stadio: Court 3 Round: 27 Ground: Hardcourt indoor
| ITF M15 Parnu | 2020/11/05 12:00 | Karlis Ozolins v Simon Freund | 4-6,2-6 |
| 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 M15 Parnu | 2020/11/05 11:10 | Mattias Siimar v Kristjan Tamm | 6-3,6-7,6-3 |
| ITF M15 Parnu | 2020/11/04 08:00 | Mattias Siimar v Roni Mikael Hietaranta | 6-3,6-2 |
| ITF M15 East Lansing | 2019/11/20 21:15 | Cannon Kingsley v Mattias Siimar | 7-5,6-2 |
| ITF M15 Helsinki | 2019/08/20 08:30 | Mattias Siimar v Roni Rikkonen | 5-7,6-0,9-11 |
| ITF M15 Helsinki | 2019/08/19 10:00 | Mattias Siimar v Tomas Vanko | 6-1,6-0 |
| ITF M15 Parnu | 2019/07/15 07:00 | Mattias Siimar v Tadas Babelis | 6-2,3-6,13-15 |
| ITF Finlandia F2 | 2018/08/08 12:55 | Mattias Siimar v Gustav Gustav Hansson | 2-6,2-6 |
| ITF Finlandia F2 | 2018/08/06 08:00 | Siim Troost v Mattias Siimar | 6-2,1-6,0-6 |