Russia left Scotland's Euro 2020 qualifying hopes hanging by a thread as they came from behind to win 2-1 at Hampden Park.
John McGinn lifted spirits with an early goal, after a dreadful mistake by Russian goalkeeper Guilherme, but the visitors deservedly equalised shortly before half-time through captain Artem Dzyuba.
Russia's pressure was incessant, and they led when Stephen O'Donnell turned the ball into his own net trying to stop Yuri Zhirkov meeting a low cross.
Group I table
David Marshall kept Scotland in the game with a string of impressive saves, while Russia hit both the post and crossbar, and the hosts were unable to threaten in the closing stages as they fell six points adrift of the two qualifying spots in Group I.
Scotland hopes hanging by thread
This was a must-win match if Scotland were to retain any hopes of qualifying automatically from the group, ahead of welcoming the world's top-ranked side Belgium on Monday. A trip to face Russia again in Moscow looms next month, with the path to Euro 2020 now only looking likely through the Nations League play-off place.
There was a verve about Scotland's early play, and they were soon ahead thanks to a horrific goalkeeping error from Guilherme. He spilled Ryan Fraser's dangerous cross straight into the path of McGinn, who gleefully accepted the gift and slammed home his first international goal.
Hampden was suddenly alive with noise, but Russia posed a formidable threat, particularly through Dzubya. The 6'4'' striker out jumped Charlie Mulgrew but his header was tipped over by Marshall. The visitors began to dominate possession, with Aleksandr Golovin at the heart of much of their good work. He thumped a free-kick into the defensive wall, before Marshall tipped away Aleksei Ionov's tempting cross.
The growing Russian pressure eventually paid off with the equaliser on 39 minutes, although there was a touch of fortune in the build-up. Golovin's pass was deflected by Andy Robertson into the path of Dzyuba, and he picked up the loose ball in the box and coolly slotted it past Marshall.
Russia's momentum continued at the start of the second half. After Liam Cooper was booked for fouling Dzyuba, Mulgrew blocked Golovin's fierce strike. The Russia midfielder then carried the ball 50 yards towards goal as the Scotland defence parted, but his shot was just too high.
Scotland were being forced to soak up huge amounts of pressure, with Oli McBurnie now isolated and unable to offer an out-ball. The midfield was also stretched to breaking point, but the second Russian goal, when it came, was beautifully worked.
Ryan Fraser was intercepted by Ionov, who found Golovin with a terrific pass inside Cooper, and his cross was slid home at the back post by a combination of O'Donnell and Zhirkov, though the Kilmarnock man appeared to get the final touch.
Marshall kept Scotland in the game with a brilliant fingertip save from Mario Fernandes' header, deflecting it onto the bar, before Russia hit the frame of the goal again seconds later, when Magomed Ozdoev's shot flicked off both Scott McTominay and the far post.
Steve Clarke introduced Ryan Christie and Kenny McLean, and the Celtic midfielder found a rare sight of goal but shot straight at Guilherme. The changes appeared to galvanise Scotland, and Fraser's bullish run was ended on the edge of the box by Dmitri Barinov. It was a prime position for Mulgrew's dead-ball talents, but he curled the resulting free-kick narrowly wide.
More Scotland slackness then gave Zhirkov another sight of goal, but Marshall saved superbly again. The game was wide open - while Scotland had to chase, Russia were intent on finishing them off and they went looking for a third.
McGregor's goal-bound shot was blocked by Fernandes, before Russia scrambled the ball away as Scotland threw bodies into the box. On the break, Russia had a two man overlap, but Aleksandr Erokhin's weak effort was cleared off the line by Mulgrew.
There was to be no rescue mission in the closing stages, as Russia clinically closed the game out. Scotland were perhaps harshly jeered off, but a trip to a major tournament looks as distant as ever after this result.
Robertson lays into Scotland
Scotland captain Andrew Robertson fumed at his team-mates after their loss to Russia left their Euro 2020 qualifying hopes in tatters.
Robertson took aim at his side's reaction to their bright start at Hampden Park, saying he had "never seen anything like" the manner in which he felt his country froze after netting the opener.Click here to read reaction from Robertson, McGinn and manager Steve Clarke.
- Scotland saw their run of nine competitive home internationals without a loss ended by Russia, their first such defeat since September 2015 against Germany.
- No player has been directly involved in more goals in Euro 2020 qualifying than Russian Artem Dzyuba (6 goals, 2 assists).
- Scotland have lost a home match after taking the lead for the first time since March 2013, when going 1-0 up against Wales, to lose 1-2.
Scotland host World Cup third-placed side Belgium on Monday on Sky Sports Football from 7pm; kick-off is at 7.45pm. On the same evening Russia host Kazakhstan on the Red Button from 7.40pm; kick-off at 7.45pm.