For the following scenario is similar to Superman vs Ali except that we need to make the following assumption.
A.) Professional Wrestling in real
1. Superman vs The Undertaker: Buried Alive match
2. Triple H vs Superman: Hell in a Cell
3. John Cena vs Superman: I quit match
4. Superman vs CM Punk: Submission match
5. Superman vs Shawn Micheals: Ladder Match
6. Brett "The Hitman" Hart vs Superman: Ironman match
If it's real like the open stated then there are no "Booker's" or "putting over". I should have made the Undertaker match at Wrestlemania. The Man of Steel vs the streak.
Well, if you assume that it's all real and there's no work involved or ring psychology or learning how to take bumps and what not, per the "wrestling world", Superman would get out-wrestled and he has virtually no wrestling experience, amateur or professional wise, and his array of H2H skills wouldn't really help him against some of these guys.