| 2024-12-08 13:00:00December 8, 2024 | Obrshani  | 0 - 3 awarded |  Bashkimi (GJ) | 13:00:0013:00 | N/A |
| 2024-11-24 13:00:00November 24, 2024 | Ultras  | 3 - 0 awarded | Obrshani | 13:00:0013:00 | N/A |
| 2024-11-17 13:00:00November 17, 2024 | Obrshani | 0 - 3 awarded |  Buchin | 13:00:0013:00 | N/A |
| 2024-11-10 13:00:00November 10, 2024 | Mladost 1930  | 3 - 0 awarded | Obrshani | 13:00:0013:00 | N/A |
| 2024-11-03 13:00:00November 3, 2024 | Obrshani | 0 - 3 awarded |  Rosoman 83 | 13:00:0013:00 | N/A |
| 2024-10-27 14:00:00October 27, 2024 | Prevalec  | 3 - 0 awarded | Obrshani | 14:00:0014:00 | N/A |
| 2024-10-20 14:00:00October 20, 2024 | Venec  | 3 - 0 awarded | Obrshani | 14:00:0014:00 | N/A |
| 2024-10-13 14:00:00October 13, 2024 | Obrshani | 3 - 0 awarded |  Sloga 1976 | 14:00:0014:00 | N/A |
| 2024-10-06 14:00:00October 6, 2024 | Golemo Konjari  | 7 - 0 | Obrshani | 14:00:0014:00 | N/A |
| 2024-09-29 15:00:00September 29, 2024 | Obrshani | 0 - 2 |  Pitu Guli | 15:00:0015:00 | N/A |
| 2024-09-22 15:00:00September 22, 2024 | Drenovo  | 6 - 4 | Obrshani | 15:00:0015:00 | N/A |
| 2024-09-15 15:00:00September 15, 2024 | Obrshani | 1 - 3 |  Vlaznimi Junior | 15:00:0015:00 | N/A |
| 2023-05-14 17:00:00May 14, 2023 | Buchin | 1 - 2 | Obrshani | 17:00:0017:00 | N/A |
| 2023-04-30 16:00:00April 30, 2023 | Mladost 1930 | 0 - 4 | Obrshani | 16:00:0016:00 | N/A |
| 2023-04-23 16:00:00April 23, 2023 | Obrshani | 0 - 3 | Prevalec | 16:00:0016:00 | N/A |
| 2023-04-15 16:00:00April 15, 2023 | Marena  | 5 - 0 | Obrshani | 16:00:0016:00 | N/A |
| 2023-04-09 15:00:00April 9, 2023 | Obrshani | 0 - 3 | Golemo Konjari | 15:00:0015:00 | N/A |
| 2023-04-02 15:00:00April 2, 2023 | Vardar (N)  | 7 - 0 | Obrshani | 15:00:0015:00 | N/A |
| 2023-03-26 15:00:00March 26, 2023 | Obrshani | 1 - 2 |  Lokomotiva (G) | 15:00:0015:00 | N/A |
| 2023-03-19 15:00:00March 19, 2023 | Sloga 1976 | 3 - 0 | Obrshani | 15:00:0015:00 | N/A |
| 2023-03-12 14:00:00March 12, 2023 | Obrshani | 0 - 2 | Rosoman 83 | 14:00:0014:00 | N/A |
| 2023-03-05 14:00:11March 5, 2023 | Pitu Guli | 3 - 0 | Obrshani | 14:00:1114:00 | N/A |
| 2022-11-13 13:00:00November 13, 2022 | Obrshani | 3 - 0 | Buchin | 13:00:0013:00 | N/A |
| 2022-11-06 13:00:00November 6, 2022 | Kanatlarci  | 2 - 5 | Obrshani | 13:00:0013:00 | N/A |
| 2022-10-30 13:00:00October 30, 2022 | Obrshani | 0 - 3 | Mladost 1930 | 13:00:0013:00 | N/A |
| 2022-10-23 14:00:00October 23, 2022 | Prevalec | 9 - 0 | Obrshani | 14:00:0014:00 | N/A |
| 2022-10-16 14:00:00October 16, 2022 | Obrshani | 1 - 0 | Marena | 14:00:0014:00 | N/A |
| 2022-10-09 14:00:00October 9, 2022 | Golemo Konjari | 4 - 0 | Obrshani | 14:00:0014:00 | N/A |
| 2022-10-02 15:00:00October 2, 2022 | Obrshani | 1 - 3 | Vardar (N) | 15:00:0015:00 | N/A |
| 2022-09-25 15:00:00September 25, 2022 | Lokomotiva (G) | 3 - 0 | Obrshani | 15:00:0015:00 | N/A |
| 2022-09-18 15:00:00September 18, 2022 | Obrshani | 2 - 4 | Sloga 1976 | 15:00:0015:00 | N/A |
| 2022-09-11 16:00:17September 11, 2022 | Rosoman 83 | 8 - 0 | Obrshani | 16:00:1716:00 | N/A |
| 2022-09-04 16:00:48September 4, 2022 | Obrshani | 1 - 4 | Pitu Guli | 16:00:4816:00 | N/A |
| 2022-06-15 17:30:44June 15, 2022 | Obrshani | 3 - 3 | Mladost 1930 | 17:30:4417:30 | N/A |
| 2022-06-12 17:30:34June 12, 2022 | Novo Crnilishte  | 3 - 0 | Obrshani | 17:30:3417:30 | N/A |
| 2022-06-05 17:30:46June 5, 2022 | Golemo Konjari | 4 - 0 | Obrshani | 17:30:4617:30 | N/A |
| 2022-06-01 17:30:10June 1, 2022 | Obrshani | 8 - 2 |  Vozarci | 17:30:1017:30 | N/A |
| 2022-05-29 17:30:33May 29, 2022 | Dinamo  | 4 - 3 | Obrshani | 17:30:3317:30 | N/A |
| 2022-05-24 17:30:48May 24, 2022 | Obrshani | 1 - 2 | Sloga 1976 | 17:30:4817:30 | N/A |
| 2022-05-21 17:30:14May 21, 2022 | Buchin | 1 - 1 | Obrshani | 17:30:1417:30 | N/A |
| 2022-05-15 17:00:16May 15, 2022 | Obrshani | 2 - 5 | Vardar (N) | 17:00:1617:00 | N/A |
| 2022-05-11 17:00:24May 11, 2022 | Prevalec | 13 - 1 | Obrshani | 17:00:2417:00 | N/A |
| 2022-05-08 17:00:12May 8, 2022 | Obrshani | 0 - 3 | Rosoman 83 | 17:00:1217:00 | N/A |
| 2022-04-30 17:00:17April 30, 2022 | Marena | 5 - 1 | Obrshani | 17:00:1717:00 | N/A |
| 2022-04-25 17:00:22April 25, 2022 | Pitu Guli | 3 - 1 | Obrshani | 17:00:2217:00 | N/A |
| 2022-04-22 16:30:01April 22, 2022 | Mladost 1930 | 1 - 2 | Obrshani | 16:30:0116:30 | N/A |
| 2022-04-17 16:30:56April 17, 2022 | Obrshani | 0 - 4 | Novo Crnilishte | 16:30:5616:30 | N/A |
| 2022-04-13 16:30:17April 13, 2022 | Napredok (KR)  | - | Obrshani | 16:30:17Canceled | N/A |
| 2022-04-10 16:00:34April 10, 2022 | Obrshani | 2 - 2 | Golemo Konjari | 16:00:3416:00 | N/A |
| 2022-04-06 16:00:26April 6, 2022 | Obrshani | 0 - 3 | Marena | 16:00:2616:00 | N/A |
| 2022-04-03 16:00:03April 3, 2022 | Vozarci | 2 - 3 | Obrshani | 16:00:0316:00 | N/A |
| 2022-03-30 16:00:41March 30, 2022 | Obrshani | 0 - 3 | Dinamo | 16:00:4116:00 | N/A |
| 2022-03-27 16:00:53March 27, 2022 | Sloga 1976 | 1 - 0 | Obrshani | 16:00:5316:00 | N/A |
| 2022-03-23 15:30:31March 23, 2022 | Obrshani | 3 - 1 | Buchin | 15:30:3115:30 | N/A |
| 2022-03-20 15:00:51March 20, 2022 | Vardar (N) | 0 - 0 | Obrshani | 15:00:5115:00 | N/A |
| 2022-03-13 15:00:44March 13, 2022 | Obrshani | 0 - 3 | Prevalec | 15:00:4415:00 | N/A |
| 2022-03-09 15:00:22March 9, 2022 | Rosoman 83 | 3 - 0 | Obrshani | 15:00:2215:00 | N/A |
| 2022-02-27 14:00:45February 27, 2022 | Obrshani | 0 - 1 | Pitu Guli | 14:00:4514:00 | N/A |
| 2021-04-18 14:00:19April 18, 2021 | Obrshani | 1 - 1 | Napredok (KR) | 14:00:1914:00 | N/A |
| 2021-04-11 14:00:25April 11, 2021 | Mladost (U)  | 4 - 0 | Obrshani | 14:00:2514:00 | N/A |
| 2021-04-04 16:00:08April 4, 2021 | Obrshani | 2 - 0 |  Dojransko Ezero | 16:00:0816:00 | N/A |
| 2021-03-31 16:00:17March 31, 2021 | Prevalec | 4 - 2 | Obrshani | 16:00:1716:00 | N/A |
| 2021-03-28 15:00:56March 28, 2021 | Obrshani | 0 - 1 | Dinamo | 15:00:5615:00 | N/A |
| 2021-03-24 15:00:05March 24, 2021 | Mladost 1930 | 0 - 1 | Obrshani | 15:00:0515:00 | N/A |
| 2021-03-17 15:00:57March 17, 2021 | Obrshani | 1 - 3 |  Bratstvo 07 | 15:00:5715:00 | N/A |
| 2021-03-14 15:00:04March 14, 2021 | Golemo Konjari | 2 - 2 | Obrshani | 15:00:0415:00 | N/A |
| 2021-03-07 14:00:06March 7, 2021 | Obrshani | 0 - 2 | Novo Crnilishte | 14:00:0614:00 | N/A |
| 2021-02-28 14:00:50February 28, 2021 | Vardar (N) | 2 - 1 | Obrshani | 14:00:5014:00 | N/A |
| 2020-12-20 13:00:04December 20, 2020 | Obrshani | 4 - 2 |  Ilinden BS | 13:00:0413:00 | N/A |
| 2020-12-13 13:00:53December 13, 2020 | Marena | 4 - 0 | Obrshani | 13:00:5313:00 | N/A |
| 2020-12-08 13:00:25December 8, 2020 | Obrshani | 3 - 5 | Lokomotiva (G) | 13:00:2513:00 | N/A |
| 2020-12-06 13:00:38December 6, 2020 | Pitu Guli | 0 - 0 | Obrshani | 13:00:3813:00 | N/A |
| 2020-11-25 13:30:08November 25, 2020 | Napredok (KR) | 0 - 2 | Obrshani | 13:30:0813:30 | N/A |
| 2020-11-22 13:30:13November 22, 2020 | Obrshani | 6 - 0 | Mladost (U) | 13:30:1313:30 | N/A |
| 2020-11-15 13:30:11November 15, 2020 | Dojransko Ezero | 0 - 2 | Obrshani | 13:30:1113:30 | N/A |
| 2020-11-08 14:00:44November 8, 2020 | Obrshani | 1 - 0 | Prevalec | 14:00:4414:00 | N/A |
| 2020-10-25 14:00:06October 25, 2020 | Dinamo | 2 - 1 | Obrshani | 14:00:0614:00 | N/A |
| 2020-10-21 15:00:15October 21, 2020 | Obrshani | 2 - 2 | Mladost 1930 | 15:00:1515:00 | N/A |
| 2020-10-18 15:00:50October 18, 2020 | Bratstvo 07 | 3 - 3 | Obrshani | 15:00:5015:00 | N/A |
| 2020-10-11 15:00:42October 11, 2020 | Obrshani | 1 - 0 | Golemo Konjari | 15:00:4215:00 | N/A |
| 2020-05-31 16:30:45May 31, 2020 | Obrshani | - | Dinamo | 16:30:4516:30 | N/A |
| 2020-05-24 16:30:07May 24, 2020 | Marena | - | Obrshani | 16:30:0716:30 | N/A |
| 2020-05-17 16:30:08May 17, 2020 | Obrshani | - | Mladost 1930 | 16:30:0816:30 | N/A |
| 2020-05-10 16:00:01May 10, 2020 | Novo Crnilishte | - | Obrshani | 16:00:0116:00 | N/A |
| 2020-05-03 16:00:43May 3, 2020 | Vardar (N) | - | Obrshani | 16:00:4316:00 | N/A |
| 2020-04-26 15:30:19April 26, 2020 | Obrshani | - | Prevalec | 15:30:1915:30 | N/A |
| 2020-04-18 15:30:44April 18, 2020 | Rosoman 83 | - | Obrshani | 15:30:4415:30 | N/A |
| 2020-04-11 15:00:16April 11, 2020 | Obrshani | - | Lokomotiva (G) | 15:00:1615:00 | N/A |
| 2020-04-05 15:00:09April 5, 2020 | Golemo Konjari | - | Obrshani | 15:00:0915:00 | N/A |
| 2020-03-29 14:30:27March 29, 2020 | Obrshani | - | Bratstvo 07 | 14:30:2714:30 | N/A |
| 2020-03-22 14:30:13March 22, 2020 | Gaber  | - | Obrshani | 14:30:1314:30 | N/A |
| 2020-03-15 14:00:06March 15, 2020 | Obrshani | - | Napredok (KR) | 14:00:0614:00 | N/A |
| 2020-03-08 14:00:05March 8, 2020 | Ilinden BS | 3 - 3 | Obrshani | 14:00:0514:00 | N/A |
| 2019-11-24 14:00:29November 24, 2019 | Dinamo | 3 - 1 | Obrshani | 14:00:2914:00 | N/A |
| 2019-11-17 13:00:48November 17, 2019 | Obrshani | 3 - 1 | Marena | 13:00:4813:00 | N/A |
| 2019-11-10 13:00:03November 10, 2019 | Mladost 1930 | 1 - 4 | Obrshani | 13:00:0313:00 | N/A |
| 2019-11-03 13:00:52November 3, 2019 | Obrshani | 4 - 0 | Novo Crnilishte | 13:00:5213:00 | N/A |
| 2019-10-26 14:30:30October 26, 2019 | Obrshani | 1 - 0 | Vardar (N) | 14:30:3014:30 | N/A |
| 2019-10-23 14:30:03October 23, 2019 | Obrshani | 4 - 0 | Ilinden BS | 14:30:0314:30 | N/A |
| 2019-10-20 14:30:34October 20, 2019 | Prevalec | 2 - 0 | Obrshani | 14:30:3414:30 | N/A |
| 2019-10-13 15:00:25October 13, 2019 | Obrshani | 0 - 3 | Rosoman 83 | 15:00:2515:00 | N/A |
| 2019-10-06 15:00:54October 6, 2019 | Lokomotiva (G) | 1 - 0 | Obrshani | 15:00:5415:00 | N/A |
| 2019-09-29 15:00:02September 29, 2019 | Obrshani | 2 - 1 | Golemo Konjari | 15:00:0215:00 | N/A |
| 2019-09-22 16:00:12September 22, 2019 | Bratstvo 07 | 2 - 1 | Obrshani | 16:00:1216:00 | N/A |
| 2019-09-15 16:00:09September 15, 2019 | Obrshani | 4 - 0 | Gaber | 16:00:0916:00 | N/A |
| 2019-09-08 16:00:18September 8, 2019 | Napredok (KR) | 1 - 1 | Obrshani | 16:00:1816:00 | N/A |
