Stadium: Court 4 Round: 26 Ground: Clay
| ITF M25 Sharm El Sheikh | 2023/09/21 07:00 | Gianluca Cadenasso v Zura Tkemaladze | 4-6,4-6 |
| ITF M25 Sharm El Sheikh | 2023/09/20 08:30 | Marek Gengel v Gianluca Cadenasso | 6-7,0-6 |
| ITF M25 Sharm El Sheikh | 2023/09/19 08:30 | Gianluca Cadenasso v Tsihon Fedorov | 6-3,6-2 |
| ITF M25 Sharm El Sheikh | 2023/09/18 09:55 | Gianluca Cadenasso v Shahar Gabay | 6-2,6-2 |
| Challenger Genoa | 2023/09/04 09:50 | Giovanni Oradini v Gianluca Cadenasso | 6-2,6-4 |
| Challenger Genoa | 2023/09/03 13:50 | Gianluca Cadenasso v Fausto Tabacco | 3-6,6-4,6-3 |
| ITF M25 Ystad | 2023/08/16 08:45 | Gianluca Cadenasso v Jonathan Mridha | 3-6,4-6 |
| ITF M25 Ystad | 2023/08/15 10:00 | Gianluca Cadenasso v Fabian Hansch Mauritzson | 6-0,6-1 |
| Challenger Seville | 2023/09/04 16:50 | Inigo C Huegun v Oscar Jose Gutierrez | 7-5,6-2 |
| Challenger Seville | 2023/09/04 13:00 | Alex Lawson v Oscar Jose Gutierrez | 1-6,2-6 |
| ITF M25 Oviedo | 2023/08/30 09:15 | Oscar Jose Gutierrez v Facundo Mena | 3-6,2-6 |
| ITF M25 Santander | 2023/08/23 09:50 | Sergi Perez Contri v Oscar Jose Gutierrez | 6-4,7-6 |
| ITF M25 Santander | 2023/08/22 13:00 | Oscar Jose Gutierrez v Michiel de Krom | 6-2,6-0 |
| Challenger Liberec | 2023/07/30 08:00 | Kirill Kivattsev v Oscar Jose Gutierrez | 6-2,6-4 |
| ITF M25 Denia | 2023/07/26 15:25 | Oscar Jose Gutierrez v Vilius Gaubas | 5-7,6-7 |
| Challenger Braunschweig | 2023/07/09 14:10 | Oscar Jose Gutierrez v Karl Friberg | 0-6,6-2,3-6 |