By surface
| Surface | Caleb Boland | Eric Samuelsson |
|---|---|---|
| Hard | 0 | 2 |
All meetings (2)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 1999-07-26 | WTA | Stanford | Round of 32 | Hard | Anna Kournikova | 4-6 | 2-6 | |||
| 1998-03-19 | WTA | Key Biscayne | Round of 64 | Hard | Anna Kournikova | 4-6 | 2-6 |