Stadium: Court 1 Round: 26 Ground: Clay
| Waco, Singles M-ITF-USA-41A | 2019/10/17 17:50 | Carr, Simon v Hady Habib | 6-7,3-6 |
| Waco, Singles M-ITF-USA-41A | 2019/10/16 15:00 | Jesper De Jong v Carr, Simon | 1-6,7-5,4-6 |
| Claremont, Singles Qualifying M-ITF-USA-06B | 2019/10/09 19:05 | Carr, Simon v Roelofse, Ruan | 4-6,6-7 |
| Tavira, Simples M-ITF-POR-14A | 2019/10/04 09:00 | Alexandre Muller v Carr, Simon | 6-2,6-3 |
| Tavira, Simples M-ITF-POR-14A | 2019/10/03 10:40 | Carr, Simon v Gil, Fred | 6-1,6-1 |
| Tavira, Simples M-ITF-POR-14A | 2019/10/02 08:30 | Carr, Simon v Amatiste, Gianmarco | 6-2,6-1 |
| ITF M25 Shrewsbury | 2019/09/26 11:55 | Carr, Simon v Ocleppo, Julian | 1-6,6-1,3-6 |
| ITF M25 Shrewsbury | 2019/09/25 09:30 | Carr, Simon v Murgett, Finn | 6-2,6-2 |
| ITF - M25 Naples | 2019/10/30 14:00 | Olivares, Jose v Witten, Jesse | 5-7,6-7 |
| ITF - M25 Naples | 2019/10/29 14:00 | Witten, Jesse v Melnic, Vladislav | 6-4,4-6,10-3 |
| ITF - M25 Naples | 2019/10/28 14:00 | Leote Prata, Martim v Witten, Jesse | 4-6,7-5,10-12 |
| ITF - M25 Naples | 2019/10/27 14:00 | Alexander Bernard v Witten, Jesse | 4-6,2-6 |
| ITF M15 Cancun | 2019/09/23 16:00 | Witten, Jesse v Banzer, Rodrigo | 6-2,6-7,8-10 |
| ITF M15 Cancun | 2019/09/23 14:00 | Martinez, Esdras v Witten, Jesse | 2-6,1-6 |
| ITF M15 Cancun | 2019/09/22 18:30 | Fortin, Michel-Alexandre v Witten, Jesse | 3-6,1-6 |
| ITF M15 Naples | 2019/01/16 17:30 | Nicolas Alvarez v Witten, Jesse | 6-3,6-3 |