By surface
| Surface | Jim Courier | Horacio De La Pena |
|---|---|---|
| Clay | 2 | 1 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 1993-05-10 | ATP | Rome Masters | Round of 64 | Clay | Jim Courier | 6-2 | 6-1 | |||
| 1991-05-06 | ATP | Hamburg Masters | Round of 32 | Clay | Horacio De La Pena | 7-63 | 2-6 | 4-6 | ||
| 1988-04-25 | ATP | Charleston | Quarterfinal | Clay | Jim Courier | 6-3 | 7-6 |