| Date | R | Kodus v Võõrsil | - |
|---|---|---|---|
| 06/11 15:00 | 27 | Jenson Brooksby v Nicolas Mejia | Walkover |
| 06/09 16:30 | 26 | [163] Jenson Brooksby v Jason Kubler [267] | 6-3,6-1 |
| 06/07 20:15 | 25 | [163] Jenson Brooksby v Darian King [318] | 7-6,6-3 |
| 04/18 15:00 | 29 | [124] Denis Kudla v Jenson Brooksby [232] | 3-6,3-6 |
| 04/17 15:00 | 28 | [327] Christian Harrison v Jenson Brooksby [232] | 5-7,1-6 |
| 04/16 17:20 | 27 | Jenson Brooksby v Zane Khan | 6-4,6-3 |
| 04/14 18:15 | 26 | [232] Jenson Brooksby v Altug Celikbilek [251] | 6-3,6-1 |
| 04/12 17:10 | 25 | [151] Jason Jung v Jenson Brooksby [232] | 1-6,4-6 |