Stadium: Indoor 2 Round: 27 Ground: Hardcourt outdoor
| ITF Canada F1 Qual | 2018/02/25 15:00 | Michael Redlicki v Jacob Dunbar | 6-1,6-3 |
| Challenger Columbus 3 | 2019/09/17 14:00 | Jacob Dunbar v Ryan Shane | 5-7,4-6 |
| Challenger Columbus 3 | 2019/09/16 15:00 | Jacob Dunbar v Aleksandar Kovacevic | 4-6,6-3,6-2 |
| ITF M25 Memphis | 2019/08/14 23:00 | Kevin King v Jacob Dunbar | 1-6,6-4,6-3 |
| ITF M25 Memphis | 2019/08/13 20:10 | Takanyi Garanganga v Jacob Dunbar | 3-6,1-6 |
| ITF M25 Edwardsville | 2019/08/09 16:30 | Jacob Dunbar v Nathan Ponwith | 6-4,4-6,5-7 |
| ITF M25 Edwardsville | 2019/08/08 15:00 | Jacob Dunbar v Gianni Ross | 6-2,6-0 |
| ITF M25 Edwardsville | 2019/08/07 16:10 | Ryan Shane v Jacob Dunbar | 2-6,2-6 |
| ITF M25 Decatur | 2019/08/01 15:00 | Santiago Rodriguez Taverna v Jacob Dunbar | 6-3,1-6,7-6 |
| Challenger Tiburon | 2019/09/25 17:00 | Michael Redlicki v Marcos Giron | 4-6,5-7 |
| Challenger Tiburon | 2019/09/23 19:40 | Filip Peliwo v Michael Redlicki | 3-6,7-5,3-6 |
| Challenger Columbus 3 | 2019/09/17 19:10 | Michael Redlicki v Michael Geerts | 5-7,4-6 |
| Challenger Cary | 2019/09/11 20:00 | Bjorn Fratangelo v Michael Redlicki | 6-4,6-3 |
| Challenger Cary | 2019/09/09 17:40 | Alex Rybakov v Michael Redlicki | 4-6,2-6 |
| Challenger New Haven | 2019/09/03 19:00 | Evan Zhu v Michael Redlicki | 6-3,7-6 |
| Challenger Aptos | 2019/08/08 17:00 | Michael Redlicki v Taro Daniel | 6-3,5-7,6-7 |
| Challenger Aptos | 2019/08/06 22:10 | Michael Redlicki v Maxime Janvier | 6-3,6-4 |