Stadium: Center Court Round: 26 Ground: Hardcourt outdoor
| ITF Zimbabwe F2 | 2018/06/05 09:15 | Lampasas, Ciro v Ianakiev, Milen | 1-6,0-6 |
| ITF Zimbabwe F1 | 2018/05/30 07:00 | Ianakiev, Milen v Sibanda, Mehluli Don Ayanda | 5-7,1-6 |
| 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 Zimbabwe F2 | 2018/06/06 09:45 | Ubon, Joseph Imeh v Benjamin Lock | 1-6,0-6 |
| ITF Zimbabwe F1 | 2018/06/02 08:00 | Benjamin Lock v Garanganga, Takanyi | 7-6,6-2 |
| ITF Zimbabwe F1 | 2018/06/01 08:00 | Benjamin Lock v Howard-Tripp, Joshua | 6-3,6-3 |
| ITF Zimbabwe F1 | 2018/05/31 08:00 | Benjamin Lock v Schmid, Aaron | 6-2,6-1 |
| ITF Zimbabwe F1 | 2018/05/30 07:00 | Benjamin Lock v Du Toit, Lance-Pierre | 6-2,6-1 |
| ITF Zimbabwe F1 | 2018/05/29 08:40 | Benjamin Lock v Bushamuka, William | 6-2,6-7,6-4 |
| Challenger Puerto Vallarta Qual | 2018/04/28 22:35 | Benjamin Lock v Martinez, Luis David | 6-4,4-6,6-7 |
| Challenger Leon Qual | 2018/04/21 19:00 | Franco Agamenone v Benjamin Lock | 6-4,7-6 |