We have a specific need for OpenSSL 0.9.8za, and cannot rely on back-ported support for these features in newer versions of OpenSSL (1.0.1).
After installing checkinstall (sudo apt-get install checkinstall), here's the commands I've run:
sudo apt-get remove openssl libssl-dev
wget http://www.openssl.org/source/openssl-0.9.8za.tar.gz
tar -xzf openssl-0.9.8za.tar.gz
cd openssl-0.9.8za.tar.gz
./config --prefix=/usr
sudo make
sudo checkinstall
At this point, OpenSSL tries to install, and gets hung up with this output:

Is there a way we can fix this to compile and install correctly on Ubuntu 14.04?