Thanasi Kokkinakis is out of the ATP tour event in Den Bosch in the Netherlands.
The 21-year-old Australian, on the comeback trail after missing more than a year through abdominal and shoulder injuries, lost 6-3 7-6 (7-3) to Daniil Medvedev of Russia.
Kokkinakis claimed his first Tour win since August 2015 on Tuesday when he beat Medvedev's countryman Mikhail Youzhny in the first round.
Top seed Marin Cilic survived a scare after dropping the opening set to Serbia's Janko Tipsarevic in a tiebreak.
The Croatian won 6-7 (7-6) 6-2 6-4, while compatriot and third seed Ivo Karlovic had an easier route to the third round, disposing of Stefan Kozlov 6-4 6-1.
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