Stadium: VOLKSBANK Court Round: 25 Ground: Clay
| ITF M25 Frankfurt am Main | 2021/08/13 09:50 | Mariano Kestelboim v Yshai Oliel | 2-6,2-6 |
| ITF M25 Frankfurt am Main | 2021/08/12 11:10 | Taiyo Yamanaka v Mariano Kestelboim | 2-6,2-6 |
| ITF M25 Frankfurt am Main | 2021/08/10 13:15 | Mariano Kestelboim v Valentin Royer | 6-4,7-6 |
| ITF M25 Wetzlar | 2021/08/04 08:00 | Mariano Kestelboim v Mats Rosenkranz | 5-7,2-6 |
| ITF M25 Gandia | 2021/07/24 15:00 | Antoine Escoffier v Mariano Kestelboim | 5-7,6-4,6-2 |
| ITF M25 Gandia | 2021/07/23 08:00 | Facundo Juarez v Mariano Kestelboim | 4-6,6-4,2-6 |
| ITF M25 Gandia | 2021/07/21 07:30 | Imanol L Morillo v Mariano Kestelboim | 7-5,3-6,4-6 |
| ITF M15 Poprad | 2021/07/06 09:35 | Mariano Kestelboim v Marco Miceli | 6-1,3-6,2-6 |
| 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 |