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Typically Windows installers do not remove user data. The removal process most familiar to me is that all files registered through the MSI install process are removed by the uninstall process. User data does not usually exist at initial install, so it cannot be registered with the MSI install process.
However, they also do not place user data in the "Program Files" structure. It is more common that "Program Files" is just for the executables, so user data is not there to be removed.
I'm not sure what the Jenkins Windows installer does, though I assume it places some user data in the C:\Program Files\Jenkins directory (based on this bug report).