1. Randy Couture vs. Fedor Emelianenko
For years Fedor Emelianenko was the exception to the rule that all the best fighters were in the UFC, and it put an asterisks next to the promotion’s heavyweight division.
The main issue between the UFC and Fedor was always the issue of co-promotion. Fedor wanted to be free to have his business interests in the M-1 promotion, of which he is part owner. Fedor would fight for Pride, Strikeforce and Affliction during his prime years, but never the UFC. Couture on the other hand, spent all but 4 of his fights in the UFC despite trying on numerous occasions to get out of his contract with them.
The rumours of the two camps trying to arrange a fight, despite Couture’s contracted status with the UFC, was most prominent between 2006 and 2008, when Couture was the UFC heavyweight champion and Fedor was the consensus #1 heavyweight in the world.
Fedor will turn 40 in the fall but is still fighting, though he did retire between 2012-2015. He even appeared on UFC Fight Pass while fighting at EFN 50, leading to more speculation that he might still end up fighting in the UFC some day.
He’ll never fight Couture however, that window has closed. Scott Coker did manage to get both of them to pose together in a staredown ahead of a Bellator event however. Sadly that is the closest will ever get.
