Valeri Kazaishvili scored a decisive first-half goal to dent Scotland's hopes of qualifying for Euro 2016 as Georgia ran out 1-0 winners in Tbilisi.
A scrappy game was settled eight minutes before half-time, when Kazaishvili drilled a low shot past Scotland goalkeeper David Marshall to give his nation a rare international victory.
Defeat had a sense of deja vu about it for Scotland, whose bid to reach Euro 2008 was effectively ended by a 2-0 reverse at the Boris Paichadzis Erovnuli Stadium, and Gordon Strachan's men face an uphill struggle to finish in the top three of Group D.
The result hands the Republic of Ireland the chance to leapfrog Scotland into third should they win at Gibraltar later on Friday.
Strachan's side were largely restricted to half chances on a hot night in Tbilisi, failing to score for the first time in 13 international matches, meaning the prospect of facing Germany at Hampden Park on Monday will now feel all the more daunting.
Georgia had lost their previous three home qualifiers and were without a win under coach Kakhaber Tskhadadze, who took over from Temuri Ketsbaia in December, but a vociferous crowd roared them to only their second three points of a dismal campaign.
Despite the heat in Tbilisi, which had reached 32 degrees Celsius just a few hours earlier, both sides raced into attack in the opening minutes, with Andy Robertson and Alan Hutton finding plenty of space down either flank for Scotland.
Scotland were content to let Georgia enjoy long spells of possession that posed little threat, and their patience almost paid off when Steven Fletcher was inches away from converting a dangerous low cross from Robertson, but he slid in just too late to connect and the ball ran out of play.
Marshall had barely touched the ball when a header from inside the penalty area by Levan Mchedlidze found Kazaishvili on the edge of the box, and the Vitesse midfielder took a perfect touch to tee himself up for a well-struck low drive into the bottom corner.
Jano Ananidze tested Marshall again just after the break, clipping a shot towards goal from close range after a well-worked corner, but the Cardiff goalkeeper was alert to the danger.
Steven Naismith had a golden chance to equalise when Shaun Maloney's corner reached him on the goal line, but he fouled Nukri Revishvili in his attempt to score and conceded a free-kick.
Scotland attacked with real intent as they probed for an opening, but Davit Kvirkvelia denied Ikechi Anya with a smart challenge as the Watford winger jinked into the box.
Maloney, who was part of the Scotland team that lost in Tbilisi in 2007, started to show his quality and his precise throughball carved an opening for Fletcher, but the striker was caught offside as his shot struck a post.
Mchedlidze almost made it 2-0 with a run and cracking shot from 20 yards, but Marshall spared Scotland further misery with a superb one-handed save.
Scotland pressed in the final minutes and were within a yard of a crucial equaliser when James Morrison met Charlie Mulgrew's corner with a header that flashed wide, but some desperate Georgia defending prevented further chances in a nail-biting climax and Strachan's side failed to register a shot on target.
