Stadium: Court 6 Round: 25 Ground: Hardcourt outdoor
| ITF - Faro M15 | 2019/02/27 13:00 | Paul Oosterbaan v Simon A Ivanov | 1-6,6-1,6-1 |
| ITF - Loule M15 | 2019/03/06 19:00 | Manuel Pena Lopez v Simon A Ivanov | 1-6,6-2,6-4 |
| ITF - Faro M15 | 2019/02/27 13:00 | Paul Oosterbaan v Simon A Ivanov | 1-6,6-1,6-1 |
| ITF - Vale Do Lobo M15 | 2019/02/20 11:00 | Luis Faria v Simon A Ivanov | 6-0,6-4 |
| ITF - Monastir M15 | 2019/02/06 10:55 | Gabriel Petit v Simon A Ivanov | 6-3,6-1 |
| ITF - Monastir M15 | 2019/02/05 10:30 | Gabriel Petit v Simon A Ivanov | 6-3,6-1 |
| ITF - Monastir M15 | 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 - Loule M15 | 2019/03/07 15:30 | Sandro Ehrat v Paul Oosterbaan | 6-1,6-3 |
| ITF - Loule M15 | 2019/03/07 11:25 | Eduardo Struvay v Paul Oosterbaan | 5-7,6-1,3-6 |
| ITF - Faro M15 | 2019/02/28 13:15 | Jacob Grills v Paul Oosterbaan | 4-6,6-3,6-1 |
| ITF - Faro M15 | 2019/02/27 13:00 | Paul Oosterbaan v Simon A Ivanov | 1-6,6-1,6-1 |
| ITF - Faro M15 | 2019/02/26 11:55 | Laurent Lokoli v Paul Oosterbaan | 5-7,3-6 |
| ITF - Faro M15 | 2019/02/25 10:00 | Yshai Oliel v Paul Oosterbaan | 6-7,3-6 |
| ITF - Vale Do Lobo M15 | 2019/02/19 13:00 | Paul Oosterbaan v Finn Tearney | 4-6,5-7 |
| ITF - Weston M25 | 2019/01/31 18:00 | Dmitry Popko v Paul Oosterbaan | 6-2,6-2 |