During the grass season, he played only two tournaments. First, he advanced to the quarterfinal of the Halle Open for the second year in a row. Second, he reached the fourth round of Wimbledon, but then lost to Novak Djokovic. In the North American summer hard-court swing, Khachanov reached the semifinals of a Masters 1000 tournament for the first time in his career at the Canadian Open, losing to Nadal. He again lost to Nadal at the US Open in a marathon third round match. Khachanov then helped Team Russia to progress through the 1st Round play-off of the Europe/Africa Zone Group I by winning both matches and securing Russia a place in the World Group. In Asia, Khachanov struggled to find form. He reached only the second rounds of Beijing and Shanghai. He then rebounded at the Kremlin Cup, winning his second ATP title of the season by defeating Adrian Mannarino in the final. In the semifinal he defeated his compatriot Daniil Medvedev. Khachanov finished the year by claiming his first ATP Masters 1000 title at the Rolex Paris Masters, defeating Filip Krajinović, Matthew Ebden, world No. 9 John Isner (saving two match points), world No. 5 Alexander Zverev, world No. 8 Dominic Thiem and world No. 1 Novak Djokovic. He was the first tennis player representing Russia to win a Masters 1000 final since Nikolay Davydenko, who won the inaugural 2009 Shanghai Masters. No. 18 Khachanov was the lowest-ranked player to win a Masters 1000 title since Ivan Ljubicic took the 2010 Indian Wells Masters. As a result, Khachanov climbed to world No. 11 and was an alternate at the 2018 ATP Finals. He became the fifth Russian tennis player to win a Masters tournament after Marat Safin, Andrei Chesnokov, Yevgeny Kafelnikov and Nikolay Davydenko. 2019: First Major quarterfinal at the French Open, top 10, poor year-end season Despite starting the season as the 11th ranked player in the world, Khachanov struggled to achieve any notable results for the first five months of the season. Leading up to the French Open, Khachanov's record for the year was ten wins and twelve losses, and he had failed to reach a single tournament semifinal. At the French Open, Khachanov won his first three rounds to set up a last-16 encounter with Juan Martín del Potro. Khachanov beat del Potro for the first time to reach his first major quarterfinal, where