Chris Pressley defeated Michael Hill 5-7 6-4 6-2 in the USA 6 Masters 3 semi-final on hard. Chris Pressley extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-10-10 | USA 6 Masters 4 | R16 | hard | Michael Hill | 6-2 1-0 |
| 1993-07-09 | USA 4 Masters 2 | R64 | hard | Chris Pressley | 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.