Tim Henman defeated Grant Stafford 6-4 6-2 in the Miami Masters round of 64 on hard. The result followed the form book — Tim Henman came in leading the head-to-head 3–0, defending last year's round of 64. Tim Henman extended the head-to-head to 4–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-24 | Davis Cup WG PO: GBR vs RSA | RR | hard | Tim Henman | 6-3 7-5 7-6(6) |
| 1998-07-27 | Los Angeles | R32 | hard | Tim Henman | 6-3 6-0 |
| 1997-06-16 | Nottingham | QF | grass | Tim Henman | 3-6 6-3 7-6(6) |
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 37). ATP, WTA & Challenger.