Rangers suffered a late collapse as Dynamo Kyiv scored twice within two minutes to ruin the Light Blues' hopes of reaching the Champions League play-offs.
Philippe Clement's side had to play the majority of the second half with a man less following Jefte's dismissal after the summer signing was shown a second yellow card by the match referee.
Despite boasting an extra player, the Ukrainian opponents were reduced to very few clear-cut opportunities until the final 10 minutes where Oleksandr Pikhalyonok and Nazar Voloshyn fired beyond Jack Butland to send the majority of the Rangers support towards the exit door.
Clement's men will now settle for Europa League football once again this season. Whereas Dynamo Kyiv will face RB Salzburg for a chance to dine at Europe’s top table until beyond Christmas.
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Here's how the Rangers players rated at Hampden Park.
JACK BUTLAND - 5
The former England international was kept quiet for the most part until Dynamo Kyiv's quick fire double.
The first strike was finely placed into the bottom corner, and the second he perhaps will be asking why his defence weren't closing Voloshyn down with more intent.
That goals seemed to spook him as he almost gave away a cheap third in second half stoppage time following a slack clearance. The Rangers shot-stopper will have better nights.
JAMES TAVERNIER - 6
Provided some brilliant crosses in attacking areas, but was given a torrid time by Vladyslav Kabayev throughout the opening 45 minutes.
JOHN SOUTTAR - 6
Almost exposed early on with a ball into the box, however the Light Blues centre-back recovered well and displayed his no-nonsense defending by denying a guilt-edge chance for the visitors.
ROBIN PROPPER - 6
Was at the heart of a Dynamo Kyiv penalty shout for handball, but fortunately the decision went his way. There's early signs that the Dutchman is comfortable playing the way Clement asks from his defender's and it will take time to cement a strong understanding with his defensive cohorts.
RIDVAN YILMAZ - 6
A strong showing from Rangers' new undisputed left-back. Worked tirelessly and it was a shame to see him stretchered off with 15 minutes to play.
It looked as though he teared his thigh whilst attempting a shot on goal.
MOHAMED DIOMANDE - 6
Picked up a cheap booking shortly before the interval. Did display quick feet and sharp mobility when he found pockets of space in midfield. Can never question his effort but surely Rangers need to be adding more creativity before the transfer window closes.
CONNOR BARRON - 6
A fourth consecutive Rangers start for the ex-Aberdeen youngster. You can see he's rising to the added responsibility at his new club. Although, it could be said he was a little too eager and culpable for the second goal his team conceded.
TOM LAWRENCE - 5
Dithered when the ball came to him inside the Dynamo box on the half-hour mark. Premium chances tend to be at a premium at this level so it was an opportunity the Welshman will know he should've done better.
Was guilty of not looking up to see whether a better option was on a few times too.
ROSS MCCAUSLAND - 6
Wasn't afraid to take his opposition full-back on and the majority of play tended to come down the right-hand side during the first half. Sacrificed at the break as Clement opted for a tactical tweak.
JEFTE - 5
Unlucky with a back post header from Tavernier's delivery midway through the first half. Always seemed eager to be involved at both ends. His evening ultimately ended on 49 minutes after being shown a second yellow card. Clement and his player will reckon it was a very harsh decision - but one that VAR was unable to overrule.
CYRIEL DESSERS - 6
You could argue that it was a thankless shift up front for the Rangers lone striker. Tried to hold the ball up yet was often crowded out quickly without any support. Always a willing runner and linked up well when he could find a teammate. The hero of the first leg didn't have any clear cut chances himself.
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SUBSTITUTES
VACLAV CERNY - 6
Introduced for McCausland at the half-time break. Didn't see a lot of the ball, although when he did, you were always confident something positive was going to happen. The Czech winger looks a real find and sadly for Rangers they just couldn't utilise him enough.
DUJON STERLING - 4
The versatile player replaced Diomande on 68 minutes and tried to add energy into Rangers' play. It was evident they were a man short though as the midfield was getting over-run by time Sterling was among the action.
BEN DAVIES - 4
A first outing since a hour to forget at Tynecastle on August 3. Rangers losing two goals once he was on the field won't have aided his chances of starting more games.
RABBI MATONDO - 4
On too late to make an impact.
