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For my sins I have played the game a lot managing Derby. I have noticed that after getting past the 2nd round in the league cup (pretty much always needing extra time and penalties versus one of the worst teams in the football league - but that's another matter) I get drawn against a fellow Premier League team in the 3rd round and the fixture list has me playing them in the PL 3 days after the cup match. I wonder if the game engine somehow forces a draw versus a PL team in the 3rd round if your Board sets reaching the 4th round as their minimum objective??
Ive found that when i'm playing a network game, i tend to get drawn against the other human player.
I've started 4 network games and on 3 occasions i drawn the other human player in the 3rd or 4th round of the cup. Quite annoying as much rather play in final !
I've drawn Real Madrid three years in a row in the first knockout round in the Champions League. It is such a bizarre coincidence because it means they have also managed to somehow finish second in their group for all three years. The past two years, I have drawn Chelsea in the second knockout round.