Stadium: Central Round: 27 Ground: Clay
| ITF M25 Mungia | 2023/06/21 16:10 | Oliver Crawford v Matyas Fuele | 6-4,6-3 |
| ITF M25 Mungia | 2023/06/20 11:25 | Oliver Crawford v Imanol L Morillo | 6-3,6-4 |
| ITF M25 Rome | 2023/06/01 09:00 | Oliver Crawford v Alex Barrena | 6-0,2-6,1-6 |
| 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 P De Almeida | 6-3,7-6 |
| ITF M25 Mungia | 2023/06/21 12:25 | Fajing Sun v Henrique Rocha | 6-3,4-6,4-6 |
| ITF M25 Mungia | 2023/06/19 16:45 | Martin Landaluce v Henrique Rocha | 4-6,6-0,2-6 |
| ITF M25 Martos | 2023/06/17 18:50 | Pedro Vives Marcos v Henrique Rocha | 6-3,6-3 |
| ITF M25 Martos | 2023/06/16 16:00 | Henrique Rocha v John Echeverria | 6-2,6-4 |
| ITF M25 Martos | 2023/06/14 08:00 | Henrique Rocha v Mario G Fernandez | 2-6,7-6,6-4 |
| ITF M25 Mataro | 2023/05/26 09:00 | Kyle Kang v Henrique Rocha | 6-1,6-4 |
| ITF M25 Mataro | 2023/05/23 11:05 | Henrique Rocha v Alex M Pujolras | 6-0,6-3 |
| Challenger Oeiras | 2023/05/14 09:00 | Benjamin Hassan v Henrique Rocha | 6-4,7-5 |