The Pioneer Bowl was created in January 1997 to match teams from the CIAA and SIAC that did not qualify for the NCAA Division II National Football Championship playoffs.

[1] It was first contested that December, ending a period of eleven seasons (1986–1996) in which no Division II postseason game had carried the "bowl" designation.

The bowl only included champions of the CIAA or SIAC when those schools failed to meet the criteria for postseason playoff bids (a possibility in Division II, which has no automatic qualifiers).

The Pioneer Bowl thus served as Tuskegee's only postseason opportunity in several cases when it would have qualified for the Division II playoffs, most notably in 2000 and 2007, seasons in which the Golden Tigers finished a perfect 12–0.

The 2013 game was to be played on the home field of the CIAA representative but was cancelled on short notice "due to budgetary restraints.