Milangela Morales defeated Diana Ospina 7-6 7-5 in the Allentown PA 25K round of 16 on hard. The upset overturned the form book — Diana Ospina came in leading the head-to-head 1–0. Milangela Morales claimed a first win over Diana Ospina in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-09 | Allentown PA 25K | R16 | hard | Diana Ospina | 7-6(6) 6-7(6) 6-2 |