Shawn Michaels’ 10 Best WWE Matches Of The 1990s, Ranked

Two-time WWE Hall of Famer Shawn Michaels is unquestionably one of the greatest wrestlers of all time. The Heartbreak Kid is a fantastic in-ring competitor and he has the total package as he is an entertainer and he can speak on the mic. Michaels was a part of the Rockers with Marty Jannetty but when they broke up in 1992, the only way was up for Michaels.

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Michaels is a three-time WWE Champion and he featured in a plethora of high-profile feuds in the '90s. The Heartbreak Kid has put on instant clinics and some of his greatest matches in the '90s are among the greatest matches in WWE history. Some of the matches he competed in the '90s were match-of-the-year candidates, which is a testament to his greatness.

10 Shawn Michaels Vs. Bret Hart - Survivor Series 1997

The personally-fueled rivalry between Shawn Michaels and Bret Hart reached a bitter end at Survivor Series 1997. The Hitman defended the WWE Championship in front of his Canadian fans in Montreal, and Michaels was looking to become a double champion as he was the reigning WWE European Champion.

This was their second meeting at Survivor Series in six years, and to date, it's the only Survivor Series rematch. They brawled before the bell sounded, and it was a good wrestling match between the pair. However, it was a controversial finish as Michaels cinched in the Sharpshooter on Hart, and referee Earl Hebner called for the bell with Michaels escaping as WWE Champion for the third time.

9 Shawn Michaels Vs. Jeff Jarrett - In Your House 2: The Lumberjacks, 1995

Shawn Michaels and Jeff Jarrett locked horns in an underrated Intercontinental Championship match at In Your House 2: The Lumberjacks in July 1995. Double J entered the bout as the defending Intercontinental Champion, and this was arguably Jarrett's best match in a WWE ring.

This was a back-and-forth match with some good exchanges between the pair. The Roadie interfered on several instances to give Jarrett a helping hand, but their plans were thwarted in the end as Michaels nailed Jarrett with Sweet Chin Music to become a three-time Intercontinental Champion.

8 Shawn Michaels Vs. Diesel - In Your House: Good Friends, Better Enemies, 1996

Shawn Michaels' first WWE Championship title defense was against his former tag team partner Diesel at In Your House: Good Friends, Better Enemies. The result was inevitable as Diesel was on his way out of WWE to join WCW.

This No Holds Barred match was a quality encounter, and credit has to be given to Big Daddy Cool as he could have put in a half-hearted performance, but he did the job for his real-life friend. It was a stern test that Michaels passed in a successful WWE Championship title defense.

7 Shawn Michaels Vs. Marty Jannetty - Raw (7/19/93)

A premium live event quality match featuring Shawn Michaels and Marty Jannetty for the Intercontinental Championship took place on the July 19, 1993 taping of Raw and it was outstanding. The former tag team partners were both desperate to escape with the Intercontinental Championship in a fascinating battle.

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Michaels was on the backfoot for parts of the match as Jannetty had the upper hand. HBK suffered a slight scare with the referee restarting the match as Michaels' foot was placed on the bottom rope. Ultimately, the night belonged to Michaels who managed to retain the Intercontinental Title.

6 Shawn Michaels Vs. Bret Hart - WrestleMania 12

One of the biggest matches in Shawn Michaels' career occurred at WrestleMania 12 as he was seeking to win his maiden WWE Championship when he challenged Bret Hart for the gold in a 60-minute Iron Man match. Parts of the match flowed nicely, and the other parts were a bit slow.

There were no falls throughout the full hour, and they went into overtime. A couple of minutes into overtime, Michaels brought a halt to proceedings as he saw off his rival with Sweet Chin Music with the Boyhood Dream coming true with Michaels finally becoming the WWE Champion.

5 Shawn Michaels Vs. Razor Ramon - SummerSlam 1995

Fans were in store for a treat at SummerSlam 1995 when Shawn Michaels and Razor Ramon clashed in a ladder match for the Intercontinental Championship. This saved the show from being an utter disaster, and it was by far the best match of the night.

The Bad Guy was looking to execute the Razor's Edge on Michaels, but Michaels found a way to reverse it. They had a fantastic match as expected, and Michaels picked up a huge win by seeing off Ramon and retrieving the Intercontinental Championship.

4 Shawn Michaels Vs. Bret Hart - Survivor Series 1992

Shawn Michaels was the reigning Intercontinental Champion but he had his eyes set on Bret Hart's WWE Championship, and the duo collided in the main event of Survivor Series 1992 for the WWE Championship. This was a huge step for Michaels in his first year as a singles competitor, and he kept up with Hart.

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This match doesn't get spoken about as much but it's arguably the best match in their trilogy of WWE Championship matches. It wasn't Michaels' time to move into the main event scene but it gave him a taster with Hart continuing his maiden run as WWE Champion.

3 Shawn Michaels Vs. Razor Ramon - WrestleMania 10

Ladder matches became a fixture at WrestleMania, and the first one was at WrestleMania 10 when Shawn Michaels and Razor Ramon were pitted with each other to become the Undisputed Intercontinental Champion. They hit a home run in a breathtaking ladder match and the stakes were high.

Michaels had a brilliant outing and he executed a splash off the ladder onto the Bad Guy. Nevertheless, Ramon regrouped and pushed Michaels off the ladder leaving Michaels helpless in the ropes, and he collapsed to the mat after clinching both Intercontinental Championships that were hanging in the balance.

2 Shawn Michaels Vs. Mankind - In Your House: Mind Games, 1996

The WWE Championship match between Shawn Michaels and Mankind at In Your House: Mind Games was better than many expected it to be. Mankind was just five months into his WWE career, and he proved that he could hang with the major names in WWE.

The Heartbreak Kid didn't have everything his way in this title bout as Mankind was hellbent on winning the WWE Championship. Furthermore, there was a spectacular spot with Mankind attempting to back-body drop Michaels through the broadcast table, but in mid-air, Michaels countered it and put Mankind through it. Both men were protected with the finish as Michaels retained the WWE Championship albeit by disqualification.

1 Shawn Michaels Vs. The Undertaker - Badd Blood: In Your House, 1997

Badd Blood: In Your House featured the inaugural Hell in a Cell match and two of the all-time greats in Shawn Michaels and The Undertaker went head-to-head with the winner going on to face Bret Hart for the WWE Championship at Survivor Series 1997. This was an instant classic and a five-star epic with the storytelling and in-ring action on point.

The Deadman dominated large portions of the match, but Michaels hung in there and capitalized on any opportunities that he created. Michaels took a tumble through the broadcast table from the side of the cell, and Undertaker nailed Michaels with an earth-shattering chair shot. Michaels wore the proverbial crimson mask, but Kane made his WWE debut and he ripped off the cell door and laid out his brother with a Tombstone. Michaels crawled across The Undertaker booking his date with his bitter rival Bret Hart at Survivor Series 1997 for the WWE Championship.