Tim Henman defeated Jim Courier 4-6 7-5 7-5 6-7 9-7 in the Wimbledon round of 16 on grass. The upset overturned the form book — Jim Courier came in leading the head-to-head 3–0, defending last year's round of 128. Tim Henman claimed a first win over Jim Courier in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Canada Masters | R32 | hard | Jim Courier | 6-1 6-7(3) 6-4 |
| 1999-04-02 | Davis Cup WG R1: GBR vs USA | RR | hard | Jim Courier | 7-6(2) 2-6 7-6(3) 6-7(10) 7-5 |
| 1996-12-30 | Doha | F | hard | Jim Courier | 7-5 6-7(5) 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 57). ATP, WTA & Challenger.