I don't know what OS you're using, I'm using a Mac so hopefully this works for you.
If you are trying to update your pip to 6.1.1 you have to upgrade Python 2.7.9 because the certification is bundled together. You can see this in the README documentation for Python 2.7.9: "The bundled pip included with 2.7.9 has its own default certificate store for verifying download connections"
It also says that the 0.9.7 version of the OpenSSL library is out of date, so if you download a new version of python you have to make sure the version of OpenSSL it is linked to is up to date. Right now it should be the 10.5+ 32-bit variant and it is linked with a private copy of OpenSSL 1.0.1
After you've downloaded that try installing pip. I had permission issues so I had to use sudo to install using: sudo pip install --upgrade pip
If that doesn't work you can try upgrading your setup tools:
pip install --upgrade --no-use-wheel setuptools
or
pip install --upgrade setuptools
Then you will need to upgrade Python: pip install --upgrade python
If you need help with pip commands use: pip2.7 --help
After that you can double check to make sure the correct versions are installed using: pip --version and python --version.
I hope that helps!
