Stan Wawrinka's distinguished clay-court career came to an emotional end after the three-time Grand Slam champion suffered a 6-4, 4-6, 6-3 first-round defeat to Argentina's Roman Andres Burruchaga at the Millennium Estoril Open.
Playing the final clay tournament of his career before retiring at the end of the season, the 40-year-old Swiss battled for two hours and 28 minutes and showed glimpses of the form that made him one of the sport's most dangerous players on the surface.
Wawrinka saved three match points in the deciding set to keep his hopes alive, but Burruchaga stayed composed to convert his fourth opportunity and secure one of the biggest victories of his career.
Following the match, Tournament Director Joao Zilhao presented Wawrinka with a commemorative gift to mark his final appearance on the Estoril clay.
"I grew up on clay, so it has always been a special surface for me," Wawrinka said after the match. He finishes his ATP Tour career on clay with an impressive 202-124 win-loss record.
Burruchaga will next face fifth seed and home favourite Nuno Borges, who opened his campaign with a comfortable 6-3, 6-3 victory over Brazilian qualifier Orlando Luz.
The win also saw Borges become only the second Portuguese player to record five match victories at the Estoril Open, joining former champion Joao Sousa.
Elsewhere, 2017 Estoril champion Pablo Carreño Busta eased past Lithuania's Vilius Gaubas 6-1, 6-3 to book a second-round meeting with France's Luca Van Assche.
There were also wins for lucky losers Kyrian Jacquet and Timofey Skatov. Jacquet recovered from a set down to beat last week's Umag champion Daniel Merida 1-6, 6-1, 7-5, while Skatov rallied past Jesper de Jong 1-6, 6-4, 6-3.
Skatov's reward is a second-round clash against top seed and Bastad champion Andrey Rublev.
