Jeff Loehr defeated Michael Hill 6-3 7-5 in the USA 1 Masters 4 round of 32 on hard. The upset overturned the form book — Michael Hill came in leading the head-to-head 3–0, but Jeff Loehr had been the form player, winning 5 of their last 8 on hard. Jeff Loehr claimed a first win over Michael Hill in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-05-18 | USA F2 | R16 | clay | Michael Hill | 1-6 6-3 6-3 |
| 1997-04-04 | USA 1 Masters 2 | R64 | hard | Michael Hill | 3-6 6-1 6-2 |
| 1997-04-04 | USA 1 Masters 3 | R32 | hard | Michael Hill | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.