Ground: Hardcourt outdoor
| Challenger Chisinau | 2025/05/29 09:50 | Ilia Simakin v Philip Henning | 6-4,6-1 |
| Challenger Chisinau | 2025/05/28 07:00 | Philip Henning v Daniil Glinka | 2-6,7-6,7-5 |
| Challenger Tbilisi | 2025/05/19 11:10 | Johannus Monday v Philip Henning | 6-4,3-6,7-5 |
| ITF M25 Tbilisi | 2025/05/14 07:00 | Philip Henning v Petr Bar Biryukov | 3-6,4-6 |
| ITF M25 Tbilisi | 2025/05/12 10:17 | Sergey Fomin v Philip Henning | 3-6,0-6 |
| ITF M25 Nottingham | 2025/05/07 09:00 | Philip Henning v Luke Hooper | 6-7,4-6 |
| ITF M25 Nottingham | 2025/05/02 09:00 | Justin Boulais v Philip Henning | 7-5,5-7,7-6 |
| ITF M25 Nottingham | 2025/05/01 09:00 | Harry Wendelken v Philip Henning | 3-6,2-5 |
| ITF M15 Slovenska Bistrica | 2024/07/15 13:00 | Volodymyr Iakubenko v Nazar Oliynykov | 2-6,3-6 |
| ITF M15 Litija | 2024/07/10 16:50 | Volodymyr Iakubenko v Ziga Sesko | 6-2,6-3 |
| ITF M15 Hrastnik | 2024/06/06 11:00 | Bor Artnak v Volodymyr Iakubenko | 5-7,6-1,6-4 |
| ITF M15 Hrastnik | 2024/06/05 09:35 | Volodymyr Iakubenko v Miha Vetrih | 6-1,6-1 |
| ITF M25 Calabasas | 2024/03/19 17:00 | Volodymyr Iakubenko v Miles Jones | 5-7,3-6 |
| ITF M25 Calabasas | 2024/03/18 17:00 | Volodymyr Iakubenko v Matthew Vos | 6-1,6-1 |
| ITF M15 Ceuta | 2023/12/15 10:00 | Diego A B Sanchez v Volodymyr Iakubenko | 6-1,6-4 |
| ITF M15 Ceuta | 2023/12/14 10:30 | Volodymyr Iakubenko v Alen Moritz Hodzic | 6-3,6-1 |