Omega can do that, although I think you would be best off leaving the image out at the time you create the sequential numbering.
If you create a vector contour that matches the outside parameters of your image, possibly the cut line even, you will be able to make quick work of the numbering process in Omega, by designating the size, font, and placement, as well as start number & the increments to increase each item by. You should also set the overall nesting plan of 10 rows of 10, with 1/4" between or whatever... & Omega can generate the resulting layout. This layout can then be exported as an .eps or .ai file & merged with your image in another program, prior to printing.
Omega could do this with the image file included, but the increased file size may slow it down, and the export capability may not be as seamless, although that's just a guess.