Stadium: Court 1 Round: 25 Ground: Clay
| ITF - M25 Sunderland | 2019/04/09 10:25 | Zizou Bergs v Ryan Nijboer | 6-2,4-6,6-1 |
| Bolton, Qualifications Simples M-ITF-GBR-03A | 2019/04/04 09:00 | Ryan Nijboer v Lenz, Julian | 3-6,6-7 |
| Bolton, Qualifications Simples M-ITF-GBR-03A | 2019/04/03 09:00 | George Houghton v Ryan Nijboer | 7-6,6-7,0-6 |
| ITF - M15 Sharm El Sheikh | 2019/02/27 12:00 | Pedro Vives Marcos v Ryan Nijboer | 7-6,2-6,7-6 |
| ITF - M15 Sharm El Sheikh | 2019/02/22 08:00 | Bergevi, Filip v Ryan Nijboer | 3-6,6-4,7-6 |
| ITF - M15 Sharm El Sheikh | 2019/02/19 08:00 | Ryan Nijboer v Velotti, Agustin | 4-6,7-5,6-4 |
| ATP - Rotterdam | 2019/02/10 12:10 | Ryan Nijboer v Skugor, Franko | 6-4,2-6,4-6 |
| ATP - Rotterdam | 2019/02/09 14:25 | Jan-Lennard Struff v Ryan Nijboer | 4-6,4-6 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/28 07:00 | Oleg Prihodko v Naoki Tajima | 6-0,6-1 |
| Irpin, Singles Qualifying M-ITF-UKR-04A | 2019/05/21 12:40 | Nikita Mashtakov v Naoki Tajima | 6-0,7-6 |
| ITF M15 Valldoreix | 2019/05/14 13:15 | Oriol Roca Batalla v Naoki Tajima | 6-1,6-4 |
| ITF M15 Grasse | 2019/05/04 14:20 | Naoki Tajima v Hamou, Maxime | 3-6,3-6 |
| ITF M15 Grasse | 2019/05/03 10:35 | Naoki Tajima v Kirill Kivattsev | 6-7,6-4,7-6 |
| ITF M15 Grasse | 2019/05/02 13:45 | Naoki Tajima v Broville, Maxence | 6-2,6-2 |
| ITF M15 Grasse | 2019/04/30 15:10 | Tchoutakian, Maxime v Naoki Tajima | 4-6,4-6 |
| Matsuyama, Singles M-ITF-JPN-06A | 2019/04/12 05:20 | Naoki Tajima v Sekiguchi, Shuichi | 4-6,4-6 |