Stadium: Gencom Round: 25 Ground: Clay
| Challenger Barletta | 2021/08/24 14:25 | Andrea Vavassori v Jay Clarke | 6-3,6-4 |
| Challenger Verona | 2021/08/20 16:10 | Nino Serdarusic v Jay Clarke | 6-1,6-1 |
| Challenger Verona | 2021/08/19 15:00 | Jay Clarke v Dmitry Popko | 3-6,6-4,7-5 |
| Challenger Verona | 2021/08/18 09:00 | Jay Clarke v Roberto Quiroz | 6-4,6-4 |
| Challenger Verona | 2021/08/17 09:00 | Jay Clarke v Nicolas Mejia | 6-3,6-4 |
| Challenger San Marino | 2021/08/10 10:30 | Sebastian Baez v Jay Clarke | 6-7,7-5,5-7 |
| Challenger Nur-Sultan | 2021/07/20 09:45 | Jay Clarke v Andrey Kuznetsov | 6-7,4-6 |
| Challenger Nur-Sultan | 2021/07/18 08:00 | Max Purcell v Jay Clarke | 3-6,6-4,7-6 |
| ITF M25 Ueberlingen | 2021/08/18 10:10 | Jeremy Jahn v Alexander Cozbinov | 3-6,7-6,1-6 |
| ITF M25 Bolzano | 2021/08/03 13:50 | Andrea Gola v Jeremy Jahn | 4-6,6-2,6-3 |
| ITF M25 Denia | 2021/07/27 17:25 | Carlos Lopez Montagud v Jeremy Jahn | 6-4,6-2 |
| ITF M25 Gandia | 2021/07/21 16:00 | Jordi Mas De Ugarte v Jeremy Jahn | 6-4,6-3 |
| Challenger Amersfoort | 2021/07/12 09:00 | Jeremy Jahn v Johan Nikles | 2-6,3-6 |
| Challenger Amersfoort | 2021/07/11 11:40 | Jeremy Jahn v Arjun Kadhe | 6-2,6-7,6-4 |
| ITF M25 Marburg | 2021/07/06 16:40 | Alexander Donski v Jeremy Jahn | 6-2,6-2 |
| ITF M25 The Hague | 2021/06/29 09:00 | Jeremy Jahn v Javier Barranco Cosano | 2-6,3-6 |