Ok first, in order to upload any file to your droplet you can user the command scp
scp foobar.txt your_username@remotehost.edu:/some/remote/directory
Here is a related question that shows you how to use scp from Windows.
Then in the console setup in the remote host check if you can run the command python. If you do not have it, just follow the steps in the documentation and you will have python running inside your remote machine.
If you put a Python script on the server and ssh
in, you can run it from the command line. For instance,
python yourFantasticScript.py
If you want a level of automation to triggering the script to run, you will need to learn more about automation scheduling and server technologies.