Mark Greenan defeated Jeff Chiang 4-6 6-1 6-3 in the Canada Masters 3 round of 32 on carpet. The upset overturned the form book — Jeff Chiang came in leading the head-to-head 1–0. Mark Greenan claimed a first win over Jeff Chiang in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1992-04-27 | USA 2 Masters 1 | R32 | clay | Jeff Chiang | 6-4 2-6 6-4 |