[17] Karen Khachanov 1-6,6-7 Milos Raonic [21] 2020-10-16 15:30
Stadium: CENTER COURT Round: 27 Ground: Hardcourt indoor
Home History
| ATP St Petersburg | 2020/10/15 16:10 | Karen Khachanov v Aslan Karatsev | 4-6,7-5,6-3 |
| ATP St Petersburg | 2020/10/13 14:00 | Karen Khachanov v James Duckworth | 6-4,6-4 |
| French Open | 2020/10/05 13:30 | Novak Djokovic v Karen Khachanov | 6-4,6-3,6-3 |
| French Open | 2020/10/03 13:40 | Cristian Garin v Karen Khachanov | 2-6,6-3,4-6,2-6 |
| French Open | 2020/10/01 09:00 | Jiri Vesely v Karen Khachanov | 1-6,7-6,6-7,6-7 |
| French Open | 2020/09/28 17:40 | Kamil Majchrzak v Karen Khachanov | 6-7,3-6,3-6 |
| ATP Hamburg | 2020/09/24 10:30 | Karen Khachanov v Dusan Lajovic | 1-6,2-6 |
| ATP Hamburg | 2020/09/22 14:25 | Karen Khachanov v Jan-Lennard Struff | 7-6,4-6,7-5 |
Away History
| ATP St Petersburg | 2020/10/15 18:50 | Alexander Bublik v Milos Raonic | 3-6,2-6 |
| ATP St Petersburg | 2020/10/13 12:00 | Jeffrey John Wolf v Milos Raonic | 6-7,1-6 |
| ATP Rome | 2020/09/17 12:05 | Milos Raonic v Dusan Lajovic | 6-7,6-4,2-6 |
| ATP Rome | 2020/09/15 17:10 | Milos Raonic v Adrian Mannarino | 7-6,6-2 |
| US Open | 2020/09/03 17:15 | Vasek Pospisil v Milos Raonic | 6-7,6-3,7-6,6-3 |
| US Open | 2020/09/01 21:55 | Leonardo Mayer v Milos Raonic | 3-6,2-6,3-6 |
| ATP New York | 2020/08/29 17:00 | Novak Djokovic v Milos Raonic | 1-6,6-3,6-4 |
| ATP New York | 2020/08/28 17:00 | Stefanos Tsitsipas v Milos Raonic | 6-7,3-6 |