Milan’s return to the Mapei Stadium on Sunday brings an uncomfortable recent memory back into view. Sassuolo won 2-0 there last season, in a performance that stood among the poorest of Massimiliano Allegri’s second spell in charge, and the Rossoneri now face a coach whose own Milan story ended on an unusually calculated note.
Key takeaways
- Milan visit Sassuolo on Sunday, with kick-off scheduled for 18:00.
- Sassuolo, coached by Alberto Aquilani, beat Juventus earlier this season.
- Aquilani spent the 2011-12 campaign on loan at Milan from Liverpool.
- A contractual clause made substitute appearances worth half a match towards a compulsory purchase condition.
- Milan stopped Aquilani reaching the threshold that would have forced a permanent transfer.
Aquilani meets Milan again
The restart after the extended break gives Aquilani another meeting with a former club. The Sassuolo coach is regarded as a promising young manager with a record of developing emerging players, and he has already produced one notable result this term by overcoming Juventus, another side he represented during his playing career.
His time at Milan was far shorter. Aquilani arrived in the summer of 2011, aged 27, still looking for the settled status that had seemed possible after his impressive early years at Roma. Liverpool had paid €20 million for him, but his spell in England did not develop as hoped. Loans to Juventus and then Milan followed.
At Milan, he entered a squad carrying the confidence of a title-winning season and considerable midfield competition. Clarence Seedorf, Massimo Ambrosini, Mathieu Flamini and Mark van Bommel were among the established options available to Allegri.
The agreement negotiated by Adriano Galliani was a loan arrangement which would become permanent for €6 million, with a further €1 million in bonuses, if Aquilani reached 25 appearances. His salary was around €2 million. On arriving, he spoke of the added responsibility involved in following Andrea Pirlo, while acknowledging that he was a different kind of player.
There was a promising beginning. Allegri used him in more than one position: sometimes behind the forwards in a 4-3-1-2, at other times as a midfielder. Aquilani set up a goal on his debut against Lazio and scored at Napoli. By the Christmas period, he had registered one goal and six assists, starting regularly and making 18 appearances across all competitions, including the Champions League.
An injury, then a contractual ending
The season changed in January when Aquilani suffered an ankle problem. The initial expectation was a month out, but the absence stretched first to two months and then three. Conservative treatment did not resolve the issue, and when he returned in March he was not at his previous level physically.
Allegri increasingly selected Urby Emanuelson in the advanced midfield role, while Aquilani’s involvement became sporadic. By mid-April, with Milan contesting the Scudetto race against Juventus, he had reached 22.5 appearances rather than 23.
The unusual figure reflected the wording of the deal with Liverpool: a starting appearance counted as one match, while a substitute outing was valued at 0.5. That detail mattered as Milan approached the 25-match trigger for the compulsory purchase.
Aquilani’s final Milan appearance came against Novara in May 2012, a match shaped by the farewells of Filippo Inzaghi, Alessandro Nesta, Gennaro Gattuso and Seedorf. It was the closing scene for several important figures, and also for Aquilani’s brief Rossoneri chapter.
Galliani, with Allegri’s approval, decided not to allow him to reach the contractual threshold. Aquilani later recalled that Galliani invited him to his office and explained the situation directly, an honesty he said he appreciated. Liverpool, however, wanted to secure a sale and felt Milan had handled the arrangement unfairly, choosing to speak with other clubs instead.
In the summer of 2012, Fiorentina signed Aquilani on a free transfer. He would go on to enjoy three strong seasons in Florence. Now, from the Sassuolo bench, he has the opportunity to add another difficult afternoon in Emilia to Milan’s recent history.
