Matteo Arnaldi and Jan-Lennard Struff will play each other in the 1st round of the Boss Open for the 3rd time in their career. They are scheduled to play on Monday at 3:00 pm on CENTER COURT. In the following paragraphs, you can find the head to head analysis and prediction.
Prediction, odds and live streaming
The pick for Tennis Tonic is Matteo Arnaldi who should win in 3 sets.
As per the initial odds, Matteo Arnaldi is the pick to win this match.
Matteo Arnaldi -> 1.63
Jan-Lennard Struff -> 2.28
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Prediction and head to head Matteo Arnaldi vs. Jan-Lennard Struff
This will be the 3rd time that Matteo Arnaldi and Jan-Lennard Struff clash against each other. The head to head is 1-1 for Arnaldi and Struff (see full H2H stats), but they have never competed against each other on grass.
The last time that they squared off, Arnaldi won 6-3 3-6 6-4 in the 2nd round in Shanghai back in 2023.
Matteo Arnaldi
| Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2025 | 15-14 | 6-6 | 7-6 | 2-1 | 0-1 | 0-0 |
| 2024 | 29-26 | 17-13 | 10-9 | 1-2 | 1-2 | 0-0 |
| 2023 | 51-26 | 21-15 | 23-7 | 4-3 | 3-1 | 0-0 |
| 2022 | 50-35 | 9-3 | 37-20 | 4-11 | 0-1 | 0-0 |
| 2021 | 56-24 | 2-1 | 51-18 | 3-5 | 0-0 | 0-0 |
Ranked no. 36, Matteo will start his run in Stuttgart after he played his last match at the Roland Garros where he lost 6-3 6-3 6-7(6) 6-1 to Cobolli in the 2nd round on the 29th of May.
Matteo has an aggregate 15-13 win-loss record in 2025, 0-0 on grass (See FULL STATS).
This will be the first match of the season on grass.
The Italian’s best result of the current year was getting to the semifinal in Delray Beach.
Talking about his overall career, Arnaldi has an overall 231-147 record. He has a flat 4-4 record on grass.
Previously in Stuttgart
The Italian has never competed in this tournament before.
Jan-Lennard Struff
4 - 15win/loss
103
21
WLLLLWLLLL | Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2025 | 5-15 | 1-7 | 1-6 | 2-2 | 1-0 | 0-0 |
| 2024 | 30-21 | 4-8 | 15-5 | 5-6 | 6-2 | 0-0 |
| 2023 | 45-24 | 21-9 | 14-7 | 5-6 | 5-2 | 0-0 |
| 2022 | 23-22 | 3-10 | 7-4 | 12-4 | 1-4 | 0-0 |
| 2021 | 26-30 | 8-11 | 11-8 | 6-8 | 1-3 | 0-0 |
Ranked no. 87, Jan-Lennard will start his run in Stuttgart after he played his last match at the Roland Garros where he lost 7-6(5) 6-3 6-7(5) 6-2 to Ofner in the 1st round on the 26th of May.
Struff has an aggregate 4-15 win-loss record in 2025, 0-0 on grass (See FULL STATS).
This will be the first match of the year on grass.
In terms of his career, Jan-Lennard has an overall 562-425 record. He has a negative 28-33 record on grass.
Previously in Stuttgart
Previously, his best result was reaching the final in 2023. See his history.
Head 2 Head
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WLLLLWLLLL Tennis Scores in Stuttgart
- James DuckworthDuckworth – Nikoloz BasilashviliBasilashvili (6-74 7-65 6-3) – See score progression
- Pierre-Hugues HerbertHerbert – Li TuTu (6-3 6-72 6-1) – See score progression
- Yannick HanfmannHanfmann – Tristan BoyerBoyer (7-612 6-4) – See score progression
- Pierre-Hugues HerbertHerbert – Li TuTu (6-3 6-7(2) 6-1) – See score progression
- Yannick HanfmannHanfmann – Tristan BoyerBoyer (7-6(12) 6-4) – See score progression
- Marton FucsovicsFucsovics – Beibit ZhukayevZhukayev (6-7(5) 6-3 6-2) – See score progression
Upcoming matches in the draw
- Fabio FogniniFognini – Corentin MoutetMoutet (0-0) – H2H and prediction
- Marton FucsovicsFucsovics – Beibit ZhukayevZhukayev (0-0) – H2H and prediction
- Quentin HalysHalys – Lorenzo SonegoSonego (0-1) – H2H and prediction
- Benjamin BonziBonzi – Jiri LeheckaLehecka (1-2) – H2H and prediction
- Roman SafiullinSafiullin – (0-0) – H2H and prediction
- Denis ShapovalovShapovalov – Arthur RinderknechRinderknech (2-1) – H2H and prediction
- Jacob FearnleyFearnley – Brandon NakashimaNakashima (0-0) – H2H and prediction
