Round: 1
| ITF - M15 Héraklion | 2020/02/19 15:35 | Gray, Jonathan v Alexander Shevchenko | 4-6,7-6,3-6 |
| ITF - M15 Héraklion | 2020/02/12 14:15 | Lodewijk Weststrate v Gray, Jonathan | 7-5,6-3 |
| ITF - M15 Manacor | 2020/01/14 11:00 | Abedallah Shelbayh v Gray, Jonathan | 7-6,2-6,6-1 |
| ITF - M15 Manacor | 2020/01/09 10:50 | Gray, Jonathan v Pawel Juszczak | 3-6,4-6 |
| ITF - M15 Manacor | 2020/01/08 08:55 | Gray, Jonathan v Abedallah Shelbayh | 6-2,5-7,7-5 |
| Fort Worth, Singles Qualifying M-ITF-USA-42A | 2019/10/22 18:30 | Liam Broady v Gray, Jonathan | 6-0,6-2 |
| Waco, Singles M-ITF-USA-41A | 2019/10/16 18:00 | Alex Rybakov v Gray, Jonathan | 6-1,7-5 |
| 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 Sunderland | 2020/02/28 10:00 | Jesper De Jong v Anton Matusevich | 6-7,7-6,7-6 |
| ITF - M25 Sunderland | 2020/02/27 11:25 | Anton Matusevich v Gijs Brouwer | 7-6,6-7,7-5 |
| ITF - M25 Sunderland | 2020/02/26 10:50 | Anton Matusevich v Patrick Foley | 7-5,7-5 |
| ITF M25 Glasgow | 2020/02/20 13:05 | Anton Matusevich v Hoyt, Evan | 6-7,2-6 |
| ITF M25 Glasgow | 2020/02/19 12:30 | Anton Matusevich v Tverijonas, Julius | 6-3,6-1 |
| Barnstaple, Singles Qualifying M-ITF-GBR-01A | 2020/02/11 14:20 | Anton Matusevich v Marek, Wojciech | 2-6,6-7 |
| ITF - M15 Bressuire | 2020/01/24 10:00 | Anton Matusevich v Lucas Poullain | 6-4,1-6,2-6 |
| ITF - M15 Bressuire | 2020/01/23 12:10 | Mertens, Yannick v Anton Matusevich | 7-6,6-7,5-7 |