Depending on whether you are using the base Windows Server 2008 or the updated 2008 R2 version, the supported Python releases differ: Python Releases for Windows
Download Python for Windows Server 2008 To download and install Python on Windows Server 2008 or 2008 R2, you must select a version compatible with these older operating systems. Modern Python versions (3.9 and newer) do not support Windows Server 2008, as they require updated system components like the Universal C Runtime (UCRT). Recommended Python Versions for Windows Server 2008 download python for windows server 2008