| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 8/8/25 | Shkendija vs Shkupi | First League | 5:1 | Yes | Yes |
| 4/27/25 | Shkendija vs Shkupi | First League | 3:3 | Yes | Yes |
| 11/27/24 | Shkendija vs Shkupi | First League | 2:0 | No | No |
| 9/15/24 | Shkupi vs Shkendija | First League | 1:1 | No | Yes |
| 5/4/24 | Shkupi vs Shkendija | First League | 0:2 | No | No |
| 12/3/23 | Shkupi vs Shkendija | First League | 1:0 | No | No |
| 9/2/23 | Shkendija vs Shkupi | First League | 0:0 | No | No |
| 5/7/23 | Shkupi vs Shkendija | First League | 2:1 | Yes | Yes |
| 2/19/23 | Shkupi vs Shkendija | First League | 2:0 | No | No |
| 11/9/22 | Shkupi vs Shkendija | Macedonian Cup | 0:3 | Yes | No |
| 9/17/22 | Shkendija vs Shkupi | First League | 0:0 | No | No |
| 5/8/22 | Shkendija vs Shkupi | First League | 0:0 | No | No |
| 12/8/21 | Shkupi vs Shkendija | First League | 1:1 | No | Yes |
| 9/14/21 | Shkendija vs Shkupi | First League | 0:0 | No | No |
| 6/21/21 | Shkupi vs Shkendija | Club Friendly | 0:2 | No | No |
| 5/16/21 | Shkendija vs Shkupi | First League | 1:1 | No | Yes |
| 11/22/20 | Shkendija vs Shkupi | First League | 1:1 | No | Yes |
| 8/9/20 | Shkupi vs Shkendija | First League | 2:2 | Yes | Yes |
| 12/1/19 | Shkendija vs Shkupi | First League | 4:0 | Yes | No |
| 9/28/19 | Shkupi vs Shkendija | First League | 2:0 | No | No |
| 4/27/19 | Shkendija vs Shkupi | First League | 5:1 | Yes | Yes |
| 3/10/19 | Shkupi vs Shkendija | First League | 1:0 | No | No |
| 11/4/18 | Shkendija vs Shkupi | First League | 3:0 | Yes | No |
| 9/2/18 | Shkupi vs Shkendija | First League | 1:2 | Yes | Yes |
| 6/3/18 | Shkupi vs Shkendija | Friendly International | 1:4 | Yes | Yes |
| 5/15/18 | Shkendija vs Shkupi | Friendly International | 2:0 | No | No |
| 3/24/18 | Shkendija vs Shkupi | Friendly International | 1:1 | No | Yes |
| 10/22/17 | Shkendija vs Shkupi | First League | 4:1 | Yes | Yes |
| 8/21/17 | Shkupi vs Shkendija | First League | 0:3 | Yes | No |
| 4/30/17 | Shkupi vs Shkendija | First League | 1:1 | No | Yes |
| 3/5/17 | Shkendija vs Shkupi | First League | 0:0 | No | No |
| 10/30/16 | Shkupi vs Shkendija | First League | 0:0 | No | No |
| 10/26/16 | Shkendija vs Shkupi | First League | 0:1 | No | No |
| 5/19/16 | Shkupi vs Shkendija | First League | 1:3 | Yes | Yes |
| 3/19/16 | Shkendija vs Shkupi | First League | 3:1 | Yes | Yes |
| 12/10/15 | Shkendija vs Shkupi | First League | 4:1 | Yes | Yes |
| 10/4/15 | Shkupi vs Shkendija | First League | 0:2 | No | No |