| BNP Paribas Open | Mar 7, 2024 | 6-3, 6-3 | First Round | Milos Raonic | Sumit Nagal |
| ABN Amro Open | Feb 16, 2024 | 7-6 (7-4), 1-1 | Quarter Finals | Jannik Sinner | Milos Raonic |
| ABN Amro Open | Feb 14, 2024 | 6-4, 6-4 | Second Round | Milos Raonic | Alexander Bublik |
| ABN Amro Open | Feb 12, 2024 | 7-6 (7-5), 6-4 | First Round | Milos Raonic | Jesper De Jong |
| Australian Open | Jan 15, 2024 | 6-7 (6-8), 6-3, 2-0 | First Round | Alex De Minaur | Milos Raonic |
| US Open | Aug 28, 2023 | 6-2, 6-3, 6-4 | First Round | Stefanos Tsitsipas | Milos Raonic |
| Omnium National Bank presented by Rogers | Aug 10, 2023 | 6-3, 6-3 | Third Round | Mackenzie McDonald | Milos Raonic |
| Omnium National Bank presented by Rogers | Aug 9, 2023 | 6-4, 6-3 | Second Round | Milos Raonic | Taro Daniel |
| Omnium National Bank presented by Rogers | Aug 7, 2023 | 6-7 (12-14), 7-6 (7-4), 6-3 | First Round | Milos Raonic | Frances Tiafoe |
| Wimbledon | Jul 6, 2023 | 6-4, 7-6 (7-4), 6-7 (4-7), 6-4 | Second Round | Tommy Paul | Milos Raonic |
