Home History
| Estland - II Liiga | 2019/09/05 17:00 | JK Tallinna Kalev III v Raplamaa | D | 2-2 |
| Estland - II Liiga | 2019/08/31 11:00 | FC Kose v Raplamaa | W | 0-1 |
| Estland - II Liiga | 2019/08/27 16:00 | Raplamaa v Viimsi JK II | W | 2-0 |
| Estland - II Liiga | 2019/08/16 16:00 | Raplamaa v Parnu JK Poseidon | D | 6-6 |
| Estland - II Liiga | 2019/08/09 16:00 | Raplamaa v JK Tulevik Viljandi II | W | 2-0 |
| Estland - Cup | 2019/08/06 16:00 | Viimsi JK v Raplamaa | L | 2-0 |
| Estland - II Liiga | 2019/08/02 16:00 | Raplamaa v JK Piraaja Tallinn | L | 2-5 |
| Estland - II Liiga | 2019/07/23 15:33 | Laanemaa Haapsalu v Raplamaa | L | 4-0 |
Away History
| Estland - II Liiga | 2019/09/08 10:00 | Laanemaa Haapsalu v FC Kuressaare II | W | 0-2 |
| Estland - II Liiga | 2019/08/22 16:00 | FC Kose v FC Kuressaare II | W | 0-2 |
| Estland - II Liiga | 2019/06/08 11:00 | Raasiku FC Joker v FC Kuressaare II | W | 1-5 |
| Estland - II Liiga | 2019/04/05 16:00 | Viimsi JK II v FC Kuressaare II | D | 1-1 |
| Estland - II Liiga | 2018/09/23 14:00 | FC Otepää v FC Kuressaare II | D | 3-3 |
| Estland - II Liiga | 2018/08/27 17:00 | Tabasalu FC Charma v FC Kuressaare II | L | 3-0 |
| Estland - II Liiga | 2018/08/20 14:00 | Parnu JK Vaprus II v FC Kuressaare II | L | 7-2 |
| Estland - II Liiga | 2018/05/20 14:00 | Viimsi JK v FC Kuressaare II | L | 5-0 |
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