Road To WrestleMania
Chairshot Top 5: The Undertaker’s WrestleMania Streak Matches
Relive The Undertaker’s greatest WrestleMania Streak matches, ranked from 5 to 1, including classics against Shawn Michaels, Triple H, CM Punk, and more.
Relive The Undertaker’s greatest WWE WrestleMania Streak matches, ranked from 5 to 1, including classics against Shawn Michaels, Triple H, CM Punk, and more.
The Undertaker’s Streak wasn’t just about wins. It was about expectation. It was a match that became more important than wrestling for a world title on the grandest stage.
Every year, WrestleMania came with one constant: no matter what else was on the card, The Undertaker was going to deliver something that felt important. Sometimes it was about dominance. Sometimes it was about survival. And in the later years, it became about legacy.
Not every match was equal, but the best ones didn’t just protect the Streak. They elevated it. These are the matches that defined what the Streak meant.
5. WrestleMania 21 — Randy Orton vs. The Undertaker
This was the moment the Streak became a story.
Randy Orton didn’t just challenge The Undertaker. He targeted the Legend himself. The “Legend Killer” angle gave the match purpose, and for the first time, it felt like a loss for The Undertaker was a real possibility.
The match delivered on that premise. Orton controlled long stretches, played the role perfectly, and created believable near-falls that made the outcome feel uncertain. It wasn’t the most dramatic Streak match, but it was the one that shifted the perception. From here on out, the Streak wasn’t just a record. It was something people wanted to see broken.

4. WrestleMania 29 — CM Punk vs. The Undertaker
This match had a different kind of weight to it, all thanks to the work of CM Punk.
Coming off the real-life passing of Paul Bearer, CM Punk leaned all the way into the role of antagonist, pushing the story into uncomfortable territory. That edge gave the match a level of intensity that went beyond the usual WrestleMania build.
Inside the ring, it delivered exactly what it needed to. Punk’s pacing, combined with Undertaker’s presence, created a match that felt deliberate and physical without relying on spectacle. It wasn’t about topping previous Streak matches. It was about telling the right story at the right time, and it did that extremely well.
Honorable Mention – WrestleMania 26 — Shawn Michaels vs. The Undertaker
The rematch added stakes with Shawn Michaels’ career on the line, giving the match a different kind of emotional weight. It didn’t quite reach the same level as their first encounter, but it didn’t need to. The story was about finality, and the ending delivered exactly that.
3. WrestleMania 24 — Edge vs. The Undertaker
This is simply one of the most complete Streak matches from top to bottom, and Edge’s first WrestleMania main event.
Edge entered as World Heavyweight Champion and fully embraced the role of opportunist, constantly looking for openings and advantages against The Undertaker. The dynamic worked perfectly, creating a match where the challenger wasn’t just trying to survive. He was trying to outthink his opponent.
The pacing, the counters, and the finish all landed. Edge never felt outmatched, and Undertaker never felt vulnerable in a way that broke the aura. It was a balance that’s hard to achieve, and it made this one of the most satisfying Streak matches without needing extra stipulations.
2. WrestleMania 28 — Triple H vs. The Undertaker (Hell in a Cell)
By this point, the Streak had grown into something bigger than wins and losses.
Triple H vs. Undertaker inside Hell in a Cell, with Shawn Michaels as special referee, was built around legacy, pride, and the idea that the Streak might cost Undertaker everything. It wasn’t just about whether he would win. It was about whether he should keep going.
The match leaned into that completely. It was slower, more deliberate, and more emotional than previous entries, with every moment carrying weight. The finish didn’t just preserve the Streak. It reinforced what it represented. At this stage, the Streak wasn’t just intact. It was almost untouchable.
Honorable Mention – WrestleMania 23 — Batista vs. The Undertaker
Batista vs. Undertaker is often overlooked, but it played a key role in evolving the Streak into a main event-level attraction. The match was physical, fast-paced, and centered around the World Heavyweight Championship, helping elevate the importance of Undertaker’s WrestleMania presence moving forward.

1. WrestleMania 25 — Shawn Michaels vs. The Undertaker
This is the standard for big matches in all of professional wrestling.
Shawn Michaels vs. Undertaker at WrestleMania 25 is widely regarded as one of the greatest matches in WWE history, and for good reason. It had everything: pacing, storytelling, near-falls, and a level of crowd investment that elevated every moment.
What made it stand out wasn’t just the quality. It was the balance. Michaels felt like a legitimate threat without undermining the Streak, and Undertaker delivered a performance that matched him step for step. The result was a match that didn’t just define the Streak. It defined WrestleMania itself.
The Undertaker’s WrestleMania Streak worked because it evolved with the character, and the event itself.
It started as a statistic, became a storyline, and eventually turned into one of the defining legacies in wrestling history, and it’s biggest trophy. The best matches weren’t just about keeping it alive. They were about making it matter. And when it mattered most, it delivered.
Chairshot Radio Network
Launched in 2017, the Chairshot Radio Network presents you with the best in sports, entertainment, and sports entertainment. Wrestling and wrestling crossover podcasts + the most interesting content + the most engaging hosts = the most entertaining podcasts you’ll find!
MONDAY - Bandwagon Nerds (entertainment & popular culture)
TUESDAY - 4 Corners Podcast (sports)
WEDNESDAY - The Greg DeMarco Show (wrestling)
THURSDAY - Nefarious Means
FRIDAY - DWI Podcast (Drunk Wrestling Intellect)
SATURDAY - The Mindless Wrestling Podcast
SUNDAY - 30 Mindless Minutes
CHAIRSHOT RADIO NETWORK PODCAST SPECIALS
Attitude Of Aggression Podcast: The Big Five Project (chronologically exploring WWE's PPV/PLE history) Unidentified History (Ufology) & Game Gone Wrong (Game of Thrones Universe)
Chairshot Radio Network Your home for the hardest hitting podcasts... Sports, Entertainment and Sports Entertainment!
Powered by RedCircle
Let us know what you think on social media @ChairshotMedia and always remember to use the hashtag #UseYourHead!
Opinion
Chris King Looks Back: WWE WrestleMania 36
Chris King takes a look back at one of the most surreal wrestling events of all time, 2020’s WWE WrestleMania 36!
Chris King takes a look back at one of the most surreal wrestling events of all time, 2020’s WWE WrestleMania 36!
As we get geared up for WrestleMania 42, one of my favorite things to do is go back and watch previous Manias and find that special magic again. Six years ago, we were living in a worldwide pandemic and nothing felt the same. WrestleMania 36 was supposed to be held in Tampa Bay but, unfortunately it took place inside of the Performance Center.
For the first time in WWE history, WrestleMania was split into two nights, which would become a constant going forward. Each night would feature a plethora of matches including Goldberg vs. Braun Strowman for the Universal Championship, Seth Rollins vs. Kevin Owens, AJ Styles vs. The Undertaker in a Boneyard Match, and Brock Lesnar vs. Drew McIntyre for the WWE Championship.
On Night one, one of the greatest bouts with an incredible build would be ‘The Messiah’ Seth Rollins vs. Kevin Owens. Rollins had been fighting for the greater good flanked by The Authors of Pain and Buddy Matthews and blatantly destroying Owens on multiple occasions. Rollins portrayed the perfect manipulating heel here.
The resilient ‘Prizefighter’ was so sick of Rollins’ crap that he challenged him to a match at Mania. What started as a simple match, quickly turned into an all out brawl with no disqualifications. Both superstars fought all over the ringside area, and KO would climb off the huge WrestleMania sign and hit a massive elbow drop! Owens would pick up the huge victory over The Messiah.
Braun Strowman would challenge Goldberg for the Universal Championship in what was relatively a squash match. Roman Reigns was supposed to challenge Goldberg, butdue to health concerns, he took a hiatus from WWE. ‘The Monster Among Men’ would take four massive Spears from the veteran and retaliate with four running power slams to win his first Universal Championship!
The main event of night one saw The Undertaker battle AJ Styles in a really fun and chaotic boneyard match. This dream match was supposed to take place in front of 75,000 screaming fans but, this was truly the perfect ending to Taker’s illustrious career. Styles had some massive balls calling out his opponent by calling him by his official name and disrespecting his family. ‘The Phenomenal One’ just kept poking the bear all the way into their match. Watching Styles arrive in Undertaker fashion inside of a coffin and give a maniacal laugh was hilarious. All the games were over after Taker rode in on his motorcycle to beat his ass!
The Deadman would have to face off against The OC, and even his druids to shut his opponent up once and for all. Taker delivering a massive chokeslam and tombstone piledriver on the roof was a sight to see. Taker kicked Styles right into his own grave and rode off into the darkness, as usual! The Undertaker cross symbol blaring through the fire while Metallica plays was iconic! Taker would be so satisfied with the cinematic match that he would formally retire later that year!
Night Two of WrestleMania 36 was awesome and electric, as Edge faced off with his greatest former friend now rival Randy Orton in a last man standing match, John Cena faced off with ‘The Fiend’ Bray Wyatt inside the Firefly Funhouse, and Drew McIntyre looks to win his first-every WWE championship from ‘The Beast Incarnate’ Brock Lesnar!
Edge made his shocking return at the 2020 Royal Rumble, after a career-ending neck injury. Randy Orton was excited to see his former Rated-RKO partner but he quickly put a stop to a reunion in a disgusting manner. Orton delivering a vicious Concerto to Edge and hitting an RKO on Beth Phoenix brought back flashbacks to ‘09 Orton and his feud with Triple H!
‘The Viper’ came out of nowhere disguised as a cameraman to hit an RKO to start the match. Orton was a mastermind here playing the sinister antagonist to Edge’s comeback story. Both superstars went to war throughout the performance center in a hard-hitting performance. Orton choking out Edge while saying “I’ll always love you, man” was just vile and really fun to watch. Edge finally got the advantage in the gym area using the machines to gain some revenge.
They fought through the backstage areas, a boardroom all the way to the top of an NXT production truck. Orton hitting his signature draping DDT on the bed of a pickup truck was nasty. The Viper tried to Punt Edge’s lights out but, got hit with a massive spear. Edge got the final shot hitting Orton with a devastating Concerto to win the match!
John Cena entered The Firefly Funhouse for one of most spectacular cinematic masterpieces of all time. This match was a cinematic journey of John Cena’s history within the company, and looking back at his greatest failures. It was so interesting to see how his future could have been way different had he turned heel, instead of maintaining being a babyface who was shoved down our throats for years! Bray Wyatt as ‘The Fiend’ finally got his comeuppance after Cena refused to put him over at Mania 30.
Wyatt was red-hot at that time but, Cena gave him his greatest defeat of his career. The Fiend may not have been created if it wasn’t for this loss on the grandest stage of them all. Wyatt would defeat Cena and go on to become the Universal Champion months later.
The final match of the grand event was Drew McIntyre defeating Brock Lesnar to win his first WWE Championship. After Lesnar’s impressive performance at the Royal Rumble, McIntyre humiliated him by eliminating him and punching his ticket to the biggest match of his career. The way WWE hyped McIntyre is very similar to how they are hyping Oba Femi right now. They made him look like an unstoppable beast.
The match started with a free trip to Suplex City followed by a F5 for a kickout at one! Lesnar’s eyes grew wide as his opponent kept coming back. ‘The Scottish Warrior’ would not stay down and, The Beast was getting pissed. McIntyre would ultimately slay the beast hitting four massive Claymore kicks to win his first WWE Championship! Paul Heyman has a look of shock and disappointment as McIntyre poses with his title. What a way to end WrestleMania 36!
Chairshot Radio Network
Launched in 2017, the Chairshot Radio Network presents you with the best in sports, entertainment, and sports entertainment. Wrestling and wrestling crossover podcasts + the most interesting content + the most engaging hosts = the most entertaining podcasts you’ll find!
MONDAY - Bandwagon Nerds (entertainment & popular culture)
TUESDAY - 4 Corners Podcast (sports)
WEDNESDAY - The Greg DeMarco Show (wrestling)
THURSDAY - Nefarious Means
FRIDAY - DWI Podcast (Drunk Wrestling Intellect)
SATURDAY - The Mindless Wrestling Podcast
SUNDAY - 30 Mindless Minutes
CHAIRSHOT RADIO NETWORK PODCAST SPECIALS
Attitude Of Aggression Podcast: The Big Five Project (chronologically exploring WWE's PPV/PLE history) Unidentified History (Ufology) & Game Gone Wrong (Game of Thrones Universe)
Chairshot Radio Network Your home for the hardest hitting podcasts... Sports, Entertainment and Sports Entertainment!
Powered by RedCircle
Let us know what you think on social media @ChairshotMedia and always remember to use the hashtag #UseYourHead!
Opinion
Chris King: Will Oba Femi Be A Made Man At WWE WrestleMania 42?
WrestleMania 42 represents the opportunity for WWE to launch Oba Femi into the stratosphere against Brock Lesnar
WrestleMania 42 represents the opportunity for WWE to launch Oba Femi into the stratosphere against Brock Lesnar
Oba Femi will take on Brock Lesnar in his first match at WrestleMania, and this match feels so important. ‘The Ruler’ has had Lesnar’s number for several weeks, and they even had to keep both monsters apart to prevent another massive brawl on the go-home episode of Monday Night Raw.
‘The Beast Incarnate’ is hoping to continue his reign of terror against the young up-and-comer, while Femi is looking to cement his legacy with the biggest win of his career. It took me a minute, but the last time there was so much importance in a Lesnar match was at WrestleMania 36.
At that time, Drew McIntyre was trying to make the biggest impact on his career by slaying The Beast.
Long before Covid happened, the entire WWE Universe was fully behind McIntyre after eliminating Lesnar and then winning the Royal Rumble. Lesnar worked his ass off to make sure his challenger looked like a million bucks.
There was an instance where McIntyre hit a Claymore Kick, and there were rumors that Lesnar told his challenger to raise the title to build more momentum going into their match. While the WWE Championship match was held inside of the Performance Center due to COVID, Lesnar utilized everything he could to make McIntyre’s moment that much more special.
Since then, Lesnar has dominated a plethora of opponents including John Cena, Cody Rhodes, and even Roman Reigns. The Beast recently joined The Vision inside their WarGames match. On the February 23rd episode of Monday Night Raw, Paul Heyman and his client Lesnar laid out an open challenge to any superstar for a match at WrestleMania Night Two.
On the March 16th episode of Raw, Femi answered The Beast’s WrestleMania challenge by hitting his Fall From Grace Powerbomb. Lesnar was rumored to have told his challenger to stand on his throat and point at the WrestleMania sign. This not only solidified Femi as the ‘Next Big Thing’, but it also helped make the moment more impactful. Lesnar has not dominated Femi one time in their encounters, which is very different from all of Lesnar’s previous opponents. Typically, it’s either very one-sided with The Beast dominating his opponent, or they both trade victories.
Nobody has looked this strong since Lesnar in 2002. The Beast would come in and destroy all of his opponents. Lesnar was a freak of nature, as he quickly moved up into the main event title scene. He won King of the Ring and defeated The Rock at the 2002 SummerSlam PLE to become the youngest WWE Champion in WWE history. For twenty-five years, Lesnar has been portrayed as this immovable object. That was until The Ruler answered his challenge and dropped Lesnar like he was nothing.
On Night Two, if Femi really does beat Lesnar, he will take his place on the throne. This could truly be a passing of the torch moment, as perhaps Lesnar’s days in the WWE are numbered. There’s a lot of speculation that he may have his retirement match at this year’s SummerSlam PLE. Femi could use this opportunity as a huge stepping stone to the main event title scene, where ‘The Ruler’ truly belongs.
Chairshot Radio Network
Launched in 2017, the Chairshot Radio Network presents you with the best in sports, entertainment, and sports entertainment. Wrestling and wrestling crossover podcasts + the most interesting content + the most engaging hosts = the most entertaining podcasts you’ll find!
MONDAY - Bandwagon Nerds (entertainment & popular culture)
TUESDAY - 4 Corners Podcast (sports)
WEDNESDAY - The Greg DeMarco Show (wrestling)
THURSDAY - Nefarious Means
FRIDAY - DWI Podcast (Drunk Wrestling Intellect)
SATURDAY - The Mindless Wrestling Podcast
SUNDAY - 30 Mindless Minutes
CHAIRSHOT RADIO NETWORK PODCAST SPECIALS
Attitude Of Aggression Podcast: The Big Five Project (chronologically exploring WWE's PPV/PLE history) Unidentified History (Ufology) & Game Gone Wrong (Game of Thrones Universe)
Chairshot Radio Network Your home for the hardest hitting podcasts... Sports, Entertainment and Sports Entertainment!
Powered by RedCircle
Let us know what you think on social media @ChairshotMedia and always remember to use the hashtag #UseYourHead!
-
Headline News6 days ago
Dark Side of the Ring season seven to premiere July 7 with three-part TNA/Jeff Jarrett episode
-
News7 days ago
WWE Backlash 2026 Sees Strong Advance in Tampa, But Fans Spar Over Ticket Prices
-
Indy Wrestling News4 days ago
BTS Attends CMLL at Arena Mexico as Místico Wears BTS Jacket
-
Results4 days agoMitchell’s WWE Backlash Results & Report! (5/9/26)


