https://bugs.winehq.org/show_bug.cgi?id=47872
--- Comment #4 from Vincent Povirk madewokherd@gmail.com --- Part of this is really testing gdi32 behavior. Sometimes DEFAULT_GUI_FONT is a different face than MS Shell Dlg. That doesn't really belong in the gdiplus tests. It looks to me like test_stock_fonts in gdi32:font covers this.
The rest may just be a side-effect of not passing MS Shell Dlg into gdiplus functions.