Stadium: Court 1 Round: 62 Ground: Clay
| ITF Dominican Republic F1 | 2018/11/28 15:30 | Oscar Jose Gutierrez v Milen Ianakiev | 4-6,6-3,6-4 |
| ITF USA F26 | 2018/09/26 22:00 | Milen Ianakiev v Michael Shabaz | 2-6,2-6 |
| ITF USA F25 | 2018/09/19 17:00 | Milen Ianakiev v Govind Nanda | 5-7,1-6 |
| ITF USA F24 | 2018/09/11 16:30 | Milen Ianakiev v Sumit Sarkar | 3-6,1-6 |
| ITF Netherlands F4 | 2018/08/13 10:00 | Milen Ianakiev v Justin Butsch | 2-6,1-6 |
| ITF Netherlands F4 | 2018/08/13 07:30 | Milen Ianakiev v Lautaro Agustin Falabella | 3-6,6-3,7-5 |
| ITF Germany F11 | 2018/08/07 16:25 | Lucas Poullain v Milen Ianakiev | 6-3,6-2 |
| ITF France F15 | 2018/07/25 08:00 | Fabien Reboul v Milen Ianakiev | 7-6,6-2 |
| ITF Dominican Republic F2 | 2018/12/01 14:00 | Danail Banov v Jesus M Rosario | 6-4,3-6,5-7 |
| ITF Dominican Republic F1 | 2018/11/25 14:00 | Omni Kumar v Jesus M Rosario | 6-2,6-3 |
| Challenger Santo Domingo | 2018/10/06 19:45 | Jesus M Rosario v Riccardo Bellotti | 0-6,0-6 |
| Challenger Santo Domingo Qual | 2017/08/12 15:00 | Carlos Boluda-Purkiss v Jesus M Rosario | 6-0,6-1 |