The Undertaker's WrestleMania streak ending was a significant moment from his career, and everything after that point was seen as his final run. From that defeat to Brock Lesnar, the Deadman was firmly a part-time worker, and he was coming towards the end of his run, which led to a mixed bag in terms of match quality.
While his character was always interesting and gained reactions from the WWE Universe, inside the ring, his performances weren't always great. The Undertaker had to deal with a lot of injuries at this point in his life, which did hamper his matches, with some being poor, and others being fantastic.
10 Best: The Undertaker vs. Triple H (Super ShowDown, 2018)
This was a no disqualification match that took place in Australia, with WWE putting together these two legends for one final encounter. It brought a big fight feel and the fans were invested in seeing them compete. Both men were able to look good, and it's no surprise they worked well together after so many years competing.
The place was rather slow at times, but that suited both of them, as they were unable to work at a breakneck pace. While the match certainly dragged on for too long, lasting for almost 30 minutes, it was an enjoyable encounter that felt worthy of a PPV.
9 Worst: The Undertaker vs. Rusev (Greatest Royal Rumble, 2018)
The Undertaker is someone WWE has pulled out a lot of times when they have headed to Saudi Arabia, and of his encounters was against Rusev. This was a casket match that had originally been booked for Chris Jericho, but he got replaced by Rusev. It would likely have been stronger if this had stuck to the original plan, purely from a storyline and chemistry point of view.
The match was not too bad here, but it felt very much like a live event quality encounter. There was nothing memorable about it, and the complete lack of storyline stopped fans from having any real reason to emotionally invest in this one, which hurt it.
8 Best: The Undertaker vs. Shane McMahon (WrestleMania 32)
This Hell in a Cell match was one of The Undertaker's final truly memorable encounters that fans will still talk about throughout history. This was pushed heavily in the build, and the two men worked hard inside the ring together, putting everything on the line in what was a truly physical encounter.
They threw everything into this one, attacking each other with weapons, working some great wrestling, and the famous bump as Shane launched himself off the roof. This one did go on slightly longer than it needed to be, but there was no doubt that it was a good WrestleMania encounter.
7 Worst: The Undertaker vs. John Cena (WrestleMania 34)
There was nothing particularly wrong with this match, but it was a disappointing one in terms of length. They only had almost three minutes, which made it essentially a squash. The Undertaker did look good within this encounter, but the entire bout was put together in order for it to just be a showcase for him.
It wasn't a classic match like some fans had hoped it would have been. The two of them are capable of much more than what they put together here, which is why it ended up being one of the worst matches from his final run, simply because people wanted more.
6 Best: The Undertaker vs. AJ Styles (WrestleMania 35)
The WrestleMania 35 Boneyard match between The Undertaker and AJ Styles was the final encounter of his career, and it ensured the Deadman went out in style. With the COVID-19 pandemic changing things up, they were forced into a cinematic encounter, but this was perfect for Undertaker.
It meant things could be filmed and edited, and it ensured that he looked amazing. AJ was bumping around like crazy, and the variety of weapons and use of the environment was spectacular. It was over-the-top and utterly ridiculous, but that was a fitting finish to the career of this particular gimmick.
5 Worst: Brothers Of Destruction vs. D-Generation X (Crown Jewel, 2018)
The Brothers Of Destruction competing against D-Generation X was a strange one to see at this point in time. All four men were past their best and Shawn Michaels even came out of retirement to be involved. While there was a lot of star power on offer, inside the ring things did not turn out as planned.
From Triple H getting injured to Kane's mask flying off within the match, things just didn't work out. In the past, this could have been an epic encounter, but sadly this is one match that all four men likely regret being involved in.
4 Best: The Undertaker & Roman Reigns vs. Shane McMahon & Drew McIntyre (Extreme Rules, 2019)
This match came together quite randomly, but it ended up being an amazing one. The Undertaker was at his best here, looking sharp, hitting his big moves with Drew McIntyre and Shane McMahon bumping well for him. Having it be a tag team encounter meant that Roman Reigns could put together a lot of the work himself.
It hid Undertaker's flaws and led to him looking fantastic. There was a lot of excellent in-ring psychology taking place, and the fans went crazy for the entire encounter. It was a reminder of just how good 'Taker could be, even at this late stage in the game.
3 Worst: The Undertaker vs. Roman Reigns (WrestleMania 33)
This was a night that a lot of people thought would be The Undertaker's last, and had the match been a good one, it very well could have been. Unfortunately, this encounter was incredibly poor, which hurt the show overall as it was the main event. Roman Reigns was good here, but sadly the Deadman had a poor night.
His injuries caught up with him for this one, which was why he was slow and sluggish in certain spots. At one point he couldn't lift Roman, and the fact the encounter featured botches didn't help. It's an encounter that 'Taker himself has admitted wasn't good, and sadly it didn't live up to the hype surrounding it.
2 Best: The Undertaker vs. Brock Lesnar (Hell In A Cell, 2015)
The Undertaker's streak being ended by Brock Lesnar was something that led to the two of them having a series of matches. They competed inside Hell in a Cell at one point, which was a match fans weren't sure about. However, it led to a fantastic match, with The Undertaker still looking at his best within this one.
He and Brock Lesnar always worked perfectly inside the ring, going back and forth with a hard-hitting encounter. They pushed each other to their limits in a match that featured some fantastic wrestling. But it so utilized the steel structure itself, which was important, and it showcased just how talented the Deadman was at structuring an encounter.
1 Worst: The Undertaker vs. Goldberg (Super ShowDown, 2019)
Without a doubt, the worst match of The Undertaker's final run with the company came against Goldberg. It was a dream encounter for a lot of fans, but it didn't live up to the hype. There were a lot of issues within this contest, with some serious bumps that almost led to serious injuries for both men.
Goldberg suffered a concussion within the match, and that stopped the encounter from ever reaching the potential that it could have had. It was a struggle to watch, because neither man was able to reach the level that they were capable of, which was a shame to see.