It seems in Windows Server latest versions the good old disk clean up tool is not enabled by default. If you just want it back you can run the below commands in a command prompt to copy the required files.

Copy C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr_31bf3856ad364e35_6.1.7600.16385_none_c9392808773cd7da\cleanmgr.exe C:\Windows\System32\

Copy C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr.resources_31bf3856ad364e35_6.1.7600.16385_en-us_b9cb6194b257cc63\cleanmgr.exe.mui C:\Windows\System32\en-US\

Then create a shortcut pointing to the Disk Clean up tool found in the following path.

C:\Windows\System32\CleanMgr.exe

I did try this on Windows Server 2008 R2 and hope it works as it is or with slight changes on other versions of Windows as well.

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