Stadium: Court 6 Round: 25 Ground: Clay
| ITF M15 - Rochester | 2019/06/24 17:00 | Langford Hills v John Harrison Richmond | 6-1,6-3 |
| ITF M15 Orlando | 2019/06/18 13:00 | John Harrison Richmond v Trey Hilderbrand | 5-7,3-6 |
| ITF M15 Orlando | 2019/06/17 13:00 | John Harrison Richmond v Matthew Foster-Estwick | 2-6,4-6 |
| ITF - M15 Boekarest | 2019/05/21 07:00 | Simon Beaupain v John Harrison Richmond | 6-3,6-3 |
| ITF - M15 Boekarest | 2019/05/20 07:00 | Pietro Mugelli v John Harrison Richmond | 3-6,0-6 |
| ITF - M15 Kalmar | 2019/05/13 12:25 | Jesper Klov Nilsson v John Harrison Richmond | 7-5,6-7,10-8 |
| ITF M15 Karlskrona | 2019/05/08 11:45 | Justin Butsch v John Harrison Richmond | 6-4,7-5 |
| ITF M15 Karlskrona | 2019/05/07 10:55 | Jonathan Stenberg v John Harrison Richmond | 6-7,6-7 |
| ITF M15 - Rochester | 2019/06/29 19:00 | Simon Freund v Strong Kirchheimer | 1-6,5-7 |
| ITF M15 - Rochester | 2019/06/28 18:15 | Simon Freund v Ronan Jachuck | 6-2,6-4 |
| ITF M15 - Rochester | 2019/06/27 18:40 | Simon Freund v Zachary Svajda | 6-4,0-6,6-3 |
| ITF M15 - Rochester | 2019/06/26 20:15 | Maksim Tikhomirov v Simon Freund | 6-3,4-6,3-6 |
| ITF M25 - Tulsa | 2019/06/19 15:00 | Martin Redlicki v Simon Freund | 6-4,6-3 |
| ITF M25 - Tulsa | 2019/06/18 15:00 | Simon Freund v Abraham Asaba | 6-2,6-3 |
| ITF M25 - Tulsa | 2019/06/17 15:00 | Simon Freund v Sebastian Zapata | 6-1,6-0 |
| ITF M25 - Wichita | 2019/06/12 16:40 | Alexander Cozbinov v Simon Freund | 7-5,6-3 |