| 2026-05-17 10:00:00May 17, 2026 | Old Boys  | - | Chagor | 10:00:0010:00 | N/A |
| 2026-05-10 10:00:00May 10, 2026 | Mladost (B)  | - | Old Boys | 10:00:0010:00 | N/A |
| 2026-05-03 10:00:00May 3, 2026 | Old Boys  | - | Novaci 2011 | 10:00:0010:00 | N/A |
| 2026-04-26 10:00:00April 26, 2026 | Mladost (GO)  | - | Old Boys | 10:00:0010:00 | N/A |
| 2026-04-19 10:00:00April 19, 2026 | Old Boys  | - | Dalbegovci | 10:00:0010:00 | N/A |
| 2026-04-13 16:00:00April 13, 2026 | Lisolaj  | 8 - 3 | Old Boys | 16:00:0016:00 | N/A |
| 2026-04-05 10:00:00April 5, 2026 | DOSK  | 6 - 0 | Old Boys | 10:00:0010:00 | N/A |
| 2026-03-29 15:30:11March 29, 2026 | Dalbegovci  | 0 - 1 | Old Boys | 15:30:1115:30 | N/A |
| 2026-03-22 12:00:19March 22, 2026 | Old Boys  | 0 - 2 | Lisolaj | 12:00:1912:00 | N/A |
| 2026-03-15 14:30:27March 15, 2026 | Mladost (GO)  | 6 - 3 | Old Boys | 14:30:2714:30 | N/A |
| 2025-11-30 10:00:00November 30, 2025 | Old Boys  | 5 - 1 | Novaci 2011 | 10:00:0010:00 | N/A |
| 2025-11-23 13:30:00November 23, 2025 | Old Boys  | 6 - 0 | Mladost (B) | 13:30:0013:30 | N/A |
| 2025-11-16 10:00:00November 16, 2025 | Chagor  | 1 - 3 | Old Boys | 10:00:0010:00 | N/A |
| 2025-11-09 14:00:00November 9, 2025 | Old Boys  | 0 - 5 | DOSK | 14:00:0014:00 | N/A |
| 2025-11-02 14:00:00November 2, 2025 | Old Boys  | 3 - 2 | Dalbegovci | 14:00:0014:00 | N/A |
| 2025-10-26 10:00:00October 26, 2025 | Lisolaj  | 3 - 1 | Old Boys | 10:00:0010:00 | N/A |
| 2025-10-12 15:00:00October 12, 2025 | Old Boys  | 0 - 4 | Mladost (GO) | 15:00:0015:00 | N/A |
| 2025-10-05 10:00:00October 5, 2025 | Novaci 2011  | 4 - 2 | Old Boys | 10:00:0010:00 | N/A |
| 2025-09-28 10:00:00September 28, 2025 | Mladost (B)  | 0 - 3 | Old Boys | 10:00:0010:00 | N/A |
| 2025-09-21 15:30:00September 21, 2025 | Old Boys  | 3 - 3 | Chagor | 15:30:0015:30 | N/A |
| 2025-09-14 16:00:17September 14, 2025 | DOSK  | 3 - 0 | Old Boys | 16:00:1716:00 | N/A |
| 2025-05-21 17:00:29May 21, 2025 | Chagor  | 2 - 2 | Old Boys | 17:00:2917:00 | N/A |
| 2025-05-14 17:00:21May 14, 2025 | Old Boys  | 4 - 2 | Mladost (GO) | 17:00:2117:00 | N/A |
| 2025-05-11 10:00:55May 11, 2025 | Lisolaj  | 4 - 1 | Old Boys | 10:00:5510:00 | N/A |
| 2025-05-04 17:00:00May 4, 2025 | Old Boys  | 1 - 6 | Mogila | 17:00:0017:00 | N/A |
| 2025-04-27 10:00:40April 27, 2025 | DOSK  | 1 - 1 | Old Boys | 10:00:4010:00 | N/A |
| 2025-04-21 16:00:58April 21, 2025 | Old Boys  | 0 - 4 | Novaci 2011 | 16:00:5816:00 | N/A |
| 2025-04-18 10:00:10April 18, 2025 | Old Boys  | 4 - 3 | Pelagonija (T) | 10:00:1010:00 | N/A |
| 2025-04-13 10:00:33April 13, 2025 | Old Boys  | 1 - 1 | Chagor | 10:00:3310:00 | N/A |
| 2025-04-06 10:00:15April 6, 2025 | Lisolaj  | 5 - 1 | Old Boys | 10:00:1510:00 | N/A |
| 2025-03-30 15:00:53March 30, 2025 | Old Boys  | 5 - 4 | Pelagonija (T) | 15:00:5315:00 | N/A |
| 2025-03-09 14:00:01March 9, 2025 | Mogila  | 6 - 0 | Old Boys | 14:00:0114:00 | N/A |
| 2024-11-17 10:00:00November 17, 2024 | Old Boys  | 2 - 3 | DOSK | 10:00:0010:00 | N/A |
| 2024-11-10 13:00:00November 10, 2024 | Mladost (GO)  | 5 - 2 | Old Boys | 13:00:0013:00 | N/A |
| 2024-11-03 10:00:00November 3, 2024 | Old Boys  | 6 - 3 | Novaci 2011 | 10:00:0010:00 | N/A |
| 2024-10-27 10:00:00October 27, 2024 | Chagor  | 0 - 4 | Old Boys | 10:00:0010:00 | N/A |
| 2024-10-23 10:00:00October 23, 2024 | Novaci 2011  | 0 - 7 | Old Boys | 10:00:0010:00 | N/A |
| 2024-10-20 10:00:00October 20, 2024 | Old Boys  | 1 - 1 | Lisolaj | 10:00:0010:00 | N/A |
| 2024-10-13 10:00:00October 13, 2024 | Pelagonija (T)  | 0 - 4 | Old Boys | 10:00:0010:00 | N/A |
| 2024-10-06 15:00:00October 6, 2024 | Old Boys  | 1 - 2 | Mogila | 15:00:0015:00 | N/A |
| 2024-09-29 10:00:00September 29, 2024 | DOSK  | 4 - 1 | Old Boys | 10:00:0010:00 | N/A |
| 2024-09-22 15:30:00September 22, 2024 | Old Boys  | 2 - 2 | Mladost (GO) | 15:30:0015:30 | N/A |
| 2020-03-01 10:00:39March 1, 2020 | DOSK  | 2 - 3 | Old Boys | 10:00:3910:00 | N/A |
| 2019-11-24 10:00:46November 24, 2019 | Jeni Maale  | 0 - 2 | Old Boys | 10:00:4610:00 | N/A |
| 2019-11-17 10:00:34November 17, 2019 | Old Boys  | 2 - 1 | Napredok (N) | 10:00:3410:00 | N/A |
| 2019-11-10 10:00:48November 10, 2019 | Pelagonija (D)  | 1 - 0 | Old Boys | 10:00:4810:00 | N/A |
| 2019-11-03 10:00:34November 3, 2019 | Old Boys  | 2 - 4 | Poeshevo | 10:00:3410:00 | N/A |
| 2019-10-27 10:00:22October 27, 2019 | Crna Reka  | 1 - 2 | Old Boys | 10:00:2210:00 | N/A |
| 2019-10-23 14:30:55October 23, 2019 | Old Boys  | 1 - 2 | Pobeda (I) | 14:30:5514:30 | N/A |
| 2019-10-20 10:00:43October 20, 2019 | Kosmos  | 1 - 3 | Old Boys | 10:00:4310:00 | N/A |
| 2019-10-13 15:00:13October 13, 2019 | Old Boys  | 3 - 0 | Pelagonija (L) | 15:00:1315:00 | N/A |
| 2019-10-06 15:00:11October 6, 2019 | Karamani  | 4 - 4 | Old Boys | 15:00:1115:00 | N/A |
| 2019-09-29 15:30:00September 29, 2019 | Old Boys  | 1 - 0 | Lisolaj | 15:30:0015:30 | N/A |
| 2019-09-22 10:00:14September 22, 2019 | Svetlost (K)  | 2 - 5 | Old Boys | 10:00:1410:00 | N/A |
| 2019-09-15 16:00:17September 15, 2019 | Old Boys  | 7 - 3 | Chagor | 16:00:1716:00 | N/A |
| 2019-09-08 10:00:09September 8, 2019 | Novaci 2011  | 2 - 4 | Old Boys | 10:00:0910:00 | N/A |
| 2019-09-01 17:00:07September 1, 2019 | Old Boys  | 4 - 2 | DOSK | 17:00:0717:00 | N/A |
| 2019-08-25 10:00:28August 25, 2019 | Old Boys  | 3 - 0 | Bukovo | 10:00:2810:00 | N/A |