Stadium: Court 10 ParkEzeroto Round: 44 Ground: Clay
| ITF M15 Chornomorsk | 2019/09/24 08:05 | Bortolotti, Marco v Niv, Benjamin | 3-6,6-0,6-3 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/12 07:00 | Quentin Folliot v Niv, Benjamin | 6-1,6-1 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/11 10:00 | Niv, Benjamin v Lenaerts, Yannick | 6-2,6-3 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/09 13:00 | Niv, Benjamin v Vodavoz, Nir | 3-6,3-6 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/09 06:30 | Niv, Benjamin v Shandarov, Radoslav | 3-6,7-6,15-13 |
| Dublin, Singles Qualifying M-ITF-IRL-01A | 2019/07/29 13:00 | Niv, Benjamin v Lynch, Philip | 4-6,3-6 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 06:30 | Alexander Weis v Niv, Benjamin | 6-4,6-4 |
| ITF M15 Sozopol | 2019/05/09 08:25 | Altug Celikbilek v Niv, Benjamin | 6-2,6-4 |
| Varna, Singles M-ITF-BUL-04A | 2019/09/11 10:00 | Ivanov, Valentin v Wojnar, Bartosz | 1-6,0-6 |
| ITF - M15 Héraklion | 2019/05/27 08:15 | Patrick Foley v Ivanov, Valentin | 6-0,6-0 |
| ITF M15 Sozopol | 2019/05/06 08:30 | Ivanov, Valentin v Tsebrenko, Daniil | 3-6,0-6 |
| ITF Greece F6 | 2018/10/27 06:00 | Gostincar, Domen v Ivanov, Valentin | 6-3,6-1 |
| ITF Serbia F3 | 2018/08/18 07:00 | Ivanov, Valentin v Matic, Mile | 1-6,0-6 |
| ITF Romania F8 | 2018/08/05 11:30 | Ivanov, Valentin v Bogdan Pavel | 2-6,1-6 |
| ITF Bulgaria F1 | 2018/05/12 07:00 | Ivanov, Valentin v Khunarikov, Ruslan | 2-6,2-6 |