Stadium: Court 1 Round: 25 Ground: Clay
| Challenger - Savannah | 2024/04/22 20:50 | Ethan Quinn v Oliver Crawford | 6-2,6-4 |
| Challenger - Tallahassee | 2024/04/19 16:00 | Oliver Crawford v Stefan Kozlov | 2-6,2-6 |
| Challenger - Tallahassee | 2024/04/17 17:05 | Hady Habib v Oliver Crawford | 3-6,4-6 |
| Challenger - Tallahassee | 2024/04/16 15:00 | Oliver Crawford v Dmitry Popko | 6-0,7-6 |
| Challenger - Sarasota | 2024/04/08 23:15 | Zizou Bergs v Oliver Crawford | 6-2,6-2 |
| Challenger - Ciudad de Mexico | 2024/04/05 21:45 | Thiago Agustin Tirante v Oliver Crawford | 6-4,6-4 |
| Challenger - Ciudad de Mexico | 2024/04/04 18:00 | Murkel Dellien v Oliver Crawford | 2-6,4-6 |
| Challenger - Ciudad de Mexico | 2024/04/03 00:55 | Ernesto Escobedo v Oliver Crawford | 6-7,4-6 |
| Challenger - Ostrava | 2024/04/23 10:25 | Maks Kasnikowski v Jakub Nicod | 6-1,6-7,1-6 |
| Challenger - Oeiras | 2024/04/15 09:30 | Maks Kasnikowski v Gauthier Onclin | 6-7,3-6 |
| Challenger - Oeiras | 2024/04/14 11:35 | Maks Kasnikowski v Pedro Araujo | 6-7,6-3,6-3 |
| Challenger Split | 2024/04/11 09:00 | Maks Kasnikowski v Matej Dodig | 4-6,4-6 |
| Challenger Split | 2024/04/09 10:00 | Maks Kasnikowski v Zdenek Kolar | 6-1,6-2 |
| Challenger - Barletta | 2024/04/05 09:00 | Harold Mayot v Maks Kasnikowski | 7-5,6-3 |
| Challenger - Barletta | 2024/04/03 12:30 | Maks Kasnikowski v Franco Agamenone | 6-4,7-6 |
| Challenger - Barletta | 2024/04/01 13:30 | Maks Kasnikowski v Giovanni Oradini | 6-4,7-5 |