It was a Thursday to forget for Canadian men's tennis.
Denis Shapovalov and Felix Auger-Aliassime were eliminated in the second round of the Terra Wortmann Open in Halle, Germany, while Gabriel Diallo lost a second-round match at Queen's Club in London.
Shapovalov, ranked 31st in the world, played the closest match, falling 7-6 (2), 6-4, 7-6 (5) to world No. 24 Flavio Cobolli at the grass-court tune-up for Wimbledon.
Shapovalov missed a chance to serve out the match up 5-4 in the third set.
Cobolli won his first two career ATP titles at clay-court events earlier this spring.
Auger-Aliassime, the world No. 27, fell 6-3, 1-6, 6-3 to No. 8 seed and world No. 22 Karen Khachanov of Russia.
The lifetime series is now tied at 2-2.
Diallo, the world No. 44, lost 6-4, 6-2 to the 30th-ranked Jiri Lehecka of Czechia.
The result snapped a six-match win streak for Diallo, who won his first career ATP tourney last week in the Netherlands.
Canada's Leylah Fernandez faces Ukraine's Dayana Yastremska in a quarterterfinal at the Nottingham Open in England on Friday.
There is one more week of tune-up events before Wimbledon starts June 30.
