Wine on Leopard OS X 10.5 via MacPorts is broken 3
The wine port (MacPorts) for version 0.9.49 for Leopard is broken and fails with a
./crtdll.spec:44: external symbol 'CRTDLL__basemajor_dll' is not a function
There is a bug in their Trac about it, if you have an account.

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Hey, I have the exact same problem, did you find a fix?
For now I am just using a newer Darwine build I found. In the future I might use Mike Kronenberg’s Darwine build, since he is now maintaining a graphical installer OS X version of ies4linux, which is the only reason I was installing wine. It even grabs the fonts for you. Not sure if it installs freetype and fontforge, since I already had those.
FYI, you don’t need an account to just view the ticket, though you do to modify it. Also, it will help me to solve the problem if discussion about the problem occurs there, or on macports-users.
There is no port for ies4osx / ies4mac / ies4linux yet but I want there to be one.