| 2026-05-23 16:30:41May 23, 2026 | Novaci  | 3 - 3 |  Osogovo | 16:30:4116:30 | N/A |
| 2026-05-16 16:30:26May 16, 2026 | Osogovo | 0 - 3 | Bregalnica | 16:30:2616:30 | N/A |
| 2026-05-10 16:00:39May 10, 2026 | Vardar (N)  | 0 - 4 | Osogovo | 16:00:3916:00 | N/A |
| 2026-05-02 16:00:53May 2, 2026 | Osogovo | 0 - 1 |  Kozhuf | 16:00:5316:00 | N/A |
| 2026-04-25 16:00:16April 25, 2026 | Pobeda (2010)  | 1 - 8 | Osogovo | 16:00:1616:00 | N/A |
| 2026-04-18 15:30:00April 18, 2026 | Osogovo | 2 - 1 |  Teteks | 15:30:0015:30 | N/A |
| 2026-04-11 15:30:00April 11, 2026 | Osogovo | 1 - 1 |  Shkëndija 77 | 15:30:0015:30 | N/A |
| 2026-04-04 15:30:00April 4, 2026 | Belasica | 0 - 0 | Osogovo | 15:30:0015:30 | N/A |
| 2026-03-28 14:30:00March 28, 2026 | Osogovo | 3 - 0 |  Sloga 1934 | 14:30:0014:30 | N/A |
| 2026-03-21 14:30:00March 21, 2026 | Detonit Plachkovica  | 2 - 4 | Osogovo | 14:30:0014:30 | N/A |
| 2026-03-14 14:30:00March 14, 2026 | Osogovo | 2 - 0 |  Golemo Konjari | 14:30:0014:30 | N/A |
| 2026-03-07 14:00:00March 7, 2026 | Skopje | 2 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2026-03-03 14:00:00March 3, 2026 | Osogovo | 1 - 0 | Ohrid Lychnidos | 14:00:0014:00 | N/A |
| 2026-02-28 14:00:00February 28, 2026 | Prespa  | 0 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2026-02-21 14:00:00February 21, 2026 | Osogovo | 1 - 0 |  Sasa | 14:00:0014:00 | N/A |
| 2026-02-13 15:00:44February 13, 2026 | Pobeda (V) | 1 - 2 | Osogovo | 15:00:4415:00 | N/A |
| 2026-02-07 14:00:34February 7, 2026 | Osogovo | 1 - 4 | Vardar | 14:00:3414:00 | N/A |
| 2026-01-31 13:00:52January 31, 2026 | Osogovo | 0 - 3 | Belasica | 13:00:5213:00 | N/A |
| 2026-01-28 13:30:57January 28, 2026 | Aerodrom | 0 - 5 | Osogovo | 13:30:5713:30 | N/A |
| 2026-01-24 13:00:06January 24, 2026 | Osogovo | 0 - 0 | Detonit Plachkovica | 13:00:0613:00 | N/A |
| 2025-12-06 13:00:00December 6, 2025 | Osogovo | 0 - 0 | Novaci | 13:00:0013:00 | N/A |
| 2025-11-25 13:00:00November 25, 2025 | Bregalnica | 0 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2025-11-21 13:00:00November 21, 2025 | Osogovo | 5 - 1 | Vardar (N) | 13:00:0013:00 | N/A |
| 2025-11-08 13:00:00November 8, 2025 | Kozhuf | 0 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2025-11-04 13:30:00November 4, 2025 | Osogovo | 6 - 0 | Pobeda (2010) | 13:30:0013:30 | N/A |
| 2025-11-01 13:30:00November 1, 2025 | Teteks | 3 - 0 | Osogovo | 13:30:0013:30 | N/A |
| 2025-10-25 14:00:00October 25, 2025 | Shkëndija 77 | 1 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2025-10-17 15:00:36October 17, 2025 | Osogovo | - | Brera Strumica | 15:00:3615:00 | N/A |
| 2025-10-11 15:00:00October 11, 2025 | Osogovo | 3 - 1 | Belasica | 15:00:0015:00 | N/A |
| 2025-10-04 15:00:00October 4, 2025 | Sloga 1934 | 0 - 1 | Osogovo | 15:00:0015:00 | N/A |
| 2025-09-27 15:00:00September 27, 2025 | Osogovo | 0 - 1 | Detonit Plachkovica | 15:00:0015:00 | N/A |
| 2025-09-20 15:30:00September 20, 2025 | Golemo Konjari | 0 - 2 | Osogovo | 15:30:0015:30 | N/A |
| 2025-09-13 15:30:00September 13, 2025 | Osogovo | 2 - 3 | Skopje | 15:30:0015:30 | N/A |
| 2025-09-06 16:00:00September 6, 2025 | Ohrid Lychnidos | 2 - 0 | Osogovo | 16:00:0016:00 | N/A |
| 2025-08-30 16:30:00August 30, 2025 | Osogovo | 2 - 0 | Prespa | 16:30:0016:30 | N/A |
| 2025-08-23 17:00:45August 23, 2025 | Sasa | 1 - 1 | Osogovo | 17:00:4517:00 | N/A |
| 2025-08-16 17:30:56August 16, 2025 | Osogovo | 1 - 0 | Belasica | 17:30:5617:30 | N/A |
| 2025-08-09 17:30:58August 9, 2025 | Osogovo | 1 - 0 | Detonit Plachkovica | 17:30:5817:30 | N/A |
| 2025-08-06 17:00:33August 6, 2025 | Osogovo | - | Sasa | 17:00:33Canceled | N/A |
| 2025-07-30 18:00:12July 30, 2025 | Osogovo | 1 - 2 | Teteks | 18:00:1218:00 | N/A |
| 2025-07-26 18:00:49July 26, 2025 | Vardar (N) | 0 - 2 | Osogovo | 18:00:4918:00 | N/A |
| 2025-07-23 18:00:24July 23, 2025 | Osogovo | 1 - 1 | Brera Strumica | 18:00:2418:00 | N/A |
| 2025-05-24 17:00:54May 24, 2025 | Osogovo | 1 - 2 | Shkëndija 77 | 17:00:5417:00 | N/A |
| 2025-05-18 17:00:56May 18, 2025 | Osogovo | 4 - 0 | Vardarski | 17:00:5617:00 | N/A |
| 2025-05-10 17:00:30May 10, 2025 | Sasa | 1 - 0 | Osogovo | 17:00:3017:00 | N/A |
| 2025-05-06 17:00:16May 6, 2025 | Osogovo | 2 - 0 | Novaci | 17:00:1617:00 | N/A |
| 2025-05-03 16:00:48May 3, 2025 | Pobeda (2010) | 0 - 0 | Osogovo | 16:00:4816:00 | N/A |
| 2025-04-26 16:00:00April 26, 2025 | Osogovo | 1 - 0 | Bashkimi | 16:00:0016:00 | N/A |
| 2025-04-21 16:00:00April 21, 2025 | Ohrid Lychnidos | 2 - 2 | Osogovo | 16:00:0016:00 | N/A |
| 2025-04-12 16:00:00April 12, 2025 | Osogovo | 0 - 0 | Belasica | 16:00:0016:00 | N/A |
| 2025-04-05 15:00:00April 5, 2025 | Arsimi | 3 - 1 | Osogovo | 15:00:0015:00 | N/A |
| 2025-03-29 15:00:00March 29, 2025 | Osogovo | 0 - 0 | Makedonija GjP | 15:00:0015:00 | N/A |
| 2025-03-24 15:00:00March 24, 2025 | Borec | 1 - 3 | Osogovo | 15:00:0015:00 | N/A |
| 2025-03-08 14:00:00March 8, 2025 | Osogovo | 1 - 2 | Bregalnica | 14:00:0014:00 | N/A |
| 2025-03-04 14:00:00March 4, 2025 | Detonit Plachkovica | 0 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2025-03-01 14:00:00March 1, 2025 | Osogovo | 0 - 0 | Kozhuf | 14:00:0014:00 | N/A |
| 2025-02-22 14:00:00February 22, 2025 | Skopje | 0 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2025-02-15 14:00:00February 15, 2025 | Vardar (N) | 1 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2025-02-08 14:00:50February 8, 2025 | BVK Konjare | 0 - 3 | Osogovo | 14:00:5014:00 | N/A |
| 2025-02-01 14:00:25February 1, 2025 | Osogovo | 1 - 2 | Bashkimi | 14:00:2514:00 | N/A |
| 2025-01-26 13:00:12January 26, 2025 | Aerodrom | 2 - 1 | Osogovo | 13:00:1213:00 | N/A |
| 2025-01-22 14:00:38January 22, 2025 | Osogovo | 0 - 1 | Sasa | 14:00:3814:00 | N/A |
| 2024-12-07 13:00:00December 7, 2024 | Vardarski | 2 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2024-11-30 13:00:00November 30, 2024 | Osogovo | 1 - 3 | Sasa | 13:00:0013:00 | N/A |
| 2024-11-23 13:00:00November 23, 2024 | Novaci | 5 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2024-11-10 13:00:00November 10, 2024 | Osogovo | 4 - 1 | Pobeda (2010) | 13:00:0013:00 | N/A |
| 2024-11-02 13:00:00November 2, 2024 | Bashkimi | 5 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2024-10-29 13:00:00October 29, 2024 | Osogovo | 0 - 2 | Ohrid Lychnidos | 13:00:0013:00 | N/A |
| 2024-10-26 13:00:00October 26, 2024 | Belasica | 1 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2024-10-19 14:00:00October 19, 2024 | Osogovo | 1 - 2 | Arsimi | 14:00:0014:00 | N/A |
| 2024-10-06 14:00:00October 6, 2024 | Makedonija GjP | 2 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2024-09-28 14:00:00September 28, 2024 | Osogovo | 1 - 0 | Borec | 14:00:0014:00 | N/A |
| 2024-09-25 15:00:00September 25, 2024 | Osogovo | 1 - 3 | Detonit Plachkovica | 15:00:0015:00 | N/A |
| 2024-09-22 15:00:00September 22, 2024 | Bregalnica | 1 - 1 | Osogovo | 15:00:0015:00 | N/A |
| 2024-09-07 16:00:40September 7, 2024 | Brera Strumica | 2 - 0 | Osogovo | 16:00:4016:00 | N/A |
| 2024-09-01 16:00:00September 1, 2024 | Kozhuf | 4 - 1 | Osogovo | 16:00:0016:00 | N/A |
| 2024-08-24 16:00:00August 24, 2024 | Osogovo | 1 - 1 | Skopje | 16:00:0016:00 | N/A |
| 2024-08-17 17:00:25August 17, 2024 | Osogovo | 1 - 2 | Vardar (N) | 17:00:2517:00 | N/A |
| 2024-08-10 17:30:01August 10, 2024 | Osogovo | 1 - 2 | Vardarski | 17:30:0117:30 | N/A |
| 2024-08-07 17:30:39August 7, 2024 | Sloga 1934 | 1 - 2 | Osogovo | 17:30:3917:30 | N/A |
| 2024-08-01 17:30:43August 1, 2024 | Osogovo | 1 - 2 | Sasa | 17:30:4317:30 | N/A |
| 2024-07-27 18:00:44July 27, 2024 | Bregalnica | 1 - 3 | Osogovo | 18:00:4418:00 | N/A |
| 2024-07-23 17:30:46July 23, 2024 | Borec | 2 - 2 | Osogovo | 17:30:4617:30 | N/A |
| 2024-05-19 17:00:00May 19, 2024 | Osogovo | 3 - 0 | Pelister | 17:00:0017:00 | N/A |
| 2024-05-11 17:00:00May 11, 2024 | Arsimi | 2 - 2 | Osogovo | 17:00:0017:00 | N/A |
| 2024-05-04 13:00:00May 4, 2024 | Osogovo | 2 - 1 | Skopje | 13:00:0013:00 | N/A |
| 2024-04-30 16:00:00April 30, 2024 | Vardar (N) | 3 - 0 | Osogovo | 16:00:0016:00 | N/A |
| 2024-04-27 16:00:00April 27, 2024 | Osogovo | 2 - 1 | Karaorman | 16:00:0016:00 | N/A |
| 2024-04-20 16:00:00April 20, 2024 | Kozhuf | 2 - 0 | Osogovo | 16:00:0016:00 | N/A |
| 2024-04-13 15:00:00April 13, 2024 | Osogovo | 1 - 3 | Detonit Plachkovica | 15:00:0015:00 | N/A |
| 2024-04-06 15:00:00April 6, 2024 | Sasa | 2 - 1 | Osogovo | 15:00:0015:00 | N/A |
| 2024-03-30 15:00:00March 30, 2024 | Osogovo | 1 - 0 | Novaci | 15:00:0015:00 | N/A |
| 2024-03-17 15:00:00March 17, 2024 | Belasica | 1 - 1 | Osogovo | 15:00:0015:00 | N/A |
| 2024-03-09 14:00:00March 9, 2024 | Ohrid Lychnidos | 5 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2024-03-05 14:00:00March 5, 2024 | Osogovo | 0 - 0 | Pobeda (2010) | 14:00:0014:00 | N/A |
| 2024-03-02 14:00:00March 2, 2024 | Bashkimi | 2 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2024-02-24 14:00:00February 24, 2024 | Osogovo | 4 - 0 | Teteks | 14:00:0014:00 | N/A |
| 2024-02-18 14:00:00February 18, 2024 | Besa (DD)  | 3 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2023-12-09 13:00:00December 9, 2023 | Pelister | 2 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2023-12-02 13:00:00December 2, 2023 | Osogovo | 1 - 1 | Arsimi | 13:00:0013:00 | N/A |
| 2023-11-27 13:00:00November 27, 2023 | Skopje | 1 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2023-11-12 13:00:00November 12, 2023 | Osogovo | 2 - 2 | Vardar (N) | 13:00:0013:00 | N/A |
| 2023-11-04 13:00:00November 4, 2023 | Karaorman | 2 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2023-10-28 13:00:00October 28, 2023 | Osogovo | 3 - 2 | Kozhuf | 13:00:0013:00 | N/A |
| 2023-10-21 14:00:00October 21, 2023 | Detonit Plachkovica | 3 - 0 | Osogovo | 14:00:0014:00 | N/A |
| 2023-10-07 14:00:00October 7, 2023 | Osogovo | 1 - 1 | Sasa | 14:00:0014:00 | N/A |
| 2023-09-30 14:00:00September 30, 2023 | Novaci | 1 - 2 | Osogovo | 14:00:0014:00 | N/A |
| 2023-09-23 15:00:00September 23, 2023 | Osogovo | 3 - 1 | Belasica | 15:00:0015:00 | N/A |
| 2023-09-16 15:00:00September 16, 2023 | Osogovo | 0 - 3 | Ohrid Lychnidos | 15:00:0015:00 | N/A |
| 2023-09-03 16:00:00September 3, 2023 | Pobeda (2010) | 1 - 0 | Osogovo | 16:00:0016:00 | N/A |
| 2023-08-26 16:00:00August 26, 2023 | Osogovo | 2 - 3 | Bashkimi | 16:00:0016:00 | N/A |
| 2023-08-19 17:00:00August 19, 2023 | Teteks | 2 - 1 | Osogovo | 17:00:0017:00 | N/A |
| 2023-08-12 17:00:51August 12, 2023 | Osogovo | 0 - 4 | Besa (DD) | 17:00:5117:00 | N/A |
| 2023-05-28 17:00:47May 28, 2023 | Teteks | 6 - 1 | Osogovo | 17:00:4717:00 | N/A |
| 2023-05-14 17:00:00May 14, 2023 | Osogovo | 2 - 0 |  Tiverija | 17:00:0017:00 | N/A |
| 2023-05-07 17:00:00May 7, 2023 | Vardarski | 1 - 0 | Osogovo | 17:00:0017:00 | N/A |
| 2023-04-29 17:00:00April 29, 2023 | Bregalnica 1926 | 2 - 2 | Osogovo | 17:00:0017:00 | N/A |
| 2023-04-23 16:00:00April 23, 2023 | Osogovo | 2 - 0 | Karbinci | 16:00:0016:00 | N/A |
| 2023-04-14 16:00:00April 14, 2023 | Rudar | 3 - 1 | Osogovo | 16:00:0016:00 | N/A |
| 2023-04-09 15:00:00April 9, 2023 | Osogovo | 2 - 0 | Ovche Pole | 15:00:0015:00 | N/A |
| 2023-04-02 15:00:00April 2, 2023 | Atletiko | 1 - 3 | Osogovo | 15:00:0015:00 | N/A |
| 2023-03-26 15:00:00March 26, 2023 | Osogovo | 2 - 1 | Spartmani | 15:00:0015:00 | N/A |
| 2023-03-19 15:00:00March 19, 2023 | Dojransko Ezero  | 1 - 2 | Osogovo | 15:00:0015:00 | N/A |
| 2023-03-12 14:00:00March 12, 2023 | Osogovo | 2 - 0 | Malesh | 14:00:0014:00 | N/A |
| 2022-11-20 13:00:00November 20, 2022 | Tiverija | 0 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2022-11-13 13:00:00November 13, 2022 | Osogovo | 9 - 0 | Vardarski | 13:00:0013:00 | N/A |
| 2022-11-06 13:00:00November 6, 2022 | Osogovo | 3 - 2 | Bregalnica 1926 | 13:00:0013:00 | N/A |
| 2022-10-30 13:00:00October 30, 2022 | Karbinci | 1 - 6 | Osogovo | 13:00:0013:00 | N/A |
| 2022-10-23 13:00:00October 23, 2022 | Osogovo | 3 - 0 | Rudar | 13:00:0013:00 | N/A |
| 2022-10-16 14:00:00October 16, 2022 | Ovche Pole | 2 - 4 | Osogovo | 14:00:0014:00 | N/A |
| 2022-10-09 14:00:00October 9, 2022 | Osogovo | 3 - 2 | Atletiko | 14:00:0014:00 | N/A |
| 2022-10-02 15:00:00October 2, 2022 | Spartmani | 0 - 3 | Osogovo | 15:00:0015:00 | N/A |
| 2022-09-25 15:00:00September 25, 2022 | Osogovo | 8 - 1 | Dojransko Ezero | 15:00:0015:00 | N/A |
| 2022-09-18 15:00:00September 18, 2022 | Malesh | 1 - 1 | Osogovo | 15:00:0015:00 | N/A |
| 2022-09-11 16:00:50September 11, 2022 | Osogovo | 6 - 0 | Pobeda (V) | 16:00:5016:00 | N/A |
| 2022-05-14 17:00:00May 14, 2022 | Bratstvo 07 | 2 - 4 | Osogovo | 17:00:0017:00 | N/A |
| 2022-05-07 17:00:00May 7, 2022 | Osogovo | 1 - 1 | Detonit | 17:00:0017:00 | N/A |
| 2022-04-30 17:00:00April 30, 2022 | Kozhuf | 1 - 0 | Osogovo | 17:00:0017:00 | N/A |
| 2022-04-23 16:00:00April 23, 2022 | Osogovo | 0 - 1 | Sloga 1934 | 16:00:0016:00 | N/A |
| 2022-04-16 16:00:00April 16, 2022 | Pobeda (2010) | 2 - 1 | Osogovo | 16:00:0016:00 | N/A |
| 2022-04-09 16:00:00April 9, 2022 | Osogovo | 0 - 5 | Belasica | 16:00:0016:00 | N/A |
| 2022-04-02 15:00:00April 2, 2022 | Sasa | 2 - 0 | Osogovo | 15:00:0015:00 | N/A |
| 2022-03-20 15:00:26March 20, 2022 | Osogovo | 1 - 1 | Napredok (P) | 15:00:2615:00 | N/A |
| 2022-03-12 15:00:59March 12, 2022 | Osogovo | 6 - 0 | Lokomotiva (G) | 15:00:5915:00 | N/A |
| 2022-03-05 14:00:45March 5, 2022 | Osogovo | 1 - 1 | Kozhuf | 14:00:4514:00 | N/A |
| 2022-02-26 14:00:35February 26, 2022 | Napredok (P) | 0 - 1 | Osogovo | 14:00:3514:00 | N/A |
| 2022-02-19 14:00:47February 19, 2022 | Osogovo | 0 - 3 | Belasica | 14:00:4714:00 | N/A |
| 2021-12-14 13:00:24December 14, 2021 | Detonit | 0 - 0 | Osogovo | 13:00:2413:00 | N/A |
| 2021-12-07 13:00:55December 7, 2021 | Osogovo | 1 - 3 | Pobeda (2010) | 13:00:5513:00 | N/A |
| 2021-12-04 13:00:45December 4, 2021 | Lokomotiva (G) | 1 - 1 | Osogovo | 13:00:4513:00 | N/A |
| 2021-11-27 13:00:37November 27, 2021 | Bratstvo 07 | 2 - 4 | Osogovo | 13:00:3713:00 | N/A |
| 2021-11-20 13:00:10November 20, 2021 | Osogovo | 3 - 0 | Sloga 1934 | 13:00:1013:00 | N/A |
| 2021-11-07 13:00:36November 7, 2021 | Sasa | 2 - 0 | Osogovo | 13:00:3613:00 | N/A |
| 2021-10-30 14:00:25October 30, 2021 | Kozhuf | 1 - 1 | Osogovo | 14:00:2514:00 | N/A |
| 2021-10-23 14:00:52October 23, 2021 | Osogovo | 0 - 3 | Napredok (P) | 14:00:5214:00 | N/A |
| 2021-10-16 14:00:10October 16, 2021 | Belasica | 0 - 2 | Osogovo | 14:00:1014:00 | N/A |
| 2021-10-03 15:00:21October 3, 2021 | Osogovo | 2 - 1 | Detonit | 15:00:2115:00 | N/A |
| 2021-09-25 15:00:15September 25, 2021 | Pobeda (2010) | 6 - 0 | Osogovo | 15:00:1515:00 | N/A |
| 2021-09-18 15:00:36September 18, 2021 | Osogovo | 2 - 2 | Lokomotiva (G) | 15:00:3615:00 | N/A |
| 2021-09-12 16:00:20September 12, 2021 | Osogovo | 2 - 0 | Bratstvo 07 | 16:00:2016:00 | N/A |
| 2021-08-29 16:00:27August 29, 2021 | Sloga 1934 | 1 - 0 | Osogovo | 16:00:2716:00 | N/A |
| 2021-08-25 16:00:17August 25, 2021 | Osogovo | 1 - 4 | Sasa | 16:00:1716:00 | N/A |
| 2021-05-15 16:00:40May 15, 2021 | Detonit Plachkovica | 2 - 0 | Osogovo | 16:00:4016:00 | N/A |
| 2021-05-08 16:00:19May 8, 2021 | Osogovo | 0 - 1 | Pobeda (2010) | 16:00:1916:00 | N/A |
| 2021-05-01 13:00:57May 1, 2021 | Sloga 1934 | 4 - 1 | Osogovo | 13:00:5713:00 | N/A |
| 2021-04-24 13:00:26April 24, 2021 | Osogovo | 0 - 2 | Bregalnica | 13:00:2613:00 | N/A |
| 2021-04-17 13:00:09April 17, 2021 | Tikvesh | 3 - 0 | Osogovo | 13:00:0913:00 | N/A |
| 2021-04-10 13:00:25April 10, 2021 | Osogovo | 0 - 1 | Napredok (P) | 13:00:2513:00 | N/A |
| 2021-04-03 15:00:27April 3, 2021 | Kozhuf | 0 - 1 | Osogovo | 15:00:2715:00 | N/A |
| 2021-03-21 15:00:17March 21, 2021 | Osogovo | 0 - 2 | Sasa | 15:00:1715:00 | N/A |
| 2021-03-13 15:00:04March 13, 2021 | Osogovo | 4 - 1 | Rosoman 83 | 15:00:0415:00 | N/A |
| 2021-03-06 14:00:48March 6, 2021 | Detonit Plachkovica | 0 - 1 | Osogovo | 14:00:4814:00 | N/A |
| 2021-02-27 14:00:48February 27, 2021 | Osogovo | 1 - 1 | Sasa | 14:00:4814:00 | N/A |
| 2020-12-12 13:00:31December 12, 2020 | Rosoman 83 | 1 - 7 | Osogovo | 13:00:3113:00 | N/A |
| 2020-12-05 13:00:26December 5, 2020 | Osogovo | 2 - 0 | Pobeda (2010) | 13:00:2613:00 | N/A |
| 2020-11-28 13:00:35November 28, 2020 | Sloga 1934 | 3 - 0 | Osogovo | 13:00:3513:00 | N/A |
| 2020-11-25 13:00:10November 25, 2020 | Osogovo | 1 - 3 | Bregalnica | 13:00:1013:00 | N/A |
| 2020-11-21 13:00:27November 21, 2020 | Tikvesh | 3 - 1 | Osogovo | 13:00:2713:00 | N/A |
| 2020-11-14 13:00:23November 14, 2020 | Osogovo | 1 - 0 | Napredok (P) | 13:00:2313:00 | N/A |
| 2020-11-08 13:30:52November 8, 2020 | Osogovo | 0 - 0 | Kozhuf | 13:30:5213:30 | N/A |
| 2020-10-24 14:30:00October 24, 2020 | Osogovo | 1 - 1 | Detonit Plachkovica | 14:30:0014:30 | N/A |
| 2020-10-17 14:30:14October 17, 2020 | Sasa | 0 - 0 | Osogovo | 14:30:1414:30 | N/A |
| 2020-10-10 15:00:54October 10, 2020 | Osogovo | 5 - 4 | Rosoman 83 | 15:00:5415:00 | N/A |
| 2020-10-04 15:00:01October 4, 2020 | Pobeda (2010) | 1 - 1 | Osogovo | 15:00:0115:00 | N/A |
| 2020-09-26 15:30:34September 26, 2020 | Osogovo | 1 - 1 | Sloga 1934 | 15:30:3415:30 | N/A |
| 2020-09-19 19:00:22September 19, 2020 | Bregalnica | 1 - 1 | Osogovo | 19:00:2219:00 | N/A |
| 2020-09-12 16:00:32September 12, 2020 | Osogovo | 0 - 3 | Tikvesh | 16:00:3216:00 | N/A |
| 2020-08-30 16:30:04August 30, 2020 | Napredok (P) | 3 - 3 | Osogovo | 16:30:0416:30 | N/A |
| 2020-08-22 17:00:41August 22, 2020 | Kozhuf | 2 - 0 | Osogovo | 17:00:4117:00 | N/A |
| 2020-03-22 14:30:45March 22, 2020 | Sasa | - | Osogovo | 14:30:45Canceled | N/A |
| 2020-03-14 14:30:02March 14, 2020 | Osogovo | - | Detonit Plachkovica | 14:30:02Canceled | N/A |
| 2020-03-07 14:00:23March 7, 2020 | Kozhuf | 1 - 0 | Osogovo | 14:00:2314:00 | N/A |
| 2020-02-29 14:00:08February 29, 2020 | Osogovo | 0 - 2 | Belasica | 14:00:0814:00 | N/A |
| 2019-11-30 13:00:29November 30, 2019 | Pobeda (2010) | 5 - 1 | Osogovo | 13:00:2913:00 | N/A |
| 2019-11-23 13:00:48November 23, 2019 | Osogovo | 1 - 2 | Napredok (P) | 13:00:4813:00 | N/A |
| 2019-11-09 13:00:42November 9, 2019 | Tikvesh | 7 - 1 | Osogovo | 13:00:4213:00 | N/A |
| 2019-11-02 13:30:32November 2, 2019 | Osogovo | 1 - 2 | Bregalnica | 13:30:3213:30 | N/A |
| 2019-10-26 14:30:01October 26, 2019 | Pitu Guli | 1 - 3 | Osogovo | 14:30:0114:30 | N/A |
| 2019-10-20 14:30:11October 20, 2019 | Osogovo | 2 - 5 | Sasa | 14:30:1114:30 | N/A |
| 2019-10-11 15:00:14October 11, 2019 | Detonit Plachkovica | 2 - 1 | Osogovo | 15:00:1415:00 | N/A |
| 2019-10-06 15:00:23October 6, 2019 | Osogovo | 0 - 4 | Kozhuf | 15:00:2315:00 | N/A |
| 2019-09-28 15:00:59September 28, 2019 | Belasica | 3 - 0 | Osogovo | 15:00:5915:00 | N/A |
| 2019-09-21 15:30:17September 21, 2019 | Osogovo | 1 - 0 | Pobeda (2010) | 15:30:1715:30 | N/A |
| 2019-09-15 15:30:21September 15, 2019 | Napredok (P) | 1 - 0 | Osogovo | 15:30:2115:30 | N/A |
| 2019-09-07 16:00:48September 7, 2019 | Osogovo | 0 - 1 | Tikvesh | 16:00:4816:00 | N/A |
| 2019-08-31 19:00:41August 31, 2019 | Bregalnica | 5 - 0 | Osogovo | 19:00:4119:00 | N/A |
| 2019-08-24 17:00:16August 24, 2019 | Osogovo | 1 - 3 | Pitu Guli | 17:00:1617:00 | N/A |
| 2019-05-29 16:30:51May 29, 2019 | Osogovo | 0 - 0 | Sloga 1934 | 16:30:5116:30 | N/A |
| 2019-05-26 16:30:29May 26, 2019 | Bregalnica 1926 | 2 - 2 | Osogovo | 16:30:2916:30 | N/A |
| 2019-05-19 16:00:39May 19, 2019 | Malesh | 1 - 3 | Osogovo | 16:00:3916:00 | N/A |
| 2019-05-15 16:00:58May 15, 2019 | Ovche Pole | 1 - 1 | Osogovo | 16:00:5816:00 | N/A |
| 2019-05-11 16:00:08May 11, 2019 | Osogovo | 2 - 3 | Rudar | 16:00:0816:00 | N/A |
| 2019-05-04 16:00:38May 4, 2019 | Sloga 1934 | 0 - 2 | Osogovo | 16:00:3816:00 | N/A |
| 2019-04-27 16:00:50April 27, 2019 | Osogovo | 2 - 1 | Bregalnica 1926 | 16:00:5016:00 | N/A |
| 2019-04-20 15:30:44April 20, 2019 | Rabotnik (L) | 0 - 1 | Osogovo | 15:30:4415:30 | N/A |
| 2019-04-14 15:30:52April 14, 2019 | Osogovo | 8 - 1 | Malesh | 15:30:5215:30 | N/A |
| 2019-04-10 15:30:15April 10, 2019 | Osogovo | 1 - 1 | Ovche Pole | 15:30:1515:30 | N/A |
| 2019-04-07 15:30:34April 7, 2019 | Rudar | 1 - 3 | Osogovo | 15:30:3415:30 | N/A |
| 2018-12-02 13:00:18December 2, 2018 | Osogovo | 3 - 0 | Sloga 1934 | 13:00:1813:00 | N/A |
| 2018-11-25 13:00:41November 25, 2018 | Bregalnica 1926 | 2 - 4 | Osogovo | 13:00:4113:00 | N/A |
| 2018-11-18 13:00:33November 18, 2018 | Osogovo | 3 - 1 | Rabotnik (L) | 13:00:3313:00 | N/A |
| 2018-11-11 13:00:56November 11, 2018 | Malesh | 1 - 2 | Osogovo | 13:00:5613:00 | N/A |
| 2018-11-04 13:30:48November 4, 2018 | Ovche Pole | 3 - 0 | Osogovo | 13:30:4813:30 | N/A |
| 2018-10-28 13:30:10October 28, 2018 | Osogovo | 7 - 0 | Rudar | 13:30:1013:30 | N/A |
| 2018-10-23 14:00:27October 23, 2018 | Kezhovica | 1 - 0 | Osogovo | 14:00:2714:00 | N/A |
| 2018-10-20 14:30:50October 20, 2018 | Sloga 1934 | 1 - 2 | Osogovo | 14:30:5014:30 | N/A |
| 2018-10-14 14:30:01October 14, 2018 | Osogovo | 2 - 0 | Bregalnica 1926 | 14:30:0114:30 | N/A |
| 2018-10-11 15:00:39October 11, 2018 | Rabotnik (L) | 3 - 2 | Osogovo | 15:00:3915:00 | N/A |
| 2018-10-07 15:00:58October 7, 2018 | Osogovo | 2 - 1 | Malesh | 15:00:5815:00 | N/A |
| 2018-09-29 15:30:35September 29, 2018 | Osogovo | 2 - 0 | Ovche Pole | 15:30:3515:30 | N/A |
| 2018-09-23 15:30:50September 23, 2018 | Rudar | 1 - 3 | Osogovo | 15:30:5015:30 | N/A |
| 2018-09-16 16:00:11September 16, 2018 | Osogovo | 1 - 0 | Kezhovica | 16:00:1116:00 | N/A |
| 2018-05-19 16:30:37May 19, 2018 | Osogovo | 1 - 2 | Kozhuf | 16:30:3716:30 | N/A |
| 2018-05-12 16:30:29May 12, 2018 | Tikvesh | 2 - 1 | Osogovo | 16:30:2916:30 | N/A |
| 2018-04-28 16:00:18April 28, 2018 | Pobeda (V) | 3 - 5 | Osogovo | 16:00:1816:00 | N/A |
| 2018-04-24 16:00:52April 24, 2018 | Detonit Plachkovica | 3 - 2 | Osogovo | 16:00:5216:00 | N/A |
| 2018-04-21 16:00:07April 21, 2018 | Osogovo | 1 - 0 | Sasa | 16:00:0716:00 | N/A |
| 2018-04-17 16:00:27April 17, 2018 | Belasica | 5 - 0 | Osogovo | 16:00:2716:00 | N/A |
| 2018-04-14 16:00:16April 14, 2018 | Osogovo | 0 - 0 | Bregalnica | 16:00:1616:00 | N/A |
| 2018-04-07 16:00:40April 7, 2018 | Borec | 1 - 0 | Osogovo | 16:00:4016:00 | N/A |
| 2018-03-31 15:00:50March 31, 2018 | Osogovo | 2 - 2 | Bregalnica | 15:00:5015:00 | N/A |
| 2018-03-18 14:00:34March 18, 2018 | Borec | 2 - 1 | Osogovo | 14:00:3414:00 | N/A |
| 2018-03-10 14:00:53March 10, 2018 | Osogovo | 4 - 0 | Pobeda (V) | 14:00:5314:00 | N/A |
| 2017-11-25 13:00:00November 25, 2017 | Sasa | 2 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2017-11-18 13:00:00November 18, 2017 | Osogovo | 0 - 0 | Belasica | 13:00:0013:00 | N/A |
| 2017-11-11 13:00:00November 11, 2017 | Detonit Plachkovica | 2 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 2017-11-04 13:30:00November 4, 2017 | Osogovo | 0 - 4 | Tikvesh | 13:30:0013:30 | N/A |
| 2017-10-28 13:30:00October 28, 2017 | Kozhuf | 2 - 1 | Osogovo | 13:30:0013:30 | N/A |
| 2017-10-21 14:30:00October 21, 2017 | Bregalnica | 5 - 0 | Osogovo | 14:30:0014:30 | N/A |
| 2017-10-14 14:30:00October 14, 2017 | Osogovo | 1 - 2 | Borec | 14:30:0014:30 | N/A |
| 2017-10-07 14:30:00October 7, 2017 | Pobeda (V) | 3 - 0 | Osogovo | 14:30:0014:30 | N/A |
| 2017-10-01 15:00:00October 1, 2017 | Osogovo | 1 - 3 | Horizont | 15:00:0015:00 | N/A |
| 2017-09-26 15:30:00September 26, 2017 | Osogovo | 2 - 2 | Sasa | 15:30:0015:30 | N/A |
| 2017-09-23 19:30:00September 23, 2017 | Belasica | 5 - 0 | Osogovo | 19:30:0019:30 | N/A |
| 2017-09-16 15:30:00September 16, 2017 | Osogovo | 2 - 1 | Detonit Plachkovica | 15:30:0015:30 | N/A |
| 2017-09-09 16:00:00September 9, 2017 | Tikvesh | 2 - 1 | Osogovo | 16:00:0016:00 | N/A |
| 2017-08-27 16:30:00August 27, 2017 | Osogovo | 1 - 0 | Kozhuf | 16:30:0016:30 | N/A |
| 2017-05-24 16:30:00May 24, 2017 | Osogovo | - | Belasica | 16:30:0016:30 | N/A |
| 2017-05-21 16:30:00May 21, 2017 | Detonit Plachkovica | - | Osogovo | 16:30:0016:30 | N/A |
| 2017-05-14 16:30:00May 14, 2017 | Osogovo | - | Sasa | 16:30:0016:30 | N/A |
| 2017-05-07 16:30:00May 7, 2017 | Sloga 1934 | - | Osogovo | 16:30:0016:30 | N/A |
| 2017-04-15 16:00:00April 15, 2017 | Osogovo | 4 - 1 | Napredok (R) | 16:00:0016:00 | N/A |
| 2017-04-09 16:00:00April 9, 2017 | Malesh | 2 - 4 | Osogovo | 16:00:0016:00 | N/A |
| 2017-04-02 15:00:00April 2, 2017 | Osogovo | 4 - 1 | Napredok (P) | 15:00:0015:00 | N/A |
| 2017-03-29 15:00:00March 29, 2017 | Vasilevo | 1 - 3 | Osogovo | 15:00:0015:00 | N/A |
| 2017-03-26 15:00:00March 26, 2017 | Osogovo | 1 - 0 | Rudar | 15:00:0015:00 | N/A |
| 2017-03-19 14:00:00March 19, 2017 | Bregalnica 1926 | 1 - 2 | Osogovo | 14:00:0014:00 | N/A |
| 2017-03-12 14:00:00March 12, 2017 | Ovche Pole | 0 - 2 | Osogovo | 14:00:0014:00 | N/A |
| 2017-03-05 14:00:00March 5, 2017 | Osogovo | 5 - 0 | Tiverija | 14:00:0014:00 | N/A |
| 2017-02-26 14:00:00February 26, 2017 | Rabotnik (L) | 0 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2016-11-27 18:00:00November 27, 2016 | Belasica | 2 - 0 | Osogovo | 18:00:0018:00 | N/A |
| 2016-11-20 13:00:00November 20, 2016 | Osogovo | 0 - 2 | Detonit Plachkovica | 13:00:0013:00 | N/A |
| 2016-11-13 13:00:00November 13, 2016 | Sasa | 2 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2016-11-06 13:30:00November 6, 2016 | Osogovo | 2 - 0 | Sloga 1934 | 13:30:0013:30 | N/A |
| 2016-11-02 13:30:00November 2, 2016 | Osogovo | 3 - 0 | Birlik (К) | 13:30:0013:30 | N/A |
| 2016-10-23 14:00:00October 23, 2016 | Napredok (R) | 0 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2016-10-16 14:30:00October 16, 2016 | Osogovo | 2 - 0 | Malesh | 14:30:0014:30 | N/A |
| 2016-10-11 14:30:00October 11, 2016 | Napredok (P) | 0 - 2 | Osogovo | 14:30:0014:30 | N/A |
| 2016-10-08 14:30:00October 8, 2016 | Osogovo | 4 - 1 | Vasilevo | 14:30:0014:30 | N/A |
| 2016-10-02 15:00:00October 2, 2016 | Rudar | 0 - 4 | Osogovo | 15:00:0015:00 | N/A |
| 2016-09-24 15:30:00September 24, 2016 | Osogovo | 3 - 0 | Bregalnica 1926 | 15:30:0015:30 | N/A |
| 2016-09-18 15:30:00September 18, 2016 | Osogovo | 1 - 2 | Ovche Pole | 15:30:0015:30 | N/A |
| 2016-09-11 14:00:00September 11, 2016 | Tiverija | 3 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2016-09-08 16:00:00September 8, 2016 | Osogovo | 3 - 0 | Rabotnik (L) | 16:00:0016:00 | N/A |
| 2012-05-22 17:00:42May 22, 2012 | Osogovo | 1 - 5 | Rufeja 93 | 17:00:4217:00 | N/A |
| 2012-05-19 17:00:12May 19, 2012 | Korabi | 5 - 2 | Osogovo | 17:00:1217:00 | N/A |
| 2012-05-15 17:00:13May 15, 2012 | Osogovo | 0 - 0 | Drita 94 | 17:00:1317:00 | N/A |
| 2012-05-12 16:30:53May 12, 2012 | Gostivar | 3 - 1 | Osogovo | 16:30:5316:30 | N/A |
| 2012-05-05 16:30:34May 5, 2012 | Osogovo | 0 - 2 | Kozhuf (M) | 16:30:3416:30 | N/A |
| 2012-04-29 16:30:14April 29, 2012 | Euromilk  | 5 - 1 | Osogovo | 16:30:1416:30 | N/A |
| 2012-04-21 16:00:54April 21, 2012 | Osogovo | 1 - 0 | Ohrid Lote | 16:00:5416:00 | N/A |
| 2012-04-14 16:00:31April 14, 2012 | Makedonija GjP | 2 - 0 | Osogovo | 16:00:3116:00 | N/A |
| 2012-04-10 16:00:08April 10, 2012 | Osogovo | 0 - 0 | Akademija Ilinden | 16:00:0816:00 | N/A |
| 2012-04-07 16:00:33April 7, 2012 | Vlazrimi 77 | 1 - 0 | Osogovo | 16:00:3316:00 | N/A |
| 2012-03-31 16:00:00March 31, 2012 | Osogovo | 1 - 2 | Pelister | 16:00:0016:00 | N/A |
| 2012-03-27 15:00:00March 27, 2012 | Skopje | 2 - 0 | Osogovo | 15:00:0015:00 | N/A |
| 2012-03-24 14:00:00March 24, 2012 | Pobeda (2010) | 2 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2012-03-13 14:00:00March 13, 2012 | Osogovo | 1 - 0 | Tikvesh | 14:00:0014:00 | N/A |
| 2012-03-10 14:00:00March 10, 2012 | Belasica | 3 - 1 | Osogovo | 14:00:0014:00 | N/A |
| 2011-12-04 13:00:00December 4, 2011 | Rufeja 93 | 3 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2011-11-27 13:00:00November 27, 2011 | Osogovo | 2 - 0 | Korabi | 13:00:0013:00 | N/A |
| 2011-11-20 13:00:00November 20, 2011 | Drita 94 | 4 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2011-11-05 13:00:00November 5, 2011 | Osogovo | 3 - 2 | Gostivar | 13:00:0013:00 | N/A |
| 2011-10-30 13:00:00October 30, 2011 | Kozhuf (M) | 4 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 2011-10-23 14:00:00October 23, 2011 | Osogovo | 2 - 3 | Euromilk | 14:00:0014:00 | N/A |
| 2011-10-16 14:00:00October 16, 2011 | Ohrid Lote | 4 - 2 | Osogovo | 14:00:0014:00 | N/A |
| 2011-10-02 15:00:00October 2, 2011 | Osogovo | 0 - 3 | Makedonija GjP | 15:00:0015:00 | N/A |
| 2011-09-25 15:00:00September 25, 2011 | Akademija Ilinden | 3 - 0 | Osogovo | 15:00:0015:00 | N/A |
| 2011-09-18 15:30:00September 18, 2011 | Osogovo | 0 - 0 | Vlazrimi 77 | 15:30:0015:30 | N/A |
| 2011-09-11 16:00:00September 11, 2011 | Pelister | 1 - 1 | Osogovo | 16:00:0016:00 | N/A |
| 2011-08-28 16:30:00August 28, 2011 | Osogovo | 1 - 0 | Skopje | 16:30:0016:30 | N/A |
| 2011-08-21 16:30:00August 21, 2011 | Osogovo | 1 - 2 | Pobeda (2010) | 16:30:0016:30 | N/A |
| 2011-08-14 17:00:00August 14, 2011 | Tikvesh | 3 - 1 | Osogovo | 17:00:0017:00 | N/A |
| 2011-08-07 17:00:00August 7, 2011 | Osogovo | 3 - 0 | Belasica | 17:00:0017:00 | N/A |
| 1993-06-13 17:00:00June 13, 1993 | Osogovo | 3 - 0 (awarded) | Bregalnica | 17:00:0017:00 | N/A |
| 1993-06-09 17:00:00June 9, 1993 | Balkan | 1 - 1 | Osogovo | 17:00:0017:00 | N/A |
| 1993-06-06 17:00:00June 6, 1993 | Shkupi | 0 - 1 | Osogovo | 17:00:0017:00 | N/A |
| 1993-05-30 13:00:00May 30, 1993 | Osogovo | 3 - 1 | Sasa | 13:00:0013:00 | N/A |
| 1993-05-22 13:00:00May 22, 1993 | Metalurg | 0 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 1993-05-16 13:00:00May 16, 1993 | Osogovo | 3 - 1 | Pobeda | 13:00:0013:00 | N/A |
| 1993-05-09 13:00:00May 9, 1993 | Pelister | 1 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1993-05-05 13:00:00May 5, 1993 | Osogovo | 0 - 1 | Makedonija GjP | 13:00:0013:00 | N/A |
| 1993-05-01 13:00:00May 1, 1993 | Borec | 0 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1993-04-25 13:00:00April 25, 1993 | Osogovo | 5 - 0 | Vardarski | 13:00:0013:00 | N/A |
| 1993-04-19 13:00:00April 19, 1993 | Tikvesh | 1 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 1993-04-11 13:00:00April 11, 1993 | Osogovo | 1 - 0 | Belasica | 13:00:0013:00 | N/A |
| 1993-04-07 13:00:00April 7, 1993 | Rudar | 1 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1993-04-04 13:00:00April 4, 1993 | Osogovo | 0 - 2 | Vardar | 13:00:0013:00 | N/A |
| 1993-03-28 13:00:00March 28, 1993 | Sileks | 1 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1993-03-21 13:00:00March 21, 1993 | Osogovo | 1 - 0 | Cementarnica 55 | 13:00:0013:00 | N/A |
| 1993-03-14 13:00:00March 14, 1993 | Teteks | 1 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1992-11-29 13:00:00November 29, 1992 | Bregalnica | 2 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1992-11-22 13:00:00November 22, 1992 | Osogovo | 0 - 0 | Balkan | 13:00:0013:00 | N/A |
| 1992-11-15 13:00:00November 15, 1992 | Osogovo | 1 - 0 | Shkupi | 13:00:0013:00 | N/A |
| 1992-11-08 13:00:00November 8, 1992 | Sasa | 3 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1992-11-01 13:00:00November 1, 1992 | Osogovo | 2 - 3 | Metalurg | 13:00:0013:00 | N/A |
| 1992-10-25 13:00:00October 25, 1992 | Pobeda | 6 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 1992-10-21 14:30:00October 21, 1992 | Osogovo | 1 - 0 | Pelister | 14:30:0014:30 | N/A |
| 1992-10-18 13:00:00October 18, 1992 | Makedonija GjP | 0 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1992-10-11 13:00:00October 11, 1992 | Osogovo | 4 - 0 | Borec | 13:00:0013:00 | N/A |
| 1992-10-04 13:00:00October 4, 1992 | Vardarski | 0 - 0 | Osogovo | 13:00:0013:00 | N/A |
| 1992-09-27 13:00:00September 27, 1992 | Osogovo | 1 - 0 | Tikvesh | 13:00:0013:00 | N/A |
| 1992-09-23 13:00:00September 23, 1992 | Belasica | 2 - 1 | Osogovo | 13:00:0013:00 | N/A |
| 1992-09-20 13:00:00September 20, 1992 | Osogovo | 2 - 2 | Rudar | 13:00:0013:00 | N/A |
| 1992-09-13 19:00:00September 13, 1992 | Vardar | 8 - 0 | Osogovo | 19:00:0019:00 | N/A |
| 1992-09-06 13:00:00September 6, 1992 | Osogovo | 0 - 0 | Sileks | 13:00:0013:00 | N/A |
| 1992-08-30 13:00:00August 30, 1992 | Cementarnica 55 | 4 - 3 | Osogovo | 13:00:0013:00 | N/A |
| 1992-08-23 13:00:00August 23, 1992 | Osogovo | 3 - 0 | Teteks | 13:00:0013:00 | N/A |
