World No. 28 Karen Khachanov of Russia failed to reach the second round of the Montreal Masters. Khachanov lost to Croatian Marin Cilic 3-6, 2-6. The match lasted one hour and 26 minutes.
Chilic's next opponent will be Tommy Paul, who knocked out Spaniard Carlos Alcaraz.
The Montreal tournament has a prize fund of $5.9 million.