Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Charlottesville | 2019/10/28 21:20 | Evan Song v Michael Redlicki | 7-5,7-5 |
| ITF M25 Fayetteville | 2019/10/26 17:00 | Aleksandar Kovacevic v Michael Redlicki | 5-7,6-2,6-2 |
| ITF M25 Fayetteville | 2019/10/25 18:00 | Jacob Dunbar v Michael Redlicki | 3-6,2-6 |
| 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 Charlottesville | 2019/10/31 19:00 | Denis Kudla v Dmitry Popko | 6-4,6-7,1-6 |
| Challenger Charlottesville | 2019/10/31 00:40 | Denis Kudla v JC Aragone | 6-4,6-4 |
| Challenger Fairfield | 2019/10/10 18:40 | Kevin King v Denis Kudla | 6-2,6-3 |
| Challenger Fairfield | 2019/10/09 17:00 | Zachary Svajda v Denis Kudla | 1-6,6-3,4-6 |
| Challenger Tiburon | 2019/09/25 21:15 | Roberto Quiroz v Denis Kudla | 6-3,6-2 |
| Challenger New Haven | 2019/09/04 15:25 | Denis Kudla v Michael Mmoh | 5-7,0-6 |
| US Open | 2019/08/31 00:45 | Novak Djokovic v Denis Kudla | 6-3,6-4,6-2 |
| US Open | 2019/08/29 15:00 | Denis Kudla v Dusan Lajovic | 7-5,7-5,0-6,6-3 |