Stadium: Citta Di Forlì Round: 29 Ground: Clay
| ITF M25 Barnstaple | 2019/02/13 10:00 | Tim Van Rijthoven v Jack Draper | 6-2,6-4 |
| 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 |
| ATP Queens | 2021/06/18 17:20 | Cameron Norrie v Jack Draper | 6-3,6-3 |
| ATP Queens | 2021/06/16 14:05 | Alexander Bublik v Jack Draper | 6-7,6-7 |
| ATP Queens | 2021/06/14 11:00 | Jack Draper v Jannik Sinner | 7-6,7-6 |
| ITF M25 Jablonec Nad Nisou | 2021/05/20 08:00 | Uladzimir Ignatik v Jack Draper | 6-3,3-6,4-6 |
| Challenger Ismaning | 2021/10/26 12:45 | Yannick Hanfmann v Tim Van Rijthoven | 7-5,6-7,4-6 |
| Challenger Biel | 2021/09/25 11:15 | Marc-Andrea Huesler v Tim Van Rijthoven | 3-6,7-6,6-4 |
| Challenger Biel | 2021/09/24 16:00 | Tim Van Rijthoven v Joao Sousa | 7-6,6-4 |
| Challenger Biel | 2021/09/22 13:10 | Dennis Novak v Tim Van Rijthoven | 7-6,3-6,6-7 |
| Challenger Biel | 2021/09/21 09:00 | Tim Van Rijthoven v Hiroki Moriya | 6-1,6-3 |
| Challenger Rennes | 2021/09/14 11:40 | Gregoire Barrere v Tim Van Rijthoven | 7-6,7-5 |
| Challenger Barletta | 2021/08/25 09:00 | Tim Van Rijthoven v Flavio Cobolli | 1-6,2-6 |
| Challenger Barletta | 2021/08/23 14:05 | Tim Van Rijthoven v Emiliano Maggioli | 7-5,6-4 |