I think this would require 2 license keys.
Why would you want to do that?
Thanks, @wwatson for a reply.
I have doubt that once I upgrade server version to 2020.2 it will not allow any previous version of alteryx designer on that machine. Because registry issue may occur if try to keep older version with it on the same machine.
Yes, you can have two different versions of Designer installed on a single machine at the same time. However, they do need to differ in version type. One needs to be the admin version and the other the non-admin version.
If you go to install another version, but it is the same type, it will actually uninstall the previous version altogether.