Stadium: Court 1 - CC Round: 29 Ground: Hardcourt outdoor
| ITF USA F27 | 2018/10/10 18:00 | Alexey Nesterov v Andrew Watson | 7-6,4-6,0-6 |
| ITF USA F27 | 2018/10/08 15:00 | Andrew Watson v Alexey Nesterov | 4-6,6-3,6-1 |
| ITF USA F27 | 2018/10/07 15:00 | Andrew Watson v Kai Breitbach | 6-3,6-1 |
| ITF Great Britain F5 | 2018/09/20 10:30 | Andrew Watson v Antoine Bellier | 6-7,6-2,6-7 |
| ITF Great Britain F5 | 2018/09/19 10:30 | Aidan Mchugh v Andrew Watson | 4-6,6-4,1-6 |
| ITF Great Britain F5 | 2018/09/18 10:35 | Andrew Watson v Sean Hodkin | 6-4,6-2 |
| ITF Great Britain F4 | 2018/09/15 10:00 | Andrew Watson v Jack Draper | 6-3,6-7,0-6 |
| ITF Great Britain F4 | 2018/09/14 09:30 | Andrew Watson v Ryan Peniston | 4-6,7-6,6-3 |
| Challenger Binghamton Qual | 2018/07/22 14:45 | Karue Sell v Oliver Crawford | 7-6,6-3 |
| Challenger Binghamton Qual | 2018/07/21 18:30 | Oliver Crawford v Yshai Oliel | 6-3,6-3 |
| Challenger Winnetka Qual | 2018/07/08 15:00 | Oliver Crawford v Alexander Ritschard | 4-6,2-6 |
| Challenger Winnetka Qual | 2018/07/07 17:30 | Aron Hiltzik v Oliver Crawford | 6-4,1-6,3-6 |
| ITF USA F15 | 2018/06/19 14:00 | Tommy Paul v Oliver Crawford | 6-2,6-4 |
| ITF USA F15 Qual | 2018/06/18 15:10 | Ezekiel Clark v Oliver Crawford | 4-6,2-6 |
| ITF USA F15 Qual | 2018/06/17 14:00 | Hunter Johnson v Oliver Crawford | 3-6,0-6 |
| ITF USA F15 Qual | 2018/06/16 15:30 | Yates Johnson v Oliver Crawford | 6-7,3-6 |