Rangers lost the Europa League final in a penalty shootout to Bundesliga side Frankfurt in Seville.
Substitute Aaron Ramsey saw his kick saved by Kevin Trapp before Frankfurt forward Rafael Borre, who scored for the German side in normal time, fired home the winner.
James Tavernier, Steven Davis, Scott Arfield and Kemar Roofe all scored their spot-kicks, but to no avail.
Rangers had taken the lead in the 57th minute of normal time after Joe Aribo capitalised on a gift.
Djibril Sow made a poor decision to head the ball after meeting Conor Goldson’s header forward and the ball span backwards, allowing Aribo in behind and suddenly clear after centre-back Tuta slipped. The makeshift striker kept his nerve to slot home.
Frankfurt were level in the 69th minute when Filip Kostic delivered a low cross from the left which Connor Goldson failed to cut out and Borre got ahead of Calvin Bassey to knock home from six yards.
The 90 minutes finished 1-1 with extra-time to come. Frankfurt had the momentum after their equaliser but could not test Allan McGregor and Rangers had the territorial advantage in the latter stages of the 90 minutes.
Arfield came on for extra-time and soon went close from 25 yards.
Bassey redeemed himself with a brilliant recovery tackle following a slip.
Giovanni van Bronckhorst continued to leave Roofe and Ramsey on the bench as he brought on American midfielder James Sands as his fourth substitute before the first period of extra-time finished without any further scoring.
Borna Barisic and Ryan Kent forced saves and Frankfurt were off target twice from long range before the final entered the final five minutes.
Ramsey and Roofe came on in the 117th minute as Fashion Sakala and the injured Barisic made way.
Roofe soon created a great chance for Kent with a low cross but Frankfurt goalkeeper Trapp saved brilliantly with his foot and Davis had a follow-up shot headed off the line.
Trapp also saved Tavernier’s free-kick in stoppage-time to send the final to penalties.
Rangers won the toss to take the penalties at the end hosting their fans and Tavernier converted the opener before Christopher Lenz levelled the scores.
Davis then found the top corner before Ajdin Hrustic sent McGregor the wrong way to make it 2-2.
Arfield took a long run up before smashing the ball high into the net. Daichi Kamada made it 3-3 with a shot off the post.
Ramsey got his chance to make an impact but it was of the wrong variety as his penalty was saved by the boot of Trapp as he tried to go down the middle.
Kostic then squeezed his effort just inside the post to put the pressure on Roofe, who shot in off the post.
Borre stepped up and found the top corner to hand Frankfurt a 5-4 shoot-out win and end Rangers’ dream.
