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For the first time in eight appearances, Stefanos Tsitsipas has lost his opening match at the Rolex Monte-Carlo Masters.

In a difficult first-round matchup full of clay-court pedigree, 16th seed Francisco Cerundolo locked up a 7-5, 6-4 victory. The Argentine recovered from letting a double-break lead slip in the second set to notch his first win in three meetings, with their previous two coming in back-to-back weeks during the closing 2024 indoor hard-court swing.

Both had knocked off Top 10 opponents during their most recent event at the Miami Open, with Cerundulo taking out Daniil Medvedev and Tsitsipas eliminating Alex de Minaur. But outside of that connection, the two have headed in different directions so far in 2026.

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Francisco Cerundolo eliminates three-time champ Stefanos Tsitsipas | Monte Carlo Highlights

Cerundolo captured his fourth career title in February, triumphing in his birth city of Buenos Aires. He is 15-6 on the year, having reached the round of 16 at the Australian Open—and has a chance to improve upon his career-high ranking of No. 18 this week.

As for the 48th-ranked Tsitsipas, after briefly dropping out of the Top 50 for two weeks following the BNP Paribas Open, he will exit the Top 60 with this latest defeat. The last time he found himself that low on the rankings was the week of April 23, 2018 when he stood at No. 63.

The Greek had won 22 of 26 matches at the Monte-Carlo Country Club coming in, but has struggled since opening the season by clinching all three of his singles matches at the United Cup. Tsitsipas has since gone 6-8 in tour-level tournaments (he won both matches for his nation in Davis Cup against opponents ranked No. 222 and 818, respectively) with one quarterfinal showing in Doha.

In the second round, Cerundolo awaits Tomas Machac.