WWE Undertaker’s Deadliest Matches DVD Review

The Undertaker, arguably the most enduring wrestling character in the history of the business, has had more match types associated with him than any other wrestler, so it seems fitting that a DVD set honouring those has been put together. The main problem is that because of his current persona, the BikerTaker period of his career is overlooked, which is a shame because, for me, the “Big Evil” phase of that portion was the best work Undertaker had ever done.


Certificate: 18

Running Time: 499mins (8hrs 19mins)

Discs: 3

Disc 1


  • Two Decades of Destruction
  • Body Bag Match: Undertaker v Ultimate Warrior – Madison Square Garden (July 1, 1991)
  • Custom Made Coffin
  • Coffin Match: Undertaker v Kamala – Survivor Series (November 25, 1992)
  • Grim Reaper
  • Casket Match: Undertaker v Kama – SummerSlam (August 27, 1995)
  • Shadow of Death
  • Casket Match: Undertaker v King Mabel – In Your House (December 17, 1995)
  • Deranged and Sadistic
  • Undertaker v Mankind – King of the Ring (June 23, 1996)
  • No Boundaries
  • Boiler Room Brawl: Undertaker v Mankind – SummerSlam (August 18, 1996)
  • Chilling Numbers
  • Buried Alive Match: Stone Cold Steve Austin v Undertaker – Rock Bottom (December 13, 1998)
  • Internal Fires
  • Inferno Match: Undertaker v Kane – RAW (February 22, 1999)

Disc 2


  • An Imposing Force
  • Undertaker v Big Show – RAW (May 3, 1999)
  • What Lies Beneath
  • WWE Championship Match: Undertaker v Big Show – RAW (June 7, 1999)
  • A Long and Complex History
  • Concrete Crypt Match: Undertaker v The Dudleys – Great American Bash (June 27, 2004)
  • Devils and Wicked Men
  • Casket Match: Undertaker v Heidenreich – Royal Rumble (January 30, 2005)
  • Like Father, Like Son
  • 1st Ever Handicap Casket Match: Undertaker v Randy Orton & “Cowboy” Bob Orton – No Mercy (October 9, 2005)
  • The Devil’s Playground
  • Hell in a Cell: Undertaker v Randy Orton – Armageddon (December 18, 2005)
  • Last Judgment
  • Last Man Standing Match: Undertaker v The Great Khali – SmackDown (August 18, 2006)

Disc 3

  • First Blood
  • First Blood Match: Undertaker v Mr. Kennedy – Survivor Series (November 26, 2006)
  • Last Ride
  • Last Ride Match: Undertaker v Mr. Kennedy – Armageddon (December 17, 2006)
  • Powers Lie Within
  • Last Man Standing Match for the World Heavyweight Championship: Batista v Undertaker – Backlash (April 29, 2007)
  • Revenge
  • Undertaker v Big Daddy V – SmackDown (January 25, 2008)
  • Ring of Fire
  • Hell in a Cell: Undertaker v Edge – SummerSlam (August 17, 2008)
  • State of Mind
  • Steel Cage Match: Undertaker v Big Show – SmackDown (December 5, 2008)
  • Legacy of the Phenom

Moving on from my disappointment at only the Deadman character being featured, a glance down the match listing shows a few glaring omissions, mainly his bouts with Shawn Michaels (the original HiaC and Casket Match) and THE Hell in a Cell Match with Mankind, that despite being on other DVD releases, really should have been included here to allow the title to live up to its billing.

The first disc opens with Scary-Voiceover-Man introducing the character before Undertaker himself talks about his Two Decades of Destruction. It’s a nice touch to have the man himself do the honours and he even acknowledges (very briefly) that The Undertaker character wasn’t the beginning for him.

After this, the first match is easily the least seen bout of the collection as Undertaker tangles with Ultimate Warrior in a Body Bag Match. As with most of the matches in his first few years, the strength of the gimmick compensated for the poor action inside the ring. Looking back now, it’s amazing to think how much Undertaker has evolved as an in-ring performer. Regardless, the crowd really lap it up (as I did back in the day) and the highlight is Warrior’s unbelievably awesome piledrivers. Also, the sight of Undertaker sitting up inside the body-bag is quite funny.

The three Casket Matches that follow are dull and not really worth sitting through unless you haven’t seen them before and want to absorb the complete history of the character (although, it is a nice trivia point to notice Matt and Jeff Hardy struggle to carry King Mabel during his entrance and Undertaker in his face-mask for the same bout). Things pick up, however, as soon as the deranged Mankind makes his way to WWE.

These two had amazing chemistry and every time they were on screen with each other, the viewers were in for a treat. Their first actual match has an amazing start (I’ll leave you to see it for yourself if you haven’t seen this contest already) and the difference between this Undertaker and the character we’ve seen so far is night and day. The action is fast-paced, the blows are brutal (the knee-strike to Undertaker’s face as he’s against the steel steps looks devastating and Mankind leaping from the apron to the aisle to drop an elbow is very impressive, especially for the era) and it’s literally like ‘Taker was reborn with the arrival of Mick Foley. Add in a great finish and this is one of those lost classics that people talk about, but very few actually get to see. Until now.

The same can be said for the Boiler Room Brawl; very few of today’s fans will have seen it, yet they’ll have heard people mention it over and over again. It’s an interesting idea and the way in which the opening was shot (Undertaker seeming hesitant to enter the room and then having to scour in the darkness to find Mankind) is really cool and the action going on without commentary added another unique aspect to it. Basically a backstage fight between two men, the brawl is hard-hitting but basic until they make their way to the ring (the rules state that the winner will be the first person to reach the ring and grab the urn from Paul Bearer). It’s at this point where the situation takes an interesting turn (although, seeing the other wrestlers in the hall watching as they fight towards the ring is also interesting) and the next chapter in Undertaker’s career begins.

Unfortunately for us, the beginning of this new chapter is omitted as the introduction of Kane, the heel turn and the formation of The Ministry are all overlooked as we jump to December 1998 and the rivalry with Steve Austin that had been running since just before Summerslam. The first Buried Alive Match isn’t included (which can be justified due to there being two other Mankind matches on the first disc), so if you haven’t seen it, the comments from the announcers referencing it may be lost on you. That being said, the action is as you would expect from these two and the finish is pretty damn inventive too.

Closing the first disc is an Inferno Match, but it’s not the superior PPV one, but the throwaway encounter on RAW. For me, the Inferno Match should’ve been a one-time deal. The awe of the flames carried the action as it was limited (hardly the fault of the wrestlers, to be fair) and as basic as can be. The repeat lost a lot of that awe-factor, so it’s a footnote rather than a chapter in my book.

Disc 2 opens with a match against Big Show and the first thing that strikes you is just how in shape Show is. Trim and muscular, it’s like a completely different wrestler to the guy we see today. There’s no reason for this match to be on the list. It’s not a gimmick match, it ends by DQ at only three minutes and really nothing more than an angle to set up the match immediately following it, which is also not a gimmick match, is really short and isn’t really worthy of a place on this list.

The next match is the only one on this list that I haven’t seen. I think I was moving house at the time, so didn’t have access to SKY, meaning I missed WWE for the period the angle with Heyman and Undertaker went on. The pre-match vignette makes me wish I had seen it though, as I imagine the promos from Paul E. would’ve been amazing. Having now seen it, the match itself is interesting (mainly due to Heyman), but the end is baffling and the pinnacle of WrestleCrap.

Heidenreich is a blip in the road best avoided and the Handicap Match doesn’t really deserve a place either (although the prop department deserve, um, props for the amazingly realistic Undertaker, Orton and “Cowboy” Bob dummies used during the angle), but things pick up with the first Hell in a Cell bout of the collection. Orton v Undertaker inside the Cell is stunningly brutal, with each guy hammering the other and bleeding profusely. Without a doubt, this is the match of the series so far. In all honesty, that’s not actually saying that much as outside of the Mankind and Austin matches, the bouts have been pretty much average at best.

Ending Disc 2 is a match I can remember enjoying at the time. If memory serves me, this was originally supposed to take place at Summerslam, but Vince felt Khali couldn’t be trusted to deliver on a live broadcast, so it was moved to Smackdown, but with the (alleged?) help of the editing suite, this was a really good brawl. On paper, Khali, at 7’3” and with a fantastic physique (especially for someone so large), was easily the most intimidating foe Undertaker had ever faced. Their bout at Judgment Day was decent enough and the finish, even in this era of “we know everything about the wrestling business” that we live in, caused a stunned silence to fall upon the fans. This made the LMS Match interesting because Undertaker had yet to slay the beast and Khali was being booked as invincible, so the result was up in the air. Battering each other with whatever they could grasp, I’d say this was the pinnacle of Khali’s in-ring career.

The home straight begins with two matches against Mr. Kennedy that are better than they could have been, but also have the added bonus of JBL on commentary; something that elevates even the most mundane on in-ring encounters. Mundane is one thing the rivalry with Batista cannot be accused of. This match followed on from their show-stealing encounter at WrestleMania 23. It’s hard to put into words exactly how much Batista v Undertaker exceeded our expectations unless you were there to witness it at the time. If anything, the LMS Match is even more impressive because it kept up the high standard from ‘Mania and made us eager to see the next bout in their sage. This rivalry is the perfect example of when you can have two guys fight on successive PPV events and it not be stale. This is easily my favourite bout of the set and worth the price alone.


From my favourite match in this collect to a contender for the worst is not how I like my DVD sets to run. Having already stunk up the joint when Big Daddy V was King Mabel, it’s a joke that the people who put this together felt that having a second match between the two was a good idea. The fact that it’s not even a gimmick match (see Big Show’s two from 1999) means that, even excluding BikerTaker, there are literally dozens of worthier matches that could’ve made it onto the list. The only reason I could justify having it included is that this is the match where Hell’s Gate was debuted.

Things pick up again as the Hell in a Cell gets another airing with Edge being the victim this time. Like Batista before him, Edge stole the show with Undertaker at WrestleMania (I genuinely felt it was over when Edge hit the spear and jumped from my seat when ‘Taker kicked out – even someone as “inside” as me got suckered in). This match is uber-heated, with great evolution on show from their earlier encounters, with the closing moments being a brilliant showcase of revisiting the past to close a chapter; Undertaker dishing out everything Edge had done to him over the past year was just brilliant.

Big Show appears for the third time to close us out with a Steel Cage Match on Smackdown. It’s a good match, but nothing special, with the exception of how Undertaker locks in Hell’s Gate. For me,that was an inspired piece of genius.

It’s a semi-flat end to an up-and-down selection of matches and leaves you wondering what all the fuss is about as the WWE flash-logo appears.


Twenty-one matches are on the set, but only six of them are truly great bouts. A few of the others are worth a watch, but too many of the them are dull and plodding. That being said, it is interesting to see the evolution of Undertaker over the last twenty years, but I feel this would have been a better collection had the BikerTaker gimmick also got a look in.

One aspect I did enjoy was the trip down memory lane with the announcers. Finkel doing the introductions is always great and on commentary we had, at various points, Gorilla Monsoon, Lord Alfred Hayes, Vince McMahon, Bobby Heenan, Mr. Perfect, Owen Hart, Jim Ross, Jerry Lawler, Tazz, Coach, Michael Cole and JBL. It’s quite an eclectic mix of talents and some of them (Gorilla, Vince, Heenan, JR and JBL) really add to a wrestling match, lifting a decent match to being good, a good match to being great and a great match to being epic. It’s also interesting to note that Vince wasn’t above giving non-WWE entities credit back in the day. Mentioning Sam Shepherd inventing the Mandible Claw is a departure from what he’s like now, where WWE invented everything… including Nova.

Blurring on the Attitude Era segments (of which there is very little, surprisingly) is annoying, especially for us in the UK who enjoy the Tagged Classic series where there are no blurring or muting of people saying WWF, but it’s not the kiss of death that some people have made it out to be.

It’s also nice to see some of the bouts that Undertaker lost as well. The two against Mankind and the First Blood against Kennedy really did a great job of helping a newcomer get over with the WWE fanbase, but the fact there are non-gimmick bouts included make it doubly baffling as to why Big Show and Big Daddy V were chosen to fill some of these slots when there are plenty of other non-gimmicked bouts that are more deserving of a place at the dinner table.

Speaking of Big Daddy V; him being on twice, yet HBK, The Rock and Triple H not featuring once, is a horrible decision that makes no sense. The collection was released in 2010, yet the last match is from December 2008. What happened to 2009? Daddy V gets two outings and Big Show gets three, yet a trio of fantastic opponents who had spellbinding matches against Undertaker don’t even get a sniff of action. That alone is reason enough to leave the set alone. As it is, the six great matches give it some worth, but I would recommend buying it only if you can find it at £15 or less.

A missed opportunity and the lack of extras, considering there’s close to twenty years of footage to work from, is nothing more than an insult. If you want an Undertaker DVD, I recommend This is My Yard as it’s still the pinnacle of Deadman-related releases.

Points: 5/10

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