By surface
| Surface | Andres Andrade | Caleb Boland |
|---|---|---|
| Hard | 2 | 1 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2014-09-08 | WTA | Quebec City | Final | Hard | Mirjana Lucic | 4-6 | 3-6 | |||
| 2013-02-25 | WTA | Florianopolis | Round of 32 | Hard | Venus Williams | 3-6 | 3-6 | |||
| 2002-08-26 | WTA | US Open | Round of 128 | Hard | Venus Williams | 0-6 | 0-6 |