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tennis • Top-ranked Rafael Nadal's clay-court struggles worsened Friday as his 41-match winning streak at the Barcelona Open ended with a three-set loss to Nicolas Almagro in the quarterfinals.

Nadal was looking for his ninth title in Barcelona but lost 2-6, 7-6 (5), 6-4, a week after going out in the quarterfinals of the Monte Carlo Masters to David Ferrer. Nadal, widely considered the greatest clay-court player of all time, hadn't lost in Barcelona since his debut as a 15-year-old in 2003, although he missed the tournament in 2010. He had not dropped a set here since the 2008 final.

Almagro will face Santiago Giraldo in Saturday's semifinals after Philipp Kohlschreiber retired with an injury while trailing 6-4, 4-3.

• Two-time defending champion Maria Sharapova needed eight match points to put away top-seeded Agnieszka Radwanska 6-4, 6-3 for a place in the Porsche Grand Prix semifinals in Stuttgart, Germany. Sharapova's semifinal opponent will be eighth-seeded Sara Errani, who was leading 6-3, 6-7 (6), 3-0 when Carla Suarez Navarro retired with a hand injury.

Phelps swims flyin freestyle race

SWIMMING • Michael Phelps' comeback meet was cut short Friday in Mesa, Ariz., when he failed to advance to the 50-meter freestyle final. The 18-time Olympic gold medalist used the morning preliminaries at the Arena Grand Prix to fine-tune his butterfly stroke instead of doing freestyle like everyone else. He finished seventh in a time of 24.06 seconds, missing out on the eight-man evening final.

Phelps didn't even make any of the three consolation finals because he was 42nd overall; only the top 32 qualify for those, so his first competition since retiring after the 2012 London Olympics ended early.

Ex-Barcelona coach Vilanova dies at 45

SOCCER • Tito Vilanova, the soccer coach who succeeded Pep Guardiola at Barcelona and won the Spanish league title in his only season in charge, died Friday of throat cancer. He was 45. Vilanova had a recurring tumor in a saliva gland. Vilanova first became ill in November 2011 while still an assistant to Guardiola. Vilanova returned and took over from Guardiola the next season, when he led Barcelona to the Spanish league title.

Oregon triumphsin distance medley

RUNNING • Oregon freshman Edward Cheserek led the Ducks to the distance medley relay championship in the Penn Relays in Philadelphia, running the closing mile leg in 3 minutes, 57.98 seconds.

Cheserek, the NCAA cross country champion, teamed with seniors Mac Fleet, Mike Berry and Boru Guyota to finish in 9:25.40 in front of 38,135 fans at Franklin Field. Fleet ran the opening 1,200-meter leg in 2:53.95, Berry followed with a 44.72 in the 400, and Guyota had a 1:48.77 in the 800.

Villanova was second in 9:28.93, and Stanford third at 9:29.66.

The Associated Press

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