At the US Open, Safin lost in the second round to Tommy Robredo. At the Moscow Kremlin Cup, he defeated Noam Okun, Julien Benneteau, Nikolay Davydenko, and Mischa Zverev, only to lose to another compatriot Igor Kunitsyn in the final. It was Safin's first final appearance since 2006, in the same event. Following the Kremlin Cup, Safin withdrew from the Madrid Masters event with a shoulder injury. His next event was the St. Petersburg Open, at which he lost in the second round. He then lost his first-round match at the final ATP tournament of the calendar: the Paris Masters, to Juan Mónaco. In the post-match conference, he raised the possibility of his retirement from the sport. Via a message posted on his official website, he said he was going to take a holiday and then seriously consider his options regarding his future in tennis. He finished the year 2008 ranked at No. 29.