Stadium: Stadium 2 Round: 14 Ground: Hardcourt outdoor
| Challenger Cary | 2021/07/18 15:00 | Liam Draxl v Ryan Harrison | 3-6,7-6,6-7 |
| ATP Newport | 2021/07/12 16:00 | Alex Bolt v Ryan Harrison | 6-0,6-7,7-5 |
| ATP Newport | 2021/07/11 16:45 | Ryan Harrison v Christopher Eubanks | 7-6,6-7,7-6 |
| ITF M15 Weston | 2021/07/04 15:00 | Ryan Harrison v Stefan Kozlov | 7-5,3-6,3-6 |
| ITF M15 Weston | 2021/07/03 18:00 | Gerardo L Villasenor v Ryan Harrison | 1-6,4-6 |
| ITF M15 Weston | 2021/07/02 21:10 | Ryan Harrison v Nicolas Mejia | 6-3,6-4 |
| ITF M15 Weston | 2021/07/01 13:00 | Ryan Harrison v Tom Jomby | 6-2,6-2 |
| Challenger Orlando | 2021/06/06 14:00 | Ryan Harrison v Nick Chappell | 2-6,6-7 |
| Challenger Nur-Sultan | 2021/07/20 07:10 | Pavel Kotov v Edan Leshem | 3-6,6-1,6-4 |
| Challenger Nur-Sultan | 2021/07/19 05:45 | Edan Leshem v Sanjar Fayziev | 6-2,6-4 |
| Challenger Nur-Sultan Qual | 2021/07/18 04:00 | Edan Leshem v Daniil Golubev | 6-0,6-1 |
| Challenger Nur-Sultan | 2021/07/12 04:00 | Edan Leshem v Artem Dubrivnyy | 6-7,6-7 |
| Challenger Nur-Sultan | 2021/07/11 04:00 | Edan Leshem v Alexander Igoshin | 6-2,6-3 |
| ITF M25 Nur-Sultan | 2021/07/08 07:35 | Edan Leshem v Yshai Oliel | 6-7,2-6 |
| ITF M25 Nur-Sultan | 2021/07/07 11:35 | Edan Leshem v Ivan Zaytsev | 6-2,6-2 |
| Challenger Orlando | 2021/06/06 14:00 | Nicolas Mejia v Edan Leshem | 7-6,6-3 |