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| Hilton Head $10,000 Hard | Jun 8 2003 |
| Qual 1 | Riske | bye |
| Qual 2 | Riske - Kendra Clark | 6-3 4-6 6-1 |
| Qual 3 | Stephanie Hazlett(8) - Riske | 6-3 6-3 |
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| Allentown $25,000 Hard | Jun 15 2003 |
| 1 | Jewel Peterson-WC - Riske-WC | 1-6 6-2 6-2 |
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| Baltimore $10,000 Hard | Jul 20 2003 |
| Qual 1 | Riske - Danielle Lund(8) | 6-1 6-3 |
| Qual 2 | Riske - Theresa Logar | 6-4 6-2 |
| Qual 3 | Riske - Megan Moulton-Levy | 6-2 6-3 |
| 1 | Neha Uberoi - Riske-Q | 6-3 3-6 7-5 |
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| Harrisonburg $10,000 Hard | Aug 3 2003 |
| Qual 1 | Riske - Emily Kwok | 6-2 6-1 |
| Qual 2 | Riske - Shilpa Joshi | 6-0 6-2 |
| Qual 3 | Riske - Tiya Rolle | 6-2 6-2 |
| 1 | Riske-Q - Julia Scaringe-WC | 6-0 6-3 |
| 2 | Shikha Uberoi(3) - Riske-Q | 6-3 6-2 |
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| Peachtree City $25,000 Hard | Sep 14 2003 |
| Qual 1 | Riske-WC - Andrea Van Den Hurk(13) | 6-75 7-5 6-4 |
| Qual 2 | Lauren Kalvaria(7) - Riske-WC | 6-2 6-3 |
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| Raleigh $25,000 Clay | Sep 28 2003 |
| Qual 1 | Riske - Mariana Correa(14) | 6-0 6-2 |
| Qual 2 | Riske - Martina Nedelkova-WC | 7-66 3-6 6-4 |
| 1 | Riske-Q - Anzela Zguna-Q | 6-4 6-3 |
| 2 | Kelly McCain - Riske-Q | 6-4 6-0 |
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| Guadalajara $10,000 Clay | Oct 5 2003 |
| Qual 1 | Riske(1) | bye |
| Qual 2 | Riske(1) - Marina Tavares | 6-1 6-1 |
| 1 | Carla Tiene(2) - Riske-Q | 2-6 6-3 6-4 |
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| CD. Juarez $50,000 Clay | Oct 12 2003 |
| Qual 1 | Riske - Alana van Dervort | 6-2 6-0 |
| Qual 2 | Larissa Carvalho(8) - Riske | 7-5 2-6 7-5 |
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| Mexico City $25,000 Hard | Oct 19 2003 |
| Qual 1 | Christina Zachariadou(2) - Riske | walkover |
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| Pittsburgh $50,000 Hard | Nov 9 2003 |
| 1 | Rossana De Los Rios - Riske-WC | 7-64 6-3 |