Todd Martin defeated Thomas Enqvist 6-2 7-6 in the Hamburg Masters round of 64 on clay. The upset overturned the form book — Thomas Enqvist came in leading the head-to-head 2–1, defending last year's round of 32. Todd Martin narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | Tour Finals | RR | hard | Todd Martin | 6-4 6-1 |
| 1999-11-01 | Paris Masters | R32 | hard | Thomas Enqvist | 4-6 7-6(5) 7-6(6) |
| 1997-10-13 | Lyon | R16 | clay | Thomas Enqvist | 7-5 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 180). ATP, WTA & Challenger.