So apparently we're going to just forget that even though Bearer turned on Taker at Summerslam he still cost him the 1st match at King Of The Ring (both matches ended with Bearer hitting Taker over the head with the urn). At the time Mankind wasn't a big name, yeah he became one but he wasn't quite there yet in his debut. Either way it doesn't matter because they were brought in for entirely different reasons and they were different characters to boot, Cactus was brought in to put Sting and other top talent over, Mankind was brought in because WWE tried to make him a top talent. Yeah Taker lost their 1st encounter but like I said it's a completely different situation in almost every way. Also, when Sting beat Cactus it was at a time Cactus was starting to get noticed, he was alot higher on the totem pole when he got to Taker. Lastly in 96 Mankind wasn't a big star, when Taker beat the guys I mentioned they were big stars (well, except Cena).
Taker has only started to look rough when he was getting up in years, when Taker was at his peak he didn't get blown up, a 40 plus year old Sting isn't exactly an iron man and he has looked pretty damn slow for over a decade. Doesn't matter though, it's not two 40 somethings wrestling in this match anyways. I'm just saying although I've never seen Taker wrestle 60 minutes I've seen him wrestle long matches without breaking a sweat, especially in his prime. At the end of the day it's wrestling and Taker doesn't have to kill himself to make it the whole hour, especially how he works. At least when I talk about Stings flaws they are things that have been shown and proven over time, like how he has great difficulties with guys like Taker in early encounters. I love Sting but he isn't exactly Albert Einstein in the ring and he makes ALOT of mistakes, mistakes someone like Taker would undoubtedly make him pay for.
Lastly, let's ask Kevin Nash who puts on the most devestating Sharpshooter because I promise he isn't saying Sting. Also in a kayfabe sense The Undertaker is the only guy in WWE history that broke out of the Sharpshooter and actually broke the grip, I've seen more than one guy break the Scorpion Death Lock, just saying.
Putting everything aside let's just look at a prime Undertaker vs. prime Sting for a second. Taker is a guy who rarely sells I'm his prime, he's a guy that was never pinned clean until Stone Cold did it in '98, nearly EIGHT YEARS after he debut. He's a guy who could get DDT'ed on the floor by Jake Roberts (a guy who literally or figuratively put everyone else on a stretcher doing that on the floor) and he just shrugged it off and won 2 minutes later, he beat Hogan in his first title match (someone who is much bigger than Sting every was) and beat big star after big star following that. Sting on the other hand has lost an incredible amount of times for someone who was on top, he's a guy who has often been foolish in his matches to a detriment, he's often a slow learner when dealing with difficult opponents, often needing a chunk of tries to finally pull it off and unlike Taker in his prime, Sting could be beaten clean. So unless Sting is going to actually do his homework before their 1st match (something he's never really done) and is going to cheat his ass off (again, something out of character for him) then his odds are pretty damn low in pulling this off. It's great if he can blow up Taker after 30-40 minutes but he still has to pin him, make him submit or get him counted out and all 3 situations it's going to take something more than Stings arsenal to get the job done.
All in all I'm just saying Sting will probably need a few tries to figure it out and even then he's at most getting 1 or 2 falls, I have no doubt Taker could do a bit better than that even if he blows up after 40 minutes.