Stadium: Court 20 Round: 25 Ground: Clay
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/04/30 18:05 | Hamilton, Grey v Rowland Phillips | 3-6,4-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/04/29 16:00 | Hamilton, Grey v Lovett, Korey | 6-3,6-2 |
| ITF - M15 Orange Park | 2019/04/16 14:00 | Hamilton, Grey v Mantilla, Felipe | 2-6,4-6 |
| ITF - M15 Sunrise | 2019/04/08 15:00 | Johnson, Janmagnus v Hamilton, Grey | 6-2,7-5 |
| Arcadia, Singles Qualifying M-ITF-USA-09A | 2019/03/17 20:30 | Hamilton, Grey v Antoine Bellier | 3-6,3-6 |
| Arcadia, Singles Qualifying M-ITF-USA-09A | 2019/03/16 19:00 | Hamilton, Grey v Kohen, Alan | 6-3,7-5 |
| Arcadia, Singles Qualifying M-ITF-USA-09A | 2019/03/15 19:20 | Gonzalo Lama v Hamilton, Grey | 6-1,5-7,2-6 |
| Arcadia, Singles Qualifying M-ITF-USA-09A | 2019/03/14 16:00 | Christian Langmo v Hamilton, Grey | 4-6,0-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/04 16:00 | Dmitry Popko v C. Oosterbaan, Paul | 6-2,6-1 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/02 14:00 | Watson, Andrew v C. Oosterbaan, Paul | 4-6,3-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/01 18:00 | Findel-Hawkins, Jack v C. Oosterbaan, Paul | 2-6,6-7 |
| ITF - M15 Orange Park | 2019/04/16 14:00 | Velotti, Agustin v C. Oosterbaan, Paul | 6-4,6-7,6-3 |
| ITF - M15 Sunrise | 2019/04/09 15:00 | C. Oosterbaan, Paul v Ehrat, Sandro | 6-7,7-6,5-7 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/15 11:35 | Cacao, Tiago v C. Oosterbaan, Paul | 6-4,6-2 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/14 15:15 | C. Oosterbaan, Paul v Ouahab, Lamine | 6-2,7-6 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/12 11:00 | Ivanov, Simon Anthony v C. Oosterbaan, Paul | 5-7,6-4,1-6 |