The Undertaker (May 23, 1999 - June 28, 1999)
Stone Cold's third reign as WWE Champion did not last long. After defeating The Rock at WrestleMania XV and Backlash 1999, he dropped the strap to The Undertaker at Over The Edge 1999.
With help from the McMahon's, The Undertaker lifted the strap for a third time. Like Stone Cold, 'Taker's reign would also be short lived.
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The Undertaker was suffering from a multitude of injuries, most notably his groin which inhibited his in ring performances. He, therefore was not a suitable choice for champion, even on a short term basis.
The Phenom would successfully defend the strap versus The Rock in an entertaining, albeit protracted contest at the 1999 King of the Ring event. However, his reign would last just one more day as he was pitted against Stone Cold once more on Raw.
That is where his title run would end as Austin would stunner his way to a fourth World crown and 'Taker would slide down the card until he departed WWE in September.
He would be sidelined until May 2000, after suffering a pectoral injury as he returned from his groin surgery on a December house show.