Stadium: Court 2 Round: 46 Ground: Hardcourt indoor
| 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 |
| Challenger Stockton | 2018/10/01 21:00 | Patrick Kypson v Dayne Kelly | 6-4,6-1 |
| Challenger Knoxville | 2018/11/04 16:55 | Evan Song v Stefan Kozlov | 6-4,3-6,6-3 |
| Challenger Charlottesville | 2018/10/28 15:40 | Evan Song v Marcos Giron | 3-6,6-7 |
| Challenger Charlottesville | 2018/10/27 15:25 | Sekou Bangoura v Evan Song | 6-3,6-7,4-6 |
| Challenger Las Vegas | 2018/10/23 19:35 | Thai-Son Kwiatkowski v Evan Song | 6-4,6-4 |
| Challenger Fairfield | 2018/10/07 18:35 | Evan King v Evan Song | 4-6,6-1,6-2 |
| Challenger Fairfield | 2018/10/06 22:40 | Marcus McDaniel v Evan Song | 4-6,3-6 |
| Challenger Stockton | 2018/09/29 23:55 | Evan Song v Tommy Paul | 5-7,6-7 |
| Challenger Columbus | 2018/09/19 17:25 | Jordan Thompson v Evan Song | 6-0,7-5 |