Stadium: Court 16 Ground: Hardcourt outdoor
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/05 14:10 | Ianakiev, Milen v Sizya Ernest Kivanda | 2-6,4-6 |
| ITF M25 Roehampton | 2019/07/29 08:30 | Ianakiev, Milen v Modica, Sacha | 4-6,2-6 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 06:30 | Ianakiev, Milen v Bessire, Andrea | 4-6,2-6 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/03 10:00 | Ianakiev, Milen v Ontica, Cosmin | 1-6,6-4,10-6 |
| ITF - M15 Héraklion | 2019/05/28 09:00 | Omni Kumar v Ianakiev, Milen | 6-3,7-5 |
| ITF - M15 Héraklion | 2019/05/23 08:50 | Artunedo Martinav. v Ianakiev, Milen | 6-3,6-4 |
| ITF - M15 Héraklion | 2019/05/22 06:55 | Story, James v Ianakiev, Milen | 3-6,4-6 |
| ITF - M15 Héraklion | 2019/05/20 13:00 | Ianakiev, Milen v Roumpis, Alexandros | 6-4,6-2 |
| ITF M15 Fayetteville | 2019/09/17 14:30 | Cenoz, Juan Pablo v Nava, Diego | 6-3,3-6,10-7 |
| USA F26, Singles Qualifying | 2018/09/23 17:00 | Major, Kevin v Nava, Diego | 6-4,7-6 |
| USA F26, Singles Qualifying | 2018/09/22 16:30 | Nava, Diego v Valencia, Alejandro | 3-6,6-3,6-2 |
| ITF Morocco F3 | 2018/07/29 13:00 | Santalla, Ezequiel Agustin v Nava, Diego | 6-3,6-0 |
| ITF Morocco F2 | 2018/07/22 09:00 | Nava, Diego v Fattar, Anas | 3-6,0-6 |
| ITF Morocco F2 | 2018/07/21 11:00 | Nava, Diego v Eminefendic, Ervin Haris | 6-2,6-2 |
| ITF Morocco F1 | 2018/07/14 09:00 | Aswat, Imran v Nava, Diego | 6-4,6-1 |
| ITF USA F30 | 2017/09/09 19:30 | Nguyen Hoang, Thien v Nava, Diego | 6-4,2-6,2-6 |