They are held in December, and are most commonly scheduled on the first Saturday of the month, three weeks after the final games of the Division II football regular season.

In 1956 the NCAA College Division was created to serve the athletic needs of the association's smaller member institutions.

The division held separate championships in several sports, starting with a basketball tournament at the end of the 1956–57 season.

In lieu of a football championship, the division eventually held four regional bowl games from 1964 through 1972, intended to crown the small-college "champions" of different parts of the country.

The current system of Division II bowl games has its origins in 1997, when a new Pioneer Bowl (unrelated to the former game) was created as a contest between teams from the division's two conferences of historically black colleges and universities (HBCUs), the Southern Intercollegiate Athletic Conference (SIAC) and the Central Intercollegiate Athletic Association.

The bowl, held in Excelsior Springs, MO, dated from 1948 (with interruptions) and had been a junior college postseason contest from 1992 to 1999.

From 2013 through 2023, the Live United Texarkana Bowl featured a team from the Great American Conference (GAC), initially against an opponent from either the MIAA or the LSC.

[16] On November 4, 2024, the CIAA and SIAC revealed that the game would not be held in 2024, but did not address whether it would resume in future years.

Since the onset of the current Division II bowl system, Tuskegee has the most appearances (ten) and most victories (seven) of any team, all in the Pioneer Bowl, largely because its traditional Turkey Day Classic against Alabama State extended its regular season to Thanksgiving Day, precluding participation in the Division II playoffs.

On the conference level, teams from the MIAA have registered the greatest success, participating in the most bowls (5), the most games (37), and posting the most victories (27).

The conference's most impressive year was 2017, when MIAA teams played in each of the four bowls then in existence and won all four games.

The 2014 game, matching North Greenville against Shorter of the GSC, is the only one thus far to feature two Division II teams.