This is a dream match for many wrestling fans, and I count it as a great shame that we never got to see these two competitors compete in their primes. They have both been a huge inspiration to both fans and their peers over their long careers, and I have no doubt that many people in the business today are there because of these two legends. In this match however, only one can come out on top, and for this I am going to pick HBK.
The usual tactic of Shawn Michaels is to take a beating and then come back for the attempted win, and Sting is a man who would be more than happy to give that beating. However, Stings tactics very often involve his bat, and a sneak attack from a location such as the rafters. This is a standard rules match, and there arent exactly many hiding places inside a wrestling ring. This will force these two to go head to head and see who is more resilient and who is the better competitor, and I would consider this to be Shawn.
Stings main finishing maneuvers are the Scorpion Death Drop (Inverted DDT) and the Scorpion Death Lock (Sharpshooter), Shawns main finisher is Sweet Chin Music (Super kick). Over Shawns career he has become very familiar with the SDL, to the extent that he has often been able to counter it, and even applied it himself upon occasion. I do not think that Sting would be able to beat HBK by submission, considering how resilient Shawn has proven himself to be against the move in the past, most significantly against Bret Hart, who many consider to be the master of the move. As for the Scorpion Death Drop, I do not consider this to be an impressive finisher, as I think sting would be better served using a move that has more finality and does not seem so much of a mid match move. SCM is superior to both of these finishers in my opinion, as HBK mastered it over his career, and to me it has always had the feel of a match ending move when he hits it. Shawn would move on here, as a SDD would not put him out for the count, but SCM would lay out Sting.
The 45 minute time limit would not present much of a problem to either of these men in their prime, so this is not too much of an issue for me. The standard match stipulation would benefit the better competitor, who as I have stated I consider to be Shawn. This is because, while there have been better pure athletes in professional wrestling, I do not consider anyone to have mastered the nuances and become as adept in the ring as HBK. He proved his doubters wrong again and again when they said that he could not win a match or deliver a show stealing performance, and this would be another case of him being vindicated. Sting can brawl, and Sting can wrestle, but in a standard match with DQs and time limits as obstacles, there are very few people who could outmatch HBK without bringing in help or cheating in some capacity. Sting is a big part of wrestling history and deserves to have gotten far in the tournament, but I do not think he deserves to make it past Shawn in this round. HBK has recently retired and so we can look back at his career with fondness in its entirety. Sting has not retired and is delivering average matches, which I feel will only damage his legacy if he continues it much longer. Shawn Michaels to win here, because he deserves it.