Stadium: Court 1 Round: 45 Ground: Clay
| ITF M25 Palm Coast | 2019/01/25 15:00 | Paul Oosterbaan v Or Ram-Harel | 2-6,1-6 |
| ITF M25 Palm Coast | 2019/01/24 18:00 | Paul Oosterbaan v Matic Spec | 6-2,6-4 |
| ITF M25 Palm Coast | 2019/01/22 15:00 | Alejandro Gomez v Paul Oosterbaan | 4-6,1-6 |
| ITF M15 Naples | 2019/01/15 18:30 | Dmitry Popko v Paul Oosterbaan | 4-6,6-3,6-3 |
| ITF USA F35 | 2018/12/05 21:10 | Justin Roberts v Paul Oosterbaan | 7-6,7-6 |
| ITF USA F35 | 2018/12/03 15:00 | Paul Oosterbaan v Alex Knaff | 7-6,6-4 |
| ITF USA F33 | 2018/11/21 17:50 | Paul Oosterbaan v Pavel Krainik | 4-6,3-6 |
| ITF USA F33 | 2018/11/20 17:40 | Diego Hidalgo v Paul Oosterbaan | 6-7,7-5,3-6 |
| ITF M25 Palm Coast | 2019/01/23 16:15 | Boris Arias v Pietro Rondoni | 5-7,3-6 |
| ITF M25 Palm Coast | 2019/01/21 19:15 | Nicolas Mejia v Boris Arias | 6-2,6-1 |
| ITF M25 Palm Coast | 2019/01/21 15:00 | Sergey Belov v Boris Arias | 4-6,7-6,6-10 |
| ITF USA F34 | 2018/11/24 18:30 | Boris Arias v Elio Jose Ribeiro Lago | 5-7,6-7 |
| ITF USA F33 | 2018/11/18 15:55 | Boris Arias v Alex Kobelt | 1-6,4-6 |
| ITF USA F33 | 2018/11/17 15:00 | Boris Arias v Varun Jayaram | 6-2,7-5 |
| ITF USA F31 | 2018/11/12 17:30 | Boris Arias v Maxim Tybar | 5-7,5-7 |
| ITF USA F29 | 2018/10/30 15:00 | Fabrizio Ornago v Boris Arias | 6-3,6-4 |