Fedor would have lit him up with superior striking.
It would have been really fun to see it go to the ground. Randy was a great wrestler and GNP master but Fedor had legendary submissions and escapes from the bottom.
Unfortunately though, Fedor would have likely hurt him bad in the first few exchanges on the feet. I don't even know if it would have gone to the ground. Even if it did, we have seen Fedor escape from being underneath bigger and better wrestlers like Randleman and Coleman. He also swept Nog.
He would have likely ran through Randy and i say this as a fan of both.
It still would have been a dream fight. It would be the ultimate clash of skills and they were about the same size.
I just don't think Randy can grind Fedor down in the clinch like he does to everyone else. Fedor will squirm away, create separation and hurt Randy with a straight right.
It would be awesome to see them in the clinch though for however long it would last. High level Greco vs High level Judo
I would actually rather see these guys grapple in a pure grappling contest.