Adam Kennedy defeated Scott Willinsky 6-3 6-4 in the Jamaica F18 round of 32 on clay. The upset overturned the form book — Scott Willinsky came in leading the head-to-head 1–0. Adam Kennedy claimed a first win over Scott Willinsky in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-04-22 | Jamaica F3 | R32 | hard | Scott Willinsky | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.