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Giải đấu
| Liên đoàn | Ngày | Đội nhà | Tỷ số | Đội khách | W/L | Dữ liệu |
|---|---|---|---|---|---|---|
| MKD D2 | 28/11/2026 16:00 | FK Osogovo | FK Ohrid 2004 | |||
| MKD D2 | 21/11/2026 16:00 | FK Shkupi | FK Osogovo | |||
| MKD D2 | 07/11/2026 16:00 | FK Osogovo | Rabotnicki Skopje | |||
| MKD D2 | 31/10/2026 16:00 | FK Makedonija Gjorce Petrov | FK Osogovo | |||
| MKD D2 | 24/10/2026 15:00 | FK Osogovo | Academy Pandev | |||
| MKD D2 | 17/10/2026 15:00 | Pelister Bitola | FK Osogovo | |||
| MKD D2 | 10/10/2026 15:00 | FK Osogovo | FK Gorno Lisice | |||
| MKD D2 | 19/09/2026 13:45 | FK Teteks Tetovo | FK Osogovo | |||
| MKD D2 | 13/09/2026 14:00 | FK Osogovo | 0-1 (0-1) | FK Kozuv | L | |
| MKD CUP | 09/09/2026 14:00 | FK Osogovo | 1-3 (1-0) | Belasica Strumica | L | |
| MKD D2 | 05/09/2026 14:30 | Detonit Plachkovica | 2-1 (1-0) | FK Osogovo | L | |
| MKD D2 | 29/08/2026 14:45 | FK Osogovo | 0-0 (0-0) | FK Novaci | D | |
| MKD D2 | 22/08/2026 14:30 | Kamjani | 2-1 (2-1) | FK Osogovo | L | |
| MKD D2 | 15/08/2026 15:00 | Belasica Strumica | 1-0 (0-0) | FK Osogovo | L | |
| INT CF | 08/08/2026 16:00 | FK Osogovo | 2-1 (0-0) | FK Teteks Tetovo | W | |
| INT CF | 31/07/2026 15:30 | Rabotnicki Skopje | 2-1 (0-0) | FK Osogovo | L | |
| MKD D2 | 23/05/2026 14:30 | FK Novaci | 3-3 (2-1) | FK Osogovo | D | |
| MKD D2 | 16/05/2026 14:30 | FK Osogovo | 0-3 (0-2) | Bregalnica Stip | L | |
| MKD D2 | 10/05/2026 14:00 | Vardar Negotino | 0-4 (0-1) | FK Osogovo | W | |
| MKD D2 | 02/05/2026 14:00 | FK Osogovo | 0-1 (0-1) | FK Kozuv | L | |
| MKD D2 | 25/04/2026 14:00 | Pobeda Prilep | 1-8 (0-4) | FK Osogovo | W | |
| MKD D2 | 18/04/2026 13:30 | FK Osogovo | 2-1 (0-0) | FK Teteks Tetovo | W | |
| MKD D2 | 11/04/2026 13:30 | FK Osogovo | 1-1 (0-1) | Shkendija Haracine | D | |
| MKD D2 | 04/04/2026 13:30 | Belasica Strumica | 0-0 (0-0) | FK Osogovo | D | |
| MKD D2 | 28/03/2026 13:30 | FK Osogovo | 3-0 (1-0) | FK Sloga 1934 Vinica | W | |
| MKD D2 | 21/03/2026 13:30 | Detonit Plachkovica | 2-4 (2-2) | FK Osogovo | W | |
| MKD D2 | 14/03/2026 14:00 | FK Osogovo | 2-0 (1-0) | Golemo Konjari | W | |
| MKD D2 | 07/03/2026 13:00 | FK Skopje | 2-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 03/03/2026 13:00 | FK Osogovo | 1-0 (1-0) | FK Ohrid 2004 | W | |
| MKD D2 | 28/02/2026 13:00 | Prespa | 0-1 (0-0) | FK Osogovo | W | |
| MKD D2 | 21/02/2026 13:00 | FK Osogovo | 1-0 (0-0) | Kamenica-Sasa | W | |
| INT CF | 13/02/2026 14:00 | Pobeda Valandovo | FK Osogovo | |||
| INT CF | 07/02/2026 13:00 | FK Osogovo | 1-4 (1-2) | FC Vardar Skopje | L | |
| INT CF | 31/01/2026 12:00 | FK Osogovo | 0-3 (0-0) | Belasica Strumica | L | |
| INT CF | 24/01/2026 12:00 | FK Osogovo | 0-0 (0-0) | Detonit Plachkovica | D | |
| MKD D2 | 06/12/2025 12:00 | FK Osogovo | 0-0 (0-0) | FK Novaci | D | |
| MKD D2 | 25/11/2025 12:00 | Bregalnica Stip | 0-1 (0-1) | FK Osogovo | W | |
| MKD D2 | 21/11/2025 12:00 | FK Osogovo | 5-1 (3-0) | Vardar Negotino | W | |
| MKD D2 | 08/11/2025 12:00 | FK Kozuv | 0-0 (0-0) | FK Osogovo | D | |
| MKD D2 | 04/11/2025 12:40 | FK Osogovo | 6-0 (3-0) | Pobeda Prilep | W | |
| MKD D2 | 01/11/2025 12:30 | FK Teteks Tetovo | 3-0 (2-0) | FK Osogovo | L | |
| MKD D2 | 25/10/2025 12:00 | Shkendija Haracine | 1-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 11/10/2025 13:00 | FK Osogovo | 3-1 (1-0) | Belasica Strumica | W | |
| MKD D2 | 04/10/2025 13:00 | FK Sloga 1934 Vinica | 0-1 (0-0) | FK Osogovo | W | |
| MKD D2 | 27/09/2025 13:00 | FK Osogovo | 0-1 (0-0) | Detonit Plachkovica | L | |
| MKD D2 | 20/09/2025 13:30 | Golemo Konjari | 0-2 (0-1) | FK Osogovo | W | |
| MKD D2 | 13/09/2025 13:30 | FK Osogovo | 2-3 (1-0) | FK Skopje | L | |
| MKD D2 | 06/09/2025 14:00 | FK Ohrid 2004 | 2-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 30/08/2025 14:30 | FK Osogovo | 2-0 (0-0) | Prespa | W | |
| MKD D2 | 23/08/2025 15:00 | Kamenica-Sasa | 1-1 (0-1) | FK Osogovo | D | |
| INT CF | 16/08/2025 15:30 | Belasica Strumica | 1-0 (0-0) | FK Osogovo | L | |
| INT CF | 09/08/2025 15:30 | FK Osogovo | Detonit Plachkovica | |||
| INT CF | 06/08/2025 15:30 | FK Osogovo | Kamenica-Sasa | |||
| INT CF | 30/07/2025 16:00 | FK Osogovo | FK Teteks Tetovo | |||
| INT CF | 23/07/2025 16:00 | FK Osogovo | 1-1 (0-0) | Academy Pandev | D | |
| MKD D2 | 24/05/2025 15:00 | Shkendija Haracine | 2-1 (1-0) | FK Osogovo | L | |
| MKD D2 | 18/05/2025 15:00 | FK Osogovo | 4-0 (3-0) | Vardarski | W | |
| MKD D2 | 10/05/2025 15:00 | Kamenica-Sasa | 1-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 06/05/2025 15:00 | FK Osogovo | 2-0 (0-0) | FK Novaci | W | |
| MKD D2 | 03/05/2025 14:00 | Pobeda Prilep | 0-0 (0-0) | FK Osogovo | D | |
| MKD D2 | 26/04/2025 14:00 | FK Osogovo | 1-0 (0-0) | FK Bashkimi | W | |
| MKD D2 | 21/04/2025 14:00 | FK Ohrid 2004 | 2-2 (1-0) | FK Osogovo | D | |
| MKD D2 | 12/04/2025 14:00 | FK Osogovo | 0-0 (0-0) | Belasica Strumica | D | |
| MKD D2 | 05/04/2025 13:00 | KF Arsimi | 3-1 (0-0) | FK Osogovo | L | |
| MKD D2 | 29/03/2025 14:00 | FK Osogovo | 0-0 (0-0) | FK Makedonija Gjorce Petrov | D | |
| MKD D2 | 24/03/2025 14:00 | Borec Veles | 1-3 (0-1) | FK Osogovo | W | |
| MKD D2 | 08/03/2025 13:00 | FK Osogovo | 1-2 (0-1) | Bregalnica Stip | L | |
| MKD D2 | 04/03/2025 13:00 | Detonit Plachkovica | 0-1 (0-1) | FK Osogovo | W | |
| MKD D2 | 01/03/2025 13:00 | FK Osogovo | 0-0 (0-0) | FK Kozuv | D | |
| MKD D2 | 22/02/2025 13:00 | FK Skopje | 0-0 (0-0) | FK Osogovo | D | |
| MKD D2 | 15/02/2025 13:00 | Vardar Negotino | 1-0 (1-0) | FK Osogovo | L | |
| INT CF | 01/02/2025 13:00 | FK Osogovo | 1-2 (1-1) | FK Bashkimi | L | |
| MKD D2 | 07/12/2024 12:00 | Vardarski | 2-1 (0-0) | FK Osogovo | L | |
| MKD D2 | 30/11/2024 12:00 | FK Osogovo | 1-3 (0-2) | Kamenica-Sasa | L | |
| MKD D2 | 23/11/2024 12:00 | FK Novaci | 5-0 (3-0) | FK Osogovo | L | |
| MKD D2 | 10/11/2024 12:00 | FK Osogovo | 4-1 (2-1) | Pobeda Prilep | W | |
| MKD D2 | 02/11/2024 12:00 | FK Bashkimi | 5-1 (3-0) | FK Osogovo | L | |
| MKD D2 | 29/10/2024 12:00 | FK Osogovo | 0-2 (0-0) | FK Ohrid 2004 | L | |
| MKD D2 | 26/10/2024 11:00 | Belasica Strumica | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 19/10/2024 12:00 | FK Osogovo | 1-2 (0-1) | KF Arsimi | L | |
| MKD D2 | 06/10/2024 12:00 | FK Makedonija Gjorce Petrov | 2-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 28/09/2024 11:50 | FK Osogovo | 1-0 (0-0) | Borec Veles | W | |
| MKD D2 | 25/09/2024 13:00 | FK Osogovo | 1-3 (1-1) | Detonit Plachkovica | L | |
| MKD D2 | 22/09/2024 13:00 | Bregalnica Stip | 1-1 (0-0) | FK Osogovo | D | |
| MKD D2 | 01/09/2024 14:00 | FK Kozuv | 4-1 (2-1) | FK Osogovo | L | |
| MKD D2 | 24/08/2024 14:00 | FK Osogovo | 1-1 (0-1) | FK Skopje | D | |
| MKD D2 | 17/08/2024 15:00 | FK Osogovo | 1-2 (1-1) | Vardar Negotino | L | |
| INT CF | 10/08/2024 15:30 | FK Osogovo | 1-2 (1-1) | Vardarski | L | |
| INT CF | 07/08/2024 15:30 | FK Sloga 1934 Vinica | 1-2 (1-1) | FK Osogovo | W | |
| INT CF | 01/08/2024 15:30 | Kamenica-Sasa | 2-1 (0-1) | FK Osogovo | L | |
| INT CF | 27/07/2024 15:30 | Bregalnica Stip | 1-3 (0-0) | FK Osogovo | W | |
| MKD D2 | 19/05/2024 14:50 | FK Osogovo | 3-0 (0-0) | Pelister Bitola | W | |
| MKD D2 | 11/05/2024 15:00 | KF Arsimi | 2-2 (1-0) | FK Osogovo | D | |
| MKD D2 | 04/05/2024 11:00 | FK Osogovo | 2-1 (0-1) | FK Skopje | W | |
| MKD D2 | 30/04/2024 14:00 | Vardar Negotino | 3-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 27/04/2024 14:00 | FK Osogovo | 2-1 (1-0) | FK Karaorman | W | |
| MKD D2 | 20/04/2024 14:00 | FK Kozuv | 2-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 13/04/2024 13:00 | FK Osogovo | 1-3 (0-1) | Detonit Plachkovica | L | |
| MKD D2 | 06/04/2024 13:00 | Kamenica-Sasa | 2-1 (1-0) | FK Osogovo | L | |
| MKD D2 | 30/03/2024 14:00 | FK Osogovo | 1-0 (0-0) | FK Novaci | W | |
| MKD D2 | 17/03/2024 14:00 | Belasica Strumica | 1-1 (0-1) | FK Osogovo | D | |
| MKD D2 | 09/03/2024 13:00 | FK Ohrid 2004 | 5-0 (2-0) | FK Osogovo | L | |
| MKD D2 | 05/03/2024 13:00 | FK Osogovo | 0-0 (0-0) | Pobeda Prilep | D | |
| MKD D2 | 02/03/2024 13:00 | FK Bashkimi | 2-1 (0-1) | FK Osogovo | L | |
| MKD D2 | 24/02/2024 13:00 | FK Osogovo | 4-0 (2-0) | FK Teteks Tetovo | W | |
| MKD D2 | 17/02/2024 13:00 | KF Besa Doberdoll | 3-0 (1-0) | FK Osogovo | L | |
| INT CF | 06/02/2024 13:00 | FK Osogovo | 0-2 (0-1) | FK Kozuv | L | |
| MKD D2 | 09/12/2023 12:00 | Pelister Bitola | 2-1 (1-1) | FK Osogovo | L | |
| MKD D2 | 02/12/2023 12:00 | FK Osogovo | 1-1 (0-1) | KF Arsimi | D | |
| MKD D2 | 27/11/2023 12:00 | FK Skopje | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 12/11/2023 12:00 | FK Osogovo | 2-2 (0-1) | Vardar Negotino | D | |
| MKD D2 | 04/11/2023 12:00 | FK Karaorman | 2-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 28/10/2023 11:00 | FK Osogovo | 3-2 (2-0) | FK Kozuv | W | |
| MKD D2 | 21/10/2023 12:00 | Detonit Plachkovica | 3-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 07/10/2023 12:00 | FK Osogovo | 1-1 (1-0) | Kamenica-Sasa | D | |
| MKD D2 | 30/09/2023 12:00 | FK Novaci | 1-2 (0-1) | FK Osogovo | W | |
| MKD D2 | 23/09/2023 13:00 | FK Osogovo | 3-1 (2-0) | Belasica Strumica | W | |
| MKD D2 | 16/09/2023 13:00 | FK Osogovo | 0-3 (0-2) | FK Ohrid 2004 | L | |
| MKD D2 | 03/09/2023 14:00 | Pobeda Prilep | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 26/08/2023 14:00 | FK Osogovo | 2-3 (1-1) | FK Bashkimi | L | |
| MKD D2 | 19/08/2023 15:00 | FK Teteks Tetovo | 2-1 (1-1) | FK Osogovo | L | |
| MKD D2 | 12/08/2023 15:00 | FK Osogovo | 0-4 (0-2) | KF Besa Doberdoll | L | |
| INT CF | 04/02/2023 12:00 | FK Osogovo | 3-0 (2-0) | FK Sloga 1934 Vinica | W | |
| MKD D2 | 14/05/2022 15:00 | Bratstvo 07 | FK Osogovo | |||
| MKD D2 | 07/05/2022 15:00 | FK Osogovo | Detonit Junior | |||
| MKD D2 | 30/04/2022 15:00 | FK Kozuv | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 23/04/2022 14:00 | FK Osogovo | FK Sloga 1934 Vinica | |||
| MKD D2 | 02/04/2022 13:00 | Kamenica-Sasa | FK Osogovo | |||
| MKD D2 | 20/03/2022 14:00 | FK Osogovo | Pehchevo | |||
| MKD D2 | 12/03/2022 14:00 | FK Osogovo | FK Lokomotiva Gradsko | |||
| MKD D2 | 05/03/2022 13:00 | FK Osogovo | FK Kozuv | |||
| MKD D2 | 26/02/2022 13:00 | Pehchevo | 0-1 (0-0) | FK Osogovo | W | |
| MKD D2 | 19/02/2022 13:00 | FK Osogovo | 0-3 (0-2) | Belasica Strumica | L | |
| MKD D2 | 14/12/2021 12:00 | Detonit Junior | 0-0 (0-0) | FK Osogovo | D | |
| MKD D2 | 07/12/2021 12:00 | FK Osogovo | 1-3 (0-1) | Pobeda Prilep | L | |
| MKD D2 | 04/12/2021 12:00 | FK Lokomotiva Gradsko | 1-1 (1-0) | FK Osogovo | D | |
| MKD D2 | 27/11/2021 12:00 | Bratstvo 07 | 2-4 (1-1) | FK Osogovo | W | |
| MKD D2 | 20/11/2021 12:00 | FK Osogovo | 3-0 (0-0) | FK Sloga 1934 Vinica | W | |
| MKD D2 | 07/11/2021 12:00 | Kamenica-Sasa | 2-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 30/10/2021 12:00 | FK Kozuv | 1-1 (0-0) | FK Osogovo | D | |
| MKD D2 | 23/10/2021 12:00 | FK Osogovo | 0-3 (0-1) | Pehchevo | L | |
| MKD D2 | 16/10/2021 12:00 | Belasica Strumica | 0-2 (0-1) | FK Osogovo | W | |
| MKD D2 | 03/10/2021 13:00 | FK Osogovo | 2-1 (2-1) | Detonit Junior | W | |
| MKD D2 | 25/09/2021 13:00 | Pobeda Prilep | 6-0 (4-0) | FK Osogovo | L | |
| MKD D2 | 18/09/2021 13:00 | FK Osogovo | 2-2 (0-0) | FK Lokomotiva Gradsko | D | |
| MKD D2 | 12/09/2021 14:00 | FK Osogovo | 2-0 (0-0) | Bratstvo 07 | W | |
| MKD D2 | 29/08/2021 14:00 | FK Sloga 1934 Vinica | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 25/08/2021 14:00 | FK Osogovo | 1-4 (1-2) | Kamenica-Sasa | L | |
| INT CF | 08/08/2021 12:00 | FK Osogovo | 1-0 (0-0) | FC Plackovica | W | |
| INT CF | 05/08/2021 15:30 | FK Osogovo | 1-6 (0-0) | FK Trajal Krusevac | L | |
| INT CF | 28/07/2021 14:00 | Pehchevo | 0-0 (0-0) | FK Osogovo | D | |
| INT CF | 25/07/2021 18:00 | Belasica Strumica | 0-1 (0-0) | FK Osogovo | W | |
| MKD D2 | 15/05/2021 14:00 | FC Plackovica | 2-0 (2-0) | FK Osogovo | L | |
| MKD D2 | 08/05/2021 14:00 | FK Osogovo | 0-1 (0-1) | Pobeda Prilep | L | |
| MKD D2 | 01/05/2021 11:00 | FK Sloga 1934 Vinica | 4-1 (2-1) | FK Osogovo | L | |
| MKD D2 | 24/04/2021 11:00 | FK Osogovo | 0-2 (0-1) | Bregalnica Stip | L | |
| MKD D2 | 17/04/2021 11:00 | FK Tikves Kavadarci | 3-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 10/04/2021 11:00 | FK Osogovo | 0-1 (0-0) | Pehchevo | L | |
| MKD D2 | 03/04/2021 13:00 | FK Kozuv | 0-1 (0-0) | FK Osogovo | W | |
| MKD D2 | 21/03/2021 14:00 | FK Osogovo | 0-2 (0-1) | Kamenica-Sasa | L | |
| MKD D2 | 13/03/2021 14:00 | FK Osogovo | 4-1 (4-0) | FK Roseman | W | |
| MKD D2 | 06/03/2021 13:00 | FC Plackovica | 0-1 (0-0) | FK Osogovo | W | |
| MKD D2 | 27/02/2021 13:00 | FK Osogovo | 1-1 (0-1) | Kamenica-Sasa | D | |
| INT CF | 30/01/2021 12:00 | Bregalnica Stip | 2-1 (2-0) | FK Osogovo | L | |
| MKD D2 | 12/12/2020 12:00 | FK Roseman | 1-7 (0-2) | FK Osogovo | W | |
| MKD D2 | 05/12/2020 12:00 | FK Osogovo | 2-0 (1-0) | Pobeda Prilep | W | |
| MKD D2 | 28/11/2020 12:00 | FK Sloga 1934 Vinica | 3-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 25/11/2020 12:00 | FK Osogovo | 1-3 (1-3) | Bregalnica Stip | L | |
| MKD D2 | 21/11/2020 12:00 | FK Tikves Kavadarci | 3-1 (1-1) | FK Osogovo | L | |
| MKD D2 | 14/11/2020 12:00 | FK Osogovo | 1-0 (0-0) | Pehchevo | W | |
| MKD D2 | 08/11/2020 12:30 | FK Osogovo | 0-0 (0-0) | FK Kozuv | D | |
| MKD D2 | 24/10/2020 12:30 | FK Osogovo | 1-1 (1-1) | FC Plackovica | D | |
| MKD D2 | 17/10/2020 12:30 | Kamenica-Sasa | 0-0 (0-0) | FK Osogovo | D | |
| MKD D2 | 10/10/2020 13:00 | FK Osogovo | 5-4 (2-2) | FK Roseman | W | |
| MKD D2 | 04/10/2020 13:00 | Pobeda Prilep | 1-1 (1-1) | FK Osogovo | D | |
| MKD D2 | 26/09/2020 13:30 | FK Osogovo | 1-1 (0-1) | FK Sloga 1934 Vinica | D | |
| MKD D2 | 19/09/2020 17:00 | Bregalnica Stip | 1-1 (0-0) | FK Osogovo | D | |
| MKD D2 | 12/09/2020 14:00 | FK Osogovo | 0-3 (0-1) | FK Tikves Kavadarci | L | |
| MKD D2 | 30/08/2020 14:30 | Pehchevo | 3-3 (0-0) | FK Osogovo | D | |
| MKD D2 | 22/08/2020 15:00 | FK Kozuv | 2-0 (0-0) | FK Osogovo | L | |
| INT CF | 14/07/2020 15:59 | Academy Pandev | 3-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 22/03/2020 15:00 | Kamenica-Sasa | FK Osogovo | |||
| MKD D2 | 14/03/2020 13:30 | FK Osogovo | FC Plackovica | |||
| MKD D2 | 07/03/2020 13:00 | FK Kozuv | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 29/02/2020 13:00 | FK Osogovo | 0-2 (0-0) | Belasica Strumica | L | |
| INT CF | 12/02/2020 13:40 | FK Kozuv | 3-1 (2-0) | FK Osogovo | L | |
| INT CF | 02/02/2020 12:30 | Kamenica-Sasa | 2-2 (1-0) | FK Osogovo | D | |
| MKD D2 | 30/11/2019 12:00 | Pobeda Prilep | 5-1 (3-1) | FK Osogovo | L | |
| MKD D2 | 23/11/2019 12:00 | FK Osogovo | 1-2 (0-1) | Pehchevo | L | |
| MKD D2 | 10/11/2019 12:00 | FK Tikves Kavadarci | 7-1 (4-0) | FK Osogovo | L | |
| MKD D2 | 02/11/2019 12:30 | FK Osogovo | 1-2 (1-0) | Bregalnica Stip | L | |
| MKD CUP | 30/10/2019 12:30 | FK Osogovo | 1-4 (1-1) | Academy Pandev | L | |
| MKD D2 | 26/10/2019 12:30 | PTGL | 1-3 (1-1) | FK Osogovo | W | |
| MKD D2 | 20/10/2019 12:30 | FK Osogovo | 2-5 (0-2) | Kamenica-Sasa | L | |
| MKD D2 | 11/10/2019 13:00 | FC Plackovica | 2-1 (1-1) | FK Osogovo | L | |
| MKD D2 | 06/10/2019 13:00 | FK Osogovo | 0-4 (0-2) | FK Kozuv | L | |
| MKD D2 | 28/09/2019 13:00 | Belasica Strumica | 3-0 (1-0) | FK Osogovo | L | |
| MKD CUP | 25/09/2019 13:30 | Academy Pandev | 3-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 21/09/2019 13:30 | FK Osogovo | 1-0 (1-0) | Pobeda Prilep | W | |
| MKD D2 | 15/09/2019 13:30 | Pehchevo | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 07/09/2019 14:00 | FK Osogovo | 0-1 (0-0) | FK Tikves Kavadarci | L | |
| MKD D2 | 31/08/2019 17:00 | Bregalnica Stip | 5-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 24/08/2019 15:00 | FK Osogovo | 1-3 (0-1) | PTGL | L | |
| MKD CUP | 21/08/2019 15:00 | FK Osogovo | 1-0 (1-0) | Pobeda Prilep | W | |
| INT CF | 14/08/2019 15:30 | FK Osogovo | 2-0 (1-0) | Kamenica-Sasa | W | |
| INT CF | 31/07/2019 16:05 | Belasica Strumica | 2-1 (0-0) | FK Osogovo | L | |
| MKD CUP | 22/08/2018 15:00 | FK Osogovo | 0-1 (0-0) | Pelister Bitola | L | |
| MKD D2 | 19/05/2018 14:30 | FK Osogovo | 1-2 (1-0) | FK Kozuv | L | |
| MKD D2 | 12/05/2018 14:30 | FK Tikves Kavadarci | 2-1 (1-1) | FK Osogovo | L | |
| MKD D2 | 28/04/2018 14:00 | Pobeda Valandovo | 3-5 (1-3) | FK Osogovo | W | |
| MKD D2 | 24/04/2018 14:00 | FC Plackovica | 3-2 (2-1) | FK Osogovo | L | |
| MKD D2 | 21/04/2018 14:00 | FK Osogovo | 1-0 (1-0) | Kamenica-Sasa | W | |
| MKD D2 | 17/04/2018 14:00 | Belasica Strumica | 5-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 14/04/2018 14:00 | FK Osogovo | 0-0 (0-0) | Bregalnica Stip | D | |
| MKD D2 | 07/04/2018 14:00 | Borec Veles | 1-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 31/03/2018 13:00 | FK Osogovo | 2-2 (1-1) | Bregalnica Stip | D | |
| MKD D2 | 18/03/2018 13:00 | Borec Veles | 2-1 (0-0) | FK Osogovo | L | |
| MKD D2 | 10/03/2018 13:00 | FK Osogovo | 4-0 (2-0) | Pobeda Valandovo | W | |
| INT CF | 21/02/2018 13:35 | FK Osogovo | 1-2 (1-0) | FK Kit Go Pehcevo | L | |
| INT CF | 07/02/2018 12:40 | Pobeda Prilep | 1-1 (0-0) | FK Osogovo | D | |
| MKD D2 | 25/11/2017 12:00 | Kamenica-Sasa | 2-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 18/11/2017 12:00 | FK Osogovo | 0-0 (0-0) | Belasica Strumica | D | |
| MKD D2 | 11/11/2017 12:00 | FC Plackovica | 2-0 (0-0) | FK Osogovo | L | |
| MKD D2 | 04/11/2017 12:30 | FK Osogovo | 0-4 (0-1) | FK Tikves Kavadarci | L | |
| MKD D2 | 28/10/2017 11:30 | FK Kozuv | 2-1 (0-0) | FK Osogovo | L | |
| MKD D2 | 21/10/2017 12:30 | Bregalnica Stip | 5-0 (3-0) | FK Osogovo | L | |
| MKD D2 | 14/10/2017 12:30 | FK Osogovo | 1-2 (0-1) | Borec Veles | L | |
| MKD D2 | 07/10/2017 12:30 | Pobeda Valandovo | 3-0 (1-0) | FK Osogovo | L | |
| MKD D2 | 01/10/2017 13:00 | FK Osogovo | Horizont Turnovo | |||
| MKD D2 | 26/09/2017 13:30 | FK Osogovo | 2-2 (0-2) | Kamenica-Sasa | D | |
| MKD D2 | 23/09/2017 17:30 | Belasica Strumica | 5-0 (2-0) | FK Osogovo | L | |
| MKD D2 | 16/09/2017 13:30 | FK Osogovo | 2-1 (0-0) | FC Plackovica | W | |
| MKD D2 | 09/09/2017 14:00 | FK Tikves Kavadarci | 2-1 (0-0) | FK Osogovo | L | |
| MKD D2 | 27/08/2017 14:30 | FK Osogovo | 1-0 (0-0) | FK Kozuv | W | |
| MKD CUP | 16/08/2017 15:00 | FK Osogovo | 1-2 (1-2) | Bregalnica Stip | L | |
| INT CF | 03/08/2017 15:59 | Pobeda Prilep | 2-0 (0-0) | FK Osogovo | L | |
| MKD CUP | 29/09/2010 12:30 | FK Tikves Kavadarci | 0-1 (0-0) | FK Osogovo | W | |
| MKD CUP | 15/09/2010 13:30 | FK Osogovo | 0-3 (0-0) | FK Tikves Kavadarci | L | |
| MKD CUP | 18/08/2010 15:00 | FK Osogovo | 6-0 (0-0) | Prevalec | W |
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