Stadium: Court 1 Round: 27 Ground: Clay
| ITF M15 Cairo | 2021/05/05 12:45 | Alex Barrena v Oliver Crawford | 0-6,2-6 |
| ITF M25 Rome | 2023/05/31 10:05 | Oliver Crawford v Marcello Serafini | 7-5,7-5 |
| ITF M25 Rome | 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 Pucinelli De Almeida | 6-3,7-6 |
| ITF M25 Kursumlijska Banja | 2023/05/19 10:05 | Marko Topo v Oliver Crawford | 6-3,6-1 |
| ITF M25 Kursumlijska Banja | 2023/05/18 14:00 | Mwendwa Mbithi v Oliver Crawford | 0-6,2-6 |
| ITF M25 Kursumlijska Banja | 2023/05/17 11:15 | Johan A Rodriguez Rodriguez v Oliver Crawford | 3-6,4-6 |
| ITF M25 Rome | 2023/05/31 09:40 | Alex Barrena v Gianmarco Ferrari | 6-1,6-3 |
| ITF M25 Rome | 2023/05/30 16:25 | Alex Barrena v Niccolo Ciavarella | 6-4,6-2 |
| ITF M15 Warmbad-Villach | 2023/05/27 09:00 | Alex Barrena v Tim Handel | 2-6,6-4,6-3 |
| ITF M15 Warmbad-Villach | 2023/05/26 09:00 | Tommaso Compagnucci v Alex Barrena | 3-6,0-6 |
| ITF M15 Warmbad-Villach | 2023/05/25 13:00 | Khumoyun Sultanov v Alex Barrena | 6-7,6-3,2-6 |
| ITF M15 Warmbad-Villach | 2023/05/22 13:15 | Alec Deckers v Alex Barrena | 3-6,1-6 |
| ITF M25 Reggio Emilia | 2023/05/18 17:10 | Giovanni Oradini v Alex Barrena | 6-3,6-3 |
| ITF M25 Reggio Emilia | 2023/05/17 13:50 | Alex Barrena v Luca Potenza | 6-3,6-3 |