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WWE's annual Money in the Bank pay-per-view is rapidly approaching.
This has led to the WWE Universe already predicting who they think will leave Money in the Bank this year with the men's and women's Money in the Bank contracts.
However, sometimes winning the Money in the Bank briefcase is just half of the battle. The real challenge is keeping the Money in the Bank contract.
Throughout WWE history there have been numerous examples of WWE Superstars defending their Money in the Bank contract in regular matches.
In stark contrast to the danger and recklessness of the ladder matches used to win the Money in the Bank contract, a regular match in which a WWE Superstar must defend their Money in the Bank briefcase poses several different types of challenges.
Let's take a closer look at five times the WWE Money in the Bank contract was defended in a regular match.
#5 Chris Jericho vs Dolph Ziggler - Career vs. Contract match (WWE RAW - August 20, 2012)
Dolph Ziggler achieved one of the most famous Money in the Bank cash-ins in WWE history when he won the WWE World Heavyweight Championship on Monday Night RAW in 2013.
However, it could have been very different for Ziggler if certain matches hadn't gone his way in 2012. The former Intercontinental Champion defended his Money in the Bank contract on several occasions during his time holding the briefcase.
One such instance was on the August 20, 2012 edition of Monday Night RAW. Dolph Ziggler was engaged in a lengthy feud with former WWE World Heavyweight Champion Chris Jericho during the summer of 2012 on WWE television.
Ziggler claimed that Y2J had "lost his touch" and wasn't the wrestler he once was. This led to a match at SummerSlam in which Chris Jericho defeated Dolph Ziggler in the opening match of the show.
The following night on RAW a re-match between Ziggler and Jericho was set. Except this time, the stakes had been raised. Dolph Ziggler was forced to place his Money in the Bank contract on the line, whereas Chris Jericho was forced to put his WWE contract on the line in a career vs contract match.
After a long, physical encounter, Dolph Ziggler was able to defeat Chris Jericho, retaining his Money in the Bank briefcase and therefore terminating Jericho's contract with WWE.
#4 Braun Strowman vs Kevin Owens (WWE SummerSlam 2018)
Former WWE Superstar Braun Strowman won the Money in the Bank ladder match at the 2018 Money in the Bank pay-per-view event.
After securing the briefcase, The Monster Among Men went on to feud with former Universal Champion Kevin Owens on Monday Night RAW. This led to a Steel Cage match at the Extreme Rules pay-per-view event.
The closing moments of the Steel Cage match saw Braun Strowman chokeslam Kevin Owens off the top of the cage through an announce table at ringside. As Owens was the first to hit the floor, the former Universal Champion technically won the match despite enduring an unbelievable amount of physical trauma.
Owens' victory set up a match between himself and Braun Strowman at SummerSlam later that year. This time, it was announced that Braun Strowman's Money in the Bank contract would be on the line during his WWE SummerSlam match against Kevin Owens.
But, the match didn't go well for KO at all. With the Money in the Bank contract on the line, Braun Strowman decimated Kevin Owens in just under two minutes. The closing moments of the match saw Braun Strowman chokeslam Kevin Owens onto the entrance ramp.
This was followed by a running powerslam by Strowman to Owens, allowing Strowman to retain his WWE Money in the Bank contract.
#3 Rob Van Dam vs Shelton Benjamin - Championship vs. Contract match (WWE Backlash 2006)
WWE Hall of Famer Rob Van Dam had arguably the best year of his WWE career in 2006.
After returning from injury during the Royal Rumble match in January, RVD went on to compete in the Money in the Bank ladder match at WrestleMania 22. The former ECW star was successful in retrieving the briefcase, winning the match and becoming Mr. Money in the Bank.
Following his Money in the Bank victory at WrestleMania 22, RVD entered a feud with Intercontinental Champion Shelton Benjamin on Monday Night RAW. Rob Van Dam and Shelton Benjamin challenged each other to matches for Van Dam's Money in the Bank contract and Benjamin's Intercontinental Championship respectively.
Eventually it was decided that Benjamin and Rob Van Dam would meet at Backlash with both the Intercontinental Championship and the Money in the Bank contract on the line.
At the event, both WWE Superstars delivered an excellent championship vs contract encounter. The closing moments of the match saw Rob Van Dam hit a Five Star Frog Splash onto Shelton Benjamin, winning the match, retaining the Money in the Bank contract and capturing the Intercontinental Championship.
#2 Otis vs The Miz (WWE Hell in a Cell 2020)
WWE SmackDown Superstar Otis was riding high after he surprisingly won the men's Money in the Bank ladder match at the 2020 WWE Money in the Bank pay-per-view.
The former Heavy Machinery member outlasted the likes of AJ Styles, Rey Mysterio, King Corbin, Daniel Bryan and Aleister Black to win the cinematic "corporate" Money in the Bank ladder match emanating from WWE's headquarters in Stanford, Connecticut.
In the autumn of 2020, Heavy Machinery began feuding with The Miz and John Morrison on Friday Night SmackDown. The rivalry began when Miz and Morrison stole Otis' Money in the Bank briefcase.
After the hijinx involving the Money in the Bank contract being situated inside Otis' lunchbox, The Miz and John Morrison eventually sued Otis for the briefcase. Despite being told to relinquish the contract, Otis and The Miz battled it out in a "wrestlers' court" with John 'Bradshaw' Layfield serving as the judge.
JBL ruled that a match at the Hell in a Cell pay-per-view would determine the holder of the Money in the Bank briefcase, with Otis defending against The Miz.
The closing moments of the match saw Tucker shockingly turn on his tag team partner and strike Otis with the Money in the Bank briefcase. This allowed The Miz to capitalize and pin Otis, winning the Money in the Bank briefcase for the second time in his career.
#1 Edge vs Mr. Kennedy (WWE Monday Night RAW - 7th May 2007)
Former WWE Superstar Mr. Kennedy was once destined for greatest in WWE.
There were numerous storylines designed to make Kennedy a top star in the company throughout his WWE career. This included being revealed as Mr. McMahon's illegitimate son and also winning the Money in the Bank contract.
Mr. Kennedy won the Money in the Bank ladder match at WrestleMania 23 by defeating Edge, Finlay, Jeff Hardy, Matt Hardy, King Booker, Randy Orton and CM Punk.
After winning the briefcase, Kennedy announced on a subsequent episode of Monday Night RAW that he intended to cash in his Money in the Bank contract opportunity at WrestleMania XXIV eleven months later. However, this did not happen.
During this time, WWE World Heavyweight Champion The Undertaker was injured on Friday Night SmackDown. The plan was to have Mr. Kennedy shockingly appear on SmackDown, cash in the Money in the Bank contract, become the World Heavyweight Champion and write The Undertaker off WWE television.
However, during a RAW live event the week prior, Mr. Kennedy suffered a suspected torn triceps. Still needing for The Undertaker to drop the World Heavyweight Championship on SmackDown, the decision was made for Kennedy to lose the Money in the Bank contract.
So, on the May 7, 2007 edition of Monday Night RAW, Mr. Kennedy was challenged by Edge to defend his Money in the Bank briefcase, to which Kennedy accepted.
But before the match could even begin, Edge struck Mr. Kennedy with a monitor. This allowed Edge to spear Kennedy and win the Money in the Bank contract. The Rated R Superstar would cash the contract in the next night at the SmackDown television tapings and become the World Heavyweight Champion.
The initial prognosis of Mr. Kennedy's injury suggested that he had torn the triceps completely off the bone and would be out of action for five to seven months.
However, it was later discovered that the injury wasn't as severe as first thought. The triceps tendon had not torn off the bone, but in fact was instead a massive hematoma.
Kennedy returned to in-ring action only a few weeks later with no Money in the Bank briefcase and no World Heavyweight Championship.
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