Stadium: Atlantic Radiology Court Round: 25 Ground: Clay
| Challenger Morelos | 2023/04/19 22:00 | James Duckworth v Oliver Crawford | 3-6,7-6,6-2 |
| Challenger Morelos | 2023/04/18 00:50 | Nicolas Mejia v Oliver Crawford | 6-7,6-3,3-6 |
| Challenger Leon | 2023/04/12 18:00 | Oliver Crawford v Nicolas Mejia | 6-7,6-7 |
| Challenger Leon | 2023/04/10 22:40 | Oliver Crawford v Joao Lucas Reis da Silva | 6-3,3-6,6-3 |
| ITF M25 Mysuru | 2023/04/01 04:00 | Blake Ellis v Oliver Crawford | 7-5,6-3 |
| ITF M25 Mysuru | 2023/03/31 06:45 | Florent Bax v Oliver Crawford | 4-6,0-6 |
| ITF M25 Mysuru | 2023/03/30 04:15 | Ishaque Eqbal v Oliver Crawford | 3-6,3-6 |
| ITF M25 Mysuru | 2023/03/29 04:00 | Manish Ganesh v Oliver Crawford | 1-6,3-6 |
| Challenger Tallahassee | 2023/04/19 18:00 | Facundo Diaz Acosta v Moez Echargui | 6-7,5-7 |
| Challenger Tallahassee | 2023/04/17 22:00 | Facundo Diaz Acosta v Bjorn Fratangelo | 6-3,6-4 |
| Challenger Sarasota | 2023/04/11 17:00 | Facundo Diaz Acosta v Gabriel Diallo | 6-3,2-6,6-7 |
| ATP Houston | 2023/04/02 18:45 | Yannick Hanfmann v Facundo Diaz Acosta | 7-5,6-2 |
| ATP Houston | 2023/04/01 21:10 | Seong Chan Hong v Facundo Diaz Acosta | 2-6,3-6 |
| Challenger Santiago | 2023/03/11 14:00 | Facundo Diaz Acosta v Thiago Seyboth Wild | 6-7,3-6 |
| Challenger Santiago | 2023/03/10 14:00 | Luciano Darderi v Facundo Diaz Acosta | 0-6,5-7 |
| Challenger Santiago | 2023/03/08 17:10 | Hugo Gaston v Facundo Diaz Acosta | 5-7,3-6 |