I want to buy an album and a single twice on iTunes but every time I try it says please re-download this from "Already Purchased"... which is clearly what I do NOT want to do.

Can anyone help? Is there anything I can do to trick it?

All you can do is buy another version or use another account.

Gift it to someone else.

you should gift it to someone else, or buy the deluxe/clean edition.

I don't think you can, unless there is another version like a radio edit or you use another account, which could get messy.

Can't gift it because I'm using an iTunes gift card I got... don't want it to charge my debit account. Didn't want to have to go through the hassle of making another account.

Oh well.

Thanks guys

Why do you want to buy it twice?

You purchasing two copies of an album or single is literally not going to have any impact on chart position. So if that's the reason you were wanting to do it, it's just stupidity really.