Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| Challenger Bergamo | 2021/11/02 18:05 | Christopher O'Connell v Yannick Maden | 6-3,7-6 |
| Challenger Ismaning | 2021/10/28 15:30 | Jonas Forejtek v Yannick Maden | 7-6,3-6,6-1 |
| ATP Metz | 2021/09/19 08:30 | Yannick Maden v Antoine Hoang | 2-6,4-6 |
| Challenger Rennes | 2021/09/13 16:45 | Yannick Maden v Andy Murray | 3-6,1-6 |
| US Open | 2021/08/25 19:35 | Go Soeda v Yannick Maden | 1-6,6-4,6-4 |
| Challenger Pozoblanco | 2021/07/20 18:40 | Emilio Nava v Yannick Maden | 6-1,7-6 |
| Challenger Amersfoort | 2021/07/13 12:50 | Antoine Hoang v Yannick Maden | 6-4,7-6 |
| Challenger Perugia | 2021/07/05 16:50 | Yannick Maden v Dominic Stephan Stricker | 6-7,1-6 |
| Challenger Ortisei | 2021/11/12 11:45 | Jack Draper v Federico Gaio | 6-7,7-6,6-2 |
| Challenger Ortisei | 2021/11/10 12:10 | Jack Draper v Lucas Miedler | 6-4,7-6 |
| Challenger Ortisei | 2021/11/08 13:00 | Emilio Gomez v Jack Draper | 4-6,2-6 |
| Challenger Eckental | 2021/11/02 11:50 | Tomas Machac v Jack Draper | 7-6,4-6,6-4 |
| Challenger Seville | 2021/09/07 09:00 | Michael Geerts v Jack Draper | 3-6,2-6 |
| Challenger Como | 2021/08/31 10:30 | Jack Draper v Andrea Vavassori | 4-6,6-2,3-6 |
| Challenger Barletta | 2021/08/23 15:15 | Mohamed Aziz Dougaz v Jack Draper | 6-3,6-2 |
| Wimbledon | 2021/06/28 12:30 | Novak Djokovic v Jack Draper | 4-6,6-1,6-2,6-2 |