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| Brisbane International Hard | Jan 11 2009 |
| Qual 1 | Groenefeld - Viktoriya Kutuzova | 6-1 6-4 |
| Qual 2 | Groenefeld - Julia Goerges | 6-3 6-73 7-64 |
| Qual 3 | Groenefeld - Julie Coin | 2-6 6-4 6-4 |
| 1 | Roberta Vinci-Q - Groenefeld-Q | 0-6 6-3 6-1 |
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| Australian Open Hard | Feb 1 2009 |
| 1 | Elena Baltacha-Q - Groenefeld | 6-1 6-4 |
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| Fed Cup First Round | Feb 7 2009 |
| | Patty Schnyder-sui - Groenefeld | 7-60 6-3 |
| | Groenefeld - Timea Bacsinszky-sui | 6-3 6-1 |
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| Dubai Premier Hard | Feb 22 2009 |
| 1 | Alizé Cornet(10) - Groenefeld | 6-4 6-1 |
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| Monterrey International Hard | Mar 8 2009 |
| 1 | Barbora Zahlavova Strycova - Groenefeld | 6-3 2-6 7-64 |
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| Indian Wells Premier Hard | Mar 22 2009 |
| 1 | Groenefeld - Monica Niculescu | 6-3 6-0 |
| 2 | Amélie Mauresmo(17) - Groenefeld | 5-7 6-3 6-4 |
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| Miami Premier Hard | Apr 5 2009 |
| 1 | Groenefeld - Jill Craybas-Q | 6-4 6-1 |
| 2 | Groenefeld - Sara Errani(30) | 6-4 6-3 |
| 3 | Venus Williams(5) - Groenefeld | 7-5 6-3 |
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| Barcelona International Clay | Apr 19 2009 |
| 1 | Séverine Beltrame - Groenefeld | 7-64 6-2 |
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| Fed Cup Play-Off | Apr 25 2009 |
| | Groenefeld - Shuai Peng-chn | 4-6 6-4 6-2 |
| | Jie Zheng-chn - Groenefeld | 7-5 6-4 |
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| Stuttgart Premier Clay | May 3 2009 |
| 1 | Elena Dementieva(2) - Groenefeld-WC | 6-4 3-6 6-3 |
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| Estoril International Clay | May 10 2009 |
| 1 | Groenefeld(8) - Pauline Parmentier | 1-6 6-3 7-61 |
| 2 | Groenefeld(8) - Kristina Barrois | 6-4 6-4 |
| QF | Groenefeld(8) - Sabine Lisicki(4) | 6-2 0-0 |
| SF | Ekaterina Makarova(6) - Groenefeld(8) | 6-3 6-1 |
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| Madrid Premier Clay | May 17 2009 |
| Qual 1 | Groenefeld(5) - Camille Pin | 6-3 6-1 |
| Qual 2 | Groenefeld(5) - Michelle Larcher de Brito | 6-1 6-0 |
| 1 | Groenefeld-Q - Monica Niculescu | 6-1 6-0 |
| 2 | Nadia Petrova(8) - Groenefeld-Q | 4-6 7-63 7-65 |
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| Strasbourg International Clay | May 24 2009 |
| 1 | Monica Niculescu-Q - Groenefeld(7) | 4-6 6-2 6-3 |
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| Roland Garros Clay | Jun 7 2009 |
| 1 | Groenefeld - Amélie Mauresmo(16) | 6-4 6-3 |
| 2 | Gisela Dulko - Groenefeld | 7-65 0-6 6-2 |
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| s-Hertogenbosch International Grass | Jun 21 2009 |
| 1 | Dinara Safina(1) - Groenefeld | 6-0 6-3 |
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| Wimbledon Grass | Jul 5 2009 |
| 1 | Sania Mirza - Groenefeld | 6-2 2-6 6-2 |
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| Palermo International Clay | Jul 19 2009 |
| 1 | Groenefeld - Gisela Dulko(8) | 6-4 6-1 |
| 2 | Groenefeld - Arantxa Rus-Q | 7-65 6-3 |
| QF | Groenefeld - Patty Schnyder(2) | 4-3 |
| SF | Sara Errani(5) - Groenefeld | 6-3 4-6 6-1 |
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| Bad Gastein International Clay | Jul 26 2009 |
| 1 | Groenefeld(7) - Zuzana Ondraskova-Q | 6-4 6-3 |
| 2 | Groenefeld(7) - Tereza Hladikova-LL | 6-3 6-2 |
| QF | Andrea Petkovic - Groenefeld(7) | 6-76 6-3 6-1 |
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| Cincinnati Premier Hard | Aug 16 2009 |
| 1 | Groenefeld - Virginie Razzano(16) | 6-3 3-6 6-4 |
| 2 | Sorana Cirstea - Groenefeld | 6-3 6-2 |
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| Toronto Premier Hard | Aug 23 2009 |
| Qual 1 | Elena Baltacha - Groenefeld(8) | 2-6 7-5 6-3 |
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| Bronx $100,000 Hard | Aug 30 2009 |
| 1 | Groenefeld(1) - Mathilde Johansson | 7-62 6-2 |
| 2 | Julia Goerges - Groenefeld(1) | 6-4 7-5 |
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| US Open Hard | Sep 13 2009 |
| 1 | Jie Zheng(21) - Groenefeld | 6-3 6-2 |
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| Seoul International Hard | Sep 27 2009 |
| 1 | Groenefeld - Sorana Cirstea(4) | 7-63 3-6 6-3 |
| 2 | Groenefeld - Kai-Chen Chang-Q | 6-75 6-4 6-3 |
| QF | Groenefeld - Yung-Jan Chan | 6-0 2-6 7-5 |
| SF | Anabel Medina Garrigues(2) - Groenefeld | 2-6 6-3 6-1 |
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| Pan Pacific Open Premier Hard | Oct 4 2009 |
| 1 | Kateryna Bondarenko-Q - Groenefeld | 6-3 6-1 |
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| Beijing Premier Hard | Oct 11 2009 |
| 1 | Elena Dementieva(4) - Groenefeld | 6-4 6-0 |
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| Linz International Hard | Oct 18 2009 |
| 1 | Groenefeld - Roberta Vinci | 7-5 6-1 |
| 2 | Flavia Pennetta(1) - Groenefeld | 6-3 4-6 6-2 |
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| Luxembourg International Hard | Oct 25 2009 |
| 1 | Katarina Srebotnik - Groenefeld | 7-5 6-3 |