By surface
| Surface | Milos Raonic | Tim Smyczek |
|---|---|---|
| Hard | 3 | 0 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2019-07-29 | ATP | Washington | Round of 32 | Hard | Milos Raonic | 6-1 | 6-4 | |||
| 2017-02-20 | ATP | Delray Beach | Round of 32 | Hard | Milos Raonic | 6-1 | 6-4 | |||
| 2015-08-31 | ATP | US Open | Round of 128 | Hard | Milos Raonic | 6-4 | 7-68 | 6-1 |