Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Austin | 2019/11/19 17:30 | Inoue, Haru v Woldeab, Siem | 4-6,1-6 |
| Waco, Singles M-ITF-USA-41A | 2019/10/13 15:00 | Woldeab, Siem v Smith, Tanner K | 1-6,2-6 |
| ITF M15 Claremont | 2019/02/05 20:30 | Brooksby, Jenson v Woldeab, Siem | 7-6,3-6,6-3 |
| Los Angeles, Singles M-ITF-USA-01A | 2019/01/02 23:20 | Dmitry Popko v Woldeab, Siem | 6-4,6-1 |
| ITF USA F26 | 2018/09/26 17:00 | Woldeab, Siem v Niki, Takuto | 2-6,2-6 |
| USA F26, Singles Qualifying | 2018/09/24 17:00 | Beiler, Mason v Woldeab, Siem | 4-6,0-6 |
| USA F26, Singles Qualifying | 2018/09/23 17:00 | Gupta, Aditya v Woldeab, Siem | 1-6,3-6 |
| USA F26, Singles Qualifying | 2018/09/22 19:30 | Woldeab, Siem v Ventre, Alessandro-Damiano | 6-3,7-6 |
| ITF M15 Austin | 2019/11/20 15:55 | Finn Bass v Allen, Leighton | 2-6,7-5,4-6 |
| ITF M15 Austin | 2019/11/19 16:00 | Adrian Oetzbach v Allen, Leighton | 6-4,2-6,5-10 |
| Fort Worth, Singles Qualifying M-ITF-USA-42A | 2019/10/21 15:00 | Zachary Svajda v Allen, Leighton | 6-4,4-6,10-6 |
| ITF M25 Norman | 2019/10/02 18:55 | Allen, Leighton v Eero Vasa | 5-7,1-6 |
| ITF M25 Harlingen | 2019/09/23 14:00 | Adrian Andreev v Allen, Leighton | 6-2,6-2 |
| ITF M25 Harlingen | 2019/09/22 15:00 | Kyle Overmyer v Allen, Leighton | 0-6,1-6 |
| ITF M15 Norman | 2019/07/08 14:00 | Andrew Fenty v Allen, Leighton | 7-6,6-2 |
| ITF M15 Pittsburgh | 2019/07/03 21:30 | Phillips, Luke v Allen, Leighton | 7-5,6-3 |