Rangers suffered Europa League heartache as Frankfurt won 5-4 on penalties in Seville.
Kevin Trapp was the penalty shootout hero as he saved Aaron Ramsey's crucial spot-kick.
Joe Aribo grabbed the opener just before the hour before Rafael Santos Borre levelled 12 minutes later to force extra-time.
Ryan Kent was denied by an incredible Trapp save with just two minutes to play in the additional period to force the match to a shootout.
And it was the Bundesliga outfit who triumphed on the night to send their fans crazy at the Ramon Sanchez-Pizjuan Stadium.
Sign up to Glasgow Live newsletters for more headlines straight to your inbox
Victory will gain the German side direct entry to the Champions League group stages as a top seed.
They will also earn a crack at Liverpool or Real Madrid in the Super Cup.
