Goenka, as you might know is a lay teacher, but his teacher, U Ba Khin, and his teacher, Saya Thetgyi (who was taught by the legendary monk Ledi Sayadaw) were also lay teacher so their lay-lineage goes back to the turn of the century and possibly a little before that. In Thetgyi's biography it mentions that prior to meeting Ledi Sayadaw he also learned from lay people, but also that they were rare and didnt command respect as easily as monks. He became very well known though, and through U ba Khin and Goenka that lineage has continued.
I would also imagine that throughout history, so long as there were great meditation masters they conceivably had lay benefactors as students at the very least. http://www.vridhamma.org/Teachers-1