5. Phil Baroni
(Largest UFC Losing Streak)
The owner of the longest losing streak in UFC history belongs to Phil Baroni, with 6. Had Tito Ortiz not pulled off a crazy upset victory over Ryan Bader, he would be the owner of this maligned record.
Baroni managed to win 2 of his first 3 UFC fights, but it was all down hill from there.
His losing streak actually spanned 2 stints with the organization however. From 2003 to 2005, Baroni lost to Matt Lindland, Evan Tanner 2x, and Pete Sell. He then returned to the UFC in 2009 at UFC 109 and lost to Amir Sadollah. He got one last chance at UFC 111, but Baroni lost yet again, this time to Brad Tavares.