| UTR Pro Winston-Salem | 2023/11/27 18:00 | Alan Jesudason v Meecah Bigun | 5-7,3-6 |
| UTR Pro Winston-Salem | 2023/11/26 21:30 | Franco Capalbo v Alan Jesudason | 0-4 |
| UTR Pro Winston-Salem | 2023/09/08 15:30 | Keegan Smith v Alan Jesudason | 7-6,6-3 |
| UTR Pro Winston-Salem | 2023/09/07 21:23 | Osgar O'Hoisin v Alan Jesudason | 6-1,5-7,6-7 |
| UTR Pro Winston-Salem | 2023/09/06 22:00 | Damien Salvestre v Alan Jesudason | 6-3,4-6,3-6 |
| UTR Pro Winston-Salem | 2023/09/05 22:00 | Harry Thursfield v Alan Jesudason | 2-6,6-1,3-6 |
| UTR Pro Winston-Salem | 2023/09/03 23:30 | Franco Capalbo v Alan Jesudason | 6-3,6-4 |
| UTR Pro Texas | 2023/08/27 13:00 | Ethan Silva v Alan Jesudason | 2-2 |
| UTR Pro Winston-Salem | 2023/11/26 21:30 | Thomas Brown v Maxwell Benson | 6-2,6-0 |
| ITF M25 Saint-Augustin | 2023/10/24 13:55 | Maxwell Benson v Alex Finkelstein | 6-4,4-6,2-10 |
| ITF M25 Pazardzhik | 2023/10/02 13:15 | Plamen Milushev v Maxwell Benson | 6-4,7-5 |
| ITF M25 Pazardzhik | 2023/10/02 07:30 | Anthony Shumsky v Maxwell Benson | 2-6,3-6 |
| ITF M25 Pazardzhik | 2023/09/27 12:35 | Nikola Kolyachev v Maxwell Benson | 6-4,7-6 |
| ITF M25 Pazardzhik | 2023/09/25 13:55 | Maxwell Benson v Felipe Mikkelsen | 7-6,6-4 |
| ITF M25 Pazardzhik | 2023/09/25 07:00 | Vojtech Vlkovsky v Maxwell Benson | 3-6,0-6 |
| ITF M25 Pardubice | 2023/09/18 10:30 | Tom Schonenberg v Maxwell Benson | 6-1,6-2 |