The team finished with a record of 95–59, seven games in front of the second-place Milwaukee Braves to win their first National League championship in 33 seasons.
The team went on to play the heavily favored New York Yankees, whom they defeated 4 games to 3 in one of the most storied World Series ever.
At the 1959 Winter Meetings, Pirates general manager Joe L. Brown had agreed to trade Dick Groat to the Kansas City Athletics in exchange for Roger Maris.
Pirates manager Danny Murtaugh had advised Brown that he did not want to lose Groat, and the deal was never finalized.
On September 6, team captain Dick Groat was drilled on his left wrist by an inside pitch from Braves pitcher Lew Burdette.