Denis Shapovalov couldn’t get back to his winning ways on Monday afternoon, falling to Grigor Dimitrov 6-3, 7-6 (3) in the opening round of the ABN AMRO World Tennis Tournament in Rotterdam, the Netherlands.

Shapo fell behind early on, being broken in his first service game and trailing 3-0 before the match was 20 minutes old. He struggled against Dimitrov’s impressive return game, and was broken twice in the first set. Canadian fans were still treated to some vintage Shapovalov shot making, including this magnificent backhand winner.

The second set was much closer, with neither player giving an inch (or a break opportunity) throughout. Both players held serve all the way to the tiebreak, where a few unforced errors ended Shapovalov’s chances. He finished with 20 winners and 21 unforced errors in the match, while Dimitrov finished with a slightly tidier 19 winners to 17 errors.

The season’s first ATP 500 event wasn’t kind to Shapovalov; he had a better showing in last year’s edition, where he won two matches before eventually losing to Stan Wawrinka in the tournament’s quarter-final.

He’s still defeated two Top 10 players already this season, dispatching Alexander Zverev and Stefanos Tsitsipas at the ATP Cup in January.

He lost in the round of 16 at the Open Sud de France to countryman Vasek Pospisil last week, on route to the 29-year-old Canadian’s impressive run to the final.

This isn’t the end of the tournament for Denis though, as he’s set to make his doubles draw debut with partner Rohan Bopanna on Tuesday afternoon.

Speaking of doubles, Félix Auger-Aliassime won his doubles match with Hubert Hurkacz earlier in the day, 6-3, 7-6 (9). The duo outplayed Wesley Koolhof and Nikola Mektic in Felix’s first professional match in the Netherlands. He’ll make his singles debut on Tuesday afternoon against Jan-Lennard Struff.

Struff got the better of FAA at the ATP Cup in June, 6-1, 6-4 in the only match the two have played against one another.

If Auger-Aliassime can avenge his own loss, he’ll have a chance to then avenge close friend Shapovalov’s, with Dimitrov waiting in the round of 16.

Meanwhile, Pospisil will look to build on his early season success when he matches up against the tournament’s top seed Daniil Medvedev on Tuesday.

Shapovalov’s next singles opportunity will be at the ATP 250 event in Marseille next week.

(Feature photo: Open Sud de France)