Joseph Schooling pulled off a stunning upset at the Rio Olympics on Friday by beating Michael Phelps in the 100m butterfly to win Singapore’s first ever gold medal.

Asian champion Schooling, 21, completed a wire-to-wire victory to deny Phelps a fourth successive title in the event, winning in a Games record 50.39sec as Phelps, amazingly, tied with both Chad le Clos and Laszlo Cseh for the silver.

The American, who had won four finals in Rio to take his record tally to a staggering 22 golds, clocked 51.14, along with fierce rivals le Clos and Cseh.

Victory in Friday’s fly would have given Phelps a 14th individual Olympic title, but Schooling proved too strong.

Schooling, who took bronze at last year’s world championships, punched the water and roared with delight as Phelps swam over to pat him on the back before le Clos ruffled the youngster’s hair.

Phelps, competing in his fifth and final Games, will be odds-on to win a fifth gold medal in Sunday’s 4x100m medley relay, an event the Americans have never lost at the Olympics, to finish with a total of 23 golds.  DM

Photo: Joseph Schooling of Singapore celebrates winning the men’s 100m Butterfly Final race of the Rio 2016 Olympic Games Swimming events at Olympic Aquatics Stadium at the Olympic Park in Rio de Janeiro, Brazil, 12 August 2016. EPA/BERND THISSEN