Toronto/Montreal, Canada, 
)
Cincinnati, OH, USA, 
Grigor Dimitrov (Bulgaria) 1 - 1 Alexei Popyrin (Australia)
| Date | Tournament | Surface | Rd | Opp. Rank |
Winner | Score |
|---|---|---|---|---|---|---|
| 01 Sep 2021 |
US Open Flushing Meadows, NY, USA Grand Slam |
R64 | Alexei Popyrin (AUS) | 6-7(4) 6-7(4) 0-4 ret. | ||
| 05 Feb 2021 |
Melbourne Summer Set Melbourne, Australia ATP Tour 250 |
R16 | Grigor Dimitrov (BUL) | 6-4 6-7(5) 6-3 |