Home History
| 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
| ATP Madrid | 2014/05/09 15:20 | Roberto Bautista-Agut v Santiago Giraldo | 6-3,6-4 |
| ATP Madrid | 2014/05/08 15:00 | Santiago Giraldo v Andy Murray | 6-3,6-2 |
| ATP Madrid | 2014/05/07 17:45 | Jo-Wilfried Tsonga v Santiago Giraldo | 4-6,3-6 |
| ATP Madrid Qual | 2014/05/03 14:20 | Santiago Giraldo v Evgeny Donskoy | 6-3,6-2 |
| ATP Barcelona | 2014/04/27 14:00 | Santiago Giraldo v Kei Nishikori | 2-6,2-6 |
| ATP Barcelona | 2014/04/26 14:00 | Nicolas Almagro v Santiago Giraldo | 5-7,3-6 |
| ATP Barcelona | 2014/04/24 14:55 | Santiago Giraldo v Dominic Thiem | 4-6,6-4,7-5 |
| ATP Barcelona | 2014/04/21 09:00 | Santiago Giraldo v Igor Sijsling | 6-4,6-2 |