10 WWE Superstars Who Won By Losing

2. "Macho King" Randy Savage (WrestleMania VII)

Savage Warrior Retirement Match
WWE.com

WrestleMania VII featured the culmination of the greatest story ever told by WWE.

After reaching the peak of success in 1988, by winning the WWF Championship at WrestleMania IV, Randy Savage and Miss Elizabeth split, engineering a couple of tumultuous years ahead in storylines. Savage joined with the Malificent-esque Sensational Sherri and, as the "Macho King", challenged the Ultimate Warrior to a Career Ending Match at WrestleMania VII. Elizabeth remained out of the spotlight.

At WrestleMania VII, fans experienced an emotional roller coaster that saw Savage exhaust everything he had, including five Flying Elbows, before succumbing to Warrior. Despite the epic 20 minute match, the story was only half-over.

Afterwards, Sherri attacked Randy, leading to a spectating Elizabeth to rush the ring and toss Sherri to the outside. In the aftermath of all the chaos, fans were treated to the long-awaited reunion of the Macho Man and his paramour.

For the second time at WrestleMania, Savage stole the show in defeat. Although he lost at WrestleMania VII, at WrestleMania VIII Savage regained the WWF title with Elizabeth by his side.

Contributor
Contributor

A former stuntman for Paramount Pictures, Matt enjoys sports, water skiing, driving fast, the beach, professional wrestling, technology, and scotch. At the same time, whenever possible. Having attended many famous (and infamous) shows including WrestleMania XV, In Your House: Mind Games, and the 1995 King of the Ring, Matt has been a lifelong professional sports and wrestling fan. Matt's been mentioned in numerous wrestling podcasts including the Steve Austin Show: Unleashed, Talk Is Jericho, and Something To Wrestle With Bruce Prichard. As a former countywide performer, Matt has been referred to as Mr. 300 for his amazing accomplishments in the world of amateur bowling. He is also the only man on record to have pitched back-to-back no hitters in the Veterans Stadium Wiffle Ball League of 2003.