September 27 @ 4:00 pm - 6:00 pm Varsity vs Fairfield Warde @ Wakeman turf, 4 pm; JV vs Fairfield Warde @ Wakeman E, 4 pm; Freshmen @ Fairfield Warde, 4 pm
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
October 8 @ 4:00 pm - 6:00 pm Varsity @ Danbury, 6 pm; JV @ Danbury, 4 pm; Freshmen vs Danbury @ Wakeman E, 4 pm
October 10 @ 4:00 pm - 6:00 pm Varsity vs St. Joseph @ Wakeman, 4 pm; JV vs St. Joseph @ Wakeman E, 4 pm
October 16 @ 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 @ 4:00 pm - 6:00 pm Varsity @ Ridgefield, 4 pm; JV @ Ridgefield, 4 pm; Freshmen vs Ridgefield @ Wakeman E, 4 pm