Although it was not technically the same award, I have included the win for Best All-Time Series awarded in 1966 in this list on the grounds that this was the spiritual ancestor of the current version of the award. That award was won by Asimov's Foundation series, which beat out some pretty stiff competition - which was made more difficult than normal for a Hugo by what appear to have been some extremely open-ended rules for what would qualify as a finalist. In any event, I've listed it here because I think it should be, even if the official records don't agree with me.
1945: The Cthulhu Mythos by H.P. Lovecraft, August Derleth, and others (awarded in 2020)
1966: Foundation series by Isaac Asimov (first novel in series: Foundation)
2017: The Vorkosigan Saga by Lois McMaster Bujold
2018: World of the Five Gods by Lois McMaster Bujold
2019: Wayfarers by Becky ChambersWhat Are the Hugo Awards?
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