У вас есть SQL Server 2008, поэтому вы можете использовать тип даты
SELECT
orderId,
CONVERT(varchar, orderDate, 101) AS Date_Ordered,
CONVERT(varchar, CAST(sentDate as date), 101) AS Date_Shipped
FROM orders
GROUP BY
orderId, CONVERT(varchar, o.orderDate, 101), CAST(sentDate as date)
ORDER BY
CAST(sentDate as date)
Я не могу точно вспомнить, разрешено ли это, но, надеюсь, вы поняли: если нет, используйте это
SELECT
orderId,
Date_Ordered,
CONVERT(varchar, sentDate2, 101) AS Date_Shipped
FROM
(
SELECT
orderId,
CONVERT(varchar, orderDate, 101) AS Date_Ordered,
CAST(sentDate as date) AS sentDate2
FROM orders o
GROUP BY
orderId, CONVERT(varchar, orderDate, 101), CAST(sentDate as date)
) foo
ORDER BY
sentDate2