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 4–0, defending last year's round of 128. Tim Henman claimed a first win over Jim Courier in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Canada Masters | R32 | hard | Jim Courier | 6-1 6-7 6-4 |
| 1999-04-02 | Davis Cup WG R1: GBR vs USA | RR | hard | Jim Courier | 7-6 2-6 7-6 6-7 7-5 |
| 1997-01-01 | Doha | F | hard | Jim Courier | 7-5 6-7(5) 6-2 |
| 1996-12-30 | Doha | F | hard | Jim Courier | 7-5 6-7 6-2 |
Averages over each player's completed matches in the selected window (200 vs 55). 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