CSS Clear Floating Point Columns?

I am floating the sidebar to the left of the main content pane. Then inside this panel I have several boxes that float and clear to create a kind of grid (this is the “my account” page with various blocks containing things like orders, editing details, etc.). The problem is that the boxes inside the contents of the div are cleared from the sidebar, and not just from the other boxes in this div. There's a link to the image below if this explanation is confusing:

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Has anyone encountered this before, and if so, do you know how to fix it? I’m probably mistaken, but I almost completely learned CSS from trial and error, so I know about his theory, most likely not enough.

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