By surface
| Surface | Caleb Boland | Paul O'Donoghue |
|---|---|---|
| Hard | 0 | 2 |
All meetings (2)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2016-08-29 | WTA | US Open | Round of 64 | Hard | Angelique Kerber | 2-6 | 6-77 | |||
| 2016-07-25 | WTA | Montreal | Round of 32 | Hard | Angelique Kerber | 3-6 | 6-4 | 3-6 |