| Challenger - Alicante | 10/02 08:00 | 14 | John Echeverria v Oscar Jose Gutierrez | 4-6,6-4,2-6 | |
| Challenger - Genova | 09/20 08:00 | 25 | [366] Oscar Jose Gutierrez v Raul Brancaccio [181] | 1-6,2-6 | |
| Challenger - Genova | 09/19 09:35 | 19 | [366] Oscar Jose Gutierrez v Matteo Martineau [455] | 4-6,6-3,2-6 | |
| Challenger - Genova | 09/18 12:45 | 14 | Oscar Jose Gutierrez v Lorenzo Claverie | 6-4,6-7,7-6 | |
| Challenger - Stettin | 09/11 12:20 | 14 | [436] Elmar Ejupovic v Oscar Jose Gutierrez [378] | 4-6,6-4,7-6 | |
| Challenger - Sevilla | 09/05 10:40 | 19 | [302] Filip C Jianu v Oscar Jose Gutierrez [378] | 6-2,7-6 | |
| Challenger - Sevilla | 09/04 14:00 | 14 | [490] Pablo Llamas Ruiz v Oscar Jose Gutierrez [378] | 3-6,6-7 | |
| ITF - M25 - Santander | 08/27 09:30 | 29 | [371] Oscar Jose Gutierrez v Titouan Droguet [462] | 6-7,0-6 | |
| ITF - M25 - Santander | 08/26 15:00 | 28 | Oscar Jose Gutierrez v Alejandro Manzanera Pertusa | 6-2,3-6,7-5 | |
| ITF - M25 - Santander | 08/25 12:30 | 27 | [371] Oscar Jose Gutierrez v Pablo Llamas Ruiz [493] | 6-3,7-6 | |
| ITF - M25 - Santander | 08/24 12:25 | 26 | Oscar Jose Gutierrez v Benjamin Winter Lopez | 6-4,4-6,7-6 | |
| Challenger - Meerbusch | 08/08 09:00 | 19 | [362] Clement Tabur v Oscar Jose Gutierrez [377] | 4-6,6-2,6-4 | |
| Challenger - Meerbusch | 08/07 11:00 | 14 | Tom Gentzsch v Oscar Jose Gutierrez | 6-2,5-7,3-6 | |
| Challenger - Cordenons | 08/01 08:00 | 19 | Giacomo Dambrosi v Oscar Jose Gutierrez | 6-4,6-3 | |
| Challenger - Cordenons | 07/31 08:00 | 14 | [477] Jonathan Mridha v Oscar Jose Gutierrez [374] | 2-6,3-6 | |
| Challenger - San Benedetto | 07/24 11:00 | 14 | Federico Iannaccone v Oscar Jose Gutierrez | 6-3,6-3 | |
| Challenger - Amersfoort | 07/12 10:25 | 25 | [368] Oscar Jose Gutierrez v Laurent Lokoli [246] | 2-6,1-6 | |
| Challenger - Amersfoort | 07/11 11:05 | 19 | [314] Luca Van Assche v Oscar Jose Gutierrez [368] | 7-5,6-3 | |
| Challenger - Amersfoort | 07/10 13:15 | 45 | [464] Vladyslav Orlov v Oscar Jose Gutierrez [389] | 6-7,4-6 | |
| Challenger - Braunschweig | 07/06 09:00 | 26 | [96] Henri Laaksonen v Oscar Jose Gutierrez [389] | 6-7,6-3,6-4 | |
| Challenger - Braunschweig | 07/05 09:00 | 25 | Oscar Jose Gutierrez v Marko Topo | 6-2,6-2 | |
| Challenger - Braunschweig | 07/04 09:00 | 19 | Oscar Jose Gutierrez v Vaclav Safranek | 6-4,6-4 | |
| Challenger - Braunschweig | 07/03 09:00 | 14 | [275] Lorenzo Giustino v Oscar Jose Gutierrez [389] | 4-6,2-6 | |
| Challenger - Troyes | 06/27 14:00 | 19 | [379] Francesco Maestrelli v Oscar Jose Gutierrez [411] | 6-2,6-2 | |
| Challenger - Troyes | 06/26 11:00 | 14 | Matteo Donati v Oscar Jose Gutierrez | Retired | |
| Challenger - Oeiras | 06/23 09:00 | 26 | [411] Oscar Jose Gutierrez v Kyrian Jacquet [451] | 4-6,3-6 | |
| Challenger - Oeiras | 06/21 15:50 | 25 | [280] Oriol Roca Batalla v Oscar Jose Gutierrez [411] | 4-6,4-6 | |
| 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 |