Stadium: Central Round: 25 Ground: Clay
| ITF M25 Rooma | 2023/06/01 09:00 | Oliver Crawford v Alex Barrena | 6-0,2-6,1-6 |
| ITF M25 Rooma | 2023/05/31 10:05 | Oliver Crawford v Marcello Serafini | 7-5,7-5 |
| ITF M25 Rooma | 2023/05/30 13:35 | Oliver Crawford v Giammarco Gandolfi | 6-0,6-3 |
| Challenger Skopje | 2023/05/25 09:30 | Francisco Comesana v Oliver Crawford | 6-4,6-1 |
| Challenger Skopje | 2023/05/24 09:00 | Max Houkes v Oliver Crawford | 4-6,2-6 |
| Challenger Skopje | 2023/05/23 08:30 | Oliver Crawford v Matheus P De Almeida | 6-3,7-6 |
| ITF M25 Kuršumlijska Banja | 2023/05/19 10:05 | Marko Topo v Oliver Crawford | 6-3,6-1 |
| ITF M25 Kuršumlijska Banja | 2023/05/18 14:00 | Mwendwa Mbithi v Oliver Crawford | 0-6,2-6 |
| ITF M25 Martos | 2023/06/15 15:00 | John Echeverria v Imanol L Morillo | 6-4,6-4 |
| ITF M25 Martos | 2023/06/14 08:30 | Imanol L Morillo v Robin Bertrand | 6-1,6-7,7-6 |
| ITF M25 Gurb | 2023/05/17 12:25 | Imanol L Morillo v Alejandro Juan Mano | 1-6,3-6 |
| ITF M15 Telde | 2023/04/18 08:00 | Gabriele Pennaforti v Imanol L Morillo | 5-7,6-3,6-4 |
| ITF M15 Telde | 2023/04/12 12:55 | Imanol L Morillo v Michael Zhu | 1-6,4-6 |
| ITF M25 Reus | 2023/04/07 08:00 | Imanol L Morillo v Vilius Gaubas | 4-6,6-4,3-6 |
| ITF M25 Reus | 2023/04/06 09:00 | Rrezart Cungu v Imanol L Morillo | 6-4,2-6,2-6 |
| ITF M25 Reus | 2023/04/04 12:00 | Ignacio Buse v Imanol L Morillo | 1-6,1-6 |