October 12, 2020 @ 3:00 pm - 6:30 pm Varsity vs. Wilton @ Wakeman, 4:30; Reserves @ Staples; Frosh @ Wakeman A
October 14, 2020 @ 3:00 pm - 6:30 pm Varsity @ Ridgefield, 4:30 pm; Reserves @ Wakeman E; Frosh @ Wakeman A
October 21, 2020 @ 3:00 pm - 6:00 pm Varsity, reserves @ Staples; frosh vs. Ridgefield @ Wakeman turf, 4:15 pm
November 4, 2020 @ 3:00 pm - 5:00 pm Varsity, playoffs semifinal vs. Brien McMahon, 3 pm @ Staples; Reserves, Frosh @ Wakeman E
August 31, 2021 @ 3:00 pm - 6:00 pm Varsity @ Joel Barlow (scrimmage), 4:15 pm; Reserves, frosh @ Wakeman E, 3-5 pm Joel Barlow High School 100 Black Rock Turnpike, Redding, CT, United States
September 2, 2021 @ 3:00 pm - 6:00 pm Varsity @ Fairfield Prep (scrimmage), 4:15 pm; Reserves, frosh @ Wakeman E, 3-5 pm Fairfield Prep 1073 N. Benson Rd., Fairfield, CT, United States
September 4, 2021 @ 10:00 am - 2:00 pm Varsity @ Wethersfield jamboree, 10 am; Reserves 8-10 @ Wakeman turf Wethersfield HS 411 Wolcott Hill Rd., Wethersfield, United States
September 10, 2021 @ 3:00 pm - 6:00 pm Varsity vs. Ridgefield @ Staples 4 pm; Reserves, frosh @ Wakeman E
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