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First, you have to select your team and choose the default settings of your season. Next, you have to go to your schedule. Keep paging through the calendar until you are at the last month of the season. Select the last day and it will ask if you want to simulate. If you tell it to simulate up to that point, it will simulate the entire season.

Hope this helped!

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Q: How do you simulate entire season on NBA live 08?
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