PREDICTION, PREVIEW, H2H: Sinner, Djokovic, Shelton and Cilic to play on Monday – Wimbledon

ORDER OF PLAY and PREVIEW. Jannik Sinner, Novak Djokovic, Ben Shelton and Marin Cilic are going to compete on Monday in Wimbledon.

[SEE DRAW and ORDER OF PLAY]

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Jannik Sinner vs. Grigor Dimitrov

Head to head 4-1 for Sinner

Jannik Sinner will play Grigor Dimitrov in the 4^th round for the 6^th time of their career. They are scheduled to compete on Monday at 6:30 pm on Centre Court.

Jannik Sinner: ranking and results

Currently world no. 1 the Italian got to the 4^th round after beating Luca Nardi 6-4 6-3 6-0, Aleksandar Vukic 6-1 6-1 6-3 and Pedro Martinez Portero 6-1 6-3 6-1.

The Italian has a 22-3 win-loss record in 2025, 4-1 on grass (See FULL STATS). His best result of the season was winning the title at the Australian Open where he defeated Alexander Zverev in the final 6-3 7-6(4) 6-3.

Last year at Wimbledon The Italian lost in the quarter 6-7(7) 6-4 7-6(4) 2-6 6-3 to Daniil Medvedev.

Grigor Dimitrov: ranking and results

Ranked no. 21, Grigor reached the 4^th round after defeating Yoshihito Nishioka 6-2 6-3 6-4, Corentin Moutet 7-5 4-6 7-5 7-5 and Sebastian Ofner 6-3 6-4 7-6(0).

Grigor has a 17-10 win-loss record in 2025, 3-0 on grass (See FULL STATS). The Bulgarian’s best result of the season was reaching the semifinal in Brisbane and Miami.

Last year at Wimbledon Grigor got to the 4^th round last year in Wimbledon before retiring against Daniil Medvedev.

Head to head analysis

This will be the 6^th time that Jannik Sinner and Grigor Dimitrov play each other. Their current head to head is 4-1 for Sinner (see full H2H stats), but they have never played each other on grass.

Before, the last time they played each other, Sinner won 6-2 6-4 7-6(3) in the quarter in Roland garros back in 2024.

Prediction, odds and live streaming

The pick for Tennis Tonic is Jannik Sinner who should win in 3 sets.

(image) As per the initial odds, Jannik Sinner is the pick to win this match.
Jannik Sinner -> 1.07
Grigor Dimitrov -> 8.4

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Novak Djokovic vs. Alex De Minaur

Head to head 2-1 for Djokovic

Novak Djokovic will play Alex De Minaur in the 4^th round for the 4^th time of their career. They are scheduled to play on Monday at 1:30 pm on Centre Court.

Novak Djokovic: ranking and results

Ranked no. 6, Novak got to the 4^th round after defeating Alexandre Muller 6-1 6-7(7) 6-2 6-2, Daniel Evans 6-3 6-2 6-0 and Miomir Kecmanovic 6-3 6-0 6-4.

Djokovic has a 24-8 win-loss record in 2025, 3-0 on grass (See FULL STATS). His best result of the current season was conquering the title in Geneva where he beat Hubert Hurkacz in the final 5-7 7-6(2) 7-6(2).

Last year at Wimbledon The Serbian lost in the final 6-2 6-2 7-6(4) to Carlos Alcaraz. Djokovic conquered the title in Wimbledon in 2011 and 2018.

Alex De Minaur: ranking and results

Ranked no. 11, Alex reached the 4^th round after defeating Roberto Carballes Baena 6-2 6-2 7-6(2), Arthur Cazaux 4-6 6-2 6-4 6-0 and August Holmgren 6-4 7-6(5) 6-3.

Alex has a 30-12 win-loss record in 2025, 3-1 on grass (See FULL STATS). Alex’s best result of the current year was reaching the final in Rotterdam.

Last year at Wimbledon The Australian capitulated in the quarter w/o to Novak Djokovic.

Head to head analysis

This will be the 4^th time that Novak Djokovic and Alex De Minaur square off. The head to head is 2-1 for Djokovic (see full H2H stats), but they have never played each other on grass.

Before, the last time they squared off, Djokovic won 7-5 6-4 in the quarter in Monte carlo back in 2024.

Prediction, odds and live streaming

The pick for Tennis Tonic is Novak Djokovic who should win in 4 sets.

(image) As per the initial odds, Novak Djokovic is the pick to win this match.
Novak Djokovic -> 1.28
Alex De Minaur -> 3.68

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Ben Shelton vs. Lorenzo Sonego

Head to head 3-1 for Shelton

Ben Shelton will take on Lorenzo Sonego in the 4^th round for the 5^th time of their career. They are scheduled to compete on Monday at 3:00 pm on Court 1.

Ben Shelton: ranking and results

Ranked no. 10 (career high), Shelton got to the 4^th round after beating Alex Bolt 6-4 7-6(1) 7-6, Rinky Hijikata 6-2 7-5 6-4 and Marton Fucsovics 6-3 7-6(4) 6-2.

The American has a 22-14 win-loss record in 2025, 5-3 on grass (See FULL STATS). Ben’s best result of the current season was getting to the final in Munich.

Last year at Wimbledon The American lost in the 4^th round 6-2 6-4 7-6(9) to Jannik Sinner.

Lorenzo Sonego: ranking and results

Ranked no. 47, the Italian reached the 4^th round after beating Jaime Faria 6-3 6-4 6-2, Nikoloz Basilashvili 6-1 6-3 6-7(3) 7-6 and Brandon Nakashima 6-7(5) 7-6(8) 7-6(2) 3-6 7-6(3).

Lorenzo has a 14-16 win-loss record in 2025, 5-3 on grass (See FULL STATS).

Last year at Wimbledon The Italian lost in the 2^nd round 6-3 3-6 6-3 6-4 to Roberto Bautista Agut.

Head to head analysis

This will be the 5^th time that Ben Shelton and Lorenzo Sonego play each other. Their current record is 3-1 for Shelton (see full H2H stats), but they have never competed against each other on grass.

The last time they played, Shelton won 6-4 4-6 3-6 6-2 6-3 in the 1^st round in Roland garros back in May 2025.

Prediction, odds and live streaming

The pick for Tennis Tonic is Ben Shelton who should win in 4 sets.

(image) As per the initial odds, Ben Shelton is the pick to win this match.
Ben Shelton -> 1.32
Lorenzo Sonego -> 3.38

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Marin Cilic vs. Flavio Cobolli

Head to head 2-0 for Cobolli

Marin Cilic will come up against Flavio Cobolli in the 4^th round for the 3^rd time of their career. They are scheduled to play on Monday at 11:00 am on Court 2.

Marin Cilic: ranking and results

Ranked no. 83, the Croatian got to the 4^th round after beating Raphael Collignon 6-3 6-4 6-3, Jack Draper 6-4 6-3 1-6 6-4 and Jaume Antoni Munar Clar 6-3 3-6 6-2 6-4.

Cilic has a 22-10 win-loss record in 2025, 9-1 on grass (See FULL STATS). The Croatian’s best result of the current season was getting to the final in the Girona Challenger, the Madrid Challenger and the Nottingham 2 Challenger.

Last year at Wimbledon The Croatian didn’t compete at Wimbledon in 2024.

Flavio Cobolli: ranking and results

Ranked no. 24 (career high), the Italian got to the 4^th round after beating Beibit Zhukayev 6-3 7-6(7) 6-1, Jack Pinnington Jones 6-1 7-6(6) 6-2 and Jakub Mensik 6-2 6-4 6-2.

The Italian has a 23-17 win-loss record in 2025, 5-2 on grass (See FULL STATS). His best result of the year was winning the title in Bucharest where he defeated Sebastian Baez in the final 6-4 6-4 and in Hamburg where he overcame Andrey Rublev in the final 6-2 6-4.

Last year at Wimbledon Cobolli had to surrender in the 2^nd round 7-6(4) 7-6(4) 4-6 4-6 6-4 to Alejandro Tabilo.

Head to head analysis

This will be the 3^rd time that Marin Cilic and Flavio Cobolli face off. The head to head is 2-0 for Cobolli (see full H2H stats), but they have never competed against each other on grass.

Before, the last time they squared off, Cobolli won 6-2 6-1 6-3 in the 1^st round in Roland garros back in May 2025.

Prediction, odds and live streaming

The pick for Tennis Tonic is Marin Cilic who should win in 5 sets.

(image) As per the initial odds, Marin Cilic is the pick to win this match.
Marin Cilic -> 1.89
Flavio Cobolli -> 1.909

Click here to see the updated quotes and live streaming (only selected countries – USA excluded).

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Here where top tennis events are broadcasted or streamed online (ATP, WTA).

At the challenger level, there will be free live streaming on Challenger TV.

Last Results

These are the last results in Wimbledon

• Carlos AlcarazAlcaraz – Andrey RublevRublev (6-7⁵ 6-3 6-4 6-4) – Score progression – Stats
• Taylor FritzFritz – Jordan ThompsonThompson (6-1 3-0 ret.) – Score progression – Stats
• Cameron NorrieNorrie – Nicolas JarryJarry (6-3 7-6⁴ 6-7⁷ 6-7⁵ 6-3) – Score progression – Stats
• Karen KhachanovKhachanov – Kamil MajchrzakMajchrzak (6-4 6-2 6-3) – Score progression – Stats

Upcoming matches

These are the upcoming matches of the Wimbledon

• Marin CilicCilic – Flavio CobolliCobolli (0-2) – H2H – Prediction
• Cameron NorrieNorrie – Carlos Alcaraz GarfiaAlcaraz Garfia (2-4) – H2H – Prediction
• Taylor Harry FritzHarry Fritz – Karen KhachanovKhachanov (0-2) – H2H – Prediction
• Alex De MinaurDe Minaur – Novak DjokovicDjokovic (1-2) – H2H – Prediction
• Jannik SinnerSinner – Grigor DimitrovDimitrov (4-1) – H2H – Prediction

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