Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Faro | 2019/02/26 11:55 | Laurent Lokoli v Paul Oosterbaan | 5-7,3-6 |
| ITF M15 Faro | 2019/02/25 10:00 | Yshai Oliel v Paul Oosterbaan | 6-7,3-6 |
| ITF M15 Vale Do Lobo | 2019/02/19 13:00 | Paul Oosterbaan v Finn Tearney | 4-6,5-7 |
| ITF M25 Weston | 2019/01/31 18:00 | Dmitry Popko v Paul Oosterbaan | 6-2,6-2 |
| ITF M25 Weston | 2019/01/30 15:00 | Paul Oosterbaan v Adrian Obert | 6-4,6-4 |
| ITF M25 Weston | 2019/01/29 14:30 | Paul Oosterbaan v Lucas Renard | 4-6,6-1,10-4 |
| ITF M25 Weston | 2019/01/28 14:30 | Paul Oosterbaan v Boris Arias | 6-2,6-4 |
| ITF M25 Palm Coast | 2019/01/25 15:00 | Paul Oosterbaan v Or Ram-Harel | 2-6,1-6 |
| ITF M15 Vale Do Lobo | 2019/02/20 11:00 | Luis Faria v Simon A Ivanov | 6-0,6-4 |
| ITF M15 Monastir | 2019/02/06 10:55 | Gabriel Petit v Simon A Ivanov | 6-3,6-1 |
| ITF M15 Monastir | 2019/02/05 10:30 | Gabriel Petit v Simon A Ivanov | 6-3,6-1 |
| ITF M15 Monastir | 2019/01/30 09:00 | Simon A Ivanov v Valentin Guenther | 5-7,6-1,2-6 |
| ITF Portugal F1 | 2018/02/19 17:00 | Simon A Ivanov v Luis G Monio | 2-6,6-1,3-6 |
| ITF Portugal F1 | 2018/02/19 10:00 | Simon A Ivanov v Yanik Kaelin | 6-3,6-3 |
| ITF Portugal F1 | 2018/02/18 13:00 | Bart Van Den Berg v Simon A Ivanov | 6-4,1-6,1-6 |