Stefanos Tsitsipas crashed out of the Halle grass court tournament on Wednesday as top seeded Daniil Medvedev made the quarter-finals.
World number five Tsitsipas lost 7-6 (9/7), 7-5 to Chilean Nicolas Jarry, ranked 28 in the world.
It marks the third consecutive time the Greek has been knocked out in the second round of the Wimbledon warm-up tournament.
Medvedev defeated Serbian Laslo Djere 6-3, 6-7 (5/7), 6-3, with the world number three overcoming losing a tight second set to win with ease.
The former world number one and 2021 US Open champion was runner-up on the Halle grass in 2022, losing to Hubert Hurkacz in straight sets in the final.
Medvedev has struggled on grass in his career so far and has never reached the quarter-finals at Wimbledon.
He will next face Spanish eighth seed Roberto Bautista Agut.
He missed last year's tournament at the All England Club due to Wimbledon's ban on Russian and Belarusian players competing.
Medvedev has won five ATP titles already this year, but was beaten by Sebastian Korda in the Australian Open third round and was dumped out in the French Open first round for the fifth time in seven appearances.
Later on Wednesday, home favourite Alexander Zverev will take on Denis Shapovalov.
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