Stadium: Court 1 Round: 26 Ground: Hardcourt indoor
| ITF M15 East Lansing | 2023/11/15 17:30 | Alafia Ayeni v David Saye | 7-6,7-6 |
| 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 Fé | 2023/10/16 13:00 | Nicolas Mejia v Alafia Ayeni | 6-3,6-2 |
| ITF M15 East Lansing | 2023/11/15 16:35 | Maxwell McKennon v Max Sheldon | 6-1,6-3 |
| ITF M15 East Lansing | 2023/11/14 14:00 | Maxwell McKennon v Holden Koons | 6-4,7-5 |
| ITF M15 East Lansing | 2023/11/13 17:00 | Maxwell McKennon v Ids Waterbolk | 6-1,6-1 |
| ITF M25 Harlingen | 2023/10/26 19:45 | Maxwell McKennon v Karue Sell | 4-6,6-7 |
| ITF M25 Harlingen | 2023/10/25 20:50 | Jerry Roddick v Maxwell McKennon | 3-6,6-7 |
| ITF M15 Albuquerque | 2023/09/25 14:00 | Eugenio G Fitzmaurice v Maxwell McKennon | 1-6,6-3,10-3 |
| ITF M15 Champaign | 2023/09/13 20:25 | William Grant v Maxwell McKennon | 6-4,6-3 |
| ITF M25 Champaign | 2023/09/12 16:40 | Gabriel Evans v Maxwell McKennon | 6-7,6-2,6-10 |