Rangers' hopes of Europa League glory ended with penalty shootout misery as Eintracht Frankfurt secured the trophy in Seville.
The Ibrox side dreamed of lifting a European trophy for just the second time in the club's history but it is the Bundesliga side's name etched on this year's trophy after the match finished 1-1 after extra-time.
Joe Aribo sent Rangers into dreamland in the 57th minute when his shot crept over the line to open the scoring at the Ramón Sánchez Pizjuán Stadium.
Rafael Santos Borre stabbed home the equaliser for Frankfurt 12 minutes later after a mistake from Connor Goldson, sending the match into extra-time.
Both sides passed up opportunities in the extra 30 minutes before substitute Aaron Ramsey missed his spot-kick and the German side converted all of theirs as the Ibrox side fell short, just as they did in 2008.
How Rangers Europa League dreams ended in misery
Giovanni van Bronckhorst stuck with the same starting XI as their semi-final triumph over RB Leipzig at Ibrox as they looked to secure the club's first European trophy since 1972.
The first opportunity fell to the Bundesliga side when Rangers lost the ball in midfield. Daichi Kamada beat a couple of challenges before Allan McGregor blocked his close-range effort and quickly recovered to save Djibril Sow's follow-up.
Frankfurt were determined and had McGregor to thank again soon after as he produced a brilliant save to deny Ansgar Knauff.
Rangers, though, recovered to create their first real chance as a lovely pass from Scott Wright set up Aribo outside the box, but the midfielder watched his shot drift just wide of the post.
John Lundstram, Rangers' semi-final goal hero, produced their first shot on target as his header was tipped over the bar from Borna Barsic's free-kick.
Ryan Jack then had a chance to be a hero for the Ibrox side when the ball fell to him on the edge of the box, but he sent it sailing high over the bar.
It was Eintracht who continued to pressure after the break.
With McGregor beaten, only a deflection off Calvin Bassey denied Jesper Lindstrom the opener as his shot looped inches wide of the post.
The German side were screaming for a penalty after Goldson made contact with Borre on the edge of the area - a VAR check saw no spot-kick given.
Rangers then countered quickly as Tavernier burst down the right and sent a ball to Ryan Kent, who sent his effort into the stand.
But then out of nothing Rangers found themselves in front.
Aribo pounced on a misjudged header from Djibril Sow, chasing defender Tuta then stumbled giving the midfielder a free run on goal.
His strike crept past Kevin Trapp in the Frankfurt goal and sent the thousands of Gers fans inside the stadium into raptures.
Frankfurt were not giving up and, after Kamada's shot landed on the top of the net, Santos Borre equalised.
Goldson failed to clear Filip Kostic's corner and the striker stabbed the ball past McGregor.
With extra-time looming Kostic had a chance to win it for Frankfurt but, with too much power, the ball flew past the far post.
Scott Arfield watched his effort fly well over at the start of extra-time, then at the other end an error from Bassey allowed Borre to burst forward but the Rangers defender recovered to clear the danger.
It was Bassey to the rescue again soon after as he matched Knuaff for pace to cut the angle and force the winger to fire wide.
As players from both sides started to tire, Kent tried a speculative shot from distance but it posed no threat to the Frankfurt 'keeper.
Rangers then squandered a glorious chance to win it in the dying minutes of extra-time when Roofe's perfect cross found Kent but he could only fire his effort straight at Trapp from close range as the match went to penalties.
Tavernier, Steven Davis and Arfield made no mistake from the spot before Ramsey sent his effort into the arms of Trapp.
Rafael Borre then slammed home the decisive penalty to win the Europa League for Frankfurt and break the hearts of thousands of Rangers fans.
We are all hurting
Rangers manager Giovanni van Bronckhorst said it was a hard defeat to take after a momentous campaign:
"It is never nice to lose, everyone is hurt and disappointed.
"Aaron, of course, was disappointed but he took responsibility to take the penalty.
"You can make it or miss it and unfortunately for us he didn't make it but you want players taking penalties who are ready and comfortable also.
"If you play a lot of big games, big finals, we will have memories that last forever when you win them but when you lose it will hurt a lot."
Captain James Tavernier said it is a result that will be difficult to get over:
"Our dream tonight was to make everyone proud.
"We obviously didn't push it over the line, but the effort the boys put in I couldn't be more proud of them."
Scottish Cup final will refocus the players - Trevor Steven
Former Rangers player Trevor Steven was watching the final for Sky Sports News:
"I don't think Rangers played to their best, it was a war of attrition at times, but they could have easily won it in extra-time.
"There were opportunities, but that's football. Ramsey will be cast as the villain, but it has been a brilliant effort on a brilliant journey.
"It's so disappointing for the players to get this far, with the effort they've put in.
"How do they regroup? Reality will kick in very quickly and as a professional they have to mentally get back to Glasgow for a cup final, and they'll be pleased they've got something else to go for to focus their minds.
"Ramsey looked a bit tentative going up to the penalty, and he didn't strike it particularly well, and Trapp didn't have to do much to save it. But nine times out of 10 Ramsey would score.
"But this experience and journey has helped put Scottish football back on the map."