Denis Shapovalov missed a glorious opportunity to end a skid on Monday.
The Canadian was up a set and 3-0 in the second before losing 6-7 (5), 6-4, 7-5 to Croatian veteran Marin Cilic in the first round of the Libema Open in the Netherlands.
Shapovalov, who also was up a break in the third set, has now lost five matches in a row.
His grass-court season debut looked like it was going to result in an elusive victory, but Shapovalov couldn’t finish things off against the 2014 U.S. Open winner.
Shapovalov’s ranking has dropped to No. 42. Cilic is 47th.
Meanwhile, Canada’s Bianca Andreescu lost 6-1, 6-2 to No. 3 seed Elise Mertens of Belgium in the first round on the women’s side.
Andreescu’s ranking has fallen to No. 158.