For the most part you're goign to have to to lose a few of your matches to go into different routes. To do this you're going to have to figgure out which fight part you can win or lose on.
I think someone posted up ther enitre route for each of the
storylines. The #8 comes after you finally done the 1st route, and that is really the introduction of one character that never actually showed up in the Tsukihime game series at all, but was mentioned of course.