#2 Floyd Mayweather vs Bruce Lee

Even if imaginary, this fight is a mouth-watering contest for martial arts fans. The forefather of modern MMA versus possibly the greatest defensive boxer of all time.
The most important question here is, would this be a regulated match or a streetfight? If it's the former, and assuming it's 'strikes-only', then Floyd's guerrilla-style should get him the win. Not just because of his footwork and defence, but more pertinently because Bruce Lee never had a professional fight, apart from amateur boxing matches in his youth.
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Now, the latter could prove a complete 180. Bruce Lee was a well-oiled machine and his speed, precision and diversity would drown out Mayweather's defence in a streetfight. Either scenario would indubitably draw crowds by the boatloads.