Stadium: Court 10 Round: 54 Ground: Clay
| Koszalin, Singles Qualifying M-ITF-POL-02A | 2019/08/05 08:00 | Vanwolleghem, Raynaud v Daniil Savelev | 1-6,4-6 |
| Brussels, Singles M-ITF-BEL-03A | 2019/07/29 12:45 | Daniel De Jonge v Vanwolleghem, Raynaud | 6-2,6-4 |
| ITF Belgium F8 | 2018/08/12 09:00 | Vanwolleghem, Raynaud v Recek, Dominik | 1-6,0-6 |
| ITF Belgium F8 | 2018/08/11 08:00 | Bistre, Carlos v Vanwolleghem, Raynaud | 0-6,0-6 |
| ITF Germany F11 | 2018/08/05 08:00 | Pero, Anthony v Vanwolleghem, Raynaud | 6-1,6-3 |
| Koksijde, Singles M-ITF-BEL-04A | 2019/08/12 08:00 | Soderlund, Carl v Freire Da Silva, Nathan | 6-1,6-2 |
| ITF M15 Eupen | 2019/08/05 09:00 | Freire Da Silva, Nathan v Bruna, Esteban | 3-6,5-7 |
| ITF M15 Telavi | 2019/07/29 06:00 | Kolasinski, Filip v Freire Da Silva, Nathan | 6-1,6-3 |
| ITF M15 Telavi | 2019/07/22 08:00 | Freire Da Silva, Nathan v Gorodynskyi, Vladyslav | 2-6,4-6 |
| ITF M25 Bourg-en-Bresse | 2019/07/01 10:30 | Adan Freire Da Silva v Freire Da Silva, Nathan | 7-5,6-2 |
| ITF - M15 Tbilisi | 2019/04/30 06:00 | Alexandros Skorilas v Freire Da Silva, Nathan | 6-3,6-3 |
| ITF - M15 Tbilisi | 2019/04/29 06:00 | Soghoyan, Artur v Freire Da Silva, Nathan | 2-6,4-6 |
| ITF - M15 Poitiers | 2019/03/11 09:40 | Pontico, Hugo v Freire Da Silva, Nathan | 6-3,6-4 |