Stadium: Court 2 Round: 26 Ground: Clay
| ITF USA F21 Qual | 2016/06/20 14:00 | Matic Spec v Paul Oosterbaan | 4-6,4-6 |
| 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 USA F31 | 2018/11/14 15:00 | Ferran Calvo Eman v Paul Oosterbaan | 6-1,5-7,6-3 |
| ITF Vietnam F5 | 2018/10/30 03:00 | Roman Safiullin v Paul Oosterbaan | 6-3,7-5 |
| ITF M25 Palm Coast | 2019/01/23 18:05 | Matic Spec v Jumpei Yamasaki | 6-3,7-6 |
| ITF M25 Palm Coast | 2019/01/21 20:55 | Matic Spec v Alan Kohen | 6-2,6-3 |
| ITF Qatar F6 | 2018/12/19 12:00 | Matic Spec v Jesper De Jong | 6-4,1-6,3-6 |
| ITF Qatar F6 | 2018/12/18 07:00 | Mikalai Haliak v Matic Spec | 4-6,6-7 |
| ITF Qatar F6 | 2018/12/17 10:00 | Matic Spec v Hendrik Jebens | 4-6,6-2,6-1 |
| ITF Qatar F6 | 2018/12/16 16:35 | Matic Spec v Claudiu Mircea | 6-1,6-3 |
| ITF Qatar F5 | 2018/12/11 17:45 | Matic Spec v Antoine Bellier | 4-6,6-7 |
| ITF Qatar F5 | 2018/12/10 12:00 | Mikalai Haliak v Matic Spec | 3-6,3-6 |