Last updated at 21:57pm on 17th November 2007 Scotland's Euro 2008 qualifying hopes were killed off by goals at the beginning and end of a pulsating 90 minutes at Hampden.
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Luca Toni shot Italy in front in the second minute but Scotland recovered to dominate the second half and Barry Ferguson bundled home a 65th-minute equaliser.
Great start: Luca Toni puts Italy in front in the first minute
With the Scots having given everything, Italy captain Christian Panucci headed an injury-time winner after a controversial free-kick award on the edge of the penalty area. It meant that the world champions, and their under-pressure coach Roberto Donadoni, leapt above France to top of the group and Alex McLeish's brave Scots fell agonisingly short of next summer's finals.
Whatever tactical plan McLeish had designed was destroyed with Italy's opening goal after just 70 seconds. It was a crushing blow and it came through a combination of brilliant execution, aided by shocking defensive work. The main culprit was Alan Hutton, who seemed to be remonstrating with a ball boy for throwing the ball back into play too quickly. While Hutton and Scott Brown's attention was diverted, a Gianluca Zambrotta throw-in fell to Antonio Di Natale.
The little Udinese midfielder, who has made such a big impact on Serie A this season, crossed and the towering Toni drove in his 13th international goal.
It could not have been a worse time to concede. The feeling was that McLeish would stick by his previously pragmatic team plan and try to contain the Italians, then spring into counter-attack or try to gain opportunities from dead-ball situations. But the dreadful start clearly had a massive psychological effect on the Scots, and you could sense the morale being drained.
For a spell the Italians looked sharp and in total control. It took Scotland until the 14th minute to gather themselves well enough to construct some positive attacks when James McFadden won a corner.
From that little pocket of pressure they claimed a penalty when Zambrotta looked to have handled inside the box from a Lee McCulloch shot. It happened so quickly and without the benefit of an immediate playback, the Italian certainly looked to have diverted the ball with the lower part of his arm.
Referee Manuel Mejuto Gonzalez decided otherwise to the fury of the Scots players, the bench and the Tartan Army.
Just after that, Stephen McManus was extremely unlucky when he came upfield in attack and sent a header just wide. There was a decent looking Scotland move in the 29th minute — the best so far. Some intricate passing ended with McCulloch free and seemingly in position to score. But his shot came far too late and was easily gathered by a keeper of Gigi Buffon's world class.
Craig Gordon made an exceptional save in the 31st minute and when the rebound was blasted past him by Di Natale, it looked good enough to stand. For a split-second it appeared that Scotland were two down and out of it, but the Spanish referee took the advice of one of his assistants and ruled offside. Television showed later that at worst it was level.
Could this be the break Scotland needed? The Scots were a shadow of the team who had disposed, not without difficulty of course, of France twice and Ukraine. The midfield could make no impression on the match and McFadden was stranded up front, working hard but with nowhere near enough service.
For all the ferocity of some of the tackling, at least the exchanges were largely of a non-violent, professional type.
There were some nasties between David Weir and Toni, the most awkward of strikers to contain. They did go beyond acceptable combat on a couple of occasions and just before half-time, Toni was shown a yellow card for a foul on the veteran Scot. Seconds later, Weir thought he had scored with a looping header from a Ferguson corner but Andrea Pirlo headed the ball out from under the crossbar.
The Scots, though, had battled back into contention and then came the breakthrough they so desperately needed. It came after a fine run down the right by Hutton, who teased Zambrotta and was brought down 20 yards out. McFadden's free-kick was not one of his best but the ball was diverted to McCulloch, whose shot could only be blocked by Buffon.
Ferguson was on to it quickly, from an offside position it has to be said, and steered the ball over the line for his first goal for his country for five years. Luckily for the Scots, the officials decided it was not offside and they were right back in business.
But their massive effort on a rainsodden pitch ended in heartbreak when Hutton was barged over but the free-kick went to Italy. Panucci struck as the Scots failed to clear and the dream was over.
SCOTLAND (4-1-4-1): Gordon; Hutton, Weir, McManus, Naysmith; Hartley; Brown, Fletcher, Ferguson, McCulloch; McFadden. Subs: McGregor, Alexander, Caldwell, Pearson, Robson, Boyd, Miller.
ITALY (4-3-3): Buffom; Panucci, Cannavaro, Barzagli, Zambrotta; Gattuso, Pirlo, Ambrosini; Camoranesi, Toni, Di Natale. Subs: Amelia, Oddo, Chiellini, De Rossi, Perrotta, Iaquinta, Gilardino.
Referee: M Gonzalez (Spain).
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