WWE booking Roman Reigns vs Randy Orton in a champion vs champion match at Survivor Series 2020 provided the rare appeal of a heel vs heel match even if it didn't happen. Both wrestlers have found their groove playing villainous characters that do whatever it takes to pull out victories. WWE rarely places two heels in a matchup against each other since the audience is often unsure of who to root for.
The right story can make the match work in the right setting. WWE has found success with quite a few matches of its kind throughout the years. There is usually a variable in play that adds more to the match than just two hated figures working against each other.
10 Bret Hart vs Shawn Michaels (Survivor Series 1997)
The Montreal Screwjob is always going to be remembered for the ending of the match between Shawn Michaels and Bret Hart. However, it could have had a different legacy if WWE went through with the actual planned ending.
Both wrestlers were all-time great workers and had a tremendous start by brawling all over the arena, each playing a heel at the time. The match could have been a classic if not for the abrupt and all-time confusing ending. Even with the Montreal Screwjob, the actual match was going well.
9 Billy Kidman vs X-Pac (Invasion 2001)
The Invasion storyline of WCW and ECW wrestlers coming to take over in WWE. One of the more underrated feuds of the time featured WCW Cruiserweight Champion Billy Kidman having a few matches with WWE Light Heavyweight Champion X-Pac.
WWE’s first PPV of the storyline titled Invasion featured the two wrestlers representing the smaller division having a good match. Kidman scored the win for The Alliance by having a strong debut PPV match in the new promotion.
8 Brock Lesnar vs Test (King of the Ring 2002)
Brock Lesnar winning the 2002 King of the Ring tournament saw him getting fast-tracked to the main event picture just a few months after his debut. The first of his two matches on the PPV saw Brock matching up against a fellow big man heel Test.
Both wrestlers brought it for a short yet fun hard-hitting match. Lesnar showing a new side of his skill set scored a huge victory before defeating Rob Van Dam in the finals. The ability to work new styles of matches helped him get over even more for his world title run.
7 Trish Stratus vs Stephanie McMahon (No Way Out 2001)
The unlikely pairing of Trish Stratus and Stephanie McMahon had an entertaining match at No Way Out 2001. Trish dating Vince in a bigger storyline saw Stephanie getting involved with her resentment towards Stratus playing out in the ring.
The lack of in-ring experience for both at the time saw them having a story-based match with a few surprising spots. Stephanie won with help from William Regal to continue the angle.
6 Shawn Michaels vs Rick Martel (SummerSlam 1992)
WWE started to push Shawn Michaels as a heel in the early ‘90s after the split with Marty Jannetty to end The Rockers. Michaels showed great potential in the first stint of his new character with Sherri Martel as his manager.
SummerSlam 1992 saw Michaels facing off against fellow heel Rick Martel in one of the first heel vs. heel matches on a WWE PPV. Both wrestlers worked well together in the unique match before it ended in a double count-out.
5 Triple H vs Kurt Angle (Royal Rumble 2001)
WWE found a great storyline in the love triangle of Triple H, Stephanie McMahon, and Kurt Angle. The two heels had chemistry to continue the program even though neither made sense in the face role. Angle winning the WWE Championship saw him defending against Triple H at the Royal Rumble 2001 event.
Triple H was at the top of his game and provided the perfect middle ground as a cool heel to challenge Angle. Both wrestlers worked well to have a great match despite the heel dynamic going both ways. Angle stole the victory as the last major defense of his reign before losing it one month later.
4 Randy Orton vs Edge (Raw: April 30, 2007)
The Rated RKO tag team of Randy Orton and Edge found success in big matches against D-Generation X. WWE planted the seeds of them turning against each other when both wanted to move into the world title picture at the expense of the other.
One episode of Raw featured the big singles match since they always had multi-man matches on the PPVs of the time. Fans cheered for Orton due to the heat for Edge at the time. Orton won the crowd support, but Edge scored a huge victory.
3 The Shield vs The Wyatt Family (Elimination Chamber 2014)
The faction warfare between The Shield and the Wyatt Family saw both heel factions becoming acts that the fans loved watching. WWE appeared to have their stars of the future with the stables.
Elimination Chamber 2014 saw both teams facing off while still heels. The fans clearly supported The Shield in the match since they were planting the seeds for an upcoming face turn. WWE booked the Wyatt Family to win one of the best matches of the year.
2 Owen Hart vs Davey Boy Smith (Raw: February 26, 1997)
The European Championship was introduced in 1997 and saw Owen Hart and Davey Boy Smith facing off in the finals to be the first title holder. Both brothers-in-law had a respectful matchup based on competition during their heel run as a tag team.
The fans cheered Smith in Germany to defeat Owen for the historic victory. Everyone expected Owen to attack his partner afterward, but the two embraced in a rare feelgood moment between heels. The duo continued to team up moving forward with great success.
1 Brock Lesnar vs Daniel Bryan (Survivor Series 2018)
Daniel Bryan winning the WWE Championship days before a dream match against Brock Lesnar at Survivor Series 2018 saw Bryan turning heel for the first time in six years. The appeal of the match was still there even though fans were unsure of Bryan’s role.
Brock was the dominant Universal Champion in the Raw vs Smackdown match. The performance of Bryan was magnificent, both showing his heel side and still finding a way to get fans behind him. Lesnar pulled out the victory, but it was a must-watch match for Bryan fans.