| Challenger - Oeiras | 06/20 13:10 | 19 | [411] Oscar Jose Gutierrez v Edoardo Lavagno [394] | 6-2,6-4 | |
| Challenger - Oeiras | 06/19 16:30 | 14 | [354] Yshai Oliel v Oscar Jose Gutierrez [413] | 3-6,6-7 | |
| Challenger - Perugia | 06/06 10:25 | 19 | [487] Giovanni Oradini v Oscar Jose Gutierrez [415] | 3-6,6-3,7-5 | |
| Challenger - Perugia | 06/05 12:45 | 14 | Cristian Campese v Oscar Jose Gutierrez | 3-6,2-6 | |
| Challenger - Forlì | 05/30 08:00 | 19 | [416] Oscar Jose Gutierrez v Matteo Martineau [410] | 5-7,7-5,4-6 | |
| Challenger - Forlì | 05/29 08:00 | 14 | [272] Nicolas Alvarez Varona v Oscar Jose Gutierrez [416] | 2-6,6-7 | |
| ITF - M25 Mataro | 05/27 10:00 | 27 | [291] Raul Brancaccio v Oscar Jose Gutierrez [416] | 7-6,6-0 | |
| ITF - M25 Mataro | 05/26 10:00 | 26 | [416] Oscar Jose Gutierrez v Kyrian Jacquet [331] | 6-2,6-4 | |
| ITF - M25 Mataro | 05/25 15:25 | 25 | Leonid Sheyngezikht v Oscar Jose Gutierrez | 6-3,2-6,2-6 | |
| ITF M25 - Vic | 05/18 09:00 | 25 | Kuzey Cekirge v Oscar Jose Gutierrez | 3-6,7-5,6-3 | |
| ITF M15 - Valldoreix | 05/12 10:55 | 26 | Daniel Merida Aguilar v Oscar Jose Gutierrez | 6-7,6-4,6-4 | |
| ITF M15 - Valldoreix | 05/10 11:00 | 25 | Edas Butvilas v Oscar Jose Gutierrez | 3-6,6-7 | |
| Challenger - Aix en Provence | 05/01 08:00 | 14 | Oscar Jose Gutierrez v Calvin Hemery | 3-6,3-6 | |
| ITF M25 - Angers | 04/22 14:10 | 27 | Oscar Jose Gutierrez v Jurgen Briand | 4-6,1-6 | |
| ITF M25 - Angers | 04/21 11:25 | 26 | Oscar Jose Gutierrez v Johan Sebastien Tatlot | 7-6,6-0 | |
| ITF M25 - Angers | 04/20 09:35 | 25 | [409] Oscar Jose Gutierrez v Petros Tsitsipas [199] | 5-7,7-6,6-0 | |
| Challenger - Oeiras | 04/06 09:30 | 26 | [423] Oscar Jose Gutierrez v Zdenek Kolar [150] | 4-6,3-6 | |
| Challenger - Oeiras | 04/05 09:30 | 25 | Oscar Jose Gutierrez v Tiago Cacao | 6-2,6-3 | |
| Challenger - Oeiras | 04/04 09:30 | 19 | Henrique Rocha v Oscar Jose Gutierrez | 5-7,6-7 | |
| Challenger - Oeiras - Kwal. | 04/03 11:55 | 14 | Jaime Faria v Oscar Jose Gutierrez | 2-6,4-6 | |
| ITF M15 - Palmanova | 03/27 08:30 | 29 | Carlos L-Montagud v Oscar Jose Gutierrez | 7-5,3-6,7-6 | |
| ITF M15 - Palmanova | 03/26 09:00 | 28 | Oscar Jose Gutierrez v Miguel Damas | 6-4,6-1 | |
| ITF M15 - Palmanova | 03/25 09:30 | 27 | Oscar Jose Gutierrez v Luigi Sorrentino | 6-0,7-6 | |
| ITF M15 - Palmanova | 03/24 12:15 | 26 | Oscar Jose Gutierrez v Imanol L Morillo | 6-1,6-4 | |
| ITF M15 - Palmanova | 03/23 11:00 | 25 | Oscar Jose Gutierrez v Manuel Mazza | 7-5,6-0 | |
| ITF M15 - Palmanova | 03/20 09:00 | 29 | Carlos L-Montagud v Oscar Jose Gutierrez | 6-1,7-5 | |
| ITF M15 - Palmanova | 03/19 09:30 | 28 | Diego A B Sanchez v Oscar Jose Gutierrez | 1-6,0-6 | |
| ITF M15 - Palmanova | 03/18 12:30 | 27 | Miguel Damas v Oscar Jose Gutierrez | 6-7,6-2,3-6 | |
| ITF M15 - Palmanova | 03/17 14:45 | 26 | Peter Benjamin Privara v Oscar J. Gutierrez | 7-6,3-6,3-6 | |
| ITF M15 - Palmanova | 03/16 12:30 | 25 | Jorge Martinez Martinez v Oscar J. Gutierrez | 4-6,2-6 |