There's something a bit weird in the initial compile:
gcc -c -IC:\strawberry\c\include -s -O2 -DWIN32 -DHAVE_DES_FCRYPT -DPERL_IMPLICIT_CONTEXT -DPERL_IMPLICIT_SYS -fno-strict-aliasing -DPERL_MSVCRT_READFIX -s -O2 -DVERSION=\"0.57\" -DXS_VERSION=\"0.57\" "-IC:\strawberry\perl\lib\CORE" SSLeay.c
... because I don't see a switch like -Ic:\openssl\include but then I don't understand how it manages to compile SSLeay.c without error.
From the CPAN shell you could try doing a look Crypt::SSLeay and then do a classic perl Makefile.PL and dmake, and see if you see a compiler switch that includes the OpenSSL include directory. At which point I would expect saner results.
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