Chengdu, China, 
)
Grigor Dimitrov (Bulgaria) 1 - 1 Brandon Nakashima (USA)
| Date | Tournament | Surface | Rd | Opp. Rank |
Winner | Score |
|---|---|---|---|---|---|---|
| 01 Sep 2022 |
US Open Flushing Meadows, NY, USA Grand Slam |
R64 | Brandon Nakashima (USA) | 6-7(5) 5-7 3-6 | ||
| 10 May 2022 |
Internazionali BNL d'Italia Rome, Italy ATP Tour Masters |
R64 | Grigor Dimitrov (BUL) | 6-3 6-4 |