Stadium: Court 2 Round: 26 Ground: Clay
| ITF USA F21 Qual | 2016/06/20 14:00 | Spec, Matic v C. Oosterbaan, Paul | 4-6,4-6 |
| Palm Coast, Singles M-ITF-USA-05A | 2019/01/22 15:00 | Gomez, Alejandro v C. Oosterbaan, Paul | 4-6,1-6 |
| ITF M15 Naples | 2019/01/15 18:30 | Dmitry Popko v C. Oosterbaan, Paul | 4-6,6-3,6-3 |
| ITF USA F35 | 2018/12/05 21:10 | Justin Roberts v C. Oosterbaan, Paul | 7-6,7-6 |
| ITF USA F35 | 2018/12/03 15:00 | C. Oosterbaan, Paul v Alex Knaff | 7-6,6-4 |
| USA F33, Singles | 2018/11/21 17:50 | C. Oosterbaan, Paul v Krainik, Pavel | 4-6,3-6 |
| USA F33, Singles | 2018/11/20 17:40 | Hidalgo, Diego v C. Oosterbaan, Paul | 6-7,7-5,3-6 |
| ITF USA F31 | 2018/11/14 15:00 | Calvo Eman, Ferran v C. Oosterbaan, Paul | 6-1,5-7,6-3 |
| ITF Vietnam F5 | 2018/10/30 03:00 | Roman Safiullin v C. Oosterbaan, Paul | 6-3,7-5 |
| Palm Coast, Singles M-ITF-USA-05A | 2019/01/23 18:05 | Spec, Matic v Jumpei Yamasaki | 6-3,7-6 |
| Palm Coast, Singles M-ITF-USA-05A | 2019/01/21 20:55 | Spec, Matic v Kohen, Alan | 6-2,6-3 |
| ITF Qatar F6 | 2018/12/19 12:00 | Spec, Matic v Jesper De Jong | 6-4,1-6,3-6 |
| ITF Qatar F6 | 2018/12/18 07:00 | Mikalai Haliak v Spec, Matic | 4-6,6-7 |
| ITF Qatar F6 | 2018/12/17 10:00 | Spec, Matic v Hendrik Jebens | 4-6,6-2,6-1 |
| ITF Qatar F6 | 2018/12/16 16:35 | Spec, Matic v Mircea, Claudiu | 6-1,6-3 |
| Qatar F5, Simples | 2018/12/11 17:45 | Spec, Matic v Antoine Bellier | 4-6,6-7 |
| Qatar F5, Simples | 2018/12/10 12:00 | Mikalai Haliak v Spec, Matic | 3-6,3-6 |