[6] Stefanos Tsitsipas 5-7,4-6,6-7 Milos Raonic [35] 2020-01-24 08:00
Stadium: Margaret Court Arena Round: 25 Ground: Hardcourt outdoor
Home History
| Australian Open | 2020/01/20 08:00 | Stefanos Tsitsipas v Salvatore Caruso | 6-0,6-2,6-3 |
| Kooyong Classic | 2020/01/16 03:20 | Stefanos Tsitsipas v Matteo Berrettini | 7-6,7-6 |
| ATP Cup | 2020/01/07 10:20 | Stefanos Tsitsipas v Nick Kyrgios | 6-7,7-6,6-7 |
| ATP Cup | 2020/01/05 09:30 | Alexander Zverev v Stefanos Tsitsipas | 1-6,4-6 |
| ATP Cup | 2020/01/03 01:35 | Stefanos Tsitsipas v Denis Shapovalov | 6-7,6-7 |
| Mubadala World Tennis Championship | 2019/12/21 15:00 | Rafael Nadal v Stefanos Tsitsipas | 6-7,7-5,7-6 |
| Mubadala World Tennis Championship | 2019/12/20 13:00 | Novak Djokovic v Stefanos Tsitsipas | 6-3,6-7,4-6 |
| Mubadala World Tennis Championship | 2019/12/19 12:00 | Stefanos Tsitsipas v Andrey Rublev | 6-3,6-4 |
Away History
| Australian Open | 2020/01/22 04:45 | Cristian Garin v Milos Raonic | 3-6,4-6,2-6 |
| Australian Open | 2020/01/21 01:35 | Lorenzo Giustino v Milos Raonic | 2-6,1-6,3-6 |
| Kooyong Classic | 2020/01/14 04:35 | Milos Raonic v Soonwoo Kwon | 6-3,6-2 |
| ATP Doha | 2020/01/08 18:05 | Milos Raonic v Corentin Moutet | 6-7,6-7 |
| 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 |