Stadium: Court 20 Round: 25 Ground: Clay
| ITF M25 Vero Beach | 2019/04/30 18:05 | Grey Hamilton v Rowland Phillips | 3-6,4-6 |
| ITF M25 Vero Beach | 2019/04/29 16:00 | Grey Hamilton v Korey Lovett | 6-3,6-2 |
| ITF M15 Orange Park | 2019/04/16 14:00 | Grey Hamilton v Felipe Mantilla | 2-6,4-6 |
| ITF M15 Sunrise | 2019/04/08 15:00 | JanMagnus Johnson v Grey Hamilton | 6-2,7-5 |
| ITF M15 Arcadia | 2019/03/17 20:30 | Grey Hamilton v Antoine Bellier | 3-6,3-6 |
| ITF M15 Arcadia | 2019/03/16 19:00 | Grey Hamilton v Alan Kohen | 6-3,7-5 |
| ITF M15 Arcadia | 2019/03/15 19:20 | Gonzalo Lama v Grey Hamilton | 6-1,5-7,2-6 |
| ITF M15 Arcadia | 2019/03/14 16:00 | Christian Langmo v Grey Hamilton | 4-6,0-6 |
| ITF M25 Vero Beach | 2019/05/04 16:00 | Dmitry Popko v Paul Oosterbaan | 6-2,6-1 |
| ITF M25 Vero Beach | 2019/05/02 14:00 | Andrew Watson v Paul Oosterbaan | 4-6,3-6 |
| ITF M25 Vero Beach | 2019/05/01 18:00 | Jack Findel-Hawkins v Paul Oosterbaan | 2-6,6-7 |
| ITF M15 Orange Park | 2019/04/16 14:00 | Agustin Velotti v Paul Oosterbaan | 6-4,6-7,6-3 |
| ITF M15 Sunrise | 2019/04/09 15:00 | Paul Oosterbaan v Sandro Ehrat | 6-7,7-6,5-7 |
| ITF M15 Portimao | 2019/03/15 11:35 | Tiago Cacao v Paul Oosterbaan | 6-4,6-2 |
| ITF M15 Portimao | 2019/03/14 15:15 | Paul Oosterbaan v Lamine Ouahab | 6-2,7-6 |
| ITF M15 Portimao | 2019/03/12 11:00 | Simon A Ivanov v Paul Oosterbaan | 5-7,6-4,1-6 |