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The world number one, Novak Djokovic, suffered a 6-3 4-6 6-2 exit in the quarter-finals against Russia's Daniil Medvedev at the Monte Carlo Masters.
The 31-year-old, winner of the event in 2013 and 2015, lost to world number 14 in two hours and 20 minutes.
Medvedev will face another Serb in the last four games, the world number 48 Dusan Lajovic.
Defending champion Rafael Nadal, who was looking for his 12th title at Monte Carlo, went from 4 to 1 to defeat World No. 35 Guido Pella 7-6 (7-1) 6-3.
Djokovic, who won a seventh record of the Australian Open in January, lost in the third round at Indian Wells and fourth in Miami last month.
He had beaten Medvedev in the last 16 games en route to his triumph in Melbourne, but had already served five times. The tenth favorite, 23, recorded his first win against the Grand Slam champion fifteen times in their fourth game.
Second-seeded Nadal won four straight games to serve in his first-ever fluctuating set-up with left-handed Pella, but the Argentinian broke again as Nadal conceded five games in a row for the first time in his opening round. 24 last sets in Monte Carlo.
Pella also served for the set at 6-5, but Nadal took advantage of his third opportunity to force a tie-break, which he completely dominated, taking the first six points.
Pella, 28, runner-up in the clay court four times before winning her first ATP title on the same floor at last month's Brazilian Open, was beaten in the opening game of the next match.
He had a total of four break points to equalize at 2-2, but Nadal avoided them and played shots usually very tight, before winning the victory, like Medvedev, in two hours and twenty minutes.
Nadal's opponent in the semi-finals will be Italy's Fabio Fognini, who played with a bandaged right-hand arm and fought to overthrow Borna Coric of Croatia 1-6 6-3 6-2.
The world 's number 18, aged 31, has lost 11 of his 14 games against Nadal, but he is one of seven players to have beaten the Spanish on clay on more than one occasion .
In doubles action, third-seed Jamie Murray of Belgium with partner Bruno Soares qualified for the semi-finals with a 7-5 6-2 win over Diego Schwartzman and Joao Sousa.
Murray and Soares will face the Dutch couple Robin Haase and Wesley Koolhof, who beat the seeded Pierre-Hugues Herbert and Nicolas Mahut in the first round.
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