Rangers' Champions League aspirations ended for another season with a 2-0 defeat by Dynamo Kyiv at Hampden Park where they ended up with 10 men.
Following a 1-1 draw in the first leg of their third qualifier in Poland last week, the match struggled to spark into life until the 51st minute when new signing Jefte, making his first start for the Light Blues, was sent off by referee Marco Guida after picking up a second yellow card for an aerial challenge on Oleksandr Karavaiev.
It looked a harsh decision and it stoked a fire under the Rangers support but two late goals in two minutes from second-half substitutes Oleksandr Pikhalyonok and Nazar Voloshyn took the Ukrainian side to a 3-1 aggregate win.
It was not a great night for Philippe Clement's side who will see this as an opportunity lost and will drop into the less prestigious and certainly less lucrative Europa League phase.
It was the Light Blues' second game at their temporary home which is being used due to the delayed refurbishment of one stand at Ibrox.
They won 2-1 against Motherwell at the national stadium on Saturday - and there were thousands of empty seats at kick-off.
Czech winger Vaclav Cerny, who scored a terrific winner against Well in his first start since signing on loan from Bundesliga club Wolfsburg, started on the bench along with fellow winger Scott Wright.
Jefte was installed along with Northern Ireland winger Ross McCausland while former West Ham forward Andriy Yarmolenko was in opposition again.
Rangers made a high-pressing start and the visitors initially looked uneasy in defence.
However, Oleksandr Shovkovskyi's side worked their way into the game and in the ninth minute winger Vladyslav Kabaev sped past Rangers captain James Tavernier down the left but his inviting cross found no takers, to Rangers' relief.
Rangers made little headway until the 20th minute when Jefte headed a looping Tavernier cross past the far post, before thundering a snatched shot from 25 yards high over the bar minutes later.
A Cyriel Dessers header from a Jefte cross was easily saved by Kyiv keeper Georgiy Bushchan and then, as Rangers pressed, the ball fell to Tom Lawrence inside the box and he could not sort out his feet to get a shot away.
When they did attack, Kyiv looked pacey and purposeful which kept Rangers' defence on a state of high alert.
In a Rangers counter just after the half-hour mark, Dessers played in McCausland but although his shot was parried by Bushchan, Clement's side failed to take advantage of the loose ball.
Cerny replaced McCausland for the start of the second half which gave Rangers fans reason for optimism but that disappeared when Jefte, booked for a touchline foul on Yarmolenko after 30 minutes, was cautioned again and sent packing for an aerial challenge on Karavaiev.
When the dust had settled on what looked like a soft second yellow, and the Rangers fans cranked up the noise in defiance, Karavaiev raced clear of the defence but screwed his shot wide.
Kyiv took advantage of the extra man and moved with menace before Rangers rallied, and the game swung end to end.
In the 68th minute Dujon Sterling replaced tiring midfielder Mohamed Diomande and Ben Davies took over from Ridvan Yilmaz, who was taken from the field on a stretcher after picking up an injury after taking a shot minutes beforehand.
It was another blow for the Light Blues and Dessers seemed to take umbrage with the fans after hearing groans and moans when he lost possession when he had no support.
Rangers keeper Jack Butland was hardly under fire but he did save a long distance effort from Taras Mykhavko.
However, in the 82nd minute, he had little chance when Pikhalyonok fired in from distance under no pressure from the Rangers defence.
Voloshyn then converted a cut-back from Mykola Shaparenko to seal the tie, with Butland rescuing himself at the end when he saved a shot from Vladyslav Vanat, after his initial mistake.
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