Jim Courier defeated Tim Henman 6-1 6-7 6-4 in the Canada Masters round of 32 on hard. The result followed the form book — Jim Courier came in leading the head-to-head 2–1, defending last year's round of 64. Jim Courier extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R16 | grass | Tim Henman | 4-6 7-5 7-5 6-7(5) 9-7 |
| 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 (57 vs 200). ATP, WTA & Challenger.