Home History
| Bulgaria B PFG | 2019/07/20 15:30 | Septemvri Sofia v Strumska Slava | W | 2-0 |
| Europe Friendlies | 2019/07/12 07:36 | Septemvri Sofia v FK Borec | D | 1-1 |
| Europe Friendlies | 2019/07/06 15:00 | FK Vitosha v Septemvri Sofia | L | 1-0 |
| Europe Friendlies | 2019/07/03 15:39 | Septemvri Sofia v Teuta Durres | L | 0-2 |
| Europe Friendlies | 2019/06/28 15:00 | Lokomotiv 1929 Sofia v Septemvri Sofia | D | 2-2 |
| Bulgaria Play-Offs | 2019/05/29 15:30 | Septemvri Sofia v Arda Kardzhali | L | 0-1 |
| Bulgaria First League | 2019/05/22 17:00 | Septemvri Sofia v Dunav Ruse | L | 2-3 |
| Bulgaria First League | 2019/05/19 17:00 | Dunav Ruse v Septemvri Sofia | W | 0-1 |
Away History
| Europe Friendlies | 2019/07/13 15:31 | Bregalnica Stip v Rabotnicki Skopje | D | 1-1 |
| Europe Friendlies | 2019/07/10 16:00 | Rabotnicki Skopje v Vardar Skopje | L | 1-2 |
| Europe Friendlies | 2019/07/06 15:42 | Rabotnicki Skopje v FK Borec | L | 0-5 |
| Europe Friendlies | 2019/07/06 10:00 | Rabotnicki Skopje v FK Borec | L | 0-5 |
| North Macedonia First League | 2019/05/26 14:30 | Rabotnicki Skopje v KF Shkupi Skopje | L | 1-2 |
| North Macedonia First League | 2019/05/19 14:30 | Belasica Strumica v Rabotnicki Skopje | W | 0-1 |
| North Macedonia First League | 2019/05/12 14:30 | Rabotnicki Skopje v Makedonija Gj. P | W | 2-0 |
| North Macedonia First League | 2019/05/08 14:30 | Vardar Skopje v Rabotnicki Skopje | D | 1-1 |