The Undertaker and Triple H are the final two men still competing from their era of wrestling and throughout their time in the business, they have competed countless times. They have been amazing rivals throughout their WWE careers, constantly battling in some epic matches.
Whether it be for titles or pride, with stipulations or just straight wrestling these two men have had tons of encounters. While many of their matches are classics, not every single one of them has delivered.
10 Best: The Undertaker vs Triple H (SmackDown, 2008)
A rare high-quality main event between Triple H and The Undertaker took place on a 2008 edition of SmackDown. Of course, considering it was a television episode, there wasn't a clean finish given here with Big Show playing a part in this.
However, they still got nearly 15 minutes to work and that's more than enough for two people of their caliber to put on a tremendous bout. It's a great match where they went back and forth in what was a competitive and enjoyable clash.
9 Worst: Triple H vs The Undertaker (SuperShowDown 2018)
This was the final singles match that the two men had against each other, and sadly it wasn't the best. At this point in their careers, both men were far past their best and nobody was seeking another singles match between them.
However, WWE decided to make it happen anyway and while the no disqualification stipulation did help them, it didn't save the slow-pace and the fact they both just looked tired running a match this long.
8 Best: Triple H vs The Undertaker (WrestleMania XXVII)
Straight after Shawn Michaels had two classics at WrestleMania with The Undertaker, Triple H stepped up. Trying to get the job done that his friend couldn't, the story wrote itself for this match and they told it perfectly.
They are two fantastic storytellers who really know how to work a crowd and that's what this match did. With the No Holds Barred stipulation being added in, the match was incredibly violent and it showcased how desperate they were to win, which drew the audience in perfectly.
7 Worst: Triple H vs The Undertaker (SmackDown, 2000)
With less than 10 minutes to compete, this one was never going to be groundbreaking. The two men battled in a no disqualification match and of course, that meant that there was plenty of antics involved.
This could have been a great match if WWE had really committed a lot of time to the situation, this could have been something special. However, WWE clearly didn't want to give too much away on free television.
6 Best: Triple H vs The Undertaker (Insurrextion, 2002)
While this match was obviously doesn't get the hype that their other encounters do, simply because it's on a much smaller PPV, that doesn't mean it's not a great match. The two men put on a clinic in front of a red hot British crowd for this one, making for a really exciting match.
It's an excellent match that showcases just how good each man is. It's worth digging out and reliving on the WWE Network as they tell a great story and it isn't as long and drawn out as many of their other encounters.
5 Worst: The Undertaker vs Triple H (SmackDown, 2001)
Just one year removed from their first SmackDown clash, the two top stars competed again and once more, WWE added a big stipulation to proceedings. This time, the match was a No Holds Barred contest.
However, considering how good their WrestleMania match in this stipulation was, this one was a really poor comparison, making it one of their weaker matches.
4 Best: The Undertaker vs Triple H (WrestleMania X-7)
This is the WrestleMania match that gets massively overlooked when it comes to The Undertaker's streak as it really is fantastic. Fans only think of his later matches with Triple H, which are both very good as well, but this one is just as good and worthy of being in the conversation.
Both men were much younger here than their later encounters and that allowed this to have a much faster pace as the duo really went to battle. It was a very physical encounter with some brilliant near falls, which made this match one of their greatest.
3 Worst: The Undertaker vs Triple H (Raw, 1999)
Having two men of this star power competing in a World Championship match Monday Night Raw isn't something that happens all the time. However, in the Attitude Era, big matches like this were certainly more commonplace.
However, while it was great to see two big stars competing, the match didn't even last seven minutes and ended with a disqualification, which helped make this one forgettable.
2 Best: The Undertaker vs Triple H (WrestleMania XVIII)
While Bret Hart might have infamously given this match a 4/10, the fact is that this Hell in a Cell is an excellent encounter. It is storytelling at its absolute best with four years worth of stories across each WrestleMania all coming to a head in this one.
The Undertaker and Triple H brought everything to this match which was physical and emotional. Shawn Michaels' storytelling through his facials were amazing throughout as well, really adding to the drama of the entire match.
1 Worst: Triple H vs The Undertaker (King Of The Ring, 2002)
A major world title match between two of WWE's biggest stars at this stage in their careers should have been amazing to watch. However, that didn't end up taking place as this match was just far too slow. While they do work a methodical pace, this one was on another level of slow.
Things were then made even worse by how overbooked this entire match was. The match has issues going on in the back and The Rock and Brock Lesnar were both around referee bumps all adding to the drama. However, rather than adding to the match, it actually took away and hurt the overall quality of this encounter.