https://bugs.winehq.org/show_bug.cgi?id=39913
--- Comment #19 from curaga@operamail.com ---
That version is 8 years old, and could be the reason why none of us can reproduce the problem. You might want to try upgrading Freetype.
This machine is dedicated to this one game. If I could only find a Wine version where everything works, I'd freeze it altogether. So far every Wine version has some bug or other.
That said, I can try it later, but I doubt it'd fix Wine's font selection problem, it might only fix the rendering issue.
Could you try to install MS core fonts
Sure. Installing the MS fonts made Wine use them, but the app is still broken. I'm attaching both a screenshot and the new font debug log.