Triple H
Triple H won the WWE title from Mankind on August 23rd 1999 on Raw in a match with special referee Shane McMahon. He lost the title to Mr. McMahon on the September 16th 1999 Smackdown in a match with special referee Shane McMahon. He won the vacant title on September 26th 1999 at Unforgiven in a Six Pack Challenge also involving Rock, Mankind, Big Show, British Bulldog, and Kane. He lost the title to The Big Show in a triple threat match also involving The Rock on November 14th 1999 at Survivor Series. He won it back on the January 3rd 2000 Raw. He lost the title to The Rock on April 30th 2000 at Backlash. He won it back on May 21st 2000 at Judgment Day in a 60 minute Iron Man Match. He lost it back on June 25th 2000 at King of The Ring in a Six Man Tag match when Rock pinned Mr. McMahon. He won his fifth WWE title from Chris Jericho on March 17th 2002 at Wrestlemania. He lost the title to Hulk Hogan on April 21st 2002 at Backlash. He was awarded the World Title on the September 2nd 2002 Raw. He lost the title to Shawn Michaels on November 17th 2002 at Survivor Series in an Elimination Chamber match also involving Chris Jericho, Rob Van Dam, Kane, and Booker T. He won the title back on December 15th 2002 at Armageddon in a Three Stages of Hell Match. He lost the title to Goldberg on September 21st 2003 at Unforgiven. He won the title back in a triple threat match also involving Kane on December 14th 2003 at Armageddon. He lost the title to Chris Benoit in a triple threat match also involving Shawn Michaels on March 14th 2004 at Wrestlemania. He won his fourth World Title from Randy Orton on September 12th 2004 at Unforgiven. He vacated the title after a double fall in a match with Chris Benoit and Edge on the November 29th 2004 Raw. He won his fifth World Title on January 9th 2005 at New Year’s Revolution in an Elimination Chamber match also involving Chris Benoit, Chris Jericho, Randy Orton, Batista, and Edge. He lost the title to Batista on April 3rd 2005 at Wrestlemania. He won his sixth WWE title from Randy Orton on October 7th 2007 at No Mercy. He lost the title back the same night in a Last Man Standing Match. He won it back on April 27th 2008 at Backlash in a Fatal Four Way Match Elimination Match also involving John Cena and JBL. He lost it to Edge on November 23rd 2008 at Survivor Series in a triple threat match also involving Vladimir Kozlov. He won his eighth title from Edge in an Elimination Chamber match also involving Jeff Hardy, Vladimir Kozlov, Undertaker, and Big Show. He lost the title to Randy Orton in a six man tag team match on April 26th 2009 at Backlash.
Sid Vicious/ Sycho Sid
Sycho Sid won the WWE title from Shawn Michaels on November 17th 1996 at Survivor Series. He lost the title back on January 19th 1997 at Royal Rumble. He won his second WWE title on February 17th 1997 from Bret Hart on Raw. He lost the title to The Undertaker on March 23rd 1997 at Wrestlemania. As Sid Vicious, he won the vacant WCW title by defeating the Harris brothers and Kevin Nash on the January 24th 2000 Nitro. He was stripped of the title for pinning the wrong Harris Brother on the January 26th 2000 Thunder. He won the title back the same night by defeating Nash and Ron Harris in a handicap match. He vacated the title due to the WCW reboot on the April 10th 2000 Raw.
Triple H won the WWE title from Mankind on August 23rd 1999 on Raw in a match with special referee Shane McMahon. He lost the title to Mr. McMahon on the September 16th 1999 Smackdown in a match with special referee Shane McMahon. He won the vacant title on September 26th 1999 at Unforgiven in a Six Pack Challenge also involving Rock, Mankind, Big Show, British Bulldog, and Kane. He lost the title to The Big Show in a triple threat match also involving The Rock on November 14th 1999 at Survivor Series. He won it back on the January 3rd 2000 Raw. He lost the title to The Rock on April 30th 2000 at Backlash. He won it back on May 21st 2000 at Judgment Day in a 60 minute Iron Man Match. He lost it back on June 25th 2000 at King of The Ring in a Six Man Tag match when Rock pinned Mr. McMahon. He won his fifth WWE title from Chris Jericho on March 17th 2002 at Wrestlemania. He lost the title to Hulk Hogan on April 21st 2002 at Backlash. He was awarded the World Title on the September 2nd 2002 Raw. He lost the title to Shawn Michaels on November 17th 2002 at Survivor Series in an Elimination Chamber match also involving Chris Jericho, Rob Van Dam, Kane, and Booker T. He won the title back on December 15th 2002 at Armageddon in a Three Stages of Hell Match. He lost the title to Goldberg on September 21st 2003 at Unforgiven. He won the title back in a triple threat match also involving Kane on December 14th 2003 at Armageddon. He lost the title to Chris Benoit in a triple threat match also involving Shawn Michaels on March 14th 2004 at Wrestlemania. He won his fourth World Title from Randy Orton on September 12th 2004 at Unforgiven. He vacated the title after a double fall in a match with Chris Benoit and Edge on the November 29th 2004 Raw. He won his fifth World Title on January 9th 2005 at New Year’s Revolution in an Elimination Chamber match also involving Chris Benoit, Chris Jericho, Randy Orton, Batista, and Edge. He lost the title to Batista on April 3rd 2005 at Wrestlemania. He won his sixth WWE title from Randy Orton on October 7th 2007 at No Mercy. He lost the title back the same night in a Last Man Standing Match. He won it back on April 27th 2008 at Backlash in a Fatal Four Way Match Elimination Match also involving John Cena and JBL. He lost it to Edge on November 23rd 2008 at Survivor Series in a triple threat match also involving Vladimir Kozlov. He won his eighth title from Edge in an Elimination Chamber match also involving Jeff Hardy, Vladimir Kozlov, Undertaker, and Big Show. He lost the title to Randy Orton in a six man tag team match on April 26th 2009 at Backlash.
Sid Vicious/ Sycho Sid
Sycho Sid won the WWE title from Shawn Michaels on November 17th 1996 at Survivor Series. He lost the title back on January 19th 1997 at Royal Rumble. He won his second WWE title on February 17th 1997 from Bret Hart on Raw. He lost the title to The Undertaker on March 23rd 1997 at Wrestlemania. As Sid Vicious, he won the vacant WCW title by defeating the Harris brothers and Kevin Nash on the January 24th 2000 Nitro. He was stripped of the title for pinning the wrong Harris Brother on the January 26th 2000 Thunder. He won the title back the same night by defeating Nash and Ron Harris in a handicap match. He vacated the title due to the WCW reboot on the April 10th 2000 Raw.
