| Challenger Traralgon | 2015/10/27 02:00 | Grills, Jacob v Bourchier, Harry | 7-5,6-3 |
| ITF Australia F2 | 2015/03/05 02:40 | Grills, Jacob v Bourchier, Harry | 3-6,2-6 |
| UTR Pro Tennis Series Melbourne | 2020/07/01 08:00 | Marc Polmans v Grills, Jacob | 7-5,5-3 |
| UTR Pro Tennis Series Melbourne | 2020/06/30 07:30 | Grills, Jacob v Joshua Charlton | 6-2,7-6 |
| UTR Pro Tennis Series Melbourne | 2020/06/29 02:00 | Blake Mott v Grills, Jacob | 7-6,6-3 |
| ITF M15 Cancun | 2020/03/11 20:40 | Peter Bertran v Grills, Jacob | 7-5,4-6,1-6 |
| Las Vegas, Singles M-ITF-USA-07A | 2020/03/05 20:50 | Butsch, Justin v Grills, Jacob | 7-5,7-5 |
| Las Vegas, Singles M-ITF-USA-07A | 2020/03/04 17:55 | Hovhannisyan, Mousheg v Grills, Jacob | 2-6,1-6 |
| Challenger Calgary | 2020/02/24 20:55 | Grills, Jacob v Niklas-Salminen, Patrick | 2-6,4-6 |
| Challenger Launceston | 2020/02/04 03:20 | Grills, Jacob v Tung-Lin Wu | 6-4,4-6,6-7 |
| UTR Pro Tennis Series Melbourne | 2020/07/01 02:00 | Luke Saville v Bourchier, Harry | 6-3,4-1 |
| UTR Pro Tennis Series Melbourne | 2020/06/30 01:30 | Kelly, Dayne v Bourchier, Harry | 7-5,6-7,0-1 |
| UTR Pro Tennis Series Melbourne | 2020/06/29 01:30 | Alex Bolt v Bourchier, Harry | 7-6,5-4 |
| Geelong, Singles Qualifying M-ITF-AUS-04A | 2020/03/12 01:30 | Bourchier, Harry v Smith, Jordan | 6-1,6-4 |
| Geelong, Singles Qualifying M-ITF-AUS-04A | 2020/03/10 02:30 | Bourchier, Harry v Nkomba, Benard Bruno | 6-2,6-2 |
| Monterrey, Mexico | 2020/03/04 19:20 | Adrian Mannarino v Bourchier, Harry | 6-2,6-4 |
| Monterrey, Mexico | 2020/03/03 16:00 | Daniel Altmaier v Bourchier, Harry | 6-2,4-6,2-6 |
| Challenger Calgary | 2020/02/25 19:45 | Bourchier, Harry v Alex Rybakov | 3-6,6-7 |