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| Cali $50,000 Clay | Feb 15 2009 |
| 1 | Sara Del Barrio Aragon - Castiblanco | 6-3 7-60 |
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| Bogota International Clay | Feb 22 2009 |
| Qual 1 | Castiblanco - Anna Smith | 7-63 7-5 |
| Qual 2 | Soledad Esperon(3) - Castiblanco | 6-2 6-0 |
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| Lima $10,000 Clay | Mar 22 2009 |
| 1 | Amanda Carreras - Castiblanco | 6-1 6-1 |
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| Lima $10,000 Clay | Mar 29 2009 |
| 1 | Andrea Koch-Benvenuto - Castiblanco | 7-62 7-62 |
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| Lima $10,000 Clay | Apr 5 2009 |
| 1 | Castiblanco - Ximena Siles Luna Violeta | 6-2 6-1 |
| 2 | Tatiana Bua(4) - Castiblanco | 7-5 6-1 |
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| Buenos Aires $10,000 Clay | Apr 19 2009 |
| 1 | Carla Beltrami(7) - Castiblanco | 1-6 6-1 6-4 |
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| Buenos Aires $10,000 Clay | Apr 26 2009 |
| 1 | Castiblanco - Karen Ramirez Rivera | 7-68 7-5 |
| 2 | Veronica Spiegel(1) - Castiblanco | 6-2 6-4 |
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| Buenos Aires $10,000 Clay | May 3 2009 |
| 1 | Lucia Jara Lozano - Castiblanco | 7-5 4-6 6-3 |
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| Santos $25,000 Clay | May 24 2009 |
| 1 | Castiblanco - Karina Venditti | 6-2 6-73 6-4 |
| 2 | Castiblanco - Nathalia Rossi | 4-6 6-4 7-5 |
| QF | Marina Giral Lores - Castiblanco | 6-4 7-63 |
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| Cordoba $10,000 Clay | May 31 2009 |
| 1 | Castiblanco - Barbara Rush | 6-3 6-2 |
| 2 | Maria Irigoyen(2) - Castiblanco | 6-3 6-71 6-1 |
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| Villa del Dique $10,000 Clay | Jun 7 2009 |
| 1 | Castiblanco - Romina Aufieri | 6-0 7-62 |
| 2 | Castiblanco - Guadalupe Moreno | 6-0 1-0 |
| QF | Fernanda Hermenegildo(7) - Castiblanco | 6-4 6-3 |
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| Santa Fe $10,000 Clay | Jun 14 2009 |
| 1 | Castiblanco(8) - Maria Belen Mosca | 6-0 6-0 |
| 2 | Castiblanco(8) - Melanie Delsart | 6-3 6-2 |
| QF | Roxane Vaisemberg(4) - Castiblanco(8) | 6-0 6-2 |
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| Bogota $25,000 Clay | Jul 19 2009 |
| 1 | Castiblanco - Sonya Latycheva | 6-4 7-63 |
| 2 | Castiblanco - Nicole Clerico | 6-4 6-2 |
| QF | Castiblanco - Bianca Botto(5) | 6-1 6-4 |
| SF | Marina Giral Lores(6) - Castiblanco | 7-5 6-1 |
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| Campos do Jordoa $25,000 Hard | Aug 2 2009 |
| 1 | Jorgelina Cravero(1) - Castiblanco | 6-3 6-1 |
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| Mazatlan $10,000 Hard | Sep 13 2009 |
| 1 | Castiblanco(2) - Stephanie Hoffpauir | 6-1 6-2 |
| 2 | Christi Potgieter - Castiblanco(2) | 6-2 6-3 |
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| Los Mochis $10,000 Clay | Sep 20 2009 |
| 1 | Castiblanco(2) - Andressa Garcia | 6-2 6-2 |
| 2 | Dominika Dieskova - Castiblanco(2) | 6-0 6-1 |
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| Saguenay $50,000 Hard | Sep 27 2009 |
| 1 | Stephanie Dubois(1) - Castiblanco | 6-1 6-0 |
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| Las Vegas $50,000 Hard | Oct 4 2009 |
| Qual 1 | Ana-Clara Duarte(8) - Castiblanco | 6-4 6-4 |
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| Mexico City $25,000 Hard | Oct 11 2009 |
| 1 | Frederica Piedade(2) - Castiblanco | 6-4 6-1 |
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| Bayamon $25,000 Hard | Nov 1 2009 |
| Qual 1 | Castiblanco(3) | bye |
| Qual 2 | Castiblanco(3) - Stephanie Theiler | 6-0 6-0 |
| Qual 3 | Castiblanco(3) - Nelo Phiri | 6-4 6-3 |
| 1 | Brittany Augustine - Castiblanco | 6-1 6-2 |
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| Bogota $10,000 Clay | Nov 8 2009 |
| 1 | Castiblanco(2) - Alexandra Moreno-Kaste | 6-1 6-3 |
| 2 | Castiblanco(2) - Stephanie Theiler | 6-1 6-2 |
| QF | Castiblanco(2) - Yana Koroleva(5) | 3-6 6-1 6-3 |
| SF | Andrea Koch-Benvenuto(3) - Castiblanco(2) | 6-3 6-1 |
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| Itajai $10,000 Clay | Nov 15 2009 |
| 1 | Castiblanco(7) - Barbara Gueno | 6-0 6-2 |
| 2 | Natasha Lotuffo - Castiblanco(7) | 1-6 6-4 6-4 |
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| Asuncion $10,000 Clay | Nov 22 2009 |
| 1 | Castiblanco(6) - Patricia Iveth Ku Flores | 6-2 6-4 |
| 2 | Castiblanco(6) - Monique Albuquerque | 6-4 6-1 |
| QF | Roxane Vaisemberg(3) - Castiblanco(6) | 6-1 6-1 |
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| Puebla $25,000 Hard | Nov 29 2009 |
| 1 | Ajla Tomljanovic - Castiblanco | 6-1 6-1 |
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| Buenos Aires $25,000 Clay | Dec 6 2009 |
| 1 | Ana-Clara Duarte(7) - Castiblanco | 6-3 6-4 |