Mikhail Youzhny's tennis career has come to an end after losing over three sets to Roberto Bautista Agut in the second round of the St Petersburg Open.
The 36-year-old Russian had already announced his intention to bow out at the end of his home tournament, and was denied a 500th career victory by the fifth seed on Thursday.
After losing the first set on a tie-break, 2008 Australian Open quarter-finalist drew level before Buatista Agut finished off a 7-6 (8-6) 3-6 6-3 win to book his spot in the quarter-finals.
Youzhny was also a semi-finalist at the US Open in 2006 and 2010, and a quarter-finalist at the French Open in 2010 and Wimbledon in 2012.
Top seed Dominic Thiem joined the Spaniard with a straight-sets win over Jan-Lennard Struff
The Austrian, French Open runner-up earlier this year, needed a tie-break to take the first set but eventually ran out 7-6 (7-4) 6-4 winner.
Italian third seed Marco Cecchinato, beaten by Thiem in the semi-finals at Roland Garros, was a 7-5 7-6 (8-6) winner over Lukas Lacko.
Canadian seventh seed Denis Shapovalov needed three sets to get past Matteo Berrettini 7-6 (8-6) 4-6 6-0, while Daniil Medvedev defeated Mikhail Kukushkin 6-3 6-4 and Damir Dzumhur sank Guido Pella 6-4 6-4.
Elsewhere Stefanos Tsitsipas was a shock second-round casualty at the Moselle Open in Metz.
The 20-year-old second seed from Greece, who last month beat four top-10 players including Novak Djokovic in Toronto, lost 6-7 (5-7) 7-6 (8-6) 6-3 to world No.103 Ricardas Berankis of Lithuania.
Benoit Paire went down 6-4 3-6 6-3 to Yannick Maden but Gilles Simon gave the French crowd something to cheer with a 4-6 7-5 7-5 win over Serbian seventh seed Filip Krajinovic.
