As many senior organizations began to form in the 1920's, the first West Penn Senior Amateur was played in 1929. The first forty-five competitions were held at Oakmont Country Club. Two players dominated in its first two decades with five wins each - George T. Gregg and Joe Wells: both are the top winners to this day. Eight-time WPGA Senior Player of the Year, Paul Schlachter, has won the Senior Amateur five times. Next with three are Phil Saylor, Arnold Horelick, and Knox Young who was a top player in the 50's and 60's. Bob Kiersky won the 1965 title and later that fall he won the USGA Senior Amateur at Fox Chapel Golf Club.

The 18-hole competition was changed to 36-holes in 2000. The 18-hole and 36-hole records were set in 2005 by Paul Schlachter with 69-68--137 at the Pittsburgh Field Club.

The Senior Amateur is open to players age 55 and older, and the Super-Senior Amateur is available to players 65 and older.