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Failed Superteams- AC Milan 2008-2014

After years of success domestically and in Europe, AC Milan entered a period of decline in terms of trophies and finances. This was just after the Champions League glory of 2007 in Athens. But… How much do you know about this period of AC Milan’s history.
source- Wikipedia
From 2008/09
Quiz by
DeanPelton
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Last updated: January 2, 2026
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First submittedJanuary 2, 2026
Times taken17
Average score75.0%
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Answer
Which Brazilian legend did Milan sign from Barcelona in 2008 for €21m?
Ronaldinho
Which prolific striker did Milan re-sign from Chelsea on loan that same summer?
Andriy Shevchenko
Despite winning the UCL two seasons prior, Milan were in the UEFA Cup in 2008/09 and got knocked out in the Round of 32 by which German club?
Werder Bremen
Which young Brazilian centre back was signed from Fluminense for €10m?
Thiago Silva
Which Dutch centre-forward was signed from Real Madrid for €15m?
Klaas Jan Huntelaar
Which winger was signed from LA Galaxy on loan
David Beckham
Despite these signings, Milan had a poor UCL campaign, getting knocked out at the Round of 16 by which team after being thrashed 7-2 on aggregate?
Manchester United
Who was signed on loan from Barcelona in 2010?
Zlatan Ibrahimovic
Who was signed for €18m from Manchester City?
Robinho
Again, Milan experienced an unsuccesful UCL campaign once again after they were knocked out in the Round of 16 by Tottenham who beat them 1-0 on aggregate with a goal at the San Siro- who scored it?
Peter Crouch
Fast forward to 2013/14 who did Milan re-sign for free from Real Madrid
Kaka
2013/14 was particularly miserable with Milan finishing 8th in the league which was their lowest league finish since when
1997/98
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