India's Prajnesh Gunneswaran picked up the biggest win of his career on Wednesday, beating World No. 23 and sixth seed Denis Shapovalov of Canada 7-6 (8-6), 2-6, 6-3 in the first round of the Mercedes Cup in Stuttgart. Prajnesh, who had risen to a career-high ranking of 169 on Monday, is playing in his first ATP World Tour event.
Prajnesh began by breaking Shapovalov's service in the very first game of the match, but then exchanged breaks at 2-1 up, before being broken again when serving for the set at 5-4. He would hold his nerve in the tiebreak, though, winning four of the last five points to take it 8-6.
The second set saw Shapovalov break Prajnesh twice to bring the match back on level terms, but Prajnesh began the decisive set by breaking Shapovalov twice to race away to a 5-0 lead. Up 5-1, Prajnesh was guilty of wasting four match points as he allowed his opponent a way back in the contest, but he would serve out the victory at 5-3.
Prajnesh will now face Guido Pella of Argentina in the round of 16, and a win over the 75th-ranked Argentine could set up a quarter-final clash against Roger Federer.
Last month, Prajnesh, who lost his third and final qualifying round match at the French Open to Elias Ymer, missed out on the main draw after Nick Kyrgios pulled out of the Grand Slam ahead of his first match against Bernard Tomic. Prajnesh had the chance to take Kyrgios' place, but he had already boarded a flight to play a Challenger tournament in Vicenza, Italy at the time.