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| Tallahassee $10,000 Hard | Jan 12 2003 |
| Qual 1 | Jackson | bye |
| Qual 2 | Jackson - Emily Mowery | 6-0 6-0 |
| Qual 3 | Jackson - Courtney Vernon | 6-0 6-0 |
| Qual 4 | Jackson - Shikha Uberoi(1) | 7-5 3-6 6-3 |
| 1 | Tory Zawacki - Jackson-Q | 6-2 6-4 |
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| Miami $10,000 Hard | Jan 26 2003 |
| Qual 1 | Jackson - Georgette Wright | 6-2 6-4 |
| Qual 2 | Jackson - Ahsha Rolle | 6-0 6-0 |
| Qual 3 | Shikha Uberoi(7) - Jackson | 1-6 6-4 6-2 |
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| Key Biscayne Tier I Hard | Mar 30 2003 |
| 1 | Yoon-Jeong Cho - Jackson-WC | 6-4 6-1 |
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| Charlottesville $25,000 Clay | May 18 2003 |
| 1 | Jackson-WC - Seiko Okamoto | 6-2 6-2 |
| 2 | Christina Wheeler(3) - Jackson-WC | 6-2 6-4 |
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| Dallas $10,000 Hard | Jun 22 2003 |
| Qual 1 | Jackson(2) - Lauren Lui | 6-0 6-1 |
| Qual 2 | Jackson(2) - Julia Scaringe | 6-3 6-2 |
| Qual 3 | Jackson(2) - Kelcy Tefft | 6-0 6-0 |
| 1 | Jackson-Q - Christian Thompson-LL | 6-1 6-1 |
| 2 | Jackson-Q - Natallia Dziamidzenka(7) | 6-0 6-1 |
| QF | Jackson-Q - Mayumi Yamamoto-Q | 6-3 6-3 |
| SF | Jackson-Q - Vilmarie Castellvi-Q | 6-3 6-3 |
| F | Jackson-Q - Angela Haynes(4) | 7-65 6-3 |
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| Edmond $10,000 Hard | Jun 29 2003 |
| 1 | Whitney Deason-Q - Jackson | 7-64 3-3 |
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| College Park $25,000 Hard | Jul 13 2003 |
| 1 | Raquel Kops-Jones-WC - Jackson | 6-3 6-2 |
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| Harrisonburg $10,000 Hard | Aug 3 2003 |
| 1 | Jackson - Stephanie Hazlett | 7-63 6-1 |
| 2 | Jackson - Maki Arai(5) | 7-5 6-1 |
| QF | Shikha Uberoi(3) - Jackson | 6-1 6-76 7-62 |
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| Bronx $50,000 Hard | Aug 17 2003 |
| 1 | Jackson-WC - Renata Voracova(8) | 6-2 6-4 |
| 2 | Jie Zheng - Jackson-WC | 6-4 5-7 1-1 |
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| US Open Hard | Sep 7 2003 |
| Qual 1 | Aniko Kapros(21) - Jackson-WC | 6-1 6-1 |
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| Sedona $50,000 Hard | Oct 19 2003 |
| Qual 1 | Jackson(5) - Elizabeth Kaufman | 6-2 6-1 |
| Qual 2 | Jackson(5) - Joslynn Burkett | 6-0 6-2 |
| Qual 3 | Jackson(5) - Jewel Peterson(2) | 6-2 6-3 |
| 1 | Samantha Reeves(2) - Jackson-Q | 0-6 7-60 6-3 |
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| Eugene $50,000 Hard | Nov 16 2003 |
| Qual 1 | Jackson - Alyssa Cohen | 6-2 7-5 |
| Qual 2 | Angelika Bachmann(4) - Jackson | 6-1 6-4 |