The earliest ones I could find... These were made when I was an intern for the City of Nijmegen, back in early 1998. Only have these paper copies, so you'll have to do with crappy cellphone pics for now.
(The general route map to the various city offices downtown, technically this is the first map I ever produced that was meant for the general audience)
I initially had to work with Microstation there, and then run the DGN files through something called "CadScript" (if I recall correctly), assigning styles to various levels and outputting an EPS file. I quickly convinced them to let me use Illustrator and MAPublisher (on account of having used that combination at my previous internship). There were loads of problems with the printer's, mainly fonts. The printer's office was on the other side of town, which was either a 20 minute bike ride or a 5 minute train ride followed by a 30 minute walk... When we finally sorted out all the problems I was confident it was going to be a great map. Next morning I come in the office and see a stack of the printed maps on my desk, so I look at it very proudly, turn it over to study the back (overview map of the municipality) and notice one layer appears to have been shifted. So I call the printer's and utter the famous words "stop the presses", to which they reply "yeah, we're done already...". I suspect it happened because they opened the Illy file and played around with it... I know for sure my file was good.
(A derived map for another organisation, the first map I ever produced for an "outside" client)
I had made maps before at a previous internship and in school of course, but those were either for internal use or for assignments.