Head to Head
| Sweden 2.div Södra Götaland | 2024/04/20 12:00 | IFK Simrishamn v Osterlen FF | W | 2-3 |
| Sweden 2.div Södra Götaland | 2023/08/18 16:30 | IFK Simrishamn v Osterlen FF | L | 4-1 |
| Sweden 2.div Södra Götaland | 2023/04/23 11:00 | Osterlen FF v IFK Simrishamn | L | 1-4 |
| Sweden Cup | 2022/07/02 12:00 | IFK Simrishamn v Osterlen FF | W | 0-4 |
Home History
| Sweden 2.div Södra Götaland | 2024/08/10 12:00 | FBK Balkan v Osterlen FF | L | 2-0 |
| Sweden 2.div Södra Götaland | 2024/08/02 17:00 | Nosaby v Osterlen FF | W | 0-3 |
| Club Friendly List | 2024/07/27 13:00 | IFK Malmö FK v Osterlen FF | W | 0-3 |
| Sweden 2.div Södra Götaland | 2024/06/29 14:00 | Osterlen FF v Räppe GOIF | W | 3-0 |
| Sweden 2.div Södra Götaland | 2024/06/19 17:00 | IF Lodde v Osterlen FF | W | 0-4 |
| Sweden 2.div Södra Götaland | 2024/06/15 12:00 | Osterlen FF v FK Karlskrona | D | 2-2 |
| Sweden 2.div Södra Götaland | 2024/06/06 12:00 | Hässleholms IF v Osterlen FF | L | 3-1 |
| Sweden 2.div Södra Götaland | 2024/06/01 14:00 | IFK Trelleborg v Osterlen FF | L | 7-1 |
Away History
| Sweden 2.div Södra Götaland | 2024/08/10 12:00 | IFK Simrishamn v Hogaborgs BK | L | 0-3 |
| Sweden 2.div Södra Götaland | 2024/08/03 12:00 | IFK Simrishamn v Kristianstad FC | L | 0-2 |
| Sweden 2.div Södra Götaland | 2024/06/29 14:00 | IFK Berga v IFK Simrishamn | D | 1-1 |
| Sweden 2.div Södra Götaland | 2024/06/20 17:30 | IFK Simrishamn v IFK Karlshamn | L | 1-2 |
| Sweden 2.div Södra Götaland | 2024/06/14 17:00 | IFK Hässleholm v IFK Simrishamn | W | 1-2 |
| Sweden 2.div Södra Götaland | 2024/06/08 12:00 | IFK Simrishamn v IFK Trelleborg | L | 2-5 |
| Sweden 2.div Södra Götaland | 2024/06/01 12:00 | IFK Simrishamn v FBK Balkan | L | 1-2 |
| Sweden 2.div Södra Götaland | 2024/05/26 12:00 | Räppe GOIF v IFK Simrishamn | W | 1-2 |