Reggie Miller vs. Michael Jordan

Jordan's Memorable Sneakers: Air Jordan III, Air Jordan IX, Air Jordan X, Air Jordan XIII
Miller's Memorable Sneakers: Nike Air Total Max Uptempo, Nike Air Way Up, Nike Air Flight 89

Years: 1987 - 1998, 2001 - 2003

Reggie Miller and the Pacers weren't much concern for MJ and the Bulls in the earlier years but Miller's competitive nature carried Indiana pretty far in the early '00s. By the time Reggie laced up the Total Max Uptempo, the Pacers were giving MJ all sorts of headaches. We all know who had the last laugh and the better sneakers, though.