| UTR Pro Tennis Series Sofia | 2021/08/31 09:30 | Ianakiev, Milen v Lazov, Alexander | 6-7,2-6 |
| UTR Pro Tennis Series Sofia | 2021/08/30 08:30 | Ianakiev, Milen v Dzhavakian, Yurii | 4-6,2-6 |
| ITF - M15 Doha | 2020/03/12 13:55 | Ianakiev, Milen v Deviatiarov, Marat | 2-6,0-6 |
| ITF - M15 Doha | 2020/03/11 13:05 | Ianakiev, Milen v Rashed Nawaf | 3-6,6-1,6-2 |
| ITF - M15 Doha | 2020/03/10 12:00 | Ianakiev, Milen v Abdulla, Mohammed | 6-2,6-2 |
| ITF - M15 Héraklion | 2019/12/08 10:00 | Ianakiev, Milen v Sizya Ernest Kivanda | 2-6,6-2,8-10 |
| ITF - M15 Héraklion | 2019/12/02 09:30 | Amatiste, Gianmarco v Ianakiev, Milen | 3-6,6-3,10-4 |
| ITF - M15 Héraklion | 2019/12/01 14:00 | Nincevic, Frane v Ianakiev, Milen | 3-6,6-4,8-10 |
| UTR Pro Tennis Series Sofia | 2021/08/31 09:30 | Dzhavakian, Yurii v de Cuyper, Julien | 6-0,5-0 |
| UTR Pro Tennis Series Sofia | 2021/08/30 11:30 | de Cuyper, Julien v Lazov, Alexander | 2-6,2-5 |
| UTR Pro Tennis Series Portoroz | 2021/08/28 08:30 | Dusan Trunic v de Cuyper, Julien | 3-0 |
| UTR Pro Tennis Series Portoroz | 2021/08/27 12:00 | de Cuyper, Julien v Dahiya, Paras | 6-1,4-6,6-4 |
| UTR Pro Tennis Series Portoroz | 2021/08/26 07:00 | de Cuyper, Julien v Gal Emersic Potocnik | 1-6,0-5 |
| ITF M15 Pescara | 2021/08/16 07:15 | de Cuyper, Julien v Spinnato, Daniele | 1-6,3-6 |
| ITF M15 Pescara | 2021/08/15 11:30 | Campo, Antonio v de Cuyper, Julien | 3-6,6-3,6-10 |
| ITF M15 Esch/Alzette | 2021/07/20 10:55 | de Cuyper, Julien v Tommaso Compagnucci | 2-6,1-6 |