Frenchman Julien Benneteau sent defending champion Roger Federer crashing out of the ATP Rotterdam Open on Friday with a stunning 6-3, 7-5 quarterfinal upset.

Federer, who lifted the trophy in his last two appearances in 2005 and 2012, last suffered defeat in the event against Tim Henman in 2004.

Rafael Nadal advanced to the semifinals of the ATP Brazil Open on Friday at Sao Paulo, with a 3-6, 6-4, 6-4 win over Argentine Carlos Berlocq.

The 26-year-old Spaniard, ranked No. 5 in the world, won his singles quarterfinal match in two hours 24 minutes against the 30-year old Argentine, ranked 78th in the world.

In another quarterfinal, Argentine David Nalbandian beat Spaniard Nicolas Almagro, the winner of the Brazil Open last year.

Raonic moves up

Milos Raonic rolled to a 7-6(0), 6-3 quarterfinal victory over Denis Istomin at the ATP SAP Open at San Jose.

Raonic hammered 14 aces and needed just 80 minutes to oust Istomin in a rematch of last year’s final which was also won by the Canadian.

The results: At Rotterdam: ATP Rotterdam Open: Semifinals: Juan Martin del Potro bt Grigor Dimitrov 6-4, 6-4. Quarterfinals: Julien Benneteau bt Roger Federer 6-3, 7-5; Gilles Simon bt Martin Klizan 6-7(6), 6-3, 3-0 (retd.).

At San Jose: ATP SAP Open: Quarterfinals: Tommy Haas bt Steve Johnson 6-4, 6-2; John Isner bt Xavier Malisse 7-6(8), 6-2; Milos Raonic bt Denis Istomin 7-6(0), 6-3; Sam Querrey bt Alejandro Falla 6-3, 4-6, 7-5.

At Sao Paulo: ATP Brazil Open: Quarterfinals: Rafael Nadal bt Carlos Berlocq 3-6, 6-4, 6-4; Martin Alund bt Filippo Volandri 7-5, 7-6(5); David Nalbandian bt Nicolas Almagro 7-6(5), 3-6, 7-6(3).

At Doha: WTA Qatar Open: Semifinals: Serena Williams bt Maria Sharapova 6-3, 6-2; Victoria Azarenka bt Agnieszka Radwanska 6-3, 6-3. Quarterfinals: Agnieszka Radwanska bt Caroline Wozniacki 6-2, 7-5; Serena Williams bt Petra Kvitova 3-6, 6-3, 7-5.

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