Christian Panucci's header in injury time brought a tearful end to Scotland's Euro 2008 qualifying campaign as Italy progressed following their 2-1 win at Hampden Park.
It was a backs-to-the-wall performance from Roberto Donadoni's side for much of the second half after Barry Ferguson had cancelled out Luca Toni's second-minute opener.
But with victory the requirement for qualification for Alex McLeish's battling side, it was Panucci who finally put them to the sword in the 90th minute, a goal that confirmed Scotland's exit from the competition.
After such a patriotic build-up and with Hampden Park bubbling with expectancy, a sense of realism was restored within seconds of the kick-off as Toni's smart finish from the game's first attack silenced the home crowd.
With the Scotland defence caught napping Antonio Di Natale was able to take advantage of a quick throw-in and square for Toni, who met the ball with the outside of his boot to fire high into Craig Gordon's net.
With Scotland rocked back on their heels they could have found themselves two behind minutes later as Stephen McManus and David Weir continued to give Toni too much time and space, Mauro Camoranesi firing over.
It took until 20 minutes into the game before Scotland could begin to threaten and when they did it was from set-pieces that they looked most dangerous.Alan Hutton rose to glance a header narrowly wide from a corner and on the stroke of half-time, Weir's effort was cleared off the line by Andrea Pirlo from a similar flag-kick.
In between those chances Italy were unlucky not to extend their lead.
Toni's snap-shot brought an excellent save from Gordon and the referee ruled out Di Natale's follow-up despite there looking to be little wrong with the finish.
With 45 minutes to rescue their Euro 2008 dream, Scotland raised their game in the second period and on that performance alone can count themselves unfortunate not to have gone on to take something from this match.
It was on 65 minutes that parity was restored and when the goal came it was no more than Scotland's endeavour had deserved.
After Hutton was felled following a marauding run, James McFadden's free-kick fell into the path of Lee McCulloch who forced a point-blank save from Gianluigi Buffon.
The ball dropped kindly to skipper Ferguson who was able to stab home from a couple of yards, though replays showed the Rangers midfielder may have been narrowly offside.
The goal stood and that set up a fascinating final quarter of the game with Scotland needing to score, but with Italy knowing a draw would be enough for them to qualify.
Inevitably it was the home side that began to dominate possession and chances as the Azzurri seemed to content to soak up the pressure and run down the clock.
Despite their best efforts, Scotland were never able to fully test Buffon again with arguably their best chance arriving at the feet of the ever-willing McFadden, who was the architect of most of Scotland's best play.
His far-post lunge following a neat exchange with McCulloch was unable to direct the ball inside the post, with Buffon struggling to get across his goal.
With the seconds ticking by it looked increasingly like the match and the qualifying campaign was going to end in bitter disappointment for the 52,000 Tartan Army inside Hampden.
And so it proved as Panucci killed the game off deep in stoppage time, rising to meet Pirlo's far-post free-kick to steer the ball past Gordon and his side on to next summer's finals.