Ground: Clay
| ITF Estonia F2 | 2014/07/22 07:00 | Saplin, Kirill v Drzewiecki, Karol | 0-6,3-6 |
| ITF Estonia F2 | 2014/07/20 07:00 | Alexander Bublik v Drzewiecki, Karol | 6-7,6-2,6-1 |
| ITF Poland F4 Qual | 2014/06/23 08:00 | Panfil, Grzegorz v Drzewiecki, Karol | 1-6,6-1,6-2 |
| ITF Poland F4 Qual | 2014/06/22 07:30 | Borkowski, Mikolaj v Drzewiecki, Karol | 4-6,7-5,4-6 |
| ITF Estonia F2 | 2014/07/24 14:45 | Ivanov, Vladimir v Sabanin, Yan | 6-4,6-2 |
| ITF Estonia F2 | 2014/07/23 07:00 | Ivanov, Vladimir v Reboul, Fabien | 6-1,6-3 |
| ITF Estonia F2 | 2014/07/22 10:25 | Ivanov, Vladimir v Mugevicius, Lukas | 6-3,3-6,6-3 |
| ITF Estonia F1 | 2014/07/16 09:20 | Ivanov, Vladimir v Basso, Andrea | 4-6,3-6 |
| ITF Estonia F1 | 2014/07/14 08:50 | Ivanov, Vladimir v Blomgren, Tobias | 4-6,6-1,6-1 |
| ITF Poland F3 | 2014/06/17 13:45 | Ivanov, Vladimir v Teurer, Rafal | 6-4,3-6,6-3 |
| Kazakhstan F6, Singles | 2014/04/18 05:00 | Ivanov, Vladimir v Nedelko, Ivan | 7-5,6-2 |
| Kazakhstan F6, Singles | 2014/04/17 05:00 | Vasilevski, Andrei v Ivanov, Vladimir | 4-6,0-6 |