Rangers have been knocked out of the Europa League at the quarter-final stage after being defeated by Athletic Club.
The La Liga side ran out 2-0 winners in the San Mames in Bilbao on Thursday night to take their place in the last four of the competition.
After a 0-0 draw at Ibrox last week, Oihan Sancet opened the scoring from the penalty spot before Nico Williams secured victory with a header late in the second half.
Rangers had their first sight of goal in the opening stages when James Tavernier sent an ambitious free-kick over the crossbar.
They had to weather a bit of a storm after that with the home side pushing for an opener and Liam Kelly did well to deny Williams before Tavernier made a vital block to keep out Sancet with the rebound.
Cyriel Dessers had a penalty claim up the other end when his shirt was tugged inside the area at the end of a Rangers counter attack.
The referee waved play on and the forward was eventually booked for his demonstrations despite showing a rip down the middle of his shirt as proof of an infringement.
Athletic Club continued to dominate possession for the rest of the half and created a host of opportunities, but without really testing Kelly.
Rangers continued to ride their luck and absorbed all the pressure thrown and looked like they had done enough to keep the game and tie goalless going into the break.
However, the home side came close when the ball fell to Sancet inside the box in injury time, but he put it over the bar under pressure from Kelly.
Then, just moments later, Athletic were awarded a penalty in the dying moments of the half when John Souttar clipped Maroan Sannadi inside the box.
Sancet stepped up and sent Kelly the wrong way to give Athletic Club a vital 1-0 lead to take into the second half.
Barry Ferguson made a change at the break when he replaced Ianis Hagi with Clinton Nsiala before he was forced into another after the restart when Leon Balogun clashed heads with Souttar and had to be taken off for Hamza Igamane.
Rangers came inches away from an all-important equaliser just before the hour mark when the ball fell to Nico Raskin right in front of goal, but his effort came off the goalkeeper before hitting the post.
They were now starting to look more dangerous as they chased a leveller and Vaclav Cerny was involved in two good moves.
Firstly, the Czech winger got down the line after good play by Diomande, but his chipped cross was cleared out for a corner before it reached Dessers.
He then tested Julen Agirrezabala with a well-struck effort from outside the box, but the home side remained in front.
However, Athletic grabbed the killer second goal with ten minutes remaining when Williams smashed a bullet header past Kelly to make it 2-0.
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