Thomas Messmer defeated Tom Chicoine 6-2 6-4 in the India 2 Masters 4 semi-final on hard. The upset overturned the form book — Tom Chicoine came in leading the head-to-head 1–0. Thomas Messmer claimed a first win over Tom Chicoine in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | India 2 Masters 3 | QF | hard | Tom Chicoine | 7-5 6-3 |