Jan Siemerink defeated Todd Woodbridge 6-4 6-2 in the Long Island quarter-final on hard. The upset overturned the form book — Todd Woodbridge came in leading the head-to-head 4–1, but Jan Siemerink had been the form player, winning 2 of their last 5 on hard. Jan Siemerink narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-14 | Indianapolis | R64 | hard | Todd Woodbridge | 6-3 6-1 |
| 2000-06-26 | Wimbledon | R128 | grass | Todd Woodbridge | 6-4 3-6 7-6 6-2 |
| 2000-01-17 | Australian Open | R128 | hard | Todd Woodbridge | 6-4 6-1 6-3 |
| 1995-10-16 | Vienna | R16 | hard | Todd Woodbridge | 6-4 7-5 |
| 1992-03-30 | Singapore | R32 | hard | Jan Siemerink | 6-3 4-6 6-4 |
Averages over each player's completed matches in the selected window (199 vs 134). 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