| Estonia U19 League | 2020/07/28 15:30 | Raplamaa U19 v Tallinna JK Legion U19 | W | 0-4 |
| Estonia U19 League | 2020/08/18 14:00 | FC Levadia Tallinn U19 v Tallinna JK Legion U19 | W | 0-2 |
| Estonia U19 League | 2020/08/11 14:00 | JK Nomme Kalju U19 v Tallinna JK Legion U19 | L | 2-1 |
| Estonia U19 League | 2020/08/04 14:00 | Tallinna JK Legion U19 v JK Nomme United U19 | W | 4-0 |
| Estonia U19 League | 2020/07/28 15:30 | Raplamaa U19 v Tallinna JK Legion U19 | W | 0-4 |
| Estonia U19 League | 2020/07/04 16:30 | Tartu JK Tammeka U19 v Tallinna JK Legion U19 | L | 1-0 |
| Estonia U19 League | 2020/06/30 14:00 | FC Flora Tallinn U19 v Tallinna JK Legion U19 | W | 0-7 |
| Estonia U19 League | 2020/06/10 17:00 | Tallinna JK Legion U19 v JK Tallinna Kalev U19 | W | 6-1 |
| Estonia U19 League | 2020/06/02 13:00 | Tallinna JK Legion U19 v FC Levadia Tallinn U19 | W | 4-0 |
| Estonia U19 League | 2020/08/11 14:00 | FC Levadia Tallinn U19 v Raplamaa U19 | L | 2-0 |
| Estonia U19 League | 2020/08/04 15:00 | Raplamaa U19 v JK Nomme Kalju U19 | L | 0-4 |
| Estonia U19 League | 2020/07/28 15:30 | Raplamaa U19 v Tallinna JK Legion U19 | L | 0-4 |
| Estonia U19 League | 2020/06/30 14:00 | JK Nomme United U19 v Raplamaa U19 | L | 10-0 |
| Estonia U19 League | 2020/06/20 14:30 | Raplamaa U19 v FC Flora Tallinn U19 | W | 4-1 |