Assuming that was what you want - i can't get it to work. I figured 4 copies (set in outlook) and 4 up (printer options) and all i ended up with was 12 pages of scrap paper. <g> (I tried different paper sizes too.)
My only other thought is a two step process - print 4 copies to a pdf or other electronic format then print that to the printer using 4-up layout. I haven't tried it with the calendar yet, but it should work.
Dang... now i realize the error in my thinking. Outlook is not sending 4 calendars to the printer but printing 1 calendar 4 times. That's why that plan failed.
You'll need to print to electronic format then copy the electronic format 3 times - then merge them into one and print them 4 up. Merging the 4 copies into 1 - 4 page file may not be necessary - i didn't test just printing 4 separate documents.