August 26 @ 4:00 pm - 6:00 pm Varsity scrimmage @ Fairfield Prep, 4 pm Fairfield Prep 1073 N. Benson Rd., Fairfield, CT, United States
September 4 @ 4:00 pm - 6:00 pm Varsity vs New Canaan @ Wakeman, 4 pm; JV vs New Canaan @ Wakeman E, 4 pm; Freshmen vs New Canaan @ Conner Field 4 pm
September 6 @ 4:00 pm - 6:00 pm Varsity @ Brien McMahon, 4 pm; JV vs McMahon @ Roton MS, 4 pm; Freshmen vs McMahon @ Wakeman E, 4 pm Brien McMahon High School 300 Highland Ave., Norwalk, CT, United States
September 10 @ 6:30 pm - 8:30 pm Varsity @ Norwalk away, 6:30 pm; JV vs Norwalk @ West Rocks, 4:15 pm; Freshmen vs Norwalk @ Wakeman E, 4 pm
September 16 @ 4:00 pm - 6:00 pm Varsity vs Darien @ Wakeman, 4 pm; JV vs Darien @ Wakeman #, 4 pm; Freshmen @ Darien, 4 pm
September 18 @ 5:00 pm - 7:00 pm Varsity @ Greenwich, 5 pm; JV @ Greenwich, 5 pm; Freshmen vs Greenwich @ Wakeman E, 4 pm Greenwich High School 10 Hillside Road, Greenwich, CT, United States
September 21 @ 11:00 am - 1:00 pm Varsity @ Wilton, 11 am; JV @ Wilton, 9 am; Freshmen vs Wilton @ Wakeman E, 2 pm Wilton High School 395 Danbury Road, Wilton, CT, United States
September 23 @ 4:30 pm - 6:30 pm Varsity vs. Stamford @ Wakeman turf, 4:30 pm; Frosh @ Stamford, 4:30 pm
September 24 @ 4:00 pm - 6:00 pm Varsity @ Harding, 4 pm — POSTPONED Harding High School 1734 Central Ave., Bridgeport, CT, United States
October 1 @ 4:00 pm - 6:00 pm Varsity vs Fairfield Ludlowe @ Wakeman, 4 pm; JV vs. Ludlowe @ Wakeman E, 4 pm; Freshmen @ Fairfield Ludlowe, 4 pm
October 5 @ 12:00 pm - 2:00 pm Varsity @ Trumbull, 12 noon; JV @ Trumbull, 10 am; Freshmen vs Trumbull @ Wakeman E, 2 pm Trumbull High School 72 Strobel Road, Trumbull, CT, United States
