Stadium: Court 12 Round: 25 Ground: Hardcourt outdoor
| Challenger Fairfield | 2019/10/08 17:00 | Jack Draper v Alex Rybakov | 6-1,2-6,7-5 |
| ITF M25 Harlingen | 2019/09/29 00:20 | Adrian Andreev v Alex Rybakov | 6-3,6-1 |
| ITF M25 Harlingen | 2019/09/28 01:00 | Alex Rybakov v Caruana, Liam | 7-5,6-4 |
| ITF M25 Harlingen | 2019/09/26 15:00 | Arconada, Jordi v Alex Rybakov | 6-4,4-6,7-10 |
| ITF M25 Harlingen | 2019/09/25 23:25 | Alex Rybakov v Christian Langmo | 6-2,6-3 |
| Houston, Singles Qualifying M-ITF-USA-28A | 2019/09/20 01:55 | Alex Rybakov v Hugo Gaston | 3-6,6-7 |
| Houston, Singles Qualifying M-ITF-USA-28A | 2019/09/19 01:05 | Adrian Oetzbach v Alex Rybakov | 2-6,2-6 |
| Challenger Cary | 2019/09/09 17:40 | Alex Rybakov v Redlicki, Michael | 4-6,2-6 |
| Claremont, Singles Qualifying M-ITF-USA-06B | 2019/10/09 18:40 | Farren, Connor v Gray, Jonathan | 3-6,6-3,6-4 |
| ITF M25 Norman | 2019/10/03 16:45 | Gray, Jonathan v Stalder, Reese | 4-6,4-6 |
| ITF M25 Norman | 2019/10/01 16:30 | Glasspool, Lloyd v Gray, Jonathan | 3-6,2-6 |
| ITF M25 Harlingen | 2019/09/27 22:00 | Nanda, Govind v Gray, Jonathan | 6-3,4-6,6-2 |
| ITF M25 Harlingen | 2019/09/26 15:00 | Gray, Jonathan v Nick Hardt | 6-3,6-4 |
| ITF M25 Harlingen | 2019/09/25 15:30 | Bothwell, Peter v Gray, Jonathan | 6-3,4-6,4-6 |
| Houston, Singles Qualifying M-ITF-USA-28A | 2019/09/18 19:00 | Gray, Jonathan v Watson, Andrew | 2-6,3-6 |
| Jakarta, Singles Main, M-ITF-INA-02A | 2019/08/22 02:30 | Gray, Jonathan v Schmid, Aaron | 4-6,7-5,2-6 |