Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Calgary | 2023/11/06 18:20 | Alafia Ayeni v Enzo Wallart | 3-6,4-6 |
| Challenger Calgary | 2023/11/05 17:55 | Alafia Ayeni v Collin Altamirano | 7-6,6-4 |
| Challenger Charlottesville | 2023/10/31 19:25 | Aidan Mayo v Alafia Ayeni | 7-5,6-2 |
| Challenger Charlottesville | 2023/10/30 14:00 | Evgeny Karlovskiy v Alafia Ayeni | 6-7,4-6 |
| Challenger Charlottesville | 2023/10/29 16:55 | Alafia Ayeni v Ezekiel Clark | 6-4,6-3 |
| Challenger Curitiba | 2023/10/22 19:20 | Arklon H D Pino v Alafia Ayeni | 7-5,6-4 |
| Challenger Santa Fe | 2023/10/16 13:00 | Nicolas Mejia v Alafia Ayeni | 6-3,6-2 |
| Challenger Santa Fe | 2023/10/15 15:00 | Alafia Ayeni v Matias Franco Descotte | 6-2,2-6,6-4 |
| ITF M15 Santo Domingo | 2023/11/11 13:00 | Facundo Mena v David Saye | 6-4,6-2 |
| ITF M15 Santo Domingo | 2023/11/10 13:00 | David Saye v Mwendwa Mbithi | 6-2,6-1 |
| ITF M25 Santo Domingo | 2023/11/07 13:00 | David Saye v Linus Videhult | 6-4,6-3 |
| ITF M25 Santo Domingo | 2023/11/06 13:30 | David Saye v Matteo Covato | 6-2,6-0 |
| ITF M25 Saint-Augustin | 2023/10/26 01:10 | Mohamed Aziz Dougaz v David Saye | 3-6,6-3,6-3 |
| ITF M25 Saint-Augustin | 2023/10/24 14:00 | David Saye v Niels P Van Noord | 6-3,6-4 |
| ITF M25 Saint-Augustin | 2023/10/23 13:55 | David Saye v Alexandre Bergeron | 6-4,6-3 |
| ITF M25 Las Vegas | 2023/10/16 13:00 | Patrick Maloney v David Saye | 7-5,6-3 |