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MID-Tier Match Reviews: A Collection of UNDERTAKER Matches

By Alex Podgorski on 9 November 2026

The Undertaker is a true wrestling legend, a mythical figure with a thirty-year career and millions upon millions of fans worldwide. Growing up I was an enormous fan of his since I loved watching him do things that someone his size shouldn’t be capable of. That seems to be a common enough opinion as many other fans and a lot of his industry peers have expressed similar statements about him in interviews over the decades.

Unfortunately, despite his political power backstage, Undertaker wasn’t always given complete freedom over his opponents and thus found himself facing questionable opponents over the years.

Before we get to this random collection, let’s get a few noted matches out of the way. Undertaker’s two WrestleMania matches with Shawn Michaels still hold up as two of the greatest bouts you’ll ever see. Their Hell in a Cell match in 1997 remains the single greatest iteration of that stipulation, bar none. His singles bout with Kurt Angle at No Way Out 2006 remains my personal favorite Undertaker match and an undeniable 5-Star classic. Undertaker/Mankind remains an instant classic despite its emphasis on shock value. His WrestleMania 21 match with Randy Orton is a sleeper hit and one of the best midcard matches in modern times. At the same time, poor Undertaker has been involved in many stinkers as well as myself and the other Blog writers have noted over the years. With that, let’s take a look at five random Undertaker matches to see how well they hold up.

The Undertaker vs. Heidenreich – WWE Survivor Series 2004

The Story: Back in 2004 Heidenreich was Paul Heyman’s next attempt at destroying The Undertaker after The Dudleys failed to so the job. Heidenreich was portrayed as a legit psychopath, coming out wearing a straightjacket and even attacked random fans in attendance (read: plants). Eventually Heidenreich decided to get directly involved With Undertaker’s business by attacking him during his WWE Title match at No Mercy and, once the match ended, he drove his car into the hearse containing The Undertaker. When GM Theodore Long told him that there was actually no one inside that car, Heidenreich showed a modicum of concern knowing that the supernatural Undertaker was now out to get him.

The Match: Heidenreich attempts a cheap-shot but ‘Taker out-strikes him and scares the referee out of the ring. Heidenreich blocks a corner charge but runs into a boot. ‘Taker drops elbows for a one-count and drives Heidenreich into a corner arm-first. ‘Taker works the arm and attempts Old School but Paul Heyman distracts the ref so that Heidenreich can land a low blow. Heidenreich pulls ‘Taker into the post and then we get some ringside brawling which allows ‘Taker to rally back and land the apron leg drop. He followed with Old School and a Complete Shot for two. Heidenreich dodges a corner boot and tackles ‘Taker off the apron. He follows with strike barrages and a chinlock but Heidenreich answers with a clothesline. Heidenreich hits another clothesline but then ‘Taker counters a suplex with his own. Heidenreich blocks a back body drop with a kick but ‘Taker stiffens and stares daggers at him. ‘Taker hotshots him and hits a top-rope clothesline followed by his full comeback sequence for two. Heidenreich blocks a Chokeslam and counters a charge with a swinging side slam for two. Heidenreich hammers ‘Taker with punches until ‘Taker counters with a Last ride for two. ‘Taker counters a sleeper with a back suplex and then sits up. ‘Taker follows with a flying clothesline, a Chokeslam, and a Tombstone Piledriver for an easy three-count.

Winner after 15:53: The Undertaker

You can watch the full match here.

Review: Dave Meltzer gave this only * which I think is a slight bit too harsh. Yes it was slow, plodding, overlong, and better suited for free TV than on a Big Four PPV. But it wasn’t as offensive as some commentators have noted. Heidenreich had no chance of winning and was boring on offense while Undertaker had to work a little bit harder than usual to put him down. It was a carbon copy of one of the many Undertaker-versus-random-monster/big-guy-threat that defined most of his career but just because it was something we’ve all seen before doesn’t mean it was a disaster. That said, this should not have been on PPV unless Heidenreich had shown significantly more improvement and developed a more powerful arsenal to add to his credibility against a wrestler literally shown to have supernatural powers. As it stands, though, this match is neither good nor bad, just forgettable.

Final Rating: **

TLC Match for the vacant World Heavyweight Championship: The Undertaker vs. Edge – WWE One Night Stand 2008

The Story: This was the next chapter in a year-long story that saw Edge constantly interfere in Undertaker’s world title matches. This rivalry peaked at WrestleMania XXIV where Undertaker beat Edge in a certified classic to win the WHC for the second time and extend his Streak to 16-0. Edge failed to regain the title at Backlash and in that match Undertaker got so mad at him he locked in his Hell’s Gate submission hold for so long he allegedly caused Edge serious injuries. In response, then-SmackDown General Manager Vickie Guerrero – who was in an on-screen relationship with Edge – stripped ‘Taker of his title, citing the danger of the Hell’s Gate submission and booked this match to crown a new champion. Additionally, if Undertaker didn’t win, he would be forced to leave WWE.

The Match: ‘Taker hits first with a boot and gets comfortable enough to land Old School without resistance. Before he can bring a ladder into the match Edge dropkicks it into his face. Nearby, Edge sets one table atop another, telegraphing what’s going to happen later. ‘Taker drops him with the ladder and sets up two more, so now we know how the match will end. Edge drop toeholds ‘Taker into the steps and climbs the ladder for the title, only to be dropped onto the top rope. ‘Taker attempt to Snake Eyes Edge onto the ladder but Edge escapes and drives ‘Taker into it face-first. Two more ladders get introduced, one to climb and one to create another face-ladder connection. ‘Taker manages to create a ladder-assisted Snake Eyes/big boot combo and lands some chair-shots, but then Edge uses that chair to block ‘Taker’s apron leg drop. Edge attacks a leg and blocks a Last Ride into a ladder with a low blow. He follows with chair-shots and a splash from a ringside commentary table through a normal table close by.

‘Taker manages to pull Edge off a ladder but eats a spear for doing so. Edge follows with a ladder-assisted con-chair-to on ‘Taker’s leg. Then he introduces a much bigger ladder and lands more chair-shots. He attempts a con-chair-to to the head but ‘Taker strikes first with a low blow. Then ‘Taker Chokeslams Edge through a ladder bridge between the ring and barricade. ‘Taker climbs the giant ladder but here come Curt Hawkins and Zack Ryder to interfere. They setup a table sandwich but ‘Taker escapes and Chokeslams Ryder from the top rope through a tables below and Chokeslams Ryder from the apron through a different table. Edge capitalizes with a spear that sends ‘Taker from the apron to the floor. ‘Taker recovers and hits a Last Ride through two tables. ‘Taker climbs again but here come Chavo Guerrero and Bam Kneely to interfere with chairs. He makes quick work of them and then, for pretty obvious yet dumb reasons, repositions the giant ladder further from the title. Edge reemerges and pushes the ladder aside, sending ‘Taker crashing through only two of those four ringside tables. This allows Edge to easily climb the ladder and claim the title, leaving Undertaker banished from WWE.

Winner and NEW World Heavyweight Champion after 23:26: Edge

You can watch the full match here.

Review: This match, along with their HIAC at SummerSlam, are two reasons why I stopped liking Edge for a very long time. It was one of the most contrived, plodding, telegraphed, and over-rated main-events in SmackDown history. They leaned as far into the TLC stipulation as possible but in the process made it too slow and setup-heavy with obvious hardcore spots that, outside of a small handful, weren’t justified. Edge spent more time setting up a convoluted table spot that, despite having a solid payoff, was a foregone conclusion from the moment he started working on it. Clearly, he was trying to conjure up memories of TLC II but failed for a number of reasons. First, TLC II was fast-paced while this match dragged. Second, all the interference in that match served some purpose while here the involvement of Chavo and Kneely made no difference. Third, there was still wrestling mixed among the crazy high-spots in TLC while here the non-weapons portions were reduced to precious little. They had a decent story going with Edge working the leg and, of course, the stipulation led to massive heat, but the match itself was just dumb at times. Unfortunately, this match exposed Edge’s shortcomings as a wrestler and highlighted his overreliance on hardcore stipulations. Forget being a glorified tag team wrestler; Edge became a glorified hardcore wrestler who couldn’t stop using tables, ladders, or chairs if you paid him.

Final Rating: **3/4

Ladder match for the WWE Undisputed World Heavyweight Championship: The Undertaker [c] vs. Jeff Hardy – RAW, #475, July 1, 2002

The Story: Undertaker was still in his Big Evil bully story and set his sights on the Hardys. At the time WWE decided that the Hardys had rune their course as a tag team and experimented with putting them in singles positions. Jeff, who was smaller and more reckless, was naturally suited as an underdog who could take a shitkicking. So WWE decided to book him in an unlikely, almost impossible situation: defeat Undertaker for the WWE title despite being about 100 pounds lighter and having no major singles achievements to speak of.

The Match: Hardy toys with ‘Taker by touching his motorcycle during entrances and uses that distraction to dropkick a ladder into him. ‘Taker uses his power to overwhelm Hardy and pummels him until Hardy reverses getting thrown into a ladder. Hardy follows with a leg drop onto a ladder onto ‘Taker but moments later ‘Taker smashes it back into Hardy and then smashes it into him with enough force to send him flying off the apron. ‘Taker pretty much has the match won but then opts to punish Hardy more. Hardy tries fighting back but ‘Taker blasts him with a right hand and does the apron leg drop with Hardy trapped inside a ladder. Taker misses a corner clothesline into a ladder and moments later Hardy counters a corner whip with a Whisper In The Wind. ‘Taker hits back but then eats a low blow and a ladder-assisted suicide dive from the ring to the floor. Hardy unveils the big ladder and starts climbing. ‘Taker cuts him off and attempts The Last Ride. Hardy counters with a Frankensteiner that sends ‘Taker to the floor. Everyone’s going nuts. Hardy makes it to the top but ‘Taker returns with a chair. ‘Taker attempts The Last Ride again. Hardy counters with chair-shots to the head. Monster pop for that. JR gives a classic line: “CLIMB THE LADDER, KID! MAKE YOURSELF FAMOUS!” Taker cuts him off again and Chokeslams him off the ladder to easily reclaim his title.

Winner and STILL WWE Undisputed World Heavyweight Champion after 14:05: The Undertaker

You can watch the full match here.

Post-match, ‘Taker sees Hardy still moving so he plants him with a successful Last Ride. ‘Taker makes it to the top of the entrance ramp when Hardy grabs a microphone and, with a breaking voice, states he hasn’t been broken. ‘Taker makes a beeline for him, pulls him to his feet, teases a punch…and raises his hand. There’s Undertaker’s face turn.

Review: Few RAW matches better capture the bully/underdog dynamic better than this. Few people expected Jeff Hardy of all people to win yet those ladder climbs were magical. For a brief moment the unthinkable became believable and everyone watching was collectively hypnotized into believe this fairy tale could actually come true (Big thanks to Jim Ross and Jerry Lawler calling the moment the way they did, playing off each other and creating a special moment). No one expected a competitive match so when Hardy surprised Undertaker and landed big hits he escaped squash match territory and fought to survive. But let’s be real: by no means was this a classic as the match was highly one-sided and Hardy’s offense mostly consisted of sudden surprises. I suspect that this was a clever way of turning Undertaker face while maintaining his mean ass-kicking biker gimmick. Still as far as RAW main-events go, this is a good one, especially since it ddidn’t drag and Hardy did an excellent job of selling this as a frantic situation he stood no chance of winning.

Final Rating: ***1/4

The Undertaker vs. Brock Lesnar – WWE Hell in a Cell 2015

The Story: This was the culmination of a year-and-a-half-long feud going back to WrestleMania XXX when Lesnar ended The Streak. ‘Taker disappeared for a year and returned for ‘Mania 31 and wrestled a forgettable match with Bray Wyatt. A few months later ‘Taker made a surprise return to cost Lesnar the world title. The two men met at SummerSlam 2015 but their match had a controversial finish involving low blows, a tap-out, a distracted referee, and mistimed bell ringing. To resolve this feud once and for all, a rematch was booked for HIAC 2015.

The Match: They start off tensely and with a few quick strikes. Lesnar lands some shoulders to the gut but ‘Taker retaliates with a corner clothesline. Lesnar attempts a German Suplex but ‘Taker dumps him ringside. They brawl around the ring and then ‘Taker sends Lesnar into a ringpost…sort of. Lesnar gets his hand up yet seconds later he’s bleeding. More brawling. ‘Taker shoves Lesnar back into the ring but Lesnar double-legs him. Lesnar lands some chair-shots but then the ref orders him to stop so that the doctor can tend to his wound. Crowd boos loudly. Lesnar lands more stiff chair-shots and launches ‘Taker into the cell. He removes one of his gloves leading to some bare-knuckle punches but then ‘Taker counters a ringside suplex with his own. Now both men are bleeding. ‘Taker lands a chair guillotine for a two-count. He attacks the wound some more but Lesnar answers with a German Suplex. He lands two more followed by an F-5 for two. The doctor re-emerges but Lesnar shoves him aside which gets a NUCLEAR pop from the crowd. He lands a second F-5 but only gets two so he uses the steps as a weapon for another near-fall. ‘Taker blocks another steps-shot and locks in the Hell’s Gate. Lesnar fights out and starts ripping apart the ring canvas. ‘Taker sits up as Lesnar pulls off some protective padding and Chokeslams Lesnar onto the exposed wood followed by a Tombstone onto the same for a near-fall. ‘Taker does the throat slash gesture but opens himself up to a low blow. Lesnar follows that with another F-5 onto the same exposed spot for the pin and the win.

Winner after 18:07: Brock Lesnar

You can watch the full match here.

Review: That was better than expected though, again, a bit underwhelming as well. It had that monster mash vibe as both guys threw all they had at each other with wanton disregard for safety and protocol. That specific aspect was the highlight of this match: when a doctor came in to clean up blood from Lesnar’s forehead Lesnar threw him aside and the crowd loved him for it. See, that’s why Lesnar had such a special aura: he was able to get away with violating WWE’s rigid rules while a different wrestler would’ve been forced to sit there and let the process continue else he face some consequence. As for Undertaker, he stuck to playing the hits and attacking Lesnar’s open wound which, again, came about somewhat awkwardly. While they brought the hate and appeared to throw live rounds at times, the HIAC stipulation felt a bit underutilized. The best came from Lesnar, whose style and intentionally clunky execution of some moves added to his sense of malice. While not the bloodiest or most shocking of Cell matches, it was entertaining and had a few nice surprises with the canvas ripping spot that put an emphatic end to one of WWE’s most heated rivalries.

Final Rating: ***1/2

World Heavyweight Championship Match: Kurt Angle [c] vs. The Undertaker, SmackDown #342, March 3, 2006

The Story: A few weeks earlier at No Way Out, Angle retained his World Heavyweight Championship against Undertaker in one of the greatest pro wrestling matches you will ever see. It was the closest thing to answering the question of what would happen if you threw WWE wrestlers with 1990s King’s Road All Japan into a blender. That match ended somewhat controversially (at least from Undertaker’s perspective) since Angle won with a flash pin and not something truly emphatic or decisive. Undertaker, being who he is, demanded a rematch and got it, because no authority figure is dumb enough to tell him “No”.

The Match: They trade strikes in different corners until Angle counters a charge with an armdrag. This turns into a chain wrestling sequence and an exchange of armlocks which ends with ‘Taker’s elevated arm wrench. ‘Taker overpowers Angle but Angle prevents Old School. Angle attacks persistently but ‘Taker counters with an arm wringer. Angle counters again and lands corner punches which ‘Taler turns into a Last Ride attempt but instead dumps Angle on the ropes. That leads to ringside brawling and ‘Taker landing an enzui version of his apron leg drop. Back in the ring ‘Taker grinds his forearm into Angle’s neck and targets it extensively. Angle counters with an overhead suplex for two and applies a grounded headlock. He gets two off a snap suplex and locks in a bodyscissor but ‘taker powers out and mounts him with punches. Angle dodges a corner boot and charges to knock him off the apron but ‘Taker punches him first. A corner struggle ends with a top-rope Superplex that gets Angle a two-count.

After a commercial break we find angle working a resthold. Angle clotheslines ’Taker ringside and reverses a whip into the ringsteps. That leads to a strike exchange in the ring that ends with a corner clothesline from ‘Taker. He attempts his usual combo but Angle ducks a big boot and lands a German Suplex.  ‘Taker avoids an Angle Slam and lands a big boot for two. ‘Taker goes for a Chokeslam. Angle counters with a victory roll into an Ankle Lock. ‘Taker kicks free and they trade Tombstone attempts. Angle counters into an Angle Slam for two. ‘Taker rolls out of an Ankle Lock and lands a Chokeslam. Angle plays possum and catches ‘Taker with another Ankle Lock. ‘Taker reverses into the triangle choke. Angle does the same jackknife cover that won him their match at no Way Out but this time ‘Taker avoids the pin using slight adjustments. Angle gets a ropebreak with his foot so ‘Taker goes for a leg drop. Angle catches his foot and reapplies the Ankle Lock. ‘Taker escapes and counters an Angle Slam with a Dragon Sleeper. Angle counters with a DDT for two. Angle misses a Moonsault. ‘Taker capitalizes with a Tombstone Piledriver and covers but here comes Mark Henry to interfere for the disqualification.

Winner and due to disqualification after 28:22: The Undertaker (Kurt Angle remains Champion)

You can watch the full match here.

Review: While there was no way these two could top their No Way Out match on free TV they delivered a PPV-quality contest nonetheless. These two had great chemistry and brought their working boots on this night. It wasn’t particularly novel as far as story or match content was concerned, save for ‘Taker overcoming the same pin that cost him that earlier match. The inference was, unfortunately, expected since WWE had an institutional allergy to clean finishes on TV, especially between babyfaces and other plans for WrestleMania in the cards. Yet despite being a repetition of something we’ve already seen before, these two just clicked together and were able to put on compelling contests without the need for gimmicks, overt theatrics, special stipulations, or extra tools or implements. Definitely one of the best matches in SmackDown history and a prime reason both these men are still so widely revered.

Final Rating: ****1/4

As always, thanks for reading.

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