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Excellent! Upon further digging, I found out that a chess grandmaster, one Savielly Tartakower, was defeated by El Ajedrecista [1], a machine that could play chess endgames. This was 1951, so before the Los Alamos lab assistant, but a bit after the defeat of customers by Bertie the Brain.

The Ajedrecista had been around since 1912, so I would expect somebody must have been defeated by it in the years before 1951.

[1]. https://www.chessprogramming.org/El_Ajedrecista

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