| ITF M15 Parnu | 11/02 08:00 | 54 | Perez Sanz, David v Siimar, Kristofer | 6-3,6-3 | |
| ITF M15 Parnu | 07/15 07:00 | 54 | Siimar, Kristofer v Adrian Oetzbach | 1-6,1-6 | |
| ITF Finland F1 | 07/30 07:00 | 25 | Siimar, Kristofer v George Loffhagen | 1-6,0-6 | |
| ITF Lithuania F1 | 07/21 07:00 | 62 | Siimar, Kristofer v Lombe, Harrison | 4-6,5-7 | |
| ITF Estonia F1 | 07/18 08:00 | 26 | Siimar, Kristofer v Kalovelonis, Markos | 1-6,1-6 | |
| ITF Estonia F1 | 07/17 07:00 | 25 | Siimar, Kristofer v Igor Gimenez | 6-3,3-6,7-5 | |
| ITF Italy F13 | 06/02 07:30 | 62 | Solanki, Alex v Siimar, Kristofer | 2-6,6-2,6-4 | |
| ITF Finland F3 | 08/14 10:00 | 25 | Marcora, Roberto v Siimar, Kristofer | 6-1,6-4 | |
| ITF Finland F1 | 08/01 09:40 | 25 | Michon, Axel v Siimar, Kristofer | 5-7,7-6,6-0 | |
| ITF Estonia F1 | 07/25 09:25 | 25 | Dijkhuizen, Marc v Siimar, Kristofer | 6-1,7-5 | |
| ITF Poland F4 Qual | 07/02 13:00 | 62 | Siimar, Mattias v Siimar, Kristofer | 6-3,7-5 | |
| ITF Poland F3 Qual | 06/25 08:00 | 44 | Kazakov, Lev v Siimar, Kristofer | 7-5,6-3 | |
| ITF Poland F1 | 06/11 08:00 | 62 | Siimar, Kristofer v Frost, Linus | 1-6,6-3,0-6 | |
| Coupe Davis | 04/09 11:10 | 27 | Siimar, Kristofer v Oger, Thomas | 4-6,4-6 | |
| ITF Estonia F4 | 11/07 23:00 | 25 | Siimar, Kristofer v Niels Lootsma | Retired | |
| ITF Estonia F3 | 11/01 13:25 | 25 | Siimar, Kristofer v Ivanov, Vladimir | 0-6,4-6 | |
| ITF Estonia F2 | 10/24 15:00 | 25 | Zhyrmont, Dzmitry v Siimar, Kristofer | 6-0,6-0 | |
| ITF Estonia F1 | 07/23 22:00 | 44 | Orlita, Daniel v Siimar, Kristofer | Retired | |
| ITF Estonia F1 | 11/09 08:00 | 25 | Kozyukov, Vitaly v Siimar, Kristofer | 6-2,6-3 | |
| ITF Estonia F3 | 11/03 15:00 | 25 | Kenneth Raisma v Siimar, Kristofer | 6-2,6-0 | |
| ITF Lithuania F1 | 07/21 10:25 | - | Fortuna, Claudio v Siimar, Kristofer | 7-5,6-0 | |
| ITF Estonia F2 | 07/19 07:00 | - | Siimar, Kristofer v Saplin, Kirill | 5-7,1-6 | |
| ITF Estonia F1 | 07/13 07:00 | - | Tverijonas, Julius v Siimar, Kristofer | 4-6,6-4,6-2 |