Andy Murray has played in 40 finals in his professional career and won 26 titles but has yet to feature in the climax of a clay-court event.
This week's Madrid Masters could provide him with his best opportunity yet. Novak Djokovic's defeat by Grigor Dimitrov in the second round in the Spanish capital has left Murray as the highest-ranked player in the top half of the draw, while the likes of Rafael Nadal and Roger Federer are slugging it out in the bottom half.
Murray has won his last 10 matches against Gilles Simon, his opponent in the third round today. The winner will go into a quarter-final on Friday against either Tomas Berdych, who as the world No 6 is the next highest ranked player in Murray's section, or Kevin Anderson.
For the moment, nevertheless, Murray will not be looking beyond his meeting with Simon. "It's always difficult against him because there are a lot of long rallies," Murray said. "He moves unbelievably well and makes very few unforced errors. Every time you play against him there are a lot of long games and points, so you need to be prepared for that. I've played well against him in the past, so I hope I can do the same again."
He added: "On clay there are a lot of very tough opponents. It's a surface that I didn't grow up on, so I don't feel as comfortable on it. But it's not to say that, with the right attitude and work ethic and the right mindset going into these events, I can't play well at them.
"I think my game should suit clay well. I just need to play a lot on it. I'd like to play a lot on it. So I would like to play more on it during the year. I think that would help me for the French Open."
Djokovic's defeat leaves concerns about his fitness with the start of the French Open only two and a half weeks away. During his 7-6, 6-7, 6-3 loss to Dimitrov, the world No 1 aggravated a problem with his right ankle. Djokovic suffered the injury playing in the Davis Cup last month and said he had been unable to practise for 12 days in the build-up to Madrid.
Dimitrov, meanwhile, is rapidly emerging as the best of the next generation of players. The 21-year-old Bulgarian took Nadal to three sets in Monte Carlo last month and is now at a career-high No 28 in the world rankings.
Nadal began his Madrid campaign with a patchy 6-3, 6-4 victory over Benoît Paire. The Frenchman hit 24 winners to his opponent's 18, but Nadal made fewer errors and Paire paid for his reliance on his backhand, which is his stronger flank.
Victoria Azarenka, runner-up in Madrid the last two years, was beaten 1-6, 6-2, 6-3 by Russia's Ekaterina Makarova.
The Women's Tennis Association announced that its season-ending championships, currently staged in Istanbul, will be played in Singapore for five years from 2014.