Enzo Artoni defeated Andrea Stoppini 7-5 6-1 in the Italy F8 qualifying round on clay. The upset overturned the form book — Andrea Stoppini came in leading the head-to-head 1–0. Enzo Artoni claimed a first win over Andrea Stoppini in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-06 | Croatia 1 Masters 4 | R32 | clay | Andrea Stoppini | 6-3 3-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.