The rivalry between these two schools, located about 180 miles (290 km) apart, dates to their first college football game in 1893, and has continued across all sports, with the men's basketball series gaining particular attention.

The football game was previously played for a wooden Bourbon Barrel trophy, which was discontinued in 1999.

The location of the game alternated between Assembly Hall in Bloomington and Rupp Arena in Lexington.

A scheduling conflict with Louisville's Freedom Hall in 2006 forced the series back to the schools' respective campuses.

ESPN commentator Dick Vitale said of the rivalry, "Don't you get excited in the world of basketball thinking about Kentucky and Indiana playing?

Notable storylines of the rivalry also involve major upsets by both teams and high-profile, outspoken coaches, including Bob Knight and Adolph Rupp.

Indiana coach Bob Knight would frequently suggest that Kentucky violated NCAA recruiting rules.

"[5] The somber Indiana fans [IU had lost the season opener to Butler] who made up about half the crowd of 38,197 at the dome the next day seemed to agree with that assessment.

They sat quietly as the Kentucky faithful jeered the Hoosiers during warmups, waving an array of signs: CBS (CATS BY SIXTY)...INDIANA WHOSTERS...WHICH WAY TO BUTLER?

[21] A last-second shot which propelled Indiana to victory over top-ranked Kentucky and another meeting in the 2012 NCAA Tournament (won by Kentucky) helped re-kindle the rivalry's intensity; however, Calipari and Indiana head coach Tom Crean were unable to resolve the issue of whether to play future games on the respective teams' home courts or at neutral sites.

[22] After IU athletic director Fred Glass reopened negotiations on May 10, 2012, Calipari rejected Glass's compromise to play two games at Lucas Oil Stadium and one game apiece at Assembly Hall and Rupp Arena, thus ending the series.

The Indiana-Kentucky women's basketball series was played annually on a home-and-home basis from the 1976–77 to 1990–91 seasons, except for the December 30, 1990 game played in Reno, Nevada for the New Year's Classic tournament hosted by the University of Nevada, Reno,[28][29] and again from 1993–94 to 1997–98.

[28] The series then went on a nine-year pause until the championship round of the Women's Sports Foundation Tournament on November 12, 2006, a 54–51 Indiana win over No.

[28][30] After a 14-year hiatus, the series resumed when Kentucky announced on November 19, 2020, nearly a week before the delayed start of the 2020–21 season, the addition of a December 5 home game vs.