By surface
| Surface | Milos Raonic | Stefanos Tsitsipas |
|---|---|---|
| Hard | 2 | 1 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2023-08-28 | ATP | US Open | Round of 128 | Hard | Stefanos Tsitsipas | 2-6 | 3-6 | 4-6 | ||
| 2020-08-24 | ATP | Cincinnati Masters | Semifinal | Hard | Milos Raonic | 7-65 | 6-3 | |||
| 2020-01-20 | ATP | Australian Open | Round of 32 | Hard | Milos Raonic | 7-5 | 6-4 | 7-62 |