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Why would you make a schedule as you go? There are lots of custom schedules available in the MODS Forum if you don't like what the game gives you.
How many games are you planning to play in your season? The game has no idea how long of a season you're planning to play. It goes by the schedule. If you simmed up to and finished the last games you have scheduled then OOTP can only assume the season is over, and it will begin scheduling off season events.
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