Stadium: Center Court Round: 25 Ground: Hardcourt indoor
| Challenger Yokkaichi | 2019/08/08 06:05 | Hyeon Chung v Yusuke Takahashi | 3-6,6-1,6-4 |
| Challenger Yokkaichi | 2019/08/07 03:55 | Hyeon Chung v Matthew Romios | 6-3,6-1 |
| Challenger Chengdu | 2019/08/04 03:30 | Yuichi Sugita v Hyeon Chung | 4-6,3-6 |
| Challenger Chengdu | 2019/08/03 05:30 | Tatsuma Ito v Hyeon Chung | 2-6,6-7 |
| Challenger Chengdu | 2019/08/02 04:00 | Ji Sung Nam v Hyeon Chung | 6-7,6-1,3-6 |
| Challenger Chengdu | 2019/08/01 03:00 | Di Wu v Hyeon Chung | 6-7,7-6,3-6 |
| Challenger Chengdu | 2019/07/30 08:10 | Kento Takeuchi v Hyeon Chung | 3-6,2-6 |
| ATP Rotterdam | 2019/02/11 20:05 | Hyeon Chung v Nikoloz Basilashvili | 6-4,6-7,2-6 |
| 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 |
| Wimbledon | 2019/07/08 15:20 | Guido Pella v Milos Raonic | 3-6,4-6,6-3,7-6,8-6 |
| Wimbledon | 2019/07/05 10:00 | Reilly Opelka v Milos Raonic | 6-7,2-6,1-6 |
| Wimbledon | 2019/07/03 12:10 | Robin Haase v Milos Raonic | 6-7,5-7,6-7 |
| Wimbledon | 2019/07/01 15:05 | Prajnesh Gunneswaran v Milos Raonic | 6-7,4-6,2-6 |
| ATP Queens | 2019/06/21 14:35 | Feliciano Lopez v Milos Raonic | 4-6,6-4,7-6 |