In case Calendar Printing Assistant (CPAO) just won't work for you...

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My co-worker posted a how-to on a different way to do printing with a Word template. So if CPAO just won't do what you want, then you might be able to use the Word template as a solution that will work for you...

https://blogs.technet.com/b/sbradley/archive/2010/06/24/the-howto-and-sample-template-for-custom-outlook-calendar-templates.aspx