I don't know who put these in order, but they should be in line with thetvdb's ordering system, which is the one most services use.
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@tvdown Agreed, it's definitely making ordering on Plex a challenge. And now it appears officially they're considering these specials and season 14 as season 1 of a new show so that Disney+ isn't just randomly missing the first 13 seasons.
We definitely need a consistent method across the internet for these specials.