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The Status report shows the supervisor associated with the user's profile when the timesheet was generated.
If a Supervisor name does not show in the Supervisor column of the report, then there was no Supervisor associated with that user when that timesheet was generated.

If a timesheet is generated before a Supervisor is added to the users profile and later a Supervisor is added with effective date earlier than the date of timesheet generation,  the timesheet would still not be associated to the supervisor.