Head to Head
| ATP Miami | 2016/03/29 00:15 | Jack Sock v Milos Raonic | 6-7,4-6 |
| ATP Washington | 2014/07/30 22:00 | Jack Sock v Milos Raonic | 6-7,6-7 |
| Wimbledon | 2014/06/26 10:30 | Milos Raonic v Jack Sock | 6-3,6-4,6-4 |
| ATP Miami | 2014/03/22 22:25 | Milos Raonic v Jack Sock | 6-4,7-6 |