Stadium: Court 1 Round: 54 Ground: Clay
| ITF M15 Pittsburgh | 2019/07/01 14:00 | Fainblum, Daniel v Benjamin, Jordan | 4-6,4-6 |
| Rochester, Singles M-ITF-USA-19A | 2019/06/25 21:30 | George Goldhoff v Benjamin, Jordan | 6-1,6-2 |
| Rochester, Singles M-ITF-USA-19A | 2019/06/24 17:00 | Benjamin, Jordan v Kessler, Mcclain | 1-6,6-3,10-7 |
| ITF USA F18 | 2018/06/25 14:00 | Hamilton, Grey v Benjamin, Jordan | 6-1,6-4 |
| ITF USA F16 | 2018/06/16 17:00 | Benjamin, Jordan v Donarski, Sid | 6-7,6-7 |
| ITF USA F20 | 2017/06/18 16:00 | Benjamin, Jordan v Johnson, Yates | 2-6,2-6 |
| ITF USA F18 | 2017/06/11 16:30 | Benjamin, Jordan v Gervais, Washi | 4-6,2-6 |
| ITF USA F18 | 2014/06/26 17:15 | Benjamin, Jordan v Daciek, Patrick | 5-7,4-6 |
| ITF M15 Pittsburgh | 2019/07/01 14:00 | Quinn Vandecasteele v Cohen, Lance | 7-5,6-7,10-5 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2019/06/17 15:00 | Quinn Vandecasteele v Emmett Ward | 4-6,5-7 |
| ITF M25 Wichita | 2019/06/11 16:50 | AL Allaf, Kareem v Quinn Vandecasteele | 6-1,6-2 |
| ITF M25 Wichita | 2019/06/10 15:00 | Quinn Vandecasteele v Sorbo, Jonathan | 6-3,5-7,16-14 |
| ITF M15 Champaign | 2019/06/03 15:00 | Quinn Vandecasteele v Pratt, Jared | 6-1,3-6,5-10 |
| ITF Netherlands F3 | 2018/07/07 09:30 | Roland Stuurman v Quinn Vandecasteele | 6-3,6-1 |
| ITF Belgium F3 Qual | 2018/06/30 07:30 | Quinn Vandecasteele v Giusca, Teodor | 2-6,6-7 |