Round: 25 Ground: Hardcourt outdoor
| US Open, New York, USA, Qualifying | 2016/08/24 15:00 | Souza, Joao Olavo v Whittington, Andrew | 6-4,6-4 |
| Challenger Granby | 2016/08/05 18:55 | Whittington, Andrew v Frances Tiafoe | 0-6,6-7 |
| Challenger Granby | 2016/08/04 18:15 | Whittington, Andrew v Polansky, Peter | 6-7,6-2,6-4 |
| Challenger Granby | 2016/08/02 16:10 | Gonzalez, Alejandro v Whittington, Andrew | 6-7,2-6 |
| ITF Hong Kong F3 | 2016/06/24 22:00 | Whittington, Andrew v Jumpei Yamasaki | 6-3,6-2 |
| ITF Hong Kong F3 | 2016/06/23 22:00 | Whittington, Andrew v Reinwein, Sami | 6-3,6-4 |
| ITF Hong Kong F3 | 2016/06/22 22:00 | Whittington, Andrew v Ouyang, Bowen | 6-4,7-5 |
| ITF Hong Kong F3 | 2016/06/21 22:00 | Whittington, Andrew v Wishaya Trongcharoenchaikul | 6-3,7-6 |
| Challenger Kaohsiung Qual | 2016/09/18 02:00 | Kibi, Yuya v Yu Hsiou Hsu | 6-1,7-6 |
| Nanchang, China | 2016/09/12 03:40 | Aslan Karatsev v Kibi, Yuya | 6-3,7-6 |
| Challenger Shanghai | 2016/09/08 06:10 | Kibi, Yuya v Jason Jung | 7-6,4-6,3-6 |
| Challenger Shanghai | 2016/09/06 03:20 | Qiu, Zhuoyang v Kibi, Yuya | 0-6,2-6 |
| Challenger Bangkok 4 | 2016/09/02 05:55 | Kibi, Yuya v Kavcic, Blaz | 2-6,2-6 |
| Challenger Bangkok 4 | 2016/08/31 04:00 | Kibi, Yuya v Navasirisomboon, Jirat | 6-4,6-0 |
| Challenger Bangkok 4 | 2016/08/29 06:55 | Kibi, Yuya v Niki, Takuto | 4-6,6-3,6-2 |
| Challenger Astana 2 | 2016/07/28 05:00 | Kibi, Yuya v Istomin, Denis | 6-7,6-2,2-6 |