Stadium: Court 1 Round: 26 Ground: Clay
| ITF Dominican Republic F2 | 2018/12/04 18:30 | Milen Ianakiev v Dusty H. Boyer | 7-6,6-7,6-2 |
| ITF Dominican Republic F2 | 2018/12/03 13:00 | Milen Ianakiev v Philip Wilbert Major | 7-6,6-3 |
| 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 Dominican Republic F2 | 2018/12/04 18:40 | Simon Freund v Jose Pereira | 6-4,6-7,7-6 |
| ITF Dominican Republic F2 | 2018/12/03 13:00 | Kevin Major v Simon Freund | 6-7,2-6 |
| ITF Dominican Republic F2 | 2018/12/02 14:00 | Simon Freund v Junior T Pichardo | 6-1,6-0 |
| ITF Dominican Republic F2 | 2018/12/01 14:00 | Michel-Alexandre Fortin v Simon Freund | 5-7,0-6 |
| ITF Dominican Republic F1 | 2018/11/27 14:55 | Dusty H. Boyer v Simon Freund | 6-2,2-6,6-2 |
| ITF Dominican Republic F1 | 2018/11/26 13:00 | Emmett Ward v Simon Freund | 4-6,1-6 |
| ITF Dominican Republic F1 | 2018/11/25 14:00 | Simon Freund v Anshumat Srivastava | 6-0,6-3 |
| ITF Dominican Republic F1 | 2018/11/24 13:30 | Simon Freund v Arsav Mohanty | 6-4,6-1 |