Stadium: Cancha 3 Ground: Clay
| Challenger Santiago | 2021/10/03 14:00 | Oliver Crawford v Daniel Antonio Nunez | 7-5,6-2 |
| ITF M25 Sierre | 2021/09/05 08:50 | Rinky Hijikata v Oliver Crawford | 7-6,6-1 |
| ITF M25 Sierre | 2021/09/04 10:20 | Patrick Kypson v Oliver Crawford | 3-6,4-6 |
| ITF M25 Sierre | 2021/09/03 10:00 | Valentin Vacherot v Oliver Crawford | 3-6,6-7 |
| ITF M25 Sierre | 2021/09/02 12:45 | Mirko Martinez v Oliver Crawford | 1-6,2-6 |
| ITF M25 Sierre | 2021/09/01 13:40 | Louroi Martinez v Oliver Crawford | 3-6,4-6 |
| ITF M25 Trier | 2021/08/25 15:00 | Henri Squire v Oliver Crawford | 3-6,6-1,6-2 |
| ITF M25 Ueberlingen | 2021/08/20 10:00 | Ergi Kirkin v Oliver Crawford | 6-4,3-6,6-2 |
| Challenger Santiago | 2021/10/03 19:55 | Jonathan Mridha v Evan King | 6-3,3-6,6-0 |
| Challenger Murcia | 2021/09/27 09:00 | Emilio Nava v Jonathan Mridha | 6-4,7-5 |
| Challenger Murcia | 2021/09/26 10:40 | Manish Sureshkumar v Jonathan Mridha | 6-7,4-6 |
| ITF M25 Jonkoping | 2021/09/22 12:10 | Jonathan Mridha v Viktor Durasovic | 4-6,2-6 |
| ITF M25 Jonkoping | 2021/09/21 09:10 | Jonathan Mridha v Simon Freund | 7-5,4-6,7-5 |
| Challenger Banja Luka | 2021/09/08 15:30 | Andrej Martin v Jonathan Mridha | 6-3,7-5 |
| Challenger Banja Luka | 2021/09/07 09:55 | Jonathan Mridha v Dominic Stephan Stricker | 6-2,6-3 |
| Challenger Banja Luka | 2021/09/06 09:00 | Elmar Ejupovic v Jonathan Mridha | 6-2,2-6,2-6 |