https://bugs.winehq.org/show_bug.cgi?id=38060
--- Comment #13 from Sam masterofquebec@rocksplash.com --- Looks like error 2 is Unknown File Format (fterrdef.h).
It seems that FT_Open_Face can't find a driver for the file. This is strange as Freetype has no problem loading the same font during init_font_list().
WineEngAddFontResourceEx->AddFontToList->new_ft_face->FT_New_Face->FT_Open_Face