Left Join without duplicate rows from left table

Try an OUTER APPLY

SELECT 
    C.Content_ID,
    C.Content_Title,
    C.Content_DatePublished,
    M.Media_Id
FROM 
    tbl_Contents C
    OUTER APPLY
    (
        SELECT TOP 1 *
        FROM tbl_Media M 
        WHERE M.Content_Id = C.Content_Id 
    ) m
ORDER BY 
    C.Content_DatePublished ASC

Alternatively, you could GROUP BY the results

SELECT 
    C.Content_ID,
    C.Content_Title,
    C.Content_DatePublished,
    M.Media_Id
FROM 
    tbl_Contents C
    LEFT OUTER JOIN tbl_Media M ON M.Content_Id = C.Content_Id 
GROUP BY
    C.Content_ID,
    C.Content_Title,
    C.Content_DatePublished,
    M.Media_Id
ORDER BY
    C.Content_DatePublished ASC

The OUTER APPLY selects a single row (or none) that matches each row from the left table.

The GROUP BY performs the entire join, but then collapses the final result rows on the provided columns.

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