Mankind/ Mick Foley
Mankind won the WWE title from the Rock on the January 4th 1999 Raw. He lost the title back on January 24th 1999 at Royal Rumble in an I Quit Match. He won the title back on the January 31st 1999 Halftime Heat Special in an Empty Arena Match. He lost the title back on the February 15th 1999 Raw in a Ladder Match. He won his third WWE title from Steve Austin in a triple threat match also involving Triple H with special referee Jesse Ventura on August 22nd 1999 at Summerslam. He lost the title to Triple H the next night on Raw in a match with Special referee Shane McMahon. Mick Foley won the TNA title from Sting at Lockdown on April 19th 2009. He lost the title to Kurt Angle on June 21st 2009 at Slammiversary in a King of The Mountain Match also involving Samoa Joe, Jeff Jarrett, and AJ Styles.
Randy Savage
Randy Savage won the vacant WWE title by defeating Ted DiBiase in a tournament final on March 27th 1988 at Wrestlemania. He lost the title to Hulk Hogan on April 2nd 1989 at Wrestlemania. He won his second WWE title from Ric Flair on April 5th 1992 at Wrestlemania. He lost the title back on the September 14th 1992 Prime Time Wrestling. He won the vacant WCW title by winning the World War 3 match on November 26th 1995 at World War 3. He lost the title to Ric Flair on December 27th 1995 at Starrcade. He won the title back on January 22nd 1996 on Nitro. He lost the title back on February 11th 1996 at SuperBrawl. He won his third WCW title from Sting on April 19th 1998 at Spring Stampede. He lost the title to Hollywood Hogan in a No DQ match on April 20th 1998 on Nitro. He won his fourth WCW title from Kevin Nash on July 11th 1999 at Bash at the Beach in a tag match also involving Sid Vicious and Sting. He lost the title to Hogan on July 12th 1999 on Nitro.
Mankind won the WWE title from the Rock on the January 4th 1999 Raw. He lost the title back on January 24th 1999 at Royal Rumble in an I Quit Match. He won the title back on the January 31st 1999 Halftime Heat Special in an Empty Arena Match. He lost the title back on the February 15th 1999 Raw in a Ladder Match. He won his third WWE title from Steve Austin in a triple threat match also involving Triple H with special referee Jesse Ventura on August 22nd 1999 at Summerslam. He lost the title to Triple H the next night on Raw in a match with Special referee Shane McMahon. Mick Foley won the TNA title from Sting at Lockdown on April 19th 2009. He lost the title to Kurt Angle on June 21st 2009 at Slammiversary in a King of The Mountain Match also involving Samoa Joe, Jeff Jarrett, and AJ Styles.
Randy Savage
Randy Savage won the vacant WWE title by defeating Ted DiBiase in a tournament final on March 27th 1988 at Wrestlemania. He lost the title to Hulk Hogan on April 2nd 1989 at Wrestlemania. He won his second WWE title from Ric Flair on April 5th 1992 at Wrestlemania. He lost the title back on the September 14th 1992 Prime Time Wrestling. He won the vacant WCW title by winning the World War 3 match on November 26th 1995 at World War 3. He lost the title to Ric Flair on December 27th 1995 at Starrcade. He won the title back on January 22nd 1996 on Nitro. He lost the title back on February 11th 1996 at SuperBrawl. He won his third WCW title from Sting on April 19th 1998 at Spring Stampede. He lost the title to Hollywood Hogan in a No DQ match on April 20th 1998 on Nitro. He won his fourth WCW title from Kevin Nash on July 11th 1999 at Bash at the Beach in a tag match also involving Sid Vicious and Sting. He lost the title to Hogan on July 12th 1999 on Nitro.