: For his final leg, he picked a horse named Lupita, which had lost its previous 28 races.

: The trio placed a massive longshot bet at a racetrack in Tijuana, Mexico.

: Australian tycoon Kerry Packer once bet $4.6 million on a horse named Mahogany . The horse won, netting Packer a payout of approximately $20 million. Horse Betting

: They unknowingly placed the wager with bookmakers linked to a drug cartel. When Winning Colors defied the odds to become one of the few fillies to win the Derby, the men had to figure out how to collect their winnings without getting killed.

: Against all logic, Lupita won, completing Whiteley's six-race accumulator and turning his £2 into £1.45 million . Fast Facts: Famous Wagering Feats : For his final leg, he picked a

One of the most legendary figures in horse racing is , a physics dropout who applied advanced mathematics to the track. Benter moved to Hong Kong and developed a computer model that analyzed over 130 variables for every horse in every race.

: In 2001, Benter's model correctly predicted the "Triple Triple" at Happy Valley—a jackpot requiring the bettor to pick the top three finishers in three specific races. The horse won, netting Packer a payout of

In 2011, , a 61-year-old heating engineer, experienced what many call the ultimate stroke of luck.