Chuck Liddell is undoubtedly one of the biggest stars in UFC history. He was a fan favorite throughout his MMA career with his fighting style and highlight-reel knockouts. He was one of the most popular fighters in the sport and achieved a great deal.
Liddell debuted in 1997 and made a name for himself in the light heavyweight division. It wasn't long before he fought the likes of Vitor Belfort, Kevin Randleman, and Randy Couture. In 2005, he reached the pinnacle of the sport when he knocked out Couture to become the light heavyweight champion.
'The Iceman' was a massive draw for the promotion and generated record pay-per-view buy-rates. This was significant at the time because MMA was still fairly new and the promotion was just reaching one million pay-per-view buys.
Despite the entertaining bouts Liddell was involved in, there were still many intriguing bouts that could've taken place. This list will look at five Chuck Liddell fights that could've but didn't happen in the UFC.
#5 Liddell vs. UFC Hall of Famer Stephan Bonnar
UFC Hall of Famer Stephan Bonnar was somebody who always brought it inside the octagon. He earned his place in MMA history through his time on the inaugural season of The Ultimate Fighter.
Although he didn't win TUF, his fight with Forrest Griffin has since been immortalized in the Hall of Fame. The fight was crucial to the promotion for gaining a broadcast deal with Spike TV in the United States. Despite being the underdog in the majority of his bouts, Bonnar was far from being an easy win.
'The American Psycho' vs. 'The Iceman' would have been a logical bout to book in 2009. Bonnar was riding a two-fight winning streak, while Liddell was coming off a devastating knockout loss to Rashad Evans.
They were no strangers to one another as 'The Iceman' coached on TUF season one opposite Randy Couture, who coached Bonnar. However, a battle between the two remained a pipedream.
#4 Chuck Liddell vs. former UFC light heavyweight champion Forrest Griffin
Forrest Griffin was an example of TUF producing UFC championship caliber fighters. He won the first season of TUF after defeating Stephan Bonnar via unanimous decision in an instant classic.
In 2008, he earned a unanimous decision against 'Rampage' Jackson and made history as the first TUF winner to become champion.
Griffin's reign was short-lived as he lost his title to TUF season 2 winner Rashad Evans in his first title defense. Following the loss, he was matched up with middleweight champion Anderson Silva, who accepted a light heavyweight bout to challenge himself.
It was a completely dominant performance for 'Spider' as he outclassed the former light heavyweight champion.
Rather than accepting the bout with Silva, the promotion could have matched Griffin up with Chuck Liddell. Both were coming off losses to Evans and it could have allowed both fighters to get back into title contention. The buildup to the fight would have been interesting as 'The Iceman' was Griffin's coach on TUF.
#3 Chuck Liddell vs. UFC Hall of Famer Dan Henderson
Despite never winning a UFC championship, Dan Henderson is still one of the most accomplished fighters to compete in the promotion. The Hall of Famer won championships in major promotions and in multiple weight divisions.
He is a former PRIDE middleweight and welterweight champion, and former Strikeforce light heavyweight champion.
'Hendo' split time between 205lbs and 185lbs when he returned to the promotion following their acquisition of PRIDE. If he had stayed at light heavyweight following his loss to 'Rampage' Jackson, a bout with Chuck Liddell would have been logical.
'The Iceman' was coming off a unanimous decision win against Wanderlei Silva, which was named Fight of the Year.
Despite being an Olympic wrestler, Henderson was also known for his knockout power. Based on their fighting styles, 'Hendo' vs. 'The Iceman' wouldn't have been a tough sell for the promotion.
Henderson would find the perfect moment to strike his opponents with his 'H-bomb' right-hook, while Liddell had incredible power. If the bout took place in 2008, it could have realistically served as a title eliminator bout.
#2 Chuck Liddell vs. UFC Hall of Famer Tito Ortiz - trilogy
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.
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.