Stadium: Court 5 Round: 28 Ground: Hardcourt outdoor
| Challenger Aptos | 2018/08/04 16:00 | Craig, Henry v Grills, Jacob | 6-2,2-6,6-1 |
| ITF M15 Vale Do Lobo | 2019/02/22 13:20 | Craig, Henry v Juan Bautista Otegui | 6-1,6-4 |
| ITF M15 Vale Do Lobo | 2019/02/21 11:00 | Craig, Henry v Yshai Oliel | 7-5,6-3 |
| ITF M15 Vale Do Lobo | 2019/02/20 12:35 | Giovanni Fonio v Craig, Henry | 6-4,3-6,2-6 |
| ITF M15 Vale Do Lobo | 2019/02/19 11:00 | Craig, Henry v March, Antonio Cayetano | 6-2,6-1 |
| ITF M15 Vale Do Lobo | 2019/02/18 15:30 | Craig, Henry v Jonas Trinker | 6-1,6-3 |
| ITF M15 Claremont | 2019/02/09 20:50 | Sinclair, Colin v Craig, Henry | 6-4,6-2 |
| ITF M15 Claremont | 2019/02/08 21:20 | Craig, Henry v Brooksby, Jenson | 6-7,6-3,6-1 |
| ITF M15 Claremont | 2019/02/07 18:00 | Craig, Henry v Halebian, Alexios | 6-2,6-2 |
| ITF M15 Vale Do Lobo | 2019/02/22 11:00 | Ouahab, Lamine v Grills, Jacob | 3-6,2-6 |
| ITF M15 Vale Do Lobo | 2019/02/21 13:15 | Faria, Luis v Grills, Jacob | 6-3,4-6,2-6 |
| ITF M15 Vale Do Lobo | 2019/02/19 15:55 | Nicholas David Ionel v Grills, Jacob | 7-5,6-7,4-6 |
| Barnstaple, Singles Qualifying M-ITF-GBR-01A | 2019/02/12 10:00 | Grills, Jacob v Simon, Tobias | 6-7,3-6 |
| Challenger Launceston | 2019/01/29 23:00 | Grills, Jacob v Tatsuma Ito | 2-6,4-6 |
| Challenger Launceston | 2019/01/28 23:00 | Grills, Jacob v Bega, Alessandro | 6-7,6-2,6-3 |
| Challenger - Burnie | 2019/01/22 00:25 | Grills, Jacob v Mohamed Safwat | 4-6,2-6 |
| Challenger - Burnie | 2019/01/21 02:55 | Grills, Jacob v Lopez Perez | 6-2,6-1 |