#1 Sting
For many years now, fans have wanted to see The Undertaker and Sting square off. After all, Sting's 'crow' gimmick was not very dissimilar from that of The Undertaker's classic avatar. Also both men were the generals of their company, during the 'Monday Night Wars' era. For various reasons, this match has never really come to pass.
However, the men have faced each other once. Sting, in his 'beach' avatar took on 'Mean Mark' Callous at the Greensboro Coliseum in 1990. They even faced off in a tag team match after that.
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No footage exists of their match though. After all, it was only a house show.
If only people had known how sought after this clash would be, just a few decades later.