Defeat puts Federer's No 1 ranking under threat

The end of Roger Federer's long reign as world No 1 moved closer when he suffered a second-round defeat to the Frenchman Gilles Simon at the Toronto Masters. Andy Murray advanced to the third round with a 6-4, 6-4 victory over Sweden's Thomas Johansson.

Back on court on Wednesday for the first time since his epic loss to Rafael Nadal in the Wimbledon final, Federer was beaten 2-6, 7-5, 6-4 and his ranking is now under serious threat from Nadal, who beat the American qualifier Jesse Levine 6-4, 6-2.

Federer had looked ready to take out his Wimbledon disappointment on Simon when he won the first four games on the way to the opening set. But Simon, riding the momentum after winning the ATP event in Indianapolis on Sunday, refused to buckle, battling back to beat the Swiss winner of 12 Grand Slams and reach the third round.

It was the first time Federer had lost his opening match in a tournament since falling to Andy Murray in Dubai in March.

"The hard-court season just started so it is not the end of the world but I wish I could have started better," Federer said. "I like this surface. I like this tournament. I have done well in the past here so it definitely hurts. I have to regroup and look forward. The bigger picture is the Olympic Games and the US Open and those are the places I really want to win, so I have to make sure I am ready for that."

The 22nd-ranked Simon was a tricky opponent for the rusty Federer, who had only resumed practice four days before arriving in Toronto and received a first-round bye. Simon, however, was well into his hard-court campaign after claiming his fourth career win and second title of the season in Indianapolis with a straight-sets victory over the Russian Dmitry Tursunov.

"I was playing like I was in a dream," Simon said. "I just saw the ball and hit it as hard as possible."

Nadal, also in action for the first time since Wimbledon, struggled to find his rhythm and fell 4-1 behind in the opening set against Levine. But once the Spaniard found his range his opponent had few answers, Nadal grabbing the next five games to take the first set and cruising to an easy victory which stretched his unbeaten run to 25 matches.

"The first match is always tough, especially after one week off after Wimbledon," said Nadal, who claimed his first career hard-court title in Canada in 2005. "I only had a few days for practice. It's important to think that I can come back and I won."

Murray, the world No 9 and eighth seed here, was playing his first singles match since being comprehensively defeated by Nadal in the quarter-finals at Wimbledon. The 21-year-old won the first set with a decisive break in the 10th game but struggled with his serve throughout, dropping his opening two service games in the second set, before showing his familiar resilience to win in an hour and 38 minutes.

The Scot was scheduled to meet Stanislas Wawrinka later last night after the Swiss player overcame Russia's former world No 1, Marat Safin, 6-3, 6-4.

Murray was level at 1-1 in career meetings with Johansson, the world No 64, before their second-round match, and had received a bye in the opening round. He missed an opportunity to break in Johansson's opening service game as the first set went with serve until the sixth game. The Swede, now 33, who reached a career-high ranking of seventh in 2002, capitalised on his first break-point chance, but Murray broke back immediately. The Scot then held serve and broke Johansson for the second successive service game to clinch the first set.

The Scot's second serve continued to cause concern, with Johansson breaking in the opening game of the second set before holding serve. Johansson then claimed a 3-0 lead with a further break, but relinquished full control of the set by allowing Murray to break back immediately.

Murray held serve for the first time in the set in the fifth game and his comeback was complete when he broke Johansson again in the sixth. After both players had held serve, Murray won another service game to go 5-4 up before breaking Johansson for the fifth time in the match to secure victory.