Tom Chicoine defeated Thomas Messmer 7-5 6-3 in the India 2 Masters 3 qualifying round on hard. The upset overturned the form book — Thomas Messmer came in leading the head-to-head 1–0, but Tom Chicoine had been the form player, winning 1 of their last 4 on hard. Tom Chicoine claimed a first win over Thomas Messmer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | India 2 Masters 4 | SF | hard | Thomas Messmer | 6-2 6-4 |