15 Money In The Bank Matches WWE Fans Will Never Forget

Ladder matches have become a staple of professional wrestling, specifically WWE, with numerous of them becoming the stuff of legend over the years. Shawn Michaels vs. Razor Ramon at WrestleMania 10, the Undertaker vs. Jeff Hardy on "Raw," and more have elevated ladder matches to the next level. Although, no discussion of ladder match history is complete without touching on one of the most famous variations on the match type out there: the Money in the Bank ladder match, which has been a widely-adored part of WWE's creative arsenal since 2005.

The rules of the Money in the Bank ladder match are quite simple. All one has to do is scale a ladder and unhook the briefcase hanging above the ring. This earns the winner a world championship match, anytime, anywhere, within the next calendar year. The only dilemma — aside from choosing when to cash-in once one retrieves the briefcase — is overcoming the multiple other competitors involved in the match who are equally determined to take the Money in the Bank contract for themselves. These matches are generally thrilling, shocking, and overall highly entertaining.

Still, just because you toss a bunch of ladders and skilled athletes in the ring with a title shot on the line doesn't guarantee a memorable match. Not all Money in the Bank matches are created equally, with some proving far more noteworthy than the rest. These 15 in particular proved especially unforgettable, and here's why.

After becoming a staple of WrestleMania the previous five years, Money in the Bank underwent a major change in 2010. For the first time, the match took place on its own designated pay-per-view, aptly titled Money in the Bank. Additionally, fans in attendance and watching at home were treated to two Money in the Bank matches in one night — a trend that would continue for a few years. On the "SmackDown" side of things, Kane, Christian, Big Show, Cody Rhodes, Drew McIntyre, Kofi Kingston, Dolph Ziggler, and Matt Hardy all put their bodies on the line for a shot at the World Heavyweight Championship.

All in all, this match had all the bells and whistles of your typical Money in the Bank match: high spots off of ladders, nasty bumps onto ladders, false finishes, and all the fun stuff. However, where it deviated from the norm was with its winner: Kane. In prior MITB matches, younger, smaller competitors found success, not huge, established ones like "The Devil's Favorite Demon." Nevertheless, he held the blue briefcase high in the end, and less than an hour later, he successfully cashed-in the contract on World Heavyweight Champion Rey Mysterio — the first person to cash-in the same night they won MITB and, as of this writing, the quickest turnaround time ever.

Kane shocked the world at Money in the Bank 2010, making history in more ways than one. Therefore, this "SmackDown" ladder match isn't likely to disappear from the history books or the fans' collective memory any time soon.

Months before Kane would hoist the blue Money in the Bank briefcase high above his head, the final WrestleMania Money in the Bank ladder match took place. WrestleMania XXVI, emanating from Glendale, Arizona's University of Phoenix Stadium, saw Christian, Drew McIntyre, Dolph Ziggler, Evan Bourne, Kofi Kingston, Matt Hardy, Kane, Montel Vontavious Porter — aka MVP — Shelton Benjamin, and Jack Swagger do battle for a WWE or World Heavyweight Championship opportunity. Suffice to say, all of the wrestlers involved went to great lengths to etch their names in the history books.

As far as Money in the Bank ladder matches go, this one was decent at best, though it had its moments. Shelton Benjamin, Matt Hardy, Kofi Kingston, and Evan Bourne in particular did some entertaining things with the stipulation, but it was all in vain. When it was all said and done, "The All-American American" Jack Swagger won Money in the Bank and stood at the top of the ladder, all smiles, with the MITB briefcase in hand. A mere few years into his WWE run, Swagger had torn through the "ECW" roster, winning the ECW Championship once, but did he really have what it took to become WWE or World Heavyweight Champion?

Swagger cashed-in his contract on the following "SmackDown" to become the new World Heavyweight Champion and embark on a rather uneventful reign that lasted 82 days. If nothing else, this Money in the Bank match is unforgettable because of the poor choice of winner and the lackluster title run that his win created.

The year 2020 threw just about everyone for a loop, as the COVID-19 pandemic sent the world into disarray. Folks were stuck at home, masks became normal out-of-the-house attire, and it became more fashionable than it already should've been to wash your hands. Meanwhile in the WWE, the show went on — minus fans and any semblance of normalcy, although this presented a fun opportunity for Money in the Bank 2020 to offer viewers cinematic renditions of the iconic match type. This year, both the men's and women's MITB matches required competitors to reach the top of WWE Global HQ to secure the briefcase. 

Both matches occurred simultaneously, though each group went after their respective briefcase. As for the men, the field consisted of Daniel Bryan, Rey Mysterio, AJ Styles, Aleister Black, King Corbin, and Otis — a bunch of genuine potential winners and a comedic star who'd gained in popularity as of late. Despite the cartoonish nature of his character, Otis surprisingly managed to make it to the top of WWE HQ and win the Money in the Bank briefcase. However, he never got to cash it in seeing as the Miz defeated Otis for the briefcase at Hell in a Cell in October 2020.

In no time flat, Otis' momentum soon took a nosedive as he disappeared from the main event scene. For that reason, and the stipulation of having to reach the top of a building instead of just climbing a ladder, the men's Money in the Bank ladder match from 2020 is a hard one to forget. 

The 2012 edition of Money in the Bank took place at the US Airways Center in Phoenix, Arizona, bringing with it two exciting namesake ladder matches. The first, contested between Christian, Damien Sandow, Dolph Ziggler, Cody Rhodes, Santino Marella, Tyson Kidd, Sin Cara, and Tensai, saw Ziggler earn a World Heavyweight Championship match opportunity at the time of his choosing. The second featured a far thinner field of competitors: Chris Jericho, John Cena, Big Show, Kane, and The Miz, with a WWE Championship match hanging in the balance.

Miz, Jericho, Big Show, and Kane all came into the match with prior MITB experience, in some cases having won prior matches. On the other hand, John Cena had never taken part in such a match, but given his status as the face of the company, the odds were good that he'd walk away with the red briefcase. Sure enough, he did so, announcing his cash-in a few days later on "Raw" and challenging WWE Champion CM Punk to a match at "Raw 1000." The two put on a good match, only for Big Show to interfere and attack Cena, ending the match in a disqualification and preventing Cena from winning the title.

Even though he's among the biggest names in wrestling, John Cena will go down in history as the first man to fail at cashing-in a Money in the Bank contract. On the bright side, he has a 100% success rate in MITB matches since the 2012 installment is the only one he's competed in, so at least he can hang one of his many colorful hats on that.

After years of Money in the Bank being a men-only match type, WWE took a big step forward in 2017. For the first time in history, the company hosted a women's Money in the Bank ladder match at that year's event. With the brand split back in effect, Money in the Bank was a "SmackDown"-exclusive event that year, meaning a SmackDown Women's Championship opportunity was on the line. Charlotte Flair, Becky Lynch, Tamina, Carmella, and Natalya took part in the historic bout, which the wrestling world couldn't help but talk about by the time the final bell rang.

For the most part, Lynch, Natalya, Flair, Carmella, and Tamina put on a decent show. If nothing else, they proved that it was long overdue for fans to get an all-female MITB match. Well, it was almost all-female, considering that Carmella's lackey James Ellsworth climbed the ladder and retrieved the briefcase for her. Given this controversial ending, "SmackDown Live" authority figure Daniel Bryan vacated the Money in the Bank briefcase and set up a rematch for it on a future installment of "SmackDown." Once again, thanks to Ellsworth's intervention, Carmella asserted herself as the first-ever Ms. Money in the Bank.

Carmella eventually cashed-in successfully to become the new SmackDown Women's Champion, but her title win is far from the reason why her Money in the Bank win is so memorable. Only in WWE would fans see the first women's Money in the Bank ladder match end thanks to the intervention of a man.

On the same evening that Kane stood tall as the winner of the "SmackDown" Money in the Bank ladder match, a handful of members of the "Raw" roster took part in a ladder match of their own. Chris Jericho, the Miz, Ted DiBiase Jr., John Morrison, Mark Henry, Edge, Evan Bourne, and Randy Orton all walked into Money in the Bank 2010 with their eyes on an opportunity at the WWE Championship, but only one of them could take the red briefcase home. The Miz managed to secure the Money in the Bank contract, drastically altering the course of his career from then onward.

The Miz burst onto the WWE scene proper (not counting his time on "Tough Enough") in 2006, and for a few years, he didn't get a lot to do. He notably found success with Morrison as a tag team, but he didn't really prove himself as a solo act until 2009 into 2010. His hard work led him to become Mr. Money in the Bank, and his good fortune only continued from there. In November of 2010, Miz cashed-in his MITB contract to become WWE Champion for the first time, defended the title against John Cena in the main event of WrestleMania XXVII, and has since become an integral part of WWE programming.

The Miz went from a reality TV star to one of the most talked-about names in professional wrestling. He put in solid work beforehand, but the ascent of "The Awesome One" truly began at Money in the Bank 2010.

There's no denying that the aforementioned 2017 women's Money in the Bank ladder match was rather controversial. Thankfully, future incarnations like that at Money in the Bank 2020 proved not only more enjoyable to watch, but offered more satisfying conclusions. As noted previously, the women's MITB match was contested just like the men's in 2020, requiring participants to climb to the top of WWE HQ to secure the briefcase. This time around, Shayna Baszler, Lacey Evans, Nia Jax, Asuka, Carmella, and Dana Brooke brought their A-game in hopes of becoming the next Ms. Money in the Bank.

When the final bell rang, none other than "The Empress of Tomorrow," Asuka, held the Money in the Bank briefcase in her hands. So began the period where fans would debate week after week when they might see a cash-in, but for the first time in history, that's not at all how things panned out. The following week on "Raw," then-Raw Women's Champion Becky Lynch revealed that she would leave WWE programming for the time being due to her pregnancy. She invited Asuka to the ring, opened her briefcase, and out fell the title, making her the new champion in her stead.

In the wake of this heartwarming moment, Asuka went on to hold the Raw Women's Championship for just over two months before losing it to Sasha Banks. Overall, her title reign was far from memorable, but the manner in which she won the title certainly is.

WrestleMania 23 is remembered for a handful of reasons these days. There's the Battle of the Billionaires between Vince McMahon and Donald Trump, as well as the show-stealing World Heavyweight Championship match between Batista and the Undertaker. Of course, there's also the Money in the Bank ladder match from that year, featuring Jeff Hardy, Edge, CM Punk, Mr. Kennedy, King Booker, Matt Hardy, Finlay, and Randy Orton. The match was fun to watch and included some breathtaking spots — the most iconic from WWE's resident daredevil Jeff Hardy — but the winner is often overlooked by history.

Mr. Kennedy was the one to unhook the Money in the Bank briefcase that year, guaranteeing himself a WWE or World Heavyweight Championship match at a time and place of his choosing. As we now know, though, this impromptu bout and his theoretical title reign never came to pass. On the May 7, 2007 edition of "Raw," an injured Kennedy put his briefcase on the line in a match against Edge, who defeated his loud-mouthed opponent for the MITB contract. "The Rated-R Superstar" later cashed-in the briefcase on the Undertaker to become the new World Heavyweight Champion.

The sky was the limit for Mr. Kennedy in WWE until it wasn't, with the loss of his Money in the Bank briefcase signaling the downward trajectory of his run in the company. At least he'll go down in history as the first person to ever lose their MITB contract before they got the chance to cash-in.

Heading into Money in the Bank 2019, speculation ran rampant over who could possibly take the men's briefcase that year. Would Baron Corbin or Randy Orton repeat history and win MITB again? Would Drew McIntyre or Finn Balor rectify their losses in previous matches? Or would newcomers Ali, Andrade, or Ricochet take home the title match contract in their first attempt? All seven men fought hard to leave the XL Center with a guaranteed WWE or Universal Championship match in hand, but when the smoke cleared, none of them could lay claim to being 2019's Mr. Money in the Bank.

Ahead of the event, Sami Zayn managed to take Braun Strowman's place in the MITB match — much to the dismay of "The Monster Among Men." Therefore, when Zayn was found beaten down backstage, he was unable to take part in the ladder match. With a spot open, a returning Brock Lesnar with Paul Heyman in tow joined the match at the last moment to successfully retrieve the briefcase. Immediate reactions to Lesnar's return and victory were far from favorable, though at least we got the timeless image of "The Beast Incarnate" dancing around with the briefcase on his shoulder like a boombox.

It's up to individual interpretation whether or not WWE made the right call at Money in the Bank 2019, with Brock Lesnar's unexpected victory, but as the old saying goes, bad press is better than no press.

Just as they were in the previous four years, WWE fans were treated to a Money in the Bank ladder match at WrestleMania 25. Under the bright lights of Houston, Texas' Reliant Arena, Kofi Kingston, Shelton Benjamin, CM Punk, Mark Henry, Finlay, Christian, Kane, and MVP competed for a chance at the WWE or World Heavyweight Championship. All eight of them gave the match everything they had, with Benjamin taking a particularly big risk in pursuit of the MITB contract. However, his efforts and those of six other men were all for nothing as CM Punk took home the briefcase that night.

CM Punk's Money in the Bank win at WrestleMania 25 isn't just notable because it's CM Punk, who has a penchant for staying in the headlines. On that night, he became the first person in history to win two MITB ladder matches and do so in back-to-back matches. Much like he did with his WrestleMania XXIV contract, Punk cashed-in his WrestleMania 25 one to become the new World Heavyweight Champion. He won the title at Extreme Rules 2009 by defeating Jeff Hardy, who he'd go on to feud with throughout the year in one of the most well-remembered rivalries of this era.

WrestleMania 25 saw CM Punk make Money in the Bank history, ensuring that particular match took a special place in the history books. Not to mention, the title reign that came after it thrust "The Second City Saint" into the main event spotlight — even if Punk feels his WWE run was an overall waste of time.

As shown with the likes of the Miz, CM Punk, and more, Money in the Bank has the power to change careers. So long as one cashes-in successfully, that briefcase has the potential to take someone from the middle of the card to the main event. This holds especially true for Daniel Bryan, who took his place among history's many MITB winners in 2011. At that year's Money in the Bank event, the WWE's resident underdog overcame Wade Barrett, Cody Rhodes, Sheamus, Heath Slater, Kane, Justin Gabriel, and Sin Cara to secure the blue briefcase and a chance to become the next World Heavyweight Champion.

With the Money in the Bank contract in hand, Bryan became more of a highlight of "SmackDown" than he already was. After a turbulent few years in WWE — even being fired in 2010 — everyone was ready to see him finally win the big gold belt, and in December of 2011, it finally happened. He cashed-in his briefcase on Big Show at TLC: Tables, Ladders, and Chairs to become the new World Heavyweight Champion. Thus, the dominoes were in place for Bryan to become WWE's next big megastar, and within only a few years, he'd reach the mountaintop at long last.

When looking over Daniel Bryan's rise to WWE superstardom, his victory at Money in the Bank 2011 is a key piece of the puzzle. Without it, one has to wonder if, when, and how he would've reached the top of the card.

At WrestleMania 22 in 2006, the second Money in the Bank ladder match took place with a shot at either the WWE or World Heavyweight Championship on the line. "Nature Boy" Ric Flair, Bobby Lashley, Matt Hardy, Rob Van Dam, Finlay, and Shelton Benjamin all walked into the Allstate Arena with their eyes on the prize, and they were more than willing to risk life and limb to secure the briefcase. After a highly entertaining match, RVD stood tall as the second-ever Mr. Money in the Bank. With that, "The Whole Dam Show" embarked on arguably the best run of his entire WWE career.

As the Money in the Bank contract holder, RVD became the WWE Intercontinental Champion by defeating Benjamin at Backlash 2006. Though he'd lose the title not long after, it didn't much matter, bearing in mind that he still had a guaranteed world title opportunity in his back pocket. He ultimately cashed-in his sweet airbrushed briefcase in advance, challenging WWE Champion John Cena to a title match at ECW One Night Stand 2006. It took no shortage of intestinal fortitude (and Edge's timely interference), but Van Dam went home with the championship that night, and to top it all off, he was then awarded the ECW Championship once the brand rebooted and held the titles simultaneously.

Rob Van Dam's Money in the Bank win skyrocketed him to the top of the WWE mountain, making him the first — and so far only — person to hold the WWE and ECW Championships at the same time. It's just too bad that Van Dam's real-life circumstances led to the premature end of his Cinderella story.

With WrestleMania 21 on the horizon, WWE fans had a host of matches to look forward to. From the clash between former Evolution teammates Triple H and Batista with the World Heavyweight Championship on the line to a long-awaited battle between Shawn Michaels and Kurt Angle, excitement was indeed high. That goes double for the brand new match type that would debut at the event: the Money in the Bank ladder match. Chris Jericho's brainchild turned out to be nothing short of a highlight that would become one of the most talked-about WWE attractions of all time.

Jericho, Christian, Edge, Chris Benoit, Kane, and Shelton Benjamin braved this new in-ring frontier, diving head-first into the chaos of Money in the Bank. While it was really anyone's game, Edge walked back up the entrance ramp that night as the inaugural Mr. Money in the Bank. In the weeks that followed, an air of excitement overtook "Raw," as fans eagerly waited on him to cash-in his opportunity. It finally happened in January of 2006 when Edge turned his contract in for a WWE Championship match against John Cena, which he won to become a world champion in WWE for the first of many times.

With Edge's fateful cash-in at New Year's Revolution 2006, Money in the Bank was solidified as a star-maker. "The Rated-R Superstar" was officially a main-event talent, and it stood to reason that a similar outcome awaited those who'd follow in his footsteps down the road.

In June 2016, it came time for the seventh-annual Money in the Bank pay-per-view event, and the field for the year's ladder match was quite impressive. Former "NXT" standouts Sami Zayn and Kevin Owens, seasoned veteran Chris Jericho, and rising stars Alberto Del Rio, Dean Ambrose, and Cesaro looked to scale the rungs and secure an opportunity at the WWE World Heavyweight Championship. Ambrose wound up seizing the opportunity, and much like a handful of past MITB winners, he didn't wait too long to cash-in his contract and add more championship gold to his trophy case.

The Money in the Bank 2016 main event saw a returning Seth Rollins challenge WWE World Heavyweight Champion Roman Reigns for the title. The two former Shield teammates threw everything they had at each other, and when the final bell rang, "The Architect" stood triumphant as the new champion. However, he didn't get much of a chance to celebrate before the final third of the defunct Shield, Dean Ambrose, hit the ring with his briefcase in hand, using it to attack Rollins. The referee called for the opening bell, Ambrose scored the pinfall, and he became the new WWE World Heavyweight Champion.

In addition to having one of the shortest turnaround times in Money in the Bank history, Dean Ambrose's contract win also produced another interesting stat: with his victory over Rollins, who defeated Reigns for the WWE World Heavyweight Championship moments earlier, all three former Shield members held the title in one night. Thus, the 2016 MITB ladder match is among the most memorable of the modern era.

Seth Rollins shocked the wrestling world in 2014 when he turned on his longtime stablemates Dean Ambrose and Roman Reigns, dissolving the wildly popular Shield faction. Now a member of the Triple H and Stephanie McMahon's Authority, he was more than ready to strike out on his own and make an impact as a singles competitor. Naturally, this brought him to the 2014 Money in the Bank event, where he competed against Rob Van Dam, Jack Swagger, Dean Ambrose, Dolph Ziggler, and Kofi Kingston in the namesake ladder match with the coveted briefcase firmly in his sights.

Despite the stiff competition, "The Architect" unhooked the gold Money in the Bank briefcase and took a step toward wrestling immortality. For the next several months, he'd keep a tight grip on the case, as fans wondered when he'd ultimately decide to cash-in. They finally got their answer when Rollins — who lost to Randy Orton earlier in the night — sprinted down the WrestleMania 31 ramp at the perfect moment during the WWE World Heavyweight Championship showdown between Reigns and champion Brock Lesnar. He took the title for his own, closing out "The Show of Shows" as the new WWE World Heavyweight Champion.

Dubbed "The Heist of the Century," Seth Rollins' WrestleMania 31 Money in the Bank cash-in is undeniably the most memorable of them all. He overcame two of WWE's biggest names and solidified himself as the next big main eventer, shocking audiences at WWE's biggest show of the year in the process.