Milan will go down as one of the classic teams of the decade, if only for the players that wore the Rossoneri shirts. It featured a true modern legend in Paolo Maldini, as well as Costacurta, Stam, Cafu, Nesta, Serginho, Pirlo, Redondo, Seedorf, Gattuso, Boban, Kaka, Rui Costa, Leonardo, Rivaldo, Ronaldinho, Shevchenko, Ronaldo, Inzaghi, Crespo, Pato…in fact, more true world-class footballers than any club throughout the decade.

Reaching three Champions League finals in five years from 2003-07 was an incredible achievement, although Ancelotti’s time at Milan only brought one Scudetto in eight years, which is why it is relatively far down this list.

The wonderful thing about Milan’s side was that they were able to deploy so many creative players in the centre of midfield, and the key to this was Andrea Pirlo. Not enough attention is given to Pirlo’s remarkable change in position. At the turn of the century, he was held up as the next great trequartista, the new Roberto Baggio, and excelled for Italy’s under-21 side playing just behind the forwards, both creating and scoring goals. Unfortunately, Inter couldn’t find any room for him in their side, and they loaned him out to his first club, Brescia, in order to learn first-hand from Baggio, the master. Carlo Mazzone, however, completely reinvented Pirlo’s game, and deployed him in front of the back four, sitting and creating from deep – using his incredibly accurate long-range passes to great effect.

Milan saw glimpses of how good he could be in a deep role, and bought him from their city rivals for £12m. But his first season at Milan was unspectacular – they spent most of the campaign in 5th or 6th place, and with Carlo Ancelotti knowing he would lose his job if he didn’t qualify for the Champions League, now was not the time for tactical innovations. Pirlo’s creativity was overlooked in favour of the experience of Demitrio Albertini, the reliability of Massimo Ambrosini, or the energy of Massimo Donati, another young Italian central midfielder Milan had bought in 2001. With Fernando Redondo set to come back from injury in Pirlo’s position, his days at Milan looked numbered.

The departure of Albertini in the summer of 2002 coincided with the arrival of Pirlo’s former Inter teammate, Clarence Seedorf. With Manuel Rui Costa also a regular, Milan were playing with two playmakers high up the pitch, and the opposition’s central midfield were forced to play deep, and focus on remaining compact in front of their defence. With Gatusso providing enough energy for two holding midfield players, Pirlo was free to create in front of his own back four – and suddenly Milan had Rui Costa, Seedorf and Pirlo, three classic Number 10s, in the centre of midfield.

Milan won the Champions League that season, with a solid back four and two out-and-out strikers. A fairly standard 4-3-1-2 shape (above left), it was the tireless running of Seedorf and Gatusso that meant Milan’s ultra-central approach worked.

Some sides might have rested on their laurels having won the European Cup, but Milan went ahead and bought a young Brazilian named Kaka. And, with Pippo Inzaghi injured for much of the campaign, Milan went even further in their obsession with central playmakers, often playing Kaka, Rui Costa, Seedorf and Pirlo in central midfield, with Shevchenko upfront on his own (above right), scoring 24 league goals that season. Milan won the league by 11 points.

But whilst their midfield offered numerous points of attack, it was often exposed defensively. This happened twice in the Champions League, in two of the most incredible comebacks in the history of European competition. In 2004, Milan thrashed Deportivo 4-1 at home in the first leg of their quarter-final and appeared to be comfortable, only to suffer a humiliating 0-4 defeat at the Riazor. The infamous episode in the 2005 Champions League final further demonstrated Milan’s problem – they led 3-0 at the break and still fell apart and lost the tie.

These embarrassments convinced Ancelotti that he needed more bite in midfield, with Seedorf and Gattuso getting older, and not able to cover as much distance as previously. Therefore, another holding midfielder, in Massimo Ambrosini was inserted, with Seedorf pushing further forward and Kaka playing off a lone striker (left). The decreased threat from the centre of midfield was compensated with two attacking, pacey full-backs, meaning Milan offered the same level of attacking threat whilst remaining solid defensively, and they regained the European Cup in 2007.

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