Head to Head
| Sweden Cup | 2022/07/02 12:00 | IFK Simrishamn v Osterlen FF | W | 0-4 |
Home History
| Sweden 2.div Södra Götaland | 2023/04/15 12:00 | Kristianstad FC v Osterlen FF | L | 2-1 |
| Sweden 2.div Södra Götaland | 2023/04/10 11:00 | Osterlen FF v Hässleholms IF | L | 0-2 |
| Sweden 2.div Södra Götaland | 2023/04/01 11:00 | FBK Balkan v Osterlen FF | W | 0-1 |
| Sweden 2.div Södra Götaland | 2022/10/15 13:00 | Kristianstad FC v Osterlen FF | W | 1-2 |
| Sweden 2.div Södra Götaland | 2022/10/09 11:00 | Osterlen FF v Hässleholms IF | L | 0-4 |
| Sweden 2.div Södra Götaland | 2022/10/01 12:00 | Nosaby v Osterlen FF | L | 2-1 |
| Sweden 2.div Södra Götaland | 2022/09/25 12:00 | Osterlen FF v FC Rosengård 1917 | L | 1-2 |
| Sweden 2.div Södra Götaland | 2022/09/17 12:00 | Asarums IF FK v Osterlen FF | L | 3-2 |
Away History
| Sweden 2.div Södra Götaland | 2023/04/15 12:00 | IFK Simrishamn v Nosaby | W | 3-0 |
| Sweden 2.div Södra Götaland | 2023/04/07 12:00 | IFK Hässleholm v IFK Simrishamn | L | 3-1 |
| Sweden 2.div Södra Götaland | 2023/04/02 12:00 | IFK Simrishamn v FC Rosengård 1917 | D | 1-1 |
| Sweden 2.div Södra Götaland | 2022/10/29 13:00 | Högsby IK v IFK Simrishamn | W | 0-5 |
| Sweden 2.div Södra Götaland | 2022/10/22 13:00 | IFK Simrishamn v Högsby IK | W | 5-2 |
| Sweden Cup | 2022/07/02 12:00 | IFK Simrishamn v Osterlen FF | L | 0-4 |