[164] Alona Kruglov 2-6,2-6 Milos Raonic [37] 2019-11-30 18:30
Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
Home History
| Challenger Liuzhou | 2019/10/27 03:00 | Denis Istomin v Alejandro Davidovich Fokina | 3-6,7-5,6-7 |
| Challenger Liuzhou | 2019/10/25 03:55 | Tung-Lin Wu v Denis Istomin | 2-6,3-6 |
| Challenger Liuzhou | 2019/10/24 03:05 | Denis Istomin v Steven Diez | 4-6,7-6,6-0 |
| Challenger Liuzhou | 2019/10/23 04:55 | Denis Istomin v Makoto Ochi | 7-6,6-3 |
| Challenger Ningbo | 2019/10/15 07:45 | Tsung-Hua Yang v Denis Istomin | 3-6,6-3,6-2 |
| Challenger Nur-Sultan 2 | 2019/10/02 09:50 | Denis Istomin v Julian Lenz | 7-5,6-1 |
| ATP Chengdu | 2019/09/22 03:00 | Alexei Popyrin v Denis Istomin | 6-3,3-6,7-5 |
| Challenger Istanbul | 2019/09/15 12:30 | Ugo Humbert v Denis Istomin | 6-2,6-2 |
Away History
| ATP Paris | 2019/10/30 10:00 | Milos Raonic v Dominic Thiem | 6-7,7-5,4-6 |
| ATP Paris | 2019/10/28 13:30 | Cameron Norrie v Milos Raonic | 3-6,2-6 |
| ATP Vienna | 2019/10/22 13:55 | Hyeon Chung v Milos Raonic | 6-4,7-5 |
| Laver Cup | 2019/09/22 16:35 | Alexander Zverev v Milos Raonic | 6-4,3-6,10-4 |
| Laver Cup | 2019/09/21 17:00 | Rafael Nadal v Milos Raonic | 6-3,7-6 |
| ATP Montreal | 2019/08/05 16:00 | Lucas Pouille v Milos Raonic | 4-6,4-6 |
| ATP Washington | 2019/08/01 20:40 | Milos Raonic v Peter Gojowczyk | 4-6,4-6 |
| ATP Washington | 2019/07/31 21:10 | Milos Raonic v Tim Smyczek | 6-1,6-4 |