| Segovia, Spain | 07/31 15:45 | 25 | [311] Heyman, Christopher v Monteiro, Joao [323] | 4-6,4-6 | |
| Challenger Padova | 07/25 08:30 | 25 | [276] Boluda-Purkiss, Carlos v Monteiro, Joao [324] | 6-4,6-3 | |
| Milan, Italy | 06/28 09:00 | 26 | [341] Gianluca Mager v Monteiro, Joao [288] | 6-1,6-2 | |
| Milan, Italy | 06/26 09:00 | 25 | [330] Andrea Pellegrino v Monteiro, Joao [288] | 2-6,0-6 | |
| Challenger Blois | 06/19 08:30 | 25 | [324] de Bakker, Thiemo v Monteiro, Joao [288] | 6-2,6-2 | |
| ITF Spain F14 | 06/06 10:00 | 26 | [277] Monteiro, Joao v Desein, Niels [452] | 6-2,4-6,0-6 | |
| ITF Spain F14 | 06/05 11:55 | 25 | [277] Monteiro, Joao v Fred Simonsson [362] | 6-2,6-1 | |
| Challenger Mestre | 05/24 10:25 | 26 | [268] Monteiro, Joao v Mitchell Krueger [253] | 6-7,3-6 | |
| Challenger Mestre | 05/23 14:35 | 25 | Monteiro, Joao v Vilella Martinez, Mario | 7-5,6-7,6-1 | |
| Lisbon, Portugal | 05/15 13:10 | 25 | [84] Taro Daniel v Monteiro, Joao [269] | 7-6,7-6 | |
| Challenger Braga | 05/07 12:20 | 25 | [266] Monteiro, Joao v Gleb Sakharov [209] | 6-2,3-6,2-6 | |
| ATP Estoril Qual | 04/30 13:45 | 45 | [206] Ojeda Lara, Ricardo v Monteiro, Joao [264] | 6-3,2-6,6-3 | |
| ATP Estoril Qual | 04/29 12:35 | 44 | [263] Monteiro, Joao v Robert, Stephane [169] | 6-3,6-7,7-6 | |
| ITF Portugal F8 | 04/20 12:40 | 27 | Monteiro, Joao v Cacao, Tiago | 4-6,5-7 | |
| ITF Portugal F8 | 04/19 13:05 | 26 | [261] Monteiro, Joao v Desein, Niels [451] | 6-2,6-7,6-4 | |
| ITF Portugal F8 | 04/17 12:20 | 25 | [261] Monteiro, Joao v Saraiva, Bernardo [266] | 6-2,6-2 | |
| ITF Portugal F7 | 04/12 11:00 | 25 | [392] Igor Sijsling v Monteiro, Joao [254] | 6-2,6-1 | |
| ITF Portugal F6 | 03/29 12:30 | 27 | [253] Monteiro, Joao v Frederico Ferreira Silva [318] | 6-7,4-6 | |
| ITF Portugal F6 | 03/28 11:30 | 26 | [253] Monteiro, Joao v David Pichler [443] | 7-5,7-6 | |
| ITF Portugal F6 | 03/27 14:55 | 25 | [253] Monteiro, Joao v Neuchrist, Maximilian [349] | 7-6,6-4 | |
| ITF Portugal F5 | 03/24 15:05 | 28 | [253] Monteiro, Joao v Lloyd Harris [293] | 3-6,4-6 | |
| ITF Portugal F5 | 03/23 10:00 | 27 | Monteiro, Joao v Cacao, Tiago | 6-4,6-1 | |
| ITF Portugal F5 | 03/22 16:25 | 26 | Monteiro, Joao v Kenneth Raisma | 6-4,6-1 | |
| ITF Portugal F5 | 03/21 17:15 | 25 | [253] Monteiro, Joao v Sieber, Marc [413] | 5-7,6-3,6-2 | |
| Challenger Santiago Qual | 03/04 17:10 | 46 | Monteiro, Joao v Juan Pablo Ficovich | 2-6,3-6 | |
| Challenger Santiago Qual | 03/03 18:55 | 45 | Monteiro, Joao v Thiago Seyboth Wild | 6-4,7-6 | |
| Challenger - Punta del Este | 02/26 23:45 | 25 | Guido Andreozzi v Monteiro, Joao | 2-6,7-6,6-4 | |
| ITF Spain F2 | 01/26 13:00 | 27 | Monteiro, Joao v Yunseong Chung | 7-6,5-7,3-6 | |
| ITF Spain F2 | 01/25 09:00 | 26 | Monteiro, Joao v Rondoni, Pietro | 6-0,6-2 | |
| ITF Spain F2 | 01/23 12:35 | 25 | Monteiro, Joao v Vega Hernandez, David | 7-6,3-6,6-2 |