Ryan Harrison 6-7,7-5,7-5,6-1 Milos Raonic 2016-08-31 18:05
Stadium: Grandstand Round: 24
Home History
| US Open | 2016/08/29 22:05 | Adrian Mannarino v Ryan Harrison | 4-6,6-7,3-6 |
| US Open Qual | 2016/08/26 15:00 | Ryan Harrison v Henri Laaksonen | 6-3,6-2 |
| US Open Qual | 2016/08/25 15:00 | Ryan Harrison v Joris De Loore | 7-6,6-4 |
| US Open Qual | 2016/08/23 17:40 | Ryan Harrison v Cedrik-Marcel Stebe | 7-6,6-3 |
| ATP Cincinnati Qual | 2016/08/13 19:50 | Ryan Harrison v John Millman | 6-4,6-7,4-6 |
| ATP Washington | 2016/07/21 20:00 | Ryan Harrison v Steve Johnson | 4-6,4-6 |
| ATP Washington | 2016/07/20 20:20 | Viktor Troicki v Ryan Harrison | 6-7,4-6 |
| ATP Washington | 2016/07/19 20:00 | Ryan Harrison v Stephane Robert | 7-6,6-3 |
Away History
| US Open | 2016/08/29 23:00 | Dustin Brown v Milos Raonic | 5-7,3-6,4-6 |
| ATP Cincinnati | 2016/08/20 23:00 | Andy Murray v Milos Raonic | 6-3,6-3 |
| ATP Cincinnati | 2016/08/19 17:10 | Milos Raonic v Dominic Thiem | 6-3,6-4 |
| ATP Cincinnati | 2016/08/18 20:55 | Milos Raonic v Yuichi Sugita | 6-1,3-6,6-1 |
| ATP Cincinnati | 2016/08/17 19:35 | Milos Raonic v John Isner | 7-6,7-6 |
| Wimbledon | 2016/07/10 13:00 | Milos Raonic v Andy Murray | 4-6,6-7,6-7 |
| Wimbledon | 2016/07/08 12:00 | Milos Raonic v Roger Federer | 6-3,6-7,4-6,7-5,6-3 |
| Wimbledon | 2016/07/06 12:00 | Sam Querrey v Milos Raonic | 4-6,5-7,7-5,4-6 |