I think Undertaker has had more 4-star plus matches than Triple H in the last 5 - 7 years because Hunter slowed down during the same time and Undertaker peaked around that period.
From a general perspective, there are segments of fans who consider the Orton series and Batista series for Undertaker as "classics," but when we talk about the general consensus, people remember those series for the great matches, but not neccesarily in the same breath as Undertaker's classics against Angle, Michaels, and Triple H. In fact, the Hell in a Cell match against Edge is considered a classic by majority of the fans and is the closest that comes to the matches against Angle/Michaels/Hunter. Generally of course. I'm not big on the Orton matches, but I generally adore the Batista matches. As being somebody who didn't think highly of the entire Edge series, I've come to love the main event of WrestleMania XXIV and it's one of the best main events for me.
I think the "classic" matches of Undertaker and Triple H from 2005 are--and I'm only including 5-star and **** 3/4 matches here:
- No Way Out 2006 vs. Kurt Angle ~ **** 3/4
- WrestleMania XXV vs. Shawn Michaels ~ **** 3/4
- WrestleMania XXVI vs. Shawn Michaels ~ ***** (Undertaker's best match ever)
- WrestleMania XXVII vs. Triple H ~ *****
- WrestleMania XXVIII vs. Triple H ~ **** 3/4
- Vengeance 2005 vs. Batista ~ **** 3/4
- Taboo Tuesday 2005 vs. Flair ~ **** 3/4 (I LOVE this match!)
- WrestleMania XXVII vs. the Undertaker ~ *****
- WrestleMania XXVIII vs. the Undertaker ~ **** 3/4
Even when you look here, if we erase the year 2005, from 2006 onwards Hunter's only classics are against Undertaker, which obviously indicates a trend for both wrestlers. That doesn't mean Triple H hasn't had some spectacular matches, but it suggests that Undertaker has been spectacularly dominant in this period. While there are four matches against DX in the list, Undertaker has been in a magnificent run since 2006.
@ Clique Yes, those matches... I can't remember all of 'em of course.