The Icon spent his prime wrestling years in the WCW promotion, while Undertaker has spent three decades in WWE. After WCW was bought out, Sting chose not to sign with Vince McMahon's promotion - instead signing with TNA.
Sting would finally sign with WWE in 2014, but he only wrestled a handful of matches before a neck injury forced him to retire in 2016. With that, fans had to accept that Sting vs. Undertaker was never going to happen.
Or could it?
On their official Twitter page, WWE teased a potential Sting vs. Undertaker match, with the caption "Imagine...".
Even though he had to hang up the boots three years ago, Sting doesn't seem fully intent on staying devoted to retirement. When asked about the possibility of wrestling again at Starrcast, The Vigilante said he would do it for "the right price."
Not only that, but Sting also said in an interview Wrestling Travel that he would only come out of retirement to face Undertaker. In regards to facing The Phenom, Sting said they could "never get it together to make it happen," although he emphasized that he had no problem going up against Triple H at WrestleMania 31 instead.
Sting suffered a neck injury during a match against Seth Rollins at the 2015 Night of Champions pay-per-view. That's what forced him to retire, but at his Hall of Fame induction, Sting hinted at a return when he said "See you later." So who knows? Maybe the dream match could actually happen one day.
What This Means
Undertaker is still going strong in the ring at the age of 54, and Sting has had three years to rest and recover from his injuries. It's not all that crazy to think that he could come back for the one more match, but at the end of the day, Vince and WWE officials will make the final call. For now, we can only sit back and "imagine" what could have been.