The Date Added field is not sent to iTunes. In Bookshelf view, books are shown in the order they were added to the iDevice. By controlling the order the books are sent to the iDevice, you can control the order they are displayed in iBooks. If you have a group of books to send, sort them by date added to calibre, oldest at the top. Group select, then send. The last book in the group will be the most recent addition in the bookshelf view.
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