The question is as simple as the title. I am simply wondering, ‘When is the earliest recorded date of this tradition?’
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According to Gibbons:
It appears that the creeping in of images was long before the schism that brought about the RC and EO traditions -- so though your question apparently concerns post-schism timeline, I hope this answer is relevant.
See also the Catholic Encyclopedia on the Council of Elvira/Elliberis/Illiberis for arguments on dates.
The oldest icon I can imagine would be the one written by St Luke of Our Lady holding the infant Jesus regardless of whether you give any merit to the tradition that it was indeed done by him who was undoubtably the most well aquatinted man in the early Church with the Blessed Virgin Mary, excepting maybe St John the Evangelist, it is certainly an old picture and has been in the keeping of the St Mary Major for a very long time (~1700 years)