Jack Draper's start to the clay-court season began in disappointing fashion as he retired injured late in the deciding third set of his first-round match against Argentine Tomas Martin Etcheverry at the Barcelona Open.
Despite winning the first set in his first match since his second-round exit from the hard-court Miami Open on March 20, Draper struggled with his movement thereafter and had tape applied below his right knee by a physio in the break between second and third sets.
But after losing the second set 6-3, Draper had just been broken for the second time and trailed Etcheverry by 4-1 in the third before withdrawing from the match.
Draper, ranked one place higher than his opponent in the ATP rankings, had started promisingly to take the first set 6-3 but was clearly hindered with his knee from the start of the second set as Etcheverry, who had last week taken world No 2 Carlos Alcaraz to three sets on the clay in Monte Carlo, soon took control.
"He was playing unbelievable," said Etcheverry.
"He is a great competitor. I liked how he plays. He's a great fighter and hopefully he can recover as soon as he can to get back on tour because the tour likes him."
Barcelona had represented only Draper's fourth tournament back on the ATP Tour since a left-arm injury had kept him sidelined since last August's US Open, with Etcheverry representing the eighth match of his return.
He is next due to play at the ATP Masters 1000 event in Madrid from April 22, where he reached the final last year before losing to Casper Ruud.
Etcheverry will now play either Portugal's Nuno Borges in the second round at Real Club de Tenis Barcelona.
British No 1 Cameron Norrie came through a gruelling two-and-a-half-hour three-setter against three-time Grand Slam champion Stan Wawrinka to book his place in round two.
Norrie won the opening set 6-4 but the 41-year-old Wawrinka - who was awarded a wild-card entry for the tournament amid his final year on tour before retirement - took the second on a tiebreak to take the match into a decider.
But Norrie emerged on top thanks to the only break of serve in the third set to secure a 6-4 6-7 (5-7) 6-4 triumph.
The number seven seed will now play American Ethan Quinn in round two.
"I was not really feeling that well today physically, so I had to really dig deep mentally," said Norrie.
"I had to dig deep and get fired up in some moments and I managed to do that in the third set when I was a couple of break points down."
Katie Boulter eased into the last 16 of the Rouen Open with a dominant 6-2 6-2 win over Maria Timofeeva.
The British No 3 bounced back from last week's tight first-round defeat to Elena-Gabriela Ruse in Linz with a dominant display against the current world number 153.
With many top players choosing to play in Stuttgart this week, Boulter is targeting a good run in Rouen, and potentially a first clay court title of her career.
A projected third round meeting against former grand slam winner Sloane Stephens was scuppered when the American was thrashed 6-2 6-1 by Ukrainian Veronika Podrez, who was making her WTA main tour debut.
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