The Bluegrass Bowl was a college football bowl game that was played only once, on December 13, 1958 in Louisville, Kentucky. The Oklahoma State Cowboys defeated Florida State Seminoles 15-6.

Game organizers expected the Bluegrass Bowl to be an annual event in Louisville, starting with the 1958 contest. The first choices for the game were the University of Kentucky and the University of Alabama, which went 5-4-1 in its first season under Bear Bryant, who had previously coached at UK for eight seasons. But the Wildcats (who had received poor treatment from the Louisville crowd during a 51-0 win over the University of Hawaii at Cardinal Stadium in their season opener) turned down the bid, with the team's lettermen voting 18-12 against. (Kentucky's players voting to turn down bowl bids was nothing new: they said no to the Gator Bowl in 1953, despite a 7-2-1 record in Bryant's final season in Lexington, and again in 1954 after going 7-3.) Alabama also declined; Oklahoma State University and Florida State University eventually accepted invitations.

Bowl organizers successfully negotiated a national television contract with ABC, with a 100-mile blackout. A crowd of 15,000 (less than half capacity) was expected for the inaugural game. Tickets were priced at $6.50 each, though due to unenthusiastic demand they were being sold for $1.50 on the day of the game. (Parking cost 25 cents.)

Oklahoma State entered the game ranked #19 in both the AP and UPI polls, while Florida State was unranked. Florida State was an independent with a 7-3 regular season record; Oklahoma State was also 7-3 as an independent, having left the Missouri Valley Conference after the 1956 season and not joining the Big Eight Conference until 1960. Florida State was playing in their third ever bowl game, under head coach Tom Nugent who was in his final season as Florida State's coach. Oklahoma State, coached by Cliff Speegle, was appearing in its fourth ever bowl game.

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