September 16, 2024 @ 4:00 pm - 6:00 pm Varsity vs Darien @ Wakeman, 4 pm; JV vs Darien @ Wakeman #, 4 pm; Freshmen @ Darien, 4 pm
September 18, 2024 @ 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, 2024 @ 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, 2024 @ 4:30 pm - 6:30 pm Varsity vs. Stamford @ Wakeman turf, 4:30 pm; Frosh @ Stamford, 4:30 pm
September 24, 2024 @ 4:00 pm - 6:00 pm Varsity @ Harding, 4 pm — POSTPONED Harding High School 1734 Central Ave., Bridgeport, CT, United States
September 25, 2024 @ 4:00 pm - 6:00 pm Varsity vs Central @ Wakeman, 4 pm; JV vs Central @ Wakeman E, 4 pm
October 1, 2024 @ 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, 2024 @ 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
October 8, 2024 @ 4:00 pm - 6:00 pm Varsity @ Danbury, 6 pm; JV @ Danbury, 4 pm; Freshmen vs Danbury @ Wakeman E, 4 pm Danbury High School 43 Clapboard Ridge Rd., Danbury, CT, United States
October 10, 2024 @ 4:00 pm - 6:00 pm Varsity vs St. Joseph @ Wakeman, 4 pm; JV vs St. Joseph @ Wakeman E, 4 pm
October 16, 2024 @ 4:30 pm - 6:30 pm Varsity vs Westhill @ Wakeman, 4:30 pm; JV vs Westhill @ Wakeman E, 4:30 pm; Freshmen vs Westhill @ Rippowam Middle School, 4 pm
October 18, 2024 @ 4:00 pm - 6:00 pm Varsity @ Ridgefield, 4 pm; JV @ Ridgefield, 4 pm; Freshmen vs Ridgefield @ Wakeman E, 4 pm Ridgefield High School 700 North Salem Rd., Ridgefield, CT, United States
