Updating OpenSSL in OSX
OpenSSL 0.9.8zg 14 July 2015 is the version installed by OS X 10.9(.5) (Mavericks) and resides in /usr/bin/.

MacPorts neither installs nor updates/upgrades genuine Apple (OK, OpenSSL is not Apple but it's part of their basic BSD package) system software. MacPorts' standard realm is /opt/...

You would have to install a newer OpenSSL version with MacPorts - if available.