openssl-fips-2.0.5 seems to build fine for me, here is how you can do it:

1/ download MSYS environment from

2/ unpack standard-msys-20111122.7z into - e.g. c:\dev\msys

3/ make sure you have gcc compiler from strawberry perl in your PATH - e.g. c:\strawberry\c\bin

4/ unpack sources
    openssl-fips-2.0.5.tag.gz into e.g. c:\dev\openssl-fips-2.0.5
    openssl-1.0.1e.tar.gz into c:\dev\openssl-1.0.1e

5/ start c:\dev\msys\msys.bat

6/ in MSYS prompt
    $ cd /c/dev/openssl-fips-2.0.5
    $ ./Configure mingw64 shared --prefix=/c/dev/output
    $ make
    $ make install
    $ cd /c/dev/openssl-1.0.1e
$ ./Configure mingw64 shared fips --with-fipsdir=/c/dev/output --prefix=/c/dev/output
    $ make depend
    $ make
    $ make install_sw

NOTE: for 32bit Windows use "./Configure mingw ..." instead of "./Configure mingw64 ..."

7/ take the results from c:\dev\output

In strawberry perl we do a bit of kung-fu with *.a renaming
    libcrypto.dll.a >> libeay32.a
    libssl.dll.a >> libssleay32.a
    libssl.dll.a >> libssl32.a         (yes, duplicity)
    + we completely drop static libraries libcrypto.a, libssl.a


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