Shawn Michaels enjoyed an illustrious career in the WWE that spanned two decades, and he absolutely dazzled with his remarkable and never-before-seen in-ring work.
We got to see Michaels go up against many of the all-time greats during his career in the WWE. This included showdowns against Triple H, Hulk Hogan, Ric Flair, 'Stone Cold' Steve Austin, The Undertaker, Batista, John Cena, and Goldberg, among many others.
But believe it or not, many of the all-time greats in WWE never once graced the ring with Shawn Michaels. And to this day, we continue to wonder what a match between HBK and these legends would have looked like.
10 10. Sgt. Slaughter
Not only did these two Hall of Famers never square off in a singles match, but they never even took part in a tag team showdown of any kind, either.
According to ProFightDB.com, Michaels and Sgt. Slaughter only shared the ring on three separate occasions: The 1992 Royal Rumble, 1994 house show Royal Rumble, plus a battle royale on the Dec. 18, 2006 episode of Raw.
Possible outcome: Let's give this one to Michaels. He turned heel in 1992 after turning on long-time Rockers tag team partner Marty Jannetty. It would have enhanced Michaels' big push as a singles competitor by having him defeat an established veteran like Sgt. Slaughter.
9 9. Brock Lesnar
At the end of the day, timing is the main factor as to why we never got to see The Beast Incarnate go head to head with The Heartbreak Kid.
Lesnar debuted for WWE in 2002 but left two years later to try out for the NFL's Minnesota Vikings. He returned to the company in 2012, two years after Michaels retired following a WrestleMania loss to The Undertaker.
Possible outcome: Depends on when this match would have happened. Lesnar was getting a massive push during his first tenure, and he's rarely lost since returning in 2012. Michaels had no problems losing to other legends like Undertaker, John Cena, Kurt Angle, and others. We're sure he would have happily given this victory to Lesnar.
8 8. CM Punk
The former World Champions were involved in the same tag team match on numerous occasions, but for some reason, WWE never pitted the two elite in-ring performers against one another.
It obviously didn't help that Michaels spent most of his tenure on Raw, whereas Punk was used primarily as a main eventer on SmackDown Live. But there were numerous opportunities to make a match happen between these two. WWE just never made it happen.
Possible outcome: This match would have taken place near the end of Michaels' career, where he would have surely put CM Punk over. We'll say that the latter comes away with the victory via pinfall in a dream showdown.
7 7. Sting
Sting was fighting for WCW during the Monday Night Wars, while Shawn Michaels was playing a prominent role with D-Generation X and WWE in the midst of the Attitude Era.
Of course, by the time Sting had joined WWE in 2014, Michaels was long retired. The Heartbreak Kid only returned to the ring for a tag team match with Triple H against the Brothers of Destruction at Crown Jewel last year. Both superstars are now retired, so you can close the door on the hope of a dream match.
Possible outcome: Vince McMahon usually chose his loyal WWE superstars to defeat the WCW legends when they came aboard. Without a doubt, Vince would have given HBK the victory in this one.
6 6. Booker T
Booker T was among the many big-named WCW superstars who came over to WWE following the demise of Ted Turner's company. This was an angle that is often referred to as "The Invasion."
Michaels and Booker T teamed up on Apr. 7, 2003 episode of Raw - where they defeated Chris Jericho and Triple H. They were both involved in the Elimination Chamber match at Survivor Series 2002 as well. But unfortunately, we never saw a one-on-one showdown between these two all-time greats.
Possible outcome: It simply would have come down to who was heel and who was babyface, as the two superstars portrayed both during the Ruthless Aggression Era. Both superstars deserve a win here, but let's give one to Booker T here. A victory over the Heartbreak Kid would have done plenty of good, regardless of whether he was a heel or a face.
5 5. The Ultimate Warrior
At Survivor Series 1989, The Ultimate Warriors consisted of the man pictured above, Michaels, Jannetty, and Jim Neidhart. They emerged victorious over The Heenan Family in a four-on-four match.
But otherwise, Michaels and Warrior never shared the ring again in a singles nor a tag match. The latter left WWE in 1992 and again in 1996, before joining WCW for a brief run in 1998. As such, the opportunity for a showdown against Michaels just never came to be.
Possible outcome: This would have likely been a victory for The Heartbreak Kid. Vince would have used Warrior to help Michaels get over. The latter was in the midst of his major singles push during Warrior's final years in WWE, so it would have made sense to give Michaels this win.
4 4. 'Rowdy' Roddy Piper
Throughout much of Roddy Piper's run as a top-tier heel on the WWE roster, Shawn Michaels was working in the tag team division with Marty Jannetty. That obviously limited the opportunities for a match between Hot Rod and The Showstopper.
Piper left WWE in 1996 and signed with the rival WCW promotion, which all but ended any hope of seeing him go up against Michaels.
Possible outcome: We're going to give this victory to Michaels. Like we said on the Ultimate Warrior entry, Vince would have probably used Piper to help HBK get over during his major push in the mid-90s.
3 3. AJ Styles
You can argue that Styles and Michaels are the two greatest in-ring performers in the history of professional wrestling. Because of their respective skill sets, wrestling fans can't help but dream of a match between these two.
In Jan. 2018, Michaels admitted that there were discussions about a match between he and Styles. Back in the summer, The Phenomenal One said that he reached out to HBK about a match, which the latter turned out.
Possible outcome: If Michaels had come out of retirement for this match, you have to figure he would have done so to help put Styles over. This would have been an epic match full of excellent pace and execution, but Styles would have surely been handed the W here.
2 2. Eddie Guerrero
Eddie Guerrero spent the majority of his WWE career on the SmackDown Live roster, while Shawn Michaels was used on Raw. But it doesn't stop us from sitting back and wondering how special a Michaels-Guerrero match could have been.
Maybe WWE would have pitted the two legendary in-ring performers against one another at some point. But Guerrero tragically passed away at the age of 38 in 2005, leaving behind wife Vickie and his three daughters.
Possible outcome: We'll have to give this one to Guerrero. WWE was using him as one of the top faces on SmackDown Live, and a win over Michaels (who had nothing left to accomplish at this point in his career) would have only helped Guerrero's push.
1 1.The Rock
This fantasy showdown is right up there with Steve Austin-Hulk Hogan and Sting-Undertaker in regards to the best that never took place.
Apparently, The Rock simply refused to work with Shawn Michaels. That's the reason why we never got to see The Showstopper challenge the People's Champion. True or not, the fact is that we'll never get to see an all-time classic between a pair of wrestling GOATS. And that's a shame.
Possible outcome: Once again, it would depend on the time and place, and which guy was portraying the face. But Michaels was still a proven main eventer during the Attitude Era, whereas Rock was slowly building his way up to the top. Let's go ahead and say that Michaels would have won this match, though it would have marked a "moral victory" for The Rock.