Chris Woodruff defeated Jan Michael Gambill 6-4 3-6 6-7 6-3 6-2 in the Wimbledon round of 128 on grass. The upset overturned the form book — Jan Michael Gambill came in leading the head-to-head 3–1, defending last year's quarter-final. Chris Woodruff narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-03-05 | Delray Beach | QF | hard | Jan Michael Gambill | 5-7 7-6(9) 6-4 |
| 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 (28 vs 200). ATP, WTA & Challenger.