Stadium: 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 | Perez Sanz, David v Simon Freund | 6-7,3-6 |
| Nur Sultan, Kazakhstan | 2020/03/11 09:25 | Botic Van De Zandschulp v Simon Freund | 6-2,7-5 |
| Nur Sultan, Kazakhstan | 2020/03/10 06:40 | Khabibulin, Timur v Simon Freund | 6-3,6-7,3-6 |
| ITF - M25 Naples | 2020/02/09 15:00 | Witten, Jesse v Simon Freund | 7-6,6-4 |
| Palm Coast, Singles M-ITF-USA-05A | 2020/02/03 15:00 | Kodat, Toby Alex v Simon Freund | 6-3,6-2 |
| ITF M25 Rancho Santa Fe | 2020/01/13 18:00 | Smith, Riley v Simon Freund | 6-3,7-6 |
| Los Angeles, Singles M-ITF-USA-01A | 2020/01/09 19:10 | Simon Freund v Lindell, Christian | 3-6,4-6 |
| ITF M15 Parnu | 2020/11/05 11:10 | Siimar, Mattias v Kristjan Tamm | 6-3,6-7,6-3 |
| ITF M15 Parnu | 2020/11/04 08:00 | Siimar, Mattias v Hietaranta, Roni Mikael | 6-3,6-2 |
| ITF M15 East Lansing | 2019/11/20 21:15 | Cannon Kingsley v Siimar, Mattias | 7-5,6-2 |
| ITF M15 Helsinki | 2019/08/20 08:30 | Siimar, Mattias v Rikkonen, Roni | 5-7,6-0,9-11 |
| ITF M15 Helsinki | 2019/08/19 10:00 | Siimar, Mattias v Vanko, Tomas | 6-1,6-0 |
| ITF M15 Parnu | 2019/07/15 07:00 | Siimar, Mattias v Tadas Babelis | 6-2,3-6,13-15 |
| ITF Finland F2 | 2018/08/08 12:55 | Siimar, Mattias v Hansson, Gustav | 2-6,2-6 |
| ITF Finland F2 | 2018/08/06 08:00 | Siim Troost v Siimar, Mattias | 6-2,1-6,0-6 |