Inzaghi equalized in the 67th minute with a volley off a cross by Clarence Seedorf, setting the final score to 1–1 and sending the game to penalties, which Barcelona won 3–1 to lift the trophy.

[17] During the league winter break, Milan traveled to Dubai where they resumed their trainings and played a friendly match against local club Al-Ahli on 2 January 2011.

The match ended 2–1 for the Rossoneri, who opened the scoring through Clarence Seedorf late in the first half, and then doubled their lead through youth team striker Giacomo Beretta in the 73rd minute, before the hosts pulled one back with a 25-yard strike by Hasan Ali.

After missing a couple of early chances with Ronaldinho and Thiago Silva and having a goal disallowed for offside, they went behind in the 31st minute, as Erjon Bogdani headed in a cross from Ezequiel Schelotto.

Milan had another goal called off early in the second half, this time for handball, but in the end were unable to score, with Ibrahimović missing a penalty in the late stages of the game.

In the last minutes, both teams missed the chance to claim the victory: Gianluca Zambrotta hit the crossbar with a powerful strike from just outside the box, while Hernanes was denied by a save from Abbiati.

The Rossoneri went ahead in the 22nd minute through Robinho, who played a one-two with Massimo Oddo and shot the ball past Napoli goalkeeper Morgan De Sanctis from just inside the penalty area.

The Rossoneri had a good start, but failed to score: Zlatan Ibrahimović hit the crossbar with a 25-yard shot in the seventh minute, while Pato was called offside moments later when he was one-on-one with the goalkeeper.

Shortly after the half-hour mark, Milan doubled their lead through Mathieu Flamini, who received the ball from Zlatan Ibrahimović inside the penalty area and put it past Bari goalkeeper Jean-François Gillet into the net.

[43] Three days after playing the last match of the Champions League group stage against Ajax, Milan travelled to the Stadio Renato Dall'Ara to face Bologna.

[44] But in the last match before a three-week winter break, Milan lost 1–0 to Roma at the San Siro, the lone goal being scored by former Rossonero striker Marco Borriello.

After a scoreless first half, during which the hosts hit the woodwork once, Milan went on to win the game thanks to the first career goal by 20-year-old Sierra Leonean midfielder Rodney Strasser five minutes before time.

The visitors took the lead in the 35th minute through Antonio Di Natale, who slid the ball into an empty net after Gökhan Inler hit the post; but the Rossoneri equalised in first-half injury time with Pato, who scored following a low cross by Ibrahimović.

[49] After a victory over Bari in the Coppa Italia round of 16 in mid-week, Milan returned to winning ways in the league too, by defeating Cesena 2–0 at home on 23 January.

The Rossoneri took the lead in the last minute of the first half, when Cesena defender Maximiliano Pellegrino slid the ball into his own net while attempting to prevent Ibrahimović from shooting, following a cross by Cassano.

Milan had taken the lead shortly before the half-hour mark through Pato, who converted a low cross by Ibrahimović, but the hosts equalised in first-half injury time with a goal by Antonio Floro Flores from deep inside the penalty area.

The lone goal was scored by Gennaro Gattuso midway through the second half, as his left footed attempt from the edge of the penalty area was not held by Juventus goalkeeper Gianluigi Buffon.

The hosts' goal was scored by defender Dorin Goian, who chested the ball inside the six-yard box following a corner kick and put it past Milan goalkeeper Christian Abbiati.

[60] The loss against Palermo meant that Milan's gap over cross-city rivals Inter at the top of the table was reduced to two points, before the two side met in the second Derby della Madonnina of the season on Saturday, 2 April.

Shortly before half-time, Inter had a couple of a chance to tie, first with a header by Thiago Motta that was saved by Abbiati, then with Samuel Eto'o, who fired wide from a few yards.

Due to the high number of injuries, head coach Massimiliano Allegri was prompted to put newly arrived duo of Mark van Bommel and Urby Emanuelson in the starting line-up.

Early in the second half, the hosts pulled one back through Stefano Guberti, but this did not prevent the Rossoneri from winning the game and making it through to the semi-finals, where they will face Palermo.

[80] The Rossoneri were drawn in the group G alongside Spanish La Liga runners-up Real Madrid, Dutch Cup winners Ajax and French side Auxerre.

[86] In the sixth and last game of the group stage two weeks later, Milan suffered a harmless 2–0 home defeat against Ajax, with second half-goals by Demy de Zeeuw and Toby Alderweireld.

Milan kept pressing forward, but 10 minutes from time they were caught short on a counterattack led by Aaron Lennon, who provided the assist for Crouch's winning goal.

[94] The Rossoneri went on to sign Sokratis Papastathopoulos for an undisclosed fee from Genoa, who also took on co-ownership of youngsters Rodney Strasser, Nnamdi Oduamadi and Gianmarco Zigoni as part of the deal – though only the latter actually left Milan.

[99] As the last week of the transfer window approached, director general Ariedo Braida revealed that Milan might be interested in signing Swedish star Zlatan Ibrahimović from Barcelona.

[102] After some days of talks, on 29 August Milan officially announced to have signed Ibrahimović on a free loan with the option to fully purchase the athlete's playing rights for €24 million at the end of the season.

[105] At the same time, three players left the club: Kakha Kaladze and Klaas-Jan Huntelaar moved to Genoa and Schalke 04 respectively,[106][107] while Marco Borriello was loaned out to Roma.

[116][117] Milan went on to complete two more signings in the second half of January, bringing in Dutch duo of left winger Urby Emanuelson and midfielder Mark van Bommel, from Ajax and Bayern Munich respectively.