Stadium: Court 1 Round: 54 Ground: Clay
| ITF M15 Antalya | 2023/05/09 10:05 | Edas Butvilas v Jaime Caldes | 6-3,6-4 |
| ITF M15 Antalya | 2023/05/03 11:10 | Jaime Caldes v Alexandr Binda | 3-6,3-6 |
| ITF M15 Telde | 2023/04/12 09:50 | Alberto Barroso Campos v Jaime Caldes | 6-2,6-7,6-2 |
| ITF M25 Reus | 2023/04/02 08:30 | David Naharro Gomez v Jaime Caldes | 6-4,2-6,10-6 |
| ITF M25 Palmanova | 2023/03/22 08:00 | Jaime Caldes v Alexander Weis | 3-6,6-2,2-6 |
| ITF M25 Palmanova | 2023/03/21 13:20 | Jaime Caldes v Darius Florin Pop | 6-3,6-1 |
| ITF M25 Palmanova | 2023/03/20 14:00 | Jaime Caldes v Freddy Humphries | 6-3,6-0 |
| ITF M15 Sharm El Sheikh | 2023/02/15 13:55 | Simone Roncalli v Jaime Caldes | 6-2,7-5 |
| ITF M15 Doboj | 2023/05/12 07:00 | Kirill Mishkin v Ryan Nijboer | 2-6,0-6 |
| ITF M15 Doboj | 2023/05/10 08:00 | Kirill Mishkin v Stefan Kostic | 6-2,1-6,6-1 |
| ITF M15 Doboj | 2023/05/08 10:30 | Kirill Mishkin v Matt Hulme | 6-3,7-6 |
| ITF M15 Monastir | 2023/04/16 08:00 | Kirill Mishkin v Pablo Trochu | 1-6,1-6 |
| ITF M15 Monastir | 2023/04/09 10:00 | Kirill Mishkin v Max Wiskandt | 1-6,2-6 |
| ITF M15 Monastir | 2023/02/05 11:00 | Kirill Mishkin v Simon Freund | 2-6,3-6 |
| ITF M15 Monastir | 2023/01/16 08:30 | Pierre Delage v Kirill Mishkin | 6-2,6-0 |
| ITF M15 Monastir | 2023/01/15 10:30 | Kirill Mishkin v Sushant Dabas | 6-2,3-6,10-6 |