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Marcello Lippi fielded the trident attack, but it took a brace of Andrea Pirlo free kicks to get the better of a plucky Scottish side.
Antonio Cassano had never previously played under Coach Marcello Lippi due to injury and disciplinary problems, but he was given a starring role in the trident attack with Roma teammate Francesco Totti and Parma's Alberto Gilardino.
The Azzurri had to do without the injured Vincenzo Montella and Alessandro Nesta, while Gianluca Zambrotta was suspended, so Fiorentina's Giorgio Chiellini and Inter man Marco Materazzi stepped into the squad for this World Cup qualifier. It was an important game for Scotland, as manager Walter Smith was making his official debut.
The first real chance came after nine minutes, as Totti's low free kick was charged down by the defensive wall, then Chiellini saw his effort deflected just past the near post.
Another Totti set-piece from much further out - a good 35 metres - made it through the sea of legs and Rab Douglas did well to smother it.
There was some splendid play on 25 minutes when Andrea Pirlo's chopped pass came over the defence and to Cassano for a delightful flick with the inside of his foot, but Douglas saved the Scots by tipping it over the bar.
The goalkeeper fumbled a Totti low cross and Gilardino almost made the most of the error. Then Gilardino and Cassano both backheeled a Chiellini cross, though without enough power to trouble Douglas.
Gilardino's glancing header was also dealt with as the Azzurri began piling on the pressure and dominating possession.
Cassano thought he had opened the scoring on the half-hour mark when he lifted Totti's pass over Douglas, but it was disallowed for a very tight offside position.
There was no doubting the goal a few minutes later, as Milan midfielder Andrea Pirlo curled in a magnificent right-footed free kick from just outside the area. Douglas was left stranded by the wicked bend on the ball as it lifted over the wall and in at the near post.
There was more bad news for the Scots moments later, as Douglas was forced out with a groin problem and replaced by 22-year-old Craig Gordon.
Totti's deflected volley went out for a corner kick, and Gigi Buffon's first touch was to block a Kenny Miller cross from the left on 44 minutes.
Italy really should've gone into the break 2-0 up, as Cassano exchanged passes with Gilardino and rolled across for Totti only for the Roma captain to incredibly balloon over the bar from seven yards.
The rain intensified in the second half and made the pitch in the Stadio Giuseppe Meazza rather slippery. A scuffle broke out at the restart with Gennaro Gattuso and Nigel Quashie booked for their part. The Milan midfielder will be suspended for the next qualifier in Norway on June 4.
The Scots nearly grabbed an equaliser soon after as Italy were sluggish. Quashie burst down the right and saw his half-volley pushed out for a corner by Buffon.
Miller than outsprinted two defenders on Barry Ferguson's pass and had his finish been firmer then Buffon could've been in real trouble, but he and Cannavaro managed to smother the shot with some difficulty.
Cassano was perhaps a little too eager to play to the gallery and attempted to cut round the defender on Gilardino's headed pass rather than shoot when he had the space.
Cassano skipped past a couple of players on the byline and his cross into the centre was cleared by the Scottish defence. There was also a handling offence from McNamara, but it was involuntary.
Naysmith's central effort was easily held by Buffon. The atmosphere at the San Siro appeared to be relaxed, but police intervened to charge when violence broke out in the stands among a small group of supporters.
Daniele De Rossi was the first Azzurri substitute of the game as he surprisingly replaced his Roma teammate Totti, who had been steadily drifting out of the game after an impressive first half performance.
Cassano wasted another golden opportunity, trying to find space amid a crowd of Scottish defenders, and moments later De Rossi set up Gilardino only for the Parma striker to hesitate in the six-yard box.
Palermo centre-forward Luca Toni replaced Cassano for the final eight minutes, leaving two tall strikers upfront.
Mauro German Camoranesi's low cross was heading towards Gilardino in the centre before a desperate defensive intervention stopped the ball dead.
Chiellini fought valiantly to earn the ball back and got a free kick for Italy. It was at roughly the same spot as the opening goal and had exactly the same outcome, as Andrea Pirlo curled in another magnificent set-piece to leave the goalkeeper stranded.
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