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OK, first off bear in mind I'm using the PC version of FileZilla, so I'm not 100% sure it's identical. But try this:
First, zip up all of those .dat files from your OOTP 9 league, and give them a name that makes sense like "koolkerns.zip". Then:
1. Open FileZilla and go to File | Site Manager
2. Click New Site
3. In the Host box, type ootpsupport.com.
4. Click on the Advanced tab, and in the Default Remote Directory field, type incoming/ootp/saved_games/.
5. Click Connect. It should connect to our server.
6. The right side of the screen is our server, the left is your computer. On the left, navigate to find your zipped up .dat files.
7. Drag them from the left to the right, and watch the transfer status. When it's done, post back here and let us know it's done!
I hope this works! If it doesn't seem to match up, let me know, and I'll grab the mac version on my Mac so I can be sure I'm looking at the same thing!
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