Stadium: Court 3 North Round: 25 Ground: Hardcourt indoor
| ITF M25 Harlingen | 2019/09/27 00:30 | Adrian Andreev v Watson, Andrew | 6-4,6-3 |
| ITF M25 Harlingen | 2019/09/26 02:55 | Khan, Zane v Watson, Andrew | 4-6,1-6 |
| ITF M25 Harlingen | 2019/09/25 18:30 | Khan, Zane v Watson, Andrew | 4-6,1-5 |
| Houston, Singles Qualifying M-ITF-USA-28A | 2019/09/20 00:00 | Ignat, Dragos Constantin v Watson, Andrew | 6-2,4-6,6-1 |
| Houston, Singles Qualifying M-ITF-USA-28A | 2019/09/18 19:00 | Gray, Jonathan v Watson, Andrew | 2-6,3-6 |
| ITF M15 Champaign | 2019/09/12 19:30 | Liam Draxl v Watson, Andrew | 6-2,7-5 |
| ITF M15 Champaign | 2019/09/10 18:00 | Hamilton, Grey v Watson, Andrew | 1-6,1-6 |
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/06 12:55 | Watson, Andrew v Anton Matusevich | 4-6,6-2,4-6 |
| Columbus III, USA | 2019/09/17 22:00 | Strong Kirchheimer v Enzo Couacaud | 6-2,5-7,0-6 |
| Columbus III, USA | 2019/09/16 17:35 | Cash, Robert v Strong Kirchheimer | 3-6,4-6 |
| Challenger Cary | 2019/09/09 23:15 | Strong Kirchheimer v King, Kevin | 4-6,6-2,2-6 |
| New Haven, USA | 2019/09/04 18:20 | Strong Kirchheimer v Christopher Eubanks | 6-7,4-6 |
| New Haven, USA | 2019/09/03 17:25 | Strong Kirchheimer v Ernesto Escobedo | 6-4,6-4 |
| Winston-Salem, USA | 2019/08/18 19:00 | Damir Dzumhur v Strong Kirchheimer | 4-6,6-2,6-1 |
| Winston-Salem, USA | 2019/08/17 16:00 | Strong Kirchheimer v Krawietz, Kevin | 4-6,6-2,6-4 |
| ITF M25 Memphis | 2019/08/14 17:25 | Roberto Cid Subervi v Strong Kirchheimer | 6-4,6-1 |