After many attempts, I’ve successfully installed the Windows 32-bit version of iTunes 12.6.5.3 using Wine in Mojave.
Steps:
1. Install XQuartz - XQuartz-2.7.11.dmg from
https://www.xquartz.org
2. Install Wine Stable 5 winehq-stable-5.0.pkg from
https://dl.winehq.org/wine-builds/macosx/download.html
3. Download Mono wine-mono-5.1.0-x86.msi from
https://dl.winehq.org/wine/wine-mono/5.1.0/
and Gecko wine-gecko-2.47.1-x86.msi from
https://wiki.winehq.org/Gecko
4. Launch /Applications/Wine Stable.app
5. In the Terminal window opened, install Mono & Gecko with
wine msiexec /i ~/Downloads/wine-gecko-2.47.1-x86.msi
wine msiexec /i ~/Downloads/wine-mono-5.1.0-x86.msi
6. Install iTunes 12.6.5.3 32-bit version for Windows from
https://support.apple.com/en-us/HT208079 with
wine ~/Downloads/iTunesSetup.exe
7. Start iTunes with
wine ~/.wine/drive_c/Program\ Files/iTunes/iTunes.exe
Enjoy iTunes with a functional App Store on macOS Mojave!
Notes: There is no confirmation on the successful installation of Mono & Gecko. After pressing Finish in the iTunesSetup.exe installation, enter ctrl+C in Terminal to stop it.
If wine crashes, use killall wineserver and killall wine-preloader, then launch again /Applications/Wine Stable.app
If you prefer Homebrew, XQuartz can be installed with
brew cask install xquartz and Wine with
brew cask install wine-stable.
I had no success with PlayOnMac on Mojave or Catalina. CrossOver 19.0.2 can be used in Catalina and probably Mojave too.
https://forums.macrumors.com/threads/itunes-12-6-5-3-on-macos-catalina-10-15.2184518/post-28569328