The default value is set to show 10 documents, but you might increase that with a registry tweak.

For instance, if you want to set it to 50, enter that into the Value data field.

Now I’m not entirely sure what will happen if you set it to a huge number…

Change the Number of Recent Items Shown on the Windows 7 / Vista Start Menu

I’d stick with something like 20.

Note that the same tweak works in Windows 7 as well, even though the screenshots are from Vista.

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Windows