Chengdu, China, 
)
Grigor Dimitrov (Bulgaria) 2 - 1 Frances Tiafoe (USA)
| Date | Tournament | Surface | Rd | Opp. Rank |
Winner | Score |
|---|---|---|---|---|---|---|
| 08 Jul 2023 |
The Championships Wimbledon, Great Britain Grand Slam |
R32 | Grigor Dimitrov (BUL) | 6-2 6-3 6-2 | ||
| 20 Jan 2019 |
Australian Open Melbourne, Australia Grand Slam |
R16 | Frances Tiafoe (USA) | 5-7 6-7(6) 7-6(1) 5-7 | ||
| 09 Aug 2018 |
National Bank Open Toronto/Montreal, Canada ATP Tour Masters |
R16 | Grigor Dimitrov (BUL) | 7-6(1) 3-6 7-6(4) |