Jan Michael Gambill defeated Chris Woodruff 5-7 7-6 6-4 in the Delray Beach quarter-final on hard. Jan Michael Gambill extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-06-25 | Wimbledon | R128 | grass | Chris Woodruff | 6-4 3-6 6-7(4) 6-3 6-2 |
| 2001-01-15 | Australian Open | R128 | hard | Chris Woodruff | 6-3 4-6 4-6 7-5 6-3 |
| 1999-06-14 | Nottingham | R32 | grass | Jan Michael Gambill | 7-6(1) 6-4 |
| 1997-01-06 | Auckland | R16 | hard | Jan Michael Gambill | 5-7 6-2 7-6(2) |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (200 vs 28). ATP, WTA & Challenger.