Hey there! Not a weird question at all. Yes, if both of your two entries place, then you win twice, and both of your games will be published. :-) (Fan Favorite excluded from publication, of course....)
Well, I guess I more so meant 1 entry, if its 2 games well then yeah that makes sense, but could 1 game on its own win both 1st, 2nd, or 3rd as well as fan favorite?