What you want to achieve is posible but not with WordPress custom-header feature because it’s you can use multiple images in random sequence.
If you mean ‘different page templates’ you can simply hard code your images links in your templates, but this is not good solution.
Another solution is to write function which will check the name of page template and change header image.
If you need that functionality for normal users you need to create a new settings page for your theme. It should save to WP options information about template name and image for it.