Richard Krajicek defeated Tim Henman 5-7 6-2 7-6 in the New Haven quarter-final on hard. The upset overturned the form book — Tim Henman came in leading the head-to-head 2–1, defending last year's quarter-final. Richard Krajicek narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-28 | US Open | R32 | hard | Richard Krajicek | 6-4 3-6 4-6 7-5 7-5 |
| 1998-02-23 | London | R32 | carpet | Tim Henman | 6-7(5) 7-6(2) 7-5 |
| 1997-06-23 | Wimbledon | R16 | grass | Tim Henman | 7-6(7) 6-7(7) 7-6(5) 6-4 |
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 (193 vs 200). ATP, WTA & Challenger.