Home History
| Copa Libertadores U20 | 2023/07/04 19:00 | Caracas U20 v O'Higgins U20 | L | 4-1 |
| Copa Libertadores U20 | 2023/07/01 19:00 | Alianza Lima U20 v O'Higgins U20 | D | 0-0 |
| America Friendlies | 2022/12/17 12:00 | Botafogo RJ U20 v O'Higgins U20 | W | 0-2 |
| America Friendlies | 2022/12/15 12:00 | Vasco da Gama U20 v O'Higgins U20 | D | 1-1 |
| America Friendlies | 2022/12/13 12:00 | Fluminense U20 v O'Higgins U20 | L | 4-1 |
| Chile U20 League | 2020/03/14 13:09 | O'Higgins U20 v Huachipato U20 | W | 2-0 |
Away History
| Copa Libertadores U20 | 2023/07/04 22:00 | Penarol U20 v Alianza Lima U20 | W | 4-1 |
| Copa Libertadores U20 | 2023/07/01 22:00 | Penarol U20 v Caracas U20 | W | 5-1 |
| U20 Intercontinental Cup | 2022/08/21 19:30 | Penarol U20 v Benfica U20 | L | 0-1 |
| Copa Libertadores U20 | 2022/02/20 23:00 | Independiente Del Valle U20 v Penarol U20 | D | 1-1 |
| Copa Libertadores U20 | 2022/02/17 22:30 | Penarol U20 v Caracas U20 | W | 2-1 |
| Copa Libertadores U20 | 2022/02/12 22:30 | Internacional U20 v Penarol U20 | D | 1-1 |
| Copa Libertadores U20 | 2022/02/09 20:00 | LDU Quito U20 v Penarol U20 | W | 0-2 |
| Copa Libertadores U20 | 2022/02/06 22:30 | Penarol U20 v Millonarios U20 | W | 2-0 |