September 14, 2021 @ 3:00 pm - 7:30 pm Varsity @ New Canaan (Dunning Stadium), 6:30 pm; Reserves vs. New Canaan @ Conner Field, 4 pm; Frosh @ Wakeman E, 3-5 pm New Canaan High School 11 Farm Road, New Canaan, CT, United States
September 18, 2021 @ 9:00 am - 1:00 pm Varsity vs. Greenwich @ Staples, 11:30 am; Reserves vs. Greenwich @ Wakeman turf, 11 am; Frosh vs. Masuk @ Wakeman B, 9 am
September 22, 2021 @ 3:00 pm - 5:00 pm Varsity vs Danbury @ Staples, 4 pm; Reserves vs. Danbury @ Wakeman E, 4 pm; Frosh @ Wakeman A, 3-5
September 24, 2021 @ 8:00 am - 5:00 pm Varsity @ Westhill, 4 pm; Reserves, frosh @ Wakeman E, 3-5 pm; Reserves pasta dinner @ Alfagemes, 5:15; Frosh pasta dinner at Kusters Westhill High School 125 Roxbury Road, Stamford, CT, United States
September 28, 2021 @ 3:00 pm - 6:00 pm Varsity vs. Wilton @ WAKEMAN, 4:15 pm; Reserves vs. Wilton @ Wakeman E, 4:15 pm; Frosh @ Wakeman A
October 1, 2021 @ 3:00 pm - 6:00 pm Varsity, reserves @ Darien, 4 pm; Frosh @ Wakeman E, 3-5 pm; Frosh pasta dinner @ Hills Darien High School 80 High School Lane, Darien, CT, United States
October 5, 2021 @ 3:00 pm - 6:00 pm Varsity @ Fairfield Warde, 4 pm; Reserves vs. Fairfield Warde @ Tunxis, 4 pm; Frosh @ Wakeman A, 3-5 pm Fairfield Warde High School 755 Melville Ave., Fairfield, United States
October 7, 2021 @ 3:00 pm - 6:00 pm Varsity vs. Trumbull @ Staples, 4 pm; Reserves vs. Trumbull @ Wakeman E, 4 pm; Frosh no training
October 11, 2021 @ 3:00 pm - 6:00 pm Varsity @ Stamford, 4 pm; Reserves vs. Stamford @ Rippowam Middle School, 4 pm; Frosh @ Wakeman E
October 13, 2021 @ 4:00 pm - 6:00 pm Varsity @ Central, 4 pm; Reserves vs. Central @ Seaside Park, Bridgeport, 4 pm; Frosh vs. Fairfield Ludlowe @ Sullivan Field, Fairfield, 4 pm
October 15, 2021 @ 3:00 pm - 6:00 pm Varsity @ St. Joseph, 4 pm; JV, Frosh @ Wakeman E, 3-5 pm; Frosh pasta dinner @ Varsovs
October 19, 2021 @ 3:00 pm - 6:00 pm Varsity vs. Norwalk @ Staples, 4 pm; Reserves vs. Norwalk @ Wakeman E, 4 pm; Frosh @ Wakeman A, 3-5 pm
October 22, 2021 @ 3:00 pm - 9:00 pm Varsity vs. Brien McMahon @ Staples, 4 pm; Reserves vs. Brien McMahon @ Wakeman A, 4 pm; Frosh @ Wakeman E, 3-5; Frosh pasta dinner @ Traceys
October 26, 2021 @ 3:00 pm - 6:00 pm Varsity game postponed, training TBD; reserves game postponed, no training; frosh no training
October 29, 2021 @ 8:00 am - 5:00 pm FCIAC quarterfinals vs. Fairfield Warde @ Wakeman turf, 3 pm; Frosh vs. Trumbull @ Wakeman E, 3:45 pm