[6] Stefanos Tsitsipas 6-7,3-6 Milos Raonic [30] 2020-08-28 17:00
Stadium: Louis Armstrong Stadium Round: 28 Ground: Hardcourt indoor
Head to Head
| Australian Open | 2020/01/24 08:00 | Stefanos Tsitsipas v Milos Raonic | 5-7,4-6,6-7 |
Home History
| ATP - New York | 2020/08/25 21:30 | John Isner v Stefanos Tsitsipas | 6-7,6-7 |
| ATP - New York | 2020/08/23 21:15 | Kevin Anderson v Stefanos Tsitsipas | 1-6,3-6 |
| Davis Cup | 2020/03/07 04:55 | Jeson Patrombon v Stefanos Tsitsipas | 2-6,1-6 |
| Davis Cup | 2020/03/06 03:00 | Alberto Lim v Stefanos Tsitsipas | 2-6,1-6 |
| ATP - Dubai | 2020/02/29 15:00 | Novak Djokovic v Stefanos Tsitsipas | 6-3,6-4 |
| ATP - Dubai | 2020/02/28 13:00 | Daniel Evans v Stefanos Tsitsipas | 2-6,3-6 |
| ATP - Dubai | 2020/02/27 13:30 | Jan-Lennard Struff v Stefanos Tsitsipas | 6-4,4-6,4-6 |
| ATP - Dubai | 2020/02/26 12:00 | Alexander Bublik v Stefanos Tsitsipas | 6-7,4-6 |
Away History
| ATP - New York | 2020/08/26 23:00 | Milos Raonic v Filip Krajinovic | 4-6,7-6,7-5 |
| ATP - New York | 2020/08/25 21:20 | Andy Murray v Milos Raonic | 2-6,2-6 |
| ATP - New York | 2020/08/24 15:00 | Milos Raonic v Daniel Evans | 6-3,7-5 |
| ATP - New York | 2020/08/22 21:30 | Sam Querrey v Milos Raonic | 4-6,4-6 |
| ATP - Delray Beach | 2020/02/23 15:30 | Reilly Opelka v Milos Raonic | 4-6,7-6,6-3 |
| ATP - Delray Beach | 2020/02/22 01:00 | Steve Johnson v Milos Raonic | 6-7,3-6 |
| ATP - Delray Beach | 2020/02/21 01:20 | Cedrik-Marcel Stebe v Milos Raonic | 5-7,3-6 |
| ATP - Delray Beach | 2020/02/18 18:30 | Denis Istomin v Milos Raonic | 2-6,2-6 |