Top 20 Most Heartbreaking Losses in WWE History

The theme of this article is simple: Streaks end. Careers end, and thus, a part of our past also comes to a close. The matches listed below are the most heartbreaking kind of matches. When the bouts conclude, we often stand (or sit) in silence, either shocked or sad, but usually never disappointed.

The matches here have a little bit of everything. They kept you on the edge of your seat, made you clench your fists and also sweat a bit. You felt that with every blow to your favorite superstar, you were only seconds away from losing a part of yourself and your past. When the Undertaker finally lost to Brock Lesnar at WrestleMania 30, fans likely thought back to when the streak begin. Some weren't even born yet. Some were still running around the playground pretending to be The Phenom...even though that's somewhat disturbing.

The point is, these losses hurt more than a major win feels good. People don't like to press the restart button in their lives. After all, it takes too much time to get back to where they were prior to starting over. So, it feels even worse when someone else, in this case the WWE, presses it for you. It's a sucker punch to the gut.

Yet, as slightly depressing as this all sounds, these matches were epic. They are lodged into our memory forever. And, the truth is this: If the WWE always gave us what we wanted, why would we go back for more? These matches are part of what makes us love professional wrestling. They are a part of our childhoods, our teen years, and adult lives.

So, with that let's take a look at the most disappointing and certainly heartbreaking losses in WWE history.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

20 The Ultimate Warrior Loses Last WCW Match at Halloween Havoc

via wcwworldwide.com

He'd wrestle one last time in 2008, but the official end of the Warrior's career came in 1998 against the Immortal Hulk Hogan. Not many may remember the match primarily because it was horrible, but it was heartbreaking to see a man once at the top of the industry fall so far. Most would have at least liked to see The Warrior win his last match. However, prior to his death, many believe he did leave on top. Prior to his death, he ended feuds with Vince McMahon, Triple H and Ted Dibiase, and the WWE inducted him into their Hall of Fame.

19 Undefeated Tatanaka Loses to Ludvig Borga

via de.wwe.com

The reason Tatanaka's first loss hurt so much was because it seemed so unnecessary. After he beat Tanaka for his first ever win, Tatanaka (yes, they are two different wrestlers), went on a winning streak. He won a 40-Man Battle Royal and beat veteran Rick Martel and even Intercontinental Champion Shawn Michaels. His streak came to an abrupt end the day before Halloween 1993 on an episode of WWE Superstars. A force by the name of Ludvig Borga finally took down Tatanaka by using a steel chair and the assistance of Yokozuna. This was Ludvig's push to greater heights, but he failed to deliver due to an ankle injury that eventually cost him his job.

18 Lita Leaves the WWE in Disgrace

via killeroflegends.blogspot.com

When Lita joined the WWE, she was a fan favorite. She left the company anything but the revered superstar she once was. At the time of her departure, she was proclaiming herself "the greatest women's champion of all time," and damning crowds across the nation. Her actions might have actually made her leave a little easier for the WWE Universe to stomach. She lost her last match and title to Mickie James at Survivor Series 2006.

17 Bret Hart's Steel Cage Match

via thewwehistory.weebly.com

Hart never seemed able to get the upper hand against the WWE or its owner Vince McMahon. Besides the Montreal Screwjob, Hart's steel cage match against Sid is just another example of his misfortunate, but memorable run with the company. Hart faced numerous odds in the match. First, he had to escape the steel cage and second, he had to do so while fending off Stone Cold and The Undertaker, who had both interrupted the match. Hart lost the bout and later pushed McMahon to the ground when the Chairman tried to conduct a post-match interview.

16 Batista Loses "I Quit" Match and Quits WWE

via wweturkiyehaber.blogspot.com

As the Attitude Era drew to a close, new wrestlers began to emerge. Two wrestlers who rose to prominence were Batista and John Cena. Their careers ran parallel, both vying for a chance to put the WWE on their shoulders. They both wanted the recognition and there was only room for one at the top. Their chance to prove their worth came at Over The Limit 2010 in an "I Quit" match. Batista uttered the words, "I quit" and the next night he actually quit WWE for good... until he returned this year... before quitting again.

15 Kane Gets Unmasked

via sportzwiki.com

There was always an aura of mystery that surrounded Kane's character. We were told his face was scarred and how he felt about his brother The Undertaker, however, the mask still symbolized his repressed feelings. When Kane lost to Triple H inside Madison Square Garden, he was forced to take off his mask. When he did, those hidden feelings were released, unveiling a more deadly Kane the world was likely not ready for.

14 Brock Lesnar Embarrasses John Cena SummerSlam 2014

via bleacherreport.com

He not only lost the WWE Championship, but tons of pride in the process. Whether you are a fan or not of Cena, you had to be surprised by how Lesnar manhandled the WWE Champion. There was little in-ring confrontation between the opponents prior to the match, but it was a built up like a heavyweight UFC fight...Lesnar's specialty. Sixteen German Suplexs and a final F-5 brought the champion down for good.

13 John Cena Loses to The Rock at WrestleMania XXVIII

via we.com

There may have been more to this match than we'll ever know. "There is a giant underlying story that you may or may not know about...it's an interesting story, and obviously it's one that you want to hear about," said Cena on ESPN's Highly Questionable show with Dan Le Batard and Bomani Jones. Let's guess that it had something to do with The Rock's brief appearance and Cena believing he worked too hard not to win. The match had all the highlights. The Rock flying off the top rope, Cena attempting to disgrace The Rock's People's Elbow and all their finishers in between. Yet, in the end Cena walked away empty handed.

12 Fabulous Moolah's 28-year Title Reign Comes to An End

via jkwrestling.com

A number of female wrestler's have entered and left the WWE over the years. Some have been forgettable, but others have captured our hearts. Think Lita, Chyna, Sable, Ms. Elizabeth, and Trish Stratus. However, they pale in comparison to Moolah's run in the company. In 1956 she defeated Judy Grable for the vacant Women's World Title. Three decades later, Wendi Richter ended Moolah's title reign at The Brawl to End it All. Eventually, the WWE voted both women into the WWE Hall of Fame

11 Goldberg Loses First Match Against Kevin Nash

via pl.wwe.com

This might be one of the most impressive streaks in any sport. From the time he made his 1997 WCW debut, Goldberg fought his way to a 173-0 record. He seemed unstoppable, until he came toe-to-toe with nWo leader Kevin Nash at Starrcade 1998. In a sold out arena. Goldberg finally fell when Scott Hall tasered him and Nash used his patented Jackknife Powerbomb to secure the victory.

10 The Undertaker Defeats Hulk Hogan at Survivor Series 1991

via voicesofwrestling.com

In the early 1990's, Hulk Hogan was America's wrestler. He had stood up for the USA when Sgt. Slaughter turned heel and backed Iraq, and he won the 1990 and 1991 Royal Rumbles. He was on top of the wrestling world, which made his defeat against a young Undertaker all that more difficult to bear. It went something like this: Taker defeated Hogan. Bobby "The Brain" Heenan declared the death of Hulkamania. Children cried. Grown men and women wept. And then, Hogan won the title back six days later, but the initial shock was what people will remember the most.

9 Randy Savage Get Retired by Ultimate Warrior

via cinemablend.com

Savage faced possibly his toughest opponent and worst WrestleMania loss against the Ultimate Warrior. Five consecutive elbow drops couldn't keep the Warrior down, and the latter's fierce spirit ultimately helped him prevail. After the match, Savage's manager Queen Sherri attacked him in the ring as he lay helpless. Too much to bear, his former love, Miss Elizabeth, rushed from the audience to fend off Queen Sherri, and the crowd roared in approval.

8 Randy Orton Defeats Daniel Bryan at SummerSlam 2013

via cagesideseats.com

This is more than Bryan facing Orton. This is Bryan facing the WWE who seems always out to take down and then keep down the "B+ player." At SummerSlam 2013, Bryan had finally beaten the odds, and John Cena, to win the WWE title. Chants of "Yes!" screamed through the rafters of the Los Angeles' Staples Center. Yet, as quickly as they chants grew, they fell. Triple H hit Bryan with a Pedigree and Orton cashed in his Money in the Bank contract to steal the title away.

7 The Undertaker Retires Shawn Michaels at WrestleMania XXVI

via sportskeeda.com

HBK's long career extended back into the mid 1980s with The Rockers. He then went onto have a successful single's career and became an integral part in the most earth-shattering group in WWE history, D-Generation X. However, nothing could prepare The Heartbreak Kid for this WrestleMania moment. A chokeslam and two Tombstone Pile Drivers later, Michaels found himself motioning to the WWE Universe his gratitude for their undying love. He walked out defeated, but in the audience's mind, always on top. He left the biggest stage of them all, having fully earned the name Mr. Wrestlemania.

6 Stephanie McMahon Turns on Her Dad

via wwe.com

At Armageddon 1999, Stephanie McMahon took her fate into her own hands and changed the WWE forever. In November of that same year, she revealed she had married her father's rival Triple H. Enraged, Vince challenged The Game to a match at Armageddon, and if the latter lost, the marriage would be annulled. Near the match's end, Stephanie was about to hit Triple H with his own sledgehammer, but couldn't muster up the strength. When Vince finally lost, she revealed that she was on Triple H's side all along.

5 Shawn Michaels Retires Ric Flair at WrestleMania XXIV

via seenitheardit.com

Flair's legendary career came to a point at WrestleMania 24 when he faced Shawn Michaels in a "career threatening match." If Flair lost, he would have to retire. This bout was one of many "retirement matches" for Flair, who also had "career threatening" matches against Mr. Kennedy, MVP, Umaga, William Regal, Triple, and Vince McMahon. Flair lasted 30 minutes in the ring, but three Sweet Chin Musics by Michaels finally took the legend down.

4 Ivan Koloff Ends Bruno Sammartino Historic Title Reign

via wwe.com

There are few times when the WWE Universe falls silent, unable to come to grasps with what they just saw. Today it seems hard to surprise people. We feel like we've seen it all, but 43 years ago it was a different story. Koloff and Sammartino battled for the WWE Championship in front of 20,000 people. The latter had held it for a blockbuster 2,803 days. When Koloff pinned the champion, the crowd didn't cheer or boo. They weren't sure how to react and just sat there stunned.

3 The Montreal Screwjob

via de.wwe.com

Was it real, or the greatest kayfabe storyline the world of wrestling had ever seen? By the mid-1990s, the WWE was struggling financially, in many parts because of the successful and growing WCW. At the same time and for many reasons, Bret Hart had refused to lose the WWE Championship to Shawn Michaels at Suvivor Series in Montreal. To make matters more complicated, he had signed on with WCW. McMahon, nervous Hart would take the company's most prestigious title over to enemies lines, screwed Hart out of the WWE Championship. The decision caused a rift that still holds, in some part, to this day.

2 Hulk Hogan Defeats The Unbeatable Andre the Giant

via wwe.fr

By 1986 The Giant had become the premiere star in wrestling. Hogan was also a powerhouse. Both stood undefeated in their own respective categories. For two decades The Giant beat every wrestler imaginable. Hogan had also defended his WWE Championship for three consecutive years. When the two finally fought, the world watched on their edge of their seats and stood in disbelief when The Giant finally fell.

1 Brock Lesnar Breaks The Undertakers' WrestleMania Streak

via gaminrealm.com

Some streak-ending matches you just never get over. This is one of them. The Undertaker entered WrestleMania 30 with an epic record of 21-0. It seemed only natural that he'd continue the streak and retire on top...that is until Brock Lesnar came along. What surprised people the most was not that Lesnar beat him, but that the WWE didn't ask Taker to put over a more up-and-coming superstar.

More in Wrestling