Stadium: Court 1 Round: 24 Ground: Hardcourt outdoor
| ITF M25 Rancho Santa Fe | 2020/01/17 22:15 | Michael Redlicki v Ulises Blanch | 3-6,5-7 |
| ITF M25 Rancho Santa Fe | 2020/01/16 20:05 | Michael Redlicki v Riley Smith | 7-6,6-4 |
| ITF M25 Rancho Santa Fe | 2020/01/14 21:20 | Nino Serdarusic v Michael Redlicki | 4-6,2-6 |
| Challenger Ann Arbor | 2020/01/08 21:05 | Michael Redlicki v Patrick Kypson | 6-3,2-6,3-6 |
| Challenger Houston | 2019/11/16 00:50 | Michael Redlicki v Mitchell Krueger | 4-6,4-6 |
| Challenger Houston | 2019/11/15 19:05 | Tennys Sandgren v Michael Redlicki | 7-6,4-6,4-6 |
| Challenger Houston | 2019/11/12 19:45 | Govind Nanda v Michael Redlicki | 3-6,3-6 |
| Challenger Knoxville | 2019/11/05 17:45 | Andrea Vavassori v Michael Redlicki | 7-6,6-2 |
| US Open | 2019/08/19 16:15 | Dominik Koepfer v Ryan Harrison | 6-1,6-1 |
| ATP Atlanta | 2019/07/21 18:20 | Viktor Troicki v Ryan Harrison | 6-4,5-7,6-7 |
| French Open | 2019/05/21 09:35 | Ryan Harrison v Adam Pavlasek | 3-6,7-6,6-7 |
| ATP Houston | 2019/04/10 18:05 | Henri Laaksonen v Ryan Harrison | 6-4,7-5 |
| ATP Houston | 2019/04/08 20:00 | Ryan Harrison v Ivo Karlovic | 6-3,6-4 |
| ATP Miami | 2019/03/18 18:20 | Mikael Ymer v Ryan Harrison | 6-1,6-3 |
| Challenger Phoenix | 2019/03/14 19:50 | Ryan Harrison v Lorenzo Sonego | 4-6,2-6 |
| Challenger Phoenix | 2019/03/13 22:05 | Lloyd Harris v Ryan Harrison | 6-3,4-6,4-6 |