Head to Head
| Estonia II Liiga | 2019/09/15 10:00 | Raplamaa v FC Kuressaare II | L | 0-5 |
Home History
| Estonia II Liiga | 2020/06/27 08:00 | Raplamaa v Viimsi JK II | L | 2-3 |
| Estonia II Liiga | 2020/06/19 16:00 | JK Piraaja Tallinn v Raplamaa | W | 1-2 |
| Estonia II Liiga | 2020/06/14 10:00 | Raplamaa v FC Flora Tallinn III | W | 4-2 |
| Estonia II Liiga | 2020/06/10 17:15 | JK Saue v Raplamaa | W | 2-4 |
| Estonia II Liiga | 2020/06/07 10:00 | Raplamaa v Parnu JK Poseidon | W | 2-0 |
| Estonia II Liiga | 2020/05/26 16:00 | JK Tulevik Viljandi II v Raplamaa | D | 0-0 |
| Estonia II Liiga | 2020/05/23 09:00 | Raasiku FC Joker v Raplamaa | L | 6-3 |
| Europe Friendlies | 2020/03/01 11:05 | JK Piraaja Tallinn v Raplamaa | W | 2-4 |
Away History
| Estonia II Liiga | 2020/06/28 11:00 | Pohja Sakala v FC Kuressaare II | W | 2-3 |
| Estonia II Liiga | 2020/06/14 15:00 | Harju JK Laagri v FC Kuressaare II | L | 4-2 |
| Estonia II Liiga | 2020/05/24 13:00 | Viimsi JK II v FC Kuressaare II | W | 1-2 |
| Estonia II Liiga | 2019/10/09 15:00 | JK Piraaja Tallinn v FC Kuressaare II | W | 1-4 |
| Estonia II Liiga | 2019/09/27 14:00 | Parnu JK Vaprus II v FC Kuressaare II | D | 2-2 |
| Estonia II Liiga | 2019/09/15 10:00 | Raplamaa v FC Kuressaare II | W | 0-5 |
| Estonia II Liiga | 2019/09/08 10:00 | Laanemaa Haapsalu v FC Kuressaare II | W | 0-2 |
| Estonia II Liiga | 2019/08/22 16:00 | FC Kose v FC Kuressaare II | W | 0-2 |