1. Round | 14/07/2023 | Pirin Blagoevgrad | - | PFC Beroe | 1:2 | ||||
2. Round | 21/07/2023 | CSKA 1948 Sofia | - | Pirin Blagoevgrad | 3:0 | ||||
3. Round | 29/07/2023 | Pirin Blagoevgrad | - | Botev Plovdiv | 0:0 | ||||
4. Round | 05/08/2023 | Lokomotiv Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
5. Round | 11/08/2023 | Pirin Blagoevgrad | - | Lokomotiv Plovdiv | 0:1 | ||||
7. Round | 25/08/2023 | Pirin Blagoevgrad | - | Botev Vratsa | 0:1 | ||||
8. Round | 01/09/2023 | Pirin Blagoevgrad | - | Arda Kardzhali | 0:2 | ||||
13. Round | 08/10/2023 | PFC Ludogorets Razgrad | - | Pirin Blagoevgrad | 4:0 |