Scott Humphries defeated Christian Schaffkes 4-6 7-6 7-6 in the Caribbean 2 Masters 3 semi-final on hard. Scott Humphries extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-10-28 | Caribbean 2 Masters 1 | QF | hard | Scott Humphries | 6-2 6-2 |
| 1995-10-28 | Caribbean 2 Masters 4 | R16 | hard | Christian Schaffkes | 6-4 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.