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Jo-Wilfried Tsonga and Janko Tipsarevic were both forced to retire injured in the first round of the Valencia Open on Tuesday.
Tsonga and Tipsarevic suffered major setbacks in their bids to qualify for the season-ending ATP Tour Championships in London next month.
Frenchman Tsonga, who currently occupies the eighth and final qualifying berth, was forced to withdraw with a back injury when he trailed 3-1 in the first set of his match against Belgium's Xavier Malisse.
Meanwhile Serbia's Tipsarevic, who is currently one place behind Tsonga at ninth in the standings, also pulled out in the opening set of his match against Gilles Simon, trailing 5-4, with an unspecified complaint.
The twin retirements were good news for sixth seed Nicolas Almagro, ranked 10th in the race, who took advantage with a 7-5 6-3 win over Juan Carlos Ferrero, bringing the curtain down on the career of the former world number one.
Top seed David Ferrer, who is already safely qualified for London, saw off gutsy Belgian Olivier Rochus 7-5 7-5, American Sam Querrey beat Feliciano Lopez 6-4 7-6 (7/4), and there were also wins for Alex Dolgopolov and Jurgen Melzer.