Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| 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 |
| Challenger Cary | 2019/09/09 18:55 | Jeffrey John Wolf v Evan Song | 4-6,3-6 |
| Challenger Como | 2019/08/29 10:00 | Blaz Rola v Daniel Altmaier | 6-3,3-6,4-6 |
| Challenger Como | 2019/08/27 12:30 | Daniel Altmaier v Aslan Karatsev | 1-6,7-6,6-3 |
| Challenger Como | 2019/08/26 15:30 | Francisco Cerundolo v Daniel Altmaier | 3-6,4-6 |
| Challenger Meerbusch | 2019/08/13 11:00 | Daniel Altmaier v Carlos Taberner | 3-6,4-6 |
| Challenger Augsburg | 2019/08/09 13:20 | Facundo Mena v Daniel Altmaier | 6-4,7-6 |
| Challenger Augsburg | 2019/08/08 12:30 | Daniel Altmaier v Filippo Baldi | 7-6,6-3 |
| Challenger Augsburg | 2019/08/07 11:00 | Lucas Miedler v Daniel Altmaier | 3-6,3-6 |
| Challenger Augsburg | 2019/08/06 10:25 | Mukund Sasikumar v Daniel Altmaier | 6-4,1-6,6-7 |