The greatest upsets in Kentucky Derby history 3 Articles

by K Bert

Kentucky Derby history is full of big upsets and is the dream race for the handicappers to hit big because of the huge pools and possibilities for major payouts. Why is there so many upset winners in Kentucky Derby? I b...read more

by Will Kester

I was just a kid in the sixties, but I still remember when Bobby Ussery's horse beat out Willy Shoemaker on Damascus. Willy Shoemaker was always a crowd favorite, and whatever horse he rode was always a favorite, but the...read more

by Lupine

The greatest recent upset winner of the Kentucky Derby was Giacomo in 2005. He went of at odds of better than 50 to 1 and paid $102.60. Very few people gave him any chance of winning the Derby but he proved all his doubt...read more