[1] Novak Djokovič 1-6,6-3,6-4 Milos Raonic [30] 2020-08-29 17:00
Stadium: Louis Armstrong Stadium Round: 29 Ground: Hardcourt indoor
Head to Head
| Australian Open | 2020/01/28 08:00 | Milos Raonic v Novak Djokovič | 4-6,3-6,6-7 |
| ATP Cincinnati | 2018/08/17 20:30 | Milos Raonic v Novak Djokovič | 5-7,6-4,3-6 |
| ATP - World Tour Finals | 2016/11/15 20:00 | Novak Djokovič v Milos Raonic | 7-6,7-6 |
| ATP Madrid | 2016/05/06 19:30 | Novak Djokovič v Milos Raonic | 6-3,6-4 |
Home History
| ATP New York | 2020/08/28 18:55 | Novak Djokovič v Roberto Bautista-Agut | 4-6,6-4,7-6 |
| ATP - World Tour Finals | 2020/08/27 10:50 | Dominic Thiem v Novak Djokovič | 0-0 |
| ATP New York | 2020/08/26 19:35 | Novak Djokovič v Jan-Lennard Struff | 6-3,6-1 |
| ATP New York | 2020/08/25 19:30 | Novak Djokovič v Tennys Sandgren | 6-2,6-4 |
| ATP New York | 2020/08/24 23:10 | Novak Djokovič v Ricardas Berankis | 7-6,6-4 |
| Adria Tour | 2020/06/21 18:00 | Novak Djokovič v Andrey Rublev | 0-0 |
| Adria Tour | 2020/06/21 14:40 | Novak Djokovič v Nino Serdarusic | 4-1,4-3 |
| Adria Tour | 2020/06/20 19:25 | Novak Djokovič v Borna Coric | 4-1,4-3 |
Away History
| ATP New York | 2020/08/28 17:00 | Stefanos Tsitsipas v Milos Raonic | 6-7,3-6 |
| 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 |