year. He had a slow start with only a first round at the Chennai Open and the final stage of Australian Open qualifications, as well as failing to reach the main draw at Open Sud de France and Open 13. His following matches were on the Challenger Tour, making it to the quarterfinal in Cherbourg and later the final of Jonkoping and the quarterfinal in Kazan. He then entered the qualifications for Monte Carlo as his first clay Masters 1000 appearance. He lost to Taro Daniel in the first round. The following week he qualified for the Barcelona Open, beating Ramkumar Ramanathan and Marco Trungelliti. In his first-round match he came back from a set down to beat Aljaz Bedene. In the second round he beat fifth seed Roberto Bautista Agut, also in three sets. He eventually lost in the third round to the eleventh seed Alexandr Dolgopolov. Right after that he played at the Istanbul Open as a wildcard player. In his first match, he beat Aljaz Bedene for the second time in the month. In the following round, he lost to Albert Ramos Vinolas, despite winning the first set. He then continued with good results at Challengers, reaching the quarterfinal in Karshi and winning the title in Samarkand the following week. Playing in the qualification of the French Open, Khachanov completed his appearances at all four Grand Slams, but with no qualifications into the main draw. Two Challenger semifinals in Prostejov and Moscow followed, as well as another loss in the qualifications of Wimbledon. In July, at the Kitzbuhel Open, he defeated Filippo Volandri and Philipp Kohlscreiber to reach his first ATP Tour quarterfinal since the 2013 Kremlin Cup, before losing to Dusan Lajovic. At the US Open, he made his main draw debut after passing the qualifications. In the first round he recorded his first Grand Slam win, over Thomas Fabbiano, but lost in the second round to Kei Nishikori. After that, he lost in the first round of the St. Petersburg Open to Alexander Zverev. However, he progressed further the following week at the 2016 Chengdu Open. He defeated Joao Sousa, Adrian Mannarino, Feliciano Lopez and Victor Troicki to reach his first ATP Tour final. By reaching an ATP singles final, Khachanov became the first Russian in an ATP Tour final since Mikhail Youzhny, who beat David Ferrer in the final at the 2013 Valencia Open