Kei Nishikori had no answer for some magical shot making by world No. 49 Pierre Hugues Herbert, who won their second-round match at the Monte Carlo Masters on Tuesday.
Nishikori, ranked sixth in the world and seeded fifth at the clay-court event, lost 7-5, 6-4 to the Frenchman, who he had played twice in his career on hardcourts and won both times.
In the fifth game, Nishikori squandered four break points in a seven-minute, 44-second game as Herbert held serve to take a 3-2 lead. Nishikori then had to fight to hold serve. The Frenchman pulled another rabbit out of his hat with some amazing shots to hold serve in an eight-minute ninth game.
Herbert continued his magic act to hold serve in the 11th game, barely getting to what looked like a winner from Nishikori and firing back an off-balance winner past Nishikori at the net. He then took the match's first service break and held serve to take the set.
The second set was a virtual repeat, with no service breaks until Nishikori failed to hold serve in the 10th and final game.