Round: 54 Ground: Hardcourt outdoor
| Harare, Singles Qualifying M-ITF-ZIM-01A | 2019/06/19 08:55 | Morgan, Charl v Howard-Tripp, Joshua | 2-6,6-1,6-7 |
| ITF USA F31 | 2018/11/13 19:50 | Howard-Tripp, Joshua v Beiler, Mason | 4-6,6-4,1-6 |
| ITF USA F31 | 2018/11/12 20:00 | Howard-Tripp, Joshua v Bernhard, Taine | 6-4,6-2 |
| ITF Zimbabwe F1 | 2018/06/01 08:00 | Benjamin Lock v Howard-Tripp, Joshua | 6-3,6-3 |
| ITF Zimbabwe F1 | 2018/05/31 08:00 | Howard-Tripp, Joshua v Jacobs, Tuki | 6-4,6-4 |
| ITF Zimbabwe F1 | 2018/05/30 08:30 | Finn Bass v Howard-Tripp, Joshua | 3-6,6-3,5-7 |
| ITF Zimbabwe F1 | 2018/05/29 07:00 | Pallares-Gonzalez, Michael-Ray v Howard-Tripp, Joshua | 0-6,1-6 |
| ITF Zimbabwe F1 | 2017/06/15 07:00 | Hochwalt, Tyler v Howard-Tripp, Joshua | 5-7,7-6,6-4 |
| ITF M15 Pittsburgh | 2019/07/01 14:00 | Hills, Langford v Harper, Cleeve | 4-6,6-1,5-10 |
| Rochester, Singles M-ITF-USA-19A | 2019/06/25 21:15 | Volfson, David v Hills, Langford | 6-4,6-1 |
| Rochester, Singles M-ITF-USA-19A | 2019/06/24 17:00 | Hills, Langford v Richmond, John Harrison | 6-1,6-3 |