Nike Air Max Penny I vs. Air Jordan XI "Playoffs" 

Players: Penny Hardaway vs. Michael Jordan
Year: 1996

These two didn't have the same type of history as other players, but after Michael left the game Penny had became one of the league's top stars and Nike's new face. Their battles on the court featured a handful of sneakers that sit on everyone's all-time favorite lists, especially the Penny Is and Jordan XIs. Not to mention the fact that Jordan rocked Penny's Nike Air Flight Ones the year before and Penny sported MJ's IXs, which is a sure sign of mutual respect.