When you need to beat the best team in the world to give yourself a shot at qualification for the Euro finals out of your group you know you are in deep trouble.
A 2-1 defeat to Russia has left Scotland six points adrift of the nation they need to climb above to have no need of their play-off safety net.
The plan for the September double-header was to win this match and then hope for a footballing miracle against Belgium on Monday night.
Now that footballing miracle has to happen. And even that might not be enough.
Early optimism after a John McGinn goal, his first for his country, was wiped out by Artem Dzyuba’s equaliser and the subsequent domination of an impressive Russian side.
The winner – a Stephen O’Donnell own-goal – was thoroughly deserved and the wait for a meaningful Scotland win goes on.
It was a fast start Steve Clarke would have been looking for and it was a fast start he got.
Within 30 seconds his team had worked its way to the edge of the Russian box and McGinn was letting fly with an 18-yard strike that skimmed the grass on its way past the near post.
Mind you, it didn’t take long for the visitors to get a shot away either.
A couple of minutes later Yuri Zhirkov was quickest to react to a loose ball in the box. His left foot volley wasn’t the purest but it had David Marshall beaten and didn’t drop over the crossbar by much.
Once the contest settled down it was Scotland who exerted control first – and crucially got a goal during their spell on top.
Just over a minute before the deadlock was broken, O’Donnell had hit the post from the third Scottish corner in 10 minutes.
That set-piece came from the left and it was a cross from that side, by Ryan Fraser, which produced the goal.
Keeper Guilherme dropped the in-swinger, probably because he had one eye on Oli McBurnie who had made a run across him. McGinn controlled the ball beautifully with his first touch and lashed it home from eight yards with his second.
There was nothing cagey about this match and Russia came very close to equalising on 17 minutes.
Dzyuba rose above Charlie Mulgrew near the penalty spot to meet a cross from the right and it took a finger-tip save from Marshall to help the header over the bar.
James Forrest has been in brilliant early-season form for Celtic but he squandered an opportunity to tee up McBurnie for goal number two midway through the half.
He powered into the box unchallenged but his cut-back was a disappointing one.
Just before the half-hour mark Forrest nearly cost his team a goal at the other end by neglecting his defensive duties.
He was caught flat-footed as a ball was played inside him and by the time he had reacted Aleksei Ionov was uncatchable. Thankfully, Ionov’s cross didn’t match the quality of his run.
Clarke had clearly put the week’s training to good use, with set-pieces much improved from the McLeish era.
Scotland carried a threat from most of them and Liam Cooper letting a Fraser dead-ball cross through his legs looked like a rehearsed routine. It definitely caught the Russian defensive line out and Mulgrew had a free header that he directed straight at Guilherme.
With Scotland dropping deeper and deeper this didn’t have the feel of a match they could see out as a 1-0 and so it proved.
Russia’s close-space passing had been impressive and when Andy Robertson attempted to break up one such move that had arrived in the box he only succeeded in dishing up a treat for Dzyuba who was clinical with his low finish.
The level scoreline was a fair one at the break but it was almost 2-1 to Russia seconds after the re-start.
Aleksandr Golovin was given space to shoot and his effort was blocked by Mulgrew.
It came as no shock that the Monaco playmaker was Russia’s main man at Hampden and letting him run at you unchecked was never likely to be a wise defensive ploy.
After Golovin picked up the ball in midfield, Mulgrew backed off and backed off until the inevitable shot was struck. The only surprise was that it didn’t find the back of the net.
An even battle for much of the first half was now becoming anything but.
The Scots were inviting trouble with their retreats and slack passing and it took a last-ditch Cooper block to prevent Mario Fernandes scoring at the back post.
The goal that the Tartan Army were fearing (and expecting) came on 59 minutes.
Cooper was ponderous to allow Golovin to go by him and when the ball was squared across the six-yard box O’Donnell lost out to Yuri Zhirkov. Zhirkov was claiming it but it looked more like an own-goal.
Clarke made a double substitution in an attempt to turn the tide, with Kenny McLean and Ryan Christie coming on for Forrest and McGinn just after the hour.
It was still wave after wave of attack crashing upon Marshall however.
Twice the keeper’s woodwork was hit within a minute – first when he superbly got his fingers to a downward header and then when he was well beaten by a deflected shot.
It came as a welcome shock when there was a Scotland shot at last. Not that Guilherme had much to do with Christie’s effort that was straight at him.
Still, at least it was something.
There was further encouragement after Fraser got himself involved in the game again at last, his strong run off the wing being ended by a foul 22 yards out.
Mulgrew took the free-kick, got it up and over the wall and narrowly missed the target.
Normal service was resumed when Marshall was at full stretch to save from Zhirkov.
Clarke’s last roll of the dice was bringing on Matt Phillips for Scott McTominay and going two up top.
With five minutes to go McBurnie did really well to beat his man and get a cross to the back post. The clearing header from Fernandes was a poor one but the ball just wouldn’t sit down quickly enough for Callum McGregor, with his shot eventually being blocked.
A drop of the ball from Guilherme nearly presented McGregor with an equaliser. Scotland were understandably gambling by this stage and a swift four on two counter-attack resulted in a Mulgrew goal-line clearance.
There was to be no late drama and all hope in Group I seems lost.