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| Australian Open Hard | Jan 30 2005 |
| Qual 1 | Jackson - Stanislava Hrozenska | 7-5 6-0 |
| Qual 2 | Angela Haynes(6) - Jackson | 6-1 6-4 |
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| Waikoloa $50,000 Hard | Jan 30 2005 |
| 1 | Jackson(2) - Mary Gambale | 6-0 6-3 |
| 2 | Jackson(2) - Jennifer Tuchband-WC | 6-1 6-0 |
| QF | Hana Sromova(7) - Jackson(2) | 6-3 7-5 |
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| Midland $75,000 Hard | Feb 13 2005 |
| 1 | Suchanun Viratprasert - Jackson(4) | 6-4 6-4 |
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| Memphis Tier III Hard | Feb 20 2005 |
| 1 | Jackson - Amy Frazier(2) | 7-64 0-6 6-3 |
| 2 | Jackson - Sesil Karatantcheva | 6-3 6-4 |
| QF | Nicole Vaidisova(7) - Jackson | 6-2 6-72 6-4 |
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| Indian Wells Tier I Hard | Mar 20 2005 |
| 1 | Jackson-WC - Anca Barna | 7-64 6-4 |
| 2 | Jackson-WC - Paola Suarez(12) | 7-69 7-5 |
| 3 | Conchita Martinez(23) - Jackson-WC | 6-0 7-5 |
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| Miami Tier I Hard | Apr 3 2005 |
| 1 | Kristina Brandi - Jackson-WC | 6-3 6-2 |
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| Amelia Island Tier II Clay | Apr 10 2005 |
| Qual 1 | Nuria Llagostera Vives(2) - Jackson | 6-3 2-6 6-3 |
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| Charleston Tier I Clay | Apr 17 2005 |
| Qual 1 | Sanda Mamic(12) - Jackson | 4-6 6-1 6-4 |
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| Dothan $75,000 Clay | Apr 24 2005 |
| 1 | Jackson(4) - Neha Uberoi | 6-2 6-3 |
| 2 | Jackson(4) - Vanessa Henke | 6-2 6-4 |
| QF | Milagros Sequera(6) - Jackson(4) | 3-6 6-2 1-0 |
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| Prague Tier IV Clay | May 15 2005 |
| 1 | Jackson - Arantxa Parra Santonja(9) | 6-1 6-1 |
| 2 | Kristina Brandi - Jackson | 6-2 6-3 |
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| Roland Garros Clay | Jun 5 2005 |
| Qual 1 | Mary Gambale - Jackson(15) | 6-3 3-6 6-4 |
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| Surbiton $25,000 Grass | Jun 5 2005 |
| 1 | Jackson - Leanne Baker-Q | 6-2 6-1 |
| 2 | Jackson - Tamarine Tanasugarn(1) | 6-1 7-5 |
| QF | Jackson - Kathrin Woerle-Scheller | 7-5 6-4 |
| SF | Laura Granville(4) - Jackson | 6-4 7-5 |
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| Birmingham Tier III Grass | Jun 12 2005 |
| Qual 1 | Jackson(11) - Jane O'Donoghue | 6-4 6-1 |
| Qual 2 | Jackson(11) - Aiko Nakamura(3) | 6-4 6-0 |
| 1 | Jackson-Q - Kristina Brandi | 3-6 7-5 6-0 |
| 2 | Jackson-Q - Maria Kirilenko(15) | 6-2 6-3 |
| 3 | Laura Granville - Jackson-Q | 7-65 6-4 |
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| Wimbledon Grass | Jul 3 2005 |
| Qual 1 | Jackson(5) - Lenka Nemeckova | 6-1 6-3 |
| Qual 2 | Jackson(5) - Nika Ozegovic | 6-4 6-2 |
| Qual 3 | Jackson(5) - Viktoriya Kutuzova | 7-5 6-2 |
| 1 | Jackson-Q - Marta Marrero | 6-2 6-3 |
| 2 | Lindsay Davenport(1) - Jackson-Q | 6-0 6-3 |
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| Toronto Tier I Hard | Aug 21 2005 |
| Qual 1 | Jackson(10) - Kelly Liggan | 6-4 6-4 |
| Qual 2 | Selima Sfar(21) - Jackson(10) | walkover |
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| New Haven Tier II Hard | Aug 28 2005 |
| Qual 1 | Jackson - Maria Sanchez Lorenzo | 7-64 6-4 |
| Qual 2 | Jackson - Jill Craybas(6) | 1-6 6-1 6-2 |
| Qual 3 | Jackson - Maria Kirilenko(4) | 6-1 6-1 |
| 1 | Jackson-Q - Magdalena Maleeva | 6-4 0-6 6-2 |
| 2 | Jie Zheng-LL - Jackson-Q | 6-3 6-4 |
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| US Open Hard | Sep 11 2005 |
| 1 | Jill Craybas - Jackson | 6-4 2-6 7-5 |
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| Bali Tier III Hard | Sep 18 2005 |
| 1 | Francesca Schiavone(4) - Jackson | 6-4 3-6 6-4 |
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| Beijing Tier II Hard | Sep 25 2005 |
| Qual 1 | Jackson(3) | bye |
| Qual 2 | Jackson(3) - Janet Lee | 6-1 6-3 |
| Qual 3 | Jackson(3) - Viktoriya Kutuzova(6) | 6-3 4-6 6-2 |
| 1 | Maria Kirilenko - Jackson-Q | 7-5 7-5 |
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| Guangzhou Tier III Hard | Oct 2 2005 |
| 1 | Jackson - Viktoriya Kutuzova | 6-2 6-1 |
| 2 | Jie Zheng(5) - Jackson | 6-1 7-5 |
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| Japan Open Tier III Hard | Oct 9 2005 |
| 1 | Jill Craybas - Jackson | 0-6 6-1 6-1 |
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| Bangkok Tier III Hard | Oct 16 2005 |
| 1 | Gisela Dulko(3) - Jackson | 6-4 7-5 |
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| Quebec City Tier III Hard | Nov 6 2005 |
| 1 | Stephanie Dubois-WC - Jackson(7) | 7-5 6-4 |