The odds are in the OP's favour if he has more chance of winning than losing and (if allowed to enter more than once) he ends up in profit. If he enters fewer than twenty times and wins, he'll be in profit, if his entries are more than the others combined, then the odds are in his favour.
That means the most entries he can have is nineteen and the others is eighteen or thirty-seven in total, if there are any more than thirty-seven entries in total, the odds are no longer in the OP's favour.