Over the course of two seasons, Gillispie compiled an overall record of 40 wins and 27 losses. In his first season (2007–08), the Wildcats finished with an 18–13 record and secured a spot in the NCAA Tournament, though they were eliminated in the first round.
The following season (2008–09), Kentucky finished with a 22–14 record. Despite the improved win total, the team failed to qualify for the NCAA Tournament—a significant disappointment for a program with Kentucky’s storied history. It was the first time since 1991 that the Wildcats had missed the tournament, and the setback intensified scrutiny of Gillispie’s leadership.
Compounding the on-court struggles were reported issues off the court, including tensions with players, staff, and university administrators. These challenges ultimately led to his dismissal in March 2009, just two years into his contract. During his time at Kentucky, the program did not win any major trophies or championships. Gillispie’s brief era is often remembered as a turbulent chapter in the history of Kentucky basketball.