Biggest Long Shot Winners In Kentucky Derby History

NEW YORK (CBSNewYork) -- Saturday will mark the 143rd running of the Kentucky Derby. Here are the five biggest underdogs to ever win the race.

1999: CHARISMATIC (31.3-to-1)

A descendant of Secretariat, Charismatic finished a head in front of Menifee. Charismatic went on to win the Preakness and was leading into the final furlong of the Belmont Stakes before fading.

1940: GALLAHADION (35.2-to-1)
Gallahadion was the son of 1928 Kentucky Derby champ Reigh Count, but was considered a real long shot in the race. He defeated the overwhelming favorite, Bimelech, who had 2-to-5 odds at Churchill Downs.

2009: MINE THAT BIRD (50-to-1)

After falling far behind at the start on a muddy track, jockey Calvin Borel and Mine That Bird stuck to the rail en route to winning by 6 3/4 lengths. Mine That Bird finished second in the Preakness (with Borel aboard winner Rachel Alexandra) and third at the Belmont.

2005: GIACOMO (50.3-to-1)
What was more surprising than Giacomo overcoming long odds to win the Derby was that the second-place finisher, Closing Argument, was also a 50-to-1 long shot. Giacomo finished third at the Preakness, but just seventh at the Belmont.

1913: DONERAIL (91.45-to-1)

The lead at the Derby in 1913 changed hands -- or should we say hooves? -- several times. But Donerail eventually slipped past Ten Point down the stretch to win by half a length.