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| Bath $10,000 Hard | Mar 23 2008 |
| Qual 1 | Van Bennekom - Amy Sargeant | 6-78 6-4 6-2 |
| Qual 2 | Katharina Brown(1) - Van Bennekom | 6-0 6-3 |
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| Lenzerheide $10,000 Clay | Jun 15 2008 |
| Qual 1 | Van Bennekom - Tsering Dowa | 6-0 6-1 |
| Qual 2 | Van Bennekom - Darja Pribitkow | 6-2 6-1 |
| Qual 3 | Van Bennekom - Kristina Huba | 6-0 6-1 |
| 1 | Van Bennekom - Sally Peers | 1-6 6-4 6-1 |
| 2 | Klaudia Boczova(8) - Van Bennekom | 6-0 6-4 |
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| Alkmaar $10,000 Clay | Jun 22 2008 |
| Qual 1 | Van Bennekom - Marija Zivkovic-Laurenta | 6-0 6-2 |
| Qual 2 | Van Bennekom - Morgane Pons | 4-6 6-3 6-0 |
| 1 | Van Bennekom - Claire Lablans | 7-62 6-3 |
| 2 | Renee Reinhard(6) - Van Bennekom | 7-64 7-63 |
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| Brussels $10,000 Clay | Jul 13 2008 |
| Qual 1 | Van Bennekom - Lea-Katharina Jacob | 4-6 6-0 7-62 |
| Qual 2 | Van Bennekom - Dajana Axinie | 6-1 6-0 |
| Qual 3 | Van Bennekom - Kiki Bertens | 2-6 6-2 6-3 |
| 1 | Émilie Bacquet(7) - Van Bennekom | 6-1 6-2 |
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| Zwevegem $25,000 Clay | Jul 20 2008 |
| Qual 1 | Jasmina Tinjic - Van Bennekom(13) | 6-4 6-4 |
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| Koksijde $10,000 Clay | Aug 17 2008 |
| Qual 1 | Van Bennekom(3) - Giulia Zambaiti | 6-1 6-1 |
| Qual 2 | Van Bennekom(3) - Luana Rednic | 6-1 6-3 |
| 1 | Van Bennekom - Claire Lablans | 5-7 6-1 6-2 |
| 2 | Sandra Soler-Sola - Van Bennekom | 6-0 4-6 6-0 |
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| Enschede $10,000 Clay | Aug 24 2008 |
| 1 | Van Bennekom - Elizabeth Ullathorne | 6-0 3-6 6-3 |
| 2 | Nicolette Van Uitert - Van Bennekom | 2-6 6-4 6-1 |
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| Sunderland $10,000 Hard | Nov 9 2008 |
| Qual 1 | Van Bennekom(2) - Danny Engel | 6-1 6-0 |
| Qual 2 | Nikki Prosser - Van Bennekom(2) | 7-64 6-1 |
| 1 | Iveta Gerlova(1) - Van Bennekom | 6-1 6-3 |
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| Jersey $10,000 Hard | Nov 16 2008 |
| Qual 1 | Van Bennekom(3) | bye |
| Qual 2 | Van Bennekom(3) - Jessica Ren | 7-64 6-2 |
| 1 | Olivia Smith - Van Bennekom | 6-4 3-6 7-63 |
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| Vallduxo $10,000 Clay | Nov 30 2008 |
| Qual 1 | Yevgeniya Kryvoruchko - Van Bennekom | 6-4 6-2 |
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| Vinaros $10,000 Clay | Dec 7 2008 |
| Qual 1 | Van Bennekom - Paula Mocete-Talamantes | 6-0 6-4 |
| Qual 2 | Van Bennekom - Ineke Mergaert(9) | 6-1 6-3 |
| Qual 3 | Van Bennekom - Sofia Kvatsabaia(3) | 6-4 7-5 |
| 1 | Amanda Carreras - Van Bennekom | 6-3 7-5 |
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| Benicarlo $10,000 Clay | Dec 14 2008 |
| Qual 1 | Van Bennekom(10) | bye |
| Qual 2 | Van Bennekom(10) - Alejandra Sala-Juste | 7-5 6-4 |
| Qual 3 | Van Bennekom(10) - Laura Apaolaza-Miradevilla(7) | 6-2 |
| 1 | Van Bennekom - Maria Martinez-Romero | 6-1 6-1 |
| 2 | Nicolette Van Uitert - Van Bennekom | 7-63 7-5 |