Fairly simple to do w/o involving the Calendar, esp. if it's repeated on a regular basis.
All Unix systems (ala OSX in this case) use 'cron' to allow you to schedule events on regular basis. For you GUI lovers, you can use Cronnix
which is a frontend to the cron system.
The OSX printing subsystem can print out images via command line ala something like........
lp -P epson3880 some_image_to_keep_your_heads_unclogged.jpg
So, all you do put the correct 'lp' command into cron and you're all set.
That just saved you from buying Harvey HeadCleaner
When you say from Calendar, are you referring to something connected to OS X calendar? Are you scheduling a calendar event to trigger a print job? Sounds useful ...