| ITF - Brasil F8 | 11/06 17:55 | 25 | Oscar Jose Gutierrez v Fermin Tenti | 4-6,6-4,7-6 | |
| ITF - Brasil F7 | 10/29 16:05 | 25 | Oscar Jose Gutierrez v Carlos E. Severino | 6-2,3-6,4-6 | |
| ITF - Brasil F6 | 10/23 18:00 | 25 | Oscar Jose Gutierrez v Ignacio Monzon | 4-6,4-6 | |
| ITF - Brasil F5 | 10/19 13:00 | 27 | [389] Oscar Jose Gutierrez v Rafael Matos [343] | 3-6,6-7 | |
| ITF - Brasil F5 | 10/18 13:00 | 26 | Oscar Jose Gutierrez v Carlos E. Severino | 6-3,6-1 | |
| ITF - Brasil F5 | 10/15 22:00 | 25 | Oscar Jose Gutierrez v Ignacio Carou | 6-4,7-5 | |
| Challenger - Campinas | 10/01 13:00 | 54 | Oscar Jose Gutierrez v Nicolas Alvarez | 3-6,5-7 | |
| Challenger - Campinas | 09/30 13:00 | 46 | [391] Oscar Jose Gutierrez v Tomas Lipovsek Puches [236] | 6-7,6-3,6-2 | |
| Challenger - Campinas - Qualificação | 09/29 13:00 | 45 | Oscar Jose Gutierrez v Breno Lodis | 6-1,6-1 | |
| Challenger - Biella | 09/18 10:30 | 25 | [180] Matteo Donati v Oscar Jose Gutierrez [398] | 6-3,6-3 | |
| Challenger - Biella | 09/17 10:00 | 54 | [451] Jan Satral v Oscar Jose Gutierrez [398] | 6-2,6-2 | |
| Challenger - Biella | 09/16 12:00 | 46 | Francesco Paschetto v Oscar Jose Gutierrez | 3-6,0-6 | |
| Challenger - Biella | 09/15 12:00 | 45 | Jannik Sinner v Oscar Jose Gutierrez | 6-4,4-6,6-7 | |
| ITF - Itália F27 | 09/13 16:25 | 27 | [413] Oscar Jose Gutierrez v Marco Bortolotti [296] | 3-6,1-6 | |
| ITF - Itália F27 | 09/12 16:35 | 26 | Oscar Jose Gutierrez v Enrico Dalla Valle | 6-1,6-2 | |
| ITF - Itália F27 | 09/11 12:00 | 25 | Oscar Jose Gutierrez v Francois-Arthur Vibert | 7-6,2-6,6-2 | |
| ITF - Itália F27 | 09/08 14:00 | 54 | Oscar Jose Gutierrez v Matteo Curci | 6-2,6-3 | |
| ITF - Itália F26 | 09/07 11:15 | 28 | [474] Gijs Brouwer v Oscar Jose Gutierrez [412] | 6-4,6-4 | |
| ITF - Itália F26 | 09/06 10:35 | 27 | [399] Karim-Mohamed Maamoun v Oscar Jose Gutierrez [412] | Retired | |
| ITF - Itália F26 | 09/05 08:00 | 26 | Johannes Bangratz v Oscar Jose Gutierrez | 4-6,1-6 | |
| ITF - Itália F26 | 09/03 08:30 | 25 | Federico Arnaboldi v Oscar Jose Gutierrez | 2-6,3-6 | |
| ITF - Hungria F7 | 08/30 08:30 | 26 | Oscar Jose Gutierrez v Alexander Erler | 4-6,4-6 | |
| ITF - Hungria F7 | 08/28 08:30 | 25 | Oscar Jose Gutierrez v Domen Gostincar | 6-3,6-2 | |
| ITF - Equador F2 | 08/04 16:00 | 29 | Oscar Jose Gutierrez v Emilio Gomez | 6-4,5-7,4-6 | |
| ITF - Equador F2 | 08/03 18:10 | 28 | [421] Oscar Jose Gutierrez v Bernardo Saraiva [258] | 4-6,6-4,6-3 | |
| ITF - Equador F2 | 08/02 17:25 | 27 | Oscar Jose Gutierrez v Facundo Juarez | 6-1,6-3 | |
| ITF - Equador F2 | 08/01 15:00 | 26 | Oscar Jose Gutierrez v Julian Gimenez | 6-1,6-0 | |
| ITF - Equador F2 | 07/30 22:30 | 25 | Oscar Jose Gutierrez v Daniel Mora | 6-2,6-1 | |
| ITF - Equador F1 | 07/24 15:00 | 25 | Oscar Jose Gutierrez v Joao Hinsching | 3-6,6-7 | |
| ITF - República Checa F5 | 07/05 09:55 | 27 | [431] Oscar Jose Gutierrez v David Poljak [499] | 4-6,1-6 |