Stadium: Court 1 Round: 27 Ground: Clay
| ITF - Vero Beach M15 | 2023/04/27 13:35 | Benedikt Henning v Ricardo Rodriguez-Pace | 6-3,3-6,7-5 |
| ITF - Vero Beach M15 | 2023/04/26 17:05 | Mathieu Scaglia v Benedikt Henning | 7-6,4-6,2-6 |
| UTR Pro - Zadar | 2023/04/01 13:24 | Duje Ajdukovic v Benedikt Henning | 6-1,5-3 |
| UTR Pro - Zadar | 2023/03/28 06:00 | Duje Kekez v Benedikt Henning | 4-6,1-6 |
| UTR Pro - Zadar | 2023/03/27 08:59 | Benedikt Henning v Dusan Obradovic | 7-5,6-4 |
| ITF - Rovinj M15 | 2023/03/12 12:00 | Maj Premzl v Benedikt Henning | 5-7,6-2,10-7 |
| ITF - Porec M15 | 2023/03/05 12:00 | Benedikt Henning v Maj Premzl | 2-6,6-7 |
| UTR Pro - Dubaj | 2023/02/12 05:00 | Mihai Razvan Marinescu v Benedikt Henning | 6-3,5-7,2-6 |
| ITF - Vero Beach M15 | 2023/04/27 14:40 | Jacob Brumm v Colin Markes | 7-6,6-1 |
| ITF - Vero Beach M15 | 2023/04/26 14:00 | Jacob Brumm v Yi Zhou | 6-1,6-0 |
| ITF - Tacarigua M15 | 2023/04/18 20:00 | Jacob Brumm v Tauheed Browning | 4-6,2-6 |
| ITF - Sunrise M15 | 2023/04/13 17:40 | Jacob Brumm v Aidan Kim | 5-7,5-7 |
| ITF - Sunrise M15 | 2023/04/13 13:00 | Jacob Brumm v Elio Jose Ribeiro Lago | 6-4,6-0 |
| ITF - Calabasas M25 | 2023/03/23 17:00 | Lucas Renard v Jacob Brumm | 6-4,3-6,11-13 |
| ITF - Calabasas M25 | 2023/03/23 17:00 | Jacob Brumm v Aidan Mayo | 4-6,4-6 |
| ITF - Calabasas M25 | 2023/03/20 18:00 | Elijah Strode v Jacob Brumm | 2-6,2-6 |