I did it successfully on Fedora 22. I installed mingw32 and a mingw32 package for all the dependencies except webp (even leptonica was precompiled). Then I compiled and installed webp and finally compiled tesseract. To compile each, make a build folder like: .../webp/build_win32 then run mingw32_configure. Then make and make install (for the library). Mingw32_configure looks for configure in the parent directory, sets up a special environment and then executes it (you execute autogen.sh first to create configure). I then copied API/tesseract to my windows machine and tried to run it. It would then complain about each DLL it needed. Back on the Linux machine I would dig out the DLL from the mingw32 root somewhere in /usr/ and copy it to the Windows machine. Once it gave a general error but it was still a missing DLL (libz I think). Once all the DLLs are there it works great.
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