Rangers suffered one of the biggest upsets in Scottish Cup history as second-tier Queen's Park secured a stunning 1-0 victory at Ibrox.
Seb Drozd's 69th-minute strike proved decisive in a match that saw Rangers lose at home to lower-division opposition in the cup for the first time ever.
The drama reached its peak in stoppage time when Rangers captain James Tavernier had his penalty saved by Queen's Park goalkeeper Calum Ferrie.
Boos echoed around Ibrox at the final whistle as the Championship side celebrated their first quarter-final appearance since 1928.
Rangers have suffered an embarrassing defeat in the Scottish Cup
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Rangers squandered numerous first-half opportunities, with Mohamed Diomande and Vaclav Cerny both denied by Ferrie.
Ianis Hagi saw his goalbound effort headed off the line by Jack Turner before the interval.
The visitors grew in confidence after the break, with Kyle Hurst nearly connecting with Ryan Duncan's low cross.
Queen's Park's growing threat materialised when Drozd broke the deadlock, dragging the ball towards the goal line before beating Jefte and firing through Liam Kelly's legs.
The goal sparked panic in the Rangers ranks as Philippe Clement's side struggled to find a response.
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The hosts pushed desperately for an equaliser, with Ferrie making crucial saves from Cyriel Dessers and Vaclav Cerny in the closing stages.
Rangers appeared to have salvaged their cup hopes when Dessers was fouled in the box deep into stoppage time.
However, Ferrie produced his most spectacular save of the afternoon, diving full-length to his left to deny Tavernier's spot-kick.
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Queen's Park goalkeeper Calum Ferrie was the hero for the away side
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The Queen's Park keeper had to endure an agonising VAR check before his heroic save was confirmed, securing his side's historic victory.
The defeat has intensified pressure on Rangers manager Philippe Clement, with the club now likely to end the domestic season without silverware.
"They built credit back over the last weeks and months with the fans but they lost everything of that credit. This is not acceptable to lose against Queen's Park in the cup," Clement told Premier Sports.
The Belgian manager remained defiant about his position, stating: "It happened several times in the past. We know it's a rebuild."
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Philippe Clement is fighting to save his job at Rangers
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"It's not because you lose a game you would normally win 99 times out of 100 that things change about the way things are working," he added.
Clement insisted axing him now would be "living in emotions" and destabilise the club.
Rangers now face a barren domestic season, trailing Celtic by 13 points in the Premiership and having already lost the League Cup final to their rivals in December.
Queen's Park celebrated wildly at Ibrox after their victory
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The Europa League remains their only path to silverware this term, with Clement's side having reached the last 16.
The match statistics highlighted Rangers' profligacy, with Clement noting they created "30 chances" but lacked "quality in those moments."
For Queen's Park manager Callum Davidson, watching from the main stand due to a touchline ban, this victory ranks as arguably the greatest result in the club's long history.
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