Freeport 6 Jamaica High School 13
Freeport 0 Commerce 12 (October 1, 1927)
Freeport 6 Lynbrook 19 (October 8, 1927)
Freeport 12 Glen Cove 0 (October 15, 1927)
Freeport 13 St. John's Prep 26 (October 22, 1927)
Freeport 0 Lawrence 7 (October 29, 1927)
Freeport 18 Port Washington (November 5, 1927)
Freeport 13 Baldwin 0 (November 8, 1927)
Freeport 23 Alumni 7 (November 13, 1927)
Freeport 0 Hempstead 0 (November 19, 1927)
Freeport tied with Lawrence for second place in the South Shore League. Freeport ranked number 1 in the number of players on the All-Nassau County high school football team. These players included: Hansen, Harmer, Cruickshank, and Eastman.
The team held its second annual football banquet at the Elks Club on December 5, 1927.
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