The Chairman secured his world record for being the oldest person to win the World Wrestling Entertainment Championship on September 14, 1999, when he was 54 years and 21 days old. Not too shabby.
Vince McMahon took on his future son-in-law, Triple H for what was then the WWF Championship, winning thanks to a little help from Stone Cold Steve Austin. Being the guy that he is, McMahon vacated the title during the next episode of Raw.