Stadium: Court 9 Round: 62 Ground: Clay
| ITF Dominican Republic F2 | 2018/12/02 14:00 | Milen Ianakiev v Jesus M Rosario | 6-3,6-1 |
| 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 Dominican Republic F2 | 2018/12/02 14:00 | Philip Wilbert Major v Christopher Rosensteel | 6-3,7-6 |
| ITF Canada F7 | 2018/09/08 15:00 | Philip Wilbert Major v Kevin Portmann | 6-2,7-5 |
| ITF Canada F7 | 2018/09/08 14:00 | Philip Wilbert Major v Aleksandar Kovacevic | 1-6,2-6 |
| ITF Canada F6 | 2018/09/01 15:00 | Philip Wilbert Major v Alexander Knight | 1-6,4-6 |
| Davis Cup | 2018/06/02 15:00 | Philip Wilbert Major v Sebastian Quiros | 6-2,6-2 |
| Davis Cup | 2018/05/31 15:00 | Dimitri Bird v Philip Wilbert Major | 1-6,3-6 |
| Davis Cup | 2018/05/29 15:00 | Philip Wilbert Major v Shakir Elvin | 6-4,6-3 |
| Davis Cup | 2018/05/28 15:00 | Keny Turcios v Philip Wilbert Major | 4-6,2-6 |