It's not logged into the users history when they have won, but I have received the PM when I won the lottery. To test it, I made sure I was the only one who purchased a ticket, and then set the lottery end time to yesterday and ran the cron job to process the lottery and I won the lottery and received a PM for it. So if its not working on ur end, its something different u have in ur setup that is causing an issue and I'd need admin access with can administer plugins, settings & scheduled tasks to take a look at it further.
-CMX
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