[1] Andy Murray 5-7,7-6,6-6 Milos Raonic [4] 2016-08-31 14:00
Ground: Hardcourt indoor
Head to Head
| ATP Cincinnati | 2016/08/20 23:00 | Andy Murray v Milos Raonic | 6-3,6-3 |
| Wimbledon | 2016/07/10 13:00 | Milos Raonic v Andy Murray | 4-6,6-7,6-7 |
| ATP Monte Carlo | 2016/04/15 09:00 | Milos Raonic v Andy Murray | 2-6,0-6 |
| ATP Madrid | 2015/05/08 18:10 | Milos Raonic v Andy Murray | 4-6,5-7 |
Home History
| US Open 2016 | 2016/08/31 01:00 | Lukas Rosol v Andy Murray | 3-6,2-6,2-6 |
| ATP Cincinnati | 2016/08/21 20:00 | Andy Murray v Marin Cilic | 4-6,5-7 |
| ATP Cincinnati | 2016/08/20 23:00 | Andy Murray v Milos Raonic | 6-3,6-3 |
| ATP Cincinnati | 2016/08/20 01:50 | Andy Murray v Bernard Tomic | 6-4,6-4 |
| ATP Cincinnati | 2016/08/18 23:00 | Andy Murray v Kevin Anderson | 6-3,6-2 |
| ATP Cincinnati | 2016/08/18 01:10 | Andy Murray v Juan Monaco | 6-3,6-2 |
| Wimbledon | 2016/07/10 13:00 | Milos Raonic v Andy Murray | 4-6,6-7,6-7 |
| Wimbledon | 2016/07/08 15:50 | Tomas Berdych v Andy Murray | 3-6,3-6,3-6 |
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 |