Scotland must rely on coming through the Euro 2020 play-offs to book their place at next summer's finals after they were thrashed 4-0 in Russia.
Steve Clarke's men suffered an alarming second-half collapse in Moscow as Artem Dzyuba scored twice (57 & 70) to help book the hosts' place at the finals.
Magomed Ozdoev's thunderous drive came just three minutes after Dzyuba's opener (60) to knock the stuffing out of the visitors while Aleksandr Golovin (84) completed the scoring with a well-taken finish.
The result moves second-placed Russia onto 18 points in Group I, still three points behind leaders Belgium, while Scotland can no longer qualify automatically and remain in fifth place.
Russia: Guilherme (6), Fernandes (7), Semenov (6), Kudryashov (7), Dzhikiya (6), Ozdoev (7), Barinov (7), Zhirkov (7), Golovin (8), Ionov (7), Dzyuba (9).
Subs: Cheryshev (6), Akhmetov (6), Komlichenko (n/a).
Scotland: Marshall (6), Palmer (5), Robertson (6), Mulgrew (5), Devlin (5), Fleck (6), Snodgrass (5), McGinn (6), McGregor (5), Fraser (5), Burke (4).
Subs: Armstrong (n/a), Shankland (6), Christie (6).
Man of the match: Artem Dzyuba.
How Scotland were left seeking a Euro 2020 lifeline
Scotland had sought to build some momentum through a confident performance heading into what would currently be a Euro 2020 play-off against Norway in March, but on this evidence, they are well off the pace.
Russia were written off inside and outside their own country before storming to the quarter-finals as hosts of the 2018 World Cup hosts, and they enjoyed 72 per cent possession during a dominant opening 45 minutes in wet conditions at the Luzhniki Arena.
Scotland heading for Euro 2020 play-offs
Scotland's latest loss officially ended their remote hopes of a top-two finish and left them in fifth place in Group I, four points behind third-placed Cyprus.
But Clarke's men are guaranteed to be in the Euro 2020 play-offs after beating Israel to win their Nations League group.
As winners of Group C1, Scotland will currently face a play-off semi-final against Norway, the winners of Group C3.
Serbia and Finland are currently set to compete in the other semi-final from League C with the games to take place in March 2020.
However, Norway, Serbia and Finland are all still in contention to qualify automatically, so Scotland may come up against different opposition.
But after 3-0 defeats in Belgium and Kazakhstan, Clarke's side produced a disciplined and compact first-half display to reduce their opponents to half-chances. Aleksei Ionov's close-range shot was blocked by Andrew Robertson while Golovin drew a routine save from David Marshall.
Clarke was forced into a change at half-time as Lawrence Shankland replaced the injured Oliver Burke, but the hosts took the lead during Scotland's best period in the match.
Charlie Mulgrew needed to exert better body strength as he was shrugged off the ball by Dzyuba, who met Golovin's corner to crash a first-time shot beyond Marshall. It was the Russia talisman's 22nd goal in 39 internationals, becoming his country's third highest scorer overtaking Roman Pavlyuchenko.
Michael Devlin and John Fleck made their Scotland debuts. Aberdeen centre-back Devlin featured in a back four that also had the surprise inclusion of Sheffield Wednesday right-back Liam Palmer in favour of Stephen O'Donnell.
Fleck was joined by Callum McGregor and John McGinn in midfield with Robert Snodgrass and Ryan Fraser out wide. Oliver Burke started up front.
"The same old problems crept in with them conceding off a set-piece," former Scotland midfielder Darren Fletcher told Sky Sports. "Dzyuba showed great strength, but from there it all just fell apart."
While the opener was avoidable, there was little Scotland could do about Ozdoev's superb second as he drilled in Golovin's lay-off from the edge of the box.
With the game over as a contest, Scotland failed to draw any consolation for the 1,000-strong Tartan Army as sloppy defending from Mulgrew and Michael Devlin allowed Dzyuba to take Mario Fernades' header back across goal on his chest before prodding home his second from close range.
Russia only had five shots on target, but they once more showed their clinical touch with six minutes remaining as Golovin capped a fine individual performance by taking Dzyuba's disguised pass to compound Scotland's misery.
What the managers said
Scotland boss Steve Clarke: "We conceded a soft goal, the first goal was soft from the corner. Man-on-man we have to do better. From there we quickly found ourselves out of the game, allowed the game to run away from us.
"We have to put it down to fragile confidence, players seem to lose heart very easily, which is unfortunate because we had done okay up to that point."
Man of the match: Artem Dzyuba
Russia were making their first appearance in Moscow since knocking Spain out of the World Cup and it was a familiar source who ensured they sent the vast majority of the 70,000 fans in attendance home happy.
Only Israel's Eran Zahavi (10) has scored more goals in EURO 2020 qualifying so far than Russia's Artem Dzyuba (8) - and this was the complete performance from the Zenit St Petersburg striker.
After a first half spent sparring with Charlie Mulgrew, the 31-year-old came into his own, out-muscling the Blackburn defender for his opener before bullying both him and Devlin for his second.
For good measure, he gave up the chance of his hat-trick by unselfishly setting up Golovin for Russia's fourth.
Devlin: Special moment ended in disappointment
Debutant defender Michael Devlin told Sky Sports...
"Up until the first goal I thought it was a decent performance. For the last half hour it wasn't good enough and we conceded poor goals and we need to look at ourselves.
"It did seem like that (a collapse), I am not quite sure why that happened.
"We have good experience on the pitch, okay we have some with not too many caps including myself but I think we are experienced enough to know how to dig in and see a tough period through.
"But we didn't do that and we need to look at ourselves and take responsibility for what is a really disappointing result in an evening when we expected so much."
Analysis: Size of task now clear to Clarke
Sky Sports News reporter Luke Shanley in Moscow...
When the Scotland head coach comes out with phrases in his post match interview like 'collapsed' and 'mentally fragile' then you know you are struggling.
That is what Steve Clarke told me in the tunnel in his interview after Scotland's second consecutive 4-0 defeat. For 57 minutes, they seemed to be coping with their Russian hosts but once captain and talisman Dzyuba opened the scoring, there was no way back for Scotland.
Conceding goals is becoming a worrying habit, that's now 13 in the last 4 games (two against Belgium and two against Russia).
Clarke tried to mix things up tonight making six changes from last time with Devlin and John Fleck making their debuts.
Scotland can't celebrate a good hour in Moscow especially what happened after that and Clarke is not looking for any positives as he goes back to the drawing board.
Another telling comment after the game was he feels this job is tougher than he thought it would be and he knew it was going to be tough when he was appointed.
The team ranked the worst in the world now visit Hampden Park on Sunday evening. A win over San Marino is expected but the turnout from the Tartan Army will tell it's own story.
- Russia remain unbeaten against Scotland (P4 W2 D2 L0), with all four matches coming in Euro qualifiers, winning each of the last two.
- Scotland have lost four consecutive matches in all competitions for the first time since 2004, under Berti Vogts.
- Russia have won 10 of their last 11 qualifying matches, losing only against Belgium back in March.
Live Euro 2020 Qualifiers
Scotland host San Marino at Hampden Park on Sunday, live on Sky Sports Football. Coverage starts at 4.30pm with kick-off at 5pm. Russia visit Cyprus at the same time.