Stadium: Court 1 Round: 25 Ground: Clay
| ITF - Pazardzhik M15 | 2023/05/20 07:00 | Gabriel Donev v Denis Klok | 6-7,5-7 |
| ITF - Belgrad M15 | 2023/06/28 12:30 | Miljan Zekic v Gabriel Donev | 6-4,6-3 |
| ITF - Kursumlijska Banja M15 | 2023/06/17 17:15 | Gabriel Donev v Marat Sharipov | 3-6,4-6 |
| ITF - Kursumlijska Banja M15 | 2023/06/17 12:00 | Lautaro Midon v Gabriel Donev | 0-6,5-7 |
| ITF - Kursumlijska Banja M15 | 2023/06/13 15:55 | Iliyan Radulov v Gabriel Donev | 2-6,4-6 |
| ITF - Pazardzhik M15 | 2023/05/25 08:30 | Simone Roncalli v Gabriel Donev | 6-1,6-1 |
| ITF - Pazardzhik M15 | 2023/05/24 10:25 | Kane Bonsach Ganley v Gabriel Donev | 3-6,1-6 |
| ITF - Pazardzhik M15 | 2023/05/20 07:00 | Gabriel Donev v Denis Klok | 6-7,5-7 |
| ITF - Pazardzhik M15 | 2023/05/19 07:50 | Filip Cristian Jianu v Gabriel Donev | 4-6,5-7 |
| ITF - Belgrad M15 | 2023/06/29 06:50 | Denis Klok v Ergi Kirkin | 6-7,3-6 |
| ITF - Teheran M15 | 2023/06/18 12:30 | Denis Klok v Erik Arutiunian | 6-2,6-1 |
| ITF - Teheran M15 | 2023/06/16 08:00 | Denis Klok v Grigoriy Lomakin | 6-1,6-2 |
| ITF - Teheran M15 | 2023/06/15 06:30 | Denis Klok v Rostislav Galfinger | 6-1,6-2 |
| ITF - Teheran M15 | 2023/06/14 06:30 | Denis Klok v Saveliy Ivanov | 6-3,6-2 |
| ITF - Teheran M15 | 2023/06/08 06:00 | Alexander Stater v Denis Klok | 3-6,6-3,7-5 |
| ITF - Teheran M15 | 2023/06/07 09:55 | Manish Ganesh v Denis Klok | 2-6,2-6 |
| ITF - Kiseljak M25 | 2023/06/01 12:30 | Denis Klok v Dmitry Popko | 5-7,2-6 |