Stadium: Centre Court Round: 26 Ground: Hardcourt outdoor
| Singapore, Singles Qualifying M-ITF-SGP-01A | 2019/05/29 02:00 | Kawakami, Rimpei v Mohd Adam Das, Shamirul Shahril | 6-1,6-4 |
| ITF - M25 Luan | 2019/05/16 03:30 | Kawakami, Rimpei v He, Yecong | 7-5,2-6,4-6 |
| ITF - M25 Luan | 2019/05/15 07:40 | Kawakami, Rimpei v Natthasith Kunsuwan | 6-4,6-1 |
| Wuhan, Qualifications Simples M-ITF-CHN-05A | 2019/05/06 07:50 | Kousuke Ogura v Kawakami, Rimpei | 6-4,6-4 |
| Matsuyama, Singles M-ITF-JPN-06A | 2019/04/09 01:00 | Kawakami, Rimpei v Rinky Hijikata | 4-6,2-6 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/26 05:20 | Kawakami, Rimpei v Bosancic, Thomas | 4-6,6-7 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/20 23:00 | Kawakami, Rimpei v Thomas Fancutt | 3-6,4-6 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/20 02:05 | Kawakami, Rimpei v Alexander Klintcharov | 6-4,6-2 |
| Singapore, Singles Qualifying M-ITF-SGP-01A | 2019/05/29 02:00 | Hobbs, Roy v Gray, Jonathan | 3-6,4-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/05/01 08:30 | Gray, Jonathan v Louis Tessa | 6-2,1-6,2-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/23 11:55 | Gray, Jonathan v Louis Tessa | 4-6,3-6 |
| ITF M15 Madrid | 2019/04/17 11:40 | Benjamin Winter Lopez v Gray, Jonathan | 7-6,6-3 |
| ITF M15 Madrid | 2019/04/15 16:30 | Gray, Jonathan v Arthur Reymond | 6-3,6-2 |
| ITF M15 Madrid | 2019/04/15 11:00 | Gray, Jonathan v Blanco Damea, Alvaro | 6-3,6-7,13-11 |
| Bolton, Qualifications Simples M-ITF-GBR-03A | 2019/04/02 09:00 | Gray, Jonathan v Gijs Brouwer | 6-7,7-6,4-6 |
| ITF - M25 Calabasas | 2019/03/22 20:00 | Gray, Jonathan v Stefan Kozlov | 2-6,1-6 |