| 2026-11-22 10:00:00November 22, 2026 | Metalurg 2025  | - |  Olimpik (S) | 10:00:0010:00 | N/A |
| 2026-11-15 10:00:00November 15, 2026 | Olimpik (S) | - |  Vidri | 10:00:0010:00 | N/A |
| 2026-11-01 12:00:00November 1, 2026 | Shishevo  | 0 - 3 (awarded) | Olimpik (S) | 12:00:0012:00 | N/A |
| 2026-10-25 12:30:00October 25, 2026 | Olimpik (S) | 1 - 3 |  Tekstilec | 12:30:0012:30 | N/A |
| 2026-10-18 10:00:00October 18, 2026 | Rashtak  | 4 - 2 | Olimpik (S) | 10:00:0010:00 | N/A |
| 2026-10-11 10:00:00October 11, 2026 | Olimpik (S) | 4 - 1 |  Slavija | 10:00:0010:00 | N/A |
| 2026-10-04 10:00:00October 4, 2026 | Bratstvo (Lj) | 5 - 1 | Olimpik (S) | 10:00:0010:00 | N/A |
| 2026-09-27 10:00:02September 27, 2026 | Olimpik (S) | 7 - 1 |  SSK Nova | 10:00:0210:00 | N/A |
| 2026-09-20 17:00:48September 20, 2026 | Shishevo | 4 - 4 | Olimpik (S) | 17:00:4817:00 | N/A |
| 2026-09-13 17:00:57September 13, 2026 | Vardar 75  | 4 - 1 | Olimpik (S) | 17:00:5717:00 | N/A |
| 2026-09-06 17:30:33September 6, 2026 | Shishevo | 2 - 5 | Olimpik (S) | 17:30:3317:30 | N/A |
| 2026-08-30 18:00:15August 30, 2026 | Bratstvo (Lj) | - | Olimpik (S) | 18:00:1518:00 | N/A |
| 2026-08-16 18:00:45August 16, 2026 | Olimpik (S) | 4 - 5 | Üsküp 1911 | 18:00:4518:00 | N/A |
| 2026-06-14 18:00:11June 14, 2026 | Olimpik (S) | 4 - 7 |  Vranovci | 18:00:1118:00 | N/A |
| 2026-03-22 12:00:18March 22, 2026 | Shishevo | 5 - 1 | Olimpik (S) | 12:00:1812:00 | N/A |
| 2026-03-21 13:00:04March 21, 2026 | Olimpik (S) | 1 - 3 | Bratstvo (Lj) | 13:00:0413:00 | N/A |
| 2026-03-08 19:00:06March 8, 2026 | Tearca-97  | 3 - 3 | Olimpik (S) | 19:00:0619:00 | N/A |
| 2026-03-01 14:00:10March 1, 2026 | Olimpik (S) | - | Slavija | 14:00:1014:00 | N/A |
| 2026-02-22 14:00:33February 22, 2026 | Shishevo | 3 - 5 | Olimpik (S) | 14:00:3314:00 | N/A |
| 2025-07-25 19:00:54July 25, 2025 | Fortuna | - | Olimpik (S) | 19:00:5419:00 | N/A |
| 2025-05-25 17:30:31May 25, 2025 | Olimpik (S) | 1 - 2 |  Napredok 65 | 17:30:3117:30 | N/A |
| 2025-05-18 18:00:07May 18, 2025 | Përparimi (N) | 2 - 2 | Olimpik (S) | 18:00:0718:00 | N/A |
| 2025-05-11 17:00:27May 11, 2025 | Olimpik (S) | 4 - 1 | Bratstvo (Lj) | 17:00:2717:00 | N/A |
| 2025-05-04 16:00:48May 4, 2025 | Shishevo | 1 - 2 | Olimpik (S) | 16:00:4816:00 | N/A |
| 2025-04-13 10:00:52April 13, 2025 | Rashtak | 3 - 0 (awarded) | Olimpik (S) | 10:00:5210:00 | N/A |
| 2025-04-06 17:30:30April 6, 2025 | Besa Saraj | 13 - 0 | Olimpik (S) | 17:30:3017:30 | N/A |
| 2025-02-23 13:00:07February 23, 2025 | Shishevo | 6 - 1 | Olimpik (S) | 13:00:0713:00 | N/A |
| 2025-02-16 13:00:08February 16, 2025 | Olimpik (S) | 5 - 6 | Üsküp 1911 | 13:00:0813:00 | N/A |
| 2025-02-09 12:00:46February 9, 2025 | Zelenikovo | 5 - 2 | Olimpik (S) | 12:00:4612:00 | N/A |
| 2025-02-02 13:00:22February 2, 2025 | Olimpik (S) | 4 - 2 | Üsküp 1911 | 13:00:2213:00 | N/A |
| 2024-11-17 12:00:00November 17, 2024 | Napredok 65 | 4 - 4 | Olimpik (S) | 12:00:0012:00 | N/A |
| 2024-11-10 12:00:00November 10, 2024 | Olimpik (S) | 3 - 4 | Përparimi (N) | 12:00:0012:00 | N/A |
| 2024-11-03 13:00:00November 3, 2024 | Bratstvo (Lj) | 3 - 1 | Olimpik (S) | 13:00:0013:00 | N/A |
| 2024-10-27 14:00:00October 27, 2024 | Olimpik (S) | 1 - 0 | Shishevo | 14:00:0014:00 | N/A |
| 2024-10-20 12:00:00October 20, 2024 | Volkovo | 1 - 5 | Olimpik (S) | 12:00:0012:00 | N/A |
| 2024-10-13 15:30:00October 13, 2024 | Olimpik (S) | 1 - 8 | Rashtak | 15:30:0015:30 | N/A |
| 2024-10-06 15:30:14October 6, 2024 | Olimpik (S) | 3 - 0 (awarded) | Besa Saraj | 15:30:1415:30 | N/A |
| 2024-09-29 16:00:07September 29, 2024 | Olimpik (S) | - | Besa Saraj | 16:00:0716:00 | N/A |
| 2024-09-15 16:30:32September 15, 2024 | Madjari Solidarnost | 6 - 1 | Olimpik (S) | 16:30:3216:30 | N/A |
| 2024-09-08 10:00:10September 8, 2024 | Zelenikovo | 1 - 3 | Olimpik (S) | 10:00:1010:00 | N/A |
| 2024-09-01 10:00:08September 1, 2024 | Slavija | 6 - 2 | Olimpik (S) | 10:00:0810:00 | N/A |
| 2024-08-18 17:30:03August 18, 2024 | Olimpik (S) | 5 - 8 | Üsküp 1911 | 17:30:0317:30 | N/A |
| 2024-03-03 13:00:12March 3, 2024 | Goce Delchev (S) | 2 - 2 | Olimpik (S) | 13:00:1213:00 | N/A |
| 2024-02-18 14:00:17February 18, 2024 | Rashtak | 4 - 1 | Olimpik (S) | 14:00:1714:00 | N/A |
| 2024-02-04 15:00:28February 4, 2024 | Olimpik (S) | 2 - 6 | Slavija | 15:00:2815:00 | N/A |
| 2023-12-24 13:30:37December 24, 2023 | Vardar 75 | 1 - 5 | Olimpik (S) | 13:30:3713:30 | N/A |
| 2023-12-17 13:00:54December 17, 2023 | Olimpik (S) | 5 - 6 | Üsküp 1911 | 13:00:5413:00 | N/A |
| 2023-07-23 18:30:36July 23, 2023 | Olimpik (S) | 2 - 4 | Sloboden | 18:30:3618:30 | N/A |
| 2023-06-25 17:30:57June 25, 2023 | Olimpik (S) | 3 - 2 | Napredok 65 | 17:30:5717:30 | N/A |
| 2023-06-11 17:30:05June 11, 2023 | Deljadrovci | 3 - 3 | Olimpik (S) | 17:30:0517:30 | N/A |
| 2023-06-04 17:00:36June 4, 2023 | Olimpik (S) | 4 - 3 | Üsküp 1911 | 17:00:3617:00 | N/A |
| 2022-10-08 15:00:24October 8, 2022 | Olimpik (S) | 2 - 2 | Üsküp 1911 | 15:00:2415:00 | N/A |
| 2022-09-18 10:30:33September 18, 2022 | Partizan (S) | 10 - 1 | Olimpik (S) | 10:30:3310:30 | N/A |
| 2022-09-11 16:30:46September 11, 2022 | Pobeda (DL) | 2 - 3 | Olimpik (S) | 16:30:4616:30 | N/A |
| 2022-09-04 11:00:47September 4, 2022 | Olimpik (S) | 4 - 5 | Slavija | 11:00:4711:00 | N/A |
| 2022-08-28 17:00:22August 28, 2022 | Olimpik (S) | 11 - 1 | Üsküp 1911 | 17:00:2217:00 | N/A |
| 2022-08-21 17:30:37August 21, 2022 | Olimpik (S) | 4 - 3 | Sloboden | 17:30:3717:30 | N/A |
