By surface
| Surface | Caleb Boland | Jack W Van Slyke |
|---|---|---|
| Hard | 1 | 1 |
All meetings (2)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 1999-08-16 | WTA | Canadian Open | Round of 64 | Hard | Mirjana Lucic | 3-6 | 7-6 | 3-6 | ||
| 1999-03-18 | WTA | Key Biscayne | Round of 32 | Hard | Patty Schnyder | 3-6 | 4-6 |