ICloud – Some items missing from the iTunes Purchase History

Google shows various links that say that it is not possible to automatically re-download Audio Books in iTunes.

For example, this recent one - previously purchased audiobooks not showing up - from 3-Nov-2011:

You only get one download of audiobooks and movies. It is your responsibility to backup your purchases.

Similarly:

• Redownload Audio Book PLEASE!!!
• iTunes Audiobook redownload

A few replies, like this one, include extra info:

• How to back up your iTunes purchases (though that Apple page says "This article has been archived and is no longer updated by Apple.")
• How to contact iTunes Support, to request the ability to re-download your purchase

Conclusion

If you have any past back-ups of your desktop machine where you run iTunes and sync(ed) your device, you should be able to restore your purchase.

Otherwise, your best bet is to contact iTunes Store support.

I would advise you to take your question directly to the iTunes Store personnel, they are the ones who keep track of user accounts and purchases made.

You will want to be able to provide them the billing address and payment method you used for those purchases. Also, if you can find any of the invoices that Apple emails between a few hours to a few days after each purchase - you can also let the Apple Store support person you contact that email in case your Apple ID is different than the email on file.