By surface
| Surface | Milos Raonic | Ryan Harrison |
|---|---|---|
| Hard | 1 | 2 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2016-08-29 | ATP | US Open | Round of 64 | Hard | Ryan Harrison | 7-64 | 5-7 | 5-7 | 1-6 | |
| 2012-02-13 | ATP | San Jose | Semifinal | Hard | Milos Raonic | 7-64 | 6-2 | |||
| 2011-03-10 | ATP | Indian Wells Masters | Round of 32 | Hard | Ryan Harrison | 6-71 | 6-4 | 4-6 |