#1 The Undertaker vs Sting
The Undertaker and Sting were two of the scariest wrestlers in WWE and WCW, respectively. The Deadman was WWE’s definition of fear, while The Icon was the face of WCW.
When Vince McMahon bought his rival company, fans expected Sting to join WWE and work against the likes of The Undertaker and more. However, it didn’t happen and the WCW megastar joined TNA instead.
We never thought Sting would work for WWE but when he made his debut in 2014, fans were hopeful that he would face The Undertaker. Instead, we got to see his rivalry with Triple H where he lost. It’s been over five years since Sting retired and there’s no way he would return to the ring again, considering his neck injury is severe.
However, we should note that Undertaker vs Sting was always planned but McMahon, in particular, wasn’t invested in this bout. He never thought that this match would draw attention so he never booked it for a show.