Stadium: Court 4 Round: 62 Ground: Clay
| UTR Pro Olomouc | 2023/07/09 06:00 | Maxwell Benson v Peter Sallay | 2-6,6-3,5-7 |
| UTR Pro Olomouc | 2023/07/08 06:00 | Maxwell Benson v Martin Facundo Carrizo | 6-2,6-1 |
| UTR Pro Olomouc | 2023/07/07 06:00 | Jonasz Dziopak v Maxwell Benson | 3-6,1-6 |
| UTR Pro Olomouc | 2023/07/06 10:45 | Alessandro-D Ventre v Maxwell Benson | 6-3,1-6,5-0 |
| UTR Pro Olomouc | 2023/07/04 08:43 | Jan Jermar v Maxwell Benson | 6-2,6-3 |
| UTR Pro Olomouc | 2023/07/03 06:48 | Maxwell Benson v Robert Rumler | 5-7,6-7 |
| UTR Pro Tennis Series Winston-Salem | 2022/09/10 16:48 | Menelaos Efstathiou v Maxwell Benson | 7-5,7-5 |
| UTR Pro Tennis Series Winston-Salem | 2022/09/09 18:26 | Maxwell Benson v Eder B F De Leceta | 6-4,2-6,6-2 |
| ITF M25 Koksijde | 2023/08/13 08:00 | Jim Hendrikx v Louis Larue | 4-6,3-6 |
| ITF M15 Eupen | 2023/08/09 15:35 | Axel Garcian v Jim Hendrikx | 6-3,6-4 |
| ITF M15 Eupen | 2023/08/08 17:45 | Julien Evrard v Jim Hendrikx | 6-3,5-7,1-10 |
| ITF M15 Eupen | 2023/08/08 11:00 | Jim Hendrikx v Konstantin Cucka | 6-3,6-2 |
| ITF M15 Eupen | 2023/08/07 13:00 | Sebastian Rafael Sotelo v Jim Hendrikx | 7-6,2-6,7-10 |
| ITF M15 Eindhoven | 2023/07/31 08:00 | Roland Stuurman v Jim Hendrikx | 6-3,6-1 |
| ITF M25 Esch/Alzette | 2023/07/17 08:35 | Lodewijk Weststrate v Jim Hendrikx | 6-0,6-4 |
| ITF M25 Esch/Alzette Qual | 2023/07/16 08:00 | Jim Hendrikx v Tim Pauly | 6-4,6-0 |