[1] Penarol 2-1 Deportivo Maldonado [6] 2023-03-05 20:00
Stadium: Estadio Campeon del Siglo Round: 5
Referee: Javier Burgos Home Manager: Alfredo Arias Away Manager: Fabian Coito Machado
Head to Head
| 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 | W | 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 | L | 1-0 |
| Uruguay Apertura | 2021/06/20 18:45 | Penarol v Deportivo Maldonado | W | 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 | W | 4-1 |
| Uruguay Apertura | 2020/08/19 18:00 | Deportivo Maldonado v Penarol | L | 2-0 |
Home History
| Uruguay Apertura | 2023/02/25 23:00 | Defensor Sporting v Penarol | D | 2-2 |
| Uruguay Apertura | 2023/02/20 00:00 | Penarol v Boston River | W | 1-0 |
| Uruguay Apertura | 2023/02/14 00:00 | La Luz v Penarol | W | 3-4 |
| Uruguay Apertura | 2023/02/04 20:00 | Penarol v Cerro | W | 2-0 |
| Club Friendly List | 2023/01/23 23:30 | Nacional De Football v Penarol | D | 2-2 |
| Club Friendly List | 2023/01/21 00:30 | Penarol v Union Santa Fe | D | 0-0 |
| Club Friendly List | 2023/01/17 23:00 | Penarol v San Lorenzo | W | 1-0 |
| Club Friendly List | 2023/01/13 00:30 | Penarol v Estudiantes LP | W | 3-2 |
Away History
| Copa Libertadores Qualification | 2023/03/03 00:00 | Fortaleza v Deportivo Maldonado | L | 4-0 |
| Uruguay Apertura | 2023/02/26 20:00 | Deportivo Maldonado v Boston River | W | 3-2 |
| Copa Libertadores Qualification | 2023/02/24 00:00 | Deportivo Maldonado v Fortaleza | D | 0-0 |
| Uruguay Apertura | 2023/02/18 20:00 | Cerro v Deportivo Maldonado | D | 0-0 |
| Uruguay Apertura | 2023/02/11 22:30 | Deportivo Maldonado v Racing Club de Montevideo | D | 1-1 |
| Uruguay Apertura | 2023/02/06 22:00 | Plaza Colonia v Deportivo Maldonado | W | 0-1 |
| Club Friendly List | 2023/01/22 20:30 | Barracas Central v Deportivo Maldonado | W | 1-2 |
| Club Friendly List | 2023/01/18 21:15 | Deportivo Maldonado v Independiente del Valle | W | 2-1 |