Round: 25 Ground: Clay
| ATP Paris MD | 2016/11/19 10:00 | Celine Kern v Chelsea May Samways | 6-3,6-2 |
| ATP Paris MD | 2016/11/12 12:00 | Kelia Le Bihan v Chelsea May Samways | 6-3,6-1 |
| ATP Paris MD | 2016/11/06 08:00 | Chelsea May Samways v Anna Ukolova | 2-6,4-6 |
| ATP Paris MD | 2016/10/30 07:00 | Giorgia Pinto v Chelsea May Samways | 6-2,6-2 |
| ITF Australia F8 | 2016/08/08 16:00 | Jawairiah Noordin v Chelsea May Samways | 6-2,4-6,6-0 |
| ITF Australia F8 | 2016/08/07 16:00 | Chelsea May Samways v Marketa Slivova | 6-4,6-0 |
| ITF Women Sharm El Sheikh | 2016/08/02 16:00 | Chelsea May Samways v Zuzana Zlochova | 0-6,1-6 |
| ITF Women Istanbul | 2016/06/21 13:00 | Chelsea May Samways v Zuzana Zlochova | 3-6,1-6 |
| ITF Women Antalya | 2016/12/02 13:10 | Agnes Bukta v Anastasiya Shoshyna | 6-3,6-1 |
| ITF Women Antalya | 2016/12/02 09:15 | Chiara Frapolli v Anastasiya Shoshyna | 1-6,6-2,5-7 |
| ITF Women Antalya | 2016/11/30 07:45 | Leonie Kung v Anastasiya Shoshyna | 5-7,2-6 |
| ITF Women Zawada | 2016/11/18 11:50 | Lesley Pattinama Kerkhove v Anastasiya Shoshyna | 6-4,5-7,6-2 |
| ITF Women Zawada | 2016/11/17 13:00 | Camilla Rosatello v Anastasiya Shoshyna | 2-6,3-6 |
| ITF Women Zawada | 2016/11/15 11:50 | Anastasiya Shoshyna v Tamara Zidansek | 6-0,6-7,7-6 |
| ITF Women Zawada Qual | 2016/11/14 10:00 | Olga Fridman v Anastasiya Shoshyna | 6-0,3-6,2-6 |
| ITF Women Zawada Qual | 2016/11/13 12:40 | Ani Mijacika v Anastasiya Shoshyna | 2-6,1-6 |