Eintracht Frankfurt beat Rangers 5-4 on penalties to lift the Europa League title and win their first European trophy in 42 years.
Eintracht goalkeeper Kevin Trapp saved substitute Aaron Ramsey's spot kick - Rangers' fourth - while Eintracht were flawless in their execution, scoring all five. The game had finished 1-1 after 120 minutes.
Joe Aribo had struck against the run of play in the 57th minute to give Rangers the lead, charging clear after a string of defensive errors and sliding the ball past Trapp.
The Germans, unbeaten in the competition going into the final and eyeing their first European title since 1980, bounced back as Rafael Borre turned in a Filip Kostic cross in the 70th minute.
The win also means Eintracht will be competing in next season's Champions League despite finishing in 11th place in the Bundesliga.
It was Rangers’ 19th game in Europe this season and Giovanni Van Bronckhorst’s side now have to get themselves ready for the Scottish Cup final against Hearts at Hampden Park on Saturday.
Distraught Rangers midfielder John Lundstram told BT Sport: "It's a hard one to take, to lose on penalties. In the 120 minutes both teams didn't perform great.
"I thought we could have performed better. It's heartbreaking. We could've won it. I'm absolutely devastated. I'm so, so, so heartbroken."
Teammate Steven Davis added: "It's huge disappointment. It's hard to reflect straight away.
"The boys have been tremendous, but it hurts tonight. Unfortunately we were on the wrong side of [the penalties]. Whenever you get to a final it hurts if you don't come away with the trophy.
"But I couldn't be more proud of the lads, staff and fans. We left everything out on the pitch. It's going to be a sore one to take. We know how difficult it will be to get to this stage again."