Todd Martin defeated Yevgeny Kafelnikov 3-6 7-6 6-4 in the Canada Masters round of 64 on hard. The upset overturned the form book — Yevgeny Kafelnikov came in leading the head-to-head 6–1, defending last year's quarter-final. Todd Martin narrowed the head-to-head to 6–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-03-11 | Indian Wells Masters | QF | hard | Todd Martin | 7-6(5) 6-3 |
| 1999-11-22 | Tour Finals | RR | hard | Yevgeny Kafelnikov | 6-4 1-6 6-1 |
| 1999-08-02 | Canada Masters | QF | hard | Yevgeny Kafelnikov | 7-6(8) 6-7(3) 6-4 |
| 1999-01-18 | Australian Open | QF | hard | Yevgeny Kafelnikov | 6-2 7-6(1) 6-2 |
| 1998-10-26 | Stuttgart Masters | R16 | carpet | Yevgeny Kafelnikov | 6-4 7-5 |
| 1998-08-03 | Canada Masters | R32 | hard | Yevgeny Kafelnikov | 6-2 6-3 |
| 1998-05-11 | Rome Masters | R32 | clay | Yevgeny Kafelnikov | 1-6 7-6(4) 6-3 |
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.