Stadium: Centre Court (2) Round: 25 Ground: Carpet indoor
| Challenger Canberra | 2019/01/07 03:00 | Hugo Grenier v Simon, Tobias | 6-4,6-7,6-4 |
| Challenger Canberra | 2019/01/06 00:10 | Evans, Thomas v Simon, Tobias | 3-6,2-6 |
| Challenger Noumea | 2018/12/31 23:00 | Simon, Tobias v Verbeek, Sem | 5-7,7-5,4-6 |
| Challenger Andria | 2018/11/20 21:00 | Simon, Tobias v Lorenzo Sonego | 6-7,7-5,5-7 |
| Challenger Andria | 2018/11/19 11:10 | Marc-Andrea Huesler v Simon, Tobias | 3-6,7-6,3-6 |
| Challenger Andria | 2018/11/18 14:15 | Simon, Tobias v Gojo, Borna | 7-6,6-4 |
| Challenger Andria | 2018/11/17 12:10 | Simon, Tobias v Lapalombella, Savino | 6-0,6-1 |
| Challenger Bratislava | 2018/11/04 09:00 | Aldin Setkic v Simon, Tobias | 7-6,6-4 |
| ITF Czech Republic F12 | 2018/11/26 09:00 | Heger, Tim v Sprlak Puk, Albert | 3-6,4-6 |
| ITF Greece F8 | 2018/11/15 09:40 | Pervolarakis, Michail v Heger, Tim | 6-2,6-2 |
| ITF Greece F8 | 2018/11/13 13:25 | Heger, Tim v Solberg, Christoffer | 7-6,6-1 |
| ITF Estonia F3 | 2018/11/06 09:00 | Tyurnev, Evgeny v Heger, Tim | 6-3,3-6,6-1 |
| ITF Estonia F3 | 2018/11/04 12:00 | Heger, Tim v Parko, Carl Bret | 6-3,6-3 |
| ITF Estonia F3 | 2018/11/03 14:00 | Heger, Tim v Mandma, Alexander Georg | 6-4,6-0 |
| ITF Germany F16 | 2018/10/21 10:30 | Erdbories, Tillmann v Heger, Tim | 7-6,7-6 |
| ITF Italy F31 | 2018/10/07 13:40 | Stefano Baldoni v Heger, Tim | 6-3,6-1 |