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If we've settled on '99-'00 as the beginning of real digisubbing, my digisubs of Hunter X Hunter are the oldest surviving files in my collection. HxH debuted in October of '99, and the subs are from aku-fansubs.
Generally, though, I remember digisub trading being pretty active before that. For instance, I know I saw Tenshi ni Narumon (April '99), The Adventures of the Mini-Godesses (April '98), and Record of Lodoss War TV (April '98) through a purely digital release.
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