Round: 44 Ground: Clay
| ITF - M25 Naples | 2019/10/27 14:00 | Oliver Crawford v Patrick Daciek | 6-2,6-0 |
| Challenger - Tiburon | 2019/09/24 17:00 | Edan Leshem v Oliver Crawford | 6-7,6-4,6-4 |
| ITF M25 Houston | 2019/09/21 01:00 | Oliver Crawford v Hugo Gaston | 3-6,2-6 |
| ITF M25 Houston | 2019/09/20 00:00 | Ricardo Rodriguez-Pace v Oliver Crawford | 6-3,6-7,6-7 |
| ITF M25 Houston | 2019/09/18 23:45 | Sumit Sarkar v Oliver Crawford | 3-6,5-7 |
| Challenger - Lexington | 2019/07/30 23:40 | Enzo Wallart v Oliver Crawford | 6-4,6-3 |
| ITF - M25 Champaign | 2019/07/28 16:00 | Oliver Crawford v Jenson Brooksby | 2-6,1-6 |
| ITF - M25 Champaign | 2019/07/27 19:00 | Liam Broady v Oliver Crawford | 6-3,4-6,2-6 |
| ITF - M15 Novi Sad | 2019/07/30 08:00 | Milan Drinic v Thomas Bosancic | 6-4,6-3 |
| ITF M25 Prijedor | 2019/05/08 09:45 | Thomas Bosancic v Besir Durguti | 4-6,7-5,6-3 |
| ITF M25 Prijedor | 2019/05/07 13:45 | Thomas Bosancic v Stefan Suvajac | 6-0,6-1 |
| ITF M15 Mornington | 2019/03/28 01:50 | Luca Castelnuovo v Thomas Bosancic | 7-6,1-6,6-4 |
| ITF M15 Mornington | 2019/03/26 05:20 | Rimpei Kawakami v Thomas Bosancic | 4-6,6-7 |
| ITF M15 Mornington | 2019/03/20 23:00 | Thomas Bosancic v Harry Bourchier | 4-6,3-6 |
| ITF M15 Mornington | 2019/03/20 01:05 | Thomas Bosancic v Cameron Green | 6-3,4-6,6-0 |
| ITF M15 Mornington | 2019/03/18 23:00 | Thomas Bosancic v Stefan Skadarka | 6-4,6-3 |