Yes it can be done, but without knowing which trivia script you're using (there are several out there) or if you're using one of your own, I can't tell you how to edit the code.
I'll need the section of the script where it adds to the channel list, so that I can determine how it knows the difference between someone that has won 50 times vs. 100 times.
I'll also need to know if there's an ON JOIN event in the code already.
There might be other information that I'll need, but that's the minimum that I can think of at the moment.
