J. Duckworth leads the head-to-head 2-1 since 2018 against C. O'Connell, over 3 matches.
| Surface | C. O'Connell | J. Duckworth |
|---|---|---|
| Hard | 0 | 2 |
| Grass | 1 | 0 |
| Date | Winner | Score | Event |
|---|---|---|---|
| Aug. 3, 2026 | J. Duckworth | 2 - 0 | Montreal · 1/64-finals · hard |
| June 14, 2025 | C. O'Connell | 2 - 0 | London · Semi-finals · grass |
| Aug. 30, 2022 | J. Duckworth | 3 - 1 | US Open · 1/64-finals · hard |