| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 5/3/25 | Pobeda vs Osogovo | Second League | 0:0 | No | No |
| 11/10/24 | Osogovo vs Pobeda | Second League | 4:1 | Yes | Yes |
| 3/5/24 | Osogovo vs Pobeda | Second League | 0:0 | No | No |
| 9/3/23 | Pobeda vs Osogovo | Second League | 1:0 | No | No |
| 4/16/22 | Pobeda vs Osogovo | Second League | 2:1 | Yes | Yes |
| 12/7/21 | Osogovo vs Pobeda | Second League | 1:3 | Yes | Yes |
| 9/25/21 | Pobeda vs Osogovo | Second League | 6:0 | Yes | No |
| 5/8/21 | Osogovo vs Pobeda | Second League | 0:1 | No | No |
| 12/5/20 | Osogovo vs Pobeda | Second League | 2:0 | No | No |
| 10/4/20 | Pobeda vs Osogovo | Second League | 1:1 | No | Yes |
| 2/22/20 | Pobeda vs Osogovo | Club Friendly | 3:1 | Yes | Yes |
| 11/30/19 | Pobeda vs Osogovo | Second League | 5:1 | Yes | Yes |
| 9/21/19 | Osogovo vs Pobeda | Second League | 1:0 | No | No |
| 8/21/19 | Osogovo vs Pobeda | Macedonian Cup | 1:0 | No | No |
| 8/7/19 | Osogovo vs Pobeda | Club Friendly | 6:0 | Yes | No |
| 4/24/18 | Osogovo vs Osogovo | Second League | 3:2 | Yes | Yes |