final in three sets on the hard courts of the Citi Open in Washington, D.C., after fighting from a set and a break down with Karlović serving for the championship in the second set, and moments later, saving a championship point in the tiebreak. The win was Monfils' first ATP World Tour singles title in over two years, although he had previously reached at least one final every year since 2005. All of his previous ATP World Tour singles titles came under the ATP World Tour 250 Series category, despite the fact that he had already reached at least 3 finals each across all categories, except Grand Slams and Tour Finals. The following week, Monfils reached the semifinals of the 2016 Canadian Masters after dispatching 2016 Wimbledon singles finalist Milos Raonic in the quarterfinals, to set up a tie against world No. 1 Novak Djokovic, to whom he lost in straight sets, ending his career-best win streak of 9 consecutive matches. In the second week of August, since Richard Gasquet withdrew from the 2016 Olympics tennis tournament because of an injury to his back, Monfils would pair up with Jo-Wilfried Tsonga in the men's doubles draw. In the men's singles draw of the same tournament, Monfils reached the quarterfinals and lost to eventual bronze medalist Kei Nishikori, despite having 3 match point chances in the deciding set. In late August, Monfils entered the 2016 US Open seeded tenth and reached the semifinals without dropping a set, defeating prominent past and present players on the tour Gilles Müller, Jan Šátral, Nicolás Almagro, Marcos Baghdatis and Lucas Pouille en route. He eventually lost a controversial match to Djokovic in four sets. The controversy came due to Monfils soft balling many shots and appearing that he was not giving the match his all. As a result, Monfils was jeered by the crowd and criticized by John McEnroe, who claimed that he was "unprofessional". In the first week of October, Monfils entered and was seeded second at the 2016 Japan Open, another ATP World Tour 500 Series tournament, where he also reached the semifinals without dropping a set, after again beating Ivo Karlović in the quarterfinals to set up a tie against eventual champion Nick Kyrgios, whom he lost to in two very competitive and entertaining sets. Monfils then entered the Shanghai Masters seeded sixth and received a bye into the second round, where