Jacopo Berrettini and Henri Squire will play each other in the 1^st round of the Milan Challenger for the 1^st time in their career. They are scheduled to play on Tuesday at 10:00 am on CENTER COURT. Here the head to head stats and relative prediction.

Prediction, odds and live streaming

The pick for Tennis Tonic is Henri Squire who should win in 3 sets.

As per the initial odds, Henri Squire is the pick to win this match.
Henri Squire -> 1.83
Jacopo Berrettini -> 1.89

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Prediction and head to head Jacopo Berrettini vs. Henri Squire

There is no head to head record between Jacopo Berrettini and Henri Squire since this will be the first time that they will square off in the main tour.

Jacopo Berrettini

Ranked no. 330, Jacopo reached the 1^st round after defeating Max Wiskandt 7-6(6) 6-7(5) 6-4 and Mikael Ymer 7-5 6-2.

In the qualifications, The Italian had a good straight sets win against Ymer (7-5 6-2). During the match, Berrettini scored 74 points vs Ymer’s 55. Jacopo was exceptionally aggressive to blast 32 winners.

Talking about the service games, Berrettini scored 2 aces and he committed only 4 double faults. Jacopo Berrettini lost the serve once and he saved 2 break points. Furthermore, Berrettini put 59% of his first serves in, winning 80% (32/40) of the points behind his 1st serve and 43% (12/28) on the 2nd serve. Jacopo broke Ymer 4 times after converting 67% of his break points (4/6).

Overall Performance in this tournament

Jacopo started his run at this tournament from the qualifications. In the main draw, he has conceded 1 set in this event to conquer 53% of the points he played.

Berrettini has good win-loss record in the last 10 years having won 55% of his matches (223-182). 18-8 on clay in 2025. In connection with his performance on the same surface of this event, Berrettini has an overall 142-108 match record in the last years on clay.

Jacopo’s best result of the current season was getting to the final in M25 Cervia and M25 Cordoba.

The Italian has an overall 21-12 win-loss record in 2025, 18-8 on clay (See FULL STATS).

Previously in the Milan Challenger

Henri Squire

Ranked no. 358, Henri will start his run in the Milan Challenger after he played his last match in the Poznan Challenger where he lost 6-4 7-6(6)

to Svrcina in the 1^st round on the 17^th of June.

Henri has a composed 13-20 win-loss record in 2025, 6-12 on clay (See FULL STATS).

In terms of his career, The German has an overall 186-151 record. He has a positive 93-83 record on clay.

Tennis Scores in Milan Challenger

• Luka MikrutMikrut – Kimmer CoppejansCoppejans (6-4 6-4) – Stats, scores, rankings
• Arthur GeaGea – Diego Dedura-PalomeroDedura-Palomero (7-6⁴ 6-1) – Stats, scores, rankings
• Ivan GakhovGakhov – Andrej MartinMartin (3-6 6-1 7-6³) – Stats, scores, rankings
• Dino PrizmicPrizmic – Gabriele PirainoPiraino (6-1 6-4) – Stats, scores, rankings
• Oleg PrihodkoPrihodko – Radu AlbotAlbot (6-3 6-4) – Stats, scores, rankings
• Rafael JodarJodar – Lorenzo GiustinoGiustino (6-0 6-2) – Stats, scores, rankings

Upcoming matches in the draw

• Oriol Roca BatallaRoca Batalla – (0-0) – H2H and prediction
• Marco CecchinatoCecchinato – Max Alcala GurriAlcala Gurri (0-0) – H2H and prediction
• Frederico Ferreira SilvaFerreira Silva – Alexey VatutinVatutin (0-2) – H2H and prediction
• Oleg PrihodkoPrihodko – (1-1) – H2H and prediction
• Giovanni FonioFonio – Max HoukesHoukes (1-0) – H2H and prediction
• Jacopo BerrettiniBerrettini – Henri SquireSquire (0-0) – H2H and prediction
• Mathys ErhardErhard – Christoph NegrituNegritu (1-0) – H2H and prediction
• Matias SotoSoto – (0-0) – H2H and prediction