Stadium: Court 3 Round: 26 Ground: Hardcourt outdoor
| ITF Zimbabwe F1 | 2018/05/28 09:45 | Paul, Christian v Ianakiev, Milen | 0-6,3-6 |
| ITF Bulgaria F1 | 2018/05/17 07:00 | Ianakiev, Milen v Boltz, Sebastien | 3-6,2-6 |
| ITF Bulgaria F1 | 2018/05/15 10:00 | Ianakiev, Milen v Ontica, Cosmin | 6-1,6-2 |
| ITF Israel F6 | 2018/05/07 09:00 | Elia, Alon v Ianakiev, Milen | 5-7,7-5,6-3 |
| ITF USA F10 Qual | 2018/04/09 15:00 | Joseph Corse v Ianakiev, Milen | 6-3,6-0 |
| ITF USA F10 Qual | 2018/04/08 20:00 | Kandath, Matthew v Ianakiev, Milen | 6-3,6-7,6-7 |
| ITF Bahrain F1 | 2018/03/21 15:40 | Colautti, Thomas v Ianakiev, Milen | 6-3,7-5 |
| ITF Bahrain F1 | 2018/03/20 09:40 | Ianakiev, Milen v Vitaliy Sachko | 7-6,7-6 |
| ITF Zimbabwe F1 | 2018/05/28 08:00 | Sibanda, Mehluli Don Ayanda v Bojanovic, Darko | 6-1,2-6,6-2 |
| ITF Uganda F1 | 2018/05/02 07:35 | Sibanda, Mehluli Don Ayanda v Samaha, Giovani | 4-6,4-6 |
| ITF Uganda F1 | 2018/05/01 08:00 | Sibanda, Mehluli Don Ayanda v Samaha, Giovani | 4-6,4-6 |
| ITF Uganda F1 | 2018/04/29 12:00 | Solberg, Christoffer v Sibanda, Mehluli Don Ayanda | 6-0,1-6,0-6 |
| Coupe Davis | 2018/02/04 20:15 | Sibanda, Mehluli Don Ayanda v Sarp Agabigun | 5-7,4-6 |
| ITF South Africa F3 Qual | 2017/12/02 10:00 | Du Toit, Riaan v Sibanda, Mehluli Don Ayanda | 6-3,6-1 |
| Afrique du Sud F2, Qualifications Simples | 2017/11/26 11:20 | Colautti, Thomas v Sibanda, Mehluli Don Ayanda | 6-3,6-3 |
| Afrique du Sud F2, Qualifications Simples | 2017/11/25 08:45 | Puttergill, Liam v Sibanda, Mehluli Don Ayanda | 1-6,2-6 |