Event: Wrestlemania 14
It doesn't get any bigger or better than Undertaker and Kane. Well at least it didn't used to. Wrestlemania 14 was not only the rise of the Austin Era but it was the beginning of the pathway of destruction of The Big Red Machine, Kane.
Kane debuted at Bad Blood '97 costing Undertaker the first ever Hell In A Cell match and after weeks of relentless attacks at the hands of Kane, Undertaker finally accepted Kane's challenge to a match at Mania. (Only in the WWF will you see a supernatural family dispute being settled in a wrestling match.) Undertaker at that time was the force of the WWE. He was the biggest and baddest superstar in the WWF and yet Kane just dominated Undertaker at Mania. I don't think Kane was lying down for more than 3 seconds the entire match. Taker chokeslams, Kane sits up, Taker tombstone, Kane sits up, it was like Undertaker had finally met a power far greater than his own which proved to be true because Kane overpowered Undertaker so many times during that match. It was the one and only match where you will ever see Undertaker as a normal man just trying to survive the thing. After 3 tombstones Undertaker finally, finally pinned Kane. However, Kane actually kicked out even after the third tombstone but the ref counted to 3 and the match was over but Kane's dominance was just beginning.
What was unusual about Kane vs Taker Mania 14 was that I actually believed Kane's entire no-sell in the match. I still do and that is why this match is the greatest match in Kane's career imo.