Rangers suffered Europa League final penalty heartache as Eintracht Frankfurt edged them out on spot kicks to lift the trophy in Seville.
Aaron Ramsey saw his penalty saved by Kevin Trapp and the German side netted all of their penalties to secure the trophy after an evenly-contested final.
Joe Aribo gave Rangers the lead with his composed strike three minutes before the hour mark but Rafael Santos Borre levelled the tie up 12 minutes later with a poacher's finish.
Veteran Gers goalkeeper Allan McGregor impressively denied Ansgar Knauff in the 20 th minute and just after the half-hour mark, Filip Kostic fired a left-footed drive just wide of goal after a swift, decisive counter-attack.
Yet the Scottish side were not without their openings; Joe Aribo's long-range curler was just wide of the post while John Lundstram saw his header tipped over the bar by Frankfurt goalkeeper Kevin Trapp. However, the opening half was largely a cagey affair of few clear chances.
After the break, Frankfurt had a big penalty appeal turned down - Rafael Santos Borre went down under a challenge from Connor Goldson and while there was minimal contact, the Rangers defender did not win the ball. VAR looked at the call but decided not to tell the referee to take a second look.
Moments later, Rangers took the lead - a wayward back header from Djibril Sow allowed Aribo to break through and when Frankfurt defender Tuta slipped, it allowed Aribo to run straight through and coolly slot home the opener on the night to send the Scottish club's fans into bedlam.
Yet Frankfurt rallied and continued to create chances; midway through the second half Daichi Kamada's effort went narrowly over but two minutes later Santos Borre equalised, nipping infront of Goldson to score from close-range from a dangerous Filip Kostic cross.
The two sides could not be separated for the remainder of the encounter and the game ticked into extra-time. Rangers enjoyed the better chances and in the 116th minute, Ryan Kent was denied at point-blank range by Frankfurt shot-stopper Kevin Trapp before Steven Davis's follow-up effort deflected agonisingly over the bar. Which meant penalties.
Here are six talking points from a gruelling and dramatic night in Seville, which went all the way.
Finely balanced
Unlike most European finals there was no sense that this clash had an underdog or favourite to lift the trophy. Neither of these sides were fancied to reach the final.
Rangers may have been marginally the less favoured of the sides, but their eliminations of Borussia Dortmund and RB Leipzig - who both comfortably finished above Frankfurt in the Bundesliga standings - ensured that they had no shortage of confidence over the chances of taking another scalp.
This was played out during the match itself, with neither side being able to assert their authority on proceedings. Frankfurt enjoyed the better of the exchanges in the opening half-hour before the Scottish side came back into the encounter.
Yet the game was most notably a tense affair with both sides appearing to show if not nerves, then playing within themselves in fear of making an error that could cost their side the match.
McGregor's long wait ended
Allan McGregor was the Rangers goalkeeper in the 2007/08 season, but he was robbed of an appearance in the UEFA Cup final due to injury - as Neil Alexander stepped into deputise.
Since that season, he helped Rangers to win three league titles in a row, he then played at Cardiff City and Besiktas, spent five seasons at Hull City and then returned to Rangers, helping them to their first title in a decade.
Now he is aged 40 and starred on this season's run to the final, with the final in Seville his 104 th appearance in European competition for the Scottish club. This match was filled with plenty of incredible personal stories, but none topped that of the Gers goalkeeper.
Battle to end heartache
Both of these clubs have tasted European glory in previous days but neither side have lifted a continental trophy in the lifetime of any of the players on the pitch.
Rangers had lifted the Cup Winners Cup in 1972 (before losing the 2008 UEFA Cup showpiece against Zenit Saint Petersburg) while Frankfurt - who famously lost the European Cup final in Glasgow 7-3 against Real Madrid in 1960 - won the UEFA Cup, the predecessor of the Europa League, in 1980.
The broad similarities continued this season with both teams enduring disappointing domestic league campaigns; Rangers had seen Celtic wrestle back the Scottish league title while Frankfurt finished their season outside the top half of the Bundesliga, in a disappointing 11 th place.
Both Frankfurt and Rangers, who of course have a Scottish Cup final still to come against Hearts, were always going to be too tight to separate - so extra-time really was no surprise.
Hearts also winners
This was the first of two finals in the space of just four days for Rangers, who take on Hearts in this season's Scottish Cup final on Saturday with a 3pm kick-off.
Of course, the Edinburgh club will have wanted just one thing for this showpiece - that it went all the way to extra-time in an encounter which would be particularly draining for the Gers. The sight of Rangers players exhausted as the game ticked into added time would have brought no shortage of smiles to Hearts fans.
Gers away day blues?
One of the big narratives going into this game was that Frankfurt held an advantage due to their vastly superior away record in the competition compared to Rangers.
While the Scottish side's wonderful victory at Borussia Dortmund caught the eye earlier in the tournament, it was their only triumph across their eight away matches. The Gers failed to win on their travels to Alashkert, Sparta Prague, Brondby, Lyon, Red Star Belgrade, Braga and RB Leipzig.
By contrast, Frankfurt had won five of their six matches on the road - including most notably at Real Betis (in Seville), Barcelona and West Ham United. While Frankfurt excelled on the road, Rangers successes were built on their strong record at Ibrox - which they of course could not rely upon here.
As it turned out, that pre-match prediction ultimately did play out with the final outcome.
A final like no other
A reported 150,000 fans descended upon the Andalusian capital for tonight's encounter - despite each club having an allocation of just 10,000 tickets for the clash.
There was a party atmosphere across the city with the vast majority of fans in superb spirits and mixing amicably on the streets of Seville. These two clubs have significant followings and each have been starved of European successes in recent years.
The atmosphere inside the stadium was predictably incredible - with choreographs ahead of kick-offs with no shortage of noise, colour or atmosphere inside the Ramon Sanchez Pizjuan.
Frankfurt's eye-catching pre-match tifo cost a reported €50,000 and it took seven trucks to transport it all from Poland.