Gareth Bale's 88th-minute strike clinched a dramatic 2-1 win for Wales and inflict a significant blow to Scotland's hopes of reaching the 2014 World Cup.
Scotland looked to have clinched their first win in Group A after James Morrison's first-half goal handed them the lead in a pulsating qualifier.
But having terrorised the Scottish defence all evening, Tottenham star Bale struck twice in the final 10 minutes to clinch a first victory for Wales manager Chris Coleman and heap more pressure on Scotland boss Craig Levein.
Bale clawed back an equaliser when he was felled in full flight by Charlie Adam and duly dispatched the resulting penalty 10 minutes from time.
A share of the spoils would have served neither side in this closely-contested tie and with just two minutes remaining, it was Bale, the best player on the pitch by some distance, who proved the difference.
Again Adam was penalised for a foul on the Spurs flyer who picked himself off the turf to receive Aaron Ramsey's free-kick on the edge of the box and fire home a sumptuous left-footed shot past Allan McGregor.
It was a remarkable climax to this clash that had become a fight for survival between the respective managers.
Victory enabled Wales to leapfrog Scotland into fourth place and lift a huge burden off the shoulders of Coleman in the wake of four straight losses after succeeding Gary Speed.
However the result left Levein facing major questions, particularly as he was able to name Manchester United midfielder Darren Fletcher as captain, following a year-long absence with a chronic bowel problem, as well as Sunderland striker Stephen Fletcher who ended his self-imposed exile.
Wales were without Craig Bellamy but started with Bale and Ramsey, stripped of the captaincy, who carved out the opening chances of the tie.
Bale served early warning when he stepped inside Danny Fox but curled his effort just wide of the far post
Ramsey then burst through the middle, laid off to Joe Allen whose effort was blocked by the lunging Gary Caldwell.
A lively contest swung in the space of 30 seconds of the 27th minute.
Bale breezed down the right-flank past Fox and delivered an inch-perfect cross to the on-rushing Steve Morison who could only direct his header across goal.
The Norwich City striker should have done better and Wales were immediately made to pay.
Fletcher out-jumped Wales captain Ashley Williams to guide the resulting goal-kick into the path of Morrison and the West Bromwich Albion midfielder buried his effort into the bottom right corner.
It was only Morrison's second international goal having previously netted against Wales last year in the Celtic Nations Cup.
Fletcher failed to connect with a cross by Fox but by now Bale was in full flight only for Ramsey to fire over the bar.
New Wales goalkeeper Lewis Pryce denied Morrison a second from point-blank range and Fletcher had his effort ruled out after the ball went out of play before Bale produced his late heroics.