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | Cancelled | 1:00 PM, Return 5:00 PM (Motor Coach) | |
| Sat., 5/2 | V Girls Outdoor Track | Middletown Invitational Varsity | Away - Middletown HS | Cancelled | TBA | |
| Mon., 5/4 | V Boys Lacrosse | Westhill | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Mon., 5/4 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | Cancelled | 2:00 PM, Return 5:00 PM (Please schedule a separate bus for JV return) | |
| Mon., 5/4 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | Cancelled | 2:00 PM, Return 6:30 PM | |
| Mon., 5/4 | V Girls Lacrosse | Rye (NY) | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Tennis | Ridgefield | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/5 | V Boys Outdoor Track | Greenwich | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 5/5 | V Boys Tennis | Darien | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/5 | V Girls Golf | New Canaan | Away - CCNC [Directions] | Cancelled | 2:10 PM, Return 5:00 PM | |
| Tue., 5/5 | V Girls Outdoor Track | Greenwich | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 5/5 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Wed., 5/6 | V Baseball | Stamford | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/6 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | Cancelled | 2:30 PM, Return 6:00 PM | |
| Wed., 5/6 | V Girls Golf | Trumbull | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Wed., 5/6 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | Cancelled | 2:00 PM, Return 5:00 PM | |
| Thu., 5/7 | V Boys Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Thu., 5/7 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | Cancelled | TBA | |
| Thu., 5/7 | V Boys Tennis | St. Joseph | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Thu., 5/7 | V Girls Golf | Wilton | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Thu., 5/7 | V Girls Lacrosse | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Thu., 5/7 | V Girls Outdoor Track | Loucks Games | Away - White Plains HS | Cancelled | TBA | |
| Thu., 5/7 | V Girls Rugby | Simsbury | Away - Holden Field-Turf [Directions] | Cancelled | 4:00 PM, Return 7:00 PM | |
| Thu., 5/7 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Fri., 5/8 | V Baseball | Ridgefield | Away - Governor Field [Directions] | Cancelled | 2:00 PM, Return 5:30 PM | |
| Fri., 5/8 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | Cancelled | TBA | |
| Fri., 5/8 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Cancelled | 5:00 PM, Return 8:00 PM | |
| Fri., 5/8 | V Boys Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Fri., 5/8 | V Girls Outdoor Track | Loucks Games | Away - White Plains HS | Cancelled | TBA | |
| Fri., 5/8 | V Softball | Ridgefield | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Sat., 5/9 | V Boys Lacrosse | Greenwich | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Sat., 5/9 | V Boys Outdoor Track | Greater Hartford Invitational | Away - East Hartford HS | Cancelled | 6:30 AM, Return 11:00 AM | |
| Sat., 5/9 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | Cancelled | TBA | |
| Sat., 5/9 | V Boys Rugby | Darien | Away - Royle School Field [Directions] | Cancelled | 11:30 AM, Return 2:00 PM | |
| Sat., 5/9 | V Girls Lacrosse | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Sat., 5/9 | V Girls Outdoor Track | Loucks Games | Away - White Plains HS | Cancelled | TBA | |
| Mon., 5/11 | V Baseball | Darien | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 5/11 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:05 PM | |
| Mon., 5/11 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | Cancelled | 2:30 PM, Return 6:00 PM | |
| Mon., 5/11 | V Girls Golf | Ridgefield | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Mon., 5/11 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Mon., 5/11 | V Girls Tennis | Westhill | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Golf | Wilton | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Outdoor Track | Stamford | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:05 PM | |
| Tue., 5/12 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | Cancelled | 3:00 PM, Return 6:30 PM (motor coach) | |
| Tue., 5/12 | V Girls Outdoor Track | Stamford | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Tue., 5/12 | V Girls Tennis | New Canaan | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Wed., 5/13 | V Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/13 | V Boys Lacrosse | New Fairfield | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Wed., 5/13 | V Boys Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Wed., 5/13 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Thu., 5/14 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Cancelled | 3:00 PM, Return 5:30 PM | |
| Thu., 5/14 | V Boys Tennis | Wilton | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Thu., 5/14 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | Cancelled | 2:00 PM, Return 6:05 PM | |
| Thu., 5/14 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Cancelled | 2:15 PM, Return 5:30 PM | |
| Thu., 5/14 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | Cancelled | 5:00 PM, Return 8:00 PM | |
| Thu., 5/14 | V Girls Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Thu., 5/14 | V Girls Tennis | Wilton | Away - Wilton HS-Wilton Varsity Tennis Courts [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Fri., 5/15 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | Cancelled | 2:30 PM, Return 5:30 PM | |
| Fri., 5/15 | V Boys Outdoor Track | Trumbull | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Fri., 5/15 | V Boys Rugby | State Quarter Finals #6 vs #3 @ #5 vs #4 | Home - TBA [Directions] | Cancelled | ||
| Fri., 5/15 | V Girls Lacrosse | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | Cancelled | ||
| Fri., 5/15 | V Girls Outdoor Track | Trumbull | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Fri., 5/15 | V Softball | Westhill | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Sat., 5/16 | V Boys Lacrosse | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | Cancelled | ||
| Sat., 5/16 | V Boys Outdoor Track | COnnecticut Track Classic | Away - Danbury HS | Cancelled | TBA | |
| Sat., 5/16 | V Boys Tennis | Guilford | Home - Staples HS-Staples Tennis Courts [Directions] | Cancelled | ||
| Mon., 5/18 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | Cancelled | 2:30 PM, Return 5:30 PM | |
| Mon., 5/18 | V Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | Cancelled | ||
| Mon., 5/18 | V Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | Cancelled | ||
| Mon., 5/18 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | Cancelled | 2:10 PM, Return 5:00 PM | |
| Mon., 5/18 | V Girls Rugby | State Semi Finals | Home - TBA [Directions] | Cancelled | ||
| Mon., 5/18 | V Softball | New Canaan | Home - Staples HS-Wakeman Field [Directions] | Cancelled | ||
| Tue., 5/19 | V Boys Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Tue., 5/19 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | Cancelled | 4:45 PM, Return 7:30 PM | |
| Tue., 5/19 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | Cancelled | 1:30 PM, Dismiss 1:00 PM, Return 6:30 PM | |
| Tue., 5/19 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | Cancelled | 2:00 PM, Dismiss 1:30 PM, Return 6:00 PM | |
| Wed., 5/20 | V Baseball | Wilton | Home - Staples HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/20 | V Boys Golf | Darien, Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Wed., 5/20 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | Cancelled | 2:30 PM, Return 6:00 PM | |
| Wed., 5/20 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | Cancelled | 2:30 PM, Return 5:00 PM | |
| Thu., 5/21 | V Boys Golf | Chappa Golf Tournament | Home - Staples HS-Longshore Golf Course [Directions] | Cancelled | ||
| Fri., 5/22 | V Boys Rugby | State Semi Finals lowest seed vs #1, second lowest seed vs #2 | Home - TBA [Directions] | Cancelled | ||
| Fri., 5/22 | V Softball | North Haven | Away - North Haven Athletic Complex-Varsity Softball Field [Directions] | Cancelled | 4:30 PM, Return 8:00 PM | |
| Sat., 5/23 | V Boys Outdoor Track | Dream Invitational | Away - Danbury HS | Cancelled | 5:15 PM, Return 10:00 PM | |
| Mon., 5/25 | V Boys Rugby | State Championship | Home - TBA [Directions] | Cancelled | ||
| Mon., 5/25 | V Girls Rugby | State Championship | Home - TBA [Directions] | Cancelled | ||
| Tue., 5/26 | V Boys Outdoor Track | FCIAC Track Championships | Away - SCSU-Jess Dow Field | Cancelled | 10:45 AM, Dismiss 10:15 AM, Return 5:00 PM | |
| Tue., 5/26 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Cancelled | 2:10 PM, Dismiss 2:00 PM, Return 5:00 PM | |
| Tue., 5/26 | V Girls Outdoor Track | FCIAC Track Championships | Away - SCSU-Jess Dow Field | Cancelled | 1:00 PM, Dismiss 12:30 PM, Return 7:00 PM | |
| Wed., 5/27 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | Cancelled | 2:10 PM, Dismiss 2:00 PM, Return 5:00 PM | |
| Mon., 6/1 | V Girls Golf | New Canaan | Away - New Canaan HS [Directions] | Cancelled | 1:45 PM, Return 5:00 PM | |