#4 Rowdy Roddy Piper v/s Georges St-Pierre
I say Rowdy Roddy Piper would have met his ideal match in Georges St-Pierre not only because of their Canadian roots but also because they both had to go through a tumultuous childhood.
Piper was expelled from school and had a fallout with him father while on the other hand Pierre was a victim of bullying. Both later trained in boxing and martial arts. Piper earned a black belt in judo while Georges St-Pierre worked his way through to a karate black belt.
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A bout between the two would have resulted in a closely-contested competition leveraged by the fact that both competitors are considered legends in their area of expertise. Both Piper and St-Pierre are known to be fierce competitors, having a background in both wrestling and martial arts.