Jefte was harshly sent off for Rangers before two quick goals for Dynamo Kyiv ended their hopes of another Champions League season.
Cyriel Desser’s last-gasp equaliser in the first leg gave Rangers renewed hope and both he and Ross McCausland had chances to put them ahead early in the third qualifying round return leg at Hampden Park.
Jefte, who already had a yellow card, was shown a yellow card in the 50th minute when he jumped up to head the ball and was also shown a red card, which made the hosts’ game a real problem.
They held out for 30 minutes, but eventually Philippe Clement’s side collapsed and substitutes Oleksandr Pikhalyonok and Nazar Voloshyn scored in quick succession to secure the evening’s 2-0 victory (3-1 on aggregate) and send Dynamo into the play-offs to face RB Salzburg.
Heartbreak in Hampden
It was not a good night for Clement’s team, who see this as a missed opportunity as they are relegated to the less prestigious and certainly less lucrative group stage of the Europa League.
The Rangers started with high pressure and the guests initially seemed unsure in defense.
However, Oleksandr Shovkovskyi’s side came into the game better and in the ninth minute winger Vladyslav Kabaev shot past Rangers captain James Tavernier on the left, but his inviting cross went unanswered, much to Rangers’ relief.
Rangers made little progress until the 20th minute, when Jefte headed Tavernier’s curved cross past the far post before firing a shot over the bar from 23 metres a few minutes later.
A header from Dessers from a cross by Jefte was easily saved by Kyiv goalkeeper Georgiy Bushchan. As Rangers then applied pressure, the ball fell to Tom Lawrence in the box, but he could not find his feet to take a shot.
Kiev appeared quick and determined in their attacks, which kept the Rangers defense on high alert.
On a counterattack by Rangers just after the half hour, Dessers played to McCausland, but although his shot was saved by Bushchan, Clement’s team could not capitalise on the loose ball.
Cerny came on for McCausland early in the second half, giving Rangers fans cause for optimism, but this was dashed when Jefte, who was booked for a touchline foul on Andriy Yarmolenko after 30 minutes, was booked again and sent off after an aerial challenge with Oleksandr Karavaiev.
As the dust settled after a seemingly harmless second yellow card and the Rangers fans turned up the noise in defiance, Karavaiev ran past the defense but his shot went wide.
Kyiv took advantage of the extra player and threatened before the Rangers caught up and the game swung back and forth.
In the 68th minute, tiring midfielder Mohamed Diomande was replaced by Dujon Sterling and Ben Davies took over the role of Ridvan Yilmaz, who was carried off the field on a stretcher after sustaining an injury from a shot a few minutes earlier.
It was another setback for the Light Blues, and Dessers appeared to take umbrage with the fans after hearing moans and groans when he lost the ball due to a lack of support.
Rangers keeper Jack Butland was hardly under fire, but was able to parry a long-range shot from Taras Mykhavko.
In the 82nd minute, however, he had little chance when Pikhalyonok shot from distance without any pressure from the Rangers defense.
Voloshyn then converted a back pass from Mykola Shaparenko to win the game, with Butland ultimately saving himself when he parried a shot from Vladyslav Vanat following his initial error.
Clement: The worst decision I have ever seen
Rangers coach Philippe Clement on the decision about the red card:
“I have seen pictures and it is clear that there is sometimes a grey area in football and that is why VAR exists to help make football more honest.”
“But the decision had nothing to do with the grey area. It was really clear that nothing was going on.
“Jefte jumps higher, he doesn’t move his hand, his arm is next to his body, it’s nothing.
“I try to understand the decision and ask questions, but the referee stuck to his opinion that it was a clear foul and a second yellow and a red card. I am convinced that his bosses will have a different idea.”
“This is a crucial moment and in the end it has destroyed the dream of the dressing room and the dream of more than 50,000 fans. You now expect better decision-making.”
“This is the worst decision I have seen in over 30 years of football.
“I have a lot of things on my mind, but you know if I say too much I can get banned, so let’s keep things in mind.
“I have to be good and smart for the club and the team and we have to move on and learn positive lessons from the two games.”
Boyd: A hammer blow
Sky Sports Kris Boyd on Jefte’s sending off:
“How that can be given as a second yellow card is beyond me. He jumps up with his arms hanging, the Dynamo Kyiv player falls to the ground and the referee takes it away from him and gives him a yellow card.”
“I know with VAR you can’t go and review a second yellow card, but it was horrific.
“You have to recover from that, but you feel like the Rangers could have played all night without scoring a goal.
“This is a big blow for Rangers. I’m not saying they would have beaten Salzburg in the next round, but the £5m would have been huge. Could that have been invested in strengthening the squad?
“That’s a lot of money that Rangers are not getting, especially considering how well they played in Poland last week.”
“Plus 39,000 at Hampden. Rangers fans are not happy and rightly so. This whole situation with the stadium has once again cost Rangers dearly.
“Champions League nights at Ibrox, teams breaking down. There was not much going on at Hampden tonight.”
What’s next for the Rangers?