Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| Challenger Charlottesville | 2018/10/31 15:00 | Darian King v Michael Mmoh | 3-6,4-6 |
| Challenger Las Vegas | 2018/10/26 19:45 | Thanasi Kokkinakis v Darian King | 6-1,6-4 |
| Challenger Las Vegas | 2018/10/24 18:00 | Tommy Paul v Darian King | 4-6,4-6 |
| Challenger Las Vegas | 2018/10/22 20:10 | Darian King v Dominik Koepfer | 6-4,6-4 |
| Challenger Fairfield | 2018/10/09 19:10 | Tommy Paul v Darian King | 6-2,6-2 |
| Challenger Stockton | 2018/10/05 19:40 | Darian King v Maxime Janvier | 5-7,7-5,6-7 |
| Challenger Stockton | 2018/10/04 16:30 | Alex Bolt v Darian King | 4-6,3-6 |
| Challenger Stockton | 2018/10/02 22:50 | Darian King v Philip Hjorth | 6-1,6-1 |
| ITF USA F28B | 2018/10/26 17:40 | Roy Smith v Jonathan Chang | 6-2,6-2 |
| ITF USA F28B | 2018/10/25 21:15 | Roy Smith v Maxime Cressy | 6-3,6-2 |
| ITF USA F28B | 2018/10/25 16:00 | Ronnie Schneider v Roy Smith | 6-2,1-6,3-6 |
| ITF USA F28B | 2018/10/23 15:00 | Roy Smith v Julian Bradley | 6-7,7-5,6-4 |
| Challenger Calgary | 2018/10/13 16:00 | Laurent Lokoli v Roy Smith | 6-3,7-5 |
| ITF Great Britain F6 | 2018/09/26 13:50 | Manuel Guinard v Roy Smith | 6-3,3-6,7-6 |
| ITF Great Britain F6 | 2018/09/25 12:45 | Roy Smith v Jake Hersey | 6-3,6-2 |
| ITF Great Britain F6 | 2018/09/24 09:30 | Roy Smith v Simonas Zukauskas | 6-2,6-1 |