Alessandro Da Col defeated Marco Monnecchi 6-3 6-4 in the Italy F3 round of 32 on clay. The upset overturned the form book — Marco Monnecchi came in leading the head-to-head 1–0. Alessandro Da Col claimed a first win over Marco Monnecchi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Italy F1 | R16 | clay | Marco Monnecchi | 7-5 6-0 |