The 1999 UCF Golden Knights football season was Mike Kruczek's second year as the head coach of the Golden Knights. Kruczek led UCF to an overall record of 4–7 in 1999. During the season, the Golden Knights almost earned their first victory over a team from an automatic-qualifying BCS conference. UCF was defeated 23–24 by the Georgia Bulldogs in a game known as the "Burglary Between the Hedges." Later in the season, UCF was poised for another possible upset at Auburn, trailing 14-10 with three minutes left. However, the Tigers blasted for two touchdowns in the span of 94 seconds, dropping UCF by a final score of 28-10.
With the departure of Daunte Culpepper to the NFL Draft, the quarterback duties were taken over by college journeyman Vic Penn. The Golden Knights opened the season at the Citrus Bowl, hosting their largest-profile opponent thus far since joining Division I-A. Purdue, led by quarterback Drew Brees, soundly defeated UCF 49-13, and the Golden Knights started their season at 0-4. After two victories against Division I-AA opponents (Eastern Illinois and Nicholls State), UCF dropped their next game against Louisiana Tech. The Golden Knights finally got their first win of the season against a Div. I-A team with a 31-6 win over Eastern Michigan. The Knights secured a losing season with their stinging loss at Auburn on November 6.
During the decade of the 1990s, UCF would compile an overall record of 67–46–0 (.593) during the decade.