Grandma's Legends, Round 2

Thus far nobody has even guessed at the trio pictured below. So here's a hint.  Two of the men shown won the event more than once.  The third never won it.   Can you name these three men?
Use the comments section below for your answers.

3 @GrandmasMara legends having a laugh on race day. Thanks @WEBC560 it was a blast!@GarverOnKUWS @cathykates1#Gmas15 pic.twitter.com/jMUKd6M1IG

— Tom Hansen (@TomHansensports) June 21, 2015