Round: 54 Ground: Clay
| ITF Women Santa Margherita | 2016/09/25 07:30 | Alessia Piran v Iesha Shepherd | 6-0,6-2 |
| ITF Women Santa Margherita | 2016/09/18 07:30 | Marcella Cucca v Iesha Shepherd | 6-4,6-0 |
| ITF Women Santa Margherita | 2016/09/11 07:30 | Iesha Shepherd v Amelia Fortescue | 1-6,1-6 |
| Billie Jean King Cup | 2016/02/04 15:00 | Monica Puig v Iesha Shepherd | 6-0,6-0 |
| Billie Jean King Cup | 2016/02/01 15:10 | Melissa Morales v Iesha Shepherd | 6-3,6-1 |