Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Knoxville | 2018/11/08 19:00 | Peter Polansky v Christopher Eubanks | 3-6,4-6 |
| Challenger Knoxville | 2018/11/07 19:30 | Peter Polansky v Christian Harrison | 6-2,6-2 |
| Challenger Charlottesville | 2018/11/04 20:00 | Tommy Paul v Peter Polansky | 6-2,6-2 |
| Challenger Charlottesville | 2018/11/03 17:00 | Peter Polansky v Thai-Son Kwiatkowski | 6-2,7-6 |
| Challenger Charlottesville | 2018/11/02 16:30 | Peter Polansky v Jelle Sels | 7-6,6-4 |
| Challenger Charlottesville | 2018/10/31 19:15 | Peter Polansky v Tobias Kamke | 7-5,7-5 |
| Challenger Charlottesville | 2018/10/30 14:00 | Peter Polansky v Jared Hiltzik | 6-2,7-5 |
| ATP Wiedeń | 2018/10/20 11:25 | Peter Polansky v Cameron Norrie | 2-6,1-6 |
| Challenger Knoxville | 2018/11/05 15:00 | Patrick Kypson v Evan Song | 4-6,6-3,3-6 |
| Challenger Knoxville | 2018/11/04 15:00 | Jack Draper v Patrick Kypson | 4-6,2-6 |
| ITF USA F28 | 2018/10/18 15:30 | Ryan Peniston v Patrick Kypson | 6-4,7-6 |
| ITF USA F28 | 2018/10/16 15:00 | Patrick Kypson v Joao Pedro Sorgi | 6-3,6-1 |
| ITF USA F27 | 2018/10/12 16:00 | Patrick Kypson v Ryan Peniston | 6-7,1-6 |
| ITF USA F27 | 2018/10/11 22:00 | Andrew Watson v Patrick Kypson | 3-6,3-6 |
| ITF USA F27 | 2018/10/09 15:00 | Harrison Adams v Patrick Kypson | 2-6,0-6 |
| Challenger Stockton | 2018/10/02 19:00 | Jordan Thompson v Patrick Kypson | 6-2,6-2 |