Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| ITF - M25 Columbus | 2023/11/14 15:50 | Jacob Fearnley v Robinson Le Meur | 6-2,6-3 |
| ITF - M25 Columbus | 2023/11/13 16:00 | Jacob Fearnley v Mitchell Maroscher | 6-2,6-1 |
| ITF - M25 Glasgow | 2023/10/27 12:00 | Tibo Colson v Jacob Fearnley | 3-6,5-7 |
| ITF - M25 Glasgow | 2023/10/26 13:50 | Milos Karol v Jacob Fearnley | 3-6,3-6 |
| ITF - M25 Glasgow | 2023/10/25 13:20 | Jacob Fearnley v Umberto Maria Giovannini | 6-2,6-0 |
| ITF - M25 Edgbaston | 2023/10/21 09:30 | Kyle Edmund v Jacob Fearnley | 3-6,1-6 |
| ITF - M25 Edgbaston | 2023/10/20 09:00 | Giles Hussey v Jacob Fearnley | 3-6,1-6 |
| ITF - M25 Edgbaston | 2023/10/19 09:00 | Robin Bertrand v Jacob Fearnley | 2-6,1-6 |
| Challenger - Knoxville | 2023/11/07 18:00 | Johannus Monday v Gabriel Debru | 6-4,5-7,3-6 |
| ITF - M15 Las Vegas | 2023/10/19 20:30 | Johannus Monday v Alex Martinez | 6-7,5-7 |
| ITF - M15 Las Vegas | 2023/10/18 19:45 | Trey Hilderbrand v Johannus Monday | 2-6,6-7 |
| Challenger - Tiburon | 2023/10/04 18:00 | Johannus Monday v Alexander Ritschard | 3-6,7-6,6-7 |
| Challenger - Tiburon | 2023/10/02 21:35 | Laurent Lokoli v Johannus Monday | 6-7,2-6 |
| Challenger - Istanbul | 2023/09/06 10:25 | Johannus Monday v Jesper De Jong | 5-7,1-6 |
| Challenger - Istanbul | 2023/09/04 11:30 | Johannus Monday v Kacper Zuk | 4-6,6-1,6-4 |
| Challenger - Mallorca | 2023/08/29 12:00 | Marco Trungelliti v Johannus Monday | 6-4,6-4 |