After six wins on the trot, Alex McLeish's ran out of luck in the Boris Paichadze national stadium which almost burst with Georgian pride as the home side registered only their third victory of the campaign.
Georgia's 17-year-old striker Levan Mchedlidze, making his first start for his country, headed the home side into the lead after 16 minutes.
David Siradze drilled home number two in the 65th minute to stifle any prospect of a comeback and although McLeish's side battled on, it is against the World Cup holders at Hampden next month that they will learn if they are to qualify for their first major finals since 1998.
The pre-match events should have offered a clue to Scotland's fate.
Manager McLeish contemplated his starting 11 without the injured Scott Brown, Alan Hutton and Gary Naysmith while Lee McCulloch and Garry O'Connor were suspended after picking up bookings in the 3-1 win over Ukraine at Hampden on Saturday.
Darren Fletcher, Graeme Murty, Shaun Maloney and Graham Alexander were drafted in and there was no surprise when the visitors looked disjointed early in the game.
Georgia coach Klaus Toppmoller, whose side had no chance of qualifying, handed starts to 16-year-old Levan Kenia and two 17-year-olds, goalkeeper Giorgi Makaridze and Mchedlidze, and it was the latter who was to strike the first blow.
Amid a scrappy opening, in-form James McFadden had turned a Kenny Miller cross just past the near post which looked to stabilise the Scots, playing in their new maroon away kit, but they looked out of sorts in the 16th minute when they found themselves a goal behind from a set-piece.
Giorgi Shashiashvili's corner came in from the left and it was Mchedlidze who rose between Alexander and David Weir to bullet a header past Scotland goalkeeper Craig Gordon from eight yards out.
The Scots floundered in the ensuing minutes, gasping for inspiration and it almost came on the half-hour mark when central defender Stephen McManus escaped his marker at a McFadden corner only to head over from close range.
A pitch invader halted proceedings for a moment before McFadden failed to impress referee Knut Kircher when he went down in the Georgia penalty area following a challenge by defender Lasha Salukvadze.
In the 38th minute, as the home fans turned up the volume, Mchedlidze forced Gordon to parry his shot from long distance and then McFadden's snap-shot at the other end cleared the crossbar by only a yard.
It was the Scots who finished the first half the stronger pushing for the equaliser with some re-established belief.
After Maloney was fouled 10 minutes after the restart, the Aston Villa attacker curled the subsequent free-kick from 20 yards wide of the left post.
Scotland, brighter and less intimidated, were pushing almost carelessly at times for the equaliser and when McManus fouled Kenia to prevent a breakaway, Gordon was called in to action to tip David Kvirkvelia's free-kick over the bar.
The visitors survived the corner but their punishment was suspended only to the 65th minute when they lost the second goal.
Kvirkvelia took on Murty down the right and his perfect cut-back was tucked away by Siradze.
McLeish, clearly going for broke, swapped Kenny Miller and Stephen Pearson for Kris Boyd and Craig Beattie immediately after the goal.
However, time was running out for the desperate visitors and when Georgia keeper Makaridze saved McFadden's 30-yard free-kick down at his left-hand post after 75 minutes, it was his first real action of the night.
Maloney was Scotland's main instigator in their attempt to grab a lifeline but the Georgians were nothing if not resilient.
In the 80th minute, as Scotland enjoyed the upper hand, McFadden tried his luck again with a free-kick from distance, this time driving high over the bar.
The home side soaked up the Scots' pressure in the closing stages with relative ease and it was McLeish's side, the beneficiaries of several disciplined performances, who were on the receiving end on this occasion.
Hampden awaits a titanic clash with the Italians next month.