Wareham made a deep playoff run in 1957, beginning with a first round defeat of Otis Air Force Base, two games to one in the Upper Cape playoffs. In the series, Wareham rode the stellar pitching of Tom Eccleston, who threw a two-hit shutout in Game 2, and Bruce Reed, who gave up just five hits and helped himself with a homer in the decisive Game 3 victory. The win sent Wareham to the Upper Cape finals against the heavily-favored Cotuit Kettleers. Led by the hitting of brothers Bruce and Glenn Reed, Wareham routed Cotuit, 14–2, in Game 1 at Lowell Park, then with Bruce on the mound at home in Game 2, Wareham completed the sweep with a 3–0 shutout of the Kettleers. The win would be Wareham's only Upper Cape Division championship of the era. Wareham went on to face the Lower Cape champion Orleans Red Sox in the Cape League finals, but Orleans prevailed in two straight.