Slovenia 1 - 0 Italy
Cesar 82 (S)
The Azzurri rattled the woodwork twice, but it was Slovenia who grabbed the goal as Marcello Lippi falls to his first competitive defeat. Italy had also lost 1-0 in their last trip to their neighbours, a 2002 friendly.
Marcello Lippi gave Cagliari wide man Mauro Esposito his international debut for this match, while it was Francesco Totti's first appearance under the new Coach after a ban and injury had ruled him out since his untimely Euro 2004 exit.
The Azzurri started out with the 4-2-3-1 system that had been used with varying degrees of success by Giovanni Trapattoni, with Alberto Gilardino keeping his centre-forward role as Christian Vieri and Alessandro Del Piero are injured, while Antonio Cassano was dropped due to his poor form.
Within the first three minutes Italy had thumped the woodwork when a Totti free kick came out to Gilardino and the Parma man clipped the outside edge of the upright from seven yards.
Daniele Bonera was booked after just six minutes for a tough tackle on Acimovic in midfield and will be suspended for the Belarus match. There was panic soon after when Gianluigi Buffon rushed off his line to gather a free kick floated into the box and didn't quite get a handle on it, so he had to clear the ball with his feet as it was outside the area.
Slovenian goalkeeper B Mavric reacted well to a deflection on Totti's free kick, but the Azzurri couldn't have gone closer than on 17 minutes when Gilardino's tap-in from a Mauro Camoranesi cross was fingertipped just past both the post and the desperate last gasp slide of Esposito.
However, there was chaos in the Italy area on 26 minutes when a Ceh corner kick was accidentally headed on to his own crossbar by Gianluca Zambrotta and Siljak was unable to turn in the loose ball with a bicycle-kick.
Camoranesi and Esposito switched wings and the Argentine-born winger found more room down the left, skipping past a challenge and firing just over the bar, even if he probably should have rolled it across to the unmarked Totti.
Esposito was brought down on the very edge of the box and Totti drilled the resulting free kick just past an unmarked Gilardino at the back post.
Camoranesi just failed to get on the end of Esposito's cross and moments later Gilardino was halted in a one on one situation with the goalkeeper for an extremely dubious offside decision that replays proved to be incorrect.
The Parma forward was troubling the Slovenian defence and rose to reach a Totti free kick only for Mavric to pluck his header out of the air. In the closing moments of the first half Esposito sprinted forward on the counter-attack, but M Mavric did well to cut him off.
Italy's first real chance of the second half saw Zambrotta cut back for Totti and his half-volley was bravely blocked by Mitrakovic inside his own penalty area.
There was also a scare for Buffon, as Acimovic cut a fine pass through for Siljak, who turned Fabio Cannavaro and blasted over the bar from a promising position.
On the hour mark Gilardino and Totti combined well for the Roma captain to drill a powerful effort just a little too high.
The rain was pouring down on Nova Gorica and it became increasingly difficult for the two sets of players to stay on their feet.
Esposito thought he had scored the opening goal on 68 minutes when he sprinted on to a Gilardino through ball, but the Cagliari debutante only shook the side-netting.
It was their last contribution to the game, as Esposito and Gilardino made way for Stefano Fiore and Luca Toni. Totti was moved up to a support striker role and a more traditional 4-4-2 system.
The two substitutes very nearly combined for a goal within moments of stepping on to the pitch. Fiore's floated cross was kept in play by Camoranesi and Toni's rising shot rattled the underside of the crossbar.
Totti was furious when he charged into the box and fell under a challenge from Mavric, but the referee correctly waved play on.
However, after all Italy's pressure and wasteful finishing, it was Slovenia who took the lead with eight minutes left on the clock. Ceh floated a free kick towards the back post where substitute defender Cesar was allowed a free header from six yards.
Marco Di Vaio was already set to replace Camoranesi, but his entrance became even more crucial after this goal. Italy poured forward with Totti firing just wide and Di Vaio closed down by Cesar as he prepared to pull the trigger.
Slovenia: B Mavric; Pokorn, M Mavric, Mitrakovic (Cesar 76), Karic (Dedic 70); Komac, Ceh (Lazic 87), Seslar; Acimovic; Siljak, Sukalo
Italy: Buffon, Bonera, Cannavaro, Nesta, Zambrotta; Gattuso, De Rossi; Camoranesi (Di Vaio 82), Totti, Esposito (Fiore 69); Gilardino (Toni 69)
Ref: De Bleeckere (Bel)
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@juventus2: Believe me, all the spirit in the world would not save Slovenia from an on form Italy.