[30] Milos Raonic 4-6,7-6,7-5 Filip Krajinovic [32] 2020-08-15 07:00
Stadium: Grandstand Round: 27 Ground: Hardcourt indoor
Home History
| 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 |
| ATP New York | 2020/02/13 00:30 | Soonwoo Kwon v Milos Raonic | 7-6,6-7,6-4 |
| Australian Open | 2020/01/28 08:00 | Milos Raonic v Novak Djokovic | 4-6,3-6,6-7 |
| Australian Open | 2020/01/26 02:00 | Milos Raonic v Marin Cilic | 6-4,6-3,7-5 |
| Australian Open | 2020/01/24 08:00 | Stefanos Tsitsipas v Milos Raonic | 5-7,4-6,6-7 |
Away History
| Eastern European Championship | 2020/07/24 16:30 | Filip Krajinovic v Borna Coric | 7-6,7-5 |
| Eastern European Championship | 2020/07/20 12:25 | Filip Krajinovic v Aziz Kijametovic | 6-7,6-3,6-4 |
| Eastern European Championship | 2020/06/25 16:00 | Filip Krajinovic v Nemanja Malesevic | 6-0,6-3 |
| Eastern European Championship | 2020/06/24 14:00 | Filip Krajinovic v Tomislav Jotovski | 6-0,6-1 |
| Eastern European Championship | 2020/06/23 16:00 | Filip Krajinovic v Ergi Kirkin | 6-1,6-0 |
| Adria Tour | 2020/06/14 18:35 | Filip Krajinovic v Dominic Thiem | 3-4,4-2,2-4 |
| Adria Tour | 2020/06/14 13:10 | Filip Krajinovic v Viktor Troicki | 4-0,4-3 |
| Adria Tour | 2020/06/13 20:40 | Novak Djokovic v Filip Krajinovic | 4-2,2-4,1-4 |