Pittinger was a hard-luck pitcher who played for two of the worst teams in the National League at the turn of the 20th century.

In 1901, Pittinger joined the Boston Beaneaters rotation that included Vic Willis, Bill Dinneen and Kid Nichols.

The next season, he collected 27 wins, tying with teammate Willis for the second place in the National League behind Jack Chesbro (29).

Before the 1905 season, Pittinger was sent by Boston to the Philadelphia Phillies in the same trade that brought Chick Fraser and Harry Wolverton to the Beaneaters.

Pittinger finished with 23 wins, second to New York Giants star Christy Mathewson (31) for the NL lead.