SHANGHAI (AP) Jo-Wilfried Tsonga was knocked out of the second round of the Shanghai Masters on Wednesday, losing 6-7 (1), 6-4, 6-4 to Kei Nishikori of Japan.

The fourth-seeded Frenchman fought off two match points with aces before hitting a backhand long to hand Nishikori the win.

The loss will hurt Tsonga's chances of claiming one of the four remaining spots in the season-ending ATP World Tour Finals in London. He currently sits eighth in the standings, the last qualifying spot.

Third-seeded David Ferrer of Spain defeated Canadian Milos Raonic 7-5, 7-6 (7) in another second-round match. Raonic, who has now lost to Ferrer three times this year, had a set point in the tiebreaker, but couldn't convert.

American teenager Ryan Harrison, who upset 11th-seeded Viktor Troicki in the first round, lost to fellow qualifier Matthew Ebden of Australia, 6-4, 6-2. Ebden, ranked 124th, had only won eight matches on the ATP Tour coming into Shanghai.

Spain's Juan Carlos Ferrero, the 2003 French Open champion, rallied from a set down to beat compatriot Fernando Verdasco, the 16th seed, 4-6, 6-3, 6-2.

Ferrero had dropped out of the top 100 earlier this year due to injury layoffs, but is coming off a quarterfinal appearance at the China Open in Beijing last week.

Tsonga appeared sluggish early on, spraying forehands long and allowing Nishikori to run him around the court. Although he won the first-set tiebreaker, he was broken twice and hit only four winners to drop the second set.

The 47th-ranked Nishikori, who was 1-9 against top 10-ranked players before the match, then broke Tsonga twice more in the third set to close out the match after nearly two and a half hours.

He's really talented, especially when everything works,'' Tsonga said.Today he didn't miss one drop shot. He played really well. He returned unbelievable. I think nobody breaks me many times like this.''

In other second-round matches, Colombia's Santiago Giraldo edged out 14th-seeded Jurgen Melzer of Austria, 4-6, 6-4, 7-6 (5), and Alexandr Dolgopolov, the 12th seed from Ukraine, defeated qualifier Albert Ramos of Spain, 5-7, 6-3, 6-2.