Stadium: Court 2 Round: 26 Ground: Hardcourt indoor
| ITF M15 Parnu | 2020/11/04 12:45 | Jurgen Zopp v Karlis Ozolins | 6-3,3-6,4-6 |
| ITF M15 Sintra | 2020/09/15 08:30 | Eduard Esteve Lobato v Karlis Ozolins | 6-3,3-6,6-3 |
| ITF M15 Anif | 2020/08/27 14:25 | Karlis Ozolins v Sadio Doumbia | 2-6,4-6 |
| ITF M15 Anif | 2020/08/26 14:40 | Karlis Ozolins v Kai Lemstra | 7-5,6-3 |
| ITF M25 Vogau | 2020/08/17 09:00 | Timofey Skatov v Karlis Ozolins | 6-7,6-3,10-4 |
| ITF M25 Vogau | 2020/08/16 09:30 | Roko Horvat v Karlis Ozolins | 4-6,3-6 |
| Baltic Tennis League | 2020/06/26 12:25 | Robin Erik Parts v Karlis Ozolins | 6-4,6-0 |
| Baltic Tennis League | 2020/06/25 12:50 | Gustavs Lukstins v Karlis Ozolins | 6-7,7-6,3-6 |
| ITF M15 Parnu | 2020/11/04 13:05 | David Perez Sanz v Simon Freund | 6-7,3-6 |
| Challenger Nur-Sultan | 2020/03/11 09:25 | Botic Van De Zandschulp v Simon Freund | 6-2,7-5 |
| Challenger Nur-Sultan | 2020/03/10 06:40 | Timur Khabibulin v Simon Freund | 6-3,6-7,3-6 |
| ITF M25 Naples | 2020/02/09 15:00 | Jesse Witten v Simon Freund | 7-6,6-4 |
| ITF M25 Palm Coast | 2020/02/03 15:00 | Toby Alex Kodat v Simon Freund | 6-3,6-2 |
| ITF M25 Rancho Santa Fe | 2020/01/13 18:00 | Riley Smith v Simon Freund | 6-3,7-6 |
| ITF M25 Los Angeles | 2020/01/09 19:10 | Simon Freund v Christian Lindell | 3-6,4-6 |
| ITF M25 Los Angeles | 2020/01/08 20:00 | Keegan Smith v Simon Freund | 7-6,4-6,1-6 |