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.
Chris Jericho
Chris Jericho won the WCW title from The Rock on October 21st 2001 at No Mercy. He lost the title back on The November 5th 2001 Raw. He won the title back on December 9th 2001 at Vengeance. He won the WWE title from Steve Austin on December 9th 2001 at Vengeance. He unified the two titles that night. He lost the title to Triple H on March 17th 2002 at Wrestlemania. Chris Jericho won the vacant WWE title on September 7th 2008 in a Scramble match also involving JBL, Batista, Rey Mysterio, and Kane at Unforgiven. He lost the title to Batista on October 26th 2008 at Cyber Sunday. He won the title back on November 3rd 2008 on Raw. He lost the title to John Cena on November 23rd 2008 at Survivor Series. He won his third world title on February 21st 2010 from The Undertaker at Elimination Chamber in an Elimination Chamber match also involving John Morrison, R-Truth, CM Punk, and Rey Mysterio. He lost the title to Jack Swagger on the April 2nd 2010 Smackdown.
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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.
Chris Jericho
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Chris Jericho won the WCW title from The Rock on October 21st 2001 at No Mercy. He lost the title back on The November 5th 2001 Raw. He won the title back on December 9th 2001 at Vengeance. He won the WWE title from Steve Austin on December 9th 2001 at Vengeance. He unified the two titles that night. He lost the title to Triple H on March 17th 2002 at Wrestlemania. Chris Jericho won the vacant WWE title on September 7th 2008 in a Scramble match also involving JBL, Batista, Rey Mysterio, and Kane at Unforgiven. He lost the title to Batista on October 26th 2008 at Cyber Sunday. He won the title back on November 3rd 2008 on Raw. He lost the title to John Cena on November 23rd 2008 at Survivor Series. He won his third world title on February 21st 2010 from The Undertaker at Elimination Chamber in an Elimination Chamber match also involving John Morrison, R-Truth, CM Punk, and Rey Mysterio. He lost the title to Jack Swagger on the April 2nd 2010 Smackdown.