Home History
| Wimbledon | 2014/06/24 13:25 | Milos Raonic v Matthew Ebden | 6-2,6-4,6-4 |
| ATP Halle | 2014/06/11 15:30 | Milos Raonic v Peter Gojowczyk | 4-6,4-6 |
| ATP Madrid | 2014/05/08 12:00 | Milos Raonic v Kei Nishikori | 6-7,6-7 |
| ATP Madrid | 2014/05/06 15:30 | Milos Raonic v Jeremy Chardy | 6-3,6-3 |
| ATP Miami | 2014/03/27 23:00 | Rafael Nadal v Milos Raonic | 4-6,6-2,6-4 |
| ATP Miami | 2014/03/25 21:30 | Milos Raonic v Benjamin Becker | 6-3,6-4 |
| ATP Miami | 2014/03/24 15:00 | Milos Raonic v Guillermo Garcia-Lopez | 6-1,6-2 |
| ATP Miami | 2014/03/22 22:25 | Milos Raonic v Jack Sock | 6-4,7-6 |
Away History
| Wimbledon | 2014/06/24 14:10 | Pierre-Hugues Herbert v Jack Sock | 7-6,2-6,6-7,4-6 |
| Challenger Savannah | 2014/04/27 18:45 | Nick Kyrgios v Jack Sock | 2-6,7-6,6-4 |
| Challenger Savannah | 2014/04/26 17:55 | Filip Krajinovic v Jack Sock | 6-3,4-6,4-6 |
| Challenger Savannah | 2014/04/25 20:30 | Illya Marchenko v Jack Sock | 3-6,4-6 |
| Challenger Savannah | 2014/04/24 23:50 | James Ward v Jack Sock | 5-7,1-6 |
| Challenger Savannah | 2014/04/22 00:00 | Farrukh Dustov v Jack Sock | 6-4,5-7,3-6 |
| Challenger Sarasota | 2014/04/15 18:05 | Jack Sock v Andrea Arnaboldi | 7-5,6-7,1-6 |
| ATP Houston | 2014/04/12 01:10 | Nicolas Almagro v Jack Sock | 6-2,6-4 |