Italy's Under-21 side kicked off a new cycle with a 3-2 defeat in Russia as they prepare for their qualifying campaign for the 2011 UEFA European Under-21 Championships.
Coach Pierluigi Casiraghi, who renewed his contract following a semi-final finish at this summer's tournament in Sweden, is beginning a new two-year cycle that he hopes will end with his side lifting a record-extending sixth European title in Denmark.
With a whole host of players now no longer eligible, Casiraghi had to name a mainly fresh squad to test out in the friendly in St Petersburg.
Several players made their debuts, including Manchester United's Federico Macheda who was starting alongside Inter's Mario Balotelli and Parma's Alberto Paloschi in the Azzurrini attack.
It was Paloschi, owned by Milan, who gave Italy the lead shortly before the interval, pouncing on a series of defensive blunders by the hosts.
However, with substitutions disrupting the flow of the game, Russia got their equaliser six minutes after the restart through Fyodor Smolov's long shot.
Pavel Mamayev then converted a dubious penalty award on the hour-mark to give the home side the lead, before getting himself sent off 10 minutes later for a late challenge.
As the visitors pushed forward for an equaliser, Aleksandr Salugin wrapped up the win in stoppage time.
Italy did respond through an Andrea Rispoli header, but the goal proved be too little, too late.
Casiraghi's men will now turn their attention to the 2011 qualifying campaign and to their opening game against Wales in Swansea on 4 September. The five-time European champions are in qualifying Group 3, which is already under way, along with Bosnia-Herzegovina, Hungary and Luxembourg.
Group 3 Results
Friday 27 March
Luxembourg 0-0 Wales
Tuesday 31 March
Wales 5-1 Luxembourg
Saturday 6 June
Hungary 3-0 Luxembourg
Wednesday 10 June
Luxembourg 0-1 Hungary
Wednesday 12 August
Wales 4-1 Hungary
Group 3 Standings:
 WAL - PLD: 03 - PTS: 07
 HUN - PLD: 03 - PTS: 06
 LUX - PLD: 04 - PTS: 01
 ITA - PLD: 00 - PTS: 00
 BOS - PLD: 00 - PTS: 00
Next Group 3 Fixtures
Friday 4 September
Bosnia-Herzegovina v Luxembourg
Wales v Italy
Tuesday 8 September
Italy v Luxembourg