Export Outlook Emails (Mac) to Gmail
It depends on the setup you already have, but I think this should work.


In your mail client (Entourage/ Outlook) setup the IMAP access to your Gmail account.
Setup the folders for sent and trash.
Move all mails from your other inboxes to your Gmail inbox:
Select all folders by clicking the top one under the account to be moved, and then Shift-click the bottom one. After all the folders are selected, drag and then drop them onto your Gmail account in the sidebar. (If there are many folders you may want to consider testing a couple first, before moving all of them).


If the account is large, it will take awhile to upload all the email.