Level, 1 wins each over 2 singles meetings since 2023. Last meeting on 29/05/2025 at Chisinau Challenger.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 29/05/2025 | Chisinau Challenger | Round 2 | clay | Simakin | 6-4 6-1 |
| 14/10/2023 | M15 Sharm ElSheikh | Semi-final | hard | Henning | 6-4 2-6 6-4 |
| clay | Henning 0 - 1 Simakin |
| hard | Henning 1 - 0 Simakin |
| 2025 | Henning 0 - 1 Simakin |
| 2023 | Henning 1 - 0 Simakin |
162 wins, 61 losses since 2021 (72.6%).
Last matches: D V D V D
197 wins, 97 losses since 2021 (67.0%).
Last matches: D V D D V
Level, 1 wins each over 2 singles meetings since 2023.
On 29/05/2025, at Chisinau Challenger (Round 2): Ilia Simakin won 6-4 6-1.