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 |
Home History
| Eisenhower Cup | 2019/03/06 05:35 | Marin Cilic v Milos Raonic | 0-1 |
| Eisenhower Cup | 2019/03/06 03:00 | Gael Monfils v Milos Raonic | 0-1 |
| ATP Dubai | 2019/02/25 11:40 | Milos Raonic v Jan-Lennard Struff | 4-6,7-5,4-6 |
| ATP Rotterdam | 2019/02/13 18:30 | Milos Raonic v Stan Wawrinka | 4-6,6-7 |
| ATP Rotterdam | 2019/02/12 10:00 | Milos Raonic v Philipp Kohlschreiber | 7-6,7-5 |
| Australian Open | 2019/01/23 04:30 | Milos Raonic v Lucas Pouille | 6-7,3-6,7-6,4-6 |
| Australian Open | 2019/01/21 03:10 | Alexander Zverev v Milos Raonic | 1-6,1-6,6-7 |
| Australian Open | 2019/01/19 04:00 | Pierre-Hugues Herbert v Milos Raonic | 4-6,4-6,6-7 |
Away History
| Eisenhower Cup | 2019/03/06 05:41 | Rafael Nadal v Stan Wawrinka | 0-1 |
| Eisenhower Cup | 2019/03/06 03:00 | Stan Wawrinka v Dominic Thiem | 1-0 |
| ATP Acapulco | 2019/03/01 02:20 | Nick Kyrgios v Stan Wawrinka | 7-5,6-7,6-4 |
| ATP Acapulco | 2019/02/28 00:00 | Stan Wawrinka v Steve Johnson | 7-6,6-4 |
| ATP Acapulco | 2019/02/26 02:45 | Ryan Harrison v Stan Wawrinka | 4-6,6-7 |
| ATP Rotterdam | 2019/02/17 14:30 | Stan Wawrinka v Gael Monfils | 3-6,6-1,2-6 |
| ATP Rotterdam | 2019/02/16 18:30 | Kei Nishikori v Stan Wawrinka | 2-6,6-4,4-6 |
| ATP Rotterdam | 2019/02/15 18:30 | Stan Wawrinka v Denis Shapovalov | 6-4,7-6 |