second, but Nishikori sustained a back injury while leading 4–2 and was forced to retire at 3–0 in the 3rd set having lost 7 games in a row. The result saw him achieve a career-high #9 in ATP singles ranking. Nishikori lost in the first round of the French Open to Martin Kližan in three sets. Nishikori bounced back from the French Open first round loss in the grass court season by reaching the semifinals of the 2014 Gerry Weber Open before losing to Roger Federer in straight sets. Nishikori participated in the Wimbledon Championships and made it to the fourth round after surviving a tight 5-setter against clay-court specialist Simone Bolelli, but eventually lost in the fourth round to Milos Raonic, despite winning the opening set. Nishikori opened his hard-court season by participating in the Citi Open. He reached the quarterfinals only to be beaten by Richard Gasquet for the fifth time in his career in straight sets. Nishikori reached his first Grand Slam final at the 2014 US Open. He beat Wayne Odesnik, Pablo Andújar, Leonardo Mayer and then world No. 6 Milos Raonic in a marathon five-set match that lasted until 2:26 am, tying the record for late finishes at the US Open en route to the quarterfinals. In the quarterfinals, he scored a rare upset over Australian Open champion Stan Wawrinka, who had thus far dominated their meetings to ensure that he would regain a top ten ranking. He also became the first Japanese man in 81 years to reach the semifinals at a Major since Jiro Sato in 1933 French Championships (now French Open). Nishikori then defeated world No. 1 Novak Djokovic in the semifinals to become the first Asian man ever to reach a Grand Slam tournament final. (As reference, an American male tennis player of Asian descent Michael Chang reached the final of Grand Slam to win French Open at the youngest age of Grand Slam history, and the finalist to be Runner up in both US Open and Australian Open.) In the final, Nishikori lost to Marin Čilić. Nishikori's run at the US Open saw his singles ranking improve to world No.8. Nishikori began the Asian Swing by entering the Malaysian Open as first seed and won for a third season title, beating Julien Benneteau in two sets. Nishikori then went on to participate in the Rakuten Japan Open and won the