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| Boca Raton $25,000 Clay | Jan 18 2009 |
| Qual 1 | Danielle Harmsen - Bertrand | 6-0 6-4 |
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| Lutz $25,000 Clay | Jan 25 2009 |
| Qual 1 | Bertrand - Tereza Mrdeza | 6-2 4-6 6-1 |
| Qual 2 | Bertrand - Leonie Mekel(8) | 2-6 6-4 6-3 |
| Qual 3 | Bertrand - Lena Litvak(15) | 7-5 6-3 |
| 1 | Tetiana Luzhanska(5) - Bertrand | 6-1 5-7 6-2 |
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| Laguna Nigel $25,000 Hard | Feb 1 2009 |
| Qual 1 | Wen-Hsin Hsu - Bertrand | 6-4 6-0 |
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| Rancho Mirage $25,000 Hard | Feb 8 2009 |
| Qual 1 | Bertrand - Katie Ruckert(13) | 4-6 6-3 6-4 |
| Qual 2 | Ashley Weinhold - Bertrand | 6-3 6-3 |
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| Surprise $25,000 Hard | Feb 22 2009 |
| Qual 1 | Nicole Gibbs - Bertrand | 6-2 6-2 |
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| Pelham $25,000 Clay | Apr 5 2009 |
| Qual 1 | Bertrand - Dewonder Davis | 6-0 6-0 |
| Qual 2 | Bertrand - Katie Ruckert(15) | 6-4 6-0 |
| Qual 3 | Yuliana Fedak(2) - Bertrand | 6-3 6-4 |
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| Jackson $25,000 Clay | Apr 12 2009 |
| Qual 1 | Bertrand - Larisa Gorodetsky | 6-0 6-0 |
| Qual 2 | Coco Vandeweghe(9) - Bertrand | 6-2 6-3 |
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| Osprey $25,000 Clay | Apr 19 2009 |
| Qual 1 | Bertrand - Subi Sundaram | 6-0 6-2 |
| Qual 2 | Bertrand - Julia Glushko(1) | 7-62 2-0 |
| Qual 3 | Bertrand - Marina Giral Lores(13) | 6-4 7-5 |
| 1 | Yuliana Fedak(4) - Bertrand | 6-0 6-4 |
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| Dothan $75,000 Clay | Apr 26 2009 |
| Qual 1 | Nicole Rottmann - Bertrand | 6-1 6-3 |
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| Charlottesville $50,000 Clay | May 3 2009 |
| Qual 1 | Bertrand - Amanda Rales | 5-7 7-5 6-4 |
| Qual 2 | Bertrand - Kelly Liggan(3) | 5-7 6-2 6-2 |
| Qual 3 | Bertrand - Shikha Uberoi(5) | 3-6 7-5 6-1 |
| 1 | Alison Riske - Bertrand | 6-3 6-1 |
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| Landisville $10,000 Hard | May 24 2009 |
| 1 | Laura Granville(4) - Bertrand | 6-1 6-0 |
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| Sumter $10,000 Hard | May 31 2009 |
| 1 | Bertrand(7) - Alexandra Moreno-Kaste | 6-2 6-2 |
| 2 | Bertrand(7) - Rachael White | 6-3 1-6 7-64 |
| QF | Petra Rampre(1) - Bertrand(7) | 4-6 6-3 6-2 |
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| Hilton Head Island $10,000 Hard | Jun 7 2009 |
| 1 | Bertrand - Lauren Herring | 6-2 5-7 2-2 |
| 2 | Maria-Fernanda Alves(5) - Bertrand | 6-4 4-6 7-5 |
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| El Paso $25,000 Hard | Jun 14 2009 |
| Qual 1 | Bertrand(4) | bye |
| Qual 2 | Lindsey Nelson - Bertrand(4) | 6-2 6-2 |
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| Brownsville $10,000 Hard | Jun 21 2009 |
| 1 | Ellen Tsay - Bertrand(8) | 6-1 6-3 |
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| Waterloo $25,000 Clay | Jun 28 2009 |
| Qual 1 | Bertrand(1) - Elianne Douglas-Miron | 6-2 6-4 |
| Qual 2 | Bertrand(1) - Carmen Sandor | 6-0 6-1 |
| 1 | Sonja Molnar - Bertrand | 6-2 6-74 6-1 |
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| Boston $50,000 Hard | Jul 5 2009 |
| Qual 1 | Lena Litvak(2) - Bertrand | 6-2 4-6 7-5 |
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| Williamsburg $10,000 Clay | Oct 11 2009 |
| 1 | Bertrand(1) - Monica Neveklovska | 6-0 6-1 |
| 2 | Bertrand(1) - Erica Krisan | 6-2 6-0 |
| QF | Anna Mamalat - Bertrand(1) | 7-60 7-61 |
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| Cleveland $10,000 Clay | Oct 18 2009 |
| 1 | Bertrand(3) - Melissa Schaub | 6-4 6-3 |
| 2 | Bertrand(3) - Kim Grajdek | 6-4 7-64 |
| QF | Kyle S. McPhillips - Bertrand(3) | 7-5 6-2 |