In WWE, booking a match between two heels is a rarity since the fans do not have a babyface to cheer for. There are instances where a heel vs. heel match has occurred and has even been the main event of the program the match was scheduled for. These matches have ranged from mediocre to very exciting depending on the wrestlers involved, and some of them have been forgotten about through time.
When heel vs. heel matches happen, it is usually on a TV taping and the results reflect the storyline the heels are participating in, whether the storyline is quality or not.
6 The Undertaker vs. Kurt Angle (SmackDown, 2002)
In the main event of the 4th of July edition of Smackdown in 2002, The Undertaker portrayed a heel that was in the middle of his "Biker Taker" run. He was also reigning as WWE Undisputed Champion, which he defended against Kurt Angle. This match featured two top-level performers in their physical primes and contained some suspenseful moments, one of which saw Kurt Angle deliver one of The Deadman's signature moves, the chokeslam, on The Undertaker after he twice escaped Kurt's ankle lock.
The Undertaker then hit his own chokeslam on Angle for a two-count. Undertaker then attempted his powerbomb, the Last Ride, which Angle countered into a triangle choke submission. As Angle applied the triangle choke, Undertaker managed to put Angle in a pinning position. This sequence led to a confusing finish where Undertaker tapped out while pinning Angle. Two referees discussed the proper decision, which ended up being a draw. Due to this draw, Undertaker retained his Undisputed Championship and Angle attacked Undertaker with his ankle lock to close the show.
5 John "Bradshaw" Layfield vs. Kurt Angle (SmackDown, 2005)
In the build-up to the 2005 Royal Rumble pay-per-view, JBL had been the defending WWE Champion for months beforehand. His two rivals for his championship defense at the Royal Rumble were Kurt Angle and Big Show. On the January 27 edition of Smackdown, the go-home Smackdown before the pay-per-view, JBL and Kurt Angle wrestled in a Last Man Standing Match.
This Last Man Standing Match came about due to some bickering earlier on the show between JBL's faction, The Cabinet, and Kurt Angle, along with his lackeys, Luther Reigns and Mark Jindrak. In the match itself, there was the typical No Disqualification in-ring action, including a top-rope superplex from JBL to Angle. Angle bounced back with 6 consecutive German Suplexes to JBL and due to both men's legitimate and kayfabe exhaustion from the intense physicality, the match resulted in a draw. The show closed with Big Show thanking Smackdown's General Manager, Theodore Long, for scheduling the match and saying he would win the WWE Title at the Royal Rumble.
4 Chris Jericho vs. Kane (SmackDown, 2009)
On the October 30 episode of Smackdown, Chris Jericho wrestled Kane for the opportunity to wrestle The Undertaker at Survivor Series for Taker's World Heavyweight Championship. This was a regular TV match with some of Jericho and Kane's usual offense, along with back-and-forth in-ring action. Some of those moves included Jericho's Lionsault, and Walls of Jericho submission hold. Kane hit his clothesline in the corner and his top-rope aerial clothesline as well.
The finish saw Jericho counter a Kane top-rope move with his Codebreaker facebuster signature move and pin Kane to win his way to the Survivor Series. Two WWE legends had a match here that was good enough for its purpose and provided the fans with a solid main event for a TV taping.
3 CM Punk vs. Dolph Ziggler (SmackDown, 2012)
On the October 5 edition of Smackdown, CM Punk was in the middle of his lengthy WWE Title reign from the prior November. Dolph Ziggler was being showcased as a singles star on the rise at this time and after Punk and Ziggler exchanged some heated words in a backstage segment regarding their dissolved alliance, then-General Manager Booker T booked Punk vs. Ziggler as that night's main event.
This match contained some quality, fast-paced action, including submissions, strikes, and signature moves. However, it was short, likely due to time restraints. The finish saw Dolph miss his splash in the corner and be hit by Punk's Go To Sleep, which led to Punk's victory. Since Punk was a heel whose character was about demanding respect for being a record-holding WWE Champion, Punk cut a promo about getting that respect through Hell in a Cell later that month against his then-rival, John Cena, to close that show.
2 Seth Rollins vs. Randy Orton (RAW, 2014)
On the November 3rd edition of RAW, Seth Rollins and Randy Orton were both members of the notorious Authority faction and had been in-fighting for a while beforehand. This particular episode of RAW happened during the build-up to the Survivor Series and Orton and Rollins were co-captains for Team Authority in the feature Elimination Match.
Triple H and Stephanie McMahon booked Orton against Rollins in that night's main event to settle their differences. The ensuing match was of the quality expected from Rollins and Orton, featuring engaging back-and-forth action with both of their usual offense. The finish saw Rollins defeat Orton with a surprise backslide pin, and while Orton putting Rollins over clean was a good way to increase Seth's momentum into main event status, the post-match assault is the memorable aspect of this match.
With the assistance of Corporate Kane, Jamie Noble, and Joey Mercury as J&J Security, Rollins attacked Orton after the bell, delivering a Curb Stomp to Orton through some steel ring steps off of the commentary table. The idea here was to write Orton off TV for a few months and set up Orton vs. Rollins again at WrestleMania 31. Orton turned babyface off of this match and angle, severing his alliance with The Authority, and a few months later, had a classic against Rollins at the aforementioned WrestleMania.
1 British Bulldog vs. Owen Hart (RAW, 1997)
On the March 3rd episode of RAW, WWE held a TV taping in Germany, which served as the appropriate place to have a match for the newly-introduced European Championship. British Bulldog and Owen Hart fought for the European Title in a tourament final, as brothers-in-law Tag Team Champions, and these two delivered a 20-plus minute peformance that featured some good back-and-forth technical wrestling.
At one point, Owen Hart attempted a middle-rope superplex, which Bulldog countered mid-move into a cross body block. Owen fought back with a suplex counter into a German suplex and the sequences continued of both high-flying and impactful manuevers, including Bulldog's Running Powerslam finisher. The finish saw Bulldog counter Owen's roll-up attempt into Bulldog's own roll-up for the win to become the first-ever WWE European Champion.