August 29, 2014 @ 3:00 pm - 5:00 pm Varsity @ South Kent (scrimmage), 3 pm South Kent School 40 Bulls Bridge Rd., South Kent, United States
August 31, 2014 @ 1:00 pm - 5:00 pm Varsity vs. Martin Luther King HS @ Staples, 1 pm – Cookout to follow
September 3, 2014 @ 4:15 pm - 6:15 pm Varsity @ Choate, 4:15 pm (Scrimmage) Choate Rosemary Hall 333 Christian St. , Wallingford, CT, United States
September 6, 2014 @ 10:00 am - 3:00 pm Varsity @ Wethersfield Jamboree, 10 am-3 pm Wethersfield HS 411 Wolcott Hill Rd., Wethersfield, United States
September 9, 2014 @ 4:00 pm - 6:00 pm Varsity vs. St. Joseph @ Staples – 4 pm Staples High School 70 North Avenue, Westport, United States
September 16, 2014 @ 6:00 pm - 8:00 pm Varsity @ Danbury, 6 pm Danbury High School 43 Clapboard Ridge Rd., Danbury, United States
September 18, 2014 @ 4:00 pm - 6:00 pm Varsity vs. Bassick @ Staples, 4 pm Loeffler Field 70 North Avenue, Westport, CT, United States
September 22, 2014 @ 6:00 pm - 8:00 pm Boys varsity @ Ridgefield, 6 pm Ridgefield High School 700 North Salem Rd., Ridgefield, CT, United States
September 23, 2014 @ 7:15 pm - 9:15 pm Boys varsity @ Norwalk, 7:15 pm Norwalk High School 55 County St., Norwalk, CT, United States
September 30, 2014 @ 4:00 pm - 6:00 pm Varsity vs. New Canaan @ Staples, 4 pm Loeffler Field 70 North Avenue, Westport, CT, United States
October 2, 2014 @ 4:00 pm - 6:00 pm Varsity vs. Central @ Staples, 4 pm Central High School 1 Lincoln Blvd., Bridgeport, CT, United States
October 6, 2014 @ 4:00 pm - 6:00 pm Varsity vs. Westhill @ Staples, 4 pm Loeffler Field 70 North Avenue, Westport, CT, United States
October 8, 2014 @ 7:00 pm - 9:00 pm Varsity @ Brien McMahon, 4:45 pm Brien McMahon High School 300 Highland Ave., Norwalk, CT, United States
October 10, 2014 @ 3:45 pm - 5:45 pm Varsity @ Fairfield Ludlowe, 3:45 pm Fairfield Ludlowe High School 785 Unquowa Rd., Fairfield, United States