Darmstadt are the first Bundesliga club to be relegated to the second division this season after a late 1-0 defeat at home to Heidenheim.
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Despite having three games left, Darmstadt can finish no higher than 17th in the table and can't avoid their fourth relegation from the Bundesliga.
"It's difficult. Right now I'm feeling empty inside. There were a few games that could have gone our way this season, but right now I don't know what to say," midfielder Fabian Nurnberger, visibly shaken, told broadcasters DAZN after their Sunday defeat.
Darmstadt returned to the Bundesliga last year for the first time since 2016-17, but their comeback to the top tier has been disappointing, with 20 defeats and only three wins in 31 games so far.
Nikola Dovedan scored Heidenheim's winner in the 90th minute. With the win, Heidenheim, who were also promoted last year, have taken a crucial step in ensuring they will play in the Bundesliga next season.
Earlier on Sunday, relegation-threatened Cologne claimed a dramatic late 1-1 draw in a Bundesliga six-pointer at Mainz, while lowly sides Borussia Monchengladbach and Union Berlin played out a goalless draw.
A goal from Leandro Barreira in the 29th put Mainz ahead but the visitors equalised in stoppage-time with a penalty from Florian Kainz.
Both teams remain in the drop zone, Mainz in the play-off spot with Cologne right behind them.
In Gladbach, Union came close to a winner when Kevin Volland hit the crossbar in the 25th minute.
Gladbach had a huge chance to score in the last minute, but Marvin Friedrich's header from a corner was saved by Frederik Ronnow.
Gladbach are 13th with four points separating them from the drop zone. Union are one position behind and two points above the danger zone.
Australian Associated Press
