Stadium: Court 2 Round: 25 Ground: Clay
| Challenger Modena | 2023/06/27 13:45 | Oliver Crawford v Moez Echargui | 4-6,5-7 |
| ITF M25 Mungia | 2023/06/22 15:25 | Oliver Crawford v Henrique Rocha | 1-6,7-6,2-6 |
| ITF M25 Mungia | 2023/06/21 16:10 | Oliver Crawford v Matyas Fuele | 6-4,6-3 |
| ITF M25 Mungia | 2023/06/20 11:25 | Oliver Crawford v Imanol L Morillo | 6-3,6-4 |
| ITF M25 Rome | 2023/06/01 09:00 | Oliver Crawford v Alex Barrena | 6-0,2-6,1-6 |
| ITF M25 Rome | 2023/05/31 10:05 | Oliver Crawford v Marcello Serafini | 7-5,7-5 |
| ITF M25 Rome | 2023/05/30 13:35 | Oliver Crawford v Giammarco Gandolfi | 6-0,6-3 |
| Challenger Skopje | 2023/05/25 09:30 | Francisco Comesana v Oliver Crawford | 6-4,6-1 |
| ITF M25 Klosters | 2023/07/02 09:45 | Yunis, Facundo v von Der Schulenburg, Henry | 3-6,4-6 |
| Zug, Switzerland | 2022/07/24 12:55 | von Der Schulenburg, Henry v Edoardo Lavagno | 1-6,2-6 |
| ITF M25 Klosters | 2021/06/25 10:05 | von Der Schulenburg, Henry v Jakub Paul | 6-7,2-6 |
| ITF M25 Klosters | 2021/06/24 06:50 | Leandro Riedi v von Der Schulenburg, Henry | 4-6,2-6 |
| ITF M25 Klosters | 2021/06/22 08:30 | Martin Damm v von Der Schulenburg, Henry | 4-6,4-6 |
| ITF M25 Klosters | 2021/06/21 07:00 | von Der Schulenburg, Henry v Lukas Palovic | 6-1,6-3 |
| ITF M25 Klosters | 2021/06/20 06:55 | Ugo Blanchet v von Der Schulenburg, Henry | 2-6,6-4,6-10 |
| ITF M25 Klosters | 2020/09/16 07:00 | von Der Schulenburg, Henry v Jelle Sels | 4-6,3-6 |