| Fabio Grosso's late goal saved Italy from an embarrassing defeat in Scotland, but this was a very sluggish performance.
Marcello Lippi has pledged to stick with the trident attack all the way through the World Cup campaign, but was forced to leave Alberto Gilardino in the stands in favour of Udinese's Vincenzo Iaquinta due to a last-minute injury. Only Christian Vieri started from the strikers who beat the Republic of Ireland 2-1 in August's friendly, Francesco Totti coming in for Alessandro Del Piero.
Angelo Peruzzi made his Azzurri comeback in place of the injured Gigi Buffon and it was an emotional moment for former Glasgow Rangers midfielder Gennaro Gattuso.
Italy had their first scoring opportunity after just one minute, as a Totti free kick came out to Cristian Zaccardo and the goalkeeper reacted to block his shot at the near post.
Vieri then shrugged off Webster's challenge and broke away through the centre, though his long-range effort was well smothered by Craig Gordon.
However, it was Scotland who broke the deadlock after 13 minutes with Kenny Miller. Zaccardo was caught napping on a sweeping Paul Hartley cross and Miller rose to nod in past a helpless Peruzzi.
Palermo defender Zaccardo has disappointed during his international career so far, as his error also gave away a goal in Dublin last month.
Gianluca Zambrotta and Daniele De Rossi were booked and both will miss Wednesday's trip to Belarus through suspension. Overall the Azzurri's reaction was sluggish and gave away possession very easily.
It took a crucial intervention from Paul Hartley to prevent Zambrotta getting on the end of Andrea Pirlo's long pass. From the resulting corner kick, Pirlo and Zambrotta combined again and Gordon flapped the ball off the Juve defender's head.
Iaquinta connected with Pirlo's cross only to nod it over the bar from six yards in a wasteful error. Soon after, Vieri blasted off target and was flagged offside, though replays suggest he might not have been.
Gordon plucked Zambrotta's good cross off Iaquinta's head, while Totti was furious when Vieri fell in the area sandwiched between two defenders and saw his penalty appeals rejected.
Vieri was extremely unfortunate not to equalise on the stroke of half-time, when he hooked Totti's pass towards the net, but Weir dived in to deflect it round the post and Italy went into the break trailing Scotland.
Palermo fullback Fabio Grosso replaced his club teammate Zaccardo for the second half, making his ninth international appearance, moving Zambrotta over to the right flank.
Totti drilled wide from a promising position and promptly got himself booked. Mauro German Camoranesi, who was expected to start, came in for the disappointing De Rossi.
Vieri was caught offside at the end of a fine team move, but Alessandro Nesta had to make a crucial intervention to block Miller's dangerous counter-attack.
The Azzurri really should've equalised on the hour mark when Totti intercepted a Graham Alexander error and rolled the ball across for Vieri at the far post, but he somehow managed to sidefoot it over from six yards. It was a fairly similar opportunity to one that Vieri famously missed in the 2002 World Cup against South Korea, although the ball did bounce right in front of the Milan striker.
Lippi's final substitution was Fiorentina centre-forward Luca Toni for Iaquinta, leaving Del Piero on the bench.
Italy were pushing forward continually in the second half and eventually drew level at the 75th minute. Camoranesi's corner kick was nearly turned into an own goal, but Gordon's one-handed reaction save only went as far as substitute Grosso for an acrobatic volley. It was the first goal that Italy have ever scored on Scottish soil.
Toni and Vieri had efforts charged down as the Azzurri put the pressure on in the final stages.
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