#1: Sting Vs. The Undertaker

For years, fans have pondered who would have won in a match pitting The Undertaker Vs. Sting. Sadly, a match between the two characters never took place, as whilst the Demon of Death Valley was becoming a legend of the WWF, Sting was a loyal soldier for WCW in the Monday night wars. And though these two characters never squared off in either company, the men behind the pair did.
In 1990, Sting had already established himself as one of the big names in WCW, capturing the NWA World Heavyweight Championship from Ric Flair at the Great American Bash in July that year. Meanwhile, a young upstart by the name of 'Mean' Mark Callous had grown tired of the company, and was fancying a change. In one of his final matches in WCW, Callous took on the Stinger, before parting for the WWF.
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Debuting at the 1990 Survivor Series, Callous would become The Undertaker, and though the Deadman persona never encountered the Stinger, WCW's fans got a glimpse of what the two future legends could do in the ring together.