Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| 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 |
| 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 |
| Challenger - Ann Arbor | 2020/01/07 14:00 | Juan Manuel Cerundolo v Patrick Kypson | 6-7,7-5,5-7 |
| ITF - M15 Tallahassee | 2019/12/05 19:10 | Anton Matusevich v Patrick Kypson | 4-6,6-4,7-5 |
| ITF - M15 Tallahassee | 2019/12/04 17:55 | Ronald Hohmann v Patrick Kypson | 5-7,4-6 |
| ITF - M15 Heraklion | 2019/11/16 12:00 | Jan Zielinski v Patrick Kypson | 6-4,6-2 |
| ITF - M15 Heraklion | 2019/11/16 08:00 | Pedro Vives Marcos v Patrick Kypson | 1-6,4-6 |
| ITF - M15 Heraklion | 2019/11/15 08:00 | Filippo Moroni v Patrick Kypson | 3-6,4-6 |
| ITF - M15 Heraklion | 2019/11/14 08:40 | Patrick Kypson v Aidan Mchugh | 6-3,6-0 |
| ITF - M15 Heraklion | 2019/11/12 07:30 | Patrick Kypson v Jordan Hasson | 6-1,6-1 |