The Undertaker battles Shawn Michaels at two straight WWE WrestleMania events, ending The Heartbreak Kid’s WWE career in the process as Tiffany continues her look at The Streak!

The years 2009 and 2010 turned out to be huge for The Undertaker and the Streak. For years, one of the most glaring absences in terms of big names in the Streak has been Shawn Michaels. Between them, Michaels and Taker had a collective nearly 50 years  in WWE, but had seldom met in the ring. They had a feud in 1997/98 but that was interrupted by Kane and Michaels’ career ending back injury. The next time they met was at the 2007 Royal Rumble when they were the final two.

These years would show the WWE Universe just why the Undertaker and Shawn Michaels were considered two of the Greatest of All Time when they put on two AMAZING WrestleMania matches. Michaels would come closer than anyone before him to ending the Streak, but his quest would end in heartbreak, no pun intended.

WrestleMania 25 – Absolute Perfection
The Undertaker vs. Shawn Michaels

This was one of those matches where it didn’t really need a feud, but we got one anyway. RAW had a match to determine who would get the honor of facing the Undertaker at WrestleMania. Michaels entered as a surprise opponent and beat Vladimir Kozlov to be the man to face the Undertaker. The promos for this match were as outstanding as you would expect, contrasting the light of Shawn Michaels’ Christian Faith and the darkness of Taker’s supernatural, borderline Satanic persona. The Dream Match was set for the Silver Anniversary of WrestleMania.

Shawn descended from the ceiling, dressed in white, and accompanied by lovely choral music. As the Cherry Picker got to the floor, it was engulfed in white light and Michaels’ regular entrance music hit.

Undertaker, in a complete contrast to Michaels’ entrance, ascended from under the stage, accompanied, as if he’d actually come from the depths of Hell.

As both men were getting ready, there are a LOT of 16-1 signs out there. This is the first time I can remember where a good portion of the fans believed the Undertaker was going to lose.

I’m going to be honest, I didn’t take a lot of notes for this match. Even though I’ve seen this match several times in the ten years since it happened, I still find myself in awe of it and not wanting to miss a single second. This match is so incredible, it’s really hard to summarize and condense it into words. If you never watch another WrestleMania match, or if you’ve never seen a WrestleMania match before, make it this one. This is what great wrestling should be, the audience was on its feet the whole near thirty minute match.

This match honestly reminded me of the matches HBK and Taker had in late 1997 and early 1998, it’s unbelievable to think that this was the first one-on-one match these two have had since the Royal Rumble 1998 Casket Match that actually ended Michaels’ career for a few years.

Michaels put Taker in the Figure Four, but Taker’s height advantage, once he thought past the screaming pain in his legs, helped him get out of the hold by punching the living hell out of Michaels.

In an amazing departure from each of their styles, both men traded submission holds, Michaels used the Crossface of the late Chris Benoit and Taker used Hell’s gate, but both men were able to break the holds.

There was a frightening moment when Taker did his running dive and Michaels, who had been outside, seemingly injured, pulled the cameraman in front of Taker, who landed BADLY. At this point, Michaels decided to try and cut his losses and get a win anyway he could and tried to get the win anyway he could and got the ref to start the count, but Taker JUST managed to get in at the last second.

These two men beat the living hell out of each other, each hitting their finishers and neither man would go down. Taker even tried to hit a flying elbow, but HBK wisely got out of the way.

It really looked like Michaels was done for when Taker countered Skin the Cat with a Tombstone and Michaels KICKED OUT!! No one could believe it, including the Undertaker. Taker went for another Tombstone, which Michaels countered with a rather sloppy Tilt-a-Whirl DDT, but it did the job.

After that, it was a battle of the haymakers and Taker won that fight, but Michaels battled back, but he made the mistake of going for a flashy move one time too many. Michaels went for the moonsault and was CAUGHT in a Tombstone by Undertaker and that was all she wrote. 17-0.

Rating: 10/10

Highlights: Watch. This. Match!

WrestleMania 26 – Absolute Heartbreak
Streak vs. Career: The Undertaker vs. Shawn Michaels

After his devastating defeat at the hands of the Undertaker, Shawn Michaels became consumed with the idea of getting a rematch, thinking that he knew why he’d lost and he wanted to rectify the mistake.

Taker initially refused, stating he had nothing to prove to Michaels. Michaels, with the terrier like determination that always defined him, refused to take ‘No’ for an answer. When he cost Taker the World Heavyweight Championship at Elimination Chamber, Taker’s vengeance was unleashed. He agreed to face Michaels on one condition: Michaels had to put his legendary career on the line. The stage was set for one of the most emotional matches in WrestleMania history.

There were no flashy entrances this time. WrestleMania 26 wasn’t as big of a deal as WrestleMania 25, but it worked. Taker’s was amazing, as always. He came up from the floor again and was in the Lord of Darkness style robe and hood that he would wear for most of the next decade.

This match was every bit as physical as the one in 2009, Taker was clearly trying to get the quick win over Michaels, but Michaels refused to quit.

Taker landed wrong during Old School, giving Michaels an opening to attack Taker’s knee, but Taker would compensate by using his power moves, but it’s clear that his knee was bugging him.

HBK went for the Figure Four on the injured leg of Taker but it just seemed to make Taker angry and Taker remembered the counter and POWERED through the flip. Michaels went back to a submission on the leg and got a big boot upside his head.

Michaels went for a splash and was caught and Tombstoned on the floor by Taker. Since this match had no countouts or DQs, Michaels couldn’t be counted out. There was a moment when HBK countered the Last Ride into a facebuster, then went to the top rope for his flying elbow, but Taker countered it with his knees, then locked Michaels in Hell’s Gate, but Michaels countered with a roll through.

Taker’s nasty streak showed when he tried to Last Ride Michaels through the announce table, but Michaels countered, then spit in the devil’s eye by hitting a moonsault through Taker AND the table.

In the end, Taker’s power was too much for the ever valiant Michaels, and Michaels knew it, but he didn’t go down without a fight, provoking the Deadman with a slap to the face before eating a THUNDEROUS Tombstone. The Streak lived on at 18-0 and the legendary career of Mr. WrestleMania ended. To his immense credit, Taker was a chivalrous victor. After a brief celebration with the fans, he pulled Michaels to his feet, embraced him, and left the ring, letting the Heartbreak Kid take his final bow with the fans.

I’m not going to lie, as much as I love the Undertaker, this is the one match I wanted him to lose because I couldn’t fathom a WWE without Shawn Michaels, who I’d been watching since I was six years old. He was my first crush and he was my hero, no matter how out of control he got. Thank you, Shawn.

Rating: 9/10 It wasn’t QUITE as good as the first match, but it was pretty close.

Highlights: Taker and HBK embracing and Taker leaving so HBK could say goodbye to the fans.