Unlike other forms of entertainment, in wrestling, the bad guys don't always get their comeuppance. The babyfaces engage in a feud with the dastardly heels, and more often than not, they'll come out victorious, but it's far from a guarantee. The nature of the business demands strong villains that must be overcome - look no further than what WWE is doing with The Tribal Chief, Roman Reigns.
There are many past feuds where the heel actually came out on top, that wasn't so obvious at first glance. Whether it was to build momentum or create an interesting storyline, some wrestling fans might have forgotten that the following heels actually won their feud.
10 Daniel Bryan Vs. Bray Wyatt (2014)
In late-2013, WWE had done their best to move Daniel Bryan away from the main event picture and thrust him into a feud with Bray Watt and his Wyatt Family, at the time a very new and very popular act.
Bryan would eventually join the stable but weeks later betrayed Wyatt and destroyed him inside a steel cage, leading to one of the loudest reactions in RAW in years. But when the two met in the ring, Wyatt was victorious, setting the stage for the crowd to hijack the 2014 Royal Rumble due to Bryan not being involved in the battle for a main-event match at WrestleMania. The two did not face off again until late-2019 with Wyatt now in The Fiend character.
9 Kane Vs. The Undertaker (2010)
Throughout the summer of 2010, the main storyline on Smackdown was Kane looking for the superstar who brutally attacked his brother, The Undertaker, leaving him in a comatose state. Eventually, Kane won the World Heavyweight title and it was revealed he was the attacker.
This feud saw the return of Paul Bearer, who turned on The Undertaker, and Kane beating The Undertaker at every turn. This included a Buried Alive Match at Bragging Rights where for some reason The Nexus helped Kane take the win, the last one-on-one match between The Brothers of Destruction.
8 Bray Wyatt Vs. Dean Ambrose (2014)
Coming out of the breakup of The Shield in June 2014, it looked like Dean Ambrose was primed to emerge as a major babyface, earning huge reactions in the fall of that year. However, despite being featured in many high-profile matches, Ambrose constantly lost.
This trend continued when he entered into a feud with Wyatt in late-2014, with Ambrose losing a TLC match with a hideous finish where a television monitor blew up in his face, making him look rather idiotic. Wyatt continued to win every match in the feud, derailing a lot of Ambrose's momentum.
7 Sting Vs. Ric Flair (1990-91)
In early 1990, the wheels were set in motion for Ric Flair to pass the torch to Sting, who was seen as the future of WCW. While everything was delayed due to Sting's knee injury, he eventually would defeat Flair for the NWA World Title at the Great American Bash.
Over the next few months, Sting was put into the horrible feud with The Black Scorpion, who ended being revealed as Flair because there were no other viable options. Flair would win the title back from Sting a few weeks later, and The Four Horseman beat Sting's team in War Games in February 1991, ending their lengthy feud.
6 Ted DiBiase Vs. Jake "The Snake" Roberts (1989-90)
The feud between Ted DiBiase and Jake Roberts ran almost exactly one year between WrestleMania V and VI, mostly due to Roberts suffering a neck injury. It had many twists and turns including Roberts stealing DiBiase's Million Dollar Belt, and The Big Boss Man becoming a face after refusing to be bought off by DiBiase.
While many older fans will remember this feud, they may not know it was DiBiase who won the final battle at WrestleMania VI, taking back his title in the process by way out of count-out. Even though Roberts hit a DDT after the match and then shoved money down DiBiase's throat, the latter has to be considered the winner of the feud.
5 Randy Orton Vs. Daniel Bryan (2013)
In the summer of 2013, it looked like Daniel Bryan was well on his way to a reign as WWE Champion. The leader of Yes Movement was selected to face John Cena at Summerslam with Triple H as the special guest referee. Bryan won that match but lost the title immediately as HHH turned heel and helped Randy Orton cash in his Money In The Bank briefcase.
The feud between Orton and Bryan was based on WWE officials feeling Bryan wasn't worthy of being champion, or a "B+ Player." After constant beatdowns by Orton and The Shield, and the insertion of The Big Show into the storyline, the feud ended with Orton beating Bryan in a Hell in a Cell match due to the interference of Shawn Michaels, who was retired and would never face Bryan in a match.
4 The Undertaker Vs. Shawn Michaels (1997)
It took seven years before The Undertaker and HBK finally engaged in a feud and it ended up being one of the most important in the Attitude Era. It saw the introduction of both the Hell In The Cell match and the character of Kane.
Many will likely forget that The Undertaker was never able to score a decisive win over Michaels, who won a casket match against at the 1998 Royal Rumble to wrap up their battle. Of course, it wasn't the last time they faced off.
3 Randy Orton Vs. Triple H (2009)
The first question many may ask when they see these names is 'which feud?' but this was the highest-profile match-up they were involved in. It started with Orton punting Vince McMahon in the head and then DDTing his daughter Stephanie as HHH was handcuffed to the ropes.
While The Game was surprisingly able to win the WrestleMania main event between the two, Orton would eventually take the title off him and punted him as well. A few months later, The Viper won a Three Stages of Hell between the two, and Triple H transitioned to feuding with Legacy along with Michaels.
2 Bret Hart Vs. Stone Cold Steve Austin (1996-97)
The Bret Hart vs. Stone Cold Steve Austin feud was the launching pad for the biggest double turn in the history of the WWE and the beginning of Austin becoming one of the greatest superstars in wrestling history.
After Austin turned face in spring 1997, the feud began to transition to The Hart Foundation against Austin and a group of his allies, including Goldust, The Legion of Doom, Mankind, Michaels, and Ken Shamrock. However, Austin never got a definitive win over Hart of any kind.
1 JBL Vs. The Undertaker (2004)
When JBL literally came out of nowhere in 2004 to become the WWE Champion, it was only a matter of time before he crossed paths with arguably Smackdown's most pushed act at the time, The Undertaker.
JBL would win a poorly received match at Summerslam 2004, which ended with Undertaker getting DQ'd for hitting the champ with the title. The two would face off again in the first-ever Last Ride match, which JBL won with help from Heidenreich.