September 24, 2019 @ 4:00 pm - 7:30 pm Varsity @ Trumbull, 5:30 pm; Reserves @ Trumbull, 4 pm; Frosh vs. Trumbull @ Wakeman E, 4 pm Trumbull High School 72 Strobel Road, Trumbull, CT, United States
September 26, 2019 @ 4:00 pm - 6:00 pm Varsity @ Fairfield Warde, 6:30 pm; Reserves training @ Wakeman E; Frosh vs Fairfield Warde @ Wakeman B, 4 pm Fairfield Warde High School 755 Melville Ave., Fairfield, United States
October 1, 2019 @ 4:00 pm - 6:00 pm Varsity vs. Greenwich @ Staples, 4 pm; Reserves vs Greenwich @ Wakeman E, 4 pm; Frosh vs. Greenwich @ Benvenuto Field, 4 pm Greenwich High School 10 Hillside Road, Greenwich, CT, United States
October 3, 2019 @ 4:00 pm - 7:30 pm Varsity @ Brien McMahon, 7 pm; Reserves @ Brien McMahon, 5 pm; Frosh vs. Brien McMahon, Wakeman E, 4 pm Brien McMahon High School 300 Highland Ave., Norwalk, CT, United States
October 5, 2019 @ 10:00 am - 6:00 pm Varsity vs Fairfield Ludlowe @ Staples, 2 pm (1969 state champs reunion); Reserves vs Fairfield Ludlowe @ Wakeman B, 2 pm; Frosh @ Fairfield Ludlowe, 10 am
October 12, 2019 @ 12:00 pm - 6:00 pm Varsity vs Stamford @ Staples, 12 pm; Reserves vs Stamford @ Wakeman B, 12 pm; Frosh @ Stamford, 9 am
October 15, 2019 @ 4:00 pm - 6:00 pm Varsity, reserves @ Ridgefield, 4 pm; Frosh @ Wakeman E Ridgefield High School 700 North Salem Rd., Ridgefield, CT, United States
October 17, 2019 @ 4:00 pm - 6:00 pm Varsity @ Darien, 4 pm; Reserves @ Darien, 4 pm; Frosh vs. Darien @ Wakeman E Darien High School 80 High School Lane, Darien, CT, United States
October 19, 2019 @ 12:00 pm - 4:00 pm Boys vs. St. Joseph @ Staples, 2 pm (Senior Day); Reserves vs St. Joseph @ Wakeman E, 2
October 22, 2019 @ 8:00 am - 5:00 pm Varsity @ Westhill, 4 pm; Reserves vs. Westhill @ Rippowam, 4 pm; Frosh vs. Westhill @ Wakeman B, 4 pm Westhill High School 125 Roxbury Road, Stamford, CT, United States
October 24, 2019 @ 4:00 pm - 6:00 pm Varsity @ New Canaan, 4 pm; Reserves vs New Canaan @ Saxe Middle School, 4 pm; Frosh vs New Canaan @ Wakeman E, 4 pm Conner Field 131 Farm Road, New Canaan, CT, United States
October 28, 2019 @ 8:00 am - 5:00 pm Varsity vs Wilton @ Wakeman B, 4 pm; Reserves and frosh games postponed
October 31, 2019 @ 2:00 pm - 8:00 pm Varsity: FCIAC quarterfinals vs. Danbury @ Mill Ridge School, 3:30 pm
