Stadium: Court 4 Round: 25 Ground: Clay
| Challenger Guayaquil | 2021/10/31 21:00 | Oliver Crawford v Daniel Dutra Da Silva | 4-6,3-6 |
| ITF M25 Guayaquil | 2021/10/29 15:00 | Oliver Crawford v Murkel Dellien | 6-3,6-4 |
| ITF M25 Guayaquil | 2021/10/28 15:00 | Oliver Crawford v Alvaro Guillen Meza | 6-3,6-2 |
| ITF M25 Guayaquil | 2021/10/26 15:00 | Oliver Crawford v Camilo Benavides Soto | 6-0,6-0 |
| Challenger Santiago | 2021/10/12 15:25 | Oliver Crawford v Felipe Meligeni Rodrigues Alves | 6-7,3-6 |
| Challenger Santiago | 2021/10/11 14:00 | Alexis Galarneau v Oliver Crawford | 3-6,4-6 |
| Challenger Santiago Qual | 2021/10/10 15:30 | Sebastian Santibanez v Oliver Crawford | 1-6,1-6 |
| Challenger Santiago | 2021/10/05 16:40 | Goncalo Oliveira v Oliver Crawford | 6-4,6-2 |
| ATP Umag | 2021/07/18 14:00 | Hamad Medjedovic v Filip Horansky | 4-6,7-6,1-6 |
| ATP Belgrade | 2021/05/24 10:00 | Alex Molcan v Hamad Medjedovic | 6-4,6-3 |
| ITF M15 Prijedor | 2021/05/15 10:00 | Hamad Medjedovic v Nerman Fatic | 7-5,6-7,3-6 |
| ITF M15 Prijedor | 2021/05/14 09:00 | Hamad Medjedovic v Aleksandar Tomas | 6-0,6-3 |
| ITF M15 Prijedor | 2021/05/13 10:05 | Fabian Marozsan v Hamad Medjedovic | 4-6,4-6 |
| Challenger Biella | 2021/05/05 15:00 | Joao Menezes v Hamad Medjedovic | 7-5,2-6,6-4 |
| Challenger Biella | 2021/05/03 10:40 | Hamad Medjedovic v Ruben Bemelmans | 7-5,7-6 |
| ATP Belgrade | 2021/04/19 11:55 | Facundo Bagnis v Hamad Medjedovic | 6-4,6-2 |