https://bugs.winehq.org/show_bug.cgi?id=56165
--- Comment #7 from creatorcray@gmail.com --- (In reply to Rafał Mużyło from comment #5)
Given that one of the fonts you're using in test is bold variant of Arial, could my bug 44963 is strongly related ?
In my case both FW_BOLD and FW_NORMAL variants were affected. Also I traced down the issue to the freetype library calls, and it turned out that Crossover switched from good version of FreeType 2.6.2 to a clearly buggy version 2.12.1, from what I see inside the dylib files.