The history of the Crosstown Shootout dates back to 1928, when the University of Cincinnati helped St. Xavier College dedicate its brand new, $350,000 Schmidt Fieldhouse, which had a capacity of 4,500.

[1] ESPN's Jay Bilas was quoted as saying, "Cincinnati and Xavier have created a rivalry that is unparalleled when it comes to outright passion and civic division.

The game is also regularly attended by local legends and sports icons Pete Rose and basketball great and former Bearcat Oscar Robertson.

[5] On June 14, 2012, both schools held a joint press conference at the National Underground Railroad Freedom Center announcing that the annual rivalry will now be called "Skyline Chili Crosstown Classic.

The first game of the resumed series was held on February 18, 2015, during ESPN's Rivalry Week when Xavier hosted Cincinnati on December 12, 2015, at the Cintas Center.

[11] February 27, 1946: Despite two prior meetings, this matchup marked the "official" start to the annualized series that would take the city by storm.

With an eleven-point lead and 2:06 remaining, the Bearcats gave up nine points to Xavier, but time prevented the upset and Cincinnati won 61–58.

[14] March 3, 1967: The 1966 overtime contest—the last of 12 straight Cincinnati wins—resulted in 57 fouls and saw Musketeer Joe Pangrazio grab a crutch from a fan in the stands so he could throw it at Bearcat Raleigh Wynn.

During the game Cincinnati player Myron Hughes punched Xavier's Eddie Johnson, knocking him to the ground.

[17] January 19, 1994: After a hard-fought 82–76 overtime win for Xavier, Cincinnati head coach Bob Huggins refused to shake his XU counterpart Pete Gillen's hand post-game and instead verbally confronted him, causing much controversy.

November 26, 1996: The Cincinnati Bearcats were ranked #1 in the country and were largely considered frontrunners for the national championship by several media outlets, including Sports Illustrated.

[14] February 3, 2004: Xavier came into the game a huge underdog against #10 Cincinnati, but pulled off the upset over the Bearcats 71–69 at the Cintas Center.