| Uruguay U19 League | 2019/11/26 14:00 | Penarol U19 v Deportivo Maldonado U19 | W | 4-1 |
| Uruguay U19 League | 2017/07/04 14:00 | Deportivo Maldonado U19 v Penarol U19 | D | 3-3 |
| Uruguay U19 League | 2016/11/22 15:30 | Penarol U19 v Deportivo Maldonado U19 | L | 1-2 |
| Uruguay U19 League | 2023/05/20 12:00 | Penarol U19 v Boston River U19 | W | 3-0 |
| Uruguay U19 League | 2023/05/13 11:30 | Atletico Fenix Montevideo U19 v Penarol U19 | W | 1-3 |
| Uruguay U19 League | 2023/04/04 12:00 | Penarol U19 v Defensor Sporting U19 | L | 2-3 |
| Uruguay U19 League | 2023/03/10 12:00 | Penarol U19 v Villa Espanola U19 | W | 6-0 |
| Uruguay U19 League | 2022/10/19 13:00 | Penarol U19 v Defensor Sporting U19 | W | 2-0 |
| Uruguay U19 League | 2021/11/06 12:00 | CA River Plate U19 v Penarol U19 | D | 0-0 |
| Uruguay U19 League | 2021/11/02 12:00 | Juventud U19 v Penarol U19 | D | 0-0 |
| Uruguay U19 League | 2021/10/30 13:00 | Penarol U19 v Tacuarembo U19 | W | 4-0 |
| Uruguay U19 League | 2023/05/13 14:30 | Villa Espanola U19 v Deportivo Maldonado U19 | L | 1-0 |
| Uruguay U19 League | 2023/04/25 14:00 | Racing Club de Montevideo U19 v Deportivo Maldonado U19 | D | 1-1 |
| Uruguay U19 League | 2023/04/22 14:00 | Albion FC U19 v Deportivo Maldonado U19 | L | 5-1 |
| Uruguay U19 League | 2023/03/25 12:30 | Nacional De Football U19 v Deportivo Maldonado U19 | L | 4-0 |
| Uruguay U19 League | 2023/03/11 13:00 | Boston River U19 v Deportivo Maldonado U19 | D | 2-2 |
| Uruguay U19 League | 2021/12/01 12:00 | Progreso U19 v Deportivo Maldonado U19 | L | 1-0 |
| Uruguay U19 League | 2021/11/19 13:30 | Deportivo Maldonado U19 v Cerro U19 | L | 0-4 |
| Uruguay U19 League | 2021/11/02 14:00 | Deportivo Maldonado U19 v Racing Club de Montevideo U19 | L | 1-2 |