Stadium: Court 1 Round: 24 Ground: Hardcourt outdoor
| Challenger Columbus 3 | 2019/09/18 14:00 | Michael Mmoh v Edan Leshem | 7-5,7-6 |
| Challenger Columbus 3 | 2019/09/17 14:00 | Edan Leshem v Ryan Peniston | 6-1,6-3 |
| Davis Cup | 2019/09/13 15:00 | Mikael Ymer v Edan Leshem | 6-3,7-5 |
| ITF M25 Bagneres-De-Bigorre | 2019/09/06 08:30 | Evan Hoyt v Edan Leshem | 7-6,3-6,6-1 |
| ITF M25 Bagneres-De-Bigorre | 2019/09/05 09:30 | Axel Garcian v Edan Leshem | 2-6,2-6 |
| ITF M25 Bagneres-De-Bigorre | 2019/09/04 09:00 | Yanais Laurent v Edan Leshem | 3-6,2-6 |
| ITF M25 Ust-Kamenogorsk | 2019/08/30 05:00 | Grigoriy Lomakin v Edan Leshem | 5-7,0-6 |
| ITF M25 Ust-Kamenogorsk | 2019/08/29 05:40 | Martin Borisiouk v Edan Leshem | 1-6,4-6 |
| ITF M25 Houston | 2019/09/21 01:00 | Oliver Crawford v Hugo Gaston | 3-6,2-6 |
| ITF M25 Houston | 2019/09/20 00:00 | Ricardo Rodriguez-Pace v Oliver Crawford | 6-3,6-7,6-7 |
| ITF M25 Houston | 2019/09/18 23:45 | Sumit Sarkar v Oliver Crawford | 3-6,5-7 |
| Challenger Lexington | 2019/07/30 23:40 | Enzo Wallart v Oliver Crawford | 6-4,6-3 |
| ITF M25 Champaign | 2019/07/28 16:00 | Oliver Crawford v Jenson Brooksby | 2-6,1-6 |
| ITF M25 Champaign | 2019/07/27 19:00 | Liam Broady v Oliver Crawford | 6-3,4-6,2-6 |
| ITF M25 Champaign | 2019/07/26 20:30 | Oliver Crawford v Ruan Roelofse | 6-3,6-4 |
| ITF M25 Champaign | 2019/07/25 19:45 | Oliver Crawford v Errol Smith | 4-6,6-1,6-1 |