Exporting From Ai To Ancient Cad Program….need Help?

My old employers recently came under new management and are doing away with all the BS that made me quit in the first place. They finally got illustrator, but the Head of Art still uses freaking Corel Draw 9, FML. So they hire me back, and while hes on vacation, I’m doing ALL the artwork that comes in, and I use AI, because its 2012. Four days in, I try to transfer some vectors over to CASmate (which is even older than Corel 9) so I can cut them out in vinyl and transfer to a router… I’m getting error after error. There’s one more thing I can try, but I wanted to get this asked in case it fails. I have saved in legacy formats and all the other obvious stuff, we’ll see.