LONDON — Canadian tennis player Denis Shapovalov had his losing streak extended to five matches Wednesday with a 6-4, 2-6, 6-4 loss to Tommy Paul at the Queen's Club grass-court event.

Shapovalov hasn't won since a May 12 upset of clay-court legend Rafael Nadal in the third round of the Italian Open.

The Canadian lost in the quarterfinals in Rome to then world No. 10 Casper Ruud.

He then dropped his first match of his next four tournaments to Ilya Ivashka of Belarus (ranked 50th); Denmark's Holger Rune (40), Germany's Oscar Otte (61) and Paul (35).

Shapovalov, from Richmond Hill, Ont., is ranked No. 15 in the world, but Wednesday's loss dropped his 2022 record to 16-13.

He had 11 aces against Paul but made six double-faults.

Shapovalov broke Paul twice on nine chances. The American was more efficient with his opportunities, converting two of his four break chances.

Paul improved his career record against Shapovalov to 2-0.

The Queen's Club event is a warm-up for Wimbledon. The grass-court Grand Slam starts June 27 at London's All England Club.

Shapovalov was a semifinalist at Wimbledon last year.

This report by The Canadian Press was first published June 14, 2022.