#5 WWF Champion Randy Savage & WWF IC Champion Bret Hart vs Ric Flair & Shawn Michaels
“Macho Madness: The Ultimate Randy Savage Collection”
July 20th, 1992
Worcester, Massachusetts
This match is a fun favorite of mine, and arguably far lower in most fans’ eyes than the previous entry. This match is important for two reasons. It’s a rare teaming up of the WWF and Intercontinental Champions, and it is the ONLY time Flair and Shawn Michaels teamed up on tape prior to 2008. Also, this match was seen on television in the French edition of WWF Superstars, but, unseen by an American audience for years. Flair and Savage were feuding over the WWF Championship throughout 1992, copied by Bret Hart and Shawn Michaels feuding over the Intercontinental Championship, which is the backbone to this match. One group represented wrestling in the 1980s, and the other group represented the 1990s in a clash of style and era. Randy Savage pinned Shawn Michaels here with a roll-up at 17:16 to win the match for his team.
Why This Match Was Important: This match was a gift to the fans in Worcester, Massachusetts that night, and for those of them who still remember it, they witnessed history. Both Bret Hart and Shawn Michaels were eager to break away from their “tag tea specialist” mantra that the company dictated them into, and yet they found themselves in a marquee tag team match with legendary names. They would go on to forge perhaps the most profitable era in wrestling history together over the next couple years, while Flair and Savage moved on to WCW. But it was here in 1992 that eras collided in a very fun high caliber tag match of Hall of Fame talent.
What Should Have Happened: It’s hard to find what the company could have done better here; after all at SummerSlam 1992, Bret Hart and British Bulldog wrestled an all-time classic for the Intercontinental Championship, and Warrior and Savage had a great match in-which Flair involved himself as well. There was no Saturday Night Main Event in the summer of 1992 either, so finding a spot for this in the pre-RAW era is very difficult. Overall, the best the company could have done would be to announce a Saturday Night Main Event prior to SummerSlam and had these four men in the main event, highlighting their feuds. There is no excuse to not have this type of star power as a main attraction on some form of television during a time where the company was at a cross roads.

#4 WWF Champion Ric Flair vs Bret Hart
“WWE’s Top 50 Superstars of All Time”
Saskatoon, Saskatchewan, Canada
October 12th, 1992
WWF Championship
On September 1st, Ric Flair defeated Randy Savage at a WWF Superstars taping to win his second WWF Championship in the conclusion of their year long feud where they exchanged the championship twice. The Ultimate Warrior was named number one contender, but was fired from the company shortly thereafter when he failed a drug test. On October 10th at a house show in Los Angeles, California, many in attendance believed Bret Hart beat Ric Flair for the WWF Championship, it was even reported on the nightly news, but, the referee ruled the match a disqualification win for Bret. On October 12th, Bret was given a rematch with the Nature Boy in his home country of Canada, and it was there after 26 minutes and 29 seconds, Bret Hart made Ric Flair submit to the Sharpshooter, capturing the WWF Title! He called it the greatest night in his life, thanked his family, the fans, and Flair.
Why This Match Was Important: It was the second time the WWE Championship had changed hands at a house show in just over a month. The WWF Championship was defended often at house shows, almost every night, but no one expected the title to ever formally change hands in a match that wasn’t being taped for television or Pay-Per-View! This was huge back then. It’s rare even today. It was a major event for the company and the championship, and it was the stepping stone for an approach the company would bank on “Anything can happen in the WWF!”, it also ushered in a new era for the company as the company shifted from big guys such as Hulk Hogan and the Ultimate Warrior, to technically sound workhorses like Bret Hart, Shawn Michaels, Mr, Perfect, and others.
What Should Have Happened: Nothing. There was nothing wrong with the way this match happened or the title switch. There were no shenanigans associated with it, and it was an epic match between ring technicians in the prime of their careers. Having this match happen in Canada was an incredible moment for Bret Hart, and the Canadians fans and supporters of the Hitman. I can’t even criticize changing the title twice in a month’s time on house shows, because the company needed that type of unpredictability in a time when most things were viewed as status quo.

#3 WWF Champion Randy Savage vs WWF Intercontinental Champion The Ultimate Warrior
“The Ultimate Warrior: The Ultimate Collection”
Boston, Massachusetts
February 11th, 1989
WWF Championship vs Intercontinental Championship
Savage and Warrior found themselves in an interesting position in early 1989, as they held the top two championships in the company, and were arguably two of the three most popular wrestlers as well. Fresh off a heel turn at The Main Event II, Savage took his character into a new direction; that of a paranoid champion, who was constantly looking over his shoulder, questioning whether or not someone would try to steal his spotlight. These two champions locked up in a battle where both titles were on the line in the Boston Garden. Randy Savage won the match but both men retained their championships when Savage dropped a double axe handle on Warrior to the outside who was brawling with Rick Rude, resulting in a count-out win for the WWF Champion.
Why This Match Was Important: A year before “The Ultimate Challenge” at WrestleMania VI, Ultimate Warrior found himself with an opportunity to win both the WWF and Intercontinental Championships here. Even though he could not get it done, we were given a glimpse of history as the stage was set for his battle with Hogan down the road. It also featured Savage being a completely different wrestler than he was a month before against Bad News Brown. The Champion was ruthless, he was mean, he was calculated, and it showed when he was dropped the axe handle from the top to the outside. That was desperation from a desperate, brooding champion.
What Should Have Happened: The company had bigger plans between Hogan and Savage at Saturday Night Main Event and WrestleMania V than to have these two mammoths collide for their respective titles. Also I firmly believe Savage should have faced Bad News Brown (see above) at the 1989 Royal Rumble, so that was not an option either. With all the plans in play, making this match happen on television seemed very difficult, and with the stipulation of Champion vs Champion, it couldn’t have happened after WrestleMania either. The only other option would have been to have them have a match on a feature attraction of Superstars. One could easily argue that Savage should have beat Hogan at WrestleMania, and these two could have had this match after that as well.
#2 WWF Champion Hulk Hogan vs Harley Race
“WWF Even More Unusual Matches”
June 14th, 1987
New York City, New York
WWF Championship – Texas Death Match
I fought with myself that this match should have been the number one match on the list, but I couldn’t sell myself on it. Hulk Hogan found himself at odds with The Heenan Family throughout 1986 and 1987, fending off all challengers, including King Kong Bundy at WrestleMania II, and Andre the Giant at WrestleMania III. During the summer of 1987, Hogan fired up a rivalry with a legend in wrestling, the eight-time NWA World Heavyweight Champion Harley Race. On the May 18th, 1987 house show at Madison Square Garden, Hogan defeated Race but Race attacked Hogan after the match, drilling him with his championship belt, and bloodying Hogan. Later on, Hogan returned and challenged Race for the next MSG show in June to a Texas Death match and said if he couldn’t beat Race, he would retire! A month later, the rematch happened, but it was not televised, and the WWF lost out on an opportunity for a summer blockbuster. Hogan defeated Harley Race
Why This Match Was Important: This was probably the first “dream match” in tape collectors eyes, as Race had carried the NWA throughout the late 1970s and early 1980s, and it was Hogan who launched Hulkamania in 1984, booming the wrestling business in to the stratosphere! It was a clash of household names, with the company fresh off the press release of Hogan vs Andre, this may have rivaled it in pure star power. It was a supercard match, and a huge attraction. With the success of Flair vs Race just four years before, the WWF could have bankrolled this match, but, they did not.
What Should Have Happened: Many fans around the country and the world knew the names Hulk Hogan and Harley Race. Had the company invented SummerSlam a year earlier, they should have main evented, with the same stipulation. It would have been a mad house with rabid fans in attendance, and millions more watching at home.

#1 Hulk Hogan vs Ric Flair
“Greatest Wrestling Stars of the 90s”
November 30th, 1991
New York City, New York
The greatest stars of their time were set to battle in the main event of WrestleMania VIII for the WWF Title, but the company wanted Ric Flair to win, and Hogan refused to “put Flair over”. When Ric Flair came to the WWF in 1991, he brought with him the NWA Championship and called himself the “Real World Champion”. He paraded around with the championship on WWF television. Hogan was reigning WWF Champion at the time, but the title was stripped due to controversial finishes to consecutive championship matches between Hogan and the Undertaker in late 1991. Ric Flair won the 1992 Royal Rumble, and the vacant WWF Championship by doing so in January 1992. The company retracted on their plans to have these mega superstars wrestle on the grandest stage of them all and used the excuse that attendance at the house shows they main evented were less than satisfactory. It was crap, because EVERYONE wanted to see that match. 15,000 fans at Madison Square Garden got to witness the spectacle at a house show, that was never to be on television. Ric Flair initially won the match by pinfall after he hit Hogan with a pair of brass knuckles handed to him by Mr. Perfect, but the referee reversed his decision and awarded the match to Hogan by disqualification. So even at a house show, neither man could come out looking good. What a disgusting finish. Blech!
Why This Match Was Important: If the previous match was a dream match, this match was made in the heavens. Ric Flair was brought in to the WWF so he could wrestle Hogan at WrestleMania, it was a battle of icons, a battle of faces of the NWA and WWF, a battle of world champions. It was supposed to George Washington against Abraham Lincoln, apple pie against American whiskey, Dale Earnhardt against Babe Ruth.. This match even was bigger than the WWF Title itself. It was not needed to highlight this rivalry. This was the match everyone wanted to see, which never got to happen on television or pay-per-view. It’s a tragic misstep by the company because what we ended up with instead (Savage vs. Flair and Sid Justice vs. Hogan) were shells of the build they had invested in for months.
What Should Have Happened: Hogan should have swallowed his pride with his vitamins and accepted to lose to Flair at WrestleMania. Vince should have sat down with him and told him that is what was happening. Period. No rebooking needed.