Tillman wins since Wilson was also a white supremacist and he managed to win in a massive landslide due to the split GOP vote. Also, Tillman had some Progressive positions on the issues, and thus I think he would do about as well as (or a little worse than) Wilson did with both Progressives and conservatives. I will make a map later.
Wilson was not nearly as vocal in his beliefs as Tillman. I don't know if I'd go as far as calling Wilson a white supremacist; he was certainly a racist, but white supremacy is a whole different subject.
Anyways, in a perfect world, Roosevelt wins. I'd say he wins either way...Map:
