Scotland captain Andy Robertson labelled his side "scared" after blowing an early lead to lose 2-1 to Russia and realistically end their hopes of automatic qualification for Euro 2020.
John McGinn's early opener was just reward for Scotland's bright start, but Artem Dzyuba's equaliser five minutes before half-time sapped the hosts' energy and belief.
Russia controlled the second period and could have won by more than a solitary goal when Stephen O'Donnell turned Aleksandr Golovin's dangerous cross into his own net on the hour mark.
"We've only got ourselves to blame," said Liverpool left-back Robertson. "We started well, got the goal and then it was as if the goal scared us.
"I've never seen anything like that before. That needs to change because if we go into a lead it should be a positive not a negative."
After opening their campaign with a disastrous 3-0 defeat in Kazakhstan that ultimately cost Alex McLeish his job, Scotland are playing catch up and needed a win to maintain realistic ambitions of finishing in the top two positions of Group I.
Belgium, who visit Hampden on Monday, lead the group on 15 points with Russia just three behind in second place, six ahead of the Scots who sit fourth behind Kazakhstan.
Scotland will now likely have to come through a playoff next March, earned by winning their group in the Nations League, to reach a first major tournament in 24 years.
Steve Clarke was taking charge of just his third match as Scotland boss and he was also at a loss as to why his side failed to build on such a positive start.
"We got on top and got ourselves in front then for some reason I'm yet to determine we stepped off the gear," said Clarke. "We let Russia dominate us and let them impose their style of play on us."
Russia were forced back with the talented trio of Robertson, Ryan Fraser and Callum McGregor a constant danger down the left.
Just 11 minutes in, the hosts led as Fraser's low cross was horribly spilled by Russian goalkeeper Guilherme and McGinn gratefully slotted into an unguarded net.
- Russia take control -
However, the World Cup quarter-finalists quickly wrestled back control and it was no surprise when Russia equalised as the towering Dzyuba showed a fleetness of foot to drill low past David Marshall after the ball rebounded into his path off Robertson.
"We started too relaxed. It took some time to get into the game and we have to do from the first second," said Russia coach Stanislav Cherchesov.
"I am very happy that we won. We showed our character today."
Russia's superior class shone through at the start of the second half with Golovin pulling the strings.
The Monaco midfielder was too quick and clever for Liam Cooper with a square ball from which O'Donnell put into his own net under pressure from Yuri Zhirkov.
Marshall then made a brilliant save to turn Mario Fernandes's header onto the bar and Magomed Ozdoev struck the outside of the post as the visitors threatened to run riot.
The Wigan goalkeeper made another stunning stop to deny Zhirkov a spectacular goal late on, but it was to no avail on another sobering night for Scotland.
"I don't think anyone got pass marks apart from David Marshall," added a frustrated Robertson.
"To have 10 players from the start not really showing up and giving the performances that we can do is never going to win you a game of football."