Just saw the first HBK-Taker match on Netflix...and it was epic to say the least. Def one of the greatest matches of all time.
How would you rank the streak matches from his first win to the last one in HITC with HHH
The Streak
The Streak
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The Streak

Justice
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Only in the last 8-10 years has WWE really began to put an emphasis on it. His last 7 matches have, in some order, probably been the top 7 with maybe the Orton match bumping edging ahead of the Batista match. But a lot of the first 10-12 were not particularly good matches.
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To fairly rank them I'd probably have to spend the day watching all the matches, which I am not up for right now, but I for the most part agree with safi that the more recent matches have been the best. The very early ones were squashes or just poor, and many of the others were very one sided.
One exception to this IMO was Undertaker vs Kane the first time around at WM 14. It drug out a bit early on but it's worth watching especially if you've never seen it. You couldn't look any stronger in a loss than Kane did there.
Another one that is memorable at least was the following year, Undertaker vs Big Boss Man at WM 15, mostly because of what happened post match but the match itself wasn't bad either, not a classic but Boss Man does get some offense in, not as one sided as some of the others, despite the dead crowd it's another one at least worth seeing if you haven't before.
Those two, the last seven (Batista, Edge, HBK x2, HHH x2, CM Punk) and Randy Orton would be in some order my top 10. Some of the others weren't all bad if you don't mind seeing Undertaker dominate, like Ric Flair and HHH the first time, those are at least no where near the terrible level of the King Kong Bundy and Giant Gonzalez matches.
One exception to this IMO was Undertaker vs Kane the first time around at WM 14. It drug out a bit early on but it's worth watching especially if you've never seen it. You couldn't look any stronger in a loss than Kane did there.
Another one that is memorable at least was the following year, Undertaker vs Big Boss Man at WM 15, mostly because of what happened post match but the match itself wasn't bad either, not a classic but Boss Man does get some offense in, not as one sided as some of the others, despite the dead crowd it's another one at least worth seeing if you haven't before.
Those two, the last seven (Batista, Edge, HBK x2, HHH x2, CM Punk) and Randy Orton would be in some order my top 10. Some of the others weren't all bad if you don't mind seeing Undertaker dominate, like Ric Flair and HHH the first time, those are at least no where near the terrible level of the King Kong Bundy and Giant Gonzalez matches.