| Estonia Cup | 2014/04/15 15:00 | FC Kuressaare v Tartu FC Santos | L | 1-3 |
| Estonia Esiliiga | 2014/11/09 11:00 | FC Kuressaare v JK Viljandi Tulevik | W | 5-3 |
| Estonia Esiliiga | 2014/11/02 11:00 | Parnu Linnameeskond v FC Kuressaare | D | 1-1 |
| Estonia Esiliiga | 2014/10/19 13:00 | FC Kuressaare v FC Flora Tallinn II | L | 2-3 |
| Estonia Esiliiga | 2014/10/05 13:00 | Vandra JK Vaprus v FC Kuressaare | W | 0-2 |
| Estonia Cup | 2014/10/01 13:00 | JK Nomme Kalju v FC Kuressaare | L | 4-0 |
| Estonia Esiliiga | 2014/09/28 13:00 | FC Kuressaare v JK Nomme Kalju II | L | 0-1 |
| Estonia Esiliiga | 2014/09/20 10:00 | FC Kuressaare v FC Levadia Tallinn U21 | L | 1-2 |
| Estonia Esiliiga | 2014/09/12 15:00 | FC Kuressaare v Rakvere JK Tarvas | L | 1-3 |
| UEFA Europa League Qualifying | 2014/07/10 17:00 | Tromso v Tartu FC Santos | L | 6-1 |
| UEFA Europa League Qualifying | 2014/07/03 15:00 | Tartu FC Santos v Tromso | L | 0-7 |
| Estonia Cup | 2014/06/05 16:00 | FC Flora Tallinn II v Tartu FC Santos | L | 13-12 |
| Estonia Cup | 2014/05/17 13:00 | FC Levadia Tallinn v Tartu FC Santos | L | 4-0 |
| Estonia Cup | 2014/05/01 16:00 | Viimsi JK v Tartu FC Santos | W | 1-3 |
| Estonia Cup | 2014/04/15 15:00 | FC Kuressaare v Tartu FC Santos | W | 1-3 |