Stadium: Stadium Round: 27 Ground: Clay
| ITF Dominican Republic F2 | 2018/12/05 16:05 | Juan Sebastian Gomez v Olivares, Jose | 4-6,2-6 |
| ITF Dominican Republic F2 | 2018/12/04 19:10 | Butsch, Justin v Olivares, Jose | 3-6,4-6 |
| ITF Dominican Republic F1 | 2018/12/01 15:00 | Crepatte, Baptiste v Olivares, Jose | 6-3,6-2 |
| ITF Dominican Republic F1 | 2018/11/30 15:00 | Alejandro Tabilo v Olivares, Jose | 5-7,3-6 |
| ITF Dominican Republic F1 | 2018/11/29 15:40 | Schmid, Aaron v Olivares, Jose | 2-6,2-6 |
| ITF Dominican Republic F1 | 2018/11/28 15:55 | Blumenberg, Alex v Olivares, Jose | 3-6,1-6 |
| ITF USA F32 | 2018/11/15 18:00 | Rowland Phillips v Olivares, Jose | 3-6,6-4,10-8 |
| ITF USA F30 | 2018/11/08 19:30 | Kohen, Alan v Olivares, Jose | 6-3,6-3 |
| ITF Dominican Republic F2 | 2018/12/05 17:50 | Ianakiev, Milen v Simon Freund | 3-6,4-6 |
| 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 | Major, Kevin v Simon Freund | 6-7,2-6 |
| ITF Dominican Republic F2 | 2018/12/02 14:00 | Simon Freund v Tavarez Pichardo, Junior | 6-1,6-0 |
| ITF Dominican Republic F2 | 2018/12/01 14:00 | Fortin, Michel-Alexandre v Simon Freund | 5-7,0-6 |
| ITF Dominican Republic F1 | 2018/11/27 14:55 | Boyer, Dusty H 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 Srivastava, Anshumat | 6-0,6-3 |