Stadium: Court 1 Round: 27 Ground: Hardcourt indoor
| Challenger Las Vegas | 2019/10/15 20:10 | Michael Redlicki v Jeffrey John Wolf | 6-3,7-5 |
| Challenger Tiburon | 2019/09/25 21:10 | Maxime Cressy v Jeffrey John Wolf | 6-1,6-4 |
| Challenger Tiburon | 2019/09/24 20:25 | Alexander Sarkissian v Jeffrey John Wolf | 7-6,6-7,4-6 |
| Challenger Columbus 3 | 2019/09/22 16:00 | Jeffrey John Wolf v Peter Polansky | 3-6,6-7 |
| Challenger Columbus 3 | 2019/09/21 18:15 | Emilio Gomez v Jeffrey John Wolf | 2-6,6-7 |
| Challenger Columbus 3 | 2019/09/20 19:55 | Jeffrey John Wolf v Gabriel Petit | 4-6,6-4,6-1 |
| Challenger Columbus 3 | 2019/09/19 17:40 | Michael Mmoh v Jeffrey John Wolf | 2-6,2-6 |
| Challenger Columbus 3 | 2019/09/18 16:25 | Kyle Seelig v Jeffrey John Wolf | 3-6,2-6 |
| ATP Stockholm | 2019/10/18 16:30 | Denis Shapovalov v Cedrik-Marcel Stebe | 6-0,6-3 |
| ATP Stockholm | 2019/10/17 18:20 | Mikael Ymer v Cedrik-Marcel Stebe | 0-6,6-7 |
| ATP Stockholm | 2019/10/15 14:40 | Brayden Schnur v Cedrik-Marcel Stebe | 2-6,6-3,1-6 |
| ATP Stockholm | 2019/10/14 11:25 | Cedrik-Marcel Stebe v Oscar Otte | 6-4,4-6,6-1 |
| ATP Stockholm | 2019/10/13 13:05 | Hyeon Chung v Cedrik-Marcel Stebe | 6-3,3-6,3-6 |
| Challenger Mouilleron le Captif | 2019/10/10 10:35 | Dennis Novak v Cedrik-Marcel Stebe | 7-6,6-3 |
| Challenger Mouilleron le Captif | 2019/10/08 12:30 | Cedrik-Marcel Stebe v Kamil Majchrzak | 6-7,6-3,6-1 |
| Challenger Mouilleron le Captif | 2019/10/07 09:30 | Cedrik-Marcel Stebe v Sebastian Ofner | 7-5,6-1 |