As some of their players’ contracts expired, Milan saw some of their players leave for free while investing once more in youth.
Stefano Pioli’s squad needed to be strengthened, so after the team won the Scudetto for the first time in 11 years and RedBird started taking over from Elliott, they went on the transfer market. Milan still made some significant moves in the market despite losing Alessio Romagnoli and Franck Kessié and operating once more within a tight budget.
Yacine Adli and Tommaso Pobega returned from their loan assignments, while Alessandro Florenzi and Junior Messias were purchased by Paolo Maldini and Frederic Massara. However, Charles De Ketelaere, who joined from Club Brugge for €32 million, is unquestionably the most significant acquisition of the summer.
With the addition of Malick Thiaw, Aster Vranckx, and Sergino Dest toward the end of the transfer window, Milan was able to provide Pioli with more defensive and midfield options. The Rossoneri signed three Belgian players in total during this window, including De Ketelaere, Vranckx, and free agent Divock Origi.
| Player Name | Position | Age | Arrived From | Details |
|---|---|---|---|---|
| Tommaso Pobega | Midfielder | 23 | Torino | Returned from loan |
| Yacine Adli | Midfielder | 22 | Bordeaux | Returned from loan |
| Junior Messias | Forward | 31 | Crotone | Permanent deal (bought-out), two-year contract, €4.5m |
| Alessandro Florenzi | Defender | 31 | Roma | Permanent deal (bought-out), three-year contract, €2.7m |
| Divock Origi | Forward | 27 | Free Agent | Permanent deal, four-year contract |
| Charles De Ketelaere | Forward | 21 | Club Brugge | Permanent deal, five-year contract, €32m + €3m bonuses |
| Malick Thiaw | Defender | 21 | Schalke | Permanent deal, five-year contract, €5m + €2m bonuses |
| Aster Vranckx | Midfielder | 19 | Wolfsburg | Loan (€2m) + option to buy (€12m) |
| Sergiño Dest | Defender | 21 | Barcelona | Loan + option to buy (€20m) |
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