Stadium: Court 1 Round: 54 Ground: Hardcourt outdoor
| ITF Dominican Republic F2 | 2018/12/05 17:50 | Milen Ianakiev v Simon Freund | 3-6,4-6 |
| 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 M15 Manacor | 2019/01/07 09:00 | Dennis Uspensky v Jack Gibbens | 6-4,6-4 |
| ITF Greece F8 | 2018/11/11 08:00 | Martin Dimitrov v Jack Gibbens | 6-3,6-4 |
| ITF Greece F8 | 2018/11/10 07:30 | Jack Gibbens v Kenta Kurita | 3-6,6-1,7-6 |
| ITF Greece F7 | 2018/11/07 07:30 | Michail Pervolarakis v Jack Gibbens | 6-4,6-1 |
| ITF Greece F7 | 2018/11/05 07:30 | Stefano Battaglino v Jack Gibbens | 6-3,3-6,4-6 |
| ITF Greece F7 | 2018/11/04 08:00 | Augusto Virgili v Jack Gibbens | 1-6,7-6,2-6 |
| ITF Great Britain F6 | 2018/09/23 11:30 | Jesse Ross v Jack Gibbens | 6-3,7-5 |
| ITF Great Britain F4 | 2018/09/09 09:00 | Jack Gibbens v Jamie Asanee Praditngam | 3-6,6-7 |