I have winecfg set to use the same font as the rest of the operating system (Ubuntu 13.04, Wine 1.5.30, font: "Ubuntu").
When I start Windows programs, the font does sometimes not load and instead a different font is shown (like Arial or even Arial bold, or Ubuntu italic). When I then access a font selector in such a Windows program (ie. SketchUp or Notepad++), the list is incomplete and misses fonts.
inconsistent font loading
Re: inconsistent font loading
Try copying the font(s) to the wineprefix's /windows/Fonts.