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| Vale Do Lobo $10,000 Hard | Feb 8 2009 |
| Qual 1 | Van Bennekom(9) | bye |
| Qual 2 | Van Bennekom(9) - Stephanie Mueller | 6-2 6-0 |
| Qual 3 | Van Bennekom(9) - Giulia Bruzzone | 6-0 6-3 |
| Qual 4 | Van Bennekom(9) - Ofir Morag | 6-3 6-3 |
| 1 | Van Bennekom - Marcella Koek(6) | 6-74 7-5 6-1 |
| 2 | Apollonia Melzani - Van Bennekom | 6-1 6-0 |
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| Albufeira $10,000 Hard | Feb 15 2009 |
| Qual 1 | Van Bennekom - Aline Pinheiro | 6-2 6-0 |
| Qual 2 | Van Bennekom - Diana Isaeva | 6-1 6-1 |
| Qual 3 | Van Bennekom - Émilie Bacquet(5) | 6-3 7-63 |
| Qual 4 | Nicolette Van Uitert(9) - Van Bennekom | 6-4 6-1 |
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| Portimao $10,000 Hard | Feb 22 2009 |
| Qual 1 | Van Bennekom(16) | bye |
| Qual 2 | Lucie Kriegsmannova - Van Bennekom(16) | 6-2 6-1 |
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| Apeldoorn $10,000 Clay | Jun 14 2009 |
| 1 | Nicola Geuer - Van Bennekom | 6-2 2-6 7-5 |
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| Alkmaar $10,000 Clay | Jun 21 2009 |
| Qual 1 | Van Bennekom(4) - Eva Wacanno | 6-1 6-2 |
| Qual 2 | Van Bennekom(4) - Priscilla Heise | 6-3 6-1 |
| 1 | Pauline Wong(7) - Van Bennekom | 6-4 7-62 |
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| Rotterdam $10,000 Clay | Jun 28 2009 |
| Qual 1 | Iryna Brémond - Van Bennekom(5) | 6-4 4-6 6-4 |
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| Brussels $10,000 Clay | Jul 12 2009 |
| Qual 1 | Van Bennekom(7) | bye |
| Qual 2 | Van Bennekom(7) - Sandra Duez | 6-0 6-1 |
| Qual 3 | Van Bennekom(7) - Elyne Boeykens | 6-2 2-6 6-0 |
| 1 | Sofie Oyen - Van Bennekom | 6-1 7-63 |
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| Zwevegem $25,000 Clay | Jul 19 2009 |
| Qual 1 | Van Bennekom(11) - Daphne Staelens | 6-1 6-1 |
| Qual 2 | Van Bennekom(11) - Kairangi Vano(7) | 4-6 6-4 6-3 |
| 1 | Van Bennekom - Kristyna Pliskova | 3-6 7-5 6-3 |
| 2 | Kirsten Flipkens(1) - Van Bennekom | 6-3 6-2 |
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| Bree $10,000 Clay | Aug 2 2009 |
| Qual 1 | Van Bennekom(7) | bye |
| Qual 2 | Van Bennekom(7) - Katharina Negrin | 6-2 6-0 |
| Qual 3 | Tereza Bekerova - Van Bennekom(7) | 4-6 6-3 6-2 |
| 1 | Tara Wigan - Van Bennekom | 6-4 2-6 7-5 |
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| Rebecq $10,000 Clay | Aug 9 2009 |
| Qual 1 | Van Bennekom(10) - Kathrin Noesen | 6-4 6-0 |
| Qual 2 | Nathalie Mohn - Van Bennekom(10) | 7-61 7-64 |
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| Enschede $10,000 Clay | Aug 30 2009 |
| 1 | Lesley Kerkhove - Van Bennekom | 6-2 6-4 |
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| Almere $10,000 Clay | Sep 6 2009 |
| 1 | Kiki Bertens - Van Bennekom | 6-3 2-6 6-2 |
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| Alphen a/d Rijn $25,000 Clay | Sep 13 2009 |
| Qual 1 | Katarzyna Piter(3) - Van Bennekom | 6-2 6-1 |
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| Dubrovnik $10,000 Clay | Oct 18 2009 |
| Qual 1 | Van Bennekom(5) | bye |
| Qual 2 | Van Bennekom(5) - Marijana Novakovic | 6-1 6-1 |
| Qual 3 | Van Bennekom(5) - Aleksandra Ludvig | 6-0 6-1 |
| 1 | Van Bennekom - Cristina-Madalina Stancu(7) | 4-6 6-4 7-5 |
| 2 | Karin Morgosova - Van Bennekom | 6-3 4-6 6-2 |
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| Dubrovnik $10,000 Clay | Oct 25 2009 |
| Qual 1 | Van Bennekom(4) | bye |
| Qual 2 | Van Bennekom(4) - Mara Zovko | 6-4 6-0 |
| Qual 3 | Van Bennekom(4) - Bianca Schlumberger | 6-4 6-0 |
| 1 | Van Bennekom - Neira Fatic | 6-0 2-0 |
| 2 | Van Bennekom - Romana Tabak(8) | 6-4 6-3 |
| QF | Van Bennekom - Alexandra Krunic | 0-6 7-62 6-2 |
| SF | Matea Mezak(7) - Van Bennekom | 6-0 6-2 |
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| Sunderland $10,000 Hard | Nov 8 2009 |
| Qual 1 | Van Bennekom(1) | bye |
| Qual 2 | Van Bennekom(1) - Amy Hoburn | 6-0 6-2 |
| 1 | Piia Suomalainen - Van Bennekom | 6-4 5-7 6-1 |
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| Jersey $10,000 Hard | Nov 15 2009 |
| Qual 1 | Van Bennekom(2) | bye |
| Qual 2 | Van Bennekom(2) - Michelle Farley | 6-2 5-7 7-5 |
| 1 | Elizabeth Thomas - Van Bennekom | 6-4 6-1 |
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| Benicarlo $10,000 Clay | Dec 13 2009 |
| Qual 1 | Van Bennekom(7) - Vanda Lukacs | 6-2 6-1 |
| Qual 2 | Van Bennekom(7) - Laura Apaolaza-Miradevilla | 6-1 6-2 |
| Qual 3 | Van Bennekom(7) - Ionela-Andreea Iova(11) | 6-4 4-6 6-3 |
| 1 | Astrid Besser - Van Bennekom | 6-4 0-6 6-2 |
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| Vinaros $10,000 Clay | Dec 20 2009 |
| Qual 1 | Van Bennekom(3) | bye |
| Qual 2 | Van Bennekom(3) - Mercedes Giner Gasco | 7-5 6-2 |
| Qual 3 | Amandine Hesse(13) - Van Bennekom(3) | 6-1 7-5 |