Kentucky opened with a 51–0 win over Hawaii at Cardinal Stadium in Louisville. A 13–0 win in the SEC opener against Georgia Tech followed. 2–0 Kentucky, then ranked #17 in the AP poll, then lost four games in a row: 27–6 to #9 Ole Miss in Memphis, 8–0 to #1 Auburn, 32–7 at #9 LSU and 28–0 at Georgia. A 33–12 win over Mississippi State was followed by a 0–0 tie against Vanderbilt. After a 20–6 win against Xavier, Kentucky closed the season with a 6–2 victory at Tennessee.
The victory over Tennessee was Kentucky's second in a row, and second in a stretch of four games in which Kentucky denied Tennessee a win. The Wildcats were invited to participate in the 1958 Bluegrass Bowl but declined due to what they considered to be poor treatment during their season opener, a win against Hawaii in the stadium in which the Bluegrass Bowl would be played. Florida State and Oklahoma State played in the 1958 Bluegrass Bowl instead.