| UTR Pro San Diego | 2023/07/26 01:30 | Woldeab, Siem v Alexey Nesterov | 6-2,7-5 |
| UTR Pro San Diego | 2023/07/24 23:30 | Woldeab, Siem v Sacchitt Sharrma | 2-6,4-6 |
| ITF M15 Lakewood | 2023/07/13 19:15 | Woldeab, Siem v Keegan Smith | 3-6,2-6 |
| ITF M15 Lakewood | 2023/07/12 23:00 | Warren Wood v Woldeab, Siem | 4-6,7-6,0-6 |
| ITF M25 Austin | 2022/11/10 17:00 | Woldeab, Siem v Andres Andrade | 6-4,3-6,4-6 |
| ITF M25 Austin | 2022/11/09 19:00 | Woldeab, Siem v Hamish Stewart | 6-4,6-7,6-1 |
| ITF M15 Norman | 2022/10/25 16:45 | Ross, Gianni v Woldeab, Siem | 5-7,6-1,7-6 |
| ITF M15 San Diego | 2022/06/17 18:30 | Yuta Kikuchi v Woldeab, Siem | 2-6,6-2,6-4 |
| UTR Pro San Diego | 2023/07/25 22:30 | Sacchitt Sharrma v Andrei Volgin | 6-4,7-5 |