Stadium: Hard 13 Round: 27 Ground: Hardcourt outdoor
| ITF - M15 Héraklion | 2019/05/16 07:00 | Glasspool, Lloyd v Crepaldi, Erik | 6-1,6-1 |
| ITF - M15 Héraklion | 2019/05/15 09:35 | Glasspool, Lloyd v Bothwell, Samuel | 6-3,6-4 |
| ITF - M15 Héraklion | 2019/05/10 07:00 | Glasspool, Lloyd v Jonas Trinker | 4-6,4-6 |
| ITF - M15 Héraklion | 2019/05/09 07:00 | Glasspool, Lloyd v Guenther, Valentin | 7-6,6-4 |
| ITF - M15 Héraklion | 2019/05/07 10:00 | Glasspool, Lloyd v Jesse Delaney | 6-4,6-0 |
| ITF - M25 Santa Margherita | 2019/05/02 13:15 | Glasspool, Lloyd v Federico Iannaccone | 3-6,2-6 |
| ITF - M25 Santa Margherita | 2019/05/01 15:05 | Glasspool, Lloyd v Gabriele Bosio | 6-3,6-3 |
| ITF - M25 Santa Margherita | 2019/04/25 12:00 | David Pichler v Glasspool, Lloyd | 6-2,6-3 |
| ITF - M15 Héraklion | 2019/05/16 07:00 | Addison, Aaron v Craig, Henry | 7-6,7-6 |
| 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 |