Canadian Denis Shapovalov dropped the flag in the Doha Championship quarter-finals on Thursday. The seventh seed in Qatar slid in three groups 7-5, 3-6 and 5-7, ahead of American Taylor Fritz.

The winner of the first three duels, Shapovalov failed to keep a clean record against Fritz. Ontario scored 12 aces and committed 5 double faults, while California scored 11-2 in that regard.

Shapovalov stood twice instead of defeating Fritz in the tenth game of the last round when the American managed to finish the match. However, the world’s 11th batsman immediately lost his service to reclaim the 6-5 advantage of his rival, the 33rd seed, who ended the controversy over his third chance.

Prior to his debut at the Doha Championships, Shapovalov performed in Melbourne earlier this year for the ATP Cup and the Australian Open. He lost both of his matches in the team event and reached the third round of the first round of the Grand Slam tournament.

Fritz will meet the winner of the match between Roger Federer (No. 2) and Georgian Nikoloz Basilashvili in the quarter-finals. The Swiss maestro resumed wearing the collar on Wednesday, after a hiatus of more than 13 months to recover from two right knee operations.

The other semi-final will face Russian Andrei Rublev (No. 3) against Austrian Dominic Tim (No. 1) or Spain’s Roberto Bautista Agut (No. 5). Roblev took advantage of the withdrawal of Hungarian Marton Vosovic to advance to the next round.