#1 Triple H vs. Cactus Jack - Street Fight (Royal Rumble 2000)
The best...ever.
It defined a generation and is often touted as one of the greatest matches to have ever taken place in a WWE ring. The greatest match in Triple H's career was the street fight at Royal Rumble 2000 against Cactus Jack/Mick Foley.
Up until this point, some doubted Paul Levesque as a 'credible' world champion. After this match, 'Triple H' was an established Superstar and made him a main eventer. The hardcore bumps, the intricate technical work, the hard-hitting offense. It all came together beautifully and created one of the greatest wrestling matches of all time and, arguably, the best non-Rumble match in the history of the PPV.
Triple H got a huge gash that caused blood to continuously trickle out of him for the majority of the match but the image of him rolling in his own blood to try and keep a desperate hold onto the gold made it all the sweeter. Foley cannot be forgotten as it would have been nowhere near as good without him either -- he knew exactly what they had to do in order for the matchup to work.
Of all matches on this list, this is the most must-see. It was on this night that the 'King of Kings' as we know him was born.