Matteo Colla defeated Maxime Boye 7-6 6-2 in the France F7 qualifying round on clay. Matteo Colla extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 2 | SF | clay | Maxime Boye | 7-6 6-3 |
| 1999-05-31 | Italy F10 | R16 | clay | Matteo Colla | 7-5 6-1 |