Argentine Diego Schwartzman was 0-9 in his career against Rafael Nadal entering Saturday's quarterfinal clash at the Italian Open in Rome.
Make that 1-9 after World No. 15 Schwartzman beat nine-time Rome champion Nadal 6-2, 7-5.
Schwartzman, who had never previously beaten a top-five player, is off to the last four of an ATP 1000 contest for just the second time after first reaching the mark last year during the same clay-court event at the Foro Italico.
Nadal struggled mightily with his serve, winning just 48% of first-serve points. The Spanish left-hander's record at the Italian Masters 1000 event falls to 63-7 with the defeat to Schwartzman.
Schwartzman will now face Denis Shapovalov after the Canadian topped Grigor Dimitrov 6-2, 3-6, 6-2 for the 100th tour-level win of his bourgeoning career.
Serbia's Novak Djokovic also sealed a spot in the semifinals, beating 97th-ranked German Dominik Koepfer 6-3, 4-6, 6-3.
Two weeks after he was defaulted at the US Open for striking a line judge with a ball, Djokovic smashed his racket on the court after losing a service game to Koepfer.
Djokovic will now play Norway's Casper Ruud, who defeated fourth-seeded Italian Matteo Berrettini 4-6, 6-3, 7-6, (7-5).