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 | 4-6 6-2 4-6 |
| clay | Henning 0 - 1 Simakin |
| hard | Henning 1 - 0 Simakin |
| 2025 | Henning 0 - 1 Simakin |
| 2023 | Henning 1 - 0 Simakin |
153 wins, 54 losses since 2021 (73.9%).
Last matches: V V V D V
194 wins, 94 losses since 2021 (67.4%).
Last matches: V V V V 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.