10 Longest Gaps Between WWE Superstars' WrestleMania Matches

When Ric Flair took his Big Gold Belt and headed up north in 1991, it seemed obvious that 'The Nature Boy' would make his WrestleMania debut in a main event dream match against Hulk Hogan. The biggest stars of their respective companies in the 1980s, battling it out for the WWF Championship. Of course, this did not happen. Although we got a bloody and engaging Flair vs. Randy Savage match out of it, we also got a mistimed and deflating Hogan vs. Sid Justice main event, so our enjoyment was most certainly not doubled. Flair was already back in WCW by WrestleMania IX, after being informed by Vince McMahon that he was too old to be featured prominently in top-line feuds with main-eventers.

In an only-in-wrestling turn of events, an obviously even older Ric Flair was back at WrestleMania ten years later, being featured prominently in a top-line feud with a main eventer. Flair rolled back the years at WrestleMania X8 in a losing effort to The Undertaker, who had personally requested that 'The Nature Boy' be the next victim of his Streak, suggesting that Vince had been premature in his judgement of Flair's ability a decade earlier.