If you have an expansion capacity, your board can expand the stadium before building a new one. If you've filled your expansion capacity, you'll need to build a new one.
Just keep winning, and keep filling the stadium. I believe that the board will be more accepting after having a good season; I've had expansions 3 summers in a row after good seasons; whereas mid-season if I ask the board for an expansion, they won't seem to think I need one.
If your a lower league club, going professional by being promoted to League Two (or alternative professional league) may help.
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