5 Fedor Emelianenko fights that never happened

Throughout his legendary career, Fedor Emelianenko has defeated some of the biggest names in the sport. Despite never competing in the UFC, ‘The Last Emperor’ is regarded by many as the greatest heavyweight of all-time.

In his prime, Fedor earned a reputation for being a knockout artist and quickly defeated former champions. He fought the majority of career in PRIDE, where he became PRIDE heavyweight champion after defeating Antonio Rodrigo Nogueira. For years, many wondered how Fedor would’ve fared in the UFC, especially during his prime.

‘The Last Emperor’ fought and defeated many former UFC heavyweight champions including Andrei Arlovski and Tim Sylvia. But there were still interesting bouts that could’ve taken place had he joined the UFC. This list will look at 5 Fedor Emelianenko fights that never happened.

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#5. Fedor vs. Anderson Silva

UFC 208: Silva vs. Brunson

Kicking off this list of Fedor Emelianenko fights that never happened is against former UFC middleweight champion Anderson ‘The Spider’ Silva.

Throughout his career, Silva had some of the most spectacular finishes that are still being talked about today. ‘The Spider’ is widely regarded as one of the greatest pound-for-pound fighters of all-time for his accomplishments in the sport. He successfully defended his championship nine-times, while also taking a few light heavyweight fights in between.

In 2015, Chael Sonnen mentioned a rumor that a Fedor vs. Silva bout was in the works at 205lbs. Although ‘The Last Emperor’ was a heavyweight, he was never a massive heavyweight and competing at 205lbs wasn’t so far-fetched.

It would’ve been interesting to see how Fedor vs. Silva would have gone. ‘The Last Emperor’ has one-punch knockout power, but Silva would get in his opponents’ heads and have them second-guessing themselves.

#4. Fedor vs. Josh Barnett

UFC Fight Night: Barnett v Nelson

Fedor vs. Josh Barnett was a huge fight that never happened. The two were originally scheduled to fight back in 2009 at Affliction 3. However, the bout didn’t come to fruition due to Barnett failing a drug test, resulting in the clash being cancelled.

‘The Warmaster’ had a lot of success utilizing his catch wrestling on route to a UFC heavyweight championship. After his UFC departure, he carried his success over to PRIDE. Barnett was runner-up in the 2006 PRIDE heavyweight Grand Prix after losing to Mirko Cro Cop in the finals.

Even when both fighters were competing in Strikeforce at the same time, the bout never materialized. The only opportunity for ‘The Last Emperor’ vs. ‘The Warmaster’ was in the Strikeforce heavyweight Grand Prix in 2011. But, Fedor was defeated by ‘Bigfoot’ Silva, while Barnett, on the other side of the bracket, advanced to the finals.

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#3. Fedor vs. Randy Couture

One of the biggest Fedor Emelianenko fights that never happened was against Randy ‘The Natural’ Couture. In 2007, Couture did the unthinkable by defeating then-UFC heavyweight champion Tim Sylvia to become the new champion. ‘The Natural’ was 44 years old at the time and defeated the much larger and younger champion.

Couture then followed that up by successfully defending his title against top-contender Gabriel Gonzaga. After these impressive performances, there was plenty of discussion of Couture and Fedor fighting one another. The bout would’ve taken place in Affliction, but those plans were scrapped after failed negotiations with the UFC.

‘The Natural’ had great wrestling and was a handful to deal with in the clinch. Even in his 40s, Couture was still competing at a very high level. Fedor vs. Couture would be another what-if as ‘The Natural’ lost the UFC heavyweight championship to Brock Lesnar at UFC 91.

#2. Fedor vs. Alistair Overeem

It's hard to believe that a fight between Fedor Emelianenko and Alistair Overeem never took place. The bout not taking place while both competed in the same promotion remains one of the biggest missed opportunities in MMA.

Strikeforce had multiple opportunities to book Fedor vs. Overeem. In fact, the fight should have been ‘The Last Emperor’s' Strikeforce debut in 2010. ‘The Reem’ was the reigning Strikeforce heavyweight champion at the time and Affliction, where Fedor was competing, had folded. Instead, Brett Rogers ended up challenging Overeem for the title and then fought Fedor in his Strikeforce debut.

Strikeforce had another opportunity to book the fight in their heavyweight Grand Prix. It seemed like Fedor vs. Overeem would be inevitable in the second round. But, ‘The Last Emperor’ was defeated by ‘Bigfoot’ Silva in the opening round. 'The Demolition Man', on the other hand, was replaced by eventual tournament winner Daniel Cormier in the second-round.

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#1. Fedor vs. Brock Lesnar

Topping this list of Fedor Emelianenko fights that never happened is against Brock Lesnar. A bout between ‘The Last Emperor’ and ‘The Beast Incarnate’ would have been the biggest fight in UFC history. In 2009, UFC President Dana White met with Emelianenko and his management to negotiate bringing him into the promotion. To top it off, his UFC debut would have been against UFC heavyweight champion Lesnar.

Fedro Emelianenko ended up declining the UFC’s offer. The UFC president claimed the deal would have paid 'The Last Emperor' a significant amount of money. Dana White also stated in interviews that the fight would’ve taken place at AT&T Stadium in Dallas, Texas, which seats over 100,000. White was obviously not too thrilled when Fedor signed with Strikeforce as he felt it was the best deal possible.

A fight between the two heavyweights would have been a wonderful sight to see, especially in a large stadium. Lesnar’s size, speed and strength made him a difficult fighter to deal with, while Fedor still had devastating knockout power.