Michael Jordan vs. Penny Hardaway 

Jordan's Notable Sneakers: Air Jordan XI, Air Jordan X, Nike Air Flight One
Hardaway's Notable Sneakers:
 Nike Air Up, Nike Air Flight One, Nike Air Penny I   

Years: 1994 - 1998, 2001 - 2003

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. Not to mention the fact that Jordan rocked Penny's Nike Air Flight Ones and Penny sported MJ's IXs, which is a sure sign of mutual respect.