[7] Stefanos Tsitsipas 6-2,6-3,6-4 Milos Raonic [337] 2023-08-28 23:10
Stadium: Louis Armstrong Stadium Round: 23 Ground: Hardcourt outdoor
Head to Head
| ATP New York | 2020/08/28 17:00 | Stefanos Tsitsipas v Milos Raonic | 6-7,3-6 |
| Australian Open | 2020/01/24 08:00 | Stefanos Tsitsipas v Milos Raonic | 5-7,4-6,6-7 |
Home History
| ATP Cincinnati | 2023/08/17 17:00 | Stefanos Tsitsipas v Hubert Hurkacz | 3-6,4-6 |
| ATP Cincinnati | 2023/08/16 19:10 | Stefanos Tsitsipas v Ben Shelton | 7-6,7-6 |
| ATP Toronto | 2023/08/09 18:30 | Stefanos Tsitsipas v Gael Monfils | 4-6,3-6 |
| ATP Los Cabos | 2023/08/06 03:00 | Stefanos Tsitsipas v Alex De Minaur | 6-3,6-4 |
| ATP Los Cabos | 2023/08/05 05:15 | Stefanos Tsitsipas v Borna Coric | 6-3,6-2 |
| ATP Los Cabos | 2023/08/04 04:55 | Stefanos Tsitsipas v Nicolas Jarry | 6-7,7-6,6-2 |
| ATP Los Cabos | 2023/08/03 06:45 | Stefanos Tsitsipas v John Isner | 6-2,6-4 |
| Wimbledon | 2023/07/10 12:25 | Christopher Eubanks v Stefanos Tsitsipas | 3-6,7-6,3-6,6-4,6-4 |
Away History
| ATP Toronto | 2023/08/10 16:30 | Mackenzie McDonald v Milos Raonic | 6-3,6-3 |
| ATP Toronto | 2023/08/09 16:30 | Taro Daniel v Milos Raonic | 4-6,3-6 |
| ATP Toronto | 2023/08/07 23:00 | Milos Raonic v Frances Tiafoe | 6-7,7-6,6-3 |
| Wimbledon | 2023/07/06 13:55 | Milos Raonic v Tommy Paul | 4-6,6-7,7-6,4-6 |
| Wimbledon | 2023/07/05 11:30 | Milos Raonic v Dennis Novak | 6-7,6-4,7-6,6-1 |
| ATP Hertogenbosch | 2023/06/15 15:10 | Jordan Thompson v Milos Raonic | 7-6,6-1 |
| ATP Hertogenbosch | 2023/06/12 12:50 | Milos Raonic v Miomir Kecmanovic | 6-3,6-4 |
| ATP Atlanta | 2021/07/28 23:00 | Milos Raonic v Brandon Nakashima | 7-5,3-6,6-7 |