Justin Gimelstob defeated Scott Draper 6-3 6-1 in the Canada Masters round of 32 on hard. The upset overturned the form book — Scott Draper came in leading the head-to-head 3–0. Justin Gimelstob claimed a first win over Scott Draper in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-04 | Adelaide | R32 | hard | Scott Draper | 3-6 7-6(6) 6-3 |
| 1998-06-15 | Nottingham | R32 | grass | Scott Draper | 6-3 4-6 7-6(4) |
| 1997-06-16 | Nottingham | R32 | grass | Scott Draper | 6-4 7-5 |
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 157). ATP, WTA & Challenger.