Maxime Boye defeated Matteo Colla 7-6 6-3 in the Italy 3 Masters 2 semi-final on clay. The upset overturned the form book — Matteo Colla came in leading the head-to-head 2–0. Maxime Boye claimed a first win over Matteo Colla in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-12 | France F7 | QF | clay | Matteo Colla | 7-6 6-2 |
| 1999-05-31 | Italy F10 | R16 | clay | Matteo Colla | 7-5 6-1 |