Summary of previous matches between the team of FK Skopje and the team of FK Osogovo since 2023-11-27:
FK Skopje won 1 matches against FK Osogovo, lost 1 matches, and 2 matches were draws.
| Time | League | Home Team | Score | Away Team |
|---|---|---|---|---|
| 2021-12-08 | Macedonian First Football League | FK Skopje | 1 : 0 | Vlazrimi Struga |
| 2021-12-05 | Macedonian First Football League | FK Skopje | 1 : 3 | FK Shkupi |
| 2021-11-28 | Macedonian First Football League | Pelister Bitola | 0 : 0 | FK Skopje |
| 2021-11-20 | Macedonian First Football League | FK Skopje | 1 : 2 | FK Makedonija Gjorce Petrov |
| 2021-11-06 | Macedonian First Football League | Bregalnica Stip | 2 : 1 | FK Skopje |
| 2021-10-30 | Macedonian First Football League | FK Skopje | 0 : 0 | Renova Cepciste |
| 2021-10-24 | Macedonian First Football League | FK Skopje | 2 : 1 | FK Tikves Kavadarci |
| 2021-10-20 | FYR Macedonia Cup | FC Vardar Skopje | 0 : 0 | FK Skopje |
| 2021-10-15 | Macedonian First Football League | Rabotnicki Skopje | 0 : 1 | FK Skopje |
| 2021-10-02 | Macedonian First Football League | FK Skopje | 0 : 0 | Academy Pandev |
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