Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| ITF USA F27 | 2018/10/10 18:00 | Alexey Nesterov v Watson, Andrew | 7-6,4-6,0-6 |
| ITF USA F27 | 2018/10/08 15:00 | Watson, Andrew v Alexey Nesterov | 4-6,6-3,6-1 |
| ITF USA F27 | 2018/10/07 15:00 | Watson, Andrew v Breitbach, Kai | 6-3,6-1 |
| ITF Great Britain F5 | 2018/09/20 10:30 | Watson, Andrew v Antoine Bellier | 6-7,6-2,6-7 |
| ITF Great Britain F5 | 2018/09/19 10:30 | Aidan Mchugh v Watson, Andrew | 4-6,6-4,1-6 |
| ITF Great Britain F5 | 2018/09/18 10:35 | Watson, Andrew v Sean Hodkin | 6-4,6-2 |
| ITF Great Britain F4 | 2018/09/15 10:00 | Watson, Andrew v Jack Draper | 6-3,6-7,0-6 |
| ITF Great Britain F4 | 2018/09/14 09:30 | Watson, Andrew v Ryan Peniston | 4-6,7-6,6-3 |
| 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 Kelly, Dayne | 6-4,6-1 |
| Challenger Stockton | 2018/09/30 22:50 | Bourchier, Harry v Patrick Kypson | 3-6,5-7 |
| Challenger Stockton | 2018/09/29 21:20 | Gojo, Borna v Patrick Kypson | 4-6,2-6 |
| ATP Washington Qual | 2018/07/28 14:00 | Patrick Kypson v Yosuke Watanuki | 5-7,3-6 |
| Challenger Gatineau Qual | 2018/07/16 14:00 | Patrick Kypson v Grills, Jacob | 3-6,1-6 |
| Challenger Gatineau Qual | 2018/07/15 19:00 | Patrick Kypson v Gojo, Borna | 7-6,6-2 |