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. 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 47-13. UCF got out to an early 6-0 lead, but the Boilermakers scored 47 unanswered points, as Brees threw for 273 yards and four touchdowns. As the game got out of hand, two players were later ejected, and twice fans were arrested for running out on the field.
After being routed by #4 Florida, and #10 Georgia Tech, the Golden Knights almost earned their first victory over an SEC team. UCF was defeated 24–23 by #11 Georgia in a game known as the "Burglary Between the Hedges." The Golden Knights trailed by one point, and were driving inside the red zone in the final minute. At the 20 yard line with 15 seconds left, UCF was looking at a game-winning 37-yard field goal attempt, and a monumental upset. Coach Kruczek decided to run one more play before bringing kicker Javier Beorlegui out on the field. Quarterback Vic Penn lofted a pass to Kenny Clark in the endzone, but Clark was tackled out of bounds by Bulldogs defender Jeff Harris in what appeared to be blatant pass interference. The SEC officials, however, inexcusably called offensive pass interference on UCF. The Golden Knights were backed up 15 yards, and out of field goal range, and were robbed of a chance for victory.
After starting the season 0-4, the Golden Knights earned two victories against Division I-AA opponents (Eastern Illinois and Nicholls State). They finally got their first win of the season against a Division I-A team with a 31-6 win over Eastern Michigan on October 30.
On November 6, UCF was poised for another possible upset. After a near-miss against Auburn a year earlier, UCF once again took the Tigers down to the wire. Trailing 14-10 with three minutes left, the Tigers blasted for two touchdowns in the span of 94 seconds, dropping UCF by a final score of 28-10.
During the decade of the 1990s, UCF would compile an overall record of 67–46–0 (.593) during the decade.