[10] Estrela Amadora 0-1 Guimaraes [14] 2023-08-13 17:00
Stadium: Estadio Jose Gomes Round: 1
Referee: Manuel Antonio Rodrigues Oliveira Home Manager: Sergio Vieira Away Manager: Moreno
Home History
| Portugal League Cup | 2023/07/23 19:30 | Portimonense v Estrela | L | 3-1 |
| Portugal Primeira Liga Play-Off | 2023/06/11 19:15 | Maritimo v Estrela | D | 4-4 |
| Portugal Primeira Liga Play-Off | 2023/06/03 19:00 | Estrela v Maritimo | W | 2-1 |
| Portugal Segunda Liga | 2023/05/27 10:00 | Penafiel v Estrela | W | 2-4 |
| Portugal Segunda Liga | 2023/05/21 10:00 | Estrela v Nacional | L | 0-1 |
| Portugal Segunda Liga | 2023/05/12 17:00 | Trofense v Estrela | D | 2-2 |
| Portugal Segunda Liga | 2023/05/06 17:00 | Estrela v Moreirense | L | 2-4 |
| Portugal Segunda Liga | 2023/04/28 17:00 | UD Oliveirense v Estrela | W | 1-2 |
Away History
| UEFA Conference League Qualifying | 2023/08/03 19:15 | Guimaraes v NK Celje | L | 2-5 |
| UEFA Conference League Qualifying | 2023/07/27 18:00 | NK Celje v Guimaraes | W | 3-4 |
| Europe Friendlies | 2023/07/23 16:00 | Varzim v Guimaraes | L | 7-6 |
| Europe Friendlies | 2023/07/22 19:15 | Guimaraes v Tondela | L | 3-5 |
| Europe Friendlies | 2023/07/15 17:00 | Rio Ave v Guimaraes | D | 1-1 |
| Europe Friendlies | 2023/07/12 18:15 | AD Fafe v Guimaraes | W | 0-2 |
| Portugal Primeira Liga | 2023/05/27 17:00 | FC Porto v Guimaraes | L | 3-0 |
| Portugal Primeira Liga | 2023/05/21 14:30 | Guimaraes v Gil Vicente | W | 1-0 |