Undertaker
The Undertaker won the WWE title from Hulk Hogan on November 27th 1991 at Survivor Series. He lost the title back on December 3rd 1991 at This Tuesday in Texas. He won his second WWE title from Sycho Sid on March 23rd 1997 at Wrestlemania. He lost the title to Bret Hart on August 3rd 1997 at Summerslam in a match featuring Shawn Michaels as referee. He won his third WWE title from Steve Austin on May 23rd 1999 at Over the Edge with The McMahons as referees. He lost the title back to Austin on June 28th 1999 on Raw. He won his fourth WWE title from Hulk Hogan on May 19th 2002 at Judgment Day. He lost the title to The Rock in a triple threat match also involving Kurt Angle on July 21st 2002 at Vengeance. He won the World title from Batista on April 1st 2007 at Wrestlemania. He lost the title to Edge on the May 11th 2007 Smackdown. He won the title back on March 30th 2008 at Wrestlemania. He vacated the title due to his Hell’s Gate finisher being banned on the May 2nd 2008 Smackdown. He won his third world title from CM Punk on October 4th 2009 at Hell in a Cell in a Hell in a Cell Match. He lost the title to Chris Jericho on February 21st 2010 at Elimination Chamber in an Elimination Chamber match also involving John Morrison, R-Truth, CM Punk, and Rey Mysterio.
Bob Backlund
Bob Backlund won the WWE title from Superstar Billy Graham on February 20th 1978 in New York, NY. He lost the title to The Iron Sheik on December 26th 1983 in New York, NY. He won the WWE title for a second time from Bret Hart on November 23rd 1994 in a Submission Match at Survivor Series. He lost the title to Diesel the next night in New York, NY.
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The Undertaker won the WWE title from Hulk Hogan on November 27th 1991 at Survivor Series. He lost the title back on December 3rd 1991 at This Tuesday in Texas. He won his second WWE title from Sycho Sid on March 23rd 1997 at Wrestlemania. He lost the title to Bret Hart on August 3rd 1997 at Summerslam in a match featuring Shawn Michaels as referee. He won his third WWE title from Steve Austin on May 23rd 1999 at Over the Edge with The McMahons as referees. He lost the title back to Austin on June 28th 1999 on Raw. He won his fourth WWE title from Hulk Hogan on May 19th 2002 at Judgment Day. He lost the title to The Rock in a triple threat match also involving Kurt Angle on July 21st 2002 at Vengeance. He won the World title from Batista on April 1st 2007 at Wrestlemania. He lost the title to Edge on the May 11th 2007 Smackdown. He won the title back on March 30th 2008 at Wrestlemania. He vacated the title due to his Hell’s Gate finisher being banned on the May 2nd 2008 Smackdown. He won his third world title from CM Punk on October 4th 2009 at Hell in a Cell in a Hell in a Cell Match. He lost the title to Chris Jericho on February 21st 2010 at Elimination Chamber in an Elimination Chamber match also involving John Morrison, R-Truth, CM Punk, and Rey Mysterio.
Bob Backlund
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Bob Backlund won the WWE title from Superstar Billy Graham on February 20th 1978 in New York, NY. He lost the title to The Iron Sheik on December 26th 1983 in New York, NY. He won the WWE title for a second time from Bret Hart on November 23rd 1994 in a Submission Match at Survivor Series. He lost the title to Diesel the next night in New York, NY.