Most Memorable Upsets in Kentucky Derby History

    April 30, 2019 | Sports Kentucky Derby Upsets in History

    It’s almost time for the biggest event in horse racing, as the 2019 Kentucky Derby is coming our way on May 4 at Churchill Downs.

    “The Most Exciting Two Minutes In Sports” frequently lives up to its name — and hype — with memorable winners and shock results throughout the years.

    Nitrogen Sports Blog brings you five unforgettable Kentucky Derby upsets which shocked the nation and inspired the underdogs.

    1. Mine That Bird (2009)

    What happened:
    The most recent horse on our list, Mine That Bird, won the 2009 edition at 50-1 odds. The manner of the win also made it one of the most memorable of all time.
    Why it was big:
    Mine That Bird was so far behind the pack that announcer Tom Durkin hardly noticed that he was making up ground towards the last stretch of the race.

    It was only when Mine That Bird was clearly in front of the rest of the field that Durkin was able to make a call on the horse, stumbling on his words because of the surprise emergence of Mine That Bird from the pack.

    An incredible finish saw jockey Calvin Borel bursting ahead after biding his time for the first minute, winning by 6¾ lengths. It was the longest margin of victory in over 60 years.

    2. Dark Star (1953)

    What happened:
    Dark Star was a massive 25-1 longshot before the 1953 Kentucky Derby. The odds weren’t the longest, but he beat one of the very best in a shocking result that, to this day, is remembered for being one of the biggest Kentucky Derby upsets in history.
    Why it was big:
    Dark Star’s win spoiled what could have been Native Dancer’s 12th-straight victory. Native Dancer entered the race having won all of his 11 races, but lost by a nose to Dark Star after closing the gap rapidly in the final straight.

    The 1953 Kentucky Derby was also the penultimate race of Dark Star, who had to end his career after the succeeding Preakness Stakes due to injury.

    Native Dancer won 21 out of 22 races, and his loss to Dark Star was named the greatest Kentucky Derby upset ever by Blood-Horse magazine in 2007.

    3. Gallahadion (1940)

    What happened:
    The 1940 Kentucky Derby was won by Gallahadion, a 36-1 longshot. He won the race by 1½ lengths to see off the favourite Bimelech in front of a crowd of 95,000.
    Why it was big:
    Bimelech was a massive favourite, taking the initiative along with Gallahadion at the start of the race.

    They were neck and neck at the front with the crowd expecting a Bimelech win. However, Gallahadion managed to wear down his exhausted opponent with a sudden burst of speed to claim victory.

    Bet Bitcoin on Kentucky Derby
    Bet Bitcoin on Kentucky Derby

    4. Donerail (1913)

    What happened:
    Donerail is arguably the most famous upset winner in Kentucky Derby history.

    The 1913 champion managed to stay level coming into the final straight after various horses had taken the lead. Ten Point was in front, but Donerail claimed victory by half a length and in the process, earning his place in the pantheon of greatest Kentucky Derby upsets ever.
    Why it was big:
    It sounds like a normal race, but the win stands as the biggest longshot victory in the history of the Derby, with Donerail coming in at odds of 91-1.

    The winning time of 2.04.80 also set a new Derby record at the time.

    5. Giacomo (2005)

    What happened:
    Named after Sting’s son, Giacomo won the Derby in front of an audience of 156,435.

    The 2005 winner romped home at odds of 50-1, becoming the second winner to pay triple digits.
    Why it was big:
    Giacomo is tied with Mine That Bird as the second biggest longshot in the history of the Derby. The broadcast call by Tom Durkin of this race was just as memorable, going down as arguably the best in the history of the Kentucky Derby since the event started to be televised. Giacomo was the second-biggest long shot to win the Kentucky Derby by the race ended.

    Of the 20 horses at the starting gate, Giacomo was the only one with fewer than two career victories.

    The Kentucky Derby is just as synonymous to upsets as it is to horse racing. Throughout its history, the first leg of the Triple Crown has consistently supplied a perfect blend of drama and suspense. And if that sounds like we’re describing a movie, it’s because the Kentucky Derby is almost cinematic in its appeal.

    Want to know more about Kentucky Derby bitcoin betting? Regularly check out Nitrogen Sports Blog for sports betting guide pieces.

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