Stadium: Court 1 Round: 27 Ground: Clay
| ITF - Ueberlingen M25 | 2021/08/19 12:30 | Ergi Kirkin v Leopold Zima | 5-7,6-0,6-3 |
| ITF - Ueberlingen M25 | 2021/08/17 14:50 | Ergi Kirkin v Manfred Fellin | 1-6,6-0,6-2 |
| ITF - Parnu M15 | 2021/08/08 08:00 | Ergi Kirkin v Mattias Siimar | 5-7,6-3,6-3 |
| ITF - Parnu M15 | 2021/08/07 09:30 | Ergi Kirkin v Simone Roncalli | 6-1,6-2 |
| ITF - Parnu M15 | 2021/08/06 08:00 | Ergi Kirkin v Luke Johnson | 6-2,6-1 |
| ITF - Parnu M15 | 2021/08/05 10:30 | Ergi Kirkin v Alexander Kotzen | 7-6,6-4 |
| ITF - Parnu M15 | 2021/08/04 08:35 | Ergi Kirkin v Oscar Weightman | 6-2,4-6,7-5 |
| ITF - Vejle M15 | 2021/08/01 10:20 | Ergi Kirkin v August Holmgren | 7-6,6-4 |
| ITF - Ueberlingen M25 | 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 - Tulsa M25 | 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 |