Round: 54 Ground: Clay
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/18 13:00 | Richmond, John Harrison v Trey Hilderbrand | 5-7,3-6 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/17 13:00 | Richmond, John Harrison v Foster-Estwick, Matthew | 2-6,4-6 |
| ITF - M15 Bucarest | 2019/05/21 07:00 | Simon Beaupain v Richmond, John Harrison | 6-3,6-3 |
| ITF - M15 Bucarest | 2019/05/20 07:00 | Pietro Mugelli v Richmond, John Harrison | 3-6,0-6 |
| Kalmar, Singles M-ITF-SWE-02A | 2019/05/13 12:25 | Klov Nilsson, Jesper v Richmond, John Harrison | 7-5,6-7,10-8 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/08 11:45 | Butsch, Justin v Richmond, John Harrison | 6-4,7-5 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/07 10:55 | Jonathan Stenberg v Richmond, John Harrison | 6-7,6-7 |
| Karlskrona, Singles Qualifying M-ITF-SWE-01A | 2019/05/06 12:20 | Nokic, Edis v Richmond, John Harrison | 7-5,3-6,4-10 |