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