1. Bret Hart vs. Hulk Hogan (WCW Monday Nitro; September 28, 1998)
At this point in the Monday Night Wars, WCW's Nitro still had a strong lead over WWE's Raw in the ratings. The New World Order was still running rampant on the WCW roster, two years removed from when Hulk Hogan first starting sporting the black and white. WCW was giving away blockbuster bouts on their flagship show each week in a desperate attempt to maintain their viewership and this marquee match between Hogan and Bret Hart was one of them. WCW could have easily done what WWE did not and put them in a feud together, but they opted to broadcast their first ever singles encounter on free TV instead.Hart was still somewhat of a hot commodity at the time after the events of The Montreal Screwjob at Survivor Series the year prior, but WCW failed to use him to his full potential. Before a winner could be determined, interference from Sting and others resulted in the contest being thrown out. It was typical of WCW to offer a money match for free on TV and came as no surprise when Nitro began losing the battle for ratings shortly thereafter. Hart retired from the ring two years later before a rematch between the two icons could be held.