Tuskegee University made the most appearances at the Pioneer Bowl, with a total of 10. Tuskegee also won the most Pioneer Bowls, with seven wins. Until 2012, Tuskegee's regular season extended longer than most other Division II teams (its last regular season game was the Turkey Day Classic on Thanksgiving Day), which prevented the team from playing in the NCAA's Division II playoff tournament; the Pioneer Bowl was thus the only way Tuskegee could play in the postseason.
The Pioneer Bowl was originally an NCAA playoff game in its College Division, held in Wichita Falls, Texas. It began as one of the four season-ending national quarterfinals in 1971 and 1972; there were no semifinals or finals and the national champion was determined by poll from the four quarterfinal winners. It succeeded the Pecan Bowl, which was played in Abilene (1964–67) and Arlington (1968–70). The other three regional finals were the Boardwalk, Grantland Rice, and Camellia bowls.
With the launch of Division II in 1973 and its full playoff system, the Pioneer Bowl was one of the two Division II semifinals (with the Grantland Rice Bowl) for the first three years, and then became the championship game for two years. For the inaugural season of Division I-AA in 1978, the Pioneer Bowl became the new division's title game. The I-AA title game was played in Florida in 1979 and California in 1980, then returned to Wichita Falls as the Pioneer Bowl in 1981 and 1982.