There are available some experimental OpenSSL v0.9.8y (2013/02/06) and v1.0.0k (2013/02/07) for download.
"OpenSSL is an open-source implementation of the SSL and TLS protocols."
Download
0.9.8y OS2-EMX (for genuine EMX) : openssl-0.9.8y-os2emx-20130206.zip
0.9.8y OS2-KNIX runtime EXE/DLLs (for kLIBC 0.6.3 or later) : openssl-0.9.8y-os2knix-20130206-runtime.zip
0.9.8y OS2-KNIX development headers/libs (for kLIBC 0.6.3 or later) : openssl-0.9.8y-os2knix-20130206-dev.zip
1.0.0k OS2-EMX (for genuine EMX) : openssl-1.0.0k-os2emx-20130207.zip
1.0.0k OS2-KNIX runtime : openssl-1.0.0k-os2knix-20130207-runtime.zip
1.0.0k OS2-KNIX development headers/libs : openssl-1.0.0k-os2knix-20130207-dev.zip
URL: http://bauxite.sakura.ne.jp/software/os2/#openssl
Source: OS2.jp