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