#1 Sting

We couldn't have ended this list without the former WCW superstar and for a short time, WWE superstar as well - Sting. The Vigilante perhaps ranks as The Undertaker's greatest dream opponent - a match that should have happened years ago but never came to pass.
Sting revealed to The Daily Star in 2011 that he was offered a match against The Undertaker at WrestleMania 27 along with a WWE Hall of Fame induction (H/T WrestlingInc):
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"There are so many variables. Let's just say that I turned it down for the same reasons I always have. Something in me never trusted what would happen up there, based entirely on the track record with other WCW guys and everything that went on after Vince [McMahon] bought WCW."
It's not a surprise to see why Sting took so long to join WWE. However, Vince McMahon proclaimed that someday, they would do business together. Unfortunately, Sting's run in WWE was a bit disappointing as it only featured two major matches - a losing effort to Triple H on his WWE debut at WrestleMania 31 and a WWE title match against Seth Rollins at Night of Champions later that year in 2015 - a match that ended his career and took away the possibility of a bout with The Undertaker.
It's too late now with both Sting and The Undertaker retired and unfortunately, the dream match is going to remain a dream.
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