For a pretty significant period of time, The Undertaker was regularly the biggest attraction at WWE's biggest show of the year, as his match was regularly the most anticipated contest on the show.
In recent years, excitement for The Undertaker at WrestleMania has died down a bit, especially this year. As of this writing, "The Deadman" hasn't officially been added to the Mania card, and if he doesn't end up making an appearance, it'll be the first time he's missed the annual show since its 16th installment back in 2000.
While it's safe to say that The Undertaker's best in-ring days are clearly behind him, that doesn't mean that we can't appreciate some the work he's done at WrestleMania, both the good and the bad.
This was Randy Orton's first significant singles match at WWE's biggest show of the year, and it ended up being a pretty good one. At the time, Orton was someone who the company was hoping to build around in the future, so their goal was to protect him in a loss to The Undertaker, who still had his WrestleMania undefeated streak intact. Aside from the show's main event, where Batista won the WWE World Heavyweight Championship for the very first time by defeating his mentor Triple H, Taker vs. Orton was the most memorable match on the card.
Widely considered to be the worst WrestleMania of all time, WrestleMania 9 featured a match between The Undertaker and Giant Gonzalez, which was arguably "The Deadman's" worst match ever at the event. At the time, The Undertaker's streak wasn't something that WWE was building up, as they had the future Hall of Famer defeat Gonzalez via disqualification, making it his least satisfying victory of the streak by far. To be fair though, the quality of the match wasn't The Undertaker's fault, as Giant Gonzalez is remembered for being one of the worst in-ring performers of all time.
In what was probably his last great WrestleMania match, The Undertaker took on CM Punk back at WrestleMania 29, which ended up being the best match on the entire show by a country mile.
The match was pushed as the third biggest match on the card behind Triple H vs. Brock Lesnar, which was a complete dud, and behind the rematch between John Cena and The Rock, which wasn't the greatest match, but it's hard to argue that a CM Punk match is more noteworthy than a match featuring two of the biggest superstars WWE has ever created. Unfortunately, Punk didn't end up breaking the streak, because that role was reserved for Brock Lesnar, who ended up pinning The Undertaker the very next year.
While this match will always be significant due to the fact that it was The Undertaker's first loss at WWE's biggest show of the year, but it's not going to be remembered as an all-time classic match. To be fair, this is largely because "The Deadman" suffered a concussion pretty early in the match which clearly hindered his ability to perform at a high level. We did see the two have some pretty incredible matches later on in their rivalry, but this one was pretty rough. But, despite it being less than stellar, this match will be remembered for quite a while due to its historical significance.
While it wasn't quite as good as their first match the year prior, The Undertaker and Shawn Michaels still delivered an all-time classic performance back at WrestleMania 26. It was supposed to be the final match in the legendary career of Shawn Michaels, and he did honor that stipulation until last year, when WWE was able to offer him a significant amount of money to come back for a tag team match against the man who retired him. But, even though Michaels did come back for the Saudi Arabia show, WWE will likely try to ignore that match, and instead push the WrestleMania 26 match as HBK's final performance.
This was supposed to be a pretty big deal, as it was The Undertaker's first appearance since losing to Brock Lesnar at WrestleMania 30. Sure, "The Deadman" didn't look all that bad in the match, but it was less than memorable, and very underwhelming when it happened. But you could say the same for most of Bray Wyatt's pay per view matches, so it probably had more to do with the opponent than it did with The Undertaker himself. In the end, "The Deadman" was able to prevail and get back on the winning track at WWE's biggest show of the year.
While The Undertaker and Triple H did compete against one another back in 2001 at WrestleMania 17, that match has been overlooked by the two classics they had at the 27th and 28th installment of the event. Some do believe that the first of the two consecutive matches was better, but their second match, which took place inside Hell in a Cell with Shawn Michaels as the special guest referee, had far more twists, and a lot more drama.
In fact, the match featured what might be the hottest near-fall in the history of the event, as Triple H and Shawn Michaels hit The Undertaker with a Sweet Chin Music/Pedigree combo which many believed was the finish of the match.
This was the first match where it was clear that The Undertaker had lost a step or two, which was to be expected, as "The Deadman" was 52 years old at that point. The point of the match was to set Roman Reigns up for a match against Brock Lesnar at the next year's WrestleMania, with the idea being that there'd be a Universal Championship match between the only two WWE stars who had beaten The Undertaker on the company's grandest stage. While Roman's performance was pretty good, you probably couldn't say the same thing for the future WWE Hall of Famer's performance, which was less than stellar.
This was the first of two classic WrestleMania matches between Shawn Michaels and The Undertaker, and it ended up being arguably the greatest match in the history of the event. In fact, this match was so great that even legendary in-ring performers such as Triple H and CM Punk failed to top it at future WrestleMania events. Even the great Shawn Michaels couldn't even top his own performance from Mania 25 when he and The Undertaker had their rematch the very next year. Even if you don't think this is the best match in the history of WWE's biggest show, there's no way you can argue against it being the best match of The Undertaker's career.
To be fair, this match could've been good if it was about 15 minutes shorter. It was a match that the fans had a ton of interest in because it was Shane McMahon's return to the ring after a long hiatus. On top of that, the stipulation was that if Shane won, he'd gain full control of WWE in storyline, which was something that the fans were really excited about. But unfortunately, the match just dragged on and on, as it was the longest match on the WrestleMania 32 card, clocking in at 30:05. The match was really nothing special, and its only big moment is when Shane jumped off of the top of the cell and came crashing down through the announcer's table. Aside from that, this was just a half hour of nothing.