Christian Schaffkes defeated Scott Humphries 6-4 7-6 in the Caribbean 2 Masters 4 round of 16 on hard. The upset overturned the form book — Scott Humphries came in leading the head-to-head 2–0, but Christian Schaffkes had been the form player, winning 6 of their last 9 on hard. Christian Schaffkes claimed a first win over Scott Humphries in three meetings, narrowing 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 3 | SF | hard | Scott Humphries | 4-6 7-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.