Stadium: Court 5 Round: 28 Ground: Hardcourt outdoor
| Challenger Aptos | 2018/08/04 16:00 | Henry Craig v Jacob Grills | 6-2,2-6,6-1 |
| ITF M15 Vale Do Lobo | 2019/02/22 13:20 | Henry Craig v Juan Bautista Otegui | 6-1,6-4 |
| ITF M15 Vale Do Lobo | 2019/02/21 11:00 | Henry Craig v Yshai Oliel | 7-5,6-3 |
| ITF M15 Vale Do Lobo | 2019/02/20 12:35 | Giovanni Fonio v Henry Craig | 6-4,3-6,2-6 |
| ITF M15 Vale Do Lobo | 2019/02/19 11:00 | Henry Craig v Antonio Cayetano March | 6-2,6-1 |
| ITF M15 Vale Do Lobo | 2019/02/18 15:30 | Henry Craig v Jonas Trinker | 6-1,6-3 |
| ITF M15 Claremont | 2019/02/09 20:50 | Colin Sinclair v Henry Craig | 6-4,6-2 |
| ITF M15 Claremont | 2019/02/08 21:20 | Henry Craig v Jenson Brooksby | 6-7,6-3,6-1 |
| ITF M15 Claremont | 2019/02/07 18:00 | Henry Craig v Alexios Halebian | 6-2,6-2 |
| ITF M15 Vale Do Lobo | 2019/02/22 11:00 | Lamine Ouahab v Jacob Grills | 3-6,2-6 |
| ITF M15 Vale Do Lobo | 2019/02/21 13:15 | Luis Faria v Jacob Grills | 6-3,4-6,2-6 |
| ITF M15 Vale Do Lobo | 2019/02/19 15:55 | Nicholas David Ionel v Jacob Grills | 7-5,6-7,4-6 |
| ITF M25 Barnstaple | 2019/02/12 10:00 | Jacob Grills v Tobias Simon | 6-7,3-6 |
| Challenger Launceston | 2019/01/29 23:00 | Jacob Grills v Tatsuma Ito | 2-6,4-6 |
| Challenger Launceston | 2019/01/28 23:00 | Jacob Grills v Alessandro Bega | 6-7,6-2,6-3 |
| Challenger Burnie | 2019/01/22 00:25 | Jacob Grills v Mohamed Safwat | 4-6,2-6 |
| Challenger Burnie | 2019/01/21 02:55 | Jacob Grills v Enrique Lopez-Perez | 6-2,6-1 |