Stadium: Centre Court Round: 24 Ground: Hardcourt outdoor
| Challenger - Burnie | 2020/01/27 03:40 | Pervolarakis, Michail v Simon, Tobias | 6-3,6-4 |
| ITF M25 Rancho Santa Fe | 2020/01/16 19:50 | Simon, Tobias v Emilio Nava | 6-7,6-7 |
| ITF M25 Rancho Santa Fe | 2020/01/15 22:25 | Bangoura, Sekou v Simon, Tobias | 3-6,2-6 |
| ITF M25 Rancho Santa Fe | 2020/01/14 20:00 | Simon, Tobias v Gomez, Lucas | 2-6,6-1,10-1 |
| ITF M25 Rancho Santa Fe | 2020/01/13 18:00 | Simon, Tobias v Kyle Kang | 6-3,6-3 |
| Ann Arbor, USA | 2020/01/08 18:10 | Simon, Tobias v Quiroz, Roberto | 4-6,7-6,6-7 |
| Ann Arbor, USA | 2020/01/06 22:25 | Simon, Tobias v King, Evan | 6-4,6-2 |
| ITF - M15 Héraklion | 2019/11/27 11:30 | Boris Pokotilov v Simon, Tobias | 6-4,6-4 |
| Challenger - Burnie | 2020/01/27 23:00 | Daniel Altmaier v Crnokrak, Alexander | 5-7,6-4,6-4 |
| Challenger Bendigo | 2020/01/15 03:30 | Christopher O'Connell v Crnokrak, Alexander | 6-4,6-3 |
| Challenger Bendigo | 2020/01/13 01:45 | Crnokrak, Alexander v Hugo Gaston | 6-4,7-6 |
| Challenger Bendigo | 2020/01/12 04:00 | Toshihide Matsui v Crnokrak, Alexander | 2-6,0-6 |
| Nonthaburi, Simples M-ITF-THA-06A | 2019/12/06 04:10 | Crnokrak, Alexander v Makoto Ochi | 6-7,3-6 |
| Nonthaburi, Simples M-ITF-THA-06A | 2019/12/05 06:45 | Crnokrak, Alexander v Taiyo Yamanaka | 6-2,6-3 |
| Nonthaburi, Simples M-ITF-THA-06A | 2019/12/04 04:00 | El Midhawy, Adam v Crnokrak, Alexander | 5-7,2-6 |
| Nonthaburi, Simples M-ITF-THA-06A | 2019/11/26 06:00 | Makoto Ochi v Crnokrak, Alexander | 6-4,6-4 |