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Michael Phelps was expected to win the 23rd gold of his Olympic career, but the American suffered a shock defeat at the hands of 21-year-old Joseph Schooling.
Michael Phelps suffered a shock defeat in the pool as Singapore's Joseph Schooling beat the American in the 100m butterfly.
Twenty-one-year-old Schooling produced an Olympic record 50.39 to take gold and force Phelps into silver, which he shared with both Chad le Clos and Laszlo Cseh in 51.14.
Phelps was searching for a fifth gold of the Rio Games, a 14th individual Olympic title and a staggering 23rd gold of his glittering career.