Ranking the Most Dangerous Spots in WWE Money in the Bank Ladder Match History

Money in the Bank has become one of WWE’s longest-running annual traditions. 

Since its inception in 2005, the match has been held every year. That means the only stipulation match in company history that has a longer annual run is the Royal Rumble. Other famous stipulation matches, such as the traditional Survivor Series and Elimination Chamber, were all ended (and in some cases, later restarted) before they reached a streak as long as Money in the Bank’s. 

While the eventual Money in the Bank winners have often provided memorable cash-in moments, more often than not winning the world championship, let’s look back on some of the best spots from the ladder matches themselves, ranked based on how dangerous and memorable they were.

10. Shelton Benjamin's Running Clothesline (2005)

We’re going to run it back to the very first Money In the Bank match for our first entry; a match that was held at WrestleMania 21 in Los Angeles. The roster for this bout was absolutely stacked: Edge, Chris Jericho, Christian, Kane, Chris Benoit and Shelton Benjamin. 

Benjamin was coming off a stellar 2004, his first full year in WWE as a singles performer. He had victories over Triple H and Ric Flair and defeated Chris Jericho to win the Intercontinental Championship. So heading into WrestleMania, he was a name on the rise who fans thought had a real chance to walk out victorious.

Though Benjamin did not win the match, he turned a lot of heads with one of the most memorable spots of the night: running up a diagonal ladder, to a standing ladder, to clothesline Chris Jericho to the floor.

9. Superplexing Ric Flair (2006)

While Flair taking a superplex off a ladder might seem miniscule compared to some of the other dangerous moments on this list, context makes this one all the more impressive.

Flair took part in the second-ever Money in the Bank match at WrestleMania 22, joining Rob Van Dam, Bobby Lashley, Finlay, Matt Hardy and Shelton Benjamin in the bout. However, Flair’s participation was particularly memorable due to the fact that he was 57 years old at the time. 

Even during his prime, Flair wasn’t known for high spots. Sure, he took press slams off the top rope here and there, but that was about it. He certainly wasn’t the type of wrestler who you’d see flying off of ladders throughout his decades-long career. 

So when Flair took a superplex from Matt Hardy off a ladder in his late 50s, it turned a lot of heads.

8. Sheamus Obliterates Sin Cara (2011)

Sheamus has participated in the Money in the Bank match on four occasions, even winning the briefcase once (2015).

2011 was the first year that Sheamus participated in the bout, and he had one of his overall most memorable spots during that inaugural outing. With a large ladder set up between the ring apron and the announce position, Sheamus picked up Sin Cara and powerbombed him off the ring apron and through the ladder on the outside. 

Daniel Bryan went on to win the match, but the powerbomb by Sheamus to Sin Cara had the crowd in Chicago's Allstate Arena buzzing.

7. Shelton Benjamin Does It Again (2008)

Credit: WWE

There’s no question that over the course of the first several Money in the Bank matches, Benjamin was the wrestler who often stood out. Sure, he may not have won, but he was always doing wild things. And he competed in five of the first six incarnations of the match. 

WrestleMania 24 saw the fourth edition of Money in the Bank, and it was Benjamin’s third time as a competitor in the match. In terms of dangerous moments, the fans in Orlando that night saw Benjamin outdo anything he had done in any of his prior appearances in the bout. 

Benjamin ascended the ladder inside of the ring, only to have it pushed over by two of his competitors (Carlito and Mr. Kennedy). Benjamin flipped midair and went crashing through a ladder on the outside that was set up between the ring and ringside barrier.

Side note: Another great Benjamin moment from Money in the Bank that's not on this list is his Swanton off the ladder at WrestleMania 25 in 2009.

6. Andrade Powerbombs Finn Balor into Next Week (2019)

Andrade and Finn Balor are two wrestlers tailor-made for the Money in the Bank match. Great in-ring technicians that can also fly and excel doing high spots.

The 2019 Money in the Bank match was ultimately won by Brock Lesnar, not exactly your typical ladder match extraordinaire. So WWE loaded up the match with people like Balor, Andrade, Mustafa Ali and Ricochet to carry the weight when it came to flying around the ring.

Balor and Andrade certainly did their part. Andrade scaled the ladder and leapt over Balor, who was perched on the other side of the ladder, executing a sunset flip powerbomb that sent Balor into another ladder—and then up into the air from the impact.

This is a wild spot that you need to see to believe.

5. Seth Rollins Takes a Brutal Backdrop (2014)

Seth Rollins’ route to the top of WWE started in the summer of 2014. He began the month of June by turning on The Shield and joining The Authority, and just a couple of weeks later at Money in the Bank, he captured the briefcase that would set in motion his first world championship win at WrestleMania 31 the following spring. 

Winning the Money in the Bank match to win that briefcase came with a price via one of the most eye-popping moves of the night. Rollins and Kofi Kingston battled on one of the ladders inside the ring, with Seth just inches from capturing the briefcase and winning the match.

However, Kingston was able to back-body-drop Rollins over the ladder and onto another ladder set up between the ladder and the top rope below them. Rollins bounced off the ladder and down to the mat in what was an absolutely brutal-looking fall.

4. Iyo Sky's Tombstone to Zoey Stark (2024)

WWE/Getty Images

The 2024 women’s Money in the Bank match was absolutely wild, and this is the first of two dangerous moves from that match on our list.

The current WWE Women’s World Champion, Iyo Sky, really showed out in last year’s match, taking some brutal bumps (including a Fisherman’s Suplex on a ladder from Lyra Valkyria) while also dealing out some punishment of her own.

Late in the bout, Sky climbed the ladder in the middle of the ring and battled with Zoey Stark. Sky ended up picking her up and nailing a Tombstone piledriver on to a ladder that was wedged between the ring ropes and the base of the ladder, sending the crowd in Toronto into a frenzy. 

While Tiffany Stratton went on to win the match, Sky stood out to fans in a memorable way. Sky's popularity with the fans would continue to accelerate, ultimately helping carry her to the world title in early 2025.

3. Kevin Owens Powerbombed Through a Ladder (2021)

The 2021 edition of Money in the Bank was WWE’s first full-capacity show following the height of the COVID-19 pandemic. Fans packed the Dickies Arena in Forth Worth, Texas, for a star-studded men’s Money in the Bank match that featured Kevin Owens, Seth Rollins, Big E, Drew McIntyre, Ricochet, Shinsuke Nakamura, Matt Riddle and John Morrison. 

Big E went on to capture the briefcase on that night, and he also had a great move when he delivered the Big Ending to Rollins off a ladder. But Owens and Rollins topped that with perhaps the most memorable bump of the night. Rollins used his running “buckle bomb” powerbomb during the match, but this time it wasn’t into the corner turnbuckle. He had his sights set on a ladder outside of the ring.

The victim? Owens. The move? Absolutely ridiculous. Owens went flying over the top rope and crashed through the ladder on the outside of the ring.

2. Chelsea Green's Insane Table Bump (2024)

WWE/Getty Images

Chelsea Green experienced a breakout year in 2024, catapulting herself into the women’s title picture and winning over WWE fans with a character that was, and remains, thoroughly entertaining.

As an entrant in the 2024 edition of the women’s Money in the Bank, Green seemed like a real possibility to win the briefcase, but she was ultimately taken out by the other rising star in the match—Tiffany Stratton. 

As both women ascended side-by-side ladders late in the match, Stratton was able to push over Green’s—sending her flying over the top rope and crashing through two tables on the outside. 

Stratton then grabbed the briefcase, winning the match (and ultimately, the WWE Women's Championship in January 2025). But Green cemented her place in the minds of WWE fans in one of the most memorable Money in the Bank match spots of all time.

1. Jeff Hardy Destroys Edge With a Leg Drop Through a Ladder (2007)

WrestleMania 23 saw the third incarnation of the men’s Money in the Bank match, and with Jeff Hardy in contention that year, it was no surprise that things got a little wild.

During the match at Ford Field, Edge was set up laying across a ladder on the outside of the ring with the help of Jeff's brother, Matt. Then, Jeff climbed a ladder inside the ring and jumped, crashing through Edge and the ladder on the outside using a leg drop.

Predictably, the move took Edge and Hardy out of the match for the remainder of the night. But it was a heck of a moment and one that will go down as one of the most brutal, dangerous moves in WWE's Money in the Bank match history.