Michael Hill advanced when Chris Pressley retired 6-2 1-0 in the USA 6 Masters 4 round of 16. Michael Hill claimed a first win over Chris Pressley in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-11 | USA 6 Masters 3 | SF | hard | Chris Pressley | 5-7 6-4 6-2 |
| 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.