| ITF M25 Bakio | 06/30 10:05 | 25 | Diaz Freire, Gabriel v Montes-de La Torre, Inaki | 2-6,3-6 | |
| ITF M25 Bakio | 06/29 09:30 | 54 | Diego F Flores v Diaz Freire, Gabriel | 6-1,6-7,12-14 | |
| ITF M25 Bakio | 06/27 16:00 | 54 | Diaz Freire, Gabriel v Mario Mansilla Diez | 6-4,3-6,10-6 | |
| ITF M25 Denia | 07/22 08:30 | 54 | Diaz Freire, Gabriel v Kotecha, Sheil | 6-7,2-6 | |
| ITF M25 Getxo | 07/09 11:25 | 45 | Boris Arias v Diaz Freire, Gabriel | 6-2,3-6,10-6 | |
| ITF M25 Getxo | 07/08 11:00 | 45 | Diaz Freire, Gabriel v Dagnino, Paolo | 3-6,7-6,11-9 | |
| ITF M25 Bakio | 07/01 08:45 | 54 | Aranzabal, Mikel v Diaz Freire, Gabriel | 6-3,6-2 | |
| ITF USA F30 | 11/02 19:30 | 60 | Mwendwa Mbithi v Diaz Freire, Gabriel | 3-6,7-5,6-0 | |
| ITF USA F27 | 10/08 20:10 | 62 | Hendrik Jebens v Diaz Freire, Gabriel | 4-6,6-3,6-2 | |
| ITF USA F27 | 10/07 15:00 | 62 | Diaz Freire, Gabriel v Giusca, Teodor | 6-4,6-4 | |
| ITF USA F27 | 10/06 15:00 | 62 | Diaz Freire, Gabriel v Keenan Mayo | 2-6,6-3,6-2 | |
| ITF Morocco F4 | 08/06 11:00 | 25 | Diaz Freire, Gabriel v Bessire, Andrea | 5-7,3-6 | |
| ITF Morocco F4 | 08/05 14:00 | 44 | Diaz Freire, Gabriel v Butsch, Justin | 2-6,3-6 | |
| ITF Morocco F4 | 08/05 09:00 | 44 | Diaz Freire, Gabriel v Del Olmo Diaz, Ramon | Retired | |
| ITF Morocco F3 | 07/31 09:00 | 25 | Diaz Freire, Gabriel v Bessire, Andrea | 5-7,0-6 | |
| ITF Morocco F3 | 07/29 15:00 | 44 | Diaz Freire, Gabriel v Del Olmo Diaz, Ramon | 6-1,6-3 | |
| ITF Spain F17 | 07/05 16:40 | 26 | Diaz Freire, Gabriel v Alberto Barroso Campos | 6-1,1-6,1-6 | |
| ITF Spain F17 | 07/04 10:00 | - | Diaz Freire, Gabriel v Alberto Barroso Campos | 6-1,1-6,1-6 | |
| ITF Spain F17 | 07/03 13:00 | 25 | Diaz Freire, Gabriel v Romero de Avila Senise, Alberto | 6-1,7-6 | |
| ITF Spain F17 Qual | 07/01 17:55 | 54 | Tatyanin, Nikita v Diaz Freire, Gabriel | 5-7,2-6 | |
| ITF Spain F17 Qual | 07/01 09:10 | 54 | Ribeiro Navarrete, Samuel v Diaz Freire, Gabriel | 4-6,4-6 | |
| ITF Czech Republic F4 Qual | 06/23 08:00 | 62 | Pechala, Frantisek v Diaz Freire, Gabriel | 6-1,7-6 | |
| ITF Hungary F5 Qual | 06/16 12:00 | 62 | Diaz Freire, Gabriel v Duje Ajdukovic | 3-6,2-6 | |
| ITF USA F32 | 09/24 17:00 | 60 | Diaz Freire, Gabriel v Ventre, Alessandro-Damiano | 3-6,5-7 | |
| ITF USA F32 | 09/23 15:30 | 60 | Orkin, Elliott v Diaz Freire, Gabriel | 3-6,7-6,0-6 | |
| ITF USA F32 | 09/22 17:30 | 60 | Keenan Mayo v Diaz Freire, Gabriel | 3-6,1-6 | |
| ITF USA F30 | 09/11 16:00 | 60 | Strong Kirchheimer v Diaz Freire, Gabriel | 7-6,6-3 | |
| ITF USA F30 | 09/10 16:00 | 60 | Rafael Tosetto v Diaz Freire, Gabriel | 4-6,3-6 | |
| ITF USA F30 | 09/09 17:00 | 60 | Ortlip, Joshua v Diaz Freire, Gabriel | Retired | |
| ITF Spain F25 | 08/14 08:00 | 44 | Sanz Llopis, Aitor v Diaz Freire, Gabriel | 6-1,6-3 |