MADRID, Oct 17: Towering Croat Ivo Karlovic toppled third seed Novak Djokovic 7-6, 7-6 to make the quarter-finals of the Madrid Masters on Thursday.

The 14th seed will meet Frenchman Gilles Simon next after unsettling Djokovic with his booming serves. Both sets went to tiebreaks, which favoured Karlovic, who blasted 20 aces, to Djokovic’s eight.

Earlier, world number one Rafael Nadal, Roger Federer and Andy Murray all made it to the last eight, but defending champion David Nalbandian went out.

Federer comfortably beat Jo-Wilfried Tsonga 6-4, 6-1, taking the first when Tsonga double-faulted on his serve.

In the only quarter-final contest featuring two seeds, he will face Argentina’s Juan Martin del Potro.

The ninth seed beat compatriot and seventh seed Nalbandian 6-4, 6-2 in just 85 minutes.

Top seed Nadal booked his place by breezing past an out-of-sorts Richard Gasquet 6-4, 6-2.

It was a much more convincing performance from the top seed, who had laboured through his opener against Ernests Gulbis on Tuesday.

Next for up for Nadal is compatriot Feliciano Lopez, who saw off Switzerland’s Stanislas Wawrinka 6-4, 6-4.

Fourth seed Murray was forced to work for it against big-serving Croatian Marin Cilic 7-5, 7-6. He faces France’s Gael Monfils who put out the eighth seed Andy Roddick 6-4, 3-6, 6-3.

Murray was broken early and was staring down the barrel in the ninth game of the opening set as 20-year-old Cilic held three set points.

But the Scot roared back thanks to some stinging returns, including one right into the feet of the lofty Croatian, to break back. He then broke again to take the set.

Despite suffering from a sore knee, Murray served for the match at 5-3 in the second but Cilic broke back and took it to the tiebreak which the Scot won 7-2.

Results (prefix number denotes seeding):

Third round: 14-Ivo Karlovic (Croatia) bt 3-Novak Djokovic (Serbia) 7-6(4), 7-6(5); 2-Roger Federer (Switzerland) bt 16-Jo-Wilfried Tsonga (France) 6-4, 6-1; 1-Rafael Nadal (Spain) bt 15-Richard Gasquet (France) 6-4, 6-2; Gael Monfils (France) bt 8-Andy Roddick (US) 6-4, 3-6, 6-3; Feliciano Lopez (Spain) bt 10-Stanislas Wawrinka (Switzer-land) 6-4, 6-4; 4-Andy Murray (Britain) bt Marin Cilic (Croatia) 7-5, 7-6(2); 9-Juan Martin del Potro (Argentina) bt 7-David Nalbandian (Argentina) 6-4, 6-2; Gilles Simon (France) bt Robby Ginepri (US) 6-7(6), 6-4, 7-6(6).

JANKOVIC STOPPED

ZURICH: Jelena Jankovic’s bid for a fourth straight title ended on Thursday when the world number one lost 5-7, 6-3, 6-3 to unseeded Italian Flavia Pennetta in the Zurich Open second round.

The Serb was playing her opening match of the week after receiving a first-round bye but showed little sign of having benefited from her brief rest since winning in Moscow.

Jankovic took the first set with two breaks of serve against one dropped service game of her own but appeared to be unsettled by a painful-looking fall in the 12th game.

She received treatment for a cut on her knee after dropping serve again early in the second set only to fall further behind when Pennetta hit a return winner to go 4-1 up.

Jankovic broke back but continued to look out of sorts, saving one break point at 4-2 before suffering a further break at 5-3.

The third set was evenly balanced with the first seven games going to serve before Pennetta grabbed what proved to be the decisive break with a backhand winner down the line.

The Italian world number 17, who had lost all five of her previous meetings with Jankovic including last week’s Moscow quarter-finals, kept her nerve to serve out the match as she finished off with an ace.

On a bad day for the tournament’s organisers Russian fourth seed Vera Zvonareva and Polish fifth seed Agnieszka Radwanska also suffered second-round exits.

Radwanska was beaten 2-6, 7-6, 6-3 by Slovenian world number 21 Katarina Srebotnik in a serious blow to the Pole’s hopes of qualifying for the WTA Championships.

The world number 10 is the worst-placed of the four main contenders for the three remaining spots at the year-ending tournament and is now set to lose further ground to her nearest rival Venus Williams.

Zvonareva, who has yet to secure her own place at the Championships, retired from her own second-round match while trailing Spain’s Anabel Medina Garrigues 6-3, 3-0.

Serbian second seed Ana Ivanovic provided some relief by sailing through her second-round match against French world number 16 Marion Bartoli 6-2, 6-4.

Results:

Second round: Anabel Medina Garrigues (Spain) bt 4-Vera Zvonareva (Russia) 6-3, 3-0 (Zvonareva retired); 2-Ana Ivanovic (Serbia) bt Marion Bartoli (France) 6-2, 6-4; Katarina Srebotnik (Slovenia) bt 5-Agnieszka Radwanska (Poland) 2-6, 7-6(6), 6-3; Flavia Pennetta (Italy) bt 1-Jelena Jankovic (Serbia) 5-7, 6-3, 6-3; Petra Kvitova (Czech Republic) bt Sofia Arvidsson (Sweden) 6-2, 6-1; Victoria Azarenka (Belarus) bt Monica Niculescu (Romania) 6-0, 6-0.—Reuters