Rangers endured the agony of Europa League penalties as Frankfurt prevailed at Sevilla.
And it was a double whammy for the Light Blues as they missed out on guaranteed Champions League group stage football next season
If the Ibrox team had been successful in Spain, they would have gone straight into the groups as the top seed.
But tonight’s shootout loss means they will instead have to go through two qualifying rounds to get there.
The winners of the second European Cup competition are rewarded with a place in the following campaign’s Champions League.
But Giovanni van Bronckhorst’s men suffered heartbreak as Aaron Ramsey’s missed penalty proved costly after a 1-1 draw in 120 minutes.
Rafael Borre was Frankfurt’s hero as his kick drove the final nail into the coffin of Gers’ European hopes.
As they finished runners-up in the Premiership, they will take part in the third qualifying stage this summer.
Reaching the groups would bring in a windfall of at least £20million, with the figure increasing depending on the results when they get there.
Steven Gerrard’s side were dropped in the third qualifying round this season, with a 4-2 aggregate loss to Jon Dahl Tomasson’s Malmö.
Rangers haven’t made the Champions League groups since 2010/11, when they faced Manchester United, Bursaspor and Valencia, finishing third.
