Estádio: Centre Court (2) Round: 25 Ground: Carpet indoor
| Challenger - Canberra | 2019/01/07 03:00 | Hugo Grenier v Tobias Simon | 6-4,6-7,6-4 |
| Challenger - Canberra | 2019/01/06 00:10 | Tom Evans v Tobias Simon | 3-6,2-6 |
| Challenger - Numeá | 2018/12/31 23:00 | Tobias Simon v Sem Verbeek | 5-7,7-5,4-6 |
| Challenger - Andria | 2018/11/20 21:00 | Tobias Simon v Lorenzo Sonego | 6-7,7-5,5-7 |
| Challenger - Andria | 2018/11/19 11:10 | Marc-Andrea Huesler v Tobias Simon | 3-6,7-6,3-6 |
| Challenger - Andria | 2018/11/18 14:15 | Tobias Simon v Borna Gojo | 7-6,6-4 |
| Challenger - Andria | 2018/11/17 12:10 | Tobias Simon v Savino Lapalombella | 6-0,6-1 |
| Challenger - Bratislava | 2018/11/04 09:00 | Aldin Setkic v Tobias Simon | 7-6,6-4 |
| ITF - República Checa F12 | 2018/11/26 09:00 | Tim Heger v Albert Sprlak Puk | 3-6,4-6 |
| ITF - Grécia F8 | 2018/11/15 09:40 | Michail Pervolarakis v Tim Heger | 6-2,6-2 |
| ITF - Grécia F8 | 2018/11/13 13:25 | Tim Heger v Christoffer Solberg | 7-6,6-1 |
| ITF - Estónia F3 | 2018/11/06 09:00 | Evgeny Tyurnev v Tim Heger | 6-3,3-6,6-1 |
| ITF - Estónia F3 | 2018/11/04 12:00 | Tim Heger v Carl Bret Parko | 6-3,6-3 |
| ITF - Estónia F3 | 2018/11/03 14:00 | Tim Heger v Alexander Georg Mandma | 6-4,6-0 |
| ITF - Alemanha F16 | 2018/10/21 10:30 | Tillmann Erdbories v Tim Heger | 7-6,7-6 |
| ITF - ItáliaF31 | 2018/10/07 13:40 | Stefano Baldoni v Tim Heger | 6-3,6-1 |