Head to Head
| Sweden 2.div Södra Götaland | 2023/08/18 16:30 | IFK Simrishamn v Osterlen FF | W | 4-1 |
| Sweden 2.div Södra Götaland | 2023/04/23 11:00 | Osterlen FF v IFK Simrishamn | W | 1-4 |
| Sweden Cup | 2022/07/02 12:00 | IFK Simrishamn v Osterlen FF | L | 0-4 |
Home History
| Sweden 2.div Södra Götaland | 2024/04/13 11:00 | Hogaborgs BK v IFK Simrishamn | W | 1-2 |
| Sweden 2.div Södra Götaland | 2024/04/06 12:00 | IFK Simrishamn v IFK Berga | W | 3-2 |
| Sweden 2.div Södra Götaland | 2024/03/29 14:00 | Kristianstad FC v IFK Simrishamn | D | 0-0 |
| World Club Friendlies | 2024/03/03 12:30 | Lunds BK v IFK Simrishamn | L | 6-0 |
| Sweden 2.div Södra Götaland | 2023/10/22 12:00 | IFK Simrishamn v FK Karlskrona | L | 1-2 |
| Sweden 2.div Södra Götaland | 2023/10/15 12:00 | Räppe GOIF v IFK Simrishamn | D | 2-2 |
| Sweden 2.div Södra Götaland | 2023/10/08 12:00 | IFK Simrishamn v VMA IK | W | 4-0 |
| Sweden 2.div Södra Götaland | 2023/09/30 12:00 | Kristianstad FC v IFK Simrishamn | W | 1-2 |
Away History
| Sweden 2.div Södra Götaland | 2024/04/13 11:00 | Osterlen FF v FBK Balkan | W | 1-0 |
| Sweden 2.div Södra Götaland | 2024/04/07 12:00 | Räppe GOIF v Osterlen FF | W | 1-4 |
| Sweden 2.div Södra Götaland | 2024/03/29 12:00 | Osterlen FF v Nosaby | D | 1-1 |
| Sweden 2.div Södra Götaland | 2023/11/02 18:00 | Osterlen FF v Lilla Torg | W | 3-2 |
| Sweden 2.div Södra Götaland | 2023/10/28 11:00 | Lilla Torg v Osterlen FF | W | 0-3 |
| Sweden 2.div Södra Götaland | 2023/10/22 12:00 | IFK Berga v Osterlen FF | L | 2-1 |
| Sweden 2.div Södra Götaland | 2023/10/15 11:00 | Osterlen FF v IFK Malmö FK | W | 3-2 |
| Sweden 2.div Södra Götaland | 2023/10/07 11:00 | IFK Trelleborg v Osterlen FF | D | 4-4 |