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Schooling wins first gold for Singapore, edges Phelps

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What to Watch in Rio Saturday

Joseph Schooling won the men's 100 meters butterfly final on Friday to secure Singapore's first Olympic gold medal and deny Michael Phelps a 23rd in the last individual race of the American's extraordinary career.

SEE MORE: Everything you need to know about the Summer Olympics

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.

See images of Phelps in Rio:

21 PHOTOS
Michael Phelps at the Rio Olympics
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Michael Phelps at the Rio Olympics
RIO DE JANEIRO, BRAZIL - AUGUST 11: Michael Phelps of the USA competes in the Men's 100m Butterfly Heats on Day 6 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 11, 2016 in Rio de Janerio, Brazil. (Photo by Vaughn Ridley/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 11: Michael Phelps of the United States prepares ahead of his Men's 100m Butterfly heat on Day 6 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 11, 2016 in Rio de Janeiro, Brazil. (Photo by Elsa/Getty Images)
USA's Michael Phelps competes in a Men's 100m Butterfly heat during the swimming event at the Rio 2016 Olympic Games at the Olympic Aquatics Stadium in Rio de Janeiro on August 11, 2016. / AFP / GABRIEL BOUYS (Photo credit should read GABRIEL BOUYS/AFP/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 09: Phelps Michael of the United States celebrates his 20th golden Olympic medal after winning the Men's 200m Butterfly Final at the Olympic Aquatics Stadium during the Rio 2016 Summer Olympic Games on August 09, 2016 in Rio de Janeiro, Brazil. 9/08/2016 (Photo by Peter De Voecht / Photonews via Getty Images)
TOPSHOT - USA's Michael Phelps competes in a Men's 100m Butterfly heat during the swimming event at the Rio 2016 Olympic Games at the Olympic Aquatics Stadium in Rio de Janeiro on August 11, 2016. / AFP / François-Xavier MARIT (Photo credit should read FRANCOIS-XAVIER MARIT/AFP/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 11: Michael Phelps of the United States competes Men's 100m Butterfly heat on Day 6 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 11, 2016 in Rio de Janeiro, Brazil. (Photo by Adam Pretty/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 10: (L-R) Michael Phelps and Ryan Lochte of the United States compete in the second Semifinal of the Men's 200m Individual Medley on Day 5 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 10, 2016 in Rio de Janeiro, Brazil. (Photo by Al Bello/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 10: Michael Phelps of the USA and Thiago Pereira of Brazil smile after competing in the Men's 200m Individual Medley Heats on Day 5 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 10, 2016 in Rio de Janerio, Brazil. (Photo by Vaughn Ridley/Getty Images)
USA's Michael Phelps warms up before competing in a Men's 200m Individual Medley heat during the swimming event at the Rio 2016 Olympic Games at the Olympic Aquatics Stadium in Rio de Janeiro on August 10, 2016. / AFP / GABRIEL BOUYS (Photo credit should read GABRIEL BOUYS/AFP/Getty Images)
USA's Michael Phelps celebrates with his gold medal during the podium ceremony for the Men's 4x200m Freestyle Relay Final as part of the swimming event at the Rio 2016 Olympic Games at the Olympic Aquatics Stadium in Rio de Janeiro on August 9, 2016. / AFP / François-Xavier MARIT (Photo credit should read FRANCOIS-XAVIER MARIT/AFP/Getty Images)
Michael Phelps of the United States of America celebrates after the men?s 200m butterfly final of swimming at the 2016 Rio Olympic Games in Rio de Janeiro, Brazil, on Aug. 9, 2016. Michael Phelps won the gold medal with 1 minute 53.36 seconds./ CHINA OUT
RIO DE JANEIRO, BRAZIL - AUGUST 9: Gold medalist Michael Phelps of USA is congratulated by his fiancee Nicole Johnson, their 3 months old baby Boomer Phelps and his mother Debbie Phelps (left) following the medal ceremony for the men's 200m butterfly on day 4 of the Rio 2016 Olympic Games at Olympic Aquatics Stadium on August 9, 2016 in Rio de Janeiro, Brazil. (Photo by Jean Catuffe/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 07: Michael Phelps and Caeleb Dressel of the United States celebrate winning gold in the Final of the Men's 4 x 100m Freestyle Relay on Day 2 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 7, 2016 in Rio de Janeiro, Brazil. (Photo by Clive Rose/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 09: Michael Phelps of United States celebrates his gold medal after the final men's 100m freestyle at Olympic Aquatics Stadium on August 9, 2016 in Rio de Janeiro, Brazil. (Photo by Xavier Laine/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 08: Michael Phelps of the United States is congratulated by Tamas Kenderesi of Hungary in the second Semifinal of the Men's 200m Butterfly on Day 3 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 8, 2016 in Rio de Janeiro, Brazil. (Photo by Quinn Rooney/Getty Images)
USA's Michael Phelps celebrates after he won the Men's 200m Butterfly Final during the swimming event at the Rio 2016 Olympic Games at the Olympic Aquatics Stadium in Rio de Janeiro on August 9, 2016. / AFP / CHRISTOPHE SIMON (Photo credit should read CHRISTOPHE SIMON/AFP/Getty Images)
RIO DE JANEIRO, BRAZIL - AUGUST 08: Michael Phelps of the United States ahead of the second Semifinal of the Men's 200m Butterfly on Day 3 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 8, 2016 in Rio de Janeiro, Brazil. (Photo by Al Bello/Getty Images)
USA's Michael Phelps warms up before competing in a Men's 200m Butterfly heat during the swimming event at the Rio 2016 Olympic Games at the Olympic Aquatics Stadium in Rio de Janeiro on August 8, 2016. / AFP / Odd Andersen (Photo credit should read ODD ANDERSEN/AFP/Getty Images)
RIO DE JANEIRO, BRAZIL- AUGUST 07: Michael Phelps and Caeleb Dressel of the United States celebrate winning gold in the Final of the Men's 4 x 100m Freestyle Relay on Day 2 of the Rio 2016 Olympic Games at the Olympic Aquatics Stadium on August 7, 2016 in Rio de Janeiro, Brazil. Lucas Oleniuk-Toronto Star (Lucas Oleniuk/Toronto Star via Getty Images)
Swimmer Michael Phelps carries the flag to lead the U.S. team during the opening ceremonies of the Summer Olympic Games on Friday, Aug. 5, 2016, at Maracana Stadium in Rio de Janeiro, Brazil. (Mark Reis/Colorado Springs Gazette/TNS via Getty Images)
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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.

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