WWE Money in the Bank: 3 winners who cashed in on the same night 

#1. Dean Ambrose

Dean Ambrose cashed in on Seth Rollins back in 2016

Dean Ambrose was the last member of The Shield to become World Champion and what a way to do it. Money in the Bank 2016 will always be remembered as the night that all three members of The Shield were able to hold the World Championship since it was passed around in the main event.

Dean Ambrose won the annual contract ladder match before he waited until Seth Rollins was able to pin Roman Reigns and become World Champion for the first time since his return to the ring a month before. Ambrose then attacked Rollins with the briefcase before he cashed in and lifted his first World Championship.

Ambrose later went on to be drafted to SmackDown Live and became the brand's main Champion for a number of months before he lost his title to AJ Styles.