For Philippe Clement, the task of reaching the Champions League was difficult enough with a full complement of Rangers players. 

Reduced to ten men by an unjust red card for new Brazilian signing Jefte, the mission verged on the impossible.

At the end of a tempestuous, bruising 90 minutes, the furious manager took to the Hampden pitch to remonstrate long and hard with Italian referee Marco Guida. It was an exercise in futility.

Booked after 31 minutes for clattering into Andriy Yarmolenko, Jefte was shown a second yellow card six minutes into the second half for a nothing challenge on Oleksandr Karavayev.

With both leaping for a high ball, there was no flying elbow, no question of endangering an opponent. Yellow cards fall outwith VAR’s tariff and, as the red card followed, Jefte reacted with disbelief. 

The Rangers support’s outrage was echoed by their manager after a defeat which cost him the chance of making some quality signings at the end of the window. At this level, refereeing mistakes come with a substantial price tag.

Fresh legs made the difference in the end. As a finely poised game edged into the final ten minutes goalless, extra-time loomed and the ten men clung on, fuelled by a sense of injustice.

That only gets you so far, the gasoline draining from the tank when Oleksandr Shovkovskyi’s late substitutes had a devastating impact.

Oleksandr Pikhalyonok cut in from the right and smacked a low 20 yard shot into the bottom left hand corner past a beaten Jack Butland. A second goal in two minutes arrived when the classy Mykola Shaparenko cut the ball back into the path of Nazar Voloshyn to smash the ball through Butland’s body.

A night of abject misery for Rangers had taken a dark turn when left-back Ridvan Yilmaz left the field on a stretcher and Ben Davies appeared as a makeshift left-back. 

On a night when Clement’s team failed to test Dynamo keeper Georgiy Buschan, the final outcome – like the anger and recrimination – was inevitable.

Hampden was a long way short of a full house, large swathes of empty seats around Scotland’s national stadium contributing to a strange old atmosphere until the anger created by the red card finally woke supporters from their slumber.

Make no mistake, this was an experience far removed from what Rangers are used to on European nights at Ibrox, when the raucous din drives the team to new heights in UEFA competitions. Not this team, not this time. The sight of Cyriel Dessers throwing his arms in the air to remonstrate with his own fans deep into the second half summed things up.

The League Cup holders were looking to reach the play-off round for the third season in a row after last year’s run ended in defeat to a powerful PSV Eindhoven side. By the end of an anguished 90 minutes, the visitors had earned the right to face RB Salzburg after the Austrian side overcame a late FC Twente rally to win 5-4 on aggregate. 

While group-stage football awaits in the Europa League, that won’t fill the black hole in the accounts. That won’t buy the players Rangers need to catch Celtic.

Ibrox hosted one of the memorable European nights back in September 1987 when Graeme Souness’ star-studded side beat a formidable Dynamo team in the first round of the European Cup.

Souness famously narrowed the width of the pitch to counter the Ukrainian champions’ wingers – and Clement must have wished he could repeat the trick when Dynamo’s star man Vladyslav Kabayev tortured captain James Tavernier.

His first incursion in the tenth minute left the full back for dead. A tantalising ball across the six yard line found no takers before Dynamo’s menacing wide man took on the Englishman again after half an hour. Once more, there was no one on hand to convert the cross. The warning signs were hard to ignore.

Clement pulled a surprise with his starting line-up. Vaclav Cerny, the stand-out player in last Saturday’s win over Motherwell, was left on the bench as Ross McCausland started. 

Cerny’s introduction at half-time was the inevitable recognition of the need for more quality in attack on a night when Rangers struggled to threaten the Dynamo goal.

They had their moments. A Tavernier cross picked out Jefte – playing on the other flank – only for his downward header to hit the side-netting. 

A comedy of errors saw McCausland’s low cross miskicked by Dynamo’s Volodymyr Brazhko into the path of Tom Lawrence. The midfielder allowed the ball to slither out of control and the chance was gone.

McCausland had a chance of his own. Dessers sent the young winger scurrying in behind the visiting defence with a pass from the halfway line. A tame side footed shot was parried wide by keeper Buschan and that would be McCausland’s last meaningful contribution before making way for Cerny at half-time.

No manager could legislate for what came next. The red card early in the second period for a forlorn Jefte blew a hole in the game plan. 

Seeing a flailing arm where none existed, the Italian official got this one wrong, VAR unable to reverse his folly. At some point someone really should look at that.

Rangers were shell-shocked and Dynamo would go on to take ruthless advantage. Karavayev – who had milked the impact of Jefte’s challenge – blew the best chance of the game when a piercing through ball sent the right-back through on goal. He never looked comfortable – or quick enough – to score, dragging a poor effort wide of the far post.

The ten men badly needed the support of their fans now, but noise and outrage and penalty claims were no substitute for genuine quality in front of goal. And Rangers have too little of that.

When Yilmaz left the field on a stretcher after apparently hurting his thigh, central defender Davies pitched in as a square peg in a round hole. It was natural to fear the worst.

So it proved as Rangers lost their energy and their shape in the final 10 minutes. The quality of the goals from Pikhalyonok and Voloshyn came as no consolation. If there was any respite or solace it stemmed from Vladyslav Vanat blowing a glorious chance to make it 3-0 after a poor clearance from Butland deep into stoppage time. Small mercies and all that.