| Sweden Folksam U21 | 2022/07/19 15:00 | Osters IF U21 v Trelleborgs U21 | W | 3-0 |
| Sweden Folksam U21 | 2022/03/15 15:00 | Trelleborgs U21 v Osters IF U21 | W | 0-5 |
| Sweden Folksam U21 | 2021/09/21 15:00 | Osters IF U21 v Trelleborgs U21 | L | 1-2 |
| Sweden Folksam U21 | 2021/06/08 15:00 | Trelleborgs U21 v Osters IF U21 | W | 0-3 |
| Sweden Folksam U21 | 2019/05/20 15:00 | Trelleborgs U21 v Osters IF U21 | L | 3-0 |
| Other Match | 2025/07/22 14:00 | IFK Varnamo U21 v Osters IF U21 | L | 2-0 |
| Other Match | 2025/05/06 13:00 | Osters IF U21 v Malmo FF U21 | L | 0-2 |
| Other Match | 2025/04/08 13:00 | Osters IF U21 v Helsingborg U21 | W | 4-1 |
| Other Match | 2025/03/03 13:30 | Mjallby U21 v Osters IF U21 | L | 3-0 |
| Other Match | 2024/07/23 13:00 | Landskrona BoIS U21 v Osters IF U21 | D | 2-2 |
| Sweden Folksam U21 | 2023/10/30 15:00 | Kalmar FF U21 v Osters IF U21 | L | 2-1 |
| Sweden Folksam U21 | 2023/09/12 15:00 | Mjallby U21 v Osters IF U21 | L | 2-0 |
| Sweden Folksam U21 | 2023/08/28 14:00 | Osters IF U21 v Kalmar FF U21 | L | 0-2 |
| Other Match | 2025/06/10 13:00 | Helsingborg U21 v Trelleborgs U21 | L | 3-0 |
| Other Match | 2025/04/28 13:00 | Trelleborgs U21 v Kalmar FF U21 | L | 0-2 |
| Other Match | 2025/03/31 13:00 | Mjallby U21 v Trelleborgs U21 | L | 5-0 |
| Other Match | 2025/03/11 14:00 | Trelleborgs U21 v IFK Varnamo U21 | L | 0-2 |
| Other Match | 2024/10/15 14:00 | Trelleborgs U21 v Landskrona BoIS U21 | L | 0-1 |
| Other Match | 2024/10/08 14:00 | Trelleborgs U21 v Mjallby U21 | L | 0-1 |
| Other Match | 2024/09/30 13:00 | Helsingborg U21 v Trelleborgs U21 | L | 2-1 |
| Other Match | 2024/07/30 14:00 | Halmstads U21 v Trelleborgs U21 | L | 3-1 |