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 |
| ITF M25 Fayetteville | 2019/10/24 15:00 | Oscar Mesquida Berg v Jacob Dunbar | 3-6,3-6 |
| ITF M25 Fayetteville | 2019/10/23 20:15 | Jacob Dunbar v Vasil Kirkov | 3-6,6-2,6-1 |
| 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 Fayetteville | 2019/10/24 16:35 | Justin Butsch v Michael Redlicki | 3-6,2-6 |
| ITF M25 Fayetteville | 2019/10/23 21:00 | Peter Bothwell v Michael Redlicki | 1-6,6-3,1-6 |
| Challenger Las Vegas | 2019/10/17 19:30 | Steve Johnson v Michael Redlicki | 6-4,6-4 |
| Challenger Las Vegas | 2019/10/15 20:10 | Michael Redlicki v Jeffrey John Wolf | 6-3,7-5 |
| Challenger Las Vegas | 2019/10/14 20:20 | Michael Redlicki v Filip Peliwo | 6-2,2-6,6-2 |
| Challenger Fairfield | 2019/10/07 19:15 | Zachary Svajda v Michael Redlicki | 7-6,6-2 |
| 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 |