10 Wrestlers That Have Held The WWE Title The Most Times

9. The Undertaker (4)

The Undertaker held the title in 1991, 1997, 1999 and 2002; a pretty sporadic set of dates. Whilst The Deadman was a very capable and believable champion, the dimensions of his character allowed him far more intricate storylines that often didn€™t require the title. These included strapping Stephanie McMahon to a crucifix before trying to force her hand in marriage and wrapping a noose around the Big Boss Man€™s neck in order to hang him from a cage; yep, both of these events really did happen! Taker was fortunate enough to be one of very few guys to win the WWE Championship at WrestleMania; as we are all well aware, winning at the grandest stage of them all was an old hobby for the Phenom. Defending champion Sycho Sid became victim number six of what was once known as the streak; that still feels weird to say, doesn€™t it? With The Undertaker€™s loss to Brock Lesnar heavily indicating that we have perhaps seen the last of The Lord of Darkness as a performer; his achievements in the business can only be admired. He has produced twenty years of hellacious matches and will rightfully be placed into the WWE Hall of Fame in the coming years.