Ric Flair
John Cena recently surpassed Ric Flair’s legendary record of being a 16-time World Champion by capturing his 17th World Championship. Given this connection between two of wrestling’s most decorated champions, it’s shocking that they never faced each other one-on-one. Flair’s second WWE run spanned from 2001 to 2008, a time when Cena was on the rise.

The story of this match would’ve been very interesting and would have benefited Cena greatly. While Flair was past his prime during this run, he was still able to perform at a decent level, and Cena would have definitely carried him to a memorable encounter. The two wrestlers did team up a few times, and it is a shame it never resulted in a singles match.