| Estonia U19 League | 2021/09/28 14:00 | FA Kalev Tartu U19 v JK Laanemaa Hiiumaa U19 | L | 2-0 |
| Estonia U19 League | 2021/09/14 14:00 | FC Levadia Tallinn U19 v JK Laanemaa Hiiumaa U19 | L | 2-0 |
| Estonia U19 League | 2021/09/07 14:00 | FC Flora Tallinn U19 v JK Laanemaa Hiiumaa U19 | W | 1-7 |
| Estonia U19 League | 2021/08/24 15:00 | FC Flora Tallinn U19 v JK Laanemaa Hiiumaa U19 | L | 4-1 |
| Estonia U19 League | 2021/08/03 15:00 | Keila JK U19 v JK Laanemaa Hiiumaa U19 | D | 3-3 |
| Estonia U19 League | 2021/07/30 10:15 | JK Viljandi Tulevik U19 v JK Laanemaa Hiiumaa U19 | L | 3-1 |
| Estonia U19 League | 2021/06/29 14:00 | JK Nomme United U19 v JK Laanemaa Hiiumaa U19 | L | 2-1 |
| Estonia U19 League | 2021/09/21 14:12 | JK Nomme United U19 v FC Helios Tartu U19 | W | 0-1 |
| Estonia U19 League | 2021/08/24 15:00 | FC Helios Tartu U19 v Keila JK U19 | L | 1-3 |
| Estonia U19 League | 2021/08/11 16:00 | FC Helios Tartu U19 v JK Nomme United U19 | L | 0-5 |
| Estonia U19 League | 2021/08/03 14:00 | FA Kalev Tartu U19 v FC Helios Tartu U19 | L | 5-1 |
| Estonia U19 League | 2021/07/06 15:00 | FC Helios Tartu U19 v JK Viljandi Tulevik U19 | L | 0-4 |
| Estonia U19 League | 2021/06/29 16:00 | FC Levadia Tallinn U19 v FC Helios Tartu U19 | L | 10-0 |
| Estonia U19 League | 2021/06/22 15:00 | FC Helios Tartu U19 v Raplamaa U19 | W | 4-2 |
| Estonia U19 League | 2021/06/01 14:00 | FC Helios Tartu U19 v Pohja-Tallinna JK Volta U19 | W | 3-1 |