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WATCH: Biggest shock of Rio 2016 - Joseph Schooling stuns Michael Phelps
Phelps, who now has 27 medals, had been hoping to win the event for the fourth successive Games.
Rio de Janeiro: Joseph Schooling stunned Michael Phelps to win the men`s 100 metres butterfly final on Friday.
In doing so, he clinched Singapore`s first Olympic gold medal and denied the American a 23rd in the last individual race of his extraordinary career.
Phelps, the defending champion and world record holder who is heading into retirement -- again -- after Rio, finished second in a three-way dead heat with two of his greatest rivals -- South Africa`s Chad Le Clos and Hungary`s Laszlo Cseh.
Astonishingly, all three touched out in 51.14 seconds, behind Schooling`s Olympic record 50.39.
Phelps, who now has 27 medals, had been hoping to win the event for the fourth successive Games.
(With Agency inputs)