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I had a similar problem with one league. Found out that it was actually a firmware issue with my router/modem that was not allowing me to make correct FTP connections, the connection type that OOTP uses for downloading the updated league files in game.
I also had it (updating) working fine on one league and not another, but the firmware update fixed everything.
What you have described is very similar to me, it worked perfectly one day and then didn't next on this one league with no changing of anything by me.
Not saying a firmware update will fix it, but it's worth a try - maybe even do a google search to see if anyone else has had general ftp issues with your modem/router, that's how I discovered this fix for me.
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