2011 top 50 player with a wooden racquet back in the day?
Or Rod Laver with today's equipment, fitness, and training?
Either way I think Laver wins.
have you ever seen old footage? The players pattycake the ball over the net, they were good for their time but there is no way they would beat a modern player with the cyclones of topspin. They would not know how to handle the powerful spin. The old time game looks like badminton, they would not hit back the power shots with their fly-swatters.