calibre builds its own cover when one isn't specified. If you specify one, you'll have to specify one that has your date. I can think of two approaches I'd explore. One would be to look at the custom cover plugin and the calibre default cover code and see if it could be adapted to do what you want. You can do most anything with the Python code in a recipe if you are skilled.
The other option would be to see if the Image Magick code that calibre uses has some way of adding text to an image. I've used Image Magick in calibre recipes to rotate images, resize images, change them to black and white, etc. It's possible there's code in there to add overlay text of some sort.
I have no idea if either would work for you.
Good luck!
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