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You can protect most of your money from other players by depositing it into the bank, by doing this you will only have to pay out 10% of your money if you lose.
If you obtain the higher end coaches you will be able to unlock more training spots which will allow you to train your team quicker.
The only way you can improve your players for free is to constantly train them.
A good strategy to put together a series of wins is to search for lower tier opponents, teams to look out for are those whose featured player has low stats. Tap the 'Reload' button to refresh the list of rivals when there are no more weak opponents left.