Stadium: Court 4 Round: 25 Ground: Hardcourt indoor
| Challenger Oeiras | 2023/12/31 11:00 | Daniil Glinka v Cannon Kingsley | 6-3,2-6,7-5 |
| Challenger Drummondville | 2023/11/14 16:40 | Cannon Kingsley v James Duckworth | 5-7,7-6,6-7 |
| Challenger Knoxville | 2023/11/07 21:40 | Sebastian Fanselow v Cannon Kingsley | 6-4,6-2 |
| Challenger Knoxville | 2023/11/06 18:00 | Cannon Kingsley v Gabi Adrian Boitan | 7-5,6-3 |
| Challenger Knoxville | 2023/11/05 22:15 | Cannon Kingsley v Alex Lawson | 6-4,7-6 |
| Challenger Charlottesville | 2023/11/01 19:40 | Brandon Holt v Cannon Kingsley | 6-4,6-4 |
| Challenger Charlottesville | 2023/10/31 18:45 | Cannon Kingsley v Alex Michelsen | 7-5,6-3 |
| Challenger Fairfield | 2023/10/08 18:45 | Learner Tien v Cannon Kingsley | 6-4,6-4 |
| ITF M15 Heraklion | 2023/11/16 10:55 | Younes Lalami Laaroussi v Gianmarco Ferrari | 4-6,6-3,6-1 |
| ITF M15 Heraklion | 2023/11/15 10:50 | Lior Goldenberg v Gianmarco Ferrari | 5-7,2-6 |
| ITF M25 Sunderland | 2023/10/31 15:05 | Sean Hodkin v Gianmarco Ferrari | 7-6,7-6 |
| ITF M25 Glasgow | 2023/10/25 12:55 | Gianmarco Ferrari v Marvin Moeller | 4-6,3-6 |
| ITF M25 Santa Margherita | 2023/10/10 10:15 | Gian Marco Ortenzi v Gianmarco Ferrari | 6-2,3-6,7-5 |
| ITF M25 Santa Margherita | 2023/10/06 09:00 | Gianmarco Ferrari v Nikolas Sanchez Izquierdo | 6-4,4-6,2-6 |
| ITF M25 Santa Margherita | 2023/10/05 11:30 | Gianmarco Ferrari v Giuseppe La Vela | 6-0,6-3 |
| ITF M25 Santa Margherita | 2023/10/04 10:20 | Gianmarco Ferrari v Gian M Di Natale | 6-2,6-2 |