Do you have fonts-liberation and fonts-wine installed.
If those don't help, what about the non-free ttf-mscorefonts-installer?
There are also some options in Wine (and winetricks) for font hinting,
but I'd need to look into this again.
** Changed in: wine (Ubuntu)
Status: New => Incomplete
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https://bugs.launchpad.net/bugs/1772224
Title:
[regression] jagged fonts in bionic
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