Todd Woodbridge advanced when Jason Stoltenberg retired 6-3 2-1 in the Dubai round of 16. Todd Woodbridge extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-01-05 | Adelaide | SF | hard | Jason Stoltenberg | 6-4 6-1 |
| 1997-08-04 | Cincinnati Masters | R64 | hard | Todd Woodbridge | 3-6 7-6 6-3 |
| 1996-01-08 | Sydney | QF | hard | Todd Woodbridge | 6-3 5-7 6-2 |
| 1994-07-04 | Newport | QF | grass | Todd Woodbridge | 6-3 5-7 7-6(4) |
| 1991-04-22 | Singapore | QF | hard | Jason Stoltenberg | 6-2 7-6(5) |
| 1990-06-25 | Wimbledon | R128 | grass | Jason Stoltenberg | 6-3 7-5 7-6 |
Averages over each player's completed matches in the selected window (134 vs 174). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About