Level, 1 wins each over 2 singles meetings since 2021. Last meeting on 01/01/2023 at Adelaide International 1 - Adelaide.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 01/01/2023 | Adelaide International 1 - Adelaide | Round 1 | hard | Kokkinakis | 7-6(4) 6-6 |
| 21/06/2021 | Wimbledon - London | Qualifying 1 | grass | Cressy | 6-7(5) 6-7(3) |
| hard | Kokkinakis 1 - 0 Cressy |
| grass | Kokkinakis 0 - 1 Cressy |
| 2023 | Kokkinakis 1 - 0 Cressy |
| 2021 | Kokkinakis 0 - 1 Cressy |
134 wins, 94 losses since 2021 (58.8%).
Last matches: D D D V D
121 wins, 121 losses since 2021 (50.0%).
Last matches: D V D V D
Level, 1 wins each over 2 singles meetings since 2021.
On 01/01/2023, at Adelaide International 1 - Adelaide (Round 1): Thanasi Kokkinakis won 7-6(4) 6-6.