Stadium: Court 3 North Round: 26 Ground: Hardcourt indoor
| ITF M25 Norman | 2019/10/01 16:30 | Glasspool, Lloyd v Gray, Jonathan | 3-6,2-6 |
| ITF M25 Harlingen | 2019/09/27 22:00 | Nanda, Govind v Gray, Jonathan | 6-3,4-6,6-2 |
| ITF M25 Harlingen | 2019/09/26 15:00 | Gray, Jonathan v Nick Hardt | 6-3,6-4 |
| ITF M25 Harlingen | 2019/09/25 15:30 | Bothwell, Peter v Gray, Jonathan | 6-3,4-6,4-6 |
| Houston, Singles Qualifying M-ITF-USA-28A | 2019/09/18 19:00 | Gray, Jonathan v Watson, Andrew | 2-6,3-6 |
| Jakarta, Singles Main, M-ITF-INA-02A | 2019/08/22 02:30 | Gray, Jonathan v Schmid, Aaron | 4-6,7-5,2-6 |
| Jakarta, Singles Main, M-ITF-INA-02A | 2019/08/20 06:40 | Gray, Jonathan v Duan, Jia Qi | 7-6,6-2 |
| Jakarta, Singles Main, M-ITF-INA-02A | 2019/08/14 06:00 | Gray, Jonathan v Roelofse, Ruan | 6-7,3-6 |
| ITF M25 Norman | 2019/10/02 15:00 | Mark Whitehouse v Stalder, Reese | 1-6,2-6 |
| ITF M25 Norman | 2019/10/01 15:00 | Stalder, Reese v Zapp, Logan | 3-6,6-2,10-6 |
| ITF M25 Norman | 2019/09/30 15:00 | Stalder, Reese v Monroe, Shane | 7-5,6-3 |
| ITF M25 Norman | 2019/09/29 15:00 | Bothwell, Peter v Stalder, Reese | 3-6,4-6 |
| ITF M15 Fayetteville | 2019/09/19 14:00 | Stalder, Reese v Nick Chappell | 1-6,1-6 |
| ITF M15 Fayetteville | 2019/09/17 16:30 | William Grant v Stalder, Reese | 7-6,4-6,2-6 |
| ITF M15 Champaign | 2019/09/09 17:00 | Stalder, Reese v Henrik Wiersholm | 4-6,0-6 |
| ITF M25 Memphis | 2019/08/12 15:00 | Terry, Matthew v Stalder, Reese | 7-6,6-3 |