MADRID, Spain — Rafael Nadal will end the year at No. 1 after he and Roger Federer both lost in the semifinals of the Madrid Masters on Saturday.

Andy Murray and Gilles Simon will meet in the final. The resilient Simon upset Nadal 3-6, 7-5, 7-6 (6) after the fourth-ranked Murray beat Federer 3-6, 6-3, 7-5 to prevent what would have been the fifth Nadal-Federer final this season.

Once Federer lost, Nadal clinched becoming the first Spanish player in the Open era to end the year with the No. 1 ranking.

Simon goes for his fourth title in 2008 thanks to excellent shot-making throughout the final set, which was marked by long rallies and replay challenges — including the final point, when Hawkeye confirmed that Nadal’s shot sailed long.

Simon saved 17 break point chances — including seven in the third set — in a match that lasted nearly 312 hours. Nadal lost for only the second time in 73 matches after taking the first set.

“I’m playing a great, great player and I don’t want to miss that so I fight for every point,” said a visibly drained Simon, who was taken to three sets for the fifth straight match. “When you play against Rafa in Madrid, that’s not easy.”

The 16th-ranked Simon, who jumps to No. 10 on Monday, won at Bucharest, Casablanca and Indianapolis. He beat Federer at Toronto in August to become the first to register wins over two separate top-ranked players in the same year since Rainer Schuettler triumphed over Andre Agassi and Andy Roddick in 2003.

Simon had saved match points against three of his previous four opponents, but the Frenchman’s powerful, low groundstrokes troubled the top-ranked Nadal enough that he didn’t have to do it a fourth time.

In other tennis on Saturday:

Venus beats Ivanovic in semis

ZURICH, Switzerland — Venus Williams rallied from a set down to beat second-seeded Ana Ivanovic 4-6, 6-3, 6-4 in the Zurich Open semifinals.

Williams will face Flavia Pennetta in today’s final, after the Italian beat Spain’s Anabel Medina Garrigues 6-3, 7-6 (6) in an earlier match.

Pennetta is 3-1 against the 28-year-old American and beat her in Moscow last week.