It used to be that doing this and then clicking the green update history button would update for up to 500 games back.
http://dotabuff.com/pages/faq
^^^^^^^^^^^^^^
here
I don't know if it still works since the "first blood" patch. Please try it and let us know if things are working correctly.
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I just left it as is when it was first introduced but now I want to enable it again on my old account. If I turn this setting on now, will dotabuff get all the matches that have been played on the account since 9 months ago?