Yes, Kenichi is right. So to print from an OS 9-based application, whether in Classic mode or booted in pure OS 9, you must have an OS 9 driver installed for the printer you intend to use.
A somewhat clumsy workaround, for printers that have no OS 9 drivers, is to download, install and select
PrintToPDF as your OS 9 printer driver, then open the resulting PDF file in the OS X-native Preview or Adobe Reader and print it using your printer's OS X driver.