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#2. Fedor vs. Alistair Overeem
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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.
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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.
#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.
