| Hint | Answer | % Correct |
|---|---|---|
| Which Brazilian legend did Milan sign from Barcelona in 2008 for €21m? | Ronaldinho | 100%
|
| Which winger was signed from LA Galaxy on loan | David Beckham | 93%
|
| Fast forward to 2013/14 who did Milan re-sign for free from Real Madrid | Kaka | 93%
|
| Which prolific striker did Milan re-sign from Chelsea on loan that same summer? | Andriy Shevchenko | 86%
|
| Who was signed on loan from Barcelona in 2010? | Zlatan Ibrahimovic | 79%
|
| 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 | 71%
|
| Who was signed for €18m from Manchester City? | Robinho | 71%
|
| Which young Brazilian centre back was signed from Fluminense for €10m? | Thiago Silva | 71%
|
| Which Dutch centre-forward was signed from Real Madrid for €15m? | Klaas Jan Huntelaar | 64%
|
| 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 | 57%
|
| 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 | 57%
|
| 2013/14 was particularly miserable with Milan finishing 8th in the league which was their lowest league finish since when | 1997/98 | 43%
|