I haven't done this with OpenSSL, but I did a similar thing with PCRE. I was able to easily use --dynlibOverride and --PassL / \--PassC to statically link different PCRE versions. I imagine the same process would work for OpenSSL.
Keep in mind that PassL and PassC are just passthrough escape hatches to what ever C compiler you are using, so you would need different flags depending on if you are using msvc or gcc etc...
