Stadium: Centre Ct Round: 25 Ground: Hardcourt outdoor
| Brisbane, Simples M-ITF-AUS-07A | 2019/10/03 00:00 | Grills, Jacob v Thomas Fancutt | 7-6,3-6,5-7 |
| Brisbane, Simples M-ITF-AUS-07A | 2019/10/01 03:50 | Grills, Jacob v Crnokrak, Alexander | 0-6,6-3,6-1 |
| Challenger Kaohsiung | 2019/09/16 02:45 | Grills, Jacob v King, Evan | 4-6,6-3,2-6 |
| Challenger Shanghai | 2019/09/09 06:05 | Grills, Jacob v Sekiguchi, Shuichi | 6-3,1-6,1-6 |
| Jinan, China | 2019/09/03 02:00 | Gabashvili, Teimuraz v Grills, Jacob | 6-4,5-7,6-1 |
| Baotou, Chine | 2019/08/26 02:00 | Grills, Jacob v Wu, Di | 6-7,4-6 |
| ATP - Los Cabos | 2019/07/29 00:00 | Dominik Koepfer v Grills, Jacob | 6-3,7-6 |
| ATP - Los Cabos | 2019/07/28 01:25 | Grills, Jacob v Lacko, Lukas | 6-3,6-2 |
| Brisbane, Simples M-ITF-AUS-07A | 2019/10/01 05:25 | Luke Saville v Ajeet Rai | 6-2,6-4 |
| Coupe Davis | 2019/09/15 04:10 | Fahresi, Ari v Ajeet Rai | 6-3,2-6,10-7 |
| Coupe Davis | 2019/09/14 03:00 | M Rifqi, Fitriadi v Ajeet Rai | 6-7,3-6 |
| Hua Hin, Singles M-ITF-THA-07A | 2019/09/06 03:00 | Kelly, Dayne v Ajeet Rai | 6-1,7-5 |
| Hua Hin, Singles M-ITF-THA-07A | 2019/09/05 03:00 | Ajeet Rai v Takeuchi, Kento (1987) | 7-5,6-2 |
| Hua Hin, Singles M-ITF-THA-07A | 2019/09/04 06:35 | Ajeet Rai v Purcell, Rhett | 6-3,6-4 |
| Hua Hin, Singles M-ITF-THA-07A | 2019/08/21 08:25 | Wang, Chukang v Ajeet Rai | 3-6,6-2,6-3 |
| Jakarta, Singles Main, M-ITF-INA-02A | 2019/08/16 02:30 | Roelofse, Ruan v Ajeet Rai | 6-3,6-3 |