Stadium: Court 3 Round: 26 Ground: Clay
| ITF - M15 Kalmar | 2019/05/15 08:15 | Groener, Jakob v Simon Freund | 3-6,3-6 |
| ITF - M15 Kalmar | 2019/05/14 08:15 | Simon Freund v Dermiens, Guillaume | 6-3,4-6,10-6 |
| ITF - M15 Kalmar | 2019/05/13 08:15 | Simon Freund v Erik Grevelius | 6-2,6-2 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/08 13:20 | Simon Freund v Karl Friberg | 3-6,7-5,5-7 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/17 10:10 | Simon Freund v Jacopo Berrettini | 3-6,3-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/11 10:50 | Lindell, Christian v Simon Freund | 6-3,0-6,6-2 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/10 11:40 | Cordonnier, Gregorio v Simon Freund | 2-6,5-7 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/08 14:00 | Simon Freund v Paul Valsecchi | 6-4,6-2 |
| ITF - M15 Kalmar | 2019/05/15 11:55 | Butsch, Justin v Slobodchikov, Ronald | 3-6,6-4,4-6 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/12 09:15 | Eriksson, Markus v Slobodchikov, Ronald | 6-4,3-6,6-1 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/11 08:15 | Slobodchikov, Ronald v Niklas-Salminen, Patrick | 7-6,6-4 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/10 10:45 | Hansson, Gustav v Slobodchikov, Ronald | 2-6,6-3,3-6 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/09 10:25 | Samuelsson, Christian v Slobodchikov, Ronald | 3-6,4-6 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/08 08:15 | Arvid Nordquist v Slobodchikov, Ronald | 2-6,6-7 |
| ITF - M25 Santa Margherita | 2019/04/23 16:55 | Veldheer, Mick v Slobodchikov, Ronald | 6-1,6-1 |
| ITF - M25 Santa Margherita | 2019/04/18 12:00 | Kirill Kivattsev v Slobodchikov, Ronald | 6-1,3-6,7-5 |