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Playing Portuguese liga. Won 10 seasons in a row. I've won manager of the year TWICE. Now, I know winning the league doesn't guarantee you the award, but multiple times I've gone unbeaten, won the league by at least 15 points or so, and it gives it to someone else. This last season, in fact, I won EVERY SINGLE GAME. 34 wins. No losses. No draws. Who won the award? Paulo Sousa coaching Benfica. 2 draws. 6 losses. I don't understand how this game is figuring it out.

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Usually, in my Milan save, the Manager of The Year award goes to the most overachieving manager. Probably because of the improvements of their league position compared to last year (or if they are a promotion team). Or because their squad total wages so low that it doesn't seem to warrant their current (good) position. Other than that, I don't know why you didn't get the award.
 
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