#5 vs. Jon Jones
If he were to sign with the UFC, barring a fight with Brock Lesnar, perhaps the biggest match that Fedor could possibly make would not be with one of the UFC’s current Heavyweights, but instead with the reigning UFC Light-Heavyweight champion Jon Jones. It wouldn’t be like Jones would be giving up a lot of size, after all – he’s a huge 205lber who’s spoken about moving up, and Fedor is a small Heavyweight who could easily make 205lbs himself.
The intrigue surrounding this fight would be simply huge – could the ageing Russian legend pull off what would probably be the most remarkable victory of his entire career, over a man who’s realistically never been beaten? Or would he become another victim of ‘Bones’, another legend to add to his list of conquered heroes like Shogun Rua, Rampage Jackson and Vitor Belfort?
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Naturally, in 2019 you’d have to give Jones a huge advantage over the ageing Russian as Fedor is miles past his prime now, but hey, the UFC managed to make Matt Hughes vs. Royce Gracie sell in 2006, and Royce was far more out of his prime then than Fedor is now. This fight would probably draw millions on pay-per-view for the UFC, and that alone would make it worth it.