Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| ITF - M15 Héraklion | 2019/05/15 07:00 | Addison, Aaron v Omni Kumar | 4-6,7-6,6-2 |
| ITF - M15 Héraklion | 2019/05/07 10:00 | Guenther, Valentin v Addison, Aaron | 6-3,7-6 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/29 01:40 | Addison, Aaron v Bourchier, Harry | 7-6,5-7,3-6 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/27 23:00 | Purcell, Rhett v Addison, Aaron | 6-7,1-6 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/27 00:40 | Takeda, Naoki v Addison, Aaron | 3-6,4-6 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/21 23:00 | Christopher O'Connell v Addison, Aaron | 7-6,6-4 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/21 00:40 | Addison, Aaron v Frawley, James | 7-6,6-4 |
| Mornington, Singles Qualifying M-ITF-AUS-04A | 2019/03/19 23:00 | Addison, Aaron v Holt-Crossman, Erik | 6-3,6-2 |
| ITF - M15 Héraklion | 2019/05/15 07:00 | Story, James v Craig, Henry | 6-4,6-7,3-6 |
| ITF - M15 Héraklion | 2019/05/12 07:30 | Pervolarakis, Michail v Craig, Henry | 6-2,7-5 |
| ITF - M15 Héraklion | 2019/05/11 07:30 | Alexandros Skorilas v Craig, Henry | 2-6,1-6 |
| ITF - M15 Héraklion | 2019/05/10 08:40 | Craig, Henry v Boyer, Dusty H | 6-3,3-6,6-3 |
| ITF - M15 Héraklion | 2019/05/09 10:25 | Craig, Henry v Jhun, Alexander | 6-3,7-5 |
| ITF - M15 Héraklion | 2019/05/07 10:00 | Craig, Henry v Dominik Palan | 6-4,6-4 |
| ITF M15 Cancun | 2019/04/19 14:00 | Michael Geerts v Craig, Henry | 6-2,7-6 |
| ITF M15 Cancun | 2019/04/18 17:15 | Farren, Connor v Craig, Henry | 3-6,2-6 |