Hi,
Assuming ssleay32.lib is located in one of the directories specified in %LIB% (and assuming it can resolve the missing symbols), your only problem is that the Crypt::OpenSSL::Random Makefile.PL does not look for an import library named ssleay32.lib.
Alternatively to the approach already suggested by
Anonymous Monk, creating a copy of ssleay32.lib named ssl.lib (in any of the folders specified in %LIB%) should fix that.
Or, in the Makefile.PL you could replace both occurrences of
-lssl -lcrypto with
-lssleay32 -lssl -lcrypto
Cheers,
Rob