Stadium: Court 3 Round: 24 Ground: Hardcourt outdoor
| Challenger Winnetka | 2019/07/10 18:50 | Michael Redlicki v Ramkumar Ramanathan | 5-7,5-7 |
| Challenger Winnetka | 2019/07/08 16:55 | Michael Redlicki v Evan King | 7-5,6-4 |
| ITF M25 Tulsa | 2019/06/20 16:40 | Ezekiel Clark v Michael Redlicki | 3-6,6-1,6-2 |
| ITF M25 Tulsa | 2019/06/19 15:00 | Emil Reinberg v Michael Redlicki | 6-3,2-6,3-6 |
| Challenger Columbus | 2019/06/11 16:30 | Dennis Novikov v Michael Redlicki | 6-4,6-3 |
| Challenger Little Rock | 2019/06/04 21:45 | Michael Redlicki v Francisco Cerundolo | 3-6,6-2,2-6 |
| Challenger Puerto Vallarta | 2019/04/29 18:00 | Skander Mansouri v Michael Redlicki | 6-4,6-4 |
| Challenger Sarasota | 2019/04/15 15:00 | Nick Hardt v Michael Redlicki | 3-6,6-3,6-3 |
| Challenger Milan | 2019/06/30 15:30 | Hugo Dellien v Danilo Petrovic | 7-5,6-4 |
| Challenger Milan | 2019/06/29 14:00 | Danilo Petrovic v Sumit Nagal | 7-5,6-2 |
| Challenger Milan | 2019/06/28 14:00 | Danilo Petrovic v Frederico Ferreira Silva | 6-3,6-4 |
| Challenger Milan | 2019/06/27 08:00 | Danilo Petrovic v Nino Serdarusic | 6-3,7-5 |
| Challenger Milan | 2019/06/26 09:30 | Duckhee Lee v Danilo Petrovic | 2-6,2-6 |
| Challenger Milan | 2019/06/24 10:45 | Danilo Petrovic v Jelle Sels | 4-6,6-3,6-4 |
| Challenger Parma | 2019/06/18 14:45 | Jacopo Berrettini v Danilo Petrovic | 6-4,7-5 |
| Challenger Prostejov | 2019/06/02 13:45 | Danilo Petrovic v Arthur Rinderknech | 4-6,4-6 |