Five years ago, AC Milan won the Champions League, the seventh time the famous cup had been added to their trophy cabinet. The victory helped cement the Rossoneri’s second place in the pantheon of winners, just behind Real Madrid, who boast two more wins with nine European Cups to their name.

That team, coached by Carlo Ancelotti, won the Champions League after a troubled season, marked by the Calciopoli scandal which had seen Milan start the Serie A campaign with an eight-point deduction. Ukrainian striker Andriy Shevchenko had also left before the season kicked off, a vital player whose goals fired Milan to the Scudetto in 2003/04 and a Champions League final win over Juventus in 2002/03 (from the penalty spot).

Milan’s squad, even without Shevchenko, was full of players at the top of their game. Paolo Maldini and Alessandro Nesta bossed the defence, Clarence Seedorf and Andrea Pirlo ran the midfield, with Brazilian playmaker Kaka pulling the strings and goal-poacher Filippo Inzaghi finishing chances aplenty.

Today, a trip to Milan’s Milanello training camp would only reveal two survivors of the team which put Liverpool to the sword in the 2007 Champions League final: Massimo Ambrosini, the current captain and Daniele Bonera, who was a reserve in the 2006/07 squad.

There is no clearer sign of the revolution which took place at Milan over the summer. Following the world financial crisis and the situation which in particular afflicted owner Silvio Berlusconi and his Mediaset TV company, the former Italian prime minister and his right arm, vice-president Adriano Galliani, decided to sell or release the club’s top players, particularly those on the biggest and most lucrative contracts. Milan moved to let Nesta, Gianluca Zambrotta, Seedorf, Mark van Bommel, Inzaghi and third-choice goalkeeper Flavio Roma leave after the expiry of their contracts. Meanwhile, the Rossoneri opted not to make an offer for midfielder Alberto Aquilani, who had spent the season on loan from Liverpool.

Then, in June, after a long series of discussions, Berlusconi and Galliani dropped a bombshell. Brazilian defender Thiago Silva and Swedish striker Zlatan Ibrahimovic, Milan’s two best players, were being sold to Paris Saint-Germain. The club’s fans were furious as the side appeared more dismantled than renewed. Coach Massimiliano Allegri was backed to continue, but handed a far lesser quality of player, with the arrivals of full-back Francesco Acerbi from Chievo and defender Cristian Zapata (Villarreal) to bolster the defence, and Bakaye Traore (Nancy) and Riccardo Montolivo (Fiorentina) to add to the midfield. While Montolivo was hailed as a good acquisition, having impressed with Italy at Euro 2012, the other were widely dismissed as “not Milan standard” by sections of the club’s faithful.

If the defence and midfield was a source of concern, the attack was looking even more threadbare. Galliani moved to bring in Giampaolo Pazzini from Inter, with Antonio Cassano going the other way; Cassano had cut an unhappy and depressed figure at Milanello following Ibrahimovic’s departure and was only too pleased to join the club he had supported as a boy. This activity though was still not enough and Gialliani had even more work to do in the last days of the summer transfer window, loaning forward Bojan Krkic from Roma via Barcelona and, most importantly of all, buying Nigel de Jong from Manchester City, a new arrival to give strength and reliability to the Rossoneri midfield.

And so, a completely different team will now battle in Milan’s colours in the Champions League – and this against a background of thoroughly disillusioned supporters. On the first day of the new Serie A season against Sampdoria, only 35,000 went through the turnstiles to cheer the Rossoneri on, and only 21,000 decided to buy a season ticket, the lowest total of the Berlusconi era. That afternoon, Milan lost to the Blucerchiati 1-0 and clearly lacked the aggressive attitude which had so defined their play over the last two years. Milan’s second Serie A game was better, with a 3-1 victory. The performance was not stellar, but Pazzini bagged a memorable hat-trick and some confidence seemed to be seeping through the team. The third though reset the clock, as lowly Atalanta visited the San Siro and left with a 1-0 win. In Milan, there is a real sense of not knowing quite what will unfold domestically from here on in.

It is though perhaps the Champions League which will see how this new-look Milan side live up to their predecessors. In a group containing Anderlecht, Zenit St. Petersburg and Malaga, the appearance of an easy draw could be deceptive. Zenit, managed by Luciano Spalletti, bought Brazilian striker Hulk and Belgian midfielder Axel Witsel at a combined cost of around €80M before the transfer window closed and are in many ways now favourites to top the group, while Anderlecht and Malaga could each cause the Rossoneri difficulties if Milan do not hit the ground running.

Milan look set for a difficult season. Recently, after weeks of arguing, coach Allegri and vice-president Galliani settled on the club’s goals for 2012/13: A place in next season’s Champions League and at least progress to the Round of 16 this year. This is another era and another type of AC Milan.

Best bets for the 2012/13 Champions League? Read our tips here.