Stadium: Court 12 Round: 19 Ground: Clay
| Challenger Antalya | 2021/11/29 10:05 | Khumoyun Sultanov v Jakub Paul | 3-6,3-6 |
| Challenger Tenerife | 2021/10/31 13:10 | Jakub Paul v Miguel Damas | 2-6,6-2,2-6 |
| ITF M25 Hamburg | 2021/10/24 10:00 | Henri Squire v Jakub Paul | 4-6,2-6 |
| ITF M25 Hamburg | 2021/10/23 11:50 | Louis Wessels v Jakub Paul | 2-6,4-6 |
| ITF M25 Hamburg | 2021/10/22 10:00 | Jakub Paul v Leandro Riedi | 7-5,6-4 |
| ITF M25 Hamburg | 2021/10/21 15:50 | Elmar Ejupovic v Jakub Paul | 6-2,2-6,2-6 |
| ITF M25 Hamburg | 2021/10/19 12:45 | Jakub Paul v Filip Bergevi | 6-4,6-3 |
| ITF M25 Prague | 2021/10/07 10:15 | Jakub Paul v Marek Gengel | 2-6,4-6 |
| Challenger Antalya | 2021/11/29 08:55 | Tiago Cacao v Lucas Gerch | 6-1,3-6,6-2 |
| ITF M15 Antalya | 2021/11/24 06:30 | Tiago Cacao v Cezar Cretu | 5-7,3-6 |
| ITF M25 Portimao | 2021/10/27 11:20 | Vladyslav Orlov v Tiago Cacao | 6-3,6-1 |
| ITF M25 Quinta Do Lago | 2021/10/20 12:35 | Tiago Cacao v Arthur Cazaux | 6-7,2-6 |
| ITF M25 Loule | 2021/10/12 13:00 | Tiago Cacao v Luis Faria | 3-6,6-4,0-6 |
| ITF M25 Setubal | 2021/10/06 12:20 | Tiago Cacao v Maximilian Neuchrist | 6-7,0-6 |
| Challenger Lisbon | 2021/09/28 15:55 | Joao Domingues v Tiago Cacao | 6-4,6-4 |
| Challenger Braga | 2021/09/22 12:00 | Thiago Monteiro v Tiago Cacao | 6-1,6-1 |