LINQ Orderby Descending Query

You need to choose a Property to sort by and pass it as a lambda expression to OrderByDescending

like:

.OrderByDescending(x => x.Delivery.SubmissionDate);

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Really, though the first version of your LINQ statement should work. Is t.Delivery.SubmissionDate actually populated with valid dates?

I think this first failed because you are ordering value which is null. If Delivery is a foreign key associated table then you should include this table first, example below:

var itemList = from t in ctn.Items.Include(x=>x.Delivery)
                    where !t.Items && t.DeliverySelection
                    orderby t.Delivery.SubmissionDate descending
                    select t;

I think the second one should be

var itemList = (from t in ctn.Items
                where !t.Items && t.DeliverySelection
                select t).OrderByDescending(c => c.Delivery.SubmissionDate);