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#2 The Big Show (five wins and 12 losses at WrestleMania)
The Big Show is one of the most intimidating athletes to ever step foot in a WWE WrestleMania ring. His large stature and incredible strength made sure that whoever beat him on a big stage would get a huge rub. This led to WWE booking him in a string of WrestleMania matches in which he suffered embarrassing losses. It came to a point where Cody Rhodes made fun of him for the same on the road to WrestleMania 28.
The Big Show's first WrestleMania in 1999 gave him his first loss at the event. It was a DQ loss against WWE legend Mankind. The Big Show didn't win a WrestleMania match until 2006 where he teamed up with Kane to successfully defend the World tag team titles against Carlito and Chris Masters. He lost to the likes of John Cena, Akebono, and The Undertaker during this time period.
Boxing legend Floyd Mayweather Jr. handed an embarrassing loss to The Big Show at WrestleMania 24. The Big Show lost another match a year later when John Cena defeated him and Edge to win the World title. He came very close to winning the very first Andre The Giant Memorial Battle Royale at WrestleMania 30 before being thrown out by Cesaro.
