The 1958 Indians featured star hurlers Bob Sherman and Jack Silver, as well as CCBL Hall of Famer Jim Hubbard, an outfielder who went on to manage Cotuit to four consecutive Cape League titles in the 1960s. Yarmouth met perennial league powerhouse Orleans in the best-of-three Lower Cape title series. The teams split the first two games, with the Indians taking Game 1, 3–0, but dropping Game 2, 5–1. In Game 3, Yarmouth broke out the big bats against Orleans hurler and future major leaguer Art Quirk, the Lower Cape's Outstanding Pitcher of the season. The Indians piled up seven runs on Quirk, and Sherman made it stand up for a 7–5 series-clinching victory. The Indians moved on to face a powerful Sagamore team in the Cape League finals. In Game 1, the Indians shut down the Clouters' attack with a three-hit gem by Silver for a 2–1 victory. Sherman took the mound in Game 2, and the Indians came away with the 4–3 win to sweep the series and claim the team's first Cape League crown.