Rutgers Cup Winner
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Freeport 28 Mont Pleasant 12 (September 20, 1958)
Freeport 14 Lawrence 6 (September 27, 1958)
Freeport 4 Levittown 14 (October 11, 1958)
Freeport 31 Brooklyn Tech 20 (October 18, 1958)
Freeport 6 Hempstead 0 (October 25, 1958)
Freeport 20 Hicksville 13 (November 1, 1958)
Freeport 41 Massapequa 0 (November 8, 1958)
Freeport 33 Baldwin 6 (November 15, 1958)
Jerry Jackson, halfback, was All-Scholastic and Nassau-Suffolk All-Star.
The Freeport-Hempstead game was the first to be telecast on TV.
Bill Ashley was "Coach of the Year" in the Long Island Press and recognized as an outstanding coach in Newsweek.
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