Stadium: CC Round: 25 Ground: Clay
| ITF - M25 Ueberlingen | 2021/08/22 12:00 | Ergi Kirkin v Henri Squire | 6-3,4-6,6-4 |
| ITF - M25 Ueberlingen | 2021/08/20 14:45 | Louis Wessels v Henri Squire | 4-6,6-2,4-6 |
| ITF - M25 Ueberlingen | 2021/08/19 08:00 | Henri Squire v Oriol Roca Batalla | 6-7,6-4,6-3 |
| ITF - M25 Ueberlingen | 2021/08/18 08:00 | Henri Squire v Max Wiskandt | 6-4,6-3 |
| ITF - M25 Ueberlingen | 2021/08/17 08:00 | Henri Squire v Nick Dufner | 6-1,6-0 |
| ITF - M25 Wetzlar | 2021/08/06 10:55 | David Pichler v Henri Squire | 4-6,6-4,6-4 |
| ITF - M25 Wetzlar | 2021/08/05 09:00 | Tim Handel v Henri Squire | 6-3,3-6,6-7 |
| ITF - M25 Wetzlar | 2021/08/03 16:10 | Henri Squire v Benjamin Hassan | 6-2,6-3 |
| ITF - M25 Ueberlingen | 2021/08/20 10:00 | Ergi Kirkin v Oliver Crawford | 6-4,3-6,6-2 |
| ITF - M25 Ueberlingen | 2021/08/19 11:45 | Aliaksandr Bulitski v Oliver Crawford | 1-6,1-6 |
| Challenger - Lexington | 2021/07/26 18:00 | Darian King v Oliver Crawford | 6-4,6-1 |
| Challenger - Lexington | 2021/07/25 15:00 | Oliver Crawford v Aleksandar Kovacevic | 7-6,7-5 |
| Challenger - Cary | 2021/07/18 15:00 | Oliver Crawford v Trent Bryde | 6-7,2-6 |
| ITF - M25 Tulsa | 2021/06/17 00:35 | Oliver Crawford v Ryan Shane | 7-5,7-6 |
| Challenger - Orlando | 2021/06/08 17:00 | Oliver Crawford v Emilio Gomez | 6-7,7-6,3-6 |
| Challenger - Little Rock | 2021/06/03 17:00 | Dayne Kelly v Oliver Crawford | 4-6,1-6 |