Michael Jordan vs. Kobe Bryant

Jordan's Notable Sneakers: Air Jordan XIII, Air Jordan XVII, Air Jordan XVIII
Bryant's Notable Sneakers:
 adidas KB8, adidas Kobe II, Air Jordan III "True Blue", Air Jordan VII PE, Air Jordan VIII PE  

Years: 1998, 2001 - 2003 

The heir apparent to Jordan when he entered the league in '96, Kobe went an alternate route and initially signed with The Three Stripes. By the time Jordan returned a third time with the team he helped run, Kobe was leaving adidas and the crew at Jumpman thought it would be fitting to lace Kobe in some dope Lakers-edition PEs for battles with Mike before His Airness exited for good.