| 1. Round | 09/07/2022 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 2:1 | ||||
| 2. Round | 17/07/2022 | Pirin Blagoevgrad | - | CSKA 1948 Sofia | 1:1 | ||||
| 3. Round | 22/07/2022 | Spartak Varna | - | Pirin Blagoevgrad | 1:1 |  |
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| 4. Round | 30/07/2022 | Pirin Blagoevgrad | - | Slavia Sofia | 1:2 | ||||
| 5. Round | 07/08/2022 | Levski Sofia | - | Pirin Blagoevgrad | 1:0 |  |
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| 7. Round | 22/08/2022 | Pirin Blagoevgrad | - | PFC Ludogorets Razgrad | 0:4 | ||||
| 8. Round | 28/08/2022 | Hebar Pazardzhik | - | Pirin Blagoevgrad | 0:0 | ||||
| 9. Round | 02/09/2022 | Pirin Blagoevgrad | - | Botev Vratsa | 2:1 |  |
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| 10. Round | 12/09/2022 | Arda Kardzhali | - | Pirin Blagoevgrad | 0:0 | ||||
| 11. Round | 17/09/2022 | Pirin Blagoevgrad | - | Lokomotiv Sofia | 0:1 | ||||
| 12. Round | 03/10/2022 | CSKA Sofia | - | Pirin Blagoevgrad | 2:1 | ||||
| 19. Round | 13/02/2023 | Slavia Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 20. Round | 19/02/2023 | Pirin Blagoevgrad | - | Levski Sofia | 1:1 |
Bulgaria