Denis Shapovalov knows a thing or two about pulling off stunning upsets. On Wednesday, the Canadian teenager found himself on the wrong end of one.
After what was considered a very successful clay court season, Shapovalov's transition to grass wasn't as smooth, as he lost to world No. 169 Prajnesh Gunneswaran 6-7(8), 6-2, 3-6.
The competition at Stuttgart is Gunneswaran's first ATP World Event.
From the onset, there were warning signs that Shapovalov, now ranked 23 in the ATP, was in danger. He was immediately broken at the match's open, before Shapovalov bounced back with two breaks of his own to play his way into a first set lead. But Gunneswaran fought back and pushed into a tiebreak.
Shapovalov took a 5-4 lead there, with a chance to finally put Gunneswaran away, but the Indian won four of the final five points, taking it 8-6 to win the first set.
The second was rudimentary for Shapovalov, who bounced back and easily took it 6-2, forcing a third and decisive set for the right to move on to the second round.
Things again went south for Shapovalov there though, broken twice early and combined with three Gunneswaran holds, down 5-0. Shapovalov managed to break and consolidate to cut his deficit to 5-2, but a final Gunneswaran hold ended Shapovalov's day and tournament much earlier than expected. Shapovalov was seeded sixth overall in Stuttgart. Gunneswaran needed to win a qualifying match on Sunday to earn an appearance in the main draw.
Shapovalov put only 53-percent of his first serves in play, and hit only eight aces during the three sets, while double-faulting five times.
Elsewhere in the tournament, Milos Ranoic defeated Mirza Bašić in straight sets to advance to the second round.