The Undertaker and Sting were two of the biggest wrestling stars in the 90s, yet they never faced each other in the ring. And likely they never will, outside the theatre of the mind.

Mark Caloway (Undertaker) was asked about this recently, and said that a match between them could never hope to live up to fan expectations. And it's too late for it to happen anyway, as the years have taken their toll on him and he's not the same as he was twenty years ago. The same could probably be said for Sting.

However, let us imagine scenarios where both Sting and the Undertaker are in their prime and at their best. Say, at various periods between 1990 and 2003.

Early Undertaker from early 90's vs. blond face-painted Sting.

Attitude Era Undertaker (from when Kane showed up and all) vs. 'Crow' Sting (from the WCW vs. NWO era).

What would these matches be like? Who would win, and how?