[11] Deportivo Maldonado 0-1 Penarol [4] 2023-10-14 00:00
Stadium: Estadio Centenario Round: 5
Referee: Andres Matonte Home Manager: Fabian Coito Machado Away Manager: Dario Rodriguez
Head to Head
| Uruguay Apertura | 2023/03/05 20:00 | Penarol v Deportivo Maldonado | L | 2-1 |
| Uruguay Clausura | 2022/08/22 22:00 | Deportivo Maldonado v Penarol | D | 1-1 |
| Uruguay Torneo Intermedio | 2022/06/19 20:30 | Deportivo Maldonado v Penarol | L | 1-3 |
| Uruguay Apertura | 2022/03/19 21:00 | Penarol v Deportivo Maldonado | D | 1-1 |
| Uruguay Clausura | 2021/10/17 18:30 | Deportivo Maldonado v Penarol | W | 1-0 |
| Uruguay Apertura | 2021/06/20 18:45 | Penarol v Deportivo Maldonado | L | 4-0 |
| Uruguay Clausura | 2021/02/11 23:00 | Penarol v Deportivo Maldonado | D | 1-1 |
| Uruguay Torneo Intermedio | 2020/11/08 21:00 | Penarol v Deportivo Maldonado | L | 4-1 |
Home History
| Uruguay Clausura | 2023/10/08 18:30 | Boston River v Deportivo Maldonado | L | 2-0 |
| Uruguay Clausura | 2023/09/03 23:30 | Deportivo Maldonado v Cerro | W | 2-1 |
| Uruguay Clausura | 2023/08/27 15:30 | Racing Club de Montevideo v Deportivo Maldonado | D | 1-1 |
| Uruguay Clausura | 2023/08/18 22:00 | Deportivo Maldonado v Plaza Colonia | D | 0-0 |
| Uruguay Torneo Intermedio | 2023/07/22 15:15 | Racing Club de Montevideo v Deportivo Maldonado | L | 2-0 |
| Uruguay Torneo Intermedio | 2023/07/17 22:00 | Deportivo Maldonado v Cerro | L | 1-2 |
| Uruguay Torneo Intermedio | 2023/07/09 15:30 | Plaza Colonia v Deportivo Maldonado | W | 1-3 |
| Uruguay Torneo Intermedio | 2023/07/03 18:00 | Liverpool Montevideo v Deportivo Maldonado | L | 3-2 |
Away History
| Uruguay Clausura | 2023/10/07 21:30 | Penarol v Defensor Sporting | W | 2-1 |
| Uruguay Clausura | 2023/09/02 18:30 | Boston River v Penarol | W | 0-1 |
| Uruguay Clausura | 2023/08/27 18:30 | Penarol v La Luz | D | 2-2 |
| Uruguay Clausura | 2023/08/19 18:30 | Cerro v Penarol | D | 1-1 |
| Uruguay Torneo Intermedio | 2023/07/23 18:00 | Penarol v Defensor Sporting | W | 2-1 |
| Uruguay Torneo Intermedio | 2023/07/16 18:00 | Penarol v Boston River | W | 2-1 |
| Uruguay Torneo Intermedio | 2023/07/08 18:00 | Danubio v Penarol | L | 1-0 |
| Uruguay Torneo Intermedio | 2023/07/03 22:30 | Penarol v Torque | W | 2-0 |