#1 Sting vs The Undertaker
This one is by far the biggest WWE dream match to have never taken place and despite fans coming very close to witnessing a clash between the two legends, this dream match would eventually never go on to occur. In 2014, the biggest WCW homegrown superstar of all time, former WCW World Champion Sting finally made his much-awaited WWE debut after all these years and eventually became the biggest WCW superstar to make the jump to Vince McMahon’s company.
Following his debut at Survivor Series, 2014, Sting was initially booked into a feud against Authority leader Triple H at WrestleMania 31, however, fans were instead hoping for a match between the legendary Undertaker finally going toe-to-toe with Sting at The Grandest Stage of Them All.
But, unfortunately, the entire wrestling fanbase never really had the chance to witness two of the biggest icons share the ring with each other on the big stage, as Sting eventually announced his retirement from in-ring competition after losing his World Title match against Seth Rollins in 2015.