Todd Martin defeated Jiri Novak 6-7 2-6 6-4 6-4 6-4 in the Wimbledon round of 64 on grass. The result followed the form book — Todd Martin came in leading the head-to-head 2–1, defending last year's round of 64. Todd Martin extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Stuttgart Masters | R16 | carpet | Todd Martin | 6-2 6-4 |
| 1999-10-11 | Vienna | R32 | hard | Jiri Novak | 7-6(3) 6-7(5) 6-4 |
| 1999-06-21 | Wimbledon | R64 | grass | Todd Martin | 7-6(5) 6-4 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 (115 vs 200). ATP, WTA & Challenger.