Edge
Edge won the WWE title from John Cena on January 8th 2006 at New Year’s Revolution. He lost the title back on January 29th 2006 at Royal Rumble. He won the title for a second time from Rob Van Dam on July 3rd 2006 on Raw in a triple threat match also involving John Cena. He lost the title to Cena on September 17th at Unforgiven in a TLC Match. He won the World Title from The Undertaker on the May 11th 2007 Smackdown. He vacated the title due to injury on the July 20th 2007 Smackdown. He won his second World Title from Batista on December 16th 2007 at Armageddon in a Triple Threat Match also involving the Undertaker. He lost the title to The Undertaker on March 30th 2008 at Wrestlemania. He won the vacant World Title on June 1st 2008 at One Night Stand by defeating the Undertaker in a TLC Match. He lost the title to CM Punk on June 30th 2008 on Raw. He won his third WWE title from Triple H on November 23rd 2008 at Survivor Series in a triple threat match also involving Vladimir Kozlov. He lost the title to Jeff Hardy on December 14th 2008 at Armageddon. He won the title back on January 25th 2009 at Royal Rumble in a NO DQ match. He lost the title to Triple H on February 15th 2009 at No Way Out in an Elimination Chamber match also involving Jeff Hardy, Vladimir Kozlov, The Undertaker and The Big Show. He won his fourth World Title from John Cena on February 15th 2009 at No Way Out in an Elimination Chamber match also involving Chris Jericho, Rey Mysterio, Mike Knox, and Kane. He lost the title to John Cena in a triple threat match also involving Big Show on April 5th 2009 at Wrestlemania. He won the title back in a Last Man Standing Match on April 26th 2009 at Backlash. He lost the title to Jegg Hardy in a Ladder Match on June 7th 2009 at Extreme Rules. He won his sixth World Title from Kane in a Four Way TLC Match also involving Rey Mysterio and Alberto Del Rio at TLC on December 19th 2010. He was stripped of the Title for using the Spear on the February 18th 2011 Smackdown. He won the title back from newly crowned champion Dolph Ziggler that same night. He vacated the title due to retirement on The April 12th 2011 Smackdown.
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.
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Edge won the WWE title from John Cena on January 8th 2006 at New Year’s Revolution. He lost the title back on January 29th 2006 at Royal Rumble. He won the title for a second time from Rob Van Dam on July 3rd 2006 on Raw in a triple threat match also involving John Cena. He lost the title to Cena on September 17th at Unforgiven in a TLC Match. He won the World Title from The Undertaker on the May 11th 2007 Smackdown. He vacated the title due to injury on the July 20th 2007 Smackdown. He won his second World Title from Batista on December 16th 2007 at Armageddon in a Triple Threat Match also involving the Undertaker. He lost the title to The Undertaker on March 30th 2008 at Wrestlemania. He won the vacant World Title on June 1st 2008 at One Night Stand by defeating the Undertaker in a TLC Match. He lost the title to CM Punk on June 30th 2008 on Raw. He won his third WWE title from Triple H on November 23rd 2008 at Survivor Series in a triple threat match also involving Vladimir Kozlov. He lost the title to Jeff Hardy on December 14th 2008 at Armageddon. He won the title back on January 25th 2009 at Royal Rumble in a NO DQ match. He lost the title to Triple H on February 15th 2009 at No Way Out in an Elimination Chamber match also involving Jeff Hardy, Vladimir Kozlov, The Undertaker and The Big Show. He won his fourth World Title from John Cena on February 15th 2009 at No Way Out in an Elimination Chamber match also involving Chris Jericho, Rey Mysterio, Mike Knox, and Kane. He lost the title to John Cena in a triple threat match also involving Big Show on April 5th 2009 at Wrestlemania. He won the title back in a Last Man Standing Match on April 26th 2009 at Backlash. He lost the title to Jegg Hardy in a Ladder Match on June 7th 2009 at Extreme Rules. He won his sixth World Title from Kane in a Four Way TLC Match also involving Rey Mysterio and Alberto Del Rio at TLC on December 19th 2010. He was stripped of the Title for using the Spear on the February 18th 2011 Smackdown. He won the title back from newly crowned champion Dolph Ziggler that same night. He vacated the title due to retirement on The April 12th 2011 Smackdown.
Undertaker
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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.