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    AC Milan - HISTORIC MATCHES: ROUND OF 16
    HISTORIC MATCHES: ROUND OF 16
    HISTORIC MATCHES: ROUND OF 16
    HomeAwardsHISTORIC MATCHES: ROUND OF 16
    ...HISTORIC MATCHES: ROUND OF 16

    HISTORIC MATCHES: ROUND OF 16

    AwardsNovember 21st 2022

    From 1963 to 2007: voting begins for your favourite match

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    From 1963 to 2007, from our first Champions League to our seventh. Between the break and the end of the year it is always time to look back, but also an opportunity to re-open the Rossoneri's history book and relive the glorious past. We have chosen sixteen memorable matches to find the most unforgettable in the hearts of the AC Milan fans. It will be up to you, the fans, from the Round of 16 onwards, to vote and then decide your favourite through the club's official social channels. Finals in Europe, derbies in Italy and more. Here are the details and the pairings:

    • AC Milan v Benfica 1963 (first Champions League win) v AC Milan v Liverpool 2007 (seventh Champions League win)
    • Red Star v AC Milan 1988 (4-2 after penalties Champions League qualification) v AC Milan v Ajax 2003 (3-2, Champions League qualification)
    • AC Milan v Steaua București 1989 (third Champions League win) v AC Milan v Barcelona 1994 (fifth Champions League win)
    • AC Milan v Inter 1984 (2-1, Serie A win) v AC Milan v Inter 2004 (3-2, Serie A win)
    • Napoli v AC Milan 1988 (3-2, Serie A win) v Juventus v AC Milan 2003 (sixth Champions League win)
    • AC Milan v Nacional Medellín 1989 (second Intercontinental Cup win) v AC Milan v Benfica 1990 (fourth Champions League win)
    • AC Milan v Real Madrid 1989 (5-0, Champions League qualification) v Inter v AC Milan 2001 (6-0, Serie A win)
    • AC Milan v Ajax 1969 (second Champions League win) v AC Milan v Manchester United 2007 (3-0, Champions League qualification)