Ground: Hardcourt indoor
| UTR Pro Winston-Salem | 2023/11/27 22:30 | Jamieson Nathan v Holden Koons | 2-6,0-6 |
| UTR Pro Winston-Salem | 2023/11/26 20:08 | Holden Koons v William Manning | 6-2,6-2 |
| UTR Pro Winston-Salem | 2023/11/26 18:30 | Holden Koons v Dylan Chang | 0-0 |
| 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 | Holden Koons v Stepan Mruzek | 6-4,6-2 |
| ITF M15 Winston-Salem | 2023/11/09 19:00 | Holden Koons v Dhakshineswar Suresh | 5-7,4-6 |
| ITF M15 Winston-Salem | 2023/11/08 19:30 | Jeremy Jin v Holden Koons | 4-6,2-6 |
| UTR Pro Winston-Salem | 2023/09/09 22:30 | Franco Capalbo v Holden Koons | 5-7,7-6,5-2 |
| UTR Pro Winston-Salem | 2023/11/30 18:30 | Harry Thursfield v Nicholas Mangiapane | 6-3,6-2 |
| UTR Pro Winston-Salem | 2023/11/28 22:30 | Harry Thursfield v Obrad Markovski | 6-3,6-4 |
| UTR Pro Winston-Salem | 2023/11/27 21:00 | Harry Thursfield v Matthew Thompson | 4-6,4-6 |
| UTR Pro Winston-Salem | 2023/11/26 20:00 | Nikola Parichkov v Harry Thursfield | 2-6,4-6 |
| ITF M25 Vale Do Lobo | 2023/11/22 10:00 | Harry Thursfield v Rodrigo Fernandes | 4-6,0-6 |
| ITF M25 Vale Do Lobo | 2023/11/21 10:00 | Elio Jose Ribeiro Lago v Harry Thursfield | 3-6,2-6 |
| ITF M25 Vale Do Lobo | 2023/11/13 11:00 | Francisco Rocha v Harry Thursfield | 7-6,6-3 |
| ITF M15 Winston-Salem | 2023/11/08 21:15 | Braden Shick v Harry Thursfield | 7-5,6-2 |