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Milan will represent Italy next year and we canNOT be draw into a group with another Italian team ... last year was an exception because Pool set a precedent when a team wins the CL without qualifying thru the domestic competition, that's why they could and were drawn with another English team in the groups, they still represented England though it's just that an exception was made.
Since then, however, the rules have been changed and Milan this year will be just like any other team in the draws - no exceptions, which means that we cannot play with another Italian team in the groups.
As for the homegrown players, I think there is a good chance that the rules from this season will be changed, so I guess we'll have to wait and see what the new ones will say ...
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"Everyone creates his own luck" - Carlo Ancelotti
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