reaching the quarterfinal again in the Miami Open by beating Pierre-Hugues Herbert, Alexandr Dolgopolov and Roberto Bautista Agut in straight sets. He then reached the semifinals of the tournament for the second time in his career after saving five match points and beating Gaël Monfils in a comeback three-set match. He then reached his second final in a Masters 1000 after dismantling Nick Kyrgios in straight sets. He lost to then world No. 1 Novak Djokovic in the final in straight sets. For the 5th consecutive year, Nishikori did not play in Monte Carlo and instead turned his focus to defending his Barcelona Open Banc Sabadell title. He reached the final without losing a set, but lost in straight sets to resurgent nine-time champion Rafael Nadal in the final. He followed his good run by reaching the semifinals in the Mutua Madrid Open, beating Fabio Fognini, Richard Gasquet for the first time in 7 meetings and rising teenage star Nick Kyrgios. He lost in the semifinal to Novak Djokovic in straight sets despite a close 2nd set. Nishikori then replicated his Madrid run by reaching the semifinals of the Italian Open for the first time after beating Viktor Troicki in the opener in three sets, followed by wins over Richard Gasquet and Dominic Thiem in straight sets. He lost in the semifinal against world Novak Djokovic in a marathon 3 hours three-setter despite winning the first set 6–2 and managed to pull off a tiebreak in the third set. He later participated at the French Open but lost to an in-form Gasquet in the fourth round in 4 sets. Nishikori began his grass season at the Halle Open, but retired in the 2nd round due to a hip injury. His next tournament was at Wimbledon, where he retired in the fourth round against Marin Čilić, once again due to injury. With Murray, Federer and Nadal absent, Nishikori was seeded 3rd for the Rogers Cup Masters in Toronto. After beating Grigor Dimitrov and Stan Wawrinka in the quarterfinals and semifinals respectively, Nishikori then lost to Djokovic in straight sets in the finals, going 0–5 so far in the season against the Serb. Nishikori then participated in the 2016 Summer Olympics, where he reached the semis before being defeated by World No. 2 Andy Murray in straight sets. However, he later acquired the bronze medal after he defeated Rafael Nadal 6–2, 6–7