Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Idanha-a-Nova | 2019/07/12 09:00 | Francisco Dias v Jonathan Gray | 2-6,4-6 |
| ITF M15 Idanha-a-Nova | 2019/07/11 13:20 | Loic Ratsaratany v Jonathan Gray | 3-6,6-7 |
| ITF M15 Idanha-a-Nova | 2019/07/09 09:00 | Daniel Batista v Jonathan Gray | 5-7,6-4,1-6 |
| ITF M15 Singapore | 2019/06/16 03:00 | Aidan Mchugh v Jonathan Gray | 6-2,6-2 |
| ITF M15 Singapore | 2019/06/15 03:00 | Jonathan Gray v Kazuki Nishiwaki | 6-3,7-5 |
| ITF M15 Singapore | 2019/06/14 02:00 | Kelsey Stevenson v Jonathan Gray | 3-6,4-6 |
| ITF M15 Singapore | 2019/06/13 02:00 | Congsup Congcar v Jonathan Gray | 6-4,2-6,3-6 |
| ITF M15 Singapore | 2019/06/12 04:40 | Hao Yuan Ng v Jonathan Gray | 0-6,6-4,2-6 |
| ITF M15 Idanha-a-Nova | 2019/07/09 09:00 | David Jorda Sanchis v Andrew Watson | 5-7,7-6,6-1 |
| ITF M15 Idanha-a-Nova | 2019/07/05 12:45 | Fred Gil v Andrew Watson | 6-4,6-1 |
| ITF M15 Idanha-a-Nova | 2019/07/04 12:25 | Luis Faria v Andrew Watson | 6-7,4-6 |
| Challenger Ilkley | 2019/06/17 11:00 | Viktor Galovic v Andrew Watson | 6-4,6-4 |
| Challenger Surbiton | 2019/06/04 10:00 | Andrew Watson v Yunseong Chung | 2-6,2-6 |
| Challenger Surbiton | 2019/06/03 10:00 | Brydan Klein v Andrew Watson | 6-3,2-6,5-7 |
| ITF M25 Pensacola | 2019/05/09 15:00 | Andrew Watson v Jose Olivares | 7-6,4-6,1-6 |
| ITF M25 Pensacola | 2019/05/08 15:35 | Jordi Arconada v Andrew Watson | 3-6,6-3,4-6 |