Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| ITF Portugal F12 | 2018/07/26 15:00 | Carr, Simon v Simon, Tobias | 4-6,3-6 |
| ATP - Dubaï | 2020/02/22 07:00 | Yannick Hanfmann v Carr, Simon | 7-6,6-1 |
| ITF M15 Cancun | 2020/02/06 16:50 | Felix Corwin v Carr, Simon | 6-3,7-5 |
| ITF M15 Cancun | 2020/02/05 20:00 | Boyer, Dusty H v Carr, Simon | 6-7,2-6 |
| ITF M15 Cancun | 2020/01/28 15:30 | Kirkov, Vasil v Carr, Simon | 6-4,7-5 |
| ITF M15 Cancun | 2020/01/23 19:00 | Carr, Simon v Christian Langmo | 7-6,4-6,4-6 |
| ITF M15 Cancun | 2020/01/22 16:50 | Carr, Simon v Arreche, Nicolas Alberto | 6-4,6-4 |
| ITF - M15 Héraklion | 2019/12/07 08:30 | Carr, Simon v Alibek Kachmazov | 5-7,3-6 |
| ITF - M15 Héraklion | 2019/12/06 08:00 | Stuart Parker v Carr, Simon | 4-6,4-6 |
| Challenger Calgary | 2020/02/27 17:00 | Simon, Tobias v Yusuke Takahashi | 4-6,6-7 |
| Challenger Calgary | 2020/02/26 00:10 | Manuel Guinard v Simon, Tobias | 7-6,6-7,6-7 |
| Challenger Calgary | 2020/02/24 17:35 | Simon, Tobias v Baadi, Taha | 7-6,6-2 |
| Drummondville, Canada | 2020/02/19 15:00 | Sebastian Korda v Simon, Tobias | 6-3,4-6,7-6 |
| Drummondville, Canada | 2020/02/17 16:00 | Razvan Baiant v Simon, Tobias | 2-6,2-6 |
| Challenger Launceston | 2020/02/05 02:40 | Simon, Tobias v Kimmer Coppejans | 4-6,7-6,3-6 |
| Challenger Launceston | 2020/02/03 03:30 | Simon, Tobias v Crnokrak, Alexander | 6-4,7-6 |
| Challenger - Burnie | 2020/01/27 03:40 | Pervolarakis, Michail v Simon, Tobias | 6-3,6-4 |