Aug 14, 2024; Cincinnati, OH, USA; Stefanos Tsitsipas of Greece reacts during a match against Jan-Lennard Struff of Germany on day three of the Cincinnati Open.

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Stefanos Tsitsipas vs. Jan-Lennard Struff Head to Head Record, Preview and Prediction for ATP Madrid Open 2025 Round of 64

World No. 18 vs World No. 79 at the Spanish capital.

Aug 14, 2024; Cincinnati, OH, USA; Stefanos Tsitsipas of Greece reacts during a match against Jan-Lennard Struff of Germany on day three of the Cincinnati Open.

Weeks after relinquishing his title in Monte Carlo, Stefanos Tsitsipas looks to set the record straight at the 2025 Mutua Madrid Open. Having received a bye in Round-1, the Greek freak opens his account against Jan-Lennard Struff of Germany on Saturday. Tsitsipas is a former runner-up at the Spanish capital, but hasn’t managed to get his hands on the trophy just yet.

At the 2019 Madrid Open, Stefanos Tsitsipas had one of the most potent tournaments of his career. However, he fell short at the final hurdle vs Novak Djokovic. Currently ranked No. 18 in the world, the two-time Grand Slam finalist witnessed a huge drop after giving up crucial points in 2025. With a career-high ranking of No. 3 in the world, this is arguably the 26-year-old’s best surface. He has a 16-7 record on clay over the past 12 months and won over 83% service games.

For anyone who thinks Tsitsipas has an easy route to Round-3, Jan-Lennard Struff would beg to differ. The German’s solitary title win came on clay, at the Munich Open in 2024. Struff is a strong baseliner who relies heavily on his serve and forehand. He has gone 9-7 on clay over the past year, with over 81% wins on serve. Struff was leading 7-5 2-6 4-1 in his opening round vs Van de Zandschulp, before the Dutchman retired.

Stefanos Tsitsipas vs Jan-Lennard Struff Head to Head Record

Stefanos Tsitsipas has a head to head record of 5-4 vs Jan-Lennard Struff. It is a closely contested duel since its inception.

Tsitsipas and Struff faced off thrice each in 2019 and 2024, twice in 2020 and once in 2023. Three out of these nine meetings have been on outdoor clay courts – similar to Saturday’s fixture. Interestingly, the Greek starlet has won the first as well as last encounter against his counterpart.

Event	Round	Winner	Score
2024 Cincinnati	Round of 64	Stefanos Tsitsipas	4-6 6-4 6-3
2024 Halle	Round of 16	Jan-Lennard Struff	6-4 6-4
2024 Rome	Round of 64	Stefanos Tsitsipas	6-7(1) 6-4 6-4
2023 Madrid	Quarterfinal	Jan-Lennard Struff	7-6(5) 5-7 6-3
2020 Vienna	Round of 32	Stefanos Tsitsipas	6-7(3) 6-3 6-4
2020 Dubai	Quarterfinal	Stefanos Tsitsipas	4-6 6-4 6-4
2019 Cincinnati	Round of 32	Jan-Lennard Struff	6-4 6-7(5) 7-6(6)
2019 Barcelona	Round of 16	Jan-Lennard Struff	6-4 3-6 6-2
2019 Sofia	Round of 16	Stefanos Tsitsipas	7-6(5) 6-4

Stefanos Tsitsipas vs Jan-Lennard Struff Titles Comparison

Stefanos Tsitsipas	Category	Jan-Lennard Struff
0	Grand Slams	0
12	ATP Singles Titles	1
2	ATP Doubles Titles	0
3	Masters-1000 Titles	0
1	ATP-500 Titles	0
QF (Paris 2024)	Olympics Best Performance	R2 (Tokyo 2020, Paris 2024)
No. 18	Current World Ranking	No. 79

Stefanos Tsitsipas vs Jan-Lennard Struff Madrid Open 2025 Prediction

Paula Badosa and Stefanos Tsitsipas at the Laureus World Sports Awards in Madrid.

🤍 pic.twitter.com/kTazbUxiFI
— The Tennis Letter (@TheTennisLetter) April 21, 2025

At last week’s Barcelona Open Banc Sabadell, Stefanos Tsitsipas retired due to a physical condition. A lot will depend on his fitness on Saturday, as Struff can be a steely opponent. Nonetheless, he has the game to neutralise the big serve of the 35-year-old and take charge from there. With Carlos Alcaraz pulling out and Djokovic not in the best of form, Tsitsipas will fancy his chances of capturing the championship at La Caja Magica.

Prediction: Stefanos Tsitsipas in straight sets.

Stefanos Tsitsipas vs Jan-Lennard Struff Madrid Open 2025 Betting Odds

Stefanos Tsitsipas Win: 2/7

Jan-Lennard Struff Win: 11/4

ATP

ATP Masters 1000

Betting

Carlos Alcaraz

Jan-Lennard Struff

Madrid Open

Novak Djokovic

Roland Garros

Stefanos Tsitsipas

Tennis

Sankalp Harikrishnan

A passionate sports fan through and through, I am currently pursuing my MA in Global Sports Journalism. I specialise in tennis and football writing at The Playoffs News, and I have prior experience working at EssentiallySports and Sportskeeda. Born and raised in Bengaluru, India, sport was my safe space right from my childhood. After trying my hand at multiple sports and representing my educational institutions in cricket, badminton and table tennis, I found sports media to be my calling.