Ilia Simakin and Philip Henning will play each other in the 2nd round of the Chisinau Challenger for the 2nd time in their career. They are scheduled to play on Thursday at 1:30 pm on COURT 4. In the following lines you can find the head to head analysis and prediction.
Prediction, odds and live streaming
The pick for Tennis Tonic is Ilia Simakin who should win in 3 sets.
As per the initial odds, Ilia Simakin is the pick to win this match.
Ilia Simakin -> 1.41
Philip Henning -> 2.73
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Prediction and head to head Ilia Simakin vs. Philip Henning
This will be the 2nd time that Ilia Simakin and Philip Henning fight against each other. The head to head is 1-0 for Henning (see full H2H stats), 1-0 on hard.
The last time that they fought against each other, Henning won 6-4 2-6 6-4 in the semifinal in M15 Sharm ElSheikh back in 2023.
Ilia Simakin
| Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2025 | 31-11 | 31-11 | 0-0 | 0-0 | 0-0 | 0-0 |
| 2024 | 62-22 | 55-21 | 0-0 | 7-1 | 0-0 | 0-0 |
| 2023 | 31-19 | 28-18 | 3-1 | 0-0 | 0-0 | 0-0 |
| 2022 | 24-17 | 24-12 | 0-4 | 0-1 | 0-0 | 0-0 |
| 2021 | 1-2 | 0-0 | 0-0 | 1-2 | 0-0 | 0-0 |
Ranked no. 249, Simakin got to the 2nd round after beating Charlie Robertson 7-5 7-6(6).
In the 1st round, Ilia had a good straight sets win against Robertson (7-5 7-66). During the match, Simakin scored 97 points vs Robertson’s 84. The Russian was very aggressive to blast 35 winners.
Regarding the service games, Simakin bagged 5 aces and he committed only 3 double faults. Ilia Simakin lost the serve 3 times and he saved 3 break points. Furthermore, Simakin put 68% of his first serves in, winning 64% (35/55) of the points behind his 1st serve and 58% (15/26) on the 2nd serve. The Russian broke Robertson 4 times after converting 33% of his break points (4/12).
Simakin has a solid match record in the last 5 years having won 68% of his matches (146-70). 28-10 on hard in 2025. In connection with his performance on the same surface of this tournament, Simakin has an aggregate135-61 record in the last 5 years on hard.
The Russian’s best result of the year was getting to the semifinal in M15 Sharm ElSheikh,M15 Heraklion and the Wuxi Challenger.
Simakin has a compiled 28-10 win-loss record in 2025, 28-10 on hard (See FULL STATS).
Previously in the Chisinau Challenger
Ilia has never competed in this tournament before.
Philip Henning
| Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2025 | 11-12 | 7-7 | 0-0 | 4-5 | 0-0 | 0-0 |
| 2024 | 55-15 | 43-9 | 12-5 | 0-1 | 0-0 | 0-0 |
| 2023 | 23-4 | 23-4 | 0-0 | 0-0 | 0-0 | 0-0 |
| 2022 | 5-3 | 0-1 | 0-1 | 5-1 | 0-0 | 0-0 |
| 2021 | 2-1 | 2-1 | 0-0 | 0-0 | 0-0 | 0-0 |
Ranked no. 360, Philip got to the 2nd round after beating Daniil Glinka 2-6 7-6(3) 7-5.
In the 1st round against Glinka, Henning recovered from a 1-set down deficit before winning (2-6 7-63 7-5).During the match Henning scored less points (1) than Glinka. In fact, the world no. 249 won 104 points vs Glinka’s. That means that Henning was more focused during the important points. The South African was pretty aggressive to blast 55 winners.
About the serving games, Henning made 6 aces and he committed only 1 double fault for the entire match. Overall, Philip Henning was extremely efficient on serve to win 74% (55/74) of his 1st serve and 55% (17/31) on the second serve. However, this didn’t prevent his to concede the serve twice. Philip broke Glinka once after converting 33% of his break points (1/3).
Henning has a composed 11-11 win-loss record in 2025, 7-6 on hard (See FULL STATS).
H2H Performance in the tournament
Matches, sets, games and points
| Points | Simakin | Henning |
|---|---|---|
| Match played | 1 | 1 |
| Tot Set | 2 | 3 |
| Tot Games | 25 | 33 |
| Pts | 97-84 | 104-105 |
| Total Points | 181 | 209 |
| Winners | 35 | 55 |
| %Winners | 36% | 53% |
Both Simakin and Henning played 1 match. At the moment, Philip Henning dropped 1 set while Ilia Simakin hasn’t lost a set so far. Simakin has played 1 set(s) less than Henning (2 vs 3). Therefore, Simakin played 8 games less than Henning. Ilia scored 35 winners (36% of the total points). On the other side, Henning managed to score 55 winners (53%).
Serve Performance
| Serve | Simakin | Henning |
|---|---|---|
| Aces | 5 | 6 |
| Avg per match | 5 | 6 |
| 1st in | 55/81 | 74/105 |
| %1st in | 68% | 70% |
| 1st pts | 35/55 | 55/74 |
| %1st pts | 64% | 74% |
| 2nd pts | 15/26 | 17/31 |
| %2nd pts | 58% | 55% |
Simakin blasted 5 aces . Henning struck 6 aces . Simakin won 64% points on his first serve. He pretty effective on his second serve to win 58% of the points. On the other side, Henning won 74% of the points behind his first serve. He had a solid display on his second serve to win 55% of the points.
How they played the important points
| Breaks | Simakin | Henning |
|---|---|---|
| Won | 4 | 1 |
| Converted | 4/12 | 1/3 |
| % Converted | 33% | 33% |
| Conceded | 6 | 9 |
| Saved | 3 | 7 |
| % Saved | 50% | 78% |
| Times Broken | 3 | 2 |
Ilia broke his opponent 4 times with a 33% conversion rate. Simakin surrendered his serve 3 times and he saved 50% of the break points that he conceded. Henning broke his opponent once with a 33% conversion rate. Henning conceded his serve twice and he saved 78% of the break points that he conceded.
| Simakin | |||
| R1 Robertson |
Total | ||
|---|---|---|---|
| Score | 7-5 7-66 | ||
| Tot Set | 2 | 2 | |
| Tot Games | 25 | 25 | |
| pts | 97-84 | 97-84 | |
| Total points | 181 | 181 | |
| Winners | 35 | 35 | |
| %Winners | 36% | 36% | |
| SERVE | |||
| Aces | 5 | 5 | |
| Double Faults | 3 | 3 | |
| 1st in | 55/81 | 55/81 | |
| % 1st in | 68% | 68% | |
| 1st pts | 35/55 | 35/55 | |
| % 1st pts | 64% | 64% | |
| 2nd pts | 15/26 | 15/26 | |
| % 2nd pts | 58% | 58% | |
| Breaks | |||
| Won | 4 | 4 | |
| Converted | 4/12 | 4/12 | |
| Converted % | 33% | 33% | |
| Conceded | 6 | 6 | |
| Saved | 3/6 | 3 | |
| Saved % | 50% | 50% | |
| Times Broken | 3 | 3 | |
| Henning | |||
| R1 Glinka |
Total | ||
|---|---|---|---|
| Score | 2-6 7-63 7-5 | ||
| Tot Set | 3 | 3 | |
| Tot Games | 33 | 33 | |
| pts | 104-105 | 104-105 | |
| Total points | 209 | 209 | |
| Winners | 55 | 55 | |
| %Winners | 53% | 53% | |
| SERVE | |||
| Aces | 6 | 6 | |
| Double Faults | 1 | 1 | |
| 1st in | 74/105 | 74/105 | |
| % 1st in | 70% | 70% | |
| 1st pts | 55/74 | 55/74 | |
| % 1st pts | 74% | 74% | |
| 2nd pts | 17/31 | 17/31 | |
| % 2nd pts | 55% | 55% | |
| Breaks | |||
| Won | 1 | 1 | |
| Converted | 1/3 | 1/3 | |
| Converted % | 33% | 33% | |
| Conceded | 9 | 9 | |
| Saved | 7/9 | 7 | |
| Saved % | 78% | 78% | |
| Times Broken | 2 | 2 | |
Head 2 Head
LWWWWLWLWW
LWLLWLLWWL Tennis Scores in Chisinau Challenger
- Robert StrombachsStrombachs – Jay ClarkeClarke (6-3 6-4) – See score progression
- Philip HenningHenning – Daniil GlinkaGlinka (2-6 7-63 7-5) – See score progression
- Giles HusseyHussey – Robin BertrandBertrand (7-5 6-1) – See score progression
- Petr Bar BiryukovBar Biryukov – Saba PurtseladzePurtseladze (6-4 7-62) – See score progression
- Clement ChidekhChidekh – Lukas PokornyPokorny (6-2 7-5) – See score progression
- Evgeny KarlovskiyKarlovskiy – Egor GerasimovGerasimov (6-4 6-4) – See score progression
- Olaf PieczkowskiPieczkowski – Aleksandre BakshiBakshi (7-66 2-0 ret.) – See score progression
- Ilia SimakinSimakin – Charlie RobertsonRobertson (7-5 7-66) – See score progression
- Kaichi UchidaUchida – Charles BroomBroom (7-62 6-73 7-67) – See score progression
- Cem IlkelIlkel – Mukund SasikumarSasikumar (6-4 6-3) – See score progression
- Masamichi ImamuraImamura – Kasidit SamrejSamrej (6-4 7-5) – See score progression
- Toby SamuelSamuel – Lilian MarmousezMarmousez (7-5 6-2) – See score progression
- Radu AlbotAlbot – Ricardas BerankisBerankis (7-63 4-6 7-67) – See score progression
- Denis YevseyevYevseyev – Harry WendelkenWendelken (3-6 6-1 6-4) – See score progression
- Lorenzo GiustinoGiustino – Alastair GrayGray (6-2 4-6 7-67) – See score progression
- Stuart ParkerParker – Ilya SnitariSnitari (6-2 6-1) – See score progression
- Olaf PieczkowskiPieczkowski – Aleksandre BakshiBakshi (7-6(6) 2-0 ret.) – See score progression
- Evgeny KarlovskiyKarlovskiy – Egor GerasimovGerasimov (6-4 6-4) – See score progression
- Robert StrombachsStrombachs – Jay ClarkeClarke (6-3 6-4) – See score progression
Upcoming matches in the draw
- Lorenzo GiustinoGiustino – Stuart ParkerParker (1-0) – H2H and prediction
- Denis YevseyevYevseyev – Kaichi UchidaUchida (1-1) – H2H and prediction
- Cem IlkelIlkel – (0-0) – H2H and prediction
- Evgeny KarlovskiyKarlovskiy – Robert StrombachsStrombachs (0-0) – H2H and prediction
- Masamichi ImamuraImamura – (0-0) – H2H and prediction
- Clement ChidekhChidekh – (0-0) – H2H and prediction
