Can pip.conf specify two index-url at the same time?

If you want more than one package index you have to use the --extra-index-url

From the pip man page:

   -i,--index-url <url>
          Base URL of Python Package Index (default https://pypi.python.org/simple/).

   --extra-index-url <url>
          Extra URLs of package indexes to use in addition to --index-url.

In pip.conf the name of settings must be put without --. From the documentation:

The names of the settings are derived from the long command line option, e.g. if you want to use a different package index (--index-url) and set the HTTP timeout (--default-timeout) to 60 seconds your config file would look like this:

[global]
timeout = 60
index-url = http://download.zope.org/ppix

So you can add in your pip.conf

extra-index-url = http://myserver.com/pip