Rangers failed to reach the last 32 of the Europa League after they lost 1-0 to Rapid Vienna, with Dejan Ljubicic's late goal ending their hopes.
Steven Gerrard's men needed a win in Austria to send them into the knockout stages and they came close when a Connor Goldson header hit the bar in the 21st minute.
But a poor clearance from goalkeeper Allan McGregor eventually saw Ljubicic slot home in the 84th minute to knock Rangers out of the competition.
Rapid Vienna secured themselves a place in the last 32 with the victory, alongside Group G winners Villarreal, who beat Spartak Moscow 2-0 in the other fixture in the group.
It took 15 minutes for either side to have a shot as Borna Barisic went for goal with a low free-kick after Alfredo Morelos was bundled over, but it went straight into the hands of Rapid goalkeeper Richard Strebinger.
Six minutes later and Rangers hit the crossbar in what turned out to be their best chance of the game. Boli Bolingoli was penalised for a handball and the free-kick was curled into the box by captain James Tavernier. Goldson rose to meet it from six yards out, but his header smashed off the crossbar before bouncing clear.
The first half proceeded with little goalmouth action, but both goalkeepers were tested early in the second period. Strebinger was forced to claw away a Ryan Jack cross, before McGregor got his first real touch on the ball as Christoph Knasmullner struck, but the Rangers stopper got down low to make the save.
The game had a better flow to it in the second half, but chances remained at a premium, although Rangers did go close with nine minutes to play. Tavernier fired towards goal from 20 yards out, but Strebinger pushed it away. A cross was then put into the area not long after - intended for Kyle Lafferty - but the goalkeeper was there again to clear.
Rapid Vienna struck the hammer blow in the 84th minute which condemned Rangers to a Europa League exit. McGregor had little to do during the game but his fluffed clearance fell to Veton Berisha, who in turn found Ljubicic just outside the area. He played a neat give and go with Knasmullner before slotting the ball home and sending the hosts through to the last 32.
Man of the match - Christoph Knasmullner
It was an inspired choice to bring Knasmullner on at the break, and he had a big impact in the second 45 minutes. He had a great shot that tested McGregor for the first time not long after coming on and set up the winning goal. He will be one to watch out for in the next round.
Opta stats
- SK Rapid Wien have qualified through the group stages to the Last 32 of the Europa League for the first time since the 2015/16 season.
- SK Rapid Wien have won their first competitive game against Rangers having lost each of their previous three matches against them.
- Rangers have won just one of their 10 Europa League games since the competitions rebranding in 2009-10 (P10 W1 D6 L3).
- SK Rapid Wien have won back to back Europa League games for the first time since November 2015 (run of four).
- Excluding qualifiers Rangers have failed to win any of their previous 12 away European games (D8 L4) since a 2-0 victory in the quarter final second leg of the UEFA Cup against Sporting CP back in April 2008.
What's next?
Rangers will be back at Ibrox on Sunday when they host Hamilton in the Scottish Premiership. Rapid Vienna will also be in action on Sunday, playing Austria Vienna in the Austrian Bundesliga.