Montreal’s Felix Auger-Aliassime fell in straight sets to Japan’s Yosuke Watanuki at the Citi D-C Open in Washington.
Auger-Aliassime has struggled through injuries this season and spoke recently about his determination to recover from them.
He was the third seed in the tournament and now heads to Canada to take part in the National Bank Open, a tournament he has never won.
Gabriela Dabrowski, of Ottawa, Ont., and her doubles partner Shuko Aoyama won their doubles matchup against Erin Routliffe and Ingrid Neel.
The pair won straight sets against their opponent (6-3, 6-2) in the round of 16.
Leylah Fernandez, of Montreal, Que., is set to play Greece’s Maria Sakkari in the round of 16 on the women’s singles side of the tournament.