Andrea Pirlo ruined Walter Smith's opening night as Scotland manager here in Milan with a pair of stylish free-kicks that almost certainly condemned the raucous Tartan Army to a watching role when the World Cup finals unfold next summer.
The Scots now have a virtually impossible task of claiming even the runners-up spot after losing to the group five favourites. They have gathered just two points from four games but this one under Smith was in stark contrast to the wretched sequence before under Berti Vogts.
The display at the San Siro stadium was laced with adventurous passages in the second half when Nigel Quashie and Kenny Miller might have equalised. However, Pirlo ended the hosts' anxiety by curling a 25-yard free-kick past Craig Gordon five minutes from time after Giorgio Chiellini had drawn a foul from Miller, eclipsing his free-kick just before the interval. Of greatest concern to Fifa will be the sight of riot police trying to quell local hooligans which is almost certain to prompt an inquiry.
Smith started his new life in charge of Scotland by embracing something old and something new. David Weir was back in the international fold with his former Everton manager after an exile under Vogts while Paul Hartley made his debut at the age of 28.
Not even the torrential downpour that descended on Milan and turned the stadium's environs into a swamp could dampen the spirits of the Tartan Army, who always travel in hope more than expectation, but whose voices lifted up to the San Siro's rafters.
Hartley's introduction to international football was instant as Rino Gattuso flattened him in the opening minute. However, the Hearts player regained his composure quickly enough to release Miller in the seventh minute whose advance into the area was only averted when Marco Materazzi conceded a corner.
It was the Scots, though, who had to absorb the bulk of the early pressure. Antonio Cassano and Francesco Totti displayed a telepathy that illustrated their club partnership at Roma, and when Jackie McNamara brought down Cassano on the edge of the box after nine minutes, Smith's defensive wall had to stand form to block Pirlo's effort shot Robert Douglas touched Mauro Camoranesi's effort from the rebound wide for a corner.
Douglas then got down well to hold a fierce free-kick from Totti. The Scotland goalkeeper excelled in the 25th minute when Cassano eluded his marker to reach a long ball, steering it up over Douglas whose swift reaction allowed him to touch the ball over.
There was little respite for Scotland, largely because Cassano was camped in an offside position trying to profit from his deception. He had the ball in the net but not surprisingly he was ruled offside.
However, Italy finally made the breakthrough 10 minutes before the interval. A mistake by Gary Naysmith forced McNamara to defuse the situation by bringing down Alberto Gilardino and that allowed Pirlo to whip a sublime free-kick over the wall from 20 yards that flew beyond Douglas. That was Douglas's last involvement. The Celtic goalkeeper had to concede to a groin strain and was replaced by Gordon
It was, though, a different Scotland who re-emerged for the second half. The containing policy that lacked a cutting edge was abandoned as Smith's side played the contest much further up the pitch. They were almost rewarded twice within a matter of minutes when they cut the Italian defence wide open. The first occasion in the 51st minute was a delightful move that began with Weir's long diagonal ball to the left wing that was headed inside by Lee McCulloch to Hartley, whose deft flick picked out Quashie. The midfielder composed himself and unleashed a venomous left foot volley that was acrobatically pushed wide by Gianluigi Buffon.
Confidence surged through the Scotland players and Miller ought to have equalised minutes later when Barry Ferguson and Hartley combined to release the striker who had got in behind Materazzi. Miller advanced but struck his shot straight at the goalkeeper and failed to finish from the rebound.
However, Scotland had taken the sting out of their hosts. The Scots' crisp passing game was met with a crescendo of backing from their fansas Italy struggled to get the ball. The bravado was symbolised by Hartley nutmegging Materazzi before Naysmith brought another save out of Buffon.
The mood, though, was wrecked with 20 minutes left when police had to wade into Italian fans in the lower tier, underneath the Scotland support. The stick-wielding hooligans were met with batons before tear gas was fired by the riot police.Reuse content