Stadium: Boris Trajkovski Sports Center Round: 25 Ground: Hardcourt indoor
| ITF USA F33 | 2018/11/23 15:00 | Jack Findel-Hawkins v Andrew Watson | 6-7,6-2,7-6 |
| ITF USA F33 | 2018/11/22 16:45 | Jonathan Chang v Andrew Watson | 4-6,6-7 |
| ITF USA F33 | 2018/11/21 15:00 | Henry Craig v Andrew Watson | 6-4,6-7,4-6 |
| ITF USA F33 | 2018/11/20 15:45 | Andrew Watson v Harrison Adams | 7-5,6-4 |
| ITF USA F31 | 2018/11/16 16:00 | Andrew Watson v Matej Vocel | 3-6,7-5,4-6 |
| ITF USA F31 | 2018/11/15 17:25 | Andrew Watson v Ferran Calvo Eman | 7-5,6-2 |
| ITF USA F31 | 2018/11/14 15:00 | Andrew Watson v Alastair Gray | 6-4,2-6,7-6 |
| ITF USA F28B | 2018/10/25 17:40 | Andrew Watson v Maxime Cressy | 6-7,1-6 |
| ITF USA F34 | 2018/11/29 17:20 | Jenson Brooksby v Nick Chappell | 6-2,6-4 |
| ITF USA F34 | 2018/11/28 17:45 | Nick Chappell v Hady Habib | 6-4,4-6,6-3 |
| ITF USA F34 | 2018/11/27 19:15 | Nick Chappell v Danny Thomas | 6-1,6-4 |
| ITF USA F31 | 2018/11/14 15:00 | Ryan Peniston v Nick Chappell | 7-6,6-0 |
| Challenger Calgary | 2018/10/13 20:55 | Nick Chappell v Mikael Torpegaard | 5-7,4-6 |
| Challenger Monterrey | 2018/09/30 16:00 | Sekou Bangoura v Nick Chappell | 6-1,6-2 |
| Challenger Monterrey | 2018/09/29 16:00 | Nick Chappell v Juan Sebastian Gomez | 6-2,6-2 |
| ITF Canada F7 | 2018/09/15 15:00 | Nick Chappell v Lloyd Glasspool | 6-2,6-0 |