The anguish of Stefanos Tsitsipas continue as the Greek star was pushed out in the ATP 500 clay court event only days before the Olympics.
The world number four came into the German tournament as as favourite to claim a third title of 2021 and put a disappointing Wimbledon behind him.
He started well to dispatch Dominik Koepfer 7-6, 6-3 to reach the quarter-finals before coming up against sixth seed Filip Krajinovic.
The Greek won the the first set 6-3, by then Stefanos was deterred by his Serbian opponent and lost the next two sets 6-1, 6-3 to be unceremoniously dumped out.
In the first set, Tsitsipas took two of three break point chances presented to him, but only had one break chance throughout the rest of the match, and was unable to take.
Krajinovic only maintained his opportunities to challenge the Greek as the match went on, claiming two of three and two of four break point chances in sets two and three respectively.
Tsitsipas will have been looking to recapture some form before heading off to the Tokyo Olympics in search of a medal for his home country of Greece.