Rangers have been knocked out of the Champions League after suffering defeat to Dynamo Kyiv at the qualifying stage.
Two late goals in two minutes at Hampden handed the visitors a 2-0 win that means Philippe Clement’s side will drop in to the Europa League for the second consecutive season.
The sides came into the game with the score-level following a 1-1 draw in Poland last week, but after a goalless first 45 minutes, Rangers were left with a mountain to climb following a sending off early in the second-half.
Jefte was shown a second yellow-card just after the break after leaping on top of a Kyiv defender and they struggled to compete after that.
Oleksandr Pikhalyonok scored the opening goal to give the Ukrainian side a lead with ten minutes remaining before Nazar Voloshyn put the game to bed just a minute later.
It was a cagey first-half at the national stadium on Tuesday night with chances coming few and far between in the opening stages.
Last week’s hero Cyriel Dessers was first to test the goalkeeper when he came close with a header that was well-saved on the 25th minute.
Other than that there wasn’t much action at either end with both clubs looking as though the pressure of the tie was weighing heavily on their shoulders and were scared to make a mistake.
Clement made a change at half-time as he replaced Ross McCausland with Vaclav Cerny, who opened his Rangers account at the weekend, in the hope of getting the all important goal.
But the second-half was less than ten minutes old when they were reduced to ten-men with Jefte being sent-off for a harsh second booking.
Dynamo Kyiv had a period of dominance after the red-card and they should have taken the lead when they burst through the Rangers defence to have a clear route to goal but Vanat’s strike was wide of Butland’s post.
They came close again just minutes later but this time John Souttar was on hand to make an important block that kept the score at 0-0.
It now was looking like a case of hanging on for Rangers as they tried to regroup and regain some composure as a Kyiv header flew just over the bar.
The home side then started to grow back into the game a bit more with Cerny, Dessers and Diomande involved in a string of attacks before Ridvan’s speculative effort was easily saved by Georgiy Bushchan.
But with ten minutes of the game remaining Kyiv took the lead through Pikhalyonok who struck from outside the box into the bottom corner to make it 1-0.
And the tie was put to bed just a minute later when the away side scored again to double their lead.
They created space again with an attack up the left-hand side before Voloshyn smashed the ball past Butland to make it 2-0 on the night and 3-1 on aggregate.
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