#2 Tito Ortiz
UFC 13. That was the event, held on May 30, 1997, which introduced Tito Ortiz to MMA audiences.
Given the Huntington Beach Bad Boy's hugely successful Light-Heavyweight career in the UFC, one would expect that he would have won his tournament debut. However, that was not the case.
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UFC 13 saw Ortiz's first win but also his first loss in the company in which he would make his name.
That event saw Ortiz compete as an alternate in the Light-Heavyweight tournament wherein he defeated Wes Albritton via TKO. When Enson Inoue withdrew from the final due to injury, Ortiz stepped in to fight Guy Mezger in the final. However, the more experienced Mezger would beat Ortiz via a guillotine choke submission.
Ortiz never competed in another UFC tournament despite the later great fame he would achieve in the promotion.
He would avenge his loss to Mezger at UFC 19 before he went on to lift the Light-Heavyweight strap at UFC 25 by defeating Wanderlei Silva. Ortiz would reign for three and a half years before he was stunningly upset by former Heavyweight Champion, Randy Couture at UFC 44.