Rangers suffered one of their worst ever results as they were knocked out of the Europa League qualifiers by Luxembourg minnows Progres Niederkorn.
The Ibrox side took a 1-0 first-leg lead to Luxembourg but fell behind to a second-half Emmanuel Francoise finish.
Sebastian Thill sealed progress, scoring only the third European goal in the minnows’ history to secure their first ever win in Europe.
Niko Kranjcar, Josh Windass and Kenny Miller hit the woodwork for Rangers.
But the Ibrox men had failed to dominate the game the way they had in the first leg, ensuring their first foray into Europe for six years was short-lived as they went out in the first qualifier.
Boss Pedro Caixinha brought Daniel Candeias, Alfredo Morelos and Jordan Rossiter into his starting line-up as he looked for more of a cutting edge in the second leg.
The visitors had the bulk of the early possession but again lacked the final pass that could punish Progres.
Miller had a shot blocked following a Kranjcar corner but it was all too untidy in the last third.
That seemed to give the hosts the confidence they had lacked in the first half at Ibrox, with Olivier Thill curling a long-range free-kick narrowly wide with goalkeeper Wes Foderingham struggling to get across.
Miller was inches away from connecting with a Lee Wallace cross but it was at the other end where the chances started to come.
Mike Schneider hit one over the bar when in a good position before the home side came very close. Olivier Thill drove forward and fired a long-range shot that had Foderingham beaten but slid just wide.
The second half started with Progres going even closer, this time Francoise bursting clear on the right and drilling a low effort towards the corner that Foderingham saved brilliantly.
As the second half wore on the home side looked the more threatening, with a few nerves evident in the visiting defence.
Home keeper Sebastian Flauss had gone off injured in the first half but Rangers failed to test stand-in Charly Schinker until after the hour, when Ryan Jack’s close-range header was directed straight at him.
Moments later Caixinha’s side almost grabbed a crucial away goal as Wallace sent in a cross that Kranjcar headed off the bar.
Then came the opener for Progres as Olivier Thill crossed for Francoise to finish at the near post.
The second arrived soon after as Sebastian Thill curled a free-kick into the box that evaded everyone and crept in at the back post.
Rangers rallied in the closing minutes with Windass’ diving header coming back off the bar before Miller, in stoppage time, lobbed an effort off the face of the bar.
There was no way through though, and the visitors slumped to a shocking result.
Analysis of Rangers’ shock Euro exit
BBC Scotland senior football reporter Chris McLaughlin
“For the Rangers fans it’s humiliating. For the players, humbling, and when the dust settles on what some are calling the worst result in the club’s history there will be huge questions to answer for the Rangers board and manager Pedro Caixinha.
“Where some saw the appointment of the Portuguese last year as a gamble, the Ibrox board believed it to be progressive. They had patience in their man despite a poor start to his managerial career in Scotland. They backed him with significant funds to rebuild and get Rangers back to where they wanted to be. And where they wanted to be was the group stages of the Europa League.
“Now that has gone, they must count the cost. Caixinha’s squad may well improve and they may even go on to close the gap on Celtic in the season ahead, but falling at the first hurdle in Europe is a massive blow financially and psychologically.
“Chairman Dave King has continually pointed to funds gained through European football as being key to them closing the gap on their rivals and now that badly needed revenue stream has gone before the season has even started. Only those providing the loans will know the true cost and implications of that.
“It’s not the only thing being cut unexpectedly though. The window of goodwill for the new manager has just been slashed drastically. Caixinha needs a blistering start to the season or he and his new recruits could be under serious pressure.”