#3 - Kane - 11 losses

Kane made his WrestleMania debut against the Undertaker at WrestleMania 14 but he failed to end the Phenom's undefeated streak at WrestleMania. However, he won 3 matches at WrestleMania in the next 3 years to improve his win-loss record.
In his 5th WrestleMania match, he lost to Kurt Angle before he once again lost to his brother the Undertaker at WrestleMania 20. He lost the Money in the Bank ladder match the next year before losing to the Great Khali at WrestleMania 23. Kane then failed to win the next 2 Money in the Bank matches he participated in and then he emerged as a loser in all the Andre the Giant memorial battle royales he took part in.
He is currently working on a light schedule as he seldom makes WWE appearances nowadays.