The Undertaker Shawn Michaels WWE WrestleMania 25
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Best Matches Of The Undertaker’s WrestleMania Streak

For years, The Streak was one of the main selling points of WrestleMania. The Undertaker racked up 20 wins at WWE’s biggest show of the year, and nobody could stop him. As the years went on, the magic of The Streak grew, as some of WWE’s top stars waged war with “The Deadman” in an attempt to go down in history as the man who handed “The Phenom” his first loss at WrestleMania. Brock Lesnar eventually did, but The Streak was a special ride while it lasted.

These are the top 5 wins The Undertaker scored in his WrestleMania streak. Each of them delivered one of the most unforgettable matches of the night and built up the buzz surrounding the streak and the legacy of “The Deadman” himself.

The Undertaker vs. Batista – WrestleMania 23

These days, Dave Bautista is a leading man in Hollywood, as he recently starred in Knock at the Cabin, and he will reprise is role as Drax the Destroyer in Guardians of the Galaxy Vol. 3. But for many years, he was one of the faces of WWE. In 2007, the memory of his heated feud with Triple H was still fairly fresh, and while he as a major player, he needed a marquee match to fully cement himself as a top guy on WWE SmackDown.

Enter The Undertaker. “The Phenom” won the 2007 Royal Rumble by last eliminating Shawn Michaels, and he ultimately decided to challenge for Batista’s World Heavyweight Championship. What started as a somewhat respectful feud turned into an intense rivalry on the road to WrestleMania. “The Animal” and his challenger failed to coexist in a tag team match at No Way Out 2007, and the champion dropped ‘Taker with a ring-shaking spinebuster, setting the stage for an exciting clash at “The Showcase of the Immortals.”

The match lived up to the height and started with a big swing from Batista, as he dropped The Undertaker with a Spear at the opening bell. The two stars traded signature moves and tried to put their opponent down in a variety of ways; Batista even hit a running slam through the announce table, but “The Deadman” wouldn’t be denied. In the end, The Undertaker scored the win with a Tombstone to stretch his streak to 15-0 and win the title. Their feud continued, but this thrilling clash at WrestleMania was arguably the peak.

The Undertaker vs. CM Punk – WrestleMania 29

Unlike many of his other WrestleMania matches, the bout between “The Undertaker” and CM Punk is not ready available on WWE’s YouTube channel, given the former WWE Champion’s controversial exit from the company. That’s what makes the match between Punk and The Undertaker at WrestleMania 29 even more meaningful, at least in hindsight; one year later, Punk was gone, leaving many fans to wonder what could have been if things had turned out differently.

By the time 2013 rolled around, The Undertaker had firmly transitioned into a part-time role. He returned on the Old School RAW on March 4, and Punk earned the right to face the legend at WrestleMania by winning a four-way match against Randy Orton, Big Show, and Sheamus. Real life may have swayed the storyline, as Paul Bearer, The Underaker’s former manager, passed away, and Punk leaned on this loss on-screen. He crashed the tribute to Bearer on RAW, hit Kane with Bearer’s urn, and continued to utilize it in the feud. Punk went so far as to dress as a druid and pour ashes from the urn onto The Undertaker, giving this rivalry the riveting storytelling it needed.

Once the bell rang, both men delivered a remarkable match. While neither one was necessary at their best at this point in time, it’s hard to have anything less than a good bout between two greats. Paul Heyman, Punk’s manager, got involved, and “The Second City Saint” nearly stole the win after he hit the legend with the urn. The Undertaker ultimately scored the victory with a Tombstone, advancing his record to 21-0 and, though no one knew it at the time, handing Punk a loss in his final WrestleMania match.

The Undertaker vs. Edge – WrestleMania XXIV

Like Batista, Edge was a made man by 2008, as he was the top heel on SmackDown, and he had a firm grasp on the World Heavyweight Championship due to his alliance with La Familia. But The Undertaker came around and took names, determined to take the title from “The Rated-R Superstar.” At WWE Elimination Chamber, “The Phenom” earned a shot at the gold by winning the Elimination Chamber match; he fittingly eliminated Batista last to punch his ticket to WrestleMania.

The Undertaker had to deal with the meddling of La Familia over the next several weeks, and the stable heated up the feud by holding a mock burial for the challenger’s WrestleMania streak. Typical ‘Taker goodness ensued, as “The Deadman” crashed his own funeral by popping out of the casket.

Once it was time for the match, the 2008 version of The Undertaker could certainly still go, and he was working with one of the best in the game in Edge. The story of the bout centered around the champion having his challenger scouted, as Edge countered The Undertaker’s major moves. Edge got a convincing near fall after he hit The Undertaker with a camera and subsequently hit him with a spear. Not even interference from Curt Hawkins and Zack Ryder could help Edge change his fate, but rather than a Tombstone, The Underaker used the Hell’s Gate to counter the Spear and earn the hard-fought victory.

The Undertaker vs. Triple H – WrestleMania XXVIII

The last two items on the list are neck and neck. The Undertaker’s “End of an Era” Hell in a Cell Match with Triple H was one for the ages. The two legends battled it out in an unforgettable bout at WrestleMania 27, and they ran it back the following year, with the added stipulation and the presence of special referee Shawn Michaels to up the ante. Michaels lost to The Undertaker in consecutive years at WrestleMania, so he was the perfect choice for the role; he was Triple H’s long-time friend, but he was also well aware of the prestige and the value of The Streak.

This storyline also flipped the script, as The Undertaker gave Triple H a shot, rather than waiting for someone to challenge him, because he wanted to get a more decisive outcome than their previous encounter, where he was helped out of the arena. Triple H even tried to refuse, but Michaels eventually pushed him into accepting the challenge.

The match itself was a classic, aided by the presence of Jim Ross, who joined the commentary for the bout. Heart-pounding storytelling and brutal violence mixed together to create a symphony of excellent sports entertainment. More so than many other Streak wins, this one featured perhaps the closest near fall of all time, as Michaels hit a Sweet Chin Music (after initially being an impartial official), and Triple H hit a Pedigree for a 2.999. A few finishers later, The Undertaker put Triple H down with a Tombstone.

The only knocks on this bout remain that it was overshadowed by The Rock’s “Once in a Lifetime” match with John Cena, and it wasn’t the end of an era; despite the visual of Triple H, Michaels, and ‘Taker walking to the back together, Triple H and The Undertaker kept wrestling, and Michaels even came out of retirement years later. But in a vacuum, this Cell match was almost impossible to top.

The Undertaker vs. Shawn Michaels – WrestleMania 25

Almost being the key word, as there’s no way the first WrestleMania match between The Undertaker and Shawn Michaels could be anywhere but the top spot. At WrestleMania 25, the two icons renewed their rivalry, which stretched back to the 1990s, and delivered not just one of the best Streak matches, but one of the greatest WrestleMania bouts of all time.

This one somewhat lacked in story heading into the bout, compared to the Streak vs. Career rematch at WrestleMania 26. To be fair, Michaels special entrance, in which he came down on a platform and represented the light, whereas The Undertaker was the embodiment of the dark, was a beautiful choice. The in-ring action was unparalleled, as the two men threw absolutely everything they had at each other and wrestled like they were at least ten years younger. The two legends put their bodies on the line, as Michaels came up empty on a moonsault to the outside, and “The Deadman” landed hard on a dive to the floor.

Finisher after finisher, near fall after near fall, the action left everyone on the edge of their seats. The Undertaker clinched the thrilling win when he caught a diving Michaels and spiked him with a Tombstone for the three count.

Michaels and The Undertaker also delivered an amazing match at WrestleMania 26, and it’s fair to debate which one deserves to be on this list, but that’s an argument for another day.