| Uruguay U19 League | 11/25 13:30 | - | Defensor Sporting U19 v Deportivo Maldonado U19 | - | View | |
| Uruguay U19 League | 10/07 14:00 | - | CA River Plate U19 v Deportivo Maldonado U19 | L | 3-0 | |
| Uruguay U19 League | 09/22 12:00 | - | Penarol U19 v Deportivo Maldonado U19 | D | 0-0 | |
| Uruguay U19 League | 05/20 13:00 | - | CA Bella Vista U19 v Deportivo Maldonado U19 | - | View | |
| Uruguay U19 League | 05/13 14:30 | - | Villa Espanola U19 v Deportivo Maldonado U19 | L | 1-0 | |
| Uruguay U19 League | 04/25 14:00 | - | Racing Club de Montevideo U19 v Deportivo Maldonado U19 | D | 1-1 | |
| Uruguay U19 League | 04/22 14:00 | - | Albion FC U19 v Deportivo Maldonado U19 | L | 5-1 | |
| Uruguay U19 League | 03/25 12:30 | - | Nacional De Football U19 v Deportivo Maldonado U19 | L | 4-0 | |
| Uruguay U19 League | 03/11 13:00 | - | Boston River U19 v Deportivo Maldonado U19 | D | 2-2 | |
| Uruguay U19 League | 12/01 12:00 | - | Progreso U19 v Deportivo Maldonado U19 | L | 1-0 | |
| Uruguay U19 League | 11/19 13:30 | - | Deportivo Maldonado U19 v Cerro U19 | L | 0-4 | |
| Uruguay U19 League | 11/02 14:00 | - | Deportivo Maldonado U19 v Racing Club de Montevideo U19 | L | 1-2 | |
| Uruguay U19 League | 10/30 14:00 | - | CA Bella Vista U19 v Deportivo Maldonado U19 | W | 0-1 | |
| Uruguay U19 League | 10/16 13:39 | - | Defensor Sporting U19 v Deportivo Maldonado U19 | L | 6-0 | |
| Uruguay U19 League | 09/21 13:30 | - | CA River Plate U19 v Deportivo Maldonado U19 | L | 2-1 | |
| Uruguay U19 League | 08/28 13:30 | - | Juventud De Las Piedras U19 v Deportivo Maldonado U19 | D | 1-1 | |
| Uruguay U19 League | 07/30 15:00 | - | Deportivo Maldonado U19 v Rentistas U19 | L | 0-1 | |
| Uruguay U19 League | 07/17 13:00 | - | Danubio U19 v Deportivo Maldonado U19 | L | 4-1 | |
| Uruguay U19 League | 12/05 15:30 | - | Racing Club de Montevideo U19 v Deportivo Maldonado U19 | W | 1-2 | |
| Uruguay U19 League | 11/06 17:00 | - | Plaza Colonia U19 v Deportivo Maldonado U19 | W | 0-2 | |
| Uruguay U19 League | 02/11 15:30 | - | Defensor Sporting U19 v Deportivo Maldonado U19 | L | 2-0 | |
| Uruguay U19 League | 02/11 12:29 | - | Defensor Sporting U19 v Deportivo Maldonado U19 | L | 2-0 | |
| Uruguay U19 League | 12/10 14:02 | - | Miramar Misiones U19 v Deportivo Maldonado U19 | L | 2-0 | |
| Uruguay U19 League | 11/26 14:00 | - | Penarol U19 v Deportivo Maldonado U19 | L | 4-1 | |
| Uruguay U19 League | 11/19 14:00 | - | Deportivo Maldonado U19 v Nacional De Football U19 | L | 0-3 | |
| Uruguay U19 League | 10/29 15:00 | - | Rentistas U19 v Deportivo Maldonado U19 | L | 5-1 | |
| Uruguay U19 League | 04/15 16:00 | - | Deportivo Maldonado U19 v Cerro U19 | W | 1-0 | |
| Uruguay U19 League | 03/02 14:00 | - | Boston River U19 v Deportivo Maldonado U19 | D | 1-1 | |
| Uruguay U19 League | 09/22 16:00 | - | Deportivo Maldonado U19 v Basanez U19 | W | 7-0 | |
| Uruguay U19 League | 07/04 14:00 | - | Deportivo Maldonado U19 v Penarol U19 | D | 3-3 |