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 |
Home History
| Wimbledon | 2016/06/30 11:15 | Jack Sock v Robin Haase | 6-1,6-3,6-7,6-4 |
| Wimbledon | 2016/06/27 16:15 | Jack Sock v Ernests Gulbis | 6-4,6-4,6-4 |
| French Open | 2016/05/27 09:00 | Jack Sock v Albert Ramos-Vinolas | 7-6,4-6,4-6,6-4,4-6 |
| French Open | 2016/05/25 10:25 | Jack Sock v Dustin Brown | 6-3,7-6,6-2 |
| French Open | 2016/05/22 10:45 | Jack Sock v Robin Haase | 6-3,7-5,3-6,6-7,6-2 |
| ATP Madrid | 2016/05/05 16:55 | Jack Sock v Joao Sousa | 1-6,7-6,2-6 |
| ATP Madrid | 2016/05/04 20:20 | Juan Martin Del Potro v Jack Sock | 4-6,6-7 |
| ATP Madrid | 2016/05/03 10:00 | Jack Sock v Benoit Paire | 2-6,6-2,7-6 |
Away History
| Wimbledon | 2016/06/30 11:45 | Andreas Seppi v Milos Raonic | 6-7,4-6,2-6 |
| Wimbledon | 2016/06/27 14:25 | Pablo Carreno Busta v Milos Raonic | 6-7,2-6,4-6 |
| French Open | 2016/05/29 09:00 | Milos Raonic v Albert Ramos-Vinolas | 2-6,4-6,4-6 |
| French Open | 2016/05/27 09:00 | Milos Raonic v Andrej Martin | 7-6,6-2,6-3 |
| French Open | 2016/05/25 15:50 | Milos Raonic v Adrian Mannarino | 6-1,7-6,6-1 |
| French Open | 2016/05/23 11:35 | Milos Raonic v Janko Tipsarevic | 6-3,6-2,7-6 |
| ATP Madrid | 2016/05/06 19:30 | Novak Djokovic v Milos Raonic | 6-3,6-4 |
| ATP Madrid | 2016/05/05 19:30 | Milos Raonic v Jo-Wilfried Tsonga | 6-4,6-4 |