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    Joseph Schooling beats Michael Phelps, wins Singapore's first Olympic gold

    By Eoghan Macguire, CNN

    Updated 0349 GMT (1149 HKT) August 13, 2016

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    U.S. swimmer Katie Ledecky celebrates after setting a new world record in the 800-meter freestyle on Friday, August 12. It was her fourth gold medal in Rio and the fifth of her Olympic career. She also won the 800 free in London four years ago.
    Photos: Rio Olympics: Day 7
    U.S. swimmer Katie Ledecky celebrates after setting a new world record in the 800-meter freestyle on Friday, August 12. It was her fourth gold medal in Rio and the fifth of her Olympic career. She also won the 800 free in London four years ago.
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    Joseph Schooling <a href="http://edition.cnn.com/2016/08/12/sport/michael-phelps-swimming-rio-2016/index.html" target="_blank">won Singapore's first-ever gold medal,</a> edging Michael Phelps to win the 100-meter butterfly.
    Photos: Rio Olympics: Day 7
    Joseph Schooling won Singapore's first-ever gold medal, edging Michael Phelps to win the 100-meter butterfly.
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    Spanish tennis players Rafael Nadal, left, and Marc Lopez acknowledge the crowd after winning gold in doubles. Nadal won singles gold in 2008.
    Photos: Rio Olympics: Day 7
    Spanish tennis players Rafael Nadal, left, and Marc Lopez acknowledge the crowd after winning gold in doubles. Nadal won singles gold in 2008.
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    Maya DiRado, right, looks up at her time after winning the 200-meter backstroke. DiRado was trailing Hungary's Katinka Hosszu, left, for much of the race but edged her at the end. It is DiRado's second gold medal in Rio.
    Photos: Rio Olympics: Day 7
    Maya DiRado, right, looks up at her time after winning the 200-meter backstroke. DiRado was trailing Hungary's Katinka Hosszu, left, for much of the race but edged her at the end. It is DiRado's second gold medal in Rio.
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    U.S. soccer players Mallory Pugh, right, and Carli Lloyd react during their<a href="http://www.cnn.com/2016/08/12/football/usa-sweden-football-olympics/index.html" target="_blank"> quarterfinal loss to Sweden.</a> Sweden won on penalty kicks after a 1-1 draw in extra time. It was the United States' first Olympic loss since 2000.
    Photos: Rio Olympics: Day 7
    U.S. soccer players Mallory Pugh, right, and Carli Lloyd react during their quarterfinal loss to Sweden. Sweden won on penalty kicks after a 1-1 draw in extra time. It was the United States' first Olympic loss since 2000.
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    The British track cycling team set a world record on its way to winning gold in the pursuit event. Bradley Wiggins, left, is now <a href="http://edition.cnn.com/2016/08/12/sport/bradley-wiggins-cycling-olympics-rio-2016/index.html" target="_blank">the most decorated British athlete</a> in Olympic history. He has eight medals -- five of them gold.
    Photos: Rio Olympics: Day 7
    The British track cycling team set a world record on its way to winning gold in the pursuit event. Bradley Wiggins, left, is now the most decorated British athlete in Olympic history. He has eight medals -- five of them gold.
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    U.S. athlete Michelle Carter competes in the shot put final. She won gold with a throw of 20.63 meters, becoming the first American woman ever to win the event. Carter's father, former NFL player Michael Carter, won Olympic silver in the shot put in 1984.
    Photos: Rio Olympics: Day 7
    U.S. athlete Michelle Carter competes in the shot put final. She won gold with a throw of 20.63 meters, becoming the first American woman ever to win the event. Carter's father, former NFL player Michael Carter, won Olympic silver in the shot put in 1984.
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    Chinese gymnast Li Dan won bronze in the trampoline event.
    Photos: Rio Olympics: Day 7
    Chinese gymnast Li Dan won bronze in the trampoline event.
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    French weightlifter Gaelle Nayo-Ketchanke competes in the 75-kilogram (165-pound) event.
    Photos: Rio Olympics: Day 7
    French weightlifter Gaelle Nayo-Ketchanke competes in the 75-kilogram (165-pound) event.
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    Artur Brzozowski, a race walker from Poland, makes his way through the mist during the 20-kilometer event.
    Photos: Rio Olympics: Day 7
    Artur Brzozowski, a race walker from Poland, makes his way through the mist during the 20-kilometer event.
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    Ukrainian boxer Tetyana Kob celebrates a victory in the flyweight preliminaries.
    Photos: Rio Olympics: Day 7
    Ukrainian boxer Tetyana Kob celebrates a victory in the flyweight preliminaries.
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    Canada's Kate O'Brien and Monique Sullivan compete in team sprint qualifying.
    Photos: Rio Olympics: Day 7
    Canada's Kate O'Brien and Monique Sullivan compete in team sprint qualifying.
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    Argentine sailor Lucia Falasca competes in the laser radial class.
    Photos: Rio Olympics: Day 7
    Argentine sailor Lucia Falasca competes in the laser radial class.
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    Kariman Abuljadayel became the first female sprinter to represent Saudi Arabia at the Olympics when she took part in the 100-meter preliminaries. She set a new national record of 14.61 seconds but did not qualify for the next round.
    Photos: Rio Olympics: Day 7
    Kariman Abuljadayel became the first female sprinter to represent Saudi Arabia at the Olympics when she took part in the 100-meter preliminaries. She set a new national record of 14.61 seconds but did not qualify for the next round.
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    Christine Wenzel of Germany ejects cartridges during skeet qualification.
    Photos: Rio Olympics: Day 7
    Christine Wenzel of Germany ejects cartridges during skeet qualification.
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    Mexican swimmer Liliana Ibanez Lopez takes part in the 50-meter freestyle heats.
    Photos: Rio Olympics: Day 7
    Mexican swimmer Liliana Ibanez Lopez takes part in the 50-meter freestyle heats.
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    Croatia's Sandro Sukno shoots on goal during a water polo match against Italy. Croatia won 10-7.
    Photos: Rio Olympics: Day 7
    Croatia's Sandro Sukno shoots on goal during a water polo match against Italy. Croatia won 10-7.
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    U.S. archer Brady Ellison won a bronze medal in the individual competition.
    Photos: Rio Olympics: Day 7
    U.S. archer Brady Ellison won a bronze medal in the individual competition.
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    China's Lu Wen, left, and Gao Song compete for a rebound with Serbia's Sonja Petrovic.
    Photos: Rio Olympics: Day 7
    China's Lu Wen, left, and Gao Song compete for a rebound with Serbia's Sonja Petrovic.
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    Ethiopia's Almaz Ayana celebrates after winning the 10,000 meters. She stunned spectators by crossing the line in 29 minutes, 17.45 seconds, <a href="http://www.cnn.com/2016/08/12/sport/rio-olympics-ethiopia-10000m-world-record/index.html" target="_blank">smashing a record</a> that had stood for nearly 23 years.
    Photos: Rio Olympics: Day 7
    Ethiopia's Almaz Ayana celebrates after winning the 10,000 meters. She stunned spectators by crossing the line in 29 minutes, 17.45 seconds, smashing a record that had stood for nearly 23 years.
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    Sweden's Linnea Torstensson, center, competes against the Netherlands' Kelly Dulfer and Laura van der Heijden during a preliminary handball match.
    Photos: Rio Olympics: Day 7
    Sweden's Linnea Torstensson, center, competes against the Netherlands' Kelly Dulfer and Laura van der Heijden during a preliminary handball match.
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    U.S. athlete Raven Saunders competes in the shot put.
    Photos: Rio Olympics: Day 7
    U.S. athlete Raven Saunders competes in the shot put.
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    A remote-control car carries the discus in the men's qualifying round.
    Photos: Rio Olympics: Day 7
    A remote-control car carries the discus in the men's qualifying round.
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    Germany's Claudia Rath competes in the high jump portion of the heptathlon.
    Photos: Rio Olympics: Day 7
    Germany's Claudia Rath competes in the high jump portion of the heptathlon.
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    France's Jeremy Cadot reacts during the team foil quarterfinal against China.
    Photos: Rio Olympics: Day 7
    France's Jeremy Cadot reacts during the team foil quarterfinal against China.
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    From left, Cuba's Yorgelis Rodriguez, Germany's Claudia Rath, the Netherlands' Anouk Vetter and Great Britain's Katarina Johnson-Thompson compete in the 100-meter hurdles during the heptathlon.
    Photos: Rio Olympics: Day 7
    From left, Cuba's Yorgelis Rodriguez, Germany's Claudia Rath, the Netherlands' Anouk Vetter and Great Britain's Katarina Johnson-Thompson compete in the 100-meter hurdles during the heptathlon.
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    A rower prepares boats for a training session.
    Photos: Rio Olympics: Day 7
    A rower prepares boats for a training session.
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    26 rio olympics 081227 rio olympics 0812 RESTRICTED24 rio olympics 081225 rio olympics 081219 rio olympics 081223 rio olympics 081201 Michelle Carter 081222 rio olympics 081221 rio olympics 081220 rio olympics 081218 rio olympics 081217 rio olympics 081216 rio olympics 081215 rio olympics 081214 rio olympics 081213 rio olympics 081212 rio olympics 081211 rio olympics 081210 rio olympics 081209 rio olympics 081208 rio olympics 081207 rio olympics 081206 rio olympics 081204 rio olympics 081203 rio olympics 081202 rio olympics 081201 rio olympics 0812

    Story highlights

    • Outsider shocks Phelps in 100m butterfly
    • Schooling wins Singapore's first gold
    • Phelps in three-way tie for second
    • Ledecky wins her fourth gold of Rio 2016

    (CNN)If there was a record for breaking records, Michael Phelps would doubtless don his goggles and cap to swim for it.

    But the "Baltimore Bullet" couldn't add to his unparalleled 23 Olympic gold medals in the 100-meter butterfly Friday as he was beaten by outsider Joseph Schooling.
      Day 7: Follow all the action
      Schooling became the first Singaporean athlete to win a Games gold -- and did so in an Olympic record time of 50.39 seconds.
      Remarkably Phelps finished in a three-way tie for the silver -- the 27th medal of his career -- along with South Africa's Chad le Clos and Laszlo Cseh of Hungary, as they all clocked the same time of 51.14 seconds.
      Read More
      The 21-year-old Schooling punched the water upon realizing he had foiled three of the biggest names in world swimming.
      Phelps will now have to wait to see if he can add to his 23 gold medals when he is expected to take part in Saturday's men's 4x100m freestyle medley.
      READ: The other Phelps winning in Rio
      Remarkably, Phelps' silver success was about the most downbeat moment on a night of triumph in the pool for Team USA.
      Teenager Katie Ledecky picked up a fourth gold medal of the Rio Games in the 800m freestyle final, smashing her own world record in the process to clock a time of eight minutes 04.79 seconds.
      She won her first Olympic gold in London four years ago when she was just 15. At such a tender age, it's far from an impossibility that she could could challenge Phelps record in the future.
      Ledecky's Friday triumph also means she becomes the first swimmer to win the 200m, 400m and 800m freestyle titles in the same Games since Debbie Meyer did so in Mexico 1968.
      Earlier, US teammate Maya Dirado earned her first gold of the Rio Games, after claiming a silver and bronze earlier in the week, as she pipped Katinka Hosszu in the women's 200m backstroke.
      Simone Manuel breaks the ultimate color barrier -- the pool
      Simone Manuel breaks the ultimate color barrier -- the pool
      Dirado hunted down favorite Hosszu in the final 50 meters, touching the wall fractions of a second before her opponent in the next lane to deny Hungary's "Iron Lady" her fourth gold medal of Rio 2016.
      Even more delight was to follow for the US as Anthony Ervin became the oldest Olympic swimming champion with gold in the men's 50m freestyle.
        The 35-year-old beat second-placed Florian Manadou of France by a margin of just 0.01 seconds.
        Fellow American Nathan Adrian claimed bronze a further 0.07 seconds back.