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#2 Chuck Liddell vs. UFC Hall of Famer Tito Ortiz - trilogy
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For years, Chuck Liddell and UFC Hall of Famer Tito Ortiz were involved in a heated rivalry. The former light heavyweight champions were two of the top fighters in MMA during their prime and the promotion's biggest draws.
Their bouts set pay-per-view records for the promotion and proved that MMA was on the rise in the combat sports landscape.
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They had a trilogy bout scheduled in 2011, which would have culminated in TUF season 11. But Ortiz sustained an injury and was replaced by former middleweight champion Rich Franklin.
Liddell looked great, however, 'Ace' caught him with 5-seconds left in the first-round and knocked him out. Perhaps the UFC could have attempted to book Liddell vs. Ortiz 3 in 2012 and promote it as 'The Iceman's final fight.
'The Iceman' won both their bouts inside the octagon. In 2004, he defeated 'The Huntington Beach Bad Boy' via knockout and then finished him via third-round TKO in 2006. Ortiz won their trilogy bout in 2018, but it's important to note that Liddell had been inactive for eight years at the time.
#1 Chuck Liddell vs. former UFC light heavyweight champion Frank Shamrock
Former UFC light heavyweight champion Frank Shamrock remains one of the biggest what-ifs in the promotion's history. The younger adoptive of Ken Shamrock represented the Lion's Den and was their most well-rounded fighter.
He was the inaugural UFC light heavyweight champion, but left the promotion in 1999 following a contract dispute. He successfully defended the title on four occasions, with his final being against Tito Ortiz, which earned Fight of the Year.
After defeating 'The Huntington Beach Bad Boy', Shamrock retired but returned to the sport in 2000 with another promotion. He never returned to the UFC, which left many possible matchups on the table.
If he had returned to the promotion in 2003, a bout with Chuck Liddell would have been intriguing. At the time, Shamrock had just won the WEC light heavyweight championship, while Liddell was riding a 10-fight winning streak.
Their fighting style would have made for an entertaining bout and it could have served as a title eliminator.
