Rangers suffered an agonising penalty shootout defeat in their fifth European final as Eintracht Frankfurt triumphed in an absorbing Europa League decider.
Rafael Borre scored the decisive spot kick after former Arsenal player Aaron Ramsey missed the fourth penalty shoot-out to give Frankfurt the advantage.
Nigeria's Joe Aribo had put Rangers ahead in the second half before Rafael Borre equalized 12 minutes later to send the game into extra time.
And Rangers' players crumpled to their feet as the 11th-placed side in the Bundesliga prevailed in the shootout, executing five composed penalties to claim their second European trophy and a place in next season's Champions League group stages.
The win means Frankfurt will earn automatic qualification to the champions League next season after finishing 11th on the Bundesliga table.