#4 Hulk Hogan def. Randy Orton (WWE SummerSlam 2006)
To this day, Hulk Hogan's last ever match in WWE came at SummerSlam 2006, against the 'Legend Killer'. But, unfortunately for Randy Orton, he was unable to kill the legend of the Hulkster. He would have benefited greatly from a victory over Hogan, no matter how old he was at the time.
Orton spent the build-up to SummerSlam simply beating up various legends, setting himself up for superstardom in WWE. However, like many other times in the past, Hogan refused to lose a match. This was particularly detrimental to the rising 26-year-old star.
While the stage was set for a monumental Orton victory, Hogan came out on top. This was as questionable as the previous year's SummerSlam main event, where the Hulkster defeated Shawn Michaels in one of the most infamous matches in WWE history.
However, HBK was already an established star by then. Orton was fairly new, yet to become the top guy that he is today. It all worked out in the end, but Randy Orton was seemingly robbed of a major career-making moment at SummerSlam 2006.