Stadium: Court 1 Round: 25 Ground: Clay
| ITF M25 Ueberlingen | 2021/08/17 08:00 | Andres Gabriel Ciurletti v Nikolaj Talimaa | 6-3,6-1 |
| ITF M25 Ueberlingen | 2021/08/16 08:00 | Andres Gabriel Ciurletti v Philip Florig | 7-5,6-3 |
| ITF M25 Marburg | 2021/07/06 12:30 | Andres Gabriel Ciurletti v Yannik Steinegger | 1-6,7-6,3-10 |
| ITF M25 Marburg | 2021/07/05 09:30 | Kirill Kivattsev v Andres Gabriel Ciurletti | 6-7,6-7 |
| ITF M15 Troisdorf | 2021/05/10 11:00 | Andres Gabriel Ciurletti v Timo Stodder | 3-6,2-6 |
| ITF M15 Troisdorf | 2021/05/09 10:00 | Fred Olivier Schommer v Andres Gabriel Ciurletti | 0-6,1-6 |
| ITF M15 Sharm El Sheikh | 2021/04/06 07:30 | Lukas Krainer v Andres Gabriel Ciurletti | 6-3,6-2 |
| ITF M15 Sharm El Sheikh | 2021/04/05 07:30 | Emmanuel Luria v Andres Gabriel Ciurletti | 1-6,2-6 |
| 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 |
| Challenger Little Rock | 2021/06/02 16:30 | Oliver Crawford v Peter Polansky | 7-5,6-2 |
| ITF M25 Pensacola | 2021/05/21 14:25 | Adrian Andreev v Oliver Crawford | 6-2,6-3 |