Head to Head
| ATP Rotterdam | 2019/02/13 18:30 | Milos Raonic v Stan Wawrinka | 4-6,6-7 |
| Australian Open | 2019/01/17 01:35 | Stan Wawrinka v Milos Raonic | 7-6,6-7,6-7,6-7 |
| US Open | 2018/08/31 23:35 | Milos Raonic v Stan Wawrinka | 7-6,6-4,6-3 |
| ATP Rotterdam | 2019/02/13 18:30 | Milos Raonic v Stan Wawrinka | 4-6,6-7 |
| Australian Open | 2019/01/17 01:35 | Stan Wawrinka v Milos Raonic | 7-6,6-7,6-7,6-7 |
| US Open | 2018/08/31 23:35 | Milos Raonic v Stan Wawrinka | 7-6,6-4,6-3 |