Eintracht Frankfurt broke Rangersβ hearts, as they won the Europa League final on penalties, after Aaron Ramsey's spot kick was saved.
The two sides needed a shoot out to decide the winners in Seville, after they had shared goals in the second half of normal time and couldn't separated after 120 minutes of football.
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Joe Aribo put the Scottish side ahead in the 57th minute, thanks to a slip from Tuta in the build up to the goal, with the Frankfurt defender having to be subbed off straight after with an injury.
The lead lasted just 12 minutes for the Gers, as Rafael Santos Borre equalised in the 69th minute, as he managed to get between two defenders and tap in past Alan McGregor.
After a goalless extra 30 minutes it went down to the shootout, with the Rangers fans behind the goal creating an incredible atmosphere.
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James Tavernier, Steven Davis, Scott Arfield all slotted home for Giovanni van Bronckhorst's side, with the German's takers matching them, before Ramsey, who had been brought on in extra time just to take a penalty, had his dreadful effort was saved by Kevin Trapp's legs.
Borre scored the final penalty to win the shootout 5-4, and hand Rangers their second loss in the final, having lost the UEFA Cup final in 2008.
It was Frankfurt's second trophy in Europe, having also won the UEFA Cup in 1980.
There was an incredible atmosphere inside the Ramon Sanchez-Pizjuan Stadium, with fans of both teams well known for their ardent support.
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Over 100,000 Rangers fans had turned up in Spain, including injured striker Alfredo Morelos, and there was just as vociferous a following from Germany.
Controversy came in just the sixth minute, as John Lundstram's made contact with Sebastian Rode's head, with the midfielder ducking in for a header.
The referee surprisingly didn't even produce a yellow card for the semi final hero, when some might have even given a red, whilst Rode had to be bandaged up.
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Frankfurt, who'd beaten Barcelona and West Ham in previous rounds, then took control of the first half, and McGregor was certainly the busier of the two keepers.
Rangers did begin working their way into the game as the half progressed but neither side could fashion a good enough chance to worry either keeper.
Frankfurt thought they should have had a penalty in the 53rd minute, when it appeared there was a trip in the box, but the referee just gave a corner.
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Four minutes later they would have been damning their luck, as Tuta slipped and Aribo was able to slot home following a header from Djibril Sow.
Borre equalised when he managed to nip between Connor Goldson and Calvin Bassey, who had a brilliant game, to tap home from Filip Kostic's cross.
In extra time Trapp had to make a brilliant save with his legs, when it looked like Rangers were going to take the lead, and Tavernier put a free kick wide.
Ramsey came on late in the additional 30 minutes for Fashion Sakala, who had come on in the 74th minute, to take a penalty but ultimately it was his miss that lost the final.
Featured Image Credit: PA/BT SportTopics:Β Rangers, Scotland, Europa League, Eintracht Frankfurt, Bundesliga, Germany, Scottish Premiership
