Pittaro played his first professional season with the Macon Peaches of the Class-A South Atlantic League in 1982.

Pittaro moved to second base when he played for the Lakeland Tigers of the Class-A Florida State League in 1983.

[7] Though he expected to begin the season with the Nashville Sounds of the Class-AAA American Association, Pittaro made the Tigers out of spring training,[8] serving in a platoon with Tom Brookens.

[13] Before the 1986 season, the Tigers traded Pittaro with Alejandro Sánchez to the Minnesota Twins for Dave Engle.

[14] He played with the Twins, batting .095 in a backup role before he was demoted to the Toledo Mud Hens of the Class-AAA International League.

[15] Pittaro and split the 1987 season with the Twins and their new Class-AAA affiliate, the Portland Beavers of the Pacific Coast League.

[8] After his playing career, Pittaro graduated summa cum laude with a Bachelor of Science in finance from Rider.