Stadium: Court 4 Round: 54 Ground: Clay
| ITF M15 Uberlingen | 2023/08/14 08:00 | Taym Alazmeh v Dario Drebenstedt | 6-3,6-0 |
| ITF M25 Antalya | 2023/02/05 07:00 | Dario Drebenstedt v Alexander Chepik | 5-7,7-6,10-8 |
| ITF M25 Antalya | 2023/01/29 07:30 | Dario Drebenstedt v Lucca Pinto | 3-6,0-6 |
| ITF M15 Monastir | 2023/01/15 10:30 | Pierre Delage v Dario Drebenstedt | 6-4,6-2 |
| ITF M25 Monastir | 2022/11/28 12:30 | Dario Drebenstedt v Jake Bhangdia | 2-6,6-4,7-10 |
| ITF M25 Monastir | 2022/11/28 08:00 | Jason Janis v Dario Drebenstedt | 6-4,2-6,5-10 |
| ITF M15 Monastir | 2022/11/21 15:05 | Dario Drebenstedt v Darrshan Suresh | 4-6,6-7 |
| ITF M15 Monastir | 2022/11/21 09:30 | Ping Chen Lin v Dario Drebenstedt | 0-6,1-6 |
| UTR Pro Florida | 2023/05/13 17:33 | Jerry Barton v Kevin Humpfner | 4-1 |
| UTR Pro Florida | 2023/05/12 18:00 | Mikel Anderson v Kevin Humpfner | 1-6,6-1,0-6 |
| UTR Pro Florida | 2023/05/11 20:20 | Oscar Brown v Kevin Humpfner | 7-6,6-5 |
| UTR Pro Florida | 2023/05/09 21:00 | Joao Ceolin v Kevin Humpfner | 4-6,7-5,7-6 |
| UTR Pro Florida | 2023/05/08 18:00 | Kevin Humpfner v Daniel Phillips | 6-0,6-2 |
| ITF M15 Sunrise | 2023/04/11 21:30 | Mikel Anderson v Kevin Humpfner | 2-6,2-6 |
| ITF M15 Sunrise | 2023/04/11 14:00 | Kevin Humpfner v Oren Vasser | 6-1,6-3 |
| UTR Pro Florida | 2023/04/01 14:53 | Kevin Humpfner v Roberto Cid Subervi | 2-6,0-6 |