6 WWE Superstars with the most defeats in Money In The Bank ladder matches

#5 Shelton Benjamin (no wins, 5 defeats)

Shelton Benjamin produced plenty of high-risk moves in MITB matches

While Shelton Benjamin is best remembered by some fans for his initial impact in WWE as part of Team Angle, his legacy as a singles competitor is defined by his high-flying stunts in the Money In The Bank matches that he competed in.

Sadly for the former Intercontinental champion, he was never able to win the match, losing in five WrestleMania MITB ladder matches (2005, 2006, 2008, 2009 and 2010).

With both the Raw and SmackDown Live rosters more stacked than ever with young talent in 2018, it’d be a surprise to see Shelton involved in another MITB match during his WWE career.