| 2025-11-23 13:00:00November 23, 2025 | Besa  | - |  Kumanovo | 13:00:0013:00 | N/A |
| 2025-11-19 13:30:00November 19, 2025 | Kumanovo | - |  Llopati 97 | 13:30:0013:30 | N/A |
| 2025-11-16 13:00:00November 16, 2025 | Kumanovo | - |  Euromilk | 13:00:0013:00 | N/A |
| 2025-11-09 13:30:00November 9, 2025 | BVK Konjare  | 3 - 2 | Kumanovo | 13:30:0013:30 | N/A |
| 2025-11-05 14:00:00November 5, 2025 | Kumanovo | 2 - 2 |  R’zhanichino | 14:00:0014:00 | N/A |
| 2025-10-29 14:00:00October 29, 2025 | Aerodrom  | 2 - 1 | Kumanovo | 14:00:0014:00 | N/A |
| 2025-10-23 15:00:00October 23, 2025 | Bashkimi (Lj)  | 2 - 3 | Kumanovo | 15:00:0015:00 | N/A |
| 2025-10-12 15:00:00October 12, 2025 | Kumanovo | 4 - 0 |  Hotla | 15:00:0015:00 | N/A |
| 2025-10-05 10:00:00October 5, 2025 | Kadino (S)  | 1 - 3 | Kumanovo | 10:00:0010:00 | N/A |
| 2025-09-28 16:00:00September 28, 2025 | Kumanovo | 1 - 0 |  Fortuna | 16:00:0016:00 | N/A |
| 2025-09-24 16:00:00September 24, 2025 | Studeniçan  | 1 - 1 | Kumanovo | 16:00:0016:00 | N/A |
| 2025-09-21 16:00:00September 21, 2025 | Kumanovo | 3 - 1 |  Pchinja | 16:00:0016:00 | N/A |
| 2025-09-14 16:00:24September 14, 2025 | Kumanovo | 4 - 0 |  Besa (S) | 16:00:2416:00 | N/A |
| 2025-09-07 17:00:04September 7, 2025 | R’zhanichino | 2 - 1 | Kumanovo | 17:00:0417:00 | N/A |
| 2025-08-24 17:00:37August 24, 2025 | Kumanovo | - | Llopati 97 | 17:00:3717:00 | N/A |
| 2025-08-17 17:30:56August 17, 2025 | Prevalec  | 3 - 6 | Kumanovo | 17:30:5617:30 | N/A |
| 2025-05-18 16:00:00May 18, 2025 | New Stars  | 0 - 1 | Kumanovo | 16:00:0016:00 | N/A |
| 2025-05-11 17:00:00May 11, 2025 | Kumanovo | 3 - 0 (awarded) |  Akademija Ilinden | 17:00:0017:00 | N/A |
| 2025-05-07 16:00:00May 7, 2025 | R’zhanichino | 2 - 5 | Kumanovo | 16:00:0016:00 | N/A |
| 2025-05-04 16:00:00May 4, 2025 | Kumanovo | 5 - 6 | Besa | 16:00:0016:00 | N/A |
| 2025-04-27 16:00:00April 27, 2025 | Fortuna | 1 - 0 | Kumanovo | 16:00:0016:00 | N/A |
| 2025-04-23 16:00:00April 23, 2025 | Kumanovo | 3 - 0 (awarded) |  Rinia 98 | 16:00:0016:00 | N/A |
| 2025-04-18 16:00:00April 18, 2025 | Euromilk | 0 - 2 | Kumanovo | 16:00:0016:00 | N/A |
| 2025-04-13 16:00:00April 13, 2025 | Kumanovo | 2 - 3 | Kadino (S) | 16:00:0016:00 | N/A |
| 2025-04-06 15:30:00April 6, 2025 | Pchinja | 4 - 0 | Kumanovo | 15:30:0015:30 | N/A |
| 2025-03-29 14:30:00March 29, 2025 | Kumanovo | 2 - 0 | Bashkimi (Lj) | 14:30:0014:30 | N/A |
| 2025-03-25 15:00:47March 25, 2025 | Kumanovo | 0 - 3 |  Shkëndija 77 | 15:00:4715:00 | N/A |
| 2025-03-09 14:30:58March 9, 2025 | BVK Konjare | 3 - 3 | Kumanovo | 14:30:5814:30 | N/A |
| 2025-03-02 14:00:19March 2, 2025 | Kumanovo | 2 - 1 | Aerodrom | 14:00:1914:00 | N/A |
| 2025-02-23 13:00:27February 23, 2025 | Kumanovo | 4 - 0 |  Ovche Pole | 13:00:2713:00 | N/A |
| 2025-02-16 13:00:28February 16, 2025 | Kumanovo | 1 - 3 | BVK Konjare | 13:00:2813:00 | N/A |
| 2025-02-09 13:00:04February 9, 2025 | Kumanovo | 1 - 3 | Llopati 97 | 13:00:0413:00 | N/A |
| 2024-12-08 13:00:00December 8, 2024 | Kumanovo | 2 - 3 | New Stars | 13:00:0013:00 | N/A |
| 2024-11-23 14:00:00November 23, 2024 | Akademija Ilinden | 0 - 5 | Kumanovo | 14:00:0014:00 | N/A |
| 2024-11-17 14:00:00November 17, 2024 | Kumanovo | 6 - 0 | R’zhanichino | 14:00:0014:00 | N/A |
| 2024-11-10 14:00:00November 10, 2024 | Besa | 1 - 4 | Kumanovo | 14:00:0014:00 | N/A |
| 2024-11-03 14:00:00November 3, 2024 | Kumanovo | 1 - 2 | Fortuna | 14:00:0014:00 | N/A |
| 2024-10-27 14:00:00October 27, 2024 | Rinia 98 | 0 - 0 | Kumanovo | 14:00:0014:00 | N/A |
| 2024-10-23 15:00:00October 23, 2024 | Kumanovo | 4 - 4 | Euromilk | 15:00:0015:00 | N/A |
| 2024-10-20 10:00:00October 20, 2024 | Kadino (S) | 2 - 1 | Kumanovo | 10:00:0010:00 | N/A |
| 2024-10-13 15:00:00October 13, 2024 | Kumanovo | 2 - 0 | Pchinja | 15:00:0015:00 | N/A |
| 2024-10-06 15:00:00October 6, 2024 | Bashkimi (Lj) | 1 - 1 | Kumanovo | 15:00:0015:00 | N/A |
| 2024-09-29 15:00:00September 29, 2024 | Shkëndija 77 | 6 - 0 | Kumanovo | 15:00:0015:00 | N/A |
| 2024-09-22 15:30:00September 22, 2024 | Kumanovo | 3 - 3 | BVK Konjare | 15:30:0015:30 | N/A |
| 2024-09-15 15:30:00September 15, 2024 | Aerodrom | 2 - 3 | Kumanovo | 15:30:0015:30 | N/A |
| 2024-09-09 15:30:54September 9, 2024 | Kumanovo | 10 - 0 |  Ran Proizvod | 15:30:5415:30 | N/A |
| 2024-09-07 17:30:44September 7, 2024 | Rečica  | 1 (4) - 1 (2) | Kumanovo | 17:30:4417:30 | N/A |
| 2024-08-29 17:30:04August 29, 2024 | Kumanovo | 4 - 3 | Llopati 97 | 17:30:0417:30 | N/A |
| 2024-08-25 17:00:28August 25, 2024 | Kumanovo | 4 - 2 | Aerodrom | 17:00:2817:00 | N/A |
| 2024-05-25 17:00:20May 25, 2024 | Pobeda (2010)  | 2 - 1 | Kumanovo | 17:00:2017:00 | N/A |
| 2024-05-19 16:00:00May 19, 2024 | Bashkimi (Lj) | 0 - 3 | Kumanovo | 16:00:0016:00 | N/A |
| 2024-05-12 16:00:00May 12, 2024 | Kumanovo | 5 - 2 | Kadino (S) | 16:00:0016:00 | N/A |
| 2024-05-01 16:00:00May 1, 2024 | Besa | 1 - 2 | Kumanovo | 16:00:0016:00 | N/A |
| 2024-04-27 16:30:00April 27, 2024 | Kumanovo | 6 - 0 |  SSK Nova | 16:30:0016:30 | N/A |
| 2024-04-25 16:30:00April 25, 2024 | Kumanovo | 2 - 0 | Fortuna | 16:30:0016:30 | N/A |
| 2024-04-21 16:00:00April 21, 2024 | Rinia 98 | 0 - 2 | Kumanovo | 16:00:0016:00 | N/A |
| 2024-04-13 16:00:00April 13, 2024 | Kumanovo | 5 - 0 |  Rashtak | 16:00:0016:00 | N/A |
| 2024-04-07 15:30:00April 7, 2024 | BVK Konjare | 0 - 2 | Kumanovo | 15:30:0015:30 | N/A |
| 2024-03-31 15:00:00March 31, 2024 | Kumanovo | 1 - 0 | Euromilk | 15:00:0015:00 | N/A |
| 2024-03-24 15:00:00March 24, 2024 | Shkëndija 77 | 3 - 0 | Kumanovo | 15:00:0015:00 | N/A |
| 2024-03-16 15:00:00March 16, 2024 | Kumanovo | 3 - 1 | Aerodrom | 15:00:0015:00 | N/A |
| 2024-03-09 14:00:00March 9, 2024 | Petrovec  | 0 - 3 | Kumanovo | 14:00:0014:00 | N/A |
| 2024-03-03 14:00:00March 3, 2024 | Kumanovo | 8 - 1 | Akademija Ilinden | 14:00:0014:00 | N/A |
| 2023-12-02 13:30:00December 2, 2023 | Kumanovo | 3 - 1 | Bashkimi (Lj) | 13:30:0013:30 | N/A |
| 2023-11-26 10:00:00November 26, 2023 | Kadino (S) | 0 - 1 | Kumanovo | 10:00:0010:00 | N/A |
| 2023-11-19 13:30:00November 19, 2023 | Kumanovo | 2 - 0 | Besa | 13:30:0013:30 | N/A |
| 2023-11-11 13:30:00November 11, 2023 | SSK Nova | 0 - 5 | Kumanovo | 13:30:0013:30 | N/A |
| 2023-11-05 13:30:00November 5, 2023 | Kumanovo | 3 - 2 | Rinia 98 | 13:30:0013:30 | N/A |
| 2023-10-28 14:30:00October 28, 2023 | Fortuna | 1 - 3 | Kumanovo | 14:30:0014:30 | N/A |
| 2023-10-22 15:00:00October 22, 2023 | Rashtak | 0 - 3 | Kumanovo | 15:00:0015:00 | N/A |
| 2023-10-15 15:00:00October 15, 2023 | Kumanovo | 1 - 1 | BVK Konjare | 15:00:0015:00 | N/A |
| 2023-10-11 15:00:00October 11, 2023 | Euromilk | 2 - 1 | Kumanovo | 15:00:0015:00 | N/A |
| 2023-10-08 15:00:00October 8, 2023 | Kumanovo | 2 - 1 | Shkëndija 77 | 15:00:0015:00 | N/A |
| 2023-10-01 15:30:00October 1, 2023 | Aerodrom | 0 - 4 | Kumanovo | 15:30:0015:30 | N/A |
| 2023-09-24 16:00:00September 24, 2023 | Kumanovo | 3 - 0 | Petrovec | 16:00:0016:00 | N/A |
| 2023-09-16 16:00:49September 16, 2023 | Akademija Ilinden | 0 - 3 | Kumanovo | 16:00:4916:00 | N/A |
| 2023-05-24 17:00:00May 24, 2023 | Euromilk | 2 - 1 | Kumanovo | 17:00:0017:00 | N/A |
| 2023-05-21 17:00:00May 21, 2023 | Kumanovo | 4 - 3 | BVK Konjare | 17:00:0017:00 | N/A |
| 2023-05-17 17:00:00May 17, 2023 | SSK Nova | 3 - 2 | Kumanovo | 17:00:0017:00 | N/A |
| 2023-05-14 17:00:00May 14, 2023 | Kumanovo | 2 - 2 | Besa | 17:00:0017:00 | N/A |
| 2023-05-07 17:00:00May 7, 2023 | Petrovec | 5 - 3 | Kumanovo | 17:00:0017:00 | N/A |
| 2023-05-03 16:30:00May 3, 2023 | Kumanovo | 4 - 1 | Fortuna | 16:30:0016:30 | N/A |
| 2023-04-30 16:00:00April 30, 2023 | Kumanovo | 3 - 0 | Rashtak | 16:00:0016:00 | N/A |
| 2023-04-23 10:00:00April 23, 2023 | Kadino (S) | 2 - 0 | Kumanovo | 10:00:0010:00 | N/A |
| 2023-04-09 16:00:00April 9, 2023 | Kumanovo | 4 - 0 |  Ilinden (S) | 16:00:0016:00 | N/A |
| 2023-04-05 16:00:00April 5, 2023 | Aerodrom | 1 - 0 | Kumanovo | 16:00:0016:00 | N/A |
| 2023-04-02 16:00:18April 2, 2023 | Kumanovo | 2 - 1 |  Madjari Solidarnost | 16:00:1816:00 | N/A |
| 2023-03-25 15:00:21March 25, 2023 | Bashkimi 1947  | 4 - 0 | Kumanovo | 15:00:2115:00 | N/A |
| 2023-03-19 15:00:36March 19, 2023 | Kumanovo | 4 - 2 | Bashkimi (Lj) | 15:00:3615:00 | N/A |
| 2023-03-12 11:00:02March 12, 2023 | Volkovo  | 0 - 1 | Kumanovo | 11:00:02Canceled | N/A |
| 2023-03-05 14:00:02March 5, 2023 | Kumanovo | 2 - 1 | Rinia 98 | 14:00:0214:00 | N/A |
| 2022-12-03 13:30:49December 3, 2022 | Kumanovo | 3 - 1 | Euromilk | 13:30:4913:30 | N/A |
| 2022-11-27 13:30:42November 27, 2022 | BVK Konjare | 1 - 0 | Kumanovo | 13:30:4213:30 | N/A |
| 2022-11-19 14:00:15November 19, 2022 | Kumanovo | 5 - 0 | SSK Nova | 14:00:1514:00 | N/A |
| 2022-11-13 14:00:21November 13, 2022 | Besa | 5 - 3 | Kumanovo | 14:00:2114:00 | N/A |
| 2022-11-06 14:00:51November 6, 2022 | Kumanovo | 1 - 1 | Petrovec | 14:00:5114:00 | N/A |
| 2022-10-30 14:00:44October 30, 2022 | Fortuna | 2 - 1 | Kumanovo | 14:00:4414:00 | N/A |
| 2022-10-23 14:30:14October 23, 2022 | Rashtak | 1 - 3 | Kumanovo | 14:30:1414:30 | N/A |
| 2022-10-16 14:30:18October 16, 2022 | Kumanovo | 3 - 1 | Kadino (S) | 14:30:1814:30 | N/A |
| 2022-10-11 14:30:32October 11, 2022 | Ilinden (S) | 0 - 5 | Kumanovo | 14:30:3214:30 | N/A |
| 2022-10-08 14:30:45October 8, 2022 | Kumanovo | 3 - 3 | Aerodrom | 14:30:4514:30 | N/A |
| 2022-10-02 15:00:40October 2, 2022 | Madjari Solidarnost | 1 - 0 | Kumanovo | 15:00:4015:00 | N/A |
| 2022-09-25 15:30:18September 25, 2022 | Kumanovo | 1 - 3 | Bashkimi 1947 | 15:30:1815:30 | N/A |
| 2022-09-18 15:30:46September 18, 2022 | Bashkimi (Lj) | 2 - 0 | Kumanovo | 15:30:4615:30 | N/A |
| 2022-09-11 16:00:27September 11, 2022 | Kumanovo | 8 - 2 | Volkovo | 16:00:2716:00 | N/A |
| 2022-09-04 16:00:40September 4, 2022 | Rinia 98 | 0 - 3 | Kumanovo | 16:00:4016:00 | N/A |
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