Stadium: Dom Afonso Henriques Round: 17
Referee: Irfan Peljto Home Manager: Ivo Ricardo Abreu Vieira Away Manager: Virgil Andronache
| UEFA Europa League Qualifying | 2019/08/01 19:00 | Guimaraes v Jeunesse Esch | W | 4-0 |
| UEFA Europa League Qualifying | 2019/07/25 18:30 | Jeunesse Esch v Guimaraes | W | 0-1 |
| Europe Friendlies | 2019/07/17 16:00 | Rio Ave v Guimaraes | W | 0-1 |
| Europe Friendlies | 2019/07/14 17:00 | Guimaraes v Famalicao | W | 5-2 |
| Europe Friendlies | 2019/07/10 17:00 | Guimaraes v CD Aves | W | 1-0 |
| Portugal Primeira Liga | 2019/05/19 19:00 | Moreirense v Guimaraes | W | 1-3 |
| Portugal Primeira Liga | 2019/05/12 14:00 | Guimaraes v Belenenses | W | 5-1 |
| Portugal Primeira Liga | 2019/05/05 19:00 | Guimaraes v Nacional | D | 2-2 |
| UEFA Europa League Qualifying | 2019/08/01 18:30 | FCSB v Alashkert FC | L | 2-3 |
| Romania Liga I | 2019/07/29 17:00 | FCSB v FC Botosani | L | 0-2 |
| UEFA Europa League Qualifying | 2019/07/25 17:00 | Alashkert FC v FCSB | W | 0-3 |
| Romania Liga I | 2019/07/22 18:00 | ACS Sepsi v FCSB | D | 0-0 |
| UEFA Europa League Qualifying | 2019/07/18 17:00 | FC Milsami v FCSB | W | 1-2 |
| Romania Liga I | 2019/07/14 18:00 | FCSB v AFC Hermannstadt | W | 4-3 |
| UEFA Europa League Qualifying | 2019/07/11 18:30 | FCSB v FC Milsami | W | 2-0 |
| Europe Friendlies | 2019/07/04 17:30 | CS Mioveni v FCSB | W | 0-1 |